US3527726A - Water-soluble ammonium or amine salts of phosphate esters of styrene-maleic anhydride copolymer - polyalkylene glycol esters - Google Patents
Water-soluble ammonium or amine salts of phosphate esters of styrene-maleic anhydride copolymer - polyalkylene glycol esters Download PDFInfo
- Publication number
- US3527726A US3527726A US745396A US3527726DA US3527726A US 3527726 A US3527726 A US 3527726A US 745396 A US745396 A US 745396A US 3527726D A US3527726D A US 3527726DA US 3527726 A US3527726 A US 3527726A
- Authority
- US
- United States
- Prior art keywords
- maleic anhydride
- styrene
- water
- esters
- polyalkylene glycol
- 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
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
- C10M173/00—Lubricating compositions containing more than 10% water
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
-
- 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 System
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
- C08F222/08—Maleic anhydride with vinyl aromatic monomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
-
- 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
- C10M2201/02—Water
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/02—Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/01—Emulsions, colloids, or micelles
Definitions
- This invention relates to phosphate esters of styrenemaleic anhydride copolymer esters of polyalkylene glycols, to water-soluble ammonium and amine salts thereof, and to aqueous solutions of such salts which have been found to be especially suitable for use as coolants and lubricants in the working of metals.
- Lubricants suitable for use in metal fabrication such as cutting, threading, tapping and the like must effectively cool and lubricate both the tool and the worked metal.
- an enormous amount of heat is generated at the interface of the tool and the metal being worked which heat must be quickly dissipated in order to prevent damage to either the tool or work piece or both. This is accomplished by flooding the interface with a fluid having a high capacity for heat adsorption as well as effective lubricating properties for reducing friction between the tool and work piece.
- the lubricants especially formulated for these purposes are known in the art as cutting fluids or cutting oils.
- Many of the so-called soluble oils, which are widely used as coolants in metal-working operations, are aqueous emulsions of mineral oils in Water.
- These compositions may also contain special ingredients which improve, for example, the lubricity, extreme pressure characteristics and corrosion and rust resistant properties of the coolant.
- the phosphate esters of this invention can be prepared by first reacting, for instance, a styrene-maleic anhydride copolymer with suitable esterifying agents which provide hydroxy-containing ester groups having a molecular weight of about to 6000, preferably about to 1000.
- suitable esterifying agents can be, for example, alkylene oxides of about 2 or 3 carbon atoms, i.e. ethylene oxide, propylene oxide and water-soluble polyalkylene glycols.
- Suitable polyalkylene glycols include the polyethylene glycols and polypropylene glycols of about 100 to 6000, preferably about 150 to 1000 molecular weight. Minor amounts of monofunctional water-soluble alcohols may be present in the esterifying agents, e.g.
- hydroxy-containing ester is then reacted with phosphoric acid as such or a source of phosphoric acid, e.g. phosphorus pentoxide or polyphosphoric acid.
- the reactants are combined in the mole ratio of about 0.25 to 1 mole of polyalkylene glycol and about 0.5 to 1 mole of phosphoric acid per mole of maleic anhydride in the copolymer.
- Any tendency to form a polymer ester from the copolymer and the polyalkylene glycol can be reduced by using copolymers whose functionality or free maleic anhydride groups do not materially exceed about 2.5 per copolymer molecule. This can be accomplished by using copolymers whose molecular weight does not exceed about 1000 or in partially pre-esterifying copolymers of higher molecular Weight with a monofunctional, water-soluble alcohol, for instance, of the type noted above.
- An acid form of the salts of this invention made from a copolymer having a 1:1 mole ratio of styrene to maleic anhydride, and a polyethylene glycol can be represented by the structure:
- x and y are integers and one or both of R and R can be hydrogen or an ester group of the polyethylene glycol or an ester group of the polyethylene glycol ester of the styrene-maleic anhydride copolymer.
- the copolymer could be partially pre-esterifled, or partially esterified when reacted with the polyalkylene glycol, with a minor amount of mono-functional alcohol as noted above, providing the acid form of the salts of this invention have sufiicient salt-forming sites to give a watersoluble ammonium or amine salt.
- Both of the reactions i.e., that between the copolymer and the polyalkylene glycol and that involving the resulting ester and the phosphoric acid component can be conducted at about 50 to C. in the absence of a catalyst. Also, if desired these reactions can be conducted simultaneously.
- the styrene-maleic anhydride copolymer resin used in this invention has a molecular weight of about 400 to 5000, preferably about 500 to 2500, and a molar ratio of styrene to maleic anhydride of about 1:1 to 4:1, preferablyabout 1 to 2: 1.
- Preparation of the styrene-maleic anhydride copolymer can be by known methods. One method is by solution polymerization where the monomers are polymerized in a suitable solvent employing as a polymerization catalyst a free-radical catalyst, huch as a peroxide, preferably benzoyl peroxide, dicumyl peroxide or an alkyl peroxy dicarbonate, at a temperature of about 75 to 300 C.
- Suitable solvents include the aromatic hydrocarbon solvents, such as cumene, p-cymene, xylene, toluene, etc. Other suitable solvents are the ketones, such as methylethylketone.
- the preferred manner of carrying out the polymerization is by what is known as incremental feed addition. By this method the monomers and catalyst are first dissolved in a portion of the solvent in which the polymerization is to be conducted and the re sulting solution fed in increments into a reactor containing solvent heated to reaction temperature, usually the reflux temperature of the mixture.
- the formation of the copolymer causes a heterogeneous system, the polymer layer being the heavier layer and recoverable by merely decanting the upper aromatic solvent layer and drying.
- the formed copolymer is usually soluble in the solvent media so that recovery of the product necessitates a solvent-stripping operation.
- Aqueous solutions of the various water-soluble ammonium salts or water-soluble, salt-forming amines can be employed at ambient temperatures in the present invention to form the salts of the phosphate esters of the styrene-maleic anhydride copolymers.
- Enough ammonium ion or amine is employed to provide a water-soluble salt and generally these reactants are used in amounts of at least about 0.5 mole per free catalyst group of the copolymer-polyalkylene glycol-phosphoric acid reaction product.
- the salt is essentially neutral due to the use of a sufiicient amount of the ammonium ion or amine.
- Preferred water-soluble, salt-forming amines have boiling points above about 200 C.
- These preferred amines include the tertiary amines such as, for example, trifurfurylamines, and hydroxyl alkyl amines of at least 2 carbon atoms in the alkyl groups such as, for example, triethanolamine.
- Glycol amines of molecular weight up to about 1500 or capped glycol amines of molecular weights up to about 5000 are also suitable.
- the metal-working fluids of the present invention are usually prepared as aqueous solution concentrates containing a minor proportion of the amine or ammonium salts.
- these solutions are about 5 to 50 weight percent concentrates which during use in working metals are diluted with greater volumes of Water, e.g. about 5 to 200 or more volumes.
- Example I describes a typical procedure for the preparation of the phosphate esters of this invention.
- the phosphoric acid esters of styrene-maleic anhydride copolymer esters of polyalkylene glycols said phosphate esters being of a styrene-maleic anhydride copolymer having a molecular weight of about 400 to 5000 and a molar ratio of styrene to maleic anhydride of about 1:1 to 4:1 and a polyalkylene glycol having alkylene groups of 2 to 3 carbon atoms and a molecular Weight of about to 6000, said phosphoric acid esters having a mole ratio of polyalkylene glycol to phosphoric acid to maleic anhydride of said styrene maleic anhydride copolymer of about 0.25 to 1:about 0.5 to 1:about 1.
- phosphate ester of claim 1 wherein the molecular weight of said styrene-maleic anhydride copolymer is about 500 to 2500 and the molar ratio of styrene to maleic anhydride is about 1 to 2:1 and the molecular weight of said polyalkylene glycol is about to 1000.
- composition of claim 4 wherein said salt-forming amine has a boiling point above about 200 C.
- composition of claim 6 wherein said salt-forming amine is triethanolamine.
- composition of claim 5 wherein said salt-forming amine is triethanolamine.
Description
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US74539668A | 1968-07-17 | 1968-07-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3527726A true US3527726A (en) | 1970-09-08 |
Family
ID=24996510
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US745396A Expired - Lifetime US3527726A (en) | 1968-07-17 | 1968-07-17 | Water-soluble ammonium or amine salts of phosphate esters of styrene-maleic anhydride copolymer - polyalkylene glycol esters |
Country Status (1)
Country | Link |
---|---|
US (1) | US3527726A (en) |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3657123A (en) * | 1970-03-23 | 1972-04-18 | Atlantic Richfield Co | Lubricant compositions |
US4207405A (en) * | 1977-09-22 | 1980-06-10 | The B. F. Goodrich Company | Water-soluble phosphorus containing carboxylic polymers |
US4636321A (en) * | 1985-09-30 | 1987-01-13 | Reynolds Metals Company | Water soluble lubricant |
US4908209A (en) * | 1983-08-16 | 1990-03-13 | Interface, Inc. | Biocidal delivery system of phosphate ester and method of preparation thereof |
US4935232A (en) * | 1983-08-16 | 1990-06-19 | Interface Research Corporation | Microbiocidal composition and method of preparation thereof |
US4957948A (en) * | 1988-05-05 | 1990-09-18 | Interface, Inc. | Biocidal protective coating for heat exchanger coils |
EP0389967A2 (en) * | 1989-03-27 | 1990-10-03 | Aluminum Company Of America | Compositions useful as lubricants |
US5024840A (en) * | 1984-03-08 | 1991-06-18 | Interface, Inc. | Antimicrobial carpet and carpet tile |
US5032310A (en) * | 1983-08-16 | 1991-07-16 | Interface, Inc. | Microbiocidal cleansing and disinfecting formulations and preparation thereof |
US5133933A (en) * | 1983-08-16 | 1992-07-28 | Interface Research Corporation | Microbiocidal preservative |
US5368757A (en) * | 1991-03-22 | 1994-11-29 | Henkel Corporation | Lubrication for cold forming of metals |
US5474739A (en) * | 1978-02-04 | 1995-12-12 | Interface, Inc. | Microbiocidal composition |
US5547595A (en) * | 1995-02-07 | 1996-08-20 | Henkel Corporation | Aqueous lubricant and process for cold forming metal, particularly pointing thick-walled metal tubes |
US5635192A (en) * | 1988-05-05 | 1997-06-03 | Interface, Inc. | Biocidal polymeric coating for heat exchanger coils |
US6248701B1 (en) * | 1994-05-13 | 2001-06-19 | Henkel Corporation | Aqueous metal coating composition and process with reduced staining and corrosion |
US6706670B2 (en) | 1996-08-30 | 2004-03-16 | Solutia, Inc. | Water soluble metal working fluids |
WO2008094807A3 (en) * | 2007-01-29 | 2009-03-26 | Lubrizol Corp | Lubricant compositions |
EP2966142A1 (en) * | 2014-07-07 | 2016-01-13 | Alex Pasmans | A liquid thermal conduction enhancer composition and method of manufacturing thereof. |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3085986A (en) * | 1959-10-30 | 1963-04-16 | Sinclair Research Inc | Composition comprising a low viscosity styrene-maleic anhydride copolymer and a polyhydric alcohol |
US3245933A (en) * | 1960-05-19 | 1966-04-12 | Sinclair Research Inc | Styrene-maleic anhydride copolymers cross-linked with aliphatic polyhydroxy compounds |
-
1968
- 1968-07-17 US US745396A patent/US3527726A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3085986A (en) * | 1959-10-30 | 1963-04-16 | Sinclair Research Inc | Composition comprising a low viscosity styrene-maleic anhydride copolymer and a polyhydric alcohol |
US3245933A (en) * | 1960-05-19 | 1966-04-12 | Sinclair Research Inc | Styrene-maleic anhydride copolymers cross-linked with aliphatic polyhydroxy compounds |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3657123A (en) * | 1970-03-23 | 1972-04-18 | Atlantic Richfield Co | Lubricant compositions |
US4207405A (en) * | 1977-09-22 | 1980-06-10 | The B. F. Goodrich Company | Water-soluble phosphorus containing carboxylic polymers |
US5474739A (en) * | 1978-02-04 | 1995-12-12 | Interface, Inc. | Microbiocidal composition |
US5032310A (en) * | 1983-08-16 | 1991-07-16 | Interface, Inc. | Microbiocidal cleansing and disinfecting formulations and preparation thereof |
US4908209A (en) * | 1983-08-16 | 1990-03-13 | Interface, Inc. | Biocidal delivery system of phosphate ester and method of preparation thereof |
US4935232A (en) * | 1983-08-16 | 1990-06-19 | Interface Research Corporation | Microbiocidal composition and method of preparation thereof |
US5133933A (en) * | 1983-08-16 | 1992-07-28 | Interface Research Corporation | Microbiocidal preservative |
US5024840A (en) * | 1984-03-08 | 1991-06-18 | Interface, Inc. | Antimicrobial carpet and carpet tile |
US4636321A (en) * | 1985-09-30 | 1987-01-13 | Reynolds Metals Company | Water soluble lubricant |
US4957948A (en) * | 1988-05-05 | 1990-09-18 | Interface, Inc. | Biocidal protective coating for heat exchanger coils |
US5635192A (en) * | 1988-05-05 | 1997-06-03 | Interface, Inc. | Biocidal polymeric coating for heat exchanger coils |
US5639464A (en) * | 1988-05-05 | 1997-06-17 | Interface, Inc. | Biocidal polymeric coating for heat exchanger coils |
EP0389967A3 (en) * | 1989-03-27 | 1991-01-09 | Aluminum Company Of America | Compositions useful as lubricants |
EP0389967A2 (en) * | 1989-03-27 | 1990-10-03 | Aluminum Company Of America | Compositions useful as lubricants |
US5368757A (en) * | 1991-03-22 | 1994-11-29 | Henkel Corporation | Lubrication for cold forming of metals |
US6248701B1 (en) * | 1994-05-13 | 2001-06-19 | Henkel Corporation | Aqueous metal coating composition and process with reduced staining and corrosion |
US5547595A (en) * | 1995-02-07 | 1996-08-20 | Henkel Corporation | Aqueous lubricant and process for cold forming metal, particularly pointing thick-walled metal tubes |
US6706670B2 (en) | 1996-08-30 | 2004-03-16 | Solutia, Inc. | Water soluble metal working fluids |
WO2008094807A3 (en) * | 2007-01-29 | 2009-03-26 | Lubrizol Corp | Lubricant compositions |
US20100144566A1 (en) * | 2007-01-29 | 2010-06-10 | The Lubrizol Corporation | Lubricant Compositions |
US8859471B2 (en) | 2007-01-29 | 2014-10-14 | The Lubrizol Corporation | Lubricant compositions |
EP2966142A1 (en) * | 2014-07-07 | 2016-01-13 | Alex Pasmans | A liquid thermal conduction enhancer composition and method of manufacturing thereof. |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3527726A (en) | Water-soluble ammonium or amine salts of phosphate esters of styrene-maleic anhydride copolymer - polyalkylene glycol esters | |
US3629112A (en) | Aqueous lubricating compositions containing salts of styrene-maleic anhydride copolymers and an inorganic boron compound | |
US3657123A (en) | Lubricant compositions | |
US3980571A (en) | Synthetic lubricant for machining and chipless deformation of metals | |
US3893931A (en) | Ester lubricants suitable for use in aqueous systems | |
US4654155A (en) | Microemulsion lubricant | |
CA1063091A (en) | Biodegradable seal swell additive with low toxicity properties for automatic transmission fluids, power transmission fluids and rotary engine oil applications | |
CA2938598C (en) | Polyalkanoic or polyalkenoic acid based high perormance, water-dilutable lubricity additive for multi-metal metalworking applications | |
CA1039293A (en) | Lubricant compositions | |
EP0152677A2 (en) | Aqueous systems containing organo-borate compounds | |
US5368757A (en) | Lubrication for cold forming of metals | |
US4636321A (en) | Water soluble lubricant | |
US3912642A (en) | Ester lubricants suitable for use in aqueous systems | |
US5391310A (en) | Sulfurized aqueous machining fluid composition | |
US3969236A (en) | Compositions containing monoalkanolamide borates | |
US4414121A (en) | Aqueous lubricating compositions | |
JP3301038B2 (en) | Bio-resistant surfactant and cutting oil formulations | |
US3501404A (en) | Aqueous lubricants for metal working | |
US5348670A (en) | Phosphorous amine lubricant additives | |
US3472772A (en) | Lubricant emulsion containing a vinylmaleic acid thioester or thioether-ester-polymer salt as an emulsifying agent | |
US4218331A (en) | Extreme pressure lubricating compositions | |
JPS6361092A (en) | Metal working oil consisting of aqueous emulsion | |
CA1335522C (en) | Flowable graft and derivatized polymer concentrate and lubricant containing same | |
EP0314700B1 (en) | Norbornyl dimer ester and polyester additives for lubricants and fuels | |
US4539128A (en) | Water-soluble lubricant |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: CHASE MANHATTAN BANK, N.A., THE, A NATIONAL BANKIN Free format text: SECURITY INTEREST;ASSIGNOR:PONY INDUSTRIES, INC.;REEL/FRAME:004796/0001 Effective date: 19861206 Owner name: CIT GROUP/BUSINESS CREDIT, INC., THE, A NEW YORK C Free format text: SECURITY INTEREST;ASSIGNOR:PONY INDUSTRIES, INC.;REEL/FRAME:004796/0001 Effective date: 19861206 Owner name: PONY INDUSTRIES, INC., A CORP. OF DE. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:ATLANTIC RICHFIELD COMPANY, A DE. CORP.;REEL/FRAME:004659/0926 Effective date: 19861219 Owner name: MANUFACTURES HANOVER TRUST COMPANY, A NEW YORK CO Free format text: SECURITY INTEREST;ASSIGNOR:PONY INDUSTRIES, INC.;REEL/FRAME:004796/0001 Effective date: 19861206 |
|
AS | Assignment |
Owner name: PONY INDUSTRIES, INC., A CORP. OF DE Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:MANUFACTURERS HANOVER TRUST COMPANY;REEL/FRAME:005110/0013 Effective date: 19890310 |