EP0094144B1 - Sulfurized olefin-containing compositions - Google Patents

Sulfurized olefin-containing compositions Download PDF

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Publication number
EP0094144B1
EP0094144B1 EP83301521A EP83301521A EP0094144B1 EP 0094144 B1 EP0094144 B1 EP 0094144B1 EP 83301521 A EP83301521 A EP 83301521A EP 83301521 A EP83301521 A EP 83301521A EP 0094144 B1 EP0094144 B1 EP 0094144B1
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EP
European Patent Office
Prior art keywords
composition according
sulfur
acid
oil
component
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
Application number
EP83301521A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0094144A3 (en
EP0094144A2 (en
Inventor
Kirk Emerson C/O The Lubrizol Corporation Davis
James Noel C/O The Lubrizol Corporation Vinci
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lubrizol Corp
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Lubrizol Corp
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Publication date
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Publication of EP0094144A2 publication Critical patent/EP0094144A2/en
Publication of EP0094144A3 publication Critical patent/EP0094144A3/en
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Publication of EP0094144B1 publication Critical patent/EP0094144B1/en
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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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
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    • C10M127/00—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon
    • C10M127/02—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon well-defined aliphatic
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/40—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms monocarboxylic
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    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/44—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms containing hydroxy groups
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    • C10M129/68—Esters
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    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/26—Two-strokes or two-cycle engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines

Definitions

  • This invention relates to compositions useful as additives for lubricants, and, more particularly, for additives useful in multipurpose industrial oils for use in gear, hydraulic and other specialty applications.
  • the invention particularly relates to sulfurized olefin-containing compositions and lubricants and concentrates containing such compositions.
  • the invention provides a composition comprising:
  • compositions are useful as lubricant additive compositions, and more particularly, as additive compositions in industrial and gear lubricants.
  • the compositions when added to lubricants provide longer lasting extreme pressure properties and anti-wear capability and reduce staining of copper parts.
  • Component A also is a fatty acid ester, or mixture thereof.
  • fatty acid refers to acids which may be obtained by hydrolysis of naturally occurring vegetable or animal fats or oils. These fatty acids usually contain from 16 to 20 carbon atoms and are mixtures of saturated and unsaturated fatty acids. The unsaturated fatty acids generally contained in the naturally occurring vegetable or animal fats and oils may contain one or more double bonds and such acids include palmitoleic acid, oleic acid, linoleic acid, linolenic acid, petroselenic acid, erucic acid, gadoleic acid, vaccenic acid, ricinoleic acid and minor amounts of compounds containing more than 20 carbon atoms such as behenic acid.
  • the fatty acid esters which are useful as component A in the invention may be prepared from aliphatic olefinic acids of the type described above such as oleic acid, linoleic acid, linolenic acid, and behenic acid by reaction with alcohols and polyols.
  • aliphatic alcohols which may be reacted with the above- identified acids include monohydric alcohols such as methanol, ethanol, n-propanol, isopropanol, the butanols, etc.; and polyhydric alcohols including ethylene glycol, propylene glycol, trimethylene glycol, neopentyl glycol, glycerol, etc.
  • the unsaturated fatty acid ester useful component A may be derived from mixtures of acids such as those obtained from tall oil or by the hydrolysis of peanut oil, soybean oil, cottonseed oil, sunflower seed oil, or wheat germ oil.
  • Tall oil is a mixture of rosin acids, mainly abietic acid, ' and unsaturated fatty acids, mainly oleic and linoleic acids.
  • Tall oil is a by-product of the sulfate process for the manufacture of wood pulp.
  • esters for component (A) are the most particularly preferred are the fatty oils, that is, naturally occurring esters of glycerol with the fatty acids described above, and synthetic esters of similar structure.
  • naturally occurring fats and oils containing unsaturation include animal fats such as neat's-foot oil, lard oil, depot fat, beef tallow, etc.
  • naturally occurring vegetable oils useful as component A include cottonseed oil, corn oil, poppy-seed oil, safflower oil, sesame oil, soybean oil, sunflower seed oil and wheat germ oil.
  • Component B in the compositions of this invention is a sulfurization product of at least one of propylene, isobutene and their dimers, trimers and tetramers.
  • isobutene and diisobutene are particularly desirable because of their availability and the particularly high sulfur-containing compositions which can be prepared therefrom.
  • the sulfurizing reagent used for the preparation of component B may be, for example, sulfur, a sulfur halide such as sulfur monochloride or sulfur dichloride, a mixture of hydrogen sulfide and sulfur or sulfur dioxide, or the like.
  • sulfur-hydrogen sulfide mixtures are often preferred and are frequently referred to hereinafter; however, it will be understood that other sulfurization agents may, when appropriate, be substituted therefor.
  • the amounts of sulfur and hydrogen sulfide per mole of olefinic compound are, respectively, usually about 0.3-3.0 gram-atoms and about 0.1-1.5 moles.
  • the preferred ranges are about 0.5-2.0 gram-atoms and about 0.4-1.25 moles respectively, and the most desirable ranges are about 0.8-1.8 gram-atoms and about 0.4-0.8 mole respectively.
  • the temperature range in which the sulfurization reaction is carried out is generally about 50-350°C.
  • the preferred range is about 100-200°C, with about 125-180°C being especially suitable.
  • the reaction is often preferably conducted under superatmospheric pressure; this may be and usually is autogenous pressure (i.e., the pressure which naturally develops during the course of the reaction) but may also be externally applied pressure.
  • autogenous pressure i.e., the pressure which naturally develops during the course of the reaction
  • the exact pressure developed during the reaction is dependent upon such factors as the design and operation of the system, the reaction temperature, and the vapor pressure of the reactants and products and it may vary during the course of the reaction.
  • materials useful as sulfurization catalysts may be acidic, basic or neutral, but are preferably basic materials, especially nitrogen bases including ammonia and amines.
  • the amount of catalyst used is generally about 0.05-2.0% of the weight of the olefinic compound. In the case of the preferred ammonia and amine catalysts, about 0.0005-0.5 mole per mole of olefin is preferred, and about 0.001-0.1 mole is especially desirable.
  • a further optional step in the preparation of component B is the treatment of the sulfurized product, obtained as described hereinabove, to reduce active sulfur.
  • An illustrative method is treatment with an alkali metal sulfide as described in U.S. Patent 3,498,915.
  • Other optional treatments may be employed to remove insoluble by-products and improve such qualities as the odor, color and staining characteristics of the sulfurized compositions.
  • U.S. Patent 4,119,549 discloses suitable sulfurization products useful as component B. Several specific sulfurized compositions are described in the working examples thereof. The following example illustrates the preparation of one such composition.
  • Sulfur (629 parts, 19.6 moles) is charged to a jacketed high-pressure reactor which is fitted with an agitator and internal cooling coils. Refrigerated brine is circulated through the coils to cool the reactor prior to the introduction of the gaseous reactants. After sealing the reactor, evacuating to about 800 Pa (6 torr) and cooling, 1100 parts (19.6 moles) of isobutene, 334 parts (9.8 moles) of hydrogen sulfide and 7 parts of n-butylamine are charged to the reactor. The reactor is heated using steam in the external jacket, to a temperature of about 171°C over about 1.5 hours. A maximum pressure of 5 MPa (720 psig) is reached at about 138°C during this heat-up.
  • the pressure Prior to reaching the peak reaction temperature, the pressure starts to decrease and continues to decrease steadily as the gaseous reactants are consumed. After about 4.75 hours at about 171°C, the unreacted hydrogen sulfide and isobutene are vented to a recovery system..After the pressure in the reactor has decreased to atmospheric, the sulfurized mixture is recovered as a liquid.
  • the sulfurizing agent may be sulfur, and the reaction is effected by heating the olefinic compound with sulfur at a temperature of from 100-250°C, usually about 150-210°C with efficient agitation and in an inert atmosphere (e.g., nitrogen).
  • the weight ratio of olefin to sulfur may be as high as 15:1 and is generally between about 5:1 and 10:1.
  • reaction mixture consist entirely of the olefin and sulfur
  • reaction may be effected in the presence of an inert solvent such as alcohol, ether, ester, aliphatic hydrocarbon or halogenated aromatic hydrocarbon which is a liquid at the reaction temperatures employed.
  • insoluble by-products may be removed by filtration, usually at an elevated temperature (about 80-120°C).
  • the filtrate is the desired sulfurized product.
  • compositions of this invention contain components A and B in a weight ratio from about 0,2:1 to about 0.5:1.
  • the compositions of the invention may be prepared merely by blending the ingredients, either undiluted or in substantially inert diluents.
  • the diluent if any, may be the oil used as a lubricant base and may include other additives such as those described hereinafter.
  • compositions of this invention are illustrative of the compositions of this invention:
  • compositions of this invention are useful as additives for lubricants, in which they function primarily as extreme pressure and anti-wear agents; the addition of the compositions of the invention also results in a reduction in staining of copper parts.
  • lubricants based on diverse oils of lubricating viscosity, including natural and synthetic lubricating oils and mixtures thereof.
  • These lubricants include crankcase lubricating oils for spark-ignited and compression- ignited internal combustion engines, including automobile and truck engines, two-cycle engines, aviation piston engines, marine and railroad diesel engines, and the like. They can also be used in gas engines, stationary power engines and turbines and the like.
  • compositions of the present invention can also benefit from the incorporation therein of the compositions of the present invention.
  • the compositions are particularly useful in gear lubricants and especially industrial gear lubricants.
  • Natural oils include liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic and mixed paraffinic-naphthenic types. Oils of lubricating viscosity derived from coal or shale are also useful base oils.
  • Synthetic lubricating oils include hydrocarbon oils and halo- substituted hydrocarbon oils such as polymerized and interpolymerized olefins [e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(1-hexenes), poly(1- octenes), poly(1-decenes), etc.
  • alkylbenzenes e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)benzenes, etc.
  • polyphenyls e.g., biphenyls, terphenyls, alkylated polyphenyls, etc.
  • Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. constitute another class of known synthetic lubricating oils. These are exemplified by the oils prepared through polymerization of ethylene oxide or propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methylpolyisopropylene glycol ether having an average molecular weight of 1000, diphenyl ether of polyethylene glycol having a molecular weight of 500-1000, diethyl ether of polypropylene glycol having a molecular weight of 1000-1500, etc.) or mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C 3 -C e fatty acid esters, or the C 13 Oxo acid diester of tetraethylene glycol.
  • the oils prepared through polymerization of ethylene oxide or propylene oxide the alkyl and ary
  • Another suitable class of synthetic lubricating oils comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid; alkyl malonic acids, alkenyl malonic. acids, etc.) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol, etc.).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic
  • esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid, and the like.
  • Esters useful as synthetic oils also include those made from C.5 to C 12 monocarboxylic acids and polyols and polyol ethers such neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol, tripentaerythritol, etc.
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils comprise another useful class of synthetic lubricants [e.g., tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl) silicate, tetra-(4-methyl-2-ethylhexyl) silicate, tetra-(p-tert-butylphenyl) silicate, hexa-(4-methyl-2-pentoxy)-disiloxane, poly(methyl)-siloxanes, poly(methylphenyl)siloxanes, etc.].
  • synthetic lubricants e.g., tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl) silicate, tetra-(4
  • Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid, etc.), polymeric tetrahydrofurans and the like.
  • Unrefined, refined and rerefined oils (and mixtures of each with each other) of the type disclosed hereinabove can be used in the lubricant compositions of the present invention.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
  • a shale oil obtained directly from retorting operations a petroleum oil obtained directly from distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil.
  • Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties. Many such purification techniques are known to those of skill in the art such as solvent extraction, acid or base extraction, filtration, percolation, etc.
  • Rerefined oils are obtained by processes similar to those used to obtain refined oils applied to refined oils which have been already used in service. Such rerefined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques directed to removal of spent additives and oil breakdown products.
  • the lubricants of the present invention contain an amount of the composition of this invention sufficient to provide it with extreme pressure and anti-wear properties. Normally this amount will be about 0.01 to 10%, preferably about 0.01 to about 5% of the total weight of the lubricant. In lubricating oils operated under extremely adverse conditions, the reaction products of this invention may be present in amounts of up to about 20% by weight.
  • additives include, for example, detergents and dispersants of the ash-producing or ashless type, corrosion- and oxidation-inhibiting agents, pour point depressing agents, auxiliary extreme pressure agents, color stabilizers and anti-foam agents.
  • the ash-producing detergents are exemplified by oil-soluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids, or organic phosphorus acids characterized by at least one direct carbon-to-phosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g., polyisobutene having a molecular weight of 1000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride.
  • olefin polymer e.g., polyisobutene having a molecular weight of 1000
  • a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide,
  • basic salt is used to designate metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical.
  • the commonly employed methods for preparing the basic salts involve heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature above 50°C and filtering the resulting mass.
  • a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide
  • Examples of compounds useful as the promoter include phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol, and condensation products of formaldehyde with a phenolic substance; alcohols such as methanol, 2-propanol, octyl alcohol, cellosolve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol; and amines such as aniline, phenylenediamine, phenothiazine, phenyi-p-naphthyiamine, and doecylamine.
  • a particularly effective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent and at least one alcohol promoter, and carbonating the mixture at an elevated temperature such as 60-200°C.
  • Ashless detergents and dispersants are so called despite the fact that, depending on its constitution, the dispersant may upon combustion yield a non-volatile material such as boric oxide or phosphorus pentoxide; however, it does not ordinarily contain metal and therefore does not yield a metal-containing ash on combustion.
  • a non-volatile material such as boric oxide or phosphorus pentoxide
  • Many types are known in the art, and any of them are suitable for use in the lubricants of this invention. The following are illustrative:
  • chlorinated aliphatic hydrocarbons such as chlorinated wax
  • aromatic sulfides and polysulfides such as benzyl disulfide, bis(chlorobenzyl) disulfide, and sulfurized alkylphenol
  • phosphosulfurized hydrocarbons such as the reaction product of a phosphorus sulfide with turpentine or methyl oleate
  • phosphorus esters including principally dihydrocarbon and trihydrocarbon phosphites such as dibutyl phosphite, diheptyl phosphite, dicyclohexyl phosphite, pentylphenyl phosphite, dipentylphenyl phosphite, tridecyl phosphite, distearyl phosphite, dimethyl naphthyl phosphite, oley
  • compositions of this invention can be added directly to the lubricant.
  • they are diluted with a substantially inert, normally liquid organic diluent such as mineral oil, naphtha, benzene, toluene or xylene, to form an additive concentrate.
  • a substantially inert, normally liquid organic diluent such as mineral oil, naphtha, benzene, toluene or xylene
  • These concentrates usually contain about 20-90% by weight of the composition of this invention such as the compositions of Examples 1-6 and may contain, in addition, one or more other additives known in the art or described hereinabove.
  • Illustrative lubricants of this invention comprise principally mineral oil (e.g., SAE 10W-40 for an internal combustion engine lubricant and SAE 75W-90 for a gear lubricant) in combination with about 0.5-5.0% by weight or more of the composition of the invention such as Examples 1-4 and with other known lubricant additives.
  • principally mineral oil e.g., SAE 10W-40 for an internal combustion engine lubricant and SAE 75W-90 for a gear lubricant
  • Table II illustrate lubricating compositions according to the invention. Unless otherwise indicated, all amounts listed, except those for mineral oil, are exclusive of oil present as diluent.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
EP83301521A 1982-05-07 1983-03-18 Sulfurized olefin-containing compositions Expired - Lifetime EP0094144B1 (en)

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US37594882A 1982-05-07 1982-05-07
US375948 1982-05-07

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ZA862362B (en) * 1985-04-08 1987-11-25 Mobil Oil Corp Sulfurized olefins
GB8907474D0 (en) * 1989-04-03 1989-05-17 Ethyl Petroleum Additives Ltd Lubricant compositions
JP2927644B2 (ja) * 1993-07-02 1999-07-28 出光興産株式会社 金属加工油組成物
DE69732486T2 (de) * 1997-11-19 2005-07-07 Chevron Oronite Co. Llc, San Ramon Verwendung von Dithioethylen-Derivaten als Additiv zur Verbesserung der Kompatibilität mit den Fluorokohlenstoffelelastomeren
US7648948B2 (en) 2005-04-08 2010-01-19 Exxonmobil Chemical Patents Inc. Additive system for lubricants
JP2008094891A (ja) * 2006-10-06 2008-04-24 Idemitsu Kosan Co Ltd 潤滑用添加剤
US8841243B2 (en) * 2010-03-31 2014-09-23 Chevron Oronite Company Llc Natural gas engine lubricating oil compositions

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US2203507A (en) * 1937-12-11 1940-06-04 Socony Vacuum Oil Co Inc Lubricant and method of lubrication
US2851422A (en) * 1952-11-07 1958-09-09 Pure Oil Co Automatic transmission fluid
US2830956A (en) * 1954-02-12 1958-04-15 Exxon Research Engineering Co Hydraulic power transmission fluids
US3267033A (en) * 1963-04-15 1966-08-16 Lubrizol Corp Lubricating composition having desirable frictional characteristics
US3574101A (en) * 1968-04-29 1971-04-06 Lubrizol Corp Acylating agents,their salts,and lubricants and fuels containing the same
JPS4945769A (en) * 1972-09-04 1974-05-01 Seiko Instr & Electronics Udedokeikeesu no kozo
CA1064463A (en) * 1975-03-21 1979-10-16 Kirk E. Davis Sulfurized compositions
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JPS5767693A (en) * 1980-10-15 1982-04-24 Mitsubishi Oil Co Ltd Lubricant composition
US4416788A (en) * 1981-10-13 1983-11-22 Atlantic Richfield Company Metal cutting oil and method for using same

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EP0094144A3 (en) 1985-08-14
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SG37191G (en) 1991-06-21
MX9100403A (es) 1992-11-01
EP0094144A2 (en) 1983-11-16
HK44391A (en) 1991-06-14
MX167094B (es) 1993-03-03
JPS5915490A (ja) 1984-01-26
DE3382057D1 (de) 1991-01-24
CA1208208A (en) 1986-07-22

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