Two Phenols Bonded Directly To Two Different Carbons Of An Acyclic Chain Patents (Class 568/729)
  • Patent number: 5545399
    Abstract: A composition for topical application to the skin in order to promote the repair of photo-damaged or aged skin and/or to reduce or prevent damaging effects of ultra-violet light on skin and/or to lighten the skin comprising a hydrocalchone of general structure: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3, which may be the same or different, represent H, --OH, --OR or --COR (where R is a C.sub.1-20 alkyl group);R.sub.4, R.sub.5, R.sub.6 and R.sub.7, which may be the same or different, represent H or --COR (where R is as herein before defined).Optional additional ingredients include sunscreens and other skin lightening skin lightening agents, particularly retinol or derivatives thereof.
    Type: Grant
    Filed: October 24, 1994
    Date of Patent: August 13, 1996
    Assignee: Chesebrough-Pond's USA Co.
    Inventors: Caroline M. Lee, Martin R. Green, Giuseppe Prota
  • Patent number: 5475154
    Abstract: Low-color bisphenols may be produced by condensing phenol with ketones in the presence of a strong-acid cation exchange resin acting as an acid catalyst for the condensation reaction, and of a small amount, relative to the acid catalyst, of a weak-base anion exchange resin.
    Type: Grant
    Filed: March 10, 1994
    Date of Patent: December 12, 1995
    Assignee: Rohm and Haas Company
    Inventors: Eric G. Lundquist, Michael P. Bigwood
  • Patent number: 5473003
    Abstract: Compositions comprising an organic material which is sensitive to thermal, oxidative and/or actinic degradation and at least one compound of the formula I ##STR1## in which Z.sub.1 and Z.sub.2 independently of one another are C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl, phenyl-C.sub.1 -C.sub.4 alkyl or (C.sub.1 -C.sub.4 alkyl)phenyl andp is a number from 4 to 18,with the proviso that Z.sub.1 and Z.sub.2 are not simultaneously tertiary alkyl radicals. Some of the compounds of the formula I are novel.The compounds of the formula I can also be employed as stabilizers as a mixture with compounds of the formula VI and/or of the formula VII ##STR2## in which n and the radicals R.sup.1, R .sup.1 ' and A are as defined in claims 14 and 15.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: December 5, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Rita Pitteloud, Paul Dubs, Bernard Gilg
  • Patent number: 5414150
    Abstract: 4,4'-Dihydroxy-alpha-alkylstilbenes of high purity are prepared by reacting at a temperature of from about -20.degree. C. to about 20.degree. C. a mixture of (1) at least one alpha-haloketone, (2) at least one phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound, and (3) at least one strong protonic acid or Lewis acid; such that the mole ratio of phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound:alpha-haloketone(s) is from 0.1:1 to 1.9:1, and the mole ratio of phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound:alpha-haloketone(s):strong protonic acid or Lewis acid is from about 0.1:1:0.0026 to about 1.9:1:0.95. The high purity 4,4'-dihydroxy-alpha-alkylstilbenes are useful for the advancement of epoxy resins, for the preparation of phenoxy resins and for the preparation of epoxy resins.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: May 9, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Maria I. Villarreal, David A. Carr
  • Patent number: 5345000
    Abstract: High purity, crystalline adduct of bisphenol A and phenol is produced multi-stage crystallization of a phenolic slurry of bisphenol A with a crystal separation and washing step being interposed between each of the two stages. Each of the crystallization stage includes a series of crystallization towers operated at decreasing temperatures. The crystallization of the slurry is performed by continuously discharging a portion of the slurry from each of the crystallization towers, introducing the discharged slurry into one or more coolers and then recycling the cooled slurry to the tower. Another portion of the slurry in each crystallization slurry is continuously discharged, heated for dissolving fine crystals of the adduct and then recycled to the crystallization tower so that large crystals are grown in each of the crystallization steps. An apparatus having a plurality of coolers and suitable for effecting the above crystallization is also disclosed.
    Type: Grant
    Filed: March 3, 1993
    Date of Patent: September 6, 1994
    Assignee: Chiyoda Corporation
    Inventors: Nobuo Moriya, Keiji Shimoda, Sachio Asaoka, Takao Kameda, Kouji Sakashita, Tetsuo Maejima, Makoto Yasui, Hiroaki Nishijima, Nobuhiro Onda, Takeshi Kouzaki
  • Patent number: 5306748
    Abstract: Fluorine-modified thermosetting reins are available as phenolic or epoxy resins having trifluoromethyl groups and a naphthalene skeleton in a molecule. They are useful as components of resin compositions or resin modifiers and cure to products having low water pickup, low coefficient of thermal expansion, and adhesion as well as heat resistance and mechanical strength. Thermosetting resin compositions having such a thermosetting resin blended therein are useful in semiconductor element packaging.
    Type: Grant
    Filed: July 29, 1992
    Date of Patent: April 26, 1994
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshio Shiobara, Hisashi Shimizu, Manabu Narumi
  • Patent number: 5245084
    Abstract: The mixture consists of at least one organic peroxide, at least one hydroquinone derivative of the general formulae I and/or II and/or III ##STR1## wherein R and R.sup.1, which may be identical or different, stand for H or t-alkyl, and X stands, for example, for C.sub.1-18 -alkylene, and a crosslinkage promoter, and permits the crosslinkage of polymers and at the same time extends the scorch time, which must be understood as the processing time.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: September 14, 1993
    Assignee: Luperox GmbH
    Inventors: Jurgen Groepper, Harald Hofmann
  • Patent number: 5185454
    Abstract: Symmetrical diaryl-acetylenes can be prepared by reacting an aryl halide with acetylene in the presence of a palladium catalyst and a base. If the acetylene is introduced into the liquid reaction mixture using a high intensity gas dispersion means, the aryl halide used can be an aryl bromide.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: February 9, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Axel Bader, Dieter Arlt
  • Patent number: 5138103
    Abstract: A process for producing tetrabromobisphenol A of high quality, which comprises brominating bisphenol A with bromine, wherein a solvent mixture comprising a hydrohalogenic acid and an alcohol, is used as the solvent for reaction. Also disclosed is a process for producing tetrabromobisphenol A of high quality, which comprises brominating bisphenol A with bromine in an alcohol, wherein the reaction temperature is set at a level of from -10.degree. to +20.degree. C., and water is added in an aging step.
    Type: Grant
    Filed: August 16, 1991
    Date of Patent: August 11, 1992
    Assignee: Tosoh Corporation
    Inventors: Hisao Eguchi, Masashige Kubo, Noritaka Nagasaki, Koji Kunimoto
  • Patent number: 5136114
    Abstract: The invention relates to a new process for the preparation of geminal diarylalkanes of the formula ##STR1## by Friedel-Crafts alkylation of aromatic compounds with specific aliphatic halogen compounds (addition compounds of CCl.sub.4 , to .alpha.-olefins), to new geminal diarylalkanes and the aralkyl compounds resulting as intermediates.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 5008471
    Abstract: As a process for preparing a compound of the formula ##STR1## in which both Rs are H or --OH comprising the steps: a. of treating the ethyl ester of caffeic acid with a trialkylsilyl chloride at ambient conditions in equimolar proportions in the presence of a base;b. of reduction of the resulting product with an aluminium hydride reagent at sub-zero temperature and equimolar proportions to yield the corresponding allylic alcohol;c. of halogenation of this allylic alcohol with thionyl chloride or a phosphorus trihalide to yield the corresponding allyl halide;d. of coupling this allyl halide with the silyl ether of compound of the formula ##STR2## in refluxing ether solutions; and e. of hydrolysis of this coupled product with tetra alkyl ammonium flouride at ambient conditions and of equimolar proportions.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: April 16, 1991
    Assignee: Rooperol (N.A.)
    Inventors: George L. Wenteler, Karl H. Pegel, Siegfried Drews, Hans Kundig
  • Patent number: 4962240
    Abstract: A method for symmetrically dimerizing phenols which comprises oxidizing phenols in molten state in the liquid phase using a transition metal compound as a catalyst and an oxygen-containing gas as an oxidizing agent to conduct dimerization; and a process for producing diphenols which comprises oxidizing phenols in molten state in the liquid phase using a transition metal compound as a catalyst and an oxygen-containing gas as an oxidizing agent to conduct dimerization, and then interrupting introduction of the oxygen-containing gas to conduct a proton disproportionation reaction.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: October 9, 1990
    Assignee: Danippon Ink and Chemicals, Inc.
    Inventors: Taku Kitamura, Noriko Kurokawa, Katsuji Takahashi
  • Patent number: 4960956
    Abstract: Ring-arylcyclobutenealkylated di(hydroxyphenyl) compounds having at least one arylcyclobutenealkyl moiety attached to at least one of the phenyl rings self-cure upon heating to produce rigid, relatively insoluble resins of the thermoset type.
    Type: Grant
    Filed: May 9, 1989
    Date of Patent: October 2, 1990
    Assignee: Shell Oil Company
    Inventor: Pui-Kwan Wong
  • Patent number: 4956502
    Abstract: A process for preparing a compound of the formula ##STR1## in which both Rs and H or OH; comprising the steps a. of treating the ethyl ester of caffeic acid with trialkylsilyl chloride at ambient conditions in equimolar proportions in the presence of a base;b. the reduction of the ester to the corresponding allylic alcohol with aluminum hydride reagent;c. of oxidizing the resulting product with manganese dioxide at ambient temperature and in excess molar proportion to yield the corresponding allylic aldehyde;d. of coupling the latter with the silyl ether of the relative phenyl acetylide; ande. of hydrolysis of this coupled product with alkylammonium fluoride at ambient conditions in equimolar proportions.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: September 11, 1990
    Assignee: Rooperol (N.A.) NV
    Inventors: George L. Wenteler, Karl H. Regel, Siegfried Drews, Hans Kundig
  • Patent number: 4954659
    Abstract: A grignard synthesis of pharmacologically active 1,4-bis(dihydroxyphenyl)butane and analogs, as well as novel intermediates, is provided, comprising preparing a grignard reagent preferably, a 3,4-dialkoxyphenyl propyl magnesium bromide, which may be reacted with carbonyl compounds to form intermediates of desired end products, said carbonyl compounds preferably being 3,4-dialkoxybenzaldehydes. The resulting alcohol is converted to a corresponding ether or siloxy compound, at the carbonyl site. The oxy-substituent is cleaved off; and the benzene ring or rings dealkylated to leave hydroxy substituents on the rings.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: September 4, 1990
    Assignee: Chemex Pharmaceuticals, Inc.
    Inventors: Robert M. Parkhurst, Ronald S. Pardini
  • Patent number: 4927973
    Abstract: A process for the continuous purification of crude bisphenol which comprises (1) forming a single liquid phase comprising a hot mixture of crude bisphenol and water in a ratio substantially of from about 75% to about 85% weight of crude bisphenol to about 15% to about 25% weight water; (2) continuously feeding this mixture together with a stream of warm water to a first crystallization zone at a temperature sufficient to maintain a bisphenol-rich liquid phase, a water-rich phase and a crystalline phase comprising about 70% to about 95% of the total bisphenol in the mixture; (3) passing the three-phase mixture of bisphenol and water to a second crystallization zone operated at about 85.degree. C. to about 97.degree. C. until about 90% to about 99% of the total bisphenol is crystallized; and (4) recovering the purified bisphenol crystals.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: May 22, 1990
    Assignee: Shell Oil Company
    Inventors: Walter Dong, Paul V. Shaw, James L. Buechele
  • Patent number: 4791234
    Abstract: Spirobiindane bisphenols of high purity, suitable for conversion to high molecular weight polycarbonates, are prepared by reacting a bisphenol or 4-isopropenylphenol with a metal halide Lewis acid or an alkanesulfonic acid, followed by removing impurities including phenols, 1-(4-hydroxyphenyl)indanols and the like. A step of purification by precipitation with water from a methanol-methylene chloride solution is included.
    Type: Grant
    Filed: October 10, 1986
    Date of Patent: December 13, 1988
    Assignee: General Electric Company
    Inventors: Gary R. Faler, Jerry C. Lynch
  • Patent number: 4778936
    Abstract: A triphenol type compound represented by the following formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 independently represent hydrogen, a halogen, a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkoxy group.The triphenol type compound can be used, as a branching agent for the production of a polycarbonate comprising (A) a carbonic acid component unit, (B) a divalent phenol component unit, and (C) a tripenol type compound component unit derived from the above-mentioned triphenol type compound. The triphenol type compound unit (C) is used in an amount of 0.01 to 10 mole %, based on the divalent phenol component unit (B) and the intrinsic viscosity [.eta.], determined at 25.degree. C. in methylene chloride, of the polycarbonate is 0.4 to 1.0 dl/g and the glass transition temperature (Tg), determined by a differential scanning type calorimeter is 150.degree. C. to 300.degree. C.
    Type: Grant
    Filed: October 7, 1986
    Date of Patent: October 18, 1988
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Kenichi Mizuno, Yozo Jujo, Hajime Oyoshi
  • Patent number: 4745233
    Abstract: Antitumor compounds corresponding to the following formula: ##STR1## in which the substituents R.sub.1 and R.sub.2 may be the same or different and represent hydrogen, an aminocarbonyl group, a C.sub.1 -C.sub.6 alkylaminocarbonyl group, a di-C.sub.1 -C.sub.6 -alkylaminocarbonyl group, the group PO(OH).sub.2, a C.sub.2 -C.sub.8 alkanoyl group, a C.sub.2 -C.sub.8 halogen alkanoyl group or a C.sub.3 -C.sub.8 alkenoyl group, a process for their preparation, and their use in treating oestrogen-receptor-positive-tumors as well as the prostate carcinoma.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: May 17, 1988
    Assignee: Asta-Werke Aktiengesellschaft
    Inventors: Helmut Schonenberger, Rolf W. Hartmann, Martin Schneider, Walter Schwarz, Jurgen Engel
  • Patent number: 4716252
    Abstract: Bis-hydroxyphenyl-n-alkanes are prepared by contacting dicarboxylic acids or dicarboxylic acid derivatives with fluorine-containing organic sulphonic acids, where appropriate with the addition of a phenolic compound, and converting the alkanediones, which are thus obtainable, into bis-hydroxyphenyl-n-alkanes by hydrogenation and, where appropriate, an additional ether cleavage. The invention also relates to new bis-hydroxyphenyl-n-alkanes and to new alkanediones.
    Type: Grant
    Filed: July 28, 1986
    Date of Patent: December 29, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Wagner, Kurt Halcour, Hans-Rudolf Dicke, Volker Eckhardt
  • Patent number: 4705901
    Abstract: Prepare novel ring-brominated derivatives of tetraalkyl dihydroxy diaromatic compounds, e.g. 4,4'-(1,2-ethanediyl)bis(3,5-dibromo-2,6-dimethyl-phenol).
    Type: Grant
    Filed: August 26, 1986
    Date of Patent: November 10, 1987
    Assignee: The Dow Chemical Company
    Inventor: Abel Mendoza
  • Patent number: 4701566
    Abstract: Spirobiindane bisphenols are prepared by contacting a mixture of a bisphenol or a 4-isopropenylphenol and a 1-(4-hydroxyphenyl)indanol with a metal halide Lewis acid or an alkanesulfonic acid. High purity spirobiindane bisphenols may be prepared by employing a purification sequence, which preferably includes a step of precipitation of the product with water from a methanol-methylene chloride solution.
    Type: Grant
    Filed: October 10, 1986
    Date of Patent: October 20, 1987
    Assignee: General Electric Company
    Inventors: Gary R. Faler, Jerry C. Lynch
  • Patent number: 4644085
    Abstract: The invention relates to a new anti-cancer chemical compound which has been called rooperol and certain derivatives thereof of the general formula ##STR1## in which A is chosen from the group including a phenyl group, a substituted phenyl group and --CH.sub.2 --O--R.sup.5 where R.sup.5 =H, an alkyl (C.sub.1 -C.sub.5), aralkyl or acyl substituent; R.sup.1 and R.sup.2 are chosen from substituents including H for both or singly if one of them is --OH, --NH.sub.2, --SH, ##STR2## or taken together R.sup.1 and R.sup.2 are =0; R.sup.3 is H or ##STR3## where R.sup.6 is an alkyl group (C.sub.1 -C.sub.7); either of R.sup.4 or B are chosen from substituents including H, ##STR4## a phenyl group, substituted phenyl group or a furyl group.
    Type: Grant
    Filed: June 4, 1985
    Date of Patent: February 17, 1987
    Assignee: Rooperol (NA) NV
    Inventors: Siegfried Drewes, Roelof W. Liebenberg
  • Patent number: 4621159
    Abstract: Prepare novel ring-brominated derivatives of tetraalkyl dihydroxy diaromatic compounds, e.g. 4,4'-(1,2-ethanediyl)bis(3,5-dibromo-2,6-dimethyl-phenol).
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: November 4, 1986
    Assignee: The Dow Chemical Company
    Inventor: Abel Mendoza
  • Patent number: 4562298
    Abstract: A process for producing novel compositions including optically active molecules of nordihydroguaiaretic acid (d,1-2,3-dimethyl,1,4-bis(3,4-dihydroxyphenyl)butane) and intermediates, starting with 1,4-bis(3,4-dimethoxyphenyl)butanone, or other structurally similar composition having oxy substituents at the 3,4-phenyl positions, comprising (1) forming the corresponding butanol; (20) forming the corresponding 1,4-butane ether or siloxy composition; (3) cleaving the oxy substituent from the butane chain at the 1 and 4 positions; (4) dealkylating the phenols at the 3,4 positions to leave hydroxy substituents with hydrobromic acid reflux for 8 to 10 hours. Optical orientation is preserved throughout.
    Type: Grant
    Filed: October 25, 1982
    Date of Patent: December 31, 1985
    Assignee: Chemex Pharmaceuticals, Inc.
    Inventors: Robert M. Parkhurst, Ronald S. Pardini
  • Patent number: 4552876
    Abstract: Compounds of the formula: ##STR1## wherein, R is H, alkyl, cycloalkyl, aryl, or heteroaryl;R.sub.1 is H, alkyl, cycloalkyl, aryl, heteroaryl, substituted heteroaryl, aralkyl, substituted aryl, halo, OR.sup.2, SR.sup.2, NR.sub.2, CF.sub.3, NO.sub.2, CN, COOR.sup.2, CHO, SO.sub.3 H or SO.sub.2 NH.sub.2,whereinR.sup.2 is H, methyl, ethyl or propyl;Y is ##STR2## Z is O, S, NH or CH.sub.2 ; X is --CH.sub.2 --, ##STR3## or --(CH.sub.2).sub.n CHOH(CH.sub.2).sub.n --; whereinR.sup.2 is H, methyl, ethyl or propyl;n is 1-10, and pharmaceutically acceptable salts thereof have antiallergy and antiinflammatory activity.
    Type: Grant
    Filed: July 9, 1984
    Date of Patent: November 12, 1985
    Assignee: USV Pharmaceutical Corp.
    Inventors: Howard Jones, Ernest Magnien, John H. Musser, Mujahid L. Shaikh
  • Patent number: 4529556
    Abstract: The invention bis((aryl)vinyl)benzenes wherein the aryl and benzene moieties may be substituted, and the vinyl carbon alpha to the central benzene ring may be further substituted with an aliphatic group.
    Type: Grant
    Filed: August 19, 1983
    Date of Patent: July 16, 1985
    Assignee: The Dow Chemical Company
    Inventor: Kenneth J. Bruza
  • Patent number: 4427697
    Abstract: The present invention provides 1,2-diphenylethane derivatives of the general formula: ##STR1## wherein X is a hydrogen or halogen atom, R and R', which may be the same or different, are alkyl radicals optionally substituted by halogen atoms, R.sub.1 and R.sub.2, which may be the same or different, are acyl radicals, hydroxyl groups or acylated hydroxyl groups and R.sub.3 and R.sub.4, which may be the same or different, are hydroxyl groups or acylated or alkylated hydroxyl groups.The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them.
    Type: Grant
    Filed: November 16, 1981
    Date of Patent: January 24, 1984
    Assignee: Biorex Laboratories Limited
    Inventor: Rosalind P. K. Chan
  • Patent number: 4371719
    Abstract: Curable mixtures of(a) maleimides of the general formula I ##STR1## wherein R is an n-valent aliphatic or aromatic radical, and n is the number 1, 2 or 3; and(b) mono- or polyvalent phenols which contain in the molecule at least one 1-propenyl group in the ortho- or para-position with respect to the hydroxyl group, or isomeric mixtures of mono- or polyvalent phenols which are propenyl-substituted in the ortho- or para-position and mono- or polyvalent phenols which are allyl-substituted in the ortho- or para-position, the proportion of propenyl groups in the isomeric mixture having to be at least 5 equivalent-%, relative to the sum of the equivalents of propenyl and allyl groups.The novel mixtures cure at elevated temperatures relatively rapidly, and produce molded materials having valuable mechanical properties.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: February 1, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Abdul-Cader Zahir, Siegfried Wyler
  • Patent number: 4343796
    Abstract: The invention relates to compounds of the formula: ##STR1## in which R.sub.1 and R.sub.2 are the same or different groups selected from hydrogen or acyl orR.sub.1 and R.sub.2 together may represent an acetal group, andX and Y are the same or different groups selected from hydroxy, an etherified hydroxy and an esterified hydroxy group,having valuable lipid lowering, anti-inflammatory and immuno-modulating properties.
    Type: Grant
    Filed: June 11, 1981
    Date of Patent: August 10, 1982
    Assignee: AKZO NV
    Inventor: Marinus B. Groen
  • Patent number: 4310702
    Abstract: Sulfuryl chloride is reacted in the liquid phase with an organic reactant which is a ketone or aromatic alcohol unsubstituted on both ortho carbons in the presence of a moderator selected from the group consisting of aliphatic alcohols of 1-3 carbons and aliphatic ethers of 2-6 carbons, with sufficient moderator being present to selectively produce a product substantially free of compounds with more than one chlorine atom per carbonyl or aromatic hydroxy. The products, such as monochloroacetone, monochlorocyclohexanone, monochlorophenol and 2,2-bis(3-chloro-4-hydroxyphenyl)propane, are useful as chemical intermediates and as monomers for flame retardant polymers.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: January 12, 1982
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Milorad M. Rogic
  • Patent number: 4291177
    Abstract: Highly pure dihalodiphenols or predetermined, statistical mixtures of unreacted, monohalo- and dihalodiphenols are obtained reacting the diphenol, which is suspended or dissolved in a suitable solvent, with a halogen while concurrently purging the reaction with a gas that is inert to the reaction.
    Type: Grant
    Filed: December 6, 1979
    Date of Patent: September 22, 1981
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles A. Wilson, II
  • Patent number: 4275245
    Abstract: An improved process for obtaining halogenated diphenols which can be pure dihalodiphenols or predetermined, statistical mixtures comprising unreacted diphenol, monohalodiphenols and dihalodiphenols.
    Type: Grant
    Filed: July 16, 1979
    Date of Patent: June 23, 1981
    Assignee: General Electric Company
    Inventor: Victor Mark
  • Patent number: 4243539
    Abstract: Lubricant compositions are stabilized against oxidative degradation by incorporating therein a minor effective amount of a reaction product produced from singlet oxygen and a hindered bis-p-methylphenol.
    Type: Grant
    Filed: August 6, 1979
    Date of Patent: January 6, 1981
    Assignee: Mobil Oil Corporation
    Inventors: Malvina Farcasiu, Susan D. Brandes
  • Patent number: 4210765
    Abstract: An improved process for obtaining halogenated diphenols which can be pure dihalodiphenols or predetermined, statistical mixtures comprising unreacted diphenol, monohalodiphenols and dihalodiphenols.
    Type: Grant
    Filed: February 28, 1978
    Date of Patent: July 1, 1980
    Assignee: General Electric Company
    Inventor: Victor Mark
  • Patent number: 4189610
    Abstract: Dehydrohalogenation-rearrangement of 1,1-bis(4-oxy-substituted aryl)-2-haloethanes to yield 4,4'-dioxysubstituted stilbenes is effected by heating an acidic reaction medium comprising the 1,1-bis(4-oxy-substituted aryl)-2-haloethane dissolved in a solution of an aliphatic carboxylic acid and a carboxylic acid salt. The process is particularly directed to the preparation of 4,4'-dihydroxystilbene from 1,1-bis(4-hydroxyphenyl)-2-chloroethane.
    Type: Grant
    Filed: October 31, 1977
    Date of Patent: February 19, 1980
    Assignee: Monsanto Company
    Inventor: James P. Coleman
  • Patent number: 4162265
    Abstract: Difunctional aromatic enyne compounds are prepared by the catalytic coupling of substituted monoethynyl compounds. The compounds are useful as monomers in polycondensation reactions for the preparation of high molecular weight, thermally stable thermoplastic polymers. On thermal treatment of the polymers, the enyne groups along the polymer backbones react by interchain reactions to provide the solvent and craze resistance required for application as structural materials.
    Type: Grant
    Filed: September 27, 1978
    Date of Patent: July 24, 1979
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Fred E. Arnold, Bruce A. Reinhardt, Frederick L. Hedberg
  • Patent number: 4156787
    Abstract: Dehydrohalogenation-rearrangement-hydrogenation of 1,1-bis(4-hydroxyaryl)-2-haloethanes in an aliphatic carboxylic acid solvent containing a carboxylic acid salt in the presence of gaseous hydrogen and a hydrogenation catalyst is effected in one step to yield 1,2-bis(4-hydroxyaryl)ethanes. The process is particularly directed to the production of 1,2-bis(4-hydroxyphenyl)ethane from 1,1-bis(4-hydroxyphenyl)-2-chloroethane.
    Type: Grant
    Filed: October 31, 1977
    Date of Patent: May 29, 1979
    Assignee: Monsanto Company
    Inventor: James P. Coleman
  • Patent number: 4154969
    Abstract: A combination of zinc oxide and zinc bromide employed as a catalyst for the reaction between phenol and a 1,2-dihaloethane wherein the halogen is chlorine, bromine or iodine provides for increased reaction rates as compared to the use of either zinc compound separately as catalyst and elimination of the induction period characteristic of the reaction when zinc oxide is used as the catalyst.
    Type: Grant
    Filed: March 24, 1977
    Date of Patent: May 15, 1979
    Assignee: Monsanto Company
    Inventor: Robert G. Schultz
  • Patent number: 4139544
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of phenols and naphthols are prepared by contacting an aqueous mixture of phenol or naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 8.5-9.5 during the oxidative coupling reaction and a catalyst system comprising a copper, cobalt, nickel, iron, chromium, cerium, or manganese chelate of a polyimino acid containing more than two nitrogen atoms.
    Type: Grant
    Filed: November 26, 1976
    Date of Patent: February 13, 1979
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4133729
    Abstract: The product 1,2-bis(hydroxyphenyl)ethane-1,2-diol of electrolytic reductive coupling of hydroxybenzaldehyde is recovered by purging the electrolyte solution and extracting the 1,2-bis(hydroxyphenyl)ethane-1,2-diol, leaving a product extraction residue which may be used as an essential portion of the electrolyte solution.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: January 9, 1979
    Assignee: Monsanto Company
    Inventor: Christopher J. H. King
  • Patent number: 4110542
    Abstract: A process is described for preparing 4,4'-dihydroxydiphenylethane by reacting phenol with a 1,2-dihaloethane in which the halogen is chlorine, bromine or iodine, in at least the stoichiometric proportions of 2:1 in contact with a catalyst comprising lanthanum oxide supported on an inorganic material such as silica at a temperature from about 125.degree. to about 225.degree. C. and in the presence of a hydrogen halide as a promoter.
    Type: Grant
    Filed: December 30, 1976
    Date of Patent: August 29, 1978
    Assignee: Monsanto Company
    Inventors: James C. Drummond, Lawrence J. Hughes
  • Patent number: 4108908
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.0 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous, manganous or chromic chelate of a thio-acid compound.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: August 22, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4100206
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkyl phenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric or manganous chelate of a keto alcohol compound.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 11, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4100204
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous or manganous chelate of a hydroxy- or keto- acid compound.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 11, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4100203
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 8.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous or manganous chelate of an oxime of a keto or aldehyde compound.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 11, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4100205
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphtol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.5-10 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous, nickelous, ferric, manganous or chromic chelate of an aminoketone compund.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 11, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4100202
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 8.5-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric chelate of a compound selected from the group consisting of quanidines, amides, salens, dihydrazides, triazenes, dihydroxy substituted aromatics, macrocylic polyamines and alpha, delta-polyketones.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 11, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4098830
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol, alkoxyphenyl, or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous, manganous, nickelous, chromic or ferric chelate of a dicarboxylic acid compound.The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: July 4, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge
  • Patent number: 4096190
    Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols are prepared by contacting an aqueous mixture of an alkyl phenol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 6-9.5 during the oxidative coupling reaction and a catalyst system comprising an ammonia complex of monovalent copper; divalent copper, cobalt, nickel or manganese; or trivalent chromium or iron. The mixture may optionally contain a surfactant.
    Type: Grant
    Filed: November 26, 1976
    Date of Patent: June 20, 1978
    Assignee: ICI Americas Inc.
    Inventor: Thomas F. Rutledge