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  • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
  • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
  • C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
  • C10M145/14—Acrylate; Methacrylate
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  • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
  • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M149/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
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  • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M149/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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  • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
  • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M149/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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  • C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
  • C10M151/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
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  • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
  • C10M2201/02—Water
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
  • C10M2207/046—Hydroxy ethers
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/18—Tall oil acids
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/084—Acrylate; Methacrylate
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  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
  • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/12—Partial amides of polycarboxylic acids
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  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/22—Heterocyclic nitrogen compounds
  • C10M2215/221—Six-membered rings containing nitrogen and carbon only
  • C10M2215/222—Triazines
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  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
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  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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  • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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  • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
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  • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
  • C10M2229/04—Siloxanes with specific structure
  • C10M2229/045—Siloxanes with specific structure containing silicon-to-hydroxyl bonds
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  • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
  • C10M2229/04—Siloxanes with specific structure
  • C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon bonds
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  • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
  • C10M2229/04—Siloxanes with specific structure
  • C10M2229/047—Siloxanes with specific structure containing alkylene oxide groups
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  • C10M2229/04—Siloxanes with specific structure
  • C10M2229/048—Siloxanes with specific structure containing carboxyl groups
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  • 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
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  • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
  • C10N2050/01—Emulsions, colloids, or micelles
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  • C10N2070/00—Specific manufacturing methods for lubricant compositions
  • C10N2070/02—Concentrating of additives

Definitions

• the present invention relates to the use of polymers containing structural units of acrylamide and of acrylamidosulfonic acids for suppressing the misting of water-based cooling lubricants.
• cooling lubricants are generally used to reduce tool wear. These can be swirled into the environment during the high speeds of the tool or workpiece occurring, for example, when cutting or grinding metals, as a result of which undesired mist formation occurs.
• the prior art knows various approaches to reduce this misting (antimisting).
• EP-A-0 811 677 discloses water-based metalworking fluids containing antimisting copolymers. These copolymers consist on the one hand of structural units which are derived either from acrylamidosulphonic acids or from sulphonated styrene, on the other hand from structural units of acrylamides or acrylic esters.
• EP-B-0 642 571 discloses the use of polymers having a molecular weight greater than 1,000,000 units as an antimisting additive, wherein the polymers are selected from the group of polyalkylene oxides, polyacrylamides, polymethacrylamides or acrylamide / methacrylamide / unsaturated carboxylic acid copolymers.
• GB-A-22 52 103 discloses polymers as antimisting additive, which are composed of structural units derived from water-soluble acrylamides, acrylic acid and water-insoluble acrylamides.
• EP-A-0 311 799 discloses thickeners for aqueous media containing a water-soluble polymer having hydrophobic groups, for example an acrylamide / dodecyl acrylate / acrylic acid terpolymer.
• WO 99/66004 is a document under Article 54 (3) EPC and generally relates to aqueous compositions containing water-soluble or water-dispersible copolymers of hydrophobic and hydrophilic comonomers.
• Example 11 describes the preparation of a terpolymer from tert-butylacrylamide, 2-amido-2-methylpropanesulfonic acid sodium salt and acrylamide.
• U.S. 4,563,294 discloses a hydrous saw chain lubricant consisting essentially of water and a water-soluble antifreeze as major constituents and corrosion inhibitors. Wear inhibitors and adhesion promoters in an effective amount, wherein the adhesion promoter is a water-soluble polyethylene glycol and / or a sulfonic acid groups and water-soluble acrylamide copolymer having a molecular weight of at least 500,000.
• this coupling agent which is present in an amount of from 0.05 to 1% by weight, it contains from 5 to 50% by weight of a water-soluble polyethylene oxide-polypropylene oxide adduct having a viscosity of at least 300 mPas at 50 ° C special lubricant. Percentages by weight, based in each case on the weight of the composition.
• Additives for the reduction of fogging in metalworking are an important tool for reasons of health protection of persons entrusted with such work. Such additives are therefore the subject of intensive research and development work.
• the object of the present invention is to provide additives having improved properties.
• the copolymer thus defined is also referred to below as an antimisting additive.
• the term "derived from” here means that the stated olefinically unsaturated compounds react with loss of at least one C-C double bond and thus the copolymer contains corresponding structural units.
• R 1 is preferably hydrogen.
• R 2 in a preferred embodiment is an alkylene radical of the formula 3.
• the structural unit of the formula 2 is preferably prepared by the copolymerization of acrylamidopropenylsulfonic acid (AMPS).
• AMPS acrylamidopropenylsulfonic acid
• Preferred molecular weights (number average) of the copolymers are between 100,000 and 2,000,000, in particular 250,000 to 1,000,000 units.
• the relative viscosity or the k value serve as an indicator of the molecular weight.
• the copolymer is dissolved in a certain concentration (usually 0.5%) and determined by means of Ubbelohde capillary viscometer, the outflow time at 25 ° C. This value gives the absolute viscosity of the solution ( ⁇ c ).
• the absolute viscosity of the solvent is ⁇ o .
• the molar amounts of the structural units of the formulas 1 and 2 complement each other in a preferred embodiment to 100 wt .-%.
• the copolymer contains from 2 to 50% by weight of the structural units derived from formula 1. Furthermore, the copolymer preferably contains from 50 to 98% by weight of structural units of the formula 2, in particular from 20 to 35% by weight of structural units of the formula I and from 65 to 80% by weight of the structural units of the formula 2.
• the copolymer may contain further comonomers.
• the copolymer contains structural units derived from compounds of formulas 4 and / or 5,
• R 3 and R 4 are H or C 1 -C 4 alkyl. Furthermore, R 3 and R 4 can form a ring with 5, 6, 7 or 8 ring atoms including the -N-CO- group. Preference is given to rings with 5, 6 or 7 ring atoms. R 3 and R 4 may comprise heteroatoms, preferably they comprise only carbon atoms. In a particularly preferred embodiment, formula 4 is a structural unit of the formula 4a.
• formula 4 is N-vinylcaprolactam. In a further particularly preferred embodiment, it is a structural unit of the formula 4b.
• R 5 and R 6 independently of one another denote a terminally unsaturated alkenyl radical having 3 to 5 C atoms.
• R 7 and R 8 independently of one another are C 1 -C 4 -alkyl.
• X is an anion.
• R 5 and R 6 are preferably both an allyl radical.
• the proportion of structural units of the formulas (4) and (5) on the copolymer is independently up to 20 wt .-%, preferably independently from 10 to 20 wt .-%.
• the copolymer contains 5 to 20 wt .-% of structural units derived from the acrylic acid.
• copolymers according to the invention can be prepared by copolymerization of compounds of the formulas (1) and (2) and, if appropriate, (4) and / or (5).
• the process for preparing the copolymers is described in the prior art and is set forth below.
• the copolymers can be prepared by the methods of solution polymerization, bulk polymerization, emulsion polymerization, inverse emulsion polymerization, precipitation polymerization or gel polymerization.
• the polymerization is carried out as a solution polymerization in water or as a precipitation polymerization.
• a water-miscible organic solvent is generally carried out under the conditions of precipitation polymerization. In this case, the polymer falls directly in solid form and can be isolated by distilling off the solvent or suction and drying.
• Suitable water-miscible organic solvents which are suitable for carrying out this preparation process are, in particular, water-soluble Alkanols, namely those having 1 to 4 carbon atoms such as methanol, ethanol, propanol, isopropanol, n-, sec- and iso-butanol, but preferably tert-butanol, into consideration.
• the water content of the lower alkanols used as solvent should not exceed 6% by weight, since otherwise lumping may occur during the polymerization.
• work is carried out at a water content of 0 to 3 wt .-%.
• the amount of solvent to be used depends to some extent on the nature of the comonomers used. As a rule, 200 to 1,000 g of the solvent are used per 100 g of total monomers.
• the aqueous monomer solution in a known manner in a water-immiscible organic solvent such as cyclohexane, toluene, xylene, heptane or high-boiling gasoline fractions with the addition of 0.5 to 8 wt .-%, preferably 1 to 4 wt .-% emulsified known emulsifiers of the W / O type and polymerized with conventional radical-forming initiators.
• a water-immiscible organic solvent such as cyclohexane, toluene, xylene, heptane or high-boiling gasoline fractions
• a water-immiscible organic solvent such as cyclohexane, toluene, xylene, heptane or high-boiling gasoline fractions
• a water-immiscible organic solvent such as cyclohexane, toluene, xylene, h
• the comonomers to be used may be emulsified as such in the water-immiscible organic solvent, or they may be used in the form of an aqueous solution containing between 100 and 5% by weight of comonomers and 0 to 95% by weight of water. wherein the composition of the aqueous solution is a matter of the solubility of the comonomers in water and the intended polymerization temperature.
• the ratio between water and the monomer phase is variable within wide limits and is usually at 70:30 to 30:70.
• a water-in-oil emulsifier In order to emulsify the monomers in the water-immiscible organic solvent to a water-in-oil emulsion, 0.1 to 10 wt .-%, based on the oil phase, of a water-in-oil emulsifier are added to the mixtures , Preferably, those emulsifiers are used which have a relatively low HLB value.
• the HLB value is a measure of the hydrophobicity and hydrophilicity of surfactants and emulsifiers (Griffin, J. Soc. Cosmetic Chemists 1, (1950), 311). Low HLB substances, below about 10, are generally good water-in-oil emulsifiers.
• any inert water-insoluble liquid i. any hydrophobic organic solvent can be used.
• hydrocarbons are used here whose boiling point is in the range from 120 to 350.degree. These hydrocarbons may be saturated, linear or branched paraffinic hydrocarbons, as predominantly present in petroleum fractions, which may also contain the usual proportions of naphthenic hydrocarbons.
• aromatic hydrocarbons such as, for example, toluene or xylene, and the mixtures of the abovementioned hydrocarbons as the oil phase.
• a mixture of saturated normal and iso-paraffinic hydrocarbons containing up to 20% by weight of naphthenes is used.
• a detailed description of the process can be found, for example, in DE-A-1 089 173 and in US-3,284,393 and 3,624,019.
• Copolymers having molecular weights of more than 1,000,000 are obtained when the polymerization is carried out in aqueous solution by the so-called gel polymerization method. 15-60% strength by weight solutions of the comonomers are polymerized with known suitable catalysts without mechanical thorough mixing using the Trommsdorff-Norrish effect (Bios Final Rep., 363, 22; Macromol. Chem., 1, 169/1947).
• copolymers prepared in this way in the form of aqueous jellies, can be dissolved directly in water after mechanical comminution with suitable apparatus and used. However, they can also be obtained after removal of the water by known drying processes in solid form and only when they are used again dissolved in water.
• the polymerization reactions are carried out in the temperature range between -60 and 200 ° C, preferably between 10 and 120 ° C, which can be carried out both under atmospheric pressure and under elevated pressure.
• the polymerization is carried out in a protective gas atmosphere, preferably under nitrogen.
• high-energy electromagnetic or corpuscular radiation or the usual chemical polymerization initiators can be used, for.
• organic peroxides such as benzoyl peroxide, tert. Butyl hydroperoxide, methyl ethyl ketone peroxide, cumene hydroperoxide, azo compounds such as azobisisobutyronitrile or 2'-azobis (2-amidinopropane) dihydrochloride and inorganic peroxy compounds such as (NH 4 ) 2 S 2 O 8 or K 2 S 2 O 8 or H 2 O 2 if necessary .
• reducing agents such as sodium bisulfite and ferrous sulfate or redox systems which as the reducing component of an aliphatic or aromatic sulfinic acid such as benzenesulfinic acid and toluenesulfinic acid or derivatives of these acids, such as.
• reducing agents such as sodium bisulfite and ferrous sulfate or redox systems which as the reducing component of an aliphatic or aromatic sulfinic acid such as benzenesulfinic acid and toluenesulfinic acid or derivatives of these acids, such as.
• moderators are added to the polymerization batches, which harmonize the course of the reaction by flattening the reaction rate-time diagram. They thus lead to an improvement in the reproducibility of the reaction and thus make it possible to produce uniform products with a narrow molar mass distribution and a high chain length.
• suitable moderators of this type are nitrilo-tris-propionylamide or monoalkylamines, dialkylamines or trialkylamines such as dibutylamine.
• moderators can be used with advantage.
• so-called regulators can be added to the polymerization batches which adjust the molecular weight of the polymers produced by a targeted chain termination.
• Useful known regulators are, for example, alcohols such as methanol, ethanol, propanol, isopropanol, n-butanol and amyl alcohols, alkyl mercaptans such as dodecyl mercaptan and tert. dodecyl, Isooctyl thioglycolate and some halogen compounds such as carbon tetrachloride, chloroform and methylene chloride.
• the copolymers are added to water-based cooling lubricants in amounts of 0.01 to 2, preferably 0.1 to 0.5 wt .-%, based on the finished formulated cooling lubricant.
• the composition of the water-based cooling lubricants can be very different.
• such coolants often contain natural paraffinic, naphthenic or paraffinic-naphthenic mineral oils, among other additives.
• such cooling lubricants of ester oils, fatty oil derivatives, synthetic hydrocarbons, poly- ⁇ -olefins such.
• polyisobutenes or polybutenes polypropylene glycol, trimethylolpropane, neopentyl glycol, pentaerythritol, di (2-ethylhexyl) sebacate, di- (2-ethylhexyl) adipate, dibutyl phthalate and / or esters of phosphorus-containing acids.
• cooling lubricants are aqueous solutions of inorganic salts such as phosphates, borates, carbonates and organic rust inhibitors such as amines, alkanolamines and substituted alkanolamines, as well as their reaction products with inorganic and organic acids.
• inorganic salts such as phosphates, borates, carbonates and organic rust inhibitors
• organic rust inhibitors such as amines, alkanolamines and substituted alkanolamines, as well as their reaction products with inorganic and organic acids.
• Such acids include, for example, natural or synthetic carboxylic acids such as caprylic acid, ethylhexanoic acid, capric acid, 2,2,4-trimethylhexanoic acid, benzoic acid, substituted benzoic acids, dicarboxylic acids having 6-22 carbon atoms, phosphoric acid esters, bicarboxylic acid half-esters or dicarboxylic acid halfbamides, citric acid, gluconic acid, carbonic acid, phosphoric acid , Polyphosphoric acids, boric acid.
• cooling lubricants often contain water-soluble lubricants such as glycols and polyglycols and ethers or esters of polyglycols and other additives to adjust the desired properties.
• base materials which make up the majority of coolants, may be other functional additives such as lubricity additives, antiwear agents, corrosion inhibitors, antioxidants, anionic or nonionic emulsifiers, solubilizers, anti-foaming agents, biocides, and / or surfactants.
• lubricity additives such as lubricity additives, antiwear agents, corrosion inhibitors, antioxidants, anionic or nonionic emulsifiers, solubilizers, anti-foaming agents, biocides, and / or surfactants.
• the abovementioned basic substances, the copolymers defined here and optionally functional additives are mixed with water.
• compositions 1, 2 and 3 can still be added a polyalkylene glycol in an amount of 5 to 20 wt .-%.
• This is an EO / PO block or copolymer which has lubricating properties.
• the device comprises a container with a height of 15 cm and a diameter of 9 cm.
• the coolant to be tested is filled.
• a gas stream generally air
• the strength of the gas flow is controlled by means of a flow meter.
• the frit, through which the gas flow is injected into the container, is located about 1 cm above the container bottom. 1 cm above the frit is a disperser (Ultra Turrax T 25). If gas flows via the frit into the cooling lubricant, a mist of cooling lubricant is produced when the disperser is switched on above the liquid surface.
• the presence of this fog is provided by 2 halogen spotlights made visible, whose light rays extend over the liquid surface so that an observation of the scattering caused by the fog is possible.
• Cooling lubricant concentrates of the following composition are used (data in% by weight). Coolant concentrate K1 6% Genapol ® 0-050 (C 16 / C 18 fatty alcohol polyglycol ethers having 5 EO) 49.5% Hostacor ® 4154 (Alkenylbernsteinklat) 3% tall oil fatty acid 37% Gravex Shell ® (mineral oil) 4% VE water 0.5% Foam Ban MS ® 455-3A (polyglycol-siloxane EntFiurner) 30% Hostacor IT ® (compound of formula (8) neutralized with triethanolamine) 17% triethanolamine 1 % Genapol ® PF 10 (EO-PO-block polymer) 4% diglycol 48% VE water 45% Hostacor ® IT 17% triethanolamine 9% Genapol ® B (EO-PO-block polymer) 1 % Genapol ® PN 30 (EO-PO-block polymer) 5% diglycol 23% VE water
• composition of the copolymers (% by weight)
• the k value was determined according to Fikentscher, Cellulose Chemistry, 13, (1932), 58.
• copolymers of the invention increase the viscosity of the additized with them cooling lubricants not or only slightly. They have no influence on their tendency to foam, anti-corrosion properties or lubricating effect.
• the shear stability of the additized cooling lubricants was tested by shearing them in the Ultraturrax at 10,000 rpm for about 10 minutes with cooling. After shearing, the antimisting effect is fully retained, indicating that the polymers do not decompose under shear.
• cooling lubricants with the copolymers according to the invention can be carried out either with the concentrate or with the finished formulated cooling lubricant. While the final formulated coolant is always based on water, the concentrate may also be present as an oil-based substance in which the copolymers are not soluble. Only in this case, the copolymers of the invention must be incorporated into the already water-diluted coolant.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Chemistry (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Lubricants (AREA)

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• 1999
  • 1999-07-06 DE DE19931220A patent/DE19931220B4/de not_active Expired - Fee Related
• 2000
  • 2000-06-21 ES ES00113201T patent/ES2282070T3/es not_active Expired - Lifetime
  • 2000-06-21 DE DE50014078T patent/DE50014078D1/de not_active Expired - Fee Related
  • 2000-06-21 EP EP00113201A patent/EP1067168B1/de not_active Expired - Lifetime
  • 2000-07-05 JP JP2000203895A patent/JP2001055597A/ja not_active Withdrawn
  • 2000-07-05 CA CA002313570A patent/CA2313570A1/en not_active Abandoned
  • 2000-07-06 US US09/611,016 patent/US6414075B1/en not_active Expired - Fee Related

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