USRE31522E - Salt of a polyamide and functional fluid containing same - Google Patents
Salt of a polyamide and functional fluid containing same Download PDFInfo
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- USRE31522E USRE31522E US06/481,494 US48149483A USRE31522E US RE31522 E USRE31522 E US RE31522E US 48149483 A US48149483 A US 48149483A US RE31522 E USRE31522 E US RE31522E
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- polyamide
- salt
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- amine
- functional fluid
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- 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
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- 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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/40—Lubricating compositions characterised by the base-material being a macromolecular compound containing nitrogen
- C10M107/44—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- 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
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
- C10M149/18—Polyamides
Definitions
- This invention pertains to water soluble or dispersible polyamides having a terminal carboxylic acid group and a terminal amine group in the same molecule and salts thereof, their use in lubricants and aqueous functional fluid (e.g. metal working fluid) compositions containing such polyamides or their salts.
- aqueous functional fluid e.g. metal working fluid
- Aqueous based and non-aqueous functional fluids have been employed in such diverse uses as hydraulic fluids, metal working fluids, heat transfer fluids, electronic coolants, damping fluids and lubricants.
- functional fluids are often tailored to have sets of properties and performance characteristics specific to the intended use of the fluid.
- the stability and lubricating characteristics of the functional fluid as a whole and the various components of the fluid play a major role in the performance and utility of the fluid in hydraulic and metal working applications. High stability for the fluid and its components during storage and use as well as high lubricity of the fluid are important and desirable characteristics in the use of the fluid as a hydraulic fluid or mwetal working fluid.
- aqueous based functional fluids have gained in importance because of their safety, environmental, disposal, flammability, performance and economic advantages over non-aqueous functional fluids. These advantages are particularly significant in view of the strong emphasis currently being placed on safety and environmental considerations, especially in metal working operations.
- the economic advantages of aqueous functional fluids over non-aqueous functional fluids have become important in view of the supply problems and increasing price of non-aqueous functional fluids.
- aqueous functional fluids should exhibit high stability during storage and use, as well as provide a high degree of lubricity.
- the aqueous functional fluid should be highly resistant to separation of one or more components from the mixture and resistant to undesirable breakdown (e.g. degradation) of the components of the fluid, especially undesirable degradation of a lubricant component of the fluid. Separation and undesirable degradation of components (especially a lubricant component) of an aqueous functional fluid reduces the effectiveness and useful life of the fluid leading to such undesirable effects as (1) excessive wear of metallic components of hydraulic systems (e.g. pumps and valves) and metal working equipment (e.g.
- aqueous functional fluids have been proposed by the art and a number of such fluids have been and are being used today in such applications as hydraulics and metal working those fluids have exhibited stability and/or lubricity problems which tend to limit or preclude their effective utilization. Improvements in aqueous functional fluids have therefore been continuously sought by persons skilled in the art.
- Another object of this invention is to provide a novel lubricant for use in forming a stable, lubricating aqueous functional fluid.
- a polyamide derivative of a polyoxyalkylene diamine wherein the polyamide has (a) a single terminal carboxylic acid group and a single terminal amine group in the same molecule and (b) a degree of polymerization of from 2 to 10 and the salts of the polyamide formed by the salt of the terminal carboxylic acid group, the terminal amine group or the terminal carboxylic acid and terminal amine groups of the polyamide and (2) an aqueous functional fluid composition comprising (a) water and (b) a lubricant compound selected from the group consisting of a water soluble or dispersible polyamide derivative of a polyoxyalkylene diamine wherein the polyamide has a single terminal carboxylic acid group and a single terminal amine group in the same molecule and a degree of polymerization of from 2 to 10, a water soluble or dispersible salt of a water soluble of dispersible
- R is a divalent aliphatic, aromatic, arylaliphatic, alkylaromatic, cycloaliphatic, heteroaliphatic having oxygen or sulfur hetero chain atoms, heterocyclic having oxygen, sulfur or nitrogen hetero ring atoms or bicyclic radical or the halogenated derivatives thereof,
- R' is a divalent polyoxyalkylene homopolymer or copolymer radical and n is 2 to 10
- an aqueous functional fluid composition comprising (a) water and (b) a lubricant compound selected from the group consisting of a water soluble or dispersible polyamide derivative of a polyoxyalkylene diamine, a water soluble or dispersible salt of a water soluble or dispersible polyamide derivative of a polyoxyalkylene diamine or a water soluble or dispersible salt of a water insoluble polyamide derivative of a polyoxyalkylene diamine wherein the polyamide derivative of a polyoxyalkylene diamine has the following formula ##STR2## where
- R is a divalent aliphatic, aromatic, arylaliphatic, alkylaromatic, cycloaliphatic, heteroaliphatic having oxygen or sulfur hetero chain atoms, heterocyclic having oxygen, sulfur or nitrogen hetero ring atoms or bicyclic radical or the halogenated derivatives thereof,
- R' is a divalent polyoxyalkylene homopolymer or copolymer radical and n is 2 to 10,
- said polyamide and the water soluble or dispersible salts thereof having an average molecular weight of not greater than about 50,000, the water soluble or dispersible salts being formed by the terminal carboxylic acid group, the terminal amine group or both the terminal carboxylic acid and terminal amine groups of the polyamide.
- R is a C 2 -C 12 alkylene, C 2 -C 10 alkenylene, phenylene, C 4 -C 6 cycloaliphatic, mono to di (C 1 to C 4 alkyl) substituted phenylene, phenyl substituted C 2 -C 10 alkylene, phenylene di (C 1 to C 3 alkylene), heteroaliphatic having one to two oxygen or sulfur heterochain atoms and 2 to 10 carbon atoms, heterocyclic having one to two oxygen, sulfur or nitrogen hetero ring atoms and from 5 to 6 atoms in the ring divalent radical or a divalent radical residue obtained by removal of both carboxylic acid groups from a dimerized ethylenically unsaturated C 8 to C 26 fatty acid and R' is a divalent polyoxyalkylene homo
- the salts of the terminal carboxylic acid group of the polyamide, more particularly the polyamide according to formula (I), of this invention are preferred in the practice of the polyamide and aqueous functional fluid composition of this invention.
- the aqueous functional fluid composition of this invention exhibits advantageous lubricity, stability, safety, environmental and disposal characteristics.
- Polyamides according to this invention are useful in metal working fluids and hydraulic fluids to provide or increase lubrication.
- Aqueous functional fluids in accordance with this invention are useful as metal working fluids in metal working processes such as for example milling, drilling, tapping, grinding, turning, drawing, reaming, punching, spinning and rolling.
- R is a divalent aliphatic group it may be straight or branched chain, saturated or unsaturated, preferably it is a divalent straight or branched chain, saturated or monoethylenically unsaturated aliphatic hydrocarbon radical having 2 to 12 carbon atoms.
- examples of the divalent aliphatic group include ethylene, 1,3-propylene, 1,2-propylene, 1,4-butylene, 1,3-butylene, vinylene, 1,6-hexylene, 1,8-octylene, 1,10-decylene and 2-dodecenylene.
- R is a divalent aromatic radical, preferably a phenylene or naphthylene radical
- examples include 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 1,2-naphthylene, 1,4-napthylene, 1,5-naphthylene, 1,6-naphthylene, 1,8-naphthylene, 2,3-naphthylene, 2,6-naphthylene and 2,7-naphthylene.
- R may be a divalent alkyl aromatic radical, preferably a divalent alkyl aromatic radical having one to two C 1 to C 4 alkyl groups bonded to a phenylene group (e.g.
- R there may be used a divalent arylaliphatic group, preferably a divalent arylaliphatic group having a phenyl group bonded to an alkylene group or two alkylene groups bonded to a benzene ring, examples of which include 2-phenyl-1,3-propylene, 2-phenyl-1, 1-ethylene, phenylene-1,2-dimethylene, phenylene-1,3-dimethylene, phenylene-1,4-dimethylene and phenylene-1,4-diethylene.
- R is a divalent cycloaliphatic radical it may have from zero to two double bonds in the ring, preferably a C 4 to C 6 carbocyclic divalent cycloaliphatic radical having zero to two double bonds in the ring, examples of which include 1,2-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1,3-cyclobutylene, 3-cyclobuten-1,2-ylene, 1,2-cyclohexylene,2,5-cyclohexadien-1,4-ylene and 3-cyclohexen-1,2-ylene.
- R is a divalent heteroaliphatic radical having oxygen or sulfur hetero chain atoms, preferably a divalent heteroaliphatic radical having one or two oxygen or sulfur hetero chain atoms and two to six carbon atoms
- examples include --CH 2 --O--CH 2 --,--CH 2 --S--CH 2 --,--CH 2 --CH 2 --S--CH 2 --CH 2 --,--CH 2 --CH 2 --CH 2 --S--CH 2 --CH 2 --CH 2 -- and --CH 2 --CH 2 --CH 2 -- S--S--CH 2 --CH 2 --CH 2 --CH 2 --.
- R may be a divalent heterocyclic radical having one or two oxygen, sulfur or nitrogen hetero ring atoms, preferably a divalent heterocyclic radical having one oxygen, sulfur or nitrogen hetero ring atom and 5 to 6 atoms in the ring, examples of which include 2,3-thiophenediyl, 2,5-thiophenediyl, 2,3-pyrazolediyl, 2,4-furandiyl, 2,5-furandiyl, 3,4-furandiyl, 2,3-pyridinediyl, 2,5-pyridinediyl, 3,5-pyridinediyl, 2,4-pyrrolediyl, 2,3-pyrazinediyl and 2,6-pyrazinediyl.
- R there may be used a divalent internally bridged carbocyclic radical examples of which include bicyclo (2,2,1) heptane-2,3-diyl and 5-norborene-2,3-diyl.
- dicarboxylic acids usable in the preparation of the polyamide according to formula (I), in the practice of the polyamide and aqueous functional fluid composition of this invention there includes, but not limited to, succinic, isosuccinic, chlorosuccinic, glutaric, pyrotartaric, adipic, chloroadipic, pimelic, suberic, chlorosuberic, azelaic, sebacic, brassylic, octadecanedioic, thapsic, eicosanedioic, maleic, fumaric, citriconic, mesaconic, aconitic, 1,2-benzene dicarboxylic, 1,3-benzene dicarboxylic, 1,4-benzene dicarboxylic, tetrachlorophthalic, tetrahydrophthalic, chlorendic, hexahydrophthalic, hexahydroisophthalic, hexahydr
- dicarboxylic acids usable in the preparation of the polyamide according to formula (I) for the practice of the polyamide and aqueous functional fluid composition of this invention include thiodiacetic, 4,4' dithiodibutyric, carboxyphenoxyacetic, 2,3-thiophene dicarboxylic, 2,4-thiophene dicarboxylic, 2,5-thiophene dicarboxylic, 2,3-pyrazoledicarboxylic, 2-imidazoline dicarboxylic, benzyl malonic, phenyl diacetic, phenyl dipropionic, 2,3-furandicarboxylic, 2,4-furandicarboxylic, 2,5-furandicarboxylic, 3,4-furandicarbox
- the corresponding anhydride or acid halide where the acid admits of the formation of the anhydride and acid halide, e.g. acid chloride.
- the corresponding acid halide of the dicarboxylic acid to prepare the polyamide according to formula (I) it is, of course, necessary to convert the terminal acid halide groups of the polyamide product, resulting from the reaction of the acid halide with the amine group terminated polyoxyalkylene homopolymer or copolymer diamine, to the corresponding carboxylic acid group.
- Such conversion of the terminal acid halide groups to carboxylic acid groups may be accomplished by methods well known in the art.
- R' is a divalent polyoxyalkylene homopolymer or copolymer radical.
- divalent radicals are derived from polyoxyalkylene homopolymer and copolymer diamines by removal of both terminal amine groups from said homopolymer and copolymer diamines.
- divalent polyoxyalkylene homopolymer and copolymer radicals there include said divalent radicals resulting from the removal of both terminal amine groups from polyoxyalkylene homopolymer and copolymer diamines such as for example polyoxyethylene diamine, polyoxypropylene diamine, polyoxybutylene diamine, polyoxypropylene/polyoxyethylene block and random copolymer diamine, polyoxypropylene/polyoxyethylene/polyoxypropylene block copolymer diamine, polyoxybutylene/polyoxyethylene/polyoxybutylene block copolymer diamine, polyoxybutylene/polyoxypropylene/polyoxybutylene block copolymer diamine, polyoxypropylene/polyoxybutylene/polyoxypropylene block copolymer diamine, polyoxyethylene/polyoxybutylene block or random copolymer diamine and polyoxypropylene/polyoxybutylene block or random copolymer diamine.
- the polyoxybutylene may contain 1,2-oxybutylene, 2,3-oxybutylene or 1,4-oxybutylene units.
- the length of the polyoxyalkylene blocks i.e. the number of oxyalkylene groups in the block, may vary widely.
- the divalent polyoxyalkylene copolymer radicals are block terpolymer radicals (e.g.
- the terminal polyoxyalkylene blocks may be polyoxyethylene, polyoxypropylene or polyoxybutylene blocks containing as few as 2 oxyethylene, oxypropylene or oxybutylene units respectively or there may be present in the terminal block from 3 and up to 20 oxyalkylene units.
- the molecular weight of the polyoxyalkylene homopolymer or copolymer diamine that (1) is the source of the R' divalent radical of the polyamide according to formula (I) and (2) may be used to prepare the polyamide according to formula (I) may vary over a wide range it is preferred to use polyoxyalkylene homopolymer and copolymer diamines having an average molecular weight in the range of from about 72 to about 4000, more preferably in the range of from about 72 to 2000.
- the polyamide according to formula (I) has the terminal amine group or salt thereof bonded to a terminal secondary carbon atom (i.e. carbon atom having one hydrogen bonded thereto) of the divalent R' radical.
- organic amines usable in the practice of this invention for forming the amine salt of the terminal carboxylic acid group of the polyamide according to formula (I) there may be used an alkyl primary amine, alkyl secondary amine, alkyl tertiary amine and preferably a monoalkanol amine, dialkanol amine or trialkanol amine.
- Alkyl primary, secondary and tertiary amine salts of the carboxylic acid group having from 2 to 8 carbon atoms in the alkyl group of the amine may be used in the practice of this invention.
- the alkanol group contains from 2 to 8 carbon atoms and may be branched or unbranched in the practice of this invention.
- Organic amines which may also be used to form the amine salts of the terminal carboxylic acid group also include C 2 to C 6 alkylene diamines, poly(C 2 to C 4 oxyalkylene) diamines having a molecular weight of from about 200 to about 900, N-C 1 to C.sub.
- alkyl C 2 to C 6 alkylene diamine N,N'-di C 1 to C 8 alkyl C 2 to C 6 alkylene diamine, N,N,N'-tri C 1 to C 8 alkyl C 2 to C 6 alkylene diamine, N,N,N',N'-tetra C 1 to C 8 alkyl C 2 to C 6 alkylene diamine, N-alkanol C 2 to C 6 alkylene diamine, N,N'-dialkanol C 2 to C 6 alkylene diamine, N,N,N',N'-tetraalkanol C 2 to C 6 alkylene diamine and CH 3 CH 2 O(CH 2 CH 2 O) n CH 2 CH 2 CH 2 NH 2 wherein n is 1 or 2.
- Alkyl alkanol amines having from 2 to 8 carbon atoms in the alkyl and alkanol groups may also be used as the organic amine in the practice of this invention.
- alkyl amines which may be used to form the alkyl amine salts of the terminal carboxylic acid group of the polyamide according to formula (I), in the practice of this invention, include but are not limited to ethyl amine, butyl amine, propyl amine, isopropyl amine, secondary butyl amine, tertiary butyl amine, hexyl amine, isohexyl amine, n-octyl amine, 2-ethyl hexyl amine, diethyl amine, dipropyl amine, diisopropyl amine, dibutyl amine, ditertiary butyl amine, dihexyl amine, di n-octyl amine, di 2-ethyl hexyl amine, triethyl amine, tripropyl amine, triisopropyl amine, tributyl amine, tri-secondary butyl
- alkanol amines which may be used to make the alkanol amine salts of the terminal carboxyl group in the practice of this invention, there include, but not limited to, monoethanol amine, monobutanol amine, monopropanol amine, monoisopropanol amine, monoisobutanol amine, monohexanol amine, monooctanol amine, diethanol amine, dipropanol amine, diisopropanol amine, dibutanol amine, dihexanol amine, diisohexanol amine, dioctanol amine, triethanol amine, tripropanol amine, triisopropanol amine, tributanol amine, triisobutanol amine, trihexanol amine, triisohexanol amine, trioctanol amine and triisooctanol amine.
- amines such as methoxypropylamine, dimethyl aminopropyl amine, 1,3-propylene diamine, ethylene diamine, 3(2-ethoxyethoxy)propyl amine, N,N,N',N'-tetramethyl-1,3-butane diamine, monoethanol ethylene diamine, N,N'-diethanol ethylene diamine, N,N,N'N'-tetra hydroxymethyl ethylene diamine, N,N-diethyl ethanol amine and N-ethyl diethanol amine for preparing the organic amine salt of the terminal carboxylic acid group of the polyamide according to formula (I).
- amines such as methoxypropylamine, dimethyl aminopropyl amine, 1,3-propylene diamine, ethylene diamine, 3(2-ethoxyethoxy)propyl amine, N,N,N',N'-tetramethyl-1,3-butane diamine, monoethanol ethylene diamine, N,N'
- the organic amine salt of the terminal carboxylic acid group of the polyamide according to formula (I) may be prepared by methods well known in the art, such as, for example, by adding the organic amine to the polyamide according to formula (I) in the presence of an aqueous medium or conversely adding the polyamide according to formula (I) to the organic amine in the presence of an aqueous medium.
- the aqueous medium may be omitted or the aqueous medium may be replaced by an inert organic solvent medium.
- Alkali metal salts of the terminal carboxylic acid group of the polyamide according to formula (I), in the practice of the polyamide and aqueous functional fluid composition of this invention include for example the lithium, sodium, potassium, rubidium and cesium salts.
- the lithium, sodium and potassium salts are however preferred among the alkali metal salts of the terminal carboxylic acid group of the polyamide according to formula (I).
- Formation of the alkali metal salts of the terminal carboxylic acid group of the polyamide according to formula (I) may be accomplished by methods well known in the art such as, for example, by adding the polyamide according to formula (I) to the hydroxide of the alkali metal in the presence of an aqueous medium.
- the salts of the terminal amine group of the polyamide according to formula (I), i.e. the salt of the polyamide according to formula (I) formed by making the salt of the terminal amine group of said polyamide, in the practice of the polyamide and aqueous functional fluid composition of this invention may be the (a) quaternary ammonium salt of the terminal amine, formed by displacement of both of the amine hydrogens by organic (e.g. alkyl) groups, (b) inorganic acid salts (e.g. hydrogen chloride salt) (c) organic acid salts or (d) alkyl halide (e.g. methyl chloride) salt of the terminal amine group.
- Water soluble or dispersible intermolecular salts formed by the interaction of the terminal amine group of one polyamide molecule, according to this invention, with the terminal carboxylic acid group of another polyamide molecule, according to this invention, are also contemplated in the practice of the polyamide and aqueous functional fluid composition of this invention.
- polystyrene resin may be prepared according to formula (I) in the practice of the polyamide and aqueous functional fluid composition of this invention.
- an appropriate dicarboxylic acid may be reacted with a suitable polyoxyalkylene diamine under polymerizing conditions at 1:1 mole ratio in an inert organic medium with the continuous removal of the water formed during the reaction.
- the resulting polymer may then be isolated from the inert organic reaction medium by a method such as filtration or by evaporation of the organic medium.
- the reaction may be carried out (a) at room or elevated temperatures, (b) at atmospheric pressure or at pressures above or below atmospheric pressure, (c) with or without the use of a catalyst, (d) with or without the use of an inert atmosphere (e.g. nitrogen) and (e) in the absence of an inert reaction medium.
- the water soluble or dispersible polyamide according to formula (I) may be added to water.
- Another method would be to add a water soluble or dispersible salt of a water soluble or dispersible polyamide according to formula (I) to water.
- the water soluble or dispersible salt of the water insoluble polyamide according to formula (I) would be added to water.
- water could be added to the water soluble or dispersible polyamide according to formula (I), the water soluble or dispersible salt of a water soluble or dispersible polyamide according to formula (I) or the water soluble or dispersible salt of a water insoluble polyamide according to formula (I).
- a salt forming compound e.g. organic amine
- the water soluble or dispersible polyamide according to formula (I) may be added to water followed by the addition thereto of a salt forming compound (e.g. organic amine) in the preparation of the aqueous functional fluid composition of this invention.
- the concentration of the (a) water soluble or dispersible polyamide according to formula (I), (b) water soluble or dispersible salt of a water soluble or dispersible polyamide according to formula (I) or (c) water soluble or dispersible salt of a water insoluble polyamide according to formula (I) in the aqueous functional fluid composition of this invention may vary over a wide range, e.g. 0.01 to 99%, preferably 0.01 to 20%, more preferably 0.03 to 10%, by weight based on the total weight of the aqueous functional fluid composition. There may be present in the aqueous functional fluid composition of this invention from about 1% to about 99.99% by weight of water based on the total weight of said composition.
- additives well known in the art, including for example corrosion inhibitors, anti-foam agents, bacteriocides, fungicides, surfactants, extreme pressure agents, antioxidants and adjunct water soluble or dispersible lubricants, may be added to the aqueous functional fluid composition of this invention in conventional amounts.
- aqueous functional fluid composition of this invention comprising water and as a lubricant a water soluble or dispersible alkanol amine salt of a water soluble or dispersible polyamide according to formula (I) wherein R is a divalent radical residue derived by the removal of the carboxylic acid groups from a dimerized C 18 unsaturated fatty acid and R' is a divalent polyoxyalkylene chain having a terminal secondary carbon atom bonded to the terminal amine group of the polyamide.
- formula (I) wherein R is a divalent radical residue derived by the removal of the carboxylic acid groups from a dimerized C 18 unsaturated fatty acid and R' is a divalent polyoxyalkylene chain having a terminal secondary carbon atom bonded to the terminal amine group of the polyamide.
- polyamides are identified in the table below by means of the dicarboxylic acid and diamine reactants used in their preparation and by their molecular weight.
- the polyamides were prepared by conventional methods, two examples of which are as follows.
- Empol ® 1014 Dimer acid A polymerized fatty acid having a typical composition of 95% dimer acid (C 36 dibasic acid) approx. mol. wt. 565, 4% trimer acid (C 54 tribasic acid) approx. mol. wt. 845 and 1% monobasic acid (C 18 fatty acid) approx. mol. wt. 282 available from Emery industries, Inc.
- (e) Westvaco ® Diacid 1550 The Diels-Alder reaction product of tall oil and acrylic acid, said product refined to contain about 10% monoacids, available from the Westvaco Corp.
- Jeffamine ® D230 is a primary amine terminated polyoxypropylene diamine having an average molecular weight of about 230 and available from the Texaco Chemical Company.
- Jeffamine ® ED 600 is a diamine having an average molecular weight of about 600 available from the Texaco Chemical Company and being a primary amine terminated propylene oxide capped polyoxyethylene.
- Jeffamine ® ED900 is a diamine having an average molecular weight of about 900 available from the Texaco Chemical Company and being a primary amine terminated propylene oxide capped polyoxyethylene.
- (l) Jeffamine ® ED 2001 is a diamine having an average molecular weight of about 2000 available from the Texaco Chemical Company and being a primary amine terminated propylene oxide capped polyoxyethylene.
- Dow ® XA 1332 is a diamine obtained from the Dow Chemical Company and is a primary amine terminated propylene oxide capped 400 molecular weight polyoxyethylene.
- Dow ® XA 1333 is a diamine obtained from the Dow Chemical Company and is a primary amine terminated propylene oxide capped 600 molecular weight polyoxyethylene.
- a wedge-shaped high-speed tool is forced against the end of a rotating (88 surface feet per minute) SAE 1020 steel tube of 1/4 inch wall thickness.
- the feed force of the tool is sufficient to cut a V-groove in the tubing wall, and the chips flow out of the cutting area in two pieces (one piece from each face of the wedge-shaped tool).
- the forces on the tool as a result of workpiece rotation and of tool feed are measured by a tool post dynamometer connected to a Sanborn recorder. Any welding of chips to tool build-up is reflected in the interruption of chip-flow (visual) and in increased resistance to workpiece rotation.
- the cutting test is performed with the tool-chip interface flooded throughout the operation with circulating test fluid. Tool and workpiece are in constant dynamic contact during this time, and the test is not begun until full contact is achieved all along each cutting edge. The duration of the test is three minutes.
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Abstract
Description
______________________________________ Ex- Average am- Molecular ple weight of No. Dicarboxylic Acid Diamine polyamide ______________________________________ 1 Dimer Acid 3680 Jeffamine ED-900 1,600 2 Dimer Acid 3680 Jeffamine ED-900 2,700 3 Dimer Acid 3680 Jeffamine ED-900 4,000 4 Dimer Acid 3680 Jeffamine ED-900 5,400 5 Dimer Acid 3680 Jeffamine ED-900 18,000 6 Dimer Acid 3680 Jeffamine D-230 2,600 7 Dimer Acid 3680 Jeffamine D-400 2,800 8 Dimer Acid 3680 Jeffamine D-2000 12,000 9 Dimer Acid 3680 Jeffamine ED-600 3,900 10 Dimer Acid 3680 Jeffamine ED-2001 9,300 11 Dimer Acid 1014 Jeffamine ED-900 8,200 12 Dimer Acid 1014 Jeffamine ED-2001 19,000 13 Dimer Acid 1014 Jeffamine D-400 9,000 14 Dimer Acid 1014 Dow XA 1332 6,500 15 Dimer Acid 3675 CS Dow XA 1333 10,400 16 Diacid 1550 Jeffamine ED-900 3,600 17 Diacid 1550 Jeffamine ED-2001 5,700 18 Diacid 1550 Dow XA 1332 4,400 19 Diacid 1550 Dow XA 1333 3,900 20 Diacid 1525 Jeffamine ED-900 4,600 21 Diacid 1525 Jeffamine ED-2001 5,900 22 Diacid 1525 Jeffamine ED-600 3,700 23 Diacid 1525 Jeffamine D-400 2,800 24 Diacid 1525 Dow XA 1333 8,000 25 Dodecanedioic acid Jeffamine ED-900 5,700 26 DBD Jeffamine ED-600 2,600 27 Adipic Acid Jeffamine ED-600 4,300 28 Azelaic Acid Jeffamine ED-600 7,100 29 Azelaic Acid Jeffamine ED-900 4,600 30 Azelaic Acid Dow XA 1332 7,300 31 p-phenylene diacetic Jeffamine ED-600 3,600 Acid 32 2,5-pyridinedi- Jeffamine ED-2001 3,100 carboxylic Acid 33 Terephthalic Acid Jeffamine ED-900 5,000 34 Cyclohexane-1,4- Jeffamine ED-600 4,200 dicarboxylic Acid 35 Hexachloronorbornene Jeffamine ED-600 14,000 dicarboxylic Acid 36 Maleic Anhydride Jeffamine D-400 1,400 37 Fumaric Acid Jeffamine D-400 1,400 38 Fumaric Acid Jeffamine ED-900 3,200 39 Diglycolic Acid Jeffamine D-2000 5,100 40 Terephthalic Acid Jeffamine ED-600 2,100 41 Terephthalic Acid Jeffamine ED-400 2,800 42 Mesaconic Acid Jeffamine ED-900 8,300 ______________________________________
__________________________________________________________________________ Wt. of Wt. of Example Polyamide Polyamide Wt. (gm) of Water No. of Ex. No. (gm) NaOH KOH NH.sub.4 OH TEA.sup.○.sup.1 MIPA.sup.○.sup.2 DEA.sup.○.sup.3 (gm) __________________________________________________________________________ 43 1 15 15 470 44 1 15 10.6 474.4 45 2 15 15 470 46 2 15 7.5 477.5 47 3 15 15 470 48 3 15 5.6 479.4 49 4 15 15 470 50 4 15 5.6 479.4 51 5 15 15 470 52 6 15 15 470 53 6 15 4.0 481 54 7 15 15 470 55 7 15 5.6 479.4 56 8 15 15 470 57 8 15 7.5 477.5 58 9 0.6 0.6 498.8 59 9 1.5 1.5 497 60 9 6 6 488 61 9 15 15 470 62 9 60 60 380 63 10 15 15 470 64 10 15 3.5 481.5 65 11 15 15 470 66 12 15 15 470 67 13 15 15 470 68 14 15 15 470 69 15 15 15 470 70 16 15 15 470 71 16 15 5.6 479.4 72 17 15 15 470 73 17 15 485 74 17 15 4.0 481 75 18 15 15 470 76 19 15 15 470 77 20 15 15 470 78 20 15 485 79 21 15 15 470 80 21 15 3.5 481.5 81 22 15 15 470 82 22 15 4.0 481 83 23 15 15 470 84 23 15 7.5 477.5 85 24 15 15 470 86 25 15 15 470 87 25 15 5.6 479.4 88 26 15 15 470 89 26 15 7.5 477.5 90 26 15 10.6 474.4 91 27 15 15 470 92 27 15 485 93 27 15 5.6 479.4 94 28 15 15 470 95 28 15 10.6 474.4 96 29 15 15 470 97 29 15 3.5 481.5 98 30 15 15 470 99 31 15 15 470 100 31 15 10.6 474.4 101 32 15 15 470 102 32 15 4.0 481 103 33 15 15 470 104 33 15 4.0 481 105 34 15 15 470 106 35 15 15 470 107 36 15 15 470 108 37 15 15 470 109 38 15 15 470 110 39 15 15 470 111 40 15 15 470 112 41 15 15 470 113 42 15 15 470 __________________________________________________________________________ .sup.○.sup.1 triethanol amine .sup.○.sup.2 monoisopropanol amine .sup.○.sup.3 diethanol amine
______________________________________ Formulation of Force Example No. Example No. (lbs.) ______________________________________ 114 43 454 115 44 458 116 45 368 117 46 411 118 47 358 119 48 490 120 49 308 121 50 472 122 51 318 123 52 408 124 53 498 125 54 400 126 55 503 127 56 415 128 57 389 129 58 480 130 59 426 131 60 306 132 61 307 133 62 319 134 63 394 135 64 457 136 65 316 137 66 390 138 67 373 139 68 308 140 69 307 141 70 406 142 71 481 143 72 433 144 73 392 145 74 523 146 75 385 147 76 406 148 77 431 149 78 419 150 79 464 151 80 468 152 81 458 153 82 487 154 83 471 155 84 487 156 85 460 157 86 394 158 87 459 159 88 381 160 89 437 161 90 334 162 91 487 163 92 501 164 93 488 165 94 473 166 95 487 167 96 459 168 97 498 169 98 445 170 99 415 171 100 483 172 101 503 173 102 524 174 103 446 175 104 491 176 105 473 177 106 443 178 107 448 179 108 419 180 109 480 181 110 388 182 111 483 183 112 385 184 113 471 ______________________________________
Claims (32)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/481,494 USRE31522E (en) | 1981-07-21 | 1983-04-01 | Salt of a polyamide and functional fluid containing same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/285,575 US4374741A (en) | 1981-07-21 | 1981-07-21 | Polyamide and functional fluid containing same |
US06/481,494 USRE31522E (en) | 1981-07-21 | 1983-04-01 | Salt of a polyamide and functional fluid containing same |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/285,575 Reissue US4374741A (en) | 1981-07-21 | 1981-07-21 | Polyamide and functional fluid containing same |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE31522E true USRE31522E (en) | 1984-02-14 |
Family
ID=26963266
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/481,494 Expired - Lifetime USRE31522E (en) | 1981-07-21 | 1983-04-01 | Salt of a polyamide and functional fluid containing same |
Country Status (1)
Country | Link |
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US (1) | USRE31522E (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4659492A (en) | 1984-06-11 | 1987-04-21 | The Lubrizol Corporation | Alkenyl-substituted carboxylic acylating agent/hydroxy terminated polyoxyalkylene reaction products and aqueous systems containing same |
US4661275A (en) | 1985-07-29 | 1987-04-28 | The Lubrizol Corporation | Water-based functional fluid thickening combinations of surfactants and hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products |
US4743387A (en) | 1983-02-17 | 1988-05-10 | Mobil Oil Corporation | Polyoxyalkylene diamides as lubricant additives |
US4749500A (en) | 1985-07-29 | 1988-06-07 | The Lubrizol Corporation | Water-based functional fluid thickening combinations of surfactants and hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products |
US5128441A (en) * | 1987-07-27 | 1992-07-07 | Texaco Chemical Company | Block polyamido condensation products |
US5133889A (en) * | 1987-12-02 | 1992-07-28 | Institut Francais Du Petrole | Polysulfurized olefin compositions, their preparation and use as additives in lubricants |
US5239048A (en) * | 1987-07-27 | 1993-08-24 | Texaco Chemical Company | Aromatic polyoxyalkylene amidoamines |
US5260268A (en) * | 1991-07-18 | 1993-11-09 | The Lubrizol Corporation | Methods of drilling well boreholes and compositions used therein |
US5286395A (en) * | 1987-05-27 | 1994-02-15 | Institut Francais Du Petrole | Olefin polysulfide compositions of high sulfur content and very low chlorine content, their manufacture and use as additives for lubricants |
US5378798A (en) * | 1992-07-10 | 1995-01-03 | Shell Oil Company | Composition and process for coating metallic substrates |
US5599777A (en) * | 1993-10-06 | 1997-02-04 | The Lubrizol Corporation | Methods of using acidizing fluids in wells, and compositions used therein |
US20100152076A1 (en) * | 2004-12-03 | 2010-06-17 | Ab Skf | Lubricant and use of a lubricant |
US20180230272A1 (en) * | 2017-02-14 | 2018-08-16 | The Board Of Trustees Of The University Of Alabama | Ionic polyamide and polyamide-imide materials and methods of use |
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US4273664A (en) * | 1978-06-02 | 1981-06-16 | Snamprogetti S.P.A. | Rust-preventing agent for aqueous systems and rust-inhibiting lubricating compositions |
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Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4743387A (en) | 1983-02-17 | 1988-05-10 | Mobil Oil Corporation | Polyoxyalkylene diamides as lubricant additives |
US4659492A (en) | 1984-06-11 | 1987-04-21 | The Lubrizol Corporation | Alkenyl-substituted carboxylic acylating agent/hydroxy terminated polyoxyalkylene reaction products and aqueous systems containing same |
US4661275A (en) | 1985-07-29 | 1987-04-28 | The Lubrizol Corporation | Water-based functional fluid thickening combinations of surfactants and hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products |
US4749500A (en) | 1985-07-29 | 1988-06-07 | The Lubrizol Corporation | Water-based functional fluid thickening combinations of surfactants and hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products |
US5286395A (en) * | 1987-05-27 | 1994-02-15 | Institut Francais Du Petrole | Olefin polysulfide compositions of high sulfur content and very low chlorine content, their manufacture and use as additives for lubricants |
US5239048A (en) * | 1987-07-27 | 1993-08-24 | Texaco Chemical Company | Aromatic polyoxyalkylene amidoamines |
US5128441A (en) * | 1987-07-27 | 1992-07-07 | Texaco Chemical Company | Block polyamido condensation products |
US5133889A (en) * | 1987-12-02 | 1992-07-28 | Institut Francais Du Petrole | Polysulfurized olefin compositions, their preparation and use as additives in lubricants |
US5260268A (en) * | 1991-07-18 | 1993-11-09 | The Lubrizol Corporation | Methods of drilling well boreholes and compositions used therein |
US5378798A (en) * | 1992-07-10 | 1995-01-03 | Shell Oil Company | Composition and process for coating metallic substrates |
US5599777A (en) * | 1993-10-06 | 1997-02-04 | The Lubrizol Corporation | Methods of using acidizing fluids in wells, and compositions used therein |
US20100152076A1 (en) * | 2004-12-03 | 2010-06-17 | Ab Skf | Lubricant and use of a lubricant |
US8476204B2 (en) * | 2004-12-03 | 2013-07-02 | Ab Skf | Lubricant and use of a lubricant |
US20180230272A1 (en) * | 2017-02-14 | 2018-08-16 | The Board Of Trustees Of The University Of Alabama | Ionic polyamide and polyamide-imide materials and methods of use |
US10836865B2 (en) * | 2017-02-14 | 2020-11-17 | The Board Of Trustees Of The University Of Alabama | Ionic polyamide and polyamide-imide materials and methods of use |
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