Heavy Metal Or Aluminum Containing Catalyst Patents (Class 568/789)
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Patent number: 8937201Abstract: This invention relates to processes for producing various t-butyl phenols, such as 2,6-di-tert-butyl phenol and ortho-tert-butyl phenol, by selectively reacting phenol or a substituted phenol with an isobutylene-containing C4 raffinate stream. The 2,6-di-tert-butyl phenol and ortho-tert-butyl phenol can be transalkylated to form other tert-butyl phenols, such as para-tert-butyl phenol, 2,4-di-tert-butyl phenol.Type: GrantFiled: December 3, 2010Date of Patent: January 20, 2015Assignee: SI Group, Inc.Inventors: Roger D'Souza, Scott Smith, Kirthivasan Nagarajan
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Publication number: 20130150629Abstract: This invention relates to processes for producing various t-butyl phenols, such as 2,6-di-ten-butyl phenol and ortho-tert-butyl phenol, by selectively reacting phenol or a substituted phenol with an isobutylene-containing C4 raffinate stream. The 2,6-di-ten-butyl phenol and ortho-tert-butyl phenol can be transalkylated to form other ten-butyl phenols, such as para-tert-butyl phenol, 2,4-di-ten-butyl phenol.Type: ApplicationFiled: December 3, 2010Publication date: June 13, 2013Applicant: SI GROUP, INC.Inventors: Roger D'Souza, Scott Smith, Kirthivasan Nagarajan
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Patent number: 7692047Abstract: The present invention relates to an improved process for the selective alkylation of phenols using heteropolyacid catalyst supported onto zirconia under mild conditions. The process is economically viable since the catalyst regenerated after the initial reaction on further use gives the product in high yield.Type: GrantFiled: September 26, 2007Date of Patent: April 6, 2010Assignee: Secretary, Department of Science & TechnologyInventors: Anjali Uday Patel, Nikunj Bhagwatiprasad Bhatt
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Patent number: 7288683Abstract: An alkylation method comprises reacting a hydroxy aromatic compound with an alkyl alcohol in the presence of an alkylation catalyst comprising a metal oxide wherein the alkylation catalyst, has a surface area to volume ratio of about 950 to about 4,000 m2/m3, an aspect ratio of about 0.7 to about 1.0 or a combination of the foregoing.Type: GrantFiled: June 16, 2006Date of Patent: October 30, 2007Assignee: General Electric CompanyInventors: Hugo G. E. Ingelbrecht, David Parrillo, Mukund Parthasarathy, Gert-Jan Schoenmakers, Geuch Zijlma
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Patent number: 7282617Abstract: A process for making medium and long chain alkylaromatics and alkylphenols having a high level of anti-Markovnikov addition of the alkyl group. The alkylaromatics and alkylphenols made by the process of the present invention have enhanced stability and are particularly well suited to make highly stable oil additives and enhanced oil recovery surfactants.Type: GrantFiled: March 31, 2006Date of Patent: October 16, 2007Assignee: Chevron U.S.A. Inc.Inventors: William L. Schinski, Curt B. Campbell
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Patent number: 6846962Abstract: In a method for the production of o-alkyl phenols by conversion of phenol with an alkanol at elevated temperature in the gas phase in the presence of a metal catalyst, the conversion takes place in at least two stages wherein the alkanol/phenol molar ratio in each reaction stage is set to a value of approximately ?0.4; a clear increase in the selectivity for the o-alkyl phenol is obtained.Type: GrantFiled: November 15, 2002Date of Patent: January 25, 2005Assignee: Rutgers Chemicals AGInventors: Jörg Talbiersky, Edgar Fuhrmann, Wolfgang Brüggemann
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Patent number: 6232485Abstract: A process for the production of liquid meta-rich triaryl phosphate esters having low triphenyl phosphate content and low viscosity comprises (a) an alkylation stage wherein a phenol is reacted with an olefin having 2 to 12 carbon atoms in the presence of a strong acid catalyst to give a reaction product comprising a mixture of meta and para alkylated phenols; and (b) a transalkylation stage wherein the mixture of alkylated phenols from the alkylation stage is heated in the presence of a strong acid catalyst to increase the meta isomer content of the mixture to at least 25% whilst maintaining a phenol level below 22%; and (c) a phosphorylation stage wherein the mixture of alkylated phenols from the transalkylation stage is reacted with a phosphorylating agent; and wherein the strong acid catalyst used in stages (a) and (b) is a Bronsted acid having an acid strength of less than zero. Preferred catalysts are activated clays such as bentonite, montmorillonite or Fullers Earth clay.Type: GrantFiled: November 26, 1999Date of Patent: May 15, 2001Assignee: Great Lakes Chemical CorporationInventors: Tracy Anne Derbyshire, Hazel May Farrow, Jonathan Simon Hill
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Patent number: 5288927Abstract: There is provided a process for reacting phenol with butene or butanol over fairly large-pore zeolites to give butylphenol with high para-selectivity. Particular zeolites for use in this reaction include ZSM-12 and zeolite beta. A particular butene or butanol reactant is isobutanol. The product of this reaction may have a high content of the mono-alkylated, tert-butyl product.Type: GrantFiled: February 1, 1993Date of Patent: February 22, 1994Assignee: Mobil Oil Corp.Inventors: Clarence D. Chang, Stuart D. Hellring
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Patent number: 5245089Abstract: Provided is a process for alkylating aromatic compounds in the presence of mixed oxides of titanium and gallium which have been found to be highly active catalysts for the alkylation of aromatics with alkyl esters, alcohols, olefins and ethers. When the alkyl acceptor is a phenol, the catalysts provide high reaction rates and high selectivity for ortho alkylated products.Type: GrantFiled: October 23, 1992Date of Patent: September 14, 1993Assignee: Eastman Kodak CompanyInventors: Gether Irick, Jr., Leslie S. LaForce
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Patent number: 5175375Abstract: The invention relates to producing ortho isopropyl phenol catalytically by contacting phenol with isopropanol or propylene, at a temperature of from about 200.degree. C. to about 300.degree. C., with ZSM-12 and zeolite Beta; and recovering ortho isopropyl phenol.Type: GrantFiled: October 11, 1991Date of Patent: December 29, 1992Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Stuart D. Hellring
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Patent number: 5144082Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support. Particularly disclosed are the alkylphenols prepared by the process of alkylation a phenol at the aromatic nucleus with the novel oligomer.Type: GrantFiled: April 17, 1991Date of Patent: September 1, 1992Assignee: Mobil Oil CorporationInventors: Thomas R. Forbus, Bruce P. Pelrine
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Patent number: 5099076Abstract: The present invention is directed to a method for the preparation of p,p'-biphenol by simplified processes achieved by batch or continuous operations which comprises using phenol and isobutylene as starting materials, allowing phenol to react with isobutylene in the presence of aluminum phenoxide, oxidizing the resulting reaction liquid in the presence of an alkaline catalyst, and debutylating the reaction liquid in the presence of a debutylation catalyst.Type: GrantFiled: October 5, 1990Date of Patent: March 24, 1992Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Katsunori Takahashi, Mikio Kawahara, Shunji Yago, Yoshiharu Ayabe
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Patent number: 5091594Abstract: For producing 2,6-di-tert-butylphenol and products therefrom, utilizing small quantities of aluminum tris-(2-tert-butylphenolate as a catalyst by reaction of 2-tert-butylphenol with isobutene in the liquid phase, the reaction is performed in the presence of diluents such as liquid saturated aliphatic or cycloaliphatic hydrocarbons, C.sub.5 -C.sub.16 alkenes of formula R.sub.1 --CH.dbd.CH.sub.2 or R.sub.2 --CH.dbd.CH--R.sub.3, C.sub.5 to C.sub.12 cycloalkenes, which contain no branching on the C.dbd.C-bond, excess isobutene or mixtures thereof, at temperatures of 0.degree. C. to 80.degree. C., pressures of 0.1 to 11 bars and catalyst amounts of 0.005 to 5 mol %, based on 2-tert-butylphenol. High conversions are obtained with few undesirable trialkylated products.Type: GrantFiled: December 11, 1990Date of Patent: February 25, 1992Assignee: Huels AktiengesellschaftInventors: Friedrich-Wilhelm Kupper, Wolfgang H. E. Muller, Alfred Oberholz
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Patent number: 4870216Abstract: Phenols are selectively orthoalkylated in higher yields by the reverse addition of a phenol-aluminum phenoxide mixture to an olefin at alkylation temperature and under pressure sufficient to maintain a liquid olefin phase.Type: GrantFiled: June 24, 1988Date of Patent: September 26, 1989Assignee: Ethyl CorporationInventors: Jeffrey F. King, Charles W. Matthews, Eric S. Batman
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Patent number: 4870215Abstract: Phenol is di-orthoalkylated in high yield by reacting, in a first stage, phenol containing only 1 mole of an aluminum phenoxide for each 100-800 moles of phenol with an olefin at 85.degree.-175.degree. C. until the reaction mixture contains 3 wt percent or less phenol and then, in a second stage, continuing the reaction at 25.degree.-80.degree. C. until the mixture contains a substantial amount of 2,6-di-alkylphenol.Type: GrantFiled: June 24, 1988Date of Patent: September 26, 1989Assignee: Ethyl CorporationInventors: Steven L. Wiker, Charles W Matthews, Jeffrey F. King
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Patent number: 4709102Abstract: The production of a 2-lower alkyl phenol, e.g., 2-cresol or 2-ethylphenol, is carried out by transalkylation of a lower alkyl phenyl ether, e.g. anisole or phenetole, at an elevated temperature in the presence of a medium pore, pentasil-type molecular sieve, e.g. an H-ZSM-5 zeolite, a silicalite or an AMS-1B borosilicate, as catalyst.Type: GrantFiled: October 7, 1986Date of Patent: November 24, 1987Assignee: Celanese CorporationInventor: Balaram B. G. Gupta
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Patent number: 4665238Abstract: Alkylaromatic compounds may be synthesized by reacting an aromatic compound with an alkylating agent comprising a mixture of gases, including carbon monoxide and hydrogen at alkylation conditions in the presence of a dual-function-catalyst. The catalyst system which is employed for this reaction will comprise (1) a composite of oxides of copper and chromium and (2) an aluminosilicate which may be either in crystalline or amorphous form.Type: GrantFiled: September 9, 1985Date of Patent: May 12, 1987Assignee: UOP Inc.Inventors: Tamotsu Imai, Paul T. Barger
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Patent number: 4631349Abstract: A process using heterogeneous resin-bonded aluminum phenoxide catalyst to alkylate phenols, the catalyst per se, and a process for making the catalyst. The inventive alkylation process uses ortho-tert-butylphenoxide bonded to a phenolformaldehyde condensation resin heterogeneous catalyst to prepare 2,6-di-tert-butylphenol from isobutylene and ortho-tert-butylphenol.Type: GrantFiled: June 25, 1985Date of Patent: December 23, 1986Assignee: Ethyl CorporationInventors: Dixie E. Goins, Silas W. Holmes, Edward A. Burt
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Patent number: 4599465Abstract: A process for producing an orthoalkylphenol which comprises reacting phenol with an olefin in a liquid phase in the presence of an alumina catalyst, characterized in that the water content in the liquid phase of the reaction system is maintained at a level of not higher than 250 ppm.Type: GrantFiled: June 5, 1985Date of Patent: July 8, 1986Assignee: Mitsubishi Chemical Industries, Ltd.Inventors: Akio Tamaru, Yoshiaki Izumisawa, Hidekichi Hashimoto, Kiyoji Kuma, Takashi Komaya, Masanobu Minagawa
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Patent number: 4568778Abstract: A process for producing tert-amylphenols is described, comprising reacting isoamylene with phenols in the presence of an inorganic solid acid catalyst or an acidic ion exchange resin catalyst. This process permits efficient production of tert-amylphenols, i.e., 2,4-di-tert-amylphenol and p-tert-amylphenol. These tert-amylphenols are useful as starting materials for preparation of color formers for color photography, additives for resins, oil-soluble dyes, additives for lubricating oils, etc.Type: GrantFiled: February 7, 1985Date of Patent: February 4, 1986Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Makoto Imanari, Hiroshi Iwane, Takahiro Sugawara, Tadashi Ayusawa, Tadamichi Aoki
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Patent number: 4560809Abstract: A process for the production of a 2,6-dialkylphenol in high yield wherein the alkyl groups are secondary or tertiary with a reduced overall production of 4-alkylphenol by-products by the aluminum phenoxide catalyzed pressure reaction of isobutylene with phenol and a mixture of 2,4-dialkylphenol and 2,4,6-trialkylphenol which may be obtained, in a cyclic process, as a bottom stream from the distillation of the reaction mixture to obtain the 2,6-dialkylphenol product.Type: GrantFiled: October 9, 1984Date of Patent: December 24, 1985Assignee: Ethyl CorporationInventors: Dixie E. Goins, Harold V. Huggins, Edward A. Burt, Silas W. Holmes
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Patent number: 4528407Abstract: An improved catalytic process for selectively ortho-alkylating a phenolic compound which comprises reacting a phenolic compound with an alcohol, optionally in the presence of water, and a catalyst composite consisting essentially of the calcination residue obtained from heating an admixture of magnesium carbonate and/or magnesium hydroxide and a manganese compound.Type: GrantFiled: October 26, 1981Date of Patent: July 9, 1985Assignee: General Electric CompanyInventors: William E. Smith, Richard A. Battista
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Patent number: 4398048Abstract: Substantially improved yields of 2,4,6-trialkylphenols result from alkylating a mixture of phenol and 2,6-dialkylphenol, the latter being a by-product of the alkylation reaction. This results flows from an unexpected synergistic effect accompanying transalkylation. The continuous method of making 2,4,6-trialkylphenol based on this property affords the highly desirable trialkylated phenols in high yield.Type: GrantFiled: October 21, 1981Date of Patent: August 9, 1983Assignee: UOP Inc.Inventor: Bruce E. Firth
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Patent number: 4391998Abstract: Phenol is catalytically alkylated with an isopropanol or propylene alkylating agent to form high yields of an isopropylphenol product enriched in the para-isomer of isopropylphenol. Such an alkylation process is carried out under catalytic alkylation conditions including a temperature of from about 200.degree. C. to 300.degree. C. and contact with a crystalline zeolite catalyst having a silica to alumina molar ratio of at least about 12 and a constraint index of about 1 to 12.Type: GrantFiled: October 21, 1981Date of Patent: July 5, 1983Assignee: Mobil Oil CorporationInventor: Margaret M. Wu
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Patent number: 4359591Abstract: This invention relates to a process for reacting phenol, mono- and di-alkyl phenols having at least one free o-position with methanol and/or dimethyl ether in the gas phase to form o-substituted phenols in the presence of a catalyst of oxides of iron, chromium, silicon and at least one oxide of an alkaline-earth metal, lanthanum and manganese or in the presence of a catalyst of oxides of iron, chromium, a metal from the group comprising germanium, titanium, zirconium, tin, lead, and at least one oxide of an alkali metal, alkaline-earth metal, lanthanum and manganese.Type: GrantFiled: March 30, 1981Date of Patent: November 16, 1982Assignee: Union Rheinische Braunkohlen Kraftstoff AktiengesellschaftInventors: Max Fremery, Karl-Heinz Keim, Joachim Korff
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Patent number: 4323715Abstract: Mono-tertiary butylhydroquinone may be prepared in a continuous method of operation by reacting hydroquinone with isobutylene in the presence of an acidic alumina catalyst. The alkylation is effected in a reaction medium which comprises an ether, and particularly a polyether such as the dimethyl ether of triethylene glycol.Type: GrantFiled: November 20, 1980Date of Patent: April 6, 1982Assignee: UOP Inc.Inventors: Dusan J. Engel, Thomas P. Malloy
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Patent number: 4283573Abstract: A method for producing long chain-length alkylphenols with preferential production of para-alkylphenols and placement of the phenolic moiety at the #2 position on the alkyl chain. The reaction is carried out in the presence of crystalline zeolites having a major pore dimension of about six to seven angstrom units.Type: GrantFiled: November 20, 1979Date of Patent: August 11, 1981Assignee: Mobil Oil CorporationInventor: Lewis B. Young
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Patent number: 4275249Abstract: A process for introducing a plurality of alkyl groups into the aromatic ring of a hydroxy-substituted aromatic compound comprises contacting said aromatic compound with an olefin in the presence of alumina or halided alumina as catalyst and recovering the product. When said aromatic compound is phenol, said olefin is isobutylene, and said catalyst is fluorided or chlorided alumina, 2,4-di-t-butylphenol is formed with superior selectivity.Type: GrantFiled: November 30, 1979Date of Patent: June 23, 1981Assignee: UOP Inc.Inventor: Bruce E. Firth
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Patent number: 4260833Abstract: A process for introducing a plurality of alkyl groups into the aromatic ring of a hydroxy-substituted aromatic compound comprises contacting said aromatic compound with an olefin in the presence of a lithiated alumina as catalyst and recovering the product. When said aromatic compound is phenol, said olefin is iso-butylene, and said catalyst is lithiated alumina, 2,4-di-t-butylphenol is formed with superior selectivity.Type: GrantFiled: November 30, 1979Date of Patent: April 7, 1981Assignee: UOP Inc.Inventor: Bruce E. Firth
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Patent number: 4232176Abstract: Method of removing aluminum-containing catalyst from phenol alkylation products comprises treating phenol alkylation products with water at a temperature of 165.degree.-250.degree. C., with water being in molar excess to aluminum in a range of 3-20. The resulting residue of meta-aluminate is easily separated by filtration.The present invention allows eliminating constant control of aluminum content in alkylation products, easily removing the catalyst therefrom and eliminating the loss of phenol alkylation products.Type: GrantFiled: June 14, 1976Date of Patent: November 4, 1980Inventors: Engel R. Adigamov, Yakov A. Gurvich, Alexandr G. Liakumovich, Igor J. Logutov, Jury I. Michurov, Alexei S. Polenov, Vladimir A. Yanshevsky
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Patent number: 4208537Abstract: The selective alkylation of a phenolic compound having a hydrogen atom in at least one of the ortho positions is achieved by reacting the phenolic compound with an alcohol in the vapor phase in the presence of a catalyst containing mixed oxides of chromium and tin. The catalyst can additionally contain iron oxide, sulfate radical, or a combination thereof.Type: GrantFiled: November 27, 1978Date of Patent: June 17, 1980Assignee: Mitsui Toatsu Chemicals IncorporatedInventors: Motoo Kawamata, Kazushi Ohshima, Akihide Kudoh, Makoto Kotani
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Patent number: 4166191Abstract: Highly pure p-tertiary-butyl phenol can be prepared from an olefin composition comprising a major amount of at least one isobutylene oligomer and a minor amount of a codimer of n-butene and isobutylene. The reaction of said olefin composition with phenol is carried out in the presence of water and synthetic silica-alumina catalyst at a temperature of 140.degree.-230.degree. C.Type: GrantFiled: February 9, 1978Date of Patent: August 28, 1979Assignees: Hitachi Chemical Company, Ltd., Maruzen Oil Co, Ltd., Goi Chemical Co, Ltd.Inventors: Masakazu Ueoka, Yasuyuki Iguchi, Takayuki Saito, Hiroshi Okamura
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Patent number: 4122289Abstract: A method for preparing 2,6-ditert.butylphenol which comprises alkylation of phenol in the presence of monotert.-butylphenol and a catalyst, viz. aluminium dissolved in phenol with gradually lowering the process temperature from 120.degree. to 50.degree. C and reducing the concentration of isobutylene in the mixture of isomeric butenes from 80 to 1.5 mol.%, followed by isolation of the desired product.The method according to the present invention makes it possible to achieve a high degree of conversion of isobutylene without impairing quality of the desired product. The amount of by-products formed in the process is 2-3 times as less as in the prior art methods.Type: GrantFiled: August 5, 1977Date of Patent: October 24, 1978Inventors: Jury Ivanovich Michurov, Vladimir Avgustovich Yanshevsky, Rufina Alexandrovna Filippova, Yakov Abramovich Gurvich, Igor Jurievich Logutov, Sofya Alexandrovna Egoricheva, Izrail Markovich Belgorodsky, Sergei Gerasimovich Vyborov
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Patent number: 4113976Abstract: A method of preparing 2,6-di-tert.butylphenol comprises alkylation of phenol with isobutylene at a temperature within the range of from 100.degree. to 110.degree. C in the presence, as a catalyst, of phenyloxyorthotertbutylphenoxyhydroaluminum acid of the formula:[(OC.sub.6 H.sub.5).sub.n (ortho-tert.C.sub.4 H.sub.9 C.sub.6 H.sub.4 O).sub.m Al]Hwhereinn = 1 to 3;m = 1 to 3;n + m = 4.The method of the present invention makes it possible to increase the product yield to 80% by weight and to conduct the process under atmospheric pressure.Type: GrantFiled: April 18, 1977Date of Patent: September 12, 1978Inventors: Jury Ivanovich Michurov, Boris Izrailevich Pantukh, Valerian Mikhailovich Sobolev, Grigory Iosifovich Rutman, Igor Jurievich Logutov, Vladimir Romanovich Dolidze