With Sulfur-containing Reactant Patents (Class 528/226)
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Patent number: 5071944Abstract: A polymerization process is provided for the production of high molecular weight aromatic sulfide/ketone polymer from at least one dihaloaromatic ketone, at least one alkali metal sulfide, at least one polar organic compound and water wherein the polymerization reaction is conducted in two distinct steps separated by an intermediate step of removal of at least a portion of the water.Type: GrantFiled: February 27, 1989Date of Patent: December 10, 1991Assignee: Phillips Petroleum CompanyInventors: Michael D. Cliffton, Jon F. Geibel
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Patent number: 5066775Abstract: The invention relates to new sulphur-containing copolymers, a process for their preparation from a sulphur source and a mixture of dihalogenoaromatics and dihalogenoaliphatics and their use for the production of shaped articles.Type: GrantFiled: February 5, 1990Date of Patent: November 19, 1991Assignee: Bayer AktiengesellschaftInventors: Ernst-Ulrich Dorf, Klaus Reinking, Wolfgang Jakob, Erhard Tresper, Wolfgang Russeler
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Patent number: 5064934Abstract: Thermosetting Schiff base resins, their preparation and their applications re described.These thermosetting Schiff base resins can be defined as responding to the general formula: ##STR1## Radicals Ar.sub.1, Ar.sub.2 and Ar.sub.3 are chosen so that the softening temperature of the resins is less than about 150.degree. C.The resins can be prepared by direct condensation of an ethynyl benzaldehyde or acetophenone on a telechelic diamine oligomer obtained by reaction of a diamine containing flexibilizing groups on a derivative of benzhydrol tetracarboxylic acid. These Schiff base resins can be used by bulk thermal polymerization particularly to prepare adhesives or composite matrices.Type: GrantFiled: April 2, 1990Date of Patent: November 12, 1991Assignee: Centre d'Etude des Materiaux Organiques pour Technologies AvanceesInventors: Regis Mercier, Thierry Pascal, Bernard Sillion
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Patent number: 5064937Abstract: A process for preparing a polymer having repeating units corresponding to the structure ##STR1## wherein y is in the range of 0.005 to 0.15, x is in the range of 0.02 to 0.25, n is at least 200, and R a divalent aromatic radial. The polymer is prepared by reacting a diiodoaromatic compound and elemental sulfur.Type: GrantFiled: June 6, 1990Date of Patent: November 12, 1991Assignee: Eastman Kodak CompanyInventors: David R. Fagerburg, Joseph J. Watkins, Paul B. Lawrence, Mark Rule
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Patent number: 5059666Abstract: Enamine ketone and enonesulfide polymeric solids are prepared by reacting liquid or low-melting propynone terminated enamine ketone and enonesulfide prepolymers in one-step, or more preferably, in two-step processes. Properties of the resulting polymers are determined by the nature of the reactant selected and by the relative amounts of reactants employed. Where the prepolymers formed possess terminal propynone groups, the prepolymers can subsequently be cross-linked. Copolymers can also be formed by reacting the prepolymers of the invention with vinyl-type monomers to form polymers with cross-linked networks. The polymerization techniques disclosed can be employed to produce thermoplastic, thermoset, and elastomeric products, and they are especially useful in reaction injection molding processes, in adhesive systems, in composite formations, for linings, and gaskets which require chemical resistance.Type: GrantFiled: June 6, 1990Date of Patent: October 22, 1991Assignee: Edison Polymer Innovation CorporationInventor: Frank W. Harris
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Patent number: 5055549Abstract: The present invention is connected with a process for preparing a novel photosensitive polyimide precursor having excellent shelf stability and high sensitivity and containing less impurities.The process for preparing a photosensitive heat-resistant polymer containing a repeating unit represented by the formula (III) comprises the step of reacting a photosensitive group-containing isoimide represented by the formula (I) with a diamine represented by the formula (II) at a temperature of 0.degree. to 100.degree. C. in the presence of a solvent: ##STR1## wherein R.sup.1 is independently a tetravalent carbon cyclic aromatic group or heterocyclic group; R.sup.2 is independently an aliphatic group having at least 2 carbon atoms, an alicyclic group, an aromatic aliphatic group, a carbon cyclic aromatic group, a heterocyclic group or a polysiloxane group; R.sup.3 is a monovalent organic group having a photosensitive unsaturated group; and D is an oxygen atom or .dbd.N--R.sup.3.Type: GrantFiled: January 8, 1990Date of Patent: October 8, 1991Assignee: Chisso CorporationInventors: Hirotoshi Maeda, Kouichi Kunimune
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Patent number: 5055551Abstract: This invention relates to a process for the production of high molecular weight, optionally branched polyarylene sulfides having a reduced content of extractable oligomeric constituents. They are prepared by reaction of alkali sulfides and/or alkali hydrogen sulfides with aromatic dihalogen compounds in a polar organic solvent.Type: GrantFiled: November 13, 1989Date of Patent: October 8, 1991Assignee: Bayer AktiengesellschaftInventors: Manfred Schmidt, Wolfgang Arlt, Erhard Tresper, Wolfgang Russeler
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Patent number: 5045628Abstract: A process is provided for preparing more granular (i.e., higher bulk density) particulate poly(arylene sulfide ketone) or poly(arylene sulfide diketone) resins having associated therewith improved processability and thermal stability, without generating pressures significantly greater than those generated during polymerization reactions of particulate poly(arylene sulfide ketone) or poly(arylene sulfide diketone) resins.Type: GrantFiled: December 29, 1989Date of Patent: September 3, 1991Assignee: Phillips Petroleum CompanyInventor: Afif M. Nesheiwat
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Patent number: 5045630Abstract: Disclosed herein is a process for the preparation of a poly(arylene thioether-ketone) improved in melt stability, which comprises subjecting a poly(arylene thioether-ketone) (PTK) to a heat treatment for 5-5.times.10.sup.3 minutes in a powdery state and a temperature range of 200.degree.-350.degree. C. The PTK has predominant recurring units of the formula ##STR1## and has a melting point, Tm of 310.degree.-380.degree. C., a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree.C./10 min) of at least 10 J/g and a reduced viscosity of 0.2-2.0 dl/g. PTKs improved in melt stability and prepared in accordance with the above-described preparation process are also disclosed.Type: GrantFiled: January 17, 1991Date of Patent: September 3, 1991Assignee: Kureha Kagaku Kogyo K.K.Inventors: Ken Kashiwadate, Yoshikatsu Satake, Takashi Kaneko, Masahito Tada, Takayuki Katto
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Patent number: 5032670Abstract: Disclosed are color concentrate compositions which comprise a polyester having copolymerized therein at least 0.5 weight percent of an anthraquinone colorant compound having the formula ##STR1## wherein AQ is a 1,5- or 1,8-anthraquinonylene radical; R.sup.1 and R.sup.2 are the same or different and are unsubstituted or substituted alkyl, cycloalkyl or aryl; and X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared. Amorphous polyesters and partially-crystalline polyesters are preferred embodiments of the color concentrates. Also disclosed are colored semicrystalline powders which may be obtained from the amorphous and partially-crystalline color concentrates by a dissolution-crystallization-precipitation procedure.Type: GrantFiled: August 30, 1989Date of Patent: July 16, 1991Assignee: Eastman Kodak CompanyInventors: William W. Parham, James J. Krutak, Max A. Weaver, Clarence A. Coates, Jr., Terry A. Oldfield
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Patent number: 5025084Abstract: A polyimide-forming composition comprising(A) a polycarboxylic acid partial ester of formulaHOOC--R.sup.1 --COOR.sup.2 Iwhere R.sup.1 denotes a divalent ethylenically unsaturated aliphatic or cycloaliphatic group of 2 to 20 carbon atoms, and R.sup.2 denotes the residue, after removal of a hydroxyl group, of an alcohol having from 4 to 20 carbon atoms which has a cycloaliphatic, aromatic or heterocyclic ring and is polymerizable on heating in the presence of an acid,(B) a partial ester of formula I above in which R.sup.1 denotes a group of formula II ##STR1## where Ar.sup.1 denotes a tetravalent aromatic group of 6 to 20 carbon atoms linked through aromatic carbon atoms thereof to the indicated carbon atoms, and R.sup.2 is as defined above,(C) an aromatic primary polyamine and(D) a heat-activable substance which releases an acid at a temperature of 100.degree. C. or above.Type: GrantFiled: July 10, 1990Date of Patent: June 18, 1991Assignee: Ciba-Geigy CorporationInventors: Bryan Dobinson, Mark R. Southcott
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Patent number: 5008370Abstract: Disclosed herein is a process for the preparation of a poly(arylene thioether-ketone) improved in melt stability, which comprises subjecting a poly(arylene thioether-ketone) (PTK) to a heat treatment for 5-5.times.10.sup.3 minutes in a powdery state and a temperature range of 200.degree.-350.degree. C. The PTK has predominant recurring units of the formula ##STR1## and has a melting point, Tm of 310.degree.-380.degree. C., a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g and a reduced viscosity of 0.2-2.0 dl/g. PTKs improved in melt stability and prepared in accordance with the above-described preparation process are also disclosed.Type: GrantFiled: November 3, 1989Date of Patent: April 16, 1991Assignee: Kureha Kagaku Kogyo K.K.Inventors: Ken Kashiwadate, Yoshikatsu Satake, Takashi Kaneko, Masahiro Tada, Takayuki Katto
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Patent number: 5003042Abstract: A process is provided for preparing a polymeric resin comprising the steps of: (a) preparing a first slurry, wherein the solid component thereof comprises a first particulate resin selected from the group consisting of poly(arlene sulfide ketone)s and poly(arylene sulfide diketone)s, and wherein the liquid component thereof comprises a polar organic compound; (b) substantially liquifying the first particulate resin to form a mixture comprising the substantially liquified first particulate resin and the polar organic compound; and (c) reducing the temperature of the mixture sufficiently to solidify the substantailly liquified resin and form a second slurry, wherein the solid component thereof comprises a second polymeric resin. The filterability of the slurry containing the second polymeric resin is superior to that of the first slurry.Type: GrantFiled: December 29, 1989Date of Patent: March 26, 1991Assignee: Phillips Petroleum CompanyInventor: Afif M. Nesheiwat
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Patent number: 5003033Abstract: A process for preparing a branched, high molecular weight poly(arylene sulfide ketone) by the addition of a polyhaloaromatic compound to a reaction mixture containing a dihaloaromatic ketone, an organic amide, an alkali metal sulfide, and water, and the product produced therefrom.Type: GrantFiled: April 6, 1990Date of Patent: March 26, 1991Assignee: Phillips Petroleum CompanyInventors: Jon F. Geibel, Lacey E. Scoggins, Michael D. Cliffton
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Patent number: 4999418Abstract: Disclosed are colored polyester compositions comprising a polyester having reacted therewith or copolymerized therein at least one residue of an anthraquinone compound having the formula ##STR1## wherein AQ is the residue of a 9,10-anthraquinone radical; R.sup.1 and R.sup.2 are the same or different and are unsubstituted or substituted alkyl, cycloalkyl or aryl; X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared; and n is 1 or 2. The described anthraquinone compounds possess improved thermal stability and thus are not decomposed at the high temperatures at which polyesters are prepared. Also disclosed are shaped articles, particularly containers, fabricated from the colored polyester compositions.Type: GrantFiled: August 31, 1989Date of Patent: March 12, 1991Assignee: Eastman Kodak CompanyInventors: James J. Krutak, Max A. Weaver, Clarence A. Coates, Jr., Samuel D. Hilbert, Wayne P. Pruett, William W. Parham
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Patent number: 4977236Abstract: A process for preparation of a copoly(arylene sulfide) corresponding to the structure ##STR1## wherein A is a divalent substituted or unsubstituted aromatic radical, T is a monovalent aromatic radical, x is in the range of 0.5 to 0.001 and n is an integer from 1 to 100.Type: GrantFiled: December 5, 1989Date of Patent: December 11, 1990Assignee: Eastman Kodak CompanyInventors: David R. Fagerburg, Joseph J. Watkins, Paul B. Lawrence, Mark Rule
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Patent number: 4958003Abstract: A class of amide group-containing aromatic dihalide compounds are sulfidized together with a class of aromatic dihalide compounds to provide a novel class of aromatic sulfideamide polymers increased in crystalline melting point (T.sub.m). The polymers exhibit excellent resistance to high temperatures, resistance to solvents, flame-retardant properties and improved mechanical properties.Type: GrantFiled: December 23, 1988Date of Patent: September 18, 1990Assignee: Tosoh CorporationInventors: Satoshi Tomagou, Toshikazu Kato, Hiroshi Inoue, Kensuke Ogawara
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Patent number: 4952671Abstract: A copoly(arylene sulfide) corresponding to the structure ##STR1## wherein A is a divalent substituted or unsubstituted aromatic radical, T is a monovalent aromatic radical, x is n the range of 0.5 t 0.001 and n is at least 100.Type: GrantFiled: July 15, 1988Date of Patent: August 28, 1990Assignee: Eastman Kodak CompanyInventors: David R. Fagerburg, Joseph J. Watkins, Paul B. Lawrence, Mark Rule
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Patent number: 4939214Abstract: A film comprised of at least one monomolecular layer composed essentially of a polyimide having repeating units of the formula: ##STR1## wherein R.sup.1 is a tetravalent organic group and R.sup.2 is a bivalent organic group.Type: GrantFiled: November 17, 1986Date of Patent: July 3, 1990Assignees: Mitsubishi Kasei Corporation, Yoshio Imai, Taro HinoInventors: Yoshio Imai, Taro Hino, Mitsumasa Iwamoto, Masa-aki Kakimoto, Masa-aki Suzuki, Toru Konishi
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Patent number: 4935478Abstract: Hot-curable compositions of matter containing (a) an unsaturated imide of the formula I ##STR1## (b) a benzaldehyde derivative of the formula II ##STR2## in which for example M=2, n=zero, o=1 R.sup.1, R.sup.2 and R.sup.3 are each hydrogen and R is 4,4'diphenylmethane are suitable for the production of mouldings having excellent thermostability and resistance to thermal ageing.Type: GrantFiled: July 29, 1988Date of Patent: June 19, 1990Assignee: Ciba-Geigy CorporationInventor: Andreas Kramer
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Patent number: 4931516Abstract: Disclosed herein is a process for producing a medium- or high-molecular-weight polyarylene sulfide which comprises subjecting an alkali metal sulfide, a dihalo aromatic compound and optionally, small amount of tri- or higher polyhalo aromatic compound to dehalogenation and sulfidation reaction at a temperature of from 240.degree. to 270.degree. C. in the presence of a water in amount of from 0.5 to 5 mol per 1 kg of an aprotic organic polar solvent until the conversion of said dihalo aromatic compound reaches from 70 to 98 mol %, thereby forming a polyarylene sulfide prepolymer having a melt viscosity of from 5 to 300 poise (as measured at 310.degree. C. under a shear rate of 200 sec.sup.-1), adding water to the resultant reaction mixture containing the polyarylene sulfide prepolymer so that from 6 to 15 mol of water is present per 1 kg of said solvent, and then continuing the reaction at a temperature of from 240.degree.-290.degree. C.Type: GrantFiled: January 24, 1989Date of Patent: June 5, 1990Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Yo Iizuka, Takao Iwasaki, Takayuki Katto, Zenya Shiiki
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Patent number: 4925912Abstract: The present invention relates to copolyimides of 100-70 mol % of recurring structural units of the formula I and 0-30 mol % of recurring structural units of the formula II ##STR1## in which Z.sup.a is a tetravalent aromatic tetracarboxylic acid radical other than that of thioxanthonetetracarboxylic acid, the carboxyl groups thereof in each case being located in pairs in the ortho-position or peri-position relative to one another, and X.sup.a is a divalent aromatic diamine radical which, in at least one ortho-position relative to at least one nitrogen atom, carries a hydrocarbon substituent having at least one aliphatic .alpha.-hydrogen atom or X.sup.a is a radical of the formula III ##STR2## in which X.sup.c is a divalent aromatic diamine radical which, in ortho-position relative to both nitrogen atoms, carries in each case at least one monovalent hydrocarbon substituent having at least one aliphatic .alpha.-hydrogen atom, n assumes an average value of 1.0 to 2.5, Z.sup.b is as defined for Z.sup.a and X.sup.Type: GrantFiled: December 8, 1988Date of Patent: May 15, 1990Assignee: Ciba-Geigy CorporationInventors: Ottmar Rohde, Stanley J. Jasne, Josef Pfeifer
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Patent number: 4914176Abstract: Novel thermoplastic polymers of relatively high glass transition temperatures are characterized by five-carbon moieties having a keto group in the 3-position alternating with bis(benzoheterocyclic) moieties. The polymers are produced by reaction of a keto-C.sub.5 source, selected from 4-oxoheptanedioic acid compounds or a 1,6-dioxa [4.4] spirodilactone, with a bis(ortho-phenylene amine) compound. Further cyclization of the initial polymer product or reaction of a bis(ortho-phenylenediamine) provides a polymer having a hexacyclic repeating unit.Type: GrantFiled: March 17, 1989Date of Patent: April 3, 1990Assignee: Shell Oil CompanyInventor: Pen C. Wang
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Patent number: 4910285Abstract: Novel polyarylate polymers comprise alternating moieties derived from an aromatic dicarboxylic acid halide, from a hydroxyaryl-substituted 1,6-diaza [4.4] spirodilactam and, optionally, from a di(hydroxyphenyl) compound. The polyarylate polymers are thermoplastic polymers characterized by relatively high glass transition temperatures.Type: GrantFiled: February 23, 1989Date of Patent: March 20, 1990Assignee: Shell Oil CompanyInventor: Pen C. Wang
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Patent number: 4910293Abstract: An amphiphilic high polymer comprises a linear recurring unit containing at least divalent organic group (R.sub.1) having at least two carbon atoms, at least divalent organic group (R.sub.2) having at least two carbon atoms, and at least one C.sub.10-30 hydrocarbon-containing group (R.sub.3) which may have one or more substituent groups, said organic groups R.sub.1 and R.sub.2 being connected to each other by a divalent connecting group, and said hydrocarbon-containing group R.sub.3 being boned to said recurring unit by a covalent bond, and the method for producing the same comprises polycondensating a combination of monomers containing R.sub.1 and R.sub.2.Type: GrantFiled: October 11, 1988Date of Patent: March 20, 1990Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Masakazu Uekita, Hiroshi Awaji
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Patent number: 4895691Abstract: Disclosed herein are poly(arylene thioether-ketone) fibers obtained by melt-spinning a thermoplastic material which comprises 100 parts by weight of a melt-stable poly(arylene thioether-ketone) (PTK) and optionally, up to 50 parts by weight of at least one of thermoplastic resins. The PTK has predominant recurring units of the formula ##STR1## wherein the --CO-- and --S-- are in the para position to each other, and has a melting point, Tm of 310.degree.-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., and a reduced viscosity of 0.3-2 dl/g as determined by viscosity measurement at 25.degree. C. and a polymer concentration of 0.5 g/dl in 98 percent by weight sulfuric acid. The PTK fibers of this invention have high heat resistance and strength.Type: GrantFiled: May 19, 1989Date of Patent: January 23, 1990Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yoshikatsu Satake, Yo Iizuka, Hiroyuki Endo, Toshitaka Kouyama, Takayuki Katto, Zenya Shiiki
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Patent number: 4895892Abstract: Disclosed herein is a melt-stable poly(arylene thioether-ketone) composition, which comprises:(A) 100 parts by weight of a melt-stable poly(arylene thioether-ketone) having predominant recurring units of the formula ##STR1## and having a melting point, Tm of 310.degree.-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C. and a reduced viscosity of 0.2-2 dl/g;(B) 0-400 parts by weight of at least one of thermoplastic resins; and(C) at least one of fibrous fillers and/or at least one of inorganic fillers in a proportion of 0-400 parts by weight per 100 parts by weight of the sum of said components (A) and (B).At least either one of the components (B) or (C) is contained in a proportion of at least 0.1 part by weight per 100 parts by weight of the component (A).Type: GrantFiled: May 12, 1988Date of Patent: January 23, 1990Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yoshikatsu Satake, Takashi Kaneko, Yutaka Kobayashi, Yo Iizuka, Toshitaka Kouyama, Takayuki Katto, Zenya Shiiki
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Patent number: 4895925Abstract: Disclosed herein are a melt-stable poly(arylene thioether-ketone) having predominant recurring units of the formula ##STR1## and having a melting point, Tm of 310.degree.-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., and a reduced viscosity of 0.2-2 dl/g as measured at 25.degree. C. and a polymer concentration of 0.5 g/dl in 98 wt. % sulfuric acid as well as a production process of the poly(arylene thioether-ketone). The poly(arylene thioether-ketone) has melt stability so that conventional melt processing techniques can be applied easily. The poly(arylene thioether-ketone) is a highly-crystalline polymer whose density is at least 1.34 g/cm.sup.3 when annealed at 280.degree. C. for 30 minutes.Type: GrantFiled: May 12, 1988Date of Patent: January 23, 1990Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yoshikatsu Satake, Takashi Kaneko, Yutaka Kobayashi, Yo Iizuka, Takayuki Katto, Zenya Shiiki
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Patent number: 4895924Abstract: Disclosed herein are poly(arylene thioetherketone) fibers obtained by melt-spinning a thermoplastic material which comprises 100 parts by weight of a melt-stable poly(arylene thioether-ketone) (PTK) and optionally, up to 50 parts by weight of at least one of thermoplastic resins. The PTK has predominant recurring units of the formula ##STR1## wherein the --CO-- and --S-- are in the para position to each other, and has a melting point, Tm of 310-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., and a reduced viscosity of 0.3-2 dl/g as determined by viscosity measurement at 25.degree. C. and a polymer concentration of 0.5 g/dl in 98 percent by weight sulfuric acid. The PTK fibers of this invention have high heat resistance and strength.Type: GrantFiled: May 12, 1988Date of Patent: January 23, 1990Assignee: Kureha Kagaku Kogyo K. K.Inventors: Yoshikatsu Satake, Yo Iizuka, Hiroyuki Endo, Toshitaka Kouyama, Takayuki Katto, Zenya Shiiki
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Patent number: 4892929Abstract: Melt stable polymeric resins are provided by process which comprises heating a first particulate resin selected from the group consisting of poly(arylene sulfide ketone) and poly(arylene sulfide diketone), while in the presence of a gaseous oxidizing atmosphere, to a temperature at least about 150.degree. C. (302.degree. F.) but below the melting point of the first particulate resins, for time sufficient to produce a second particulate resin. The thermal stability of the second particulate resin is superior to that of its respective first particulate resin is superior to that of its respective first particulate resin. Moreover, the molecular weight of the second particulate resin is greater than that of its respective first particulate resin.Type: GrantFiled: November 16, 1988Date of Patent: January 9, 1990Assignee: Phillips Petroleum CompanyInventors: Jon F. Geibel, Roger G. Gaughan, Michael D. Cliffton
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Patent number: 4886871Abstract: Disclosed herein are a melt-stable poly(arylene thioether-ketone) having predominant recurring units of the formula ##STR1## and having a melting point, Tm of 310.degree.-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., and a reduced viscosity of 0.2-2 dl/g as measured at 25.degree. C. and a polymer concentration of 0.5 g/dl in 98 wt. % sulfuric acid as well as a production process of the poly(arylene thioether-ketone). The poly(arylene thioether-ketone) has melt stability so that conventional melt processing techniques can be applied easily. The poly(arylene thioether-ketone) is a highly-crystalline polymer whose density is at least 1.34 g/cm.sup.3 when annealed at 280.degree. C. for 30 minutes.Type: GrantFiled: May 19, 1989Date of Patent: December 12, 1989Assignee: Kureha Kagaku Kogyo K. K.Inventors: Yoshikatsu Satake, Takashi Kaneko, Yutaka Kobayashi, Yo Iizuka, Takayuki Katto, Zenya Shiiki
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Patent number: 4873283Abstract: Disclosed herein is a molded or formed poly(arylene thioether-ketone) article made of a thermoplastic material which comprises 100 parts by weight of a melt-stable poly(arylene thioether-ketone) (PTK) and if desired, up to 100 parts by weight of at least one of thermoplastic resins and/or up to 300 parts by weight of at least one of fibrous fillers and/or least one of inorganic fillers. The PTK has predominant recurring units of the formula ##STR1## wherein the --CO-- and --S-- are in the para position to each other, and has a melting point, Tm of 310.degree.-380.degree. C., a residual melt cyrstallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., and a reduced viscosity of 0.2-2 dl/g as determined by viscosity measurement at 25.degree. C. and a polymer concentration of 0.5 g/dl in 98 percent by weight sulfuric acid.Type: GrantFiled: May 12, 1988Date of Patent: October 10, 1989Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yoshikatsu Satake, Yo Iizuka, Toshitaka Kouyama, Takayuki Katto, Zenya Shiiki
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Patent number: 4866155Abstract: Polyesters of 4,4'bis[2-(4-hydroxyphenyl)hexafluoroisopropyl]diphenyl ether having high transparency, high solvent solubility and excellent melt processability are prepared. They possess high thermal and radiation stability and are useful in the preparation of protective films, protective paints, films, fibers, diffusion membranes and shaped articles where high service temperature and radiation resistance are desired.Type: GrantFiled: November 24, 1987Date of Patent: September 12, 1989Assignee: Hoechst Celanese CorporationInventors: Werner H. Mueller, Dinesh N. Khanna
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Patent number: 4864015Abstract: A method is provided for making 9,10-dithiaanthracene-2,3,6,7-tetracarboxylic acid dianhydride. Polyimides having improved oxidative stability also are provided which can be made intercondensing organic diamine and the aforementioned dianhydride or a dianhydride mixture.Type: GrantFiled: November 21, 1988Date of Patent: September 5, 1989Assignee: General Electric CompanyInventors: James A. Cella, Deborah A. Haitko
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Patent number: 4857629Abstract: A process for preparing a copoly(arylene sulfide) corresponding to the structure[(--A--S--).sub.1-x (--A--S--S--).sub.x ].sub.nwherein x is in the range of 0.5 to 0.001 by reacting a mixture of a diiodoaromatic compound and elemental sulfur in the absence of a basic material and in the presence of a catalytic amount of iron.Type: GrantFiled: February 13, 1989Date of Patent: August 15, 1989Assignee: Eastman Kodak CompanyInventors: Mark Rule, David R. Fagerburg, Joseph J. Watkins
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Patent number: 4855393Abstract: A process for preparing a copoly(arylene sulfide) corresponding to the structure[(--A--S--).sub.1-x (--A--S--S--).sub.x ].sub.nwherein x is in the range of 0.5 to 0.001 by reacting a mixture of a diiodoaromatic compound and elemental sulfur in the absence of a basic material.Type: GrantFiled: February 13, 1989Date of Patent: August 8, 1989Assignee: Eastman Kodak CompanyInventors: Mark Rule, David R. Fagerburg, Joseph J. Watkins, Jerry S. Fauver
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Patent number: 4845190Abstract: In a process for preparing polyarylene sulfides by reacting a dihalo-aromatic compound with a sulfur source in an organic amide solvent in the presence of an alkali metal salt of carboxylic acid as a polymerization aid or assistant, a specific class of carboxylic acids are employed for preparing the alkali metal salt polymerization aid. The specific carboxylic acids are of the general formula: R(COOH).sub.n (wherein R is a C.sub.1 -C.sub.20 organic radical and n is an integer not less than 1) and have a solubility of not less than 3 g/100 ml in ethanol at 20.degree. C. Use of such a carboxylic acid in the process permits the recovery thereof from the polymerization mixture to be effected with significantly improved efficiency.Type: GrantFiled: December 24, 1987Date of Patent: July 4, 1989Assignees: Tosoh Corporation, Toso Susteel Co., Ltd.Inventors: Hiroshi Inoue, Toshikazu Kato, Noriaki Emura
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Patent number: 4826956Abstract: A process for producing a copoly(arylene sulfide) corresponding to the structure[--A--S--).sub.1-x (--A--S--S--).sub.x ].sub.nwherein A is a divalent substituted or unsubstituted aromatic radical, x is in the range of 0.5 to 0.001 and n is at least 200, comprising reacting within a reaction zone a mixture of a diiodoaromatic compound and elemental sulfur at a polymer producing temperature wherein the reaction zone contains an oxygen-containing gas flowing at a rate in the range of 0.001 to 0.08 ft3/hr/mol of oxygen per mole of sulfur.Type: GrantFiled: May 20, 1988Date of Patent: May 2, 1989Assignee: Eastman Kodak CompanyInventors: David R. Fagerburg, Joseph J. Watkins, Paul B. Lawrence, Mark Rule
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Patent number: 4826906Abstract: Disclosed herein is a poly(arylene thioether-ketone) composition improved in melt stability and crystallinity, which comprises (A) 100 parts by weight of a melt-stable poly(arylene thioether-ketone) (PTK) and (B) 0.1-30 parts by weight of at least basic compound selected from the group consisting of the hydroxides, oxides and aromatic carboxylic acid salts of Group IIA metals of the periodic table other than magnesium and the hydrocarbyl oxides, aromatic carboxylic acid salts, carbonates, hydroxides, phosphates and borates of Group IA metals of the periodic table. The phosphates and borates include condensation products. The PTK has predominant recurring units of the formula ##STR1## and having a melting point, Tm of 310.degree.-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization peak-temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C. and a reduced viscosity of 0.2-2 dl/g.Type: GrantFiled: June 17, 1988Date of Patent: May 2, 1989Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yoshikatsu Satake, Ken Kashiwadate, Yo Iizuka, Toshitaka Kouyama, Takayuki Katto, Zenya Shiiki
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Patent number: 4824933Abstract: This invention relates to a process for the preparation of polyarylene sulphides with reduced crystallization temperature.Type: GrantFiled: October 28, 1987Date of Patent: April 25, 1989Assignee: Bayer AktiengesellschaftInventors: Edgar Ostlinning, Ernst-Ulrich Dorf
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Patent number: 4818809Abstract: Aromatic sulfide amide polymers composed of a repeating unit having the formula (I) and a repeating unit having the formula (II) below, having an inherent viscosity ranging from 0.02 to 10 dl/g. ##STR1## wherein, Ar.sup.1, Ar.sup.2, Ar.sup.3 and Ar.sup.4 are same or different aromatic rings and R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: September 14, 1987Date of Patent: April 4, 1989Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Tomohiro Ishikawa, Yozo Kondo
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Patent number: 4812552Abstract: A process and product produced therefrom for preparing a melt stable, high molecular weight poly(arylene sulfide ketone) from the addition of water to a reaction mixture containing a polyhalobenzophenone and an alkali metal sulfide. The water being present in a molar ratio of about 4.5:1 to about 8:1 with respect to the alkali metal sulfide.Type: GrantFiled: April 15, 1987Date of Patent: March 14, 1989Assignee: Phillips Petroleum CompanyInventors: Michael D. Cliffton, Jon F. Geibel
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Patent number: 4812539Abstract: Disclosed herein is a process for producing a medium- or high-molecular-weight polyarylene sulfide which comprises subjecting an alkali metal sulfide, a dihalo aromatic compound and optionally, small amount of tri- or higher polyhalo aromatic compound to dehalogenation and sulfidation reaction at a temperature of from 235.degree. to 280.degree. C. in the presence of a water in amount of from 0.5 to 5 mol per 1 kg of an aprotic organic polar solvent until the conversion of said dihalo aromatic compound reaches from 70 to 98 mol %, thereby forming a polyarylene sulfide prepolymer having a melt viscosity of from 5 to 300 poise (as measured at 310.degree. C. under a shear rate of 200 sec.sup.-1), adding water to the resultant reaction mixture containing the polyarylene sulfide prepolymer so that from 6 to 15 mol of water is present per 1 kg of said solvent, and then continuing the reaction at a temperature of from 240.degree.-290.degree. C.Type: GrantFiled: July 31, 1987Date of Patent: March 14, 1989Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Yo Iizuka, Takao Iwasaki, Takayuki Katto, Zenya Shiiki
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Patent number: 4795799Abstract: A process is provided for the production of aromatic sulfide/ketone polymers which comprises contacting under suitable polymerization conditions: (1) at least one dihaloaromatic ketone, (2) at least one organic amide, (3) at least one alkali metal hydrosulfide, (4) water, and (5) at least one member selected from the group consisting of (a) alkali metal carbonates and (b) mixtures of alkali metal carbonate with alkali metal hydroxide.Type: GrantFiled: September 8, 1987Date of Patent: January 3, 1989Assignee: Phillips Petroleum CompanyInventor: James W. Cleary
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Patent number: 4786694Abstract: Described are crystalline block copolymers displaying high glass transition temperatures, excellent mechanical properties, excellent chemical and thermal stability, and good melt processability. These block polymers contain segments of crystalline poly(aryl ether ketones).Type: GrantFiled: April 16, 1987Date of Patent: November 22, 1988Assignee: Amoco CorporationInventors: Robert A. Clendinning, James E. Harris, George T. Kwiatkowski, Lee P. McMaster, Markus Matzner, Paul A. Winslow
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Patent number: 4783520Abstract: The method of preparing a thermoplastic polyarylether polymer which comprises reacting a first monomer composition comprising an activated dihalobenzenoid compound and a dihydroxydiphenyl aliphatic monomer in a molar ratio of dihalobenzenoid compound to dihydroxybenzenoid compound of at least 1.2 to 1, adding to the product a second monomer composition comprising a dihydroxybenzenoid compound comprising at least one compound which is free of aliphatic moieties and polymerizing.Type: GrantFiled: July 1, 1987Date of Patent: November 8, 1988Assignee: Amoco CorporationInventors: Donald R. Kelsey, Bernard Cooker, Robert A. Clendinning, Robert Barclay, Jr., George T. Kwiatkowski
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Patent number: 4783522Abstract: An aromatic polythioetherimide having a recurring unit of the following general formula (II): ##STR1## wherein --Ar--, which may be the same or different in the polymer, each represents a divalent aromatic residue and ##STR2## which may be the same or different in the polymer, each represents ##STR3## The aromatic polythioetherimides can be melt-molded, are excellent in the balance of mechanical properties and heat resistance, and can be widely used for parts in the electric and electronic fields, housings, automobile parts, aircraft interior parts, sliding parts, gears, cams, insulating materials, heat-resistant films, heat-resistant varnishes, heat-resistant fibers, etc., and preferably can be used as an engineering plastic for gears, cams, etc., and a heat-resistant insulating film material for electronic hardwares.Type: GrantFiled: July 11, 1986Date of Patent: November 8, 1988Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Mitsutoshi Aritomi, Makoto Terauchi
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Patent number: 4778859Abstract: A curable composition comprising (a) a curable polyimide soluble in organic solvents and (b) a polymerization initiator as essential components, said polyimide consisting of recurring units represented by the formula ##STR1## wherein, each of X, X.sub.1, X.sub.2, X.sub.3 and X.sub.4 is a tetravalent carbocyclic or heterocyclic residue, each of Y.sub.1, Y.sub.2, and Y.sub.3 is a divalent carbocylic or heterocyclic residue, at least one of Z.sub.1 and Z.sub.2 is a residue having a reactive carbon-carbon double bond, and each of l, m, and n is an integer from 0 to 20, preferably from 0 to 10. The polyimide may include (a) polyacrylate compounds (b) bis-imide compounds (c) photosensitive polyimide precursors (d) oxime initiators (e) a 3 component sensitizer of a phenone compound, a mercapto compound, and an arylamine-alkanol, or mixtures of a,b,c,d, and e.Type: GrantFiled: April 28, 1986Date of Patent: October 18, 1988Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hideo Ai, Akihiko Ikeda, Kan-ichi Yokota
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Patent number: RE33079Abstract: Polyimides are prepared from acetylene substituted polyimide oligomers via an addition polymerization reaction which involves homopolymerization. These polymers exhibit low void content when cured and possess superior thermal stability characteristics and physical properties such as structural strength. One of their unique properties is their ability to be processed into useful articles at moderate pressures and temperatures.Type: GrantFiled: March 5, 1979Date of Patent: October 3, 1989Assignee: Hughes Aircraft CompanyInventors: Norman Bilow, Abraham L. Landis, Leroy J. Miller
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Patent number: RE33545Abstract: A process, and product produced therefrom, for preparing a high molecular weight poly(arylene sulfide ketone) from the reaction product of an alkali metal bisulfide with an alkali metal hydroxide, employing molar excess of alkali metal bisulfide with respect to the alkali metal hydroxide. A process, and product produced therefrom, for preparing a high molecular weight poly(arylene sulfide ketone) employing an alkali metal sulfide and an alkali metal hydrosulfide, wherein the alkali metal .[.sulfide.]. .Iadd.hydrosulfide .Iaddend.is added in a molar excess with respect to the alkali metal .[.hydrosulfide.]. .Iadd.sulfide.Iaddend..Type: GrantFiled: July 14, 1989Date of Patent: February 26, 1991Assignee: Phillips Petroleum CompanyInventor: Roger G. Gaughan