From Monomer Containing Sulfur Atom As Part Of A Heterocyclic Ring Patents (Class 526/256)
  • Patent number: 5532328
    Abstract: The invention relates to a process for the preparation of a polymer from heterocyclic monomer units. The process according to the invention is characterized in that polymerization takes place in the presence of a sulphur-containing reagent.It has been found that the process according to the invention can be used to prepare polymers that can readily be processed, either in solution or in the melt. It has further been found that the reaction time of the reaction that takes place is short, while also the efficiency of the reaction is good. In the process according to the invention use can be made of monomer units that are thermostable. Such monomer units are easy to synthesize and easy to keep.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: July 2, 1996
    Assignee: DSM N.V.
    Inventors: Ivan A. L. Hoogmartens, Joannes M. J. V. Gelan, Dirk J. M. Vanderzande, Peter E. Froehling
  • Patent number: 5527434
    Abstract: Provided is a method for preparing a conductive polymer which is highly transparent to visible light in at least one of its conductive and non-conductive states. A solution containing a monomer component and an electrolyte is introduced into an electrochemical cell and subjected to polymerization by cyclic voltammetry. The solution is maintained at a temperature within a range of from 0.degree. to -40.degree. C. inclusive. Prior to the polymerization, cyclic voltammetry is firstly performed at a potential below that at which anodic or cathodic polymerization may take place, anodic and cathodic limits (A) and (B) being held at respective values. A trace of current/voltage is monitored until the trace becomes stable, and thereafter the value of the limit (B) is progressively increased until the said value reaches a critical potential having a magnitude at which anodic or cathodic polymerization is initiated.
    Type: Grant
    Filed: July 18, 1994
    Date of Patent: June 18, 1996
    Assignee: The University of Newcastle Upon Tyne
    Inventors: Andrew Hamnett, Paul A. Christensen, Daniel C. Read
  • Patent number: 5510438
    Abstract: The present invention involves monomeric compounds having the structure: ##STR1## Substituents W and Z are independently --CN, --NO.sub.2, -aryl, -aryl-V, --COX, SO.sub.2 R, --H, or -alkyl. Substituent X is --OR, or --NR,R where R and R.sup.1 are independently -alkyl or --H. Substituent V is -halide, --NO.sub.2, --CN, --SO.sub.2 R, or --COX. At least one of W and Z is --NO.sub.2, --SO.sub.2 R, --CN, --COX or -aryl-V. In one preferred embodiment substituents W and Z are both --CN. In another preferred embodiment, substituent X is --NO.sub.2 or --CN and substituent Z is --C.sub.6 H.sub.4 NO.sub.2. These monomers are polymerized to form low bandgap polymers.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: April 23, 1996
    Assignee: Board of Regents, The University of Texas System
    Inventors: John P. Ferraris, Tim L. Lambert, Santiago Rodriguez
  • Patent number: 5510456
    Abstract: A polymer represented by the following formula (III) ##STR1## wherein R.sub.1 and R.sub.2 each independently represents H, a straight or branched alkyl group or alkoxy group having 1 to 20 carbon atoms, X is S, O, or NR.sub.3, R.sub.3 represents a straight or branched akyl group having 1 to 6 carbon atoms or a phenyl group, Y represents R.sub.4 S.sup.+ R.sub.5 M.sup.- or OR.sub.6, R.sub.4 and R.sup.5 each independently represent a straight or branched alkyl group having 1 to 5 carbon atoms, or form a heterocyclic ring together with sulfur, and M.sup.- is an anion, R.sub.6 represents H or a straight or branched alkyl group having 1 to 10, m is 1 to 2, and n represents a degree of polymerization and is a value larger than 5.
    Type: Grant
    Filed: June 16, 1994
    Date of Patent: April 23, 1996
    Assignee: Showa Denko K. K.
    Inventors: Reiko Ichikawa, Yoshiaki Ikenoue, Fred Wudl
  • Patent number: 5461166
    Abstract: Disclosed are a conductive thienyl derivative monomolecular film covalently bonded to a substrate surface and method of manufacturing the same, and a silicon compound comprising 3-thienyl groups (thiophene derivative) used for forming the conductive monomolecular film and a method of manufacturing the same. A monomolecular ultrathin film comprising 3-thienyl groups and silicon groups is formed in the invention. The silicon compound used for forming the film is provided by reacting .omega.-(3-thienyl)-1-alkene compound to a monosilane derivative compound, in which three out of four hydrogen atoms of monosilane are replaced with halogen or alkoxy groups, in the presence of a transition metal catalyst. A substrate is dipped and held in a nonaqueous solution of the above-noted compound, thus chemically bonding the monomolecular film to the substrate surface. Furthermore, a thienyl derivative ultrathin film is formed by the electrolytic or catalytic polymerization of the monomolecular film.
    Type: Grant
    Filed: February 3, 1995
    Date of Patent: October 24, 1995
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Norihisa Mino, Kazufumi Ogawa, Toshinobu Ishihara, Mikio Endo, Tohru Kubota, Kazuyuki Asakura
  • Patent number: 5461131
    Abstract: Azo dye polymers useful in nonlinear optics contain as characteristic monomer units radicals of the formulae I, II, III and IV ##STR1## where D is the radical of a heterocyclic diazo component,R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.6 -alkyl or substituted or unsubstituted C.sub.1 -C.sub.6 -alkoxy, and R.sup.2 may also be C.sub.1 -C.sub.4 -alkanoylamino,R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl or C.sub.3 -C.sub.4 -alkenyl,R.sup.4 is hydrogen, deuterium, methyl, trideuterated methyl or chlorine,R.sup.5 is hydrogen or deuterium,Y.sup.1 and Y.sup.2 are each substituted or unsubstituted C.sub.2 -C.sub.10 -alkylene,W is oxygen, imino or C.sub.1 -C.sub.4 -alkylimino, andX is hydroxyl, substituted or unsubstituted C.sub.1 -C.sub.6 -alkoxy, phenoxy, amino or mono- or di(C.sub.1 -C.sub.4 -alkyl)amino,and have an average molecular weight of from 1,000 to 100,000.
    Type: Grant
    Filed: February 24, 1995
    Date of Patent: October 24, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Wiesenfeldt, Sabine Gruettner-Merten, Ruediger Sens, Karl-Heinz Etzbach, Heike Kilburg
  • Patent number: 5436306
    Abstract: Methine or azamethine dye polymers useful in nonlinear optics contain as characteristic monomer units radicals of the formulae I, II, III and IV ##STR1## where G is a divalent organic radical,Z is nitrogen or CH,R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.6 -alkyl or substituted or unsubstituted C.sub.1 -C.sub.6 -alkoxy,R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl or C.sub.3 -C.sub.4 -alkenyl,R.sup.4 is hydrogen, deuterium, methyl, trideuterated methyl or chlorine,R.sup.5 is hydrogen or deuterium,Y.sup.1 and Y.sup.2 are each C.sub.2 -C.sub.10 -alkylene,E is oxygen, imino or C.sub.1 -C.sub.4 -alkylimino, andX is hydroxyl, substituted or unsubstituted C.sub.1 -C.sub.6 -alkoxy, phenoxy, amino or C.sub.1 -C.sub.4 -mono- or -dialkylamino, andthe ring A can be benzofused, and have an average molecular weight of from 1,000 to 100,000.
    Type: Grant
    Filed: June 29, 1994
    Date of Patent: July 25, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Etzbach, Ruediger Sens, Heike Kilburg
  • Patent number: 5434231
    Abstract: Azo dye polymers useful in nonlinear optics contain as characteristic monomer units radicals of the formulae I, II, III and IV ##STR1## where D is the radical of a heterocyclic diazo component,R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.6 -alkyl or substituted or unsubstituted C.sub.1 -C.sub.6 -alkoxy, and R.sup.2 may also be C.sub.1 -C.sub.4 -alkanoylamino,R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl or C.sub.3 -C.sub.4 -alkenyl,R.sup.4 is hydrogen, deuterium, methyl, trideuterated methyl or chlorine,R.sup.5 is hydrogen or deuterium,Y.sup.1 and Y.sup.2 are each substituted or unsubstituted C.sub.2 -C.sub.10 -alkylene,W is oxygen, imino or C.sub.1 -C.sub.4 -alkylimino, andX is hydroxyl, substituted or unsubstituted C.sub.1 -C.sub.6 -alkoxy, phenoxy, amino or mono- or di(C.sub.1 -C.sub.4 -alkyl)amino,and have an average molecular weight of from 1,000 to 100,000.
    Type: Grant
    Filed: June 24, 1993
    Date of Patent: July 18, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Wiesenfeldt, Sabine Gruettner-Merten, Ruediger Sens, Karl-Heinz Etzbach, Heike Kilburg
  • Patent number: 5430073
    Abstract: The invention relates to a process for preparing a polymer in which in situ polymerization of monomers takes place in the presence of a catalyst, in which the monomers are obtained by in situ activation of precursor monomers.According to the invention a premature polymerization is avoided, but polymerization only starts at the desired moment.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: July 4, 1995
    Assignee: DSM, N.V.
    Inventors: Hans K. Van Dijk, Ronald M. A. M. Schellekens, Markus J. H. Bulters, Olav M. Aagaard, Gerard P. De Vries, Matthias J. G. Brouns
  • Patent number: 5395556
    Abstract: Base polymers devoid of non-linear optical properties exhibiting second order non-linear optical properties after the covalent attachment of tricyanovinyl groups to pendant side chains of the base polymer. Methods of preparing a polymer having second order non-linear optical properties by reacting the base polymers of the present invention with tetracyanoethylene in a basic solvent at elevated temperatures.
    Type: Grant
    Filed: October 9, 1991
    Date of Patent: March 7, 1995
    Assignee: Enichem S.p.A.
    Inventors: Kevin J. Drost, Pushkara R. Varanasi, Kwan-Yue A. Jen, Michael A. Drzewinski
  • Patent number: 5385956
    Abstract: The method concerns preparing a polymer composition containing an electrically conductive polymer which is formed, in the presence of a catalyst, from polymerizable monomer units that are converted from non-polymerizable precursor monomers with the aid of a sufficiently energy-intense light source. In this method according to the invention is that the precursor monomers have a structure according to formula (I). The method according to the invention makes it possible to very easily and rapidly, and thus economically, prepare a polymer composition containing an electrically conductive polymer. Furthermore, the method according to the invention permits a polymer composition to be produced that contains an electrically conductive polymer in specifically pre-selected areas.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: January 31, 1995
    Assignee: DSM N.V.
    Inventors: Ronald M. A. M. Schellekens, Hans K. Van Dijk
  • Patent number: 5384378
    Abstract: Copolymers with non-linear optical properties, which contain or are composed of repeating units of the formula (I) ##STR1## where D is an electron donor,A is an electron acceptor,R.sup.1, R.sup.2, R.sup.3 and R.sup.4 can be the same as or different from one another, and are each H, alkyl, cycloalkyl, or R.sup.3 and R.sup.4 are each CN, NO.sub.2 or CHO, or R.sup.1 forms with R.sup.2, or R.sub.3 forms with R.sup.4, a fused-on ring,X is CH and/or N,m is an integer from 2 to 11, andR is hydrogen or methyl,and repeating units of at least one of the formulae (II), (III) and (IV) ##STR2## are suitable for the production of optical components.
    Type: Grant
    Filed: September 21, 1993
    Date of Patent: January 24, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Etzbach, Stefan Beckmann, Oskar Nuyken, Peter Strohriegl, Harry Mueller
  • Patent number: 5380807
    Abstract: Polycondensation of, for example, squaric acid with a benzodihydropyrrole, benzodithiazole, neocuproine, terthienyl or an aromatic diamine gives a semiconductive alternating copolymer having a small band gap. It is alternatively possible to use croconic acid or 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone instead of squaric acid.
    Type: Grant
    Filed: January 8, 1993
    Date of Patent: January 10, 1995
    Assignee: U.S. Philips Corporation
    Inventors: Edsko E. Havinga, Wolter Ten Hoeve, Hans Wijnberg
  • Patent number: 5328961
    Abstract: Electrically conductive polythiophenecarbonyl polymer networks are provided comprising conjugated crosslinks between polythiophenecarbonyl polymer segments of the network. The network can be formed by crosslinking carbonyl functional polythiophenecarbonyl polymers, such as by self-crosslinking condensation reaction or crosslinking condensation reaction with conjugated diylide and/or conjugated polyamine. The carbonyl functional polythiophenecarbonyl polymers can be prepared by polymerization, such as by electropolymerization of carbonyl functional thiophene monomers (the carbonyl functionality generally being protected during polymerization) and, optionally, suitable conjugated copolymerization monomers such as thiophene, pyrrole and/or carbonyl functional pyrrole.
    Type: Grant
    Filed: January 7, 1993
    Date of Patent: July 12, 1994
    Assignee: Ford Motor Company
    Inventors: Giuseppe Rossi, Susan M. Ward, Henk van Oene, Joseph W. Holubka
  • Patent number: 5314976
    Abstract: Conjugated conductive polymers which are photo-responsive upon ultra-violet light or visible light irradiation are prepared from copolymerization of photo-responsive groups containing heterocyclic monomers and 3-substituted heterocyclic monomers with the substituent containing a flexible segment like an alkyl group, ethoxyl group or siloxane group. The conductivity of the polymer can be controlled reversibly by irradiation of light and so can be used in optical-electronic applications or a production of detectors.
    Type: Grant
    Filed: August 10, 1993
    Date of Patent: May 24, 1994
    Assignee: National Science Council
    Inventors: Show-An Chen, Chien-Hsiun Liao
  • Patent number: 5286414
    Abstract: A coating composition comprising a soluble oligomer of substituted thiophenes and, where appropriate, a soluble polymer gives, applied from the solution in a dipolar aprotic solvent, highly adherent electroconductive coatings on nonconductive or semiconductive materials. In this way, films and fibers having an antistatic finish and moldings for electronics and electrics can be produced.
    Type: Grant
    Filed: May 24, 1993
    Date of Patent: February 15, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Kampf, Michael Feldhues
  • Patent number: 5279768
    Abstract: The invention relates to a process for the preparation of electrically conductive polymers derived from 3-alkylthiophenes by chemical polymerization of the 3-alkylthiophene by means of a ferric salt, an alkyl halide and water.The invention also relates to electrically conductive devices containing the poly(3-alkylthiophenes) obtained and a thermoplastic polymer.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: January 18, 1994
    Assignee: Solvay & Cie (Societe Anonyme)
    Inventors: Elise Destryker, Claude Franquinet, Etienne Hannecart
  • Patent number: 5274058
    Abstract: The present invention involves monomeric compounds having the structure: ##STR1## Substituents W and Z are independently --CN, --NO.sub.2, -aryl, -aryl-V, --COX, SO.sub.2 R, --H, or -alkyl. Substituent X is --OR, or --NR,R where R and R.sup.1 are independently -alkyl or --H. Substituent V is -halide, --NO.sub.2, --CN, --SO.sub.2 R, or --COX. At least one of W and Z is --NO.sub.2, --SO.sub.2 R, --CN, --COX or -aryl-V. In one preferred embodiment substituents W and Z are both --CN. In another preferred embodiment, substituent X is --NO.sub.2 or --CN and substituent Z is --C.sub.6 H.sub.4 NO.sub.2. These monomers are polymerized to form low bandgap polymers.
    Type: Grant
    Filed: September 12, 1991
    Date of Patent: December 28, 1993
    Assignee: Board of Regents, The University of Texas System
    Inventors: John P. Ferraris, Tim L. Lambert, Santiago Rodriguez
  • Patent number: 5272218
    Abstract: Disclosed are polymers which contain NLO dye moieties based upon a barbituric acid group, a thiobarbituric acid group or a 1,3-bis(dicyanomethylene)indan-2-ylidene group. These polymers, after poling, are useful in NLO elements in devices employing nonlinear optics. Also disclosed are various intermediates used in making such polymers.
    Type: Grant
    Filed: August 21, 1992
    Date of Patent: December 21, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Lap-Tak A. Cheng, Wilson Tam
  • Patent number: 5272234
    Abstract: Conjugated conductive polymers which are photo-responsive upon ultra-violet light or visible light irradiation are prepared from copolymerization of photo-responsive groups containing heterocyclic monomers and 3-substituted heterocyclic monomers with the substituent containing a flexible segment like an alkyl group, ethoxyl group or siloxane group. The conductivity of the polymer can be controlled reversibly by irradiation of light and so can be used in optical-electronic applications or a production of detectors.
    Type: Grant
    Filed: April 13, 1992
    Date of Patent: December 21, 1993
    Assignee: National Science Council
    Inventors: Show-An Chen, Chien-Hsiun Liao
  • Patent number: 5264507
    Abstract: Azo dye polymers useful in nonlinear optics contain as characteristic monomer units radicals of the formulae I, II, III and IV ##STR1## where D is the radical of a heterocyclic diazo component,R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.6 -alkyl or substituted or unsubstituted C.sub.1 -C.sub.6 -alkoxy, and R.sup.2 may also be C.sub.1 -C.sub.4 -alkanoylamino,R.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl or C.sub.3 -C.sub.4 -alkenyl,R.sup.4 is hydrogen, deuterium, methyl, trideuterated methyl or chlorine,R.sup.5 is hydrogen or deuterium,Y.sup.1 and Y.sup.2 are each substituted or unsubstituted C.sub.2 -C.sub.10 -alkylene,W is oxygen, imino or C.sub.1 -C.sub.4 -alkylimino, andX is hydroxyl, substituted or unsubstituted C.sub.1 -C.sub.6 -alkoxy, phenoxy, amino or mono- or di(C.sub.1 -C.sub.4 -alkyl)amino,and have an average molecular weight of from 1,000 to 100,000.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: November 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Wiesenfeldt, Sabine Gruettner-Merten, Ruediger Sens, Karl-Heinz Etzbach, Heike Kilburg
  • Patent number: 5254648
    Abstract: The invention relates to a process for the preparation of electrically conducting polymers based on polythiophenes by chemical polymerization of thiophene by means of a ferric salt, an alkyl halide and water.The invention also relates to the electrically conducting devices containing the polythiophenes obtained and a thermoplastic polymer.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: October 19, 1993
    Assignee: Solvay & cie (Societe Anonyme)
    Inventors: Elise Destryker, Etienne Hannecart, Claude Franquinet
  • Patent number: 5243004
    Abstract: An electron conductive high molecular compound comprising an ethylenic repeating unit having an electron conductive moiety composed of a compound comprising at least one repeating unit of an aniline compound or a heterocyclic compound as a repeating unit at the side chain and further having a repeating unit of an oxyalkylene group at the linked portion of the repeating unit of the electron conductive moiety and the main chain thereof.
    Type: Grant
    Filed: March 19, 1991
    Date of Patent: September 7, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Eiji Funatsu, Tadahiko Kubota, Shigetoshi Ono
  • Patent number: 5241027
    Abstract: A compound comprising 0.001 to 100 mole percent of a structural unit of the formula ##STR1## wherein W is --CMe.sub.2 -- or --Se--, R.sup.1 is C.sub.1 -C.sub.20 alkyl or aralkyl, R.sup.2 to R.sup.5 each represents H, C.sub.1 -C.sub.6 alkyl, etc., R.sup.6 and R.sup.7 each represents H, C.sub.1 -C.sub.6 alkyl, etc., X is O or S, provided that when W is --CMe.sub.2 --, X is S, and 0 to 99.999 mole percent of a structural unit of the formula ##STR2## wherein Y is H or Me and Z represents alkoxycarbonyl, phenyl, etc.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: August 31, 1993
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventor: Akira Miyashita
  • Patent number: 5233000
    Abstract: Polymers of pyrrole or copolymers of pyrrole are obtained having high surface area and low conductivity. Such polymers and copolymers are useful in forming catalysts.
    Type: Grant
    Filed: July 18, 1990
    Date of Patent: August 3, 1993
    Assignee: The Lubrizol Corporation
    Inventor: Richard Yodice
  • Patent number: 5225109
    Abstract: The invention relates to electrically conducting polymers which are obtainable as self-supporting films or composite bodies and which contain structural units which are derived from at least one monomer of the formula (I) ##STR1## wherein R.sup.1 represents a C.sub.1 -C.sub.12 -alkoxy group and R.sup.2 represents a C.sub.1 -C.sub.12 -alkyl group. The invention furthermore relates to a process for preparing said polymers by oxidative polymerization of at least one monomer of said formula (I). The polymers according to the invention may be used, in particular, for applications for which high chemical, mechanical or thermal stability simultaneously accompanied by high electrical conductivity is necessary and of advantage.
    Type: Grant
    Filed: February 9, 1989
    Date of Patent: July 6, 1993
    Assignee: Hoechst AG
    Inventors: Michael Feldhues, Gunther Kampf
  • Patent number: 5221786
    Abstract: The invention relates to a process for the preparation of electrically conducting polymers based on polythiophenes by chemical polymerization of thiophene by means of a ferric salt, an alkyl halide and water.The invention also relates to the electrically conducting devices containing the polythiophenes obtained and a thermoplastic polymer.
    Type: Grant
    Filed: June 14, 1991
    Date of Patent: June 22, 1993
    Assignee: Solvay & Cie (Societe Anonyme)
    Inventors: Elise Destryker, Etienne Hannecart, Claude Franquinet
  • Patent number: 5219492
    Abstract: The invention relates to a conductive polymer composite wherein the internally conductive polymer component consists of a polymer of a 3-substituted thiophene, the polymer being doped with a suitable electron acceptor or electron emitter compound. The polymer composite is prepared by processing in molten state by various methods such as extrusion molding, injection molding, compression molding, or sheet blowing, together with a suitable polymer matrix, to form a homogenous composite.
    Type: Grant
    Filed: July 9, 1992
    Date of Patent: June 15, 1993
    Assignee: Neste Oy
    Inventors: Jan-Erik Osterholm, Jukka Laakso, Sari Karjalainen, Pirjo Mononen
  • Patent number: 5213714
    Abstract: A coating composition comprising a soluble electroconductive polymer of substituted thiophenes and, if appropriate, a soluble non-conductive polymer produces, when applied from the solution in an aprotic solvent, highly adherent, electroconductive coatings on non-conductive or semiconducting materials. In this way, antistatic films and fibers and mouldings for the purposes of electronics and electrics can be produced.
    Type: Grant
    Filed: February 9, 1989
    Date of Patent: May 25, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Kampf, Michael Feldhues
  • Patent number: 5208306
    Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.
    Type: Grant
    Filed: August 7, 1992
    Date of Patent: May 4, 1993
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 5206321
    Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.
    Type: Grant
    Filed: October 3, 1991
    Date of Patent: April 27, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5204423
    Abstract: A process for the preparation of a polymer which is electrically conductive and which is based on polythiophene, the process including polymerizing thiophene in a reaction medium including thiophene, from 2.5 to 20 moles of an anhydrous ferric salt per mole of thiophene, from 0.04 to 1 liter of an alkyl halide per gram of thiophene, and from 0.1 to 5% by weight of water introduced into the reaction medium based on the amount of alkyl halide.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: April 20, 1993
    Assignee: Solvay & Cie
    Inventors: Claude Franquinet, Etienne Hannecart, Elise Destryker
  • Patent number: 5204424
    Abstract: Electrically conductive polymers containing repeat units derived from five-membered aromatic heterocyclic monomers substituted, in the 3 position relative to the heteroatom, by an ether-type substituent linked to the heterocyclic ring by an alkylene radical containing at least two carbon atoms. The invention also relates to certain monomers enabling the above-mentioned conductive polymers to be obtained.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: April 20, 1993
    Assignee: Solvay S.A.
    Inventors: Jean Roncali, Robert Garreau, Didier Delabouglise, Marc Lemaire, Francis Garnier, Etienne Hannecart
  • Patent number: 5182316
    Abstract: A curable composition, the cure of which can be monitored optically, comprises at least one of a hydride curable silicone, an ethylenically unsaturated compound, and a cationically polymerizable monomer, and as cure monitor dibenzofulvene or derivative thereof. The cure monitor is a latent fluorophore which reacts under the cure conditions to form a UV-detectable fluorophore.The invention also provides a method for measuring degree of cure of a polymeric material which can be a coating or an article.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: January 26, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Robert J. DeVoe, Katherine A. Brown-Wensley, George V. D. Tiers
  • Patent number: 5182348
    Abstract: Compounds of the formula (1) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 have the meanings given in the description, and the other radicals have the following meanings:X, Y and Z denote identical or different divalent radicals --O--, --S--, --N(R.sup.9)-- or --C(R.sup.10).dbd.C(R.sup.11)--, with the proviso that at least one of the radicals, X, Y and Z is not a radical of the formula --C(R.sup.10).dbd.C(R.sup.11)--, and whereinR.sup.9 is a hydrogen atom, a branched or unbranched C.sub.1 - to C.sub.8 -alkyl radical or an optionally substituted phenyl radical, andR.sup.10 and R.sup.11 are, in each case, identical or different radicals which have one of the meanings of R.sup.1,R.sup.7 and R.sup.8 denote identical or different radicals, that is to say hydrogen atoms or C.sub.1 - to C.sub.6 -alkyl or phenyl radicals, andn, m and o denote identical or different integers with a value of from 1 to 10.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: January 26, 1993
    Assignee: Wacker-Chemie GmbH
    Inventors: Hermann Braeunling, Richard Becker, Georg Bloechl
  • Patent number: 5164464
    Abstract: Thermosettable vinyl ester resin compositions are prepared from polyepoxide compounds, optionally, monoepoxide compounds, at least one of which contains a mesogenic or rigid rodlike moiety and a monounsaturated monocarboxylic acid. These vinyl ester resins can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: November 17, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 5164111
    Abstract: The invention relates to polymerizable liquid-crystal materials and to polymer materials which exhibit liquid-crystal phases and which contain, attached directly or via a spacer, mesogenic groups in which at least one transversely polarizing structural element of the formulae I to X, defined in claim 1, is present.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: November 17, 1992
    Assignee: Merck Patent Gesellschaft mit beschraenkter Haftung
    Inventors: Dieter Dorsch, Rudolf Eidenschink, Andreas Wachtler, Bernhard Rieger, Heino Finkelmann
  • Patent number: 5162473
    Abstract: This invention relates to electrically conductive and non-conductive forms of poly(heterocyclic vinylenes) and to solutions of same. Another aspect of this invention relates to novel precursor polymers which can be converted into the poly(heterocyclic vinylenes) of this invention.
    Type: Grant
    Filed: July 7, 1987
    Date of Patent: November 10, 1992
    Assignee: Allied-Signal
    Inventors: Kwan-Yue A. Jen, Ronald L. Elsenbaumer, Lawrence W. Shacklette
  • Patent number: 5162470
    Abstract: Novel conjugated stilbenylene polymers are disclosed having non-linear optical properties, and which can be converted to electrically conductive polymers. Such polymers are produced by reacting a novel bis-cycloalkylene sulfonium salt of 2,5-dimethyl stilbene, e.g. 2,5-(4' -methoxy)-stilbene dimethylene bis-(tetramethylene sulfonium bromide), with alkali metal hydroxide to form a cycloalkylene sulfonium salt precursor polymer, and then heating the precursor polymer under conditions to produce the stilbenylene vinylene polymer, e.g. poly(2,5-(4'-methoxy)stilbenylene vinylene).
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: November 10, 1992
    Inventor: John Stenger-Smith
  • Patent number: 5158707
    Abstract: The invention relates to the homogenization of mixtures of internally conductive polymers like 3-substituted polythiophene and matrix polymers. With an efficient homogenization the conductivity is improved when the portion of the conductive polymer is low. An efficient homogenization is achieved in the invention by mixing the internally conductive polymer with a monomer or by dissolving it into it, after which the monomer is polymerized. The plastic composites so obtained are used for several purposes in which conductivity is needed, such as EMI and ESD shielding.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: October 27, 1992
    Assignee: Neste Oy
    Inventors: Torvald Vestberg, Jukka Laakso, Jan-Erik sterholm, Ismo Lehtiniemi
  • Patent number: 5159030
    Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: October 27, 1992
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 5137799
    Abstract: An electrically conductive resist material is disclosed, comprising at least one polymer which is sensitive to ionizing radiation and a soluble electrically conductive oligomer or polymer. A process for producing the resist material is also described, comprising admixing an electrically conductive oligomer or polymer dissolved in a solvent to at least one polymer which is sensitive to ionizing radiation. The resist material is useful in preparing electron beam resists which prevent electrostatic charging and resultant electrostatic fields.
    Type: Grant
    Filed: February 2, 1990
    Date of Patent: August 11, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Guenther Kaempf, Michael Feldhues, Ude Scheunemann, Juergen Lingnau
  • Patent number: 5136049
    Abstract: The present invention relates to compounds of formula (I): ##STR1## in which A represents the same or different heteroaryl radicals and substituted heteroaryl radicals; B represents dihydroheteroarenediylidene radicals or substituted dihydroheteroarenediylidene radicals or radicals obtainable from these radicals by oxidation on at least one hetero atom; and R' and R" represent the same or different radicals, in particular hydrogen atoms, C.sub.1 - to C.sub.4 -alkyl radicals or radicals A, or cyano radicals, halogen atoms, radicals of the formula --COOR, or --OR, wherein R is a C.sub.1 - to C.sub.4 -alkyl radical, processes for preparing the same and polymers prepared therefrom.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: August 4, 1992
    Assignee: Wacker-Chemie GmbH
    Inventors: Michael Hanack, Gunter Hieber
  • Patent number: 5132049
    Abstract: Substituted thiophenes of the general formula: ##STR1## in which: R represents a hydrogen atom, a halogen atom or an aliphatic group containing from 1 to 4 carbon atoms,X represents a hydrogen atom or a fluorine atom,Y represents an at least partially fluorinated aliphatic or aromatic group,m represents an integer equal to or greater than 2, andn represents an integer such that 0.ltoreq.n.ltoreq.7.The invention also relates to the electrically conducting polymers containing recurring units derived from monomers chosen from the substituted thiophenes.
    Type: Grant
    Filed: December 4, 1989
    Date of Patent: July 21, 1992
    Assignee: Solvay & Cie (Societe Anonyme)
    Inventors: Robert Garreau, Jean Roncali, Marc Lemaire, Hafsa Korri, Francis Garnier, Etienne Hannecart
  • Patent number: 5130392
    Abstract: Radiation-sensitive polymers suitable for use in positive- and negative-working recording elements contain not only acid-labile groups but also onium salt groups having nonnucleophilic counterions in one and the same molecule.
    Type: Grant
    Filed: January 9, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhold Schwalm, Andreas Boettcher
  • Patent number: 5115057
    Abstract: Disclosed is an electron-conductive high polymer, which has at least (1) an ethylenic repeating unit having an electron-conductive site comprising at least one of aniline compounds and heterocyclic compounds as the repeating unit in the side chain and (2) an ethylenic repeating unit having an anionic group in the side chain and/or an ethylenic repeating unit having a repeating unit of an oxyalkylene group in the side chain. As having excellent electroconductivity, mechanical strength and shapability, the high polymer is laminated with a solid polyelectrolyte or with a separator to prepare an electroconductive material usable as a battery material.
    Type: Grant
    Filed: July 5, 1990
    Date of Patent: May 19, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shigetoshi Ono, Eiji Funatsu
  • Patent number: 5111327
    Abstract: Substituted 3,4-dimethylenedioxythiophenes are provided. The substituted 3,4-dimethylenedioxythiophenes can be polymerized by chemical or electro-chemical means to produce polymers which are useful as EMI shielding and for making smart windows and switches.
    Type: Grant
    Filed: March 4, 1991
    Date of Patent: May 5, 1992
    Assignee: General Electric Company
    Inventors: Margaret L. Blohm, James E. Pickett, Paul C. VanDort
  • Patent number: 5110504
    Abstract: A polymer produced by removing an electrolytic ion from a polymer doped with the electrolytic ion possesses a nonlinear conductivity. An element made of this polymer, on exposure to a sine wave electric field, generates a higher harmonic wave.
    Type: Grant
    Filed: March 28, 1989
    Date of Patent: May 5, 1992
    Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventors: Kohzo Ito, Yoshikazu Tanabe, Masa-aki Sato, Kyoji Kaeriyama
  • Patent number: 5093033
    Abstract: The invention relates to intrinsically electrically conductive polymers, preferably oligomers, which, in the oxidized form, are completely soluble in dipolar aprotic solvents at room temperature and which contain structural units which are derived from at least one monomer of the formula (I) ##STR1## in which R.sup.1 is a C.sub.1 -C.sub.2 -alkoxy group or --O(CH.sub.2 CH.sub.2 O).sub.n CH.sub.3 with n=1 to 4 and R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.12 -alkyl group, a C.sub.1 -C.sub.12 -alkoxy group or --O(CH.sub.2 CH.sub.2 O).sub.n CH.sub.3 with n=1 to 4, or R.sup.1 and R.sup.2 together are --O(CH.sub.2).sub.m --CH.sub.2 or --O(CH.sub.2).sub.m --O-- with m=1 to 12. The invention also relates to a process for the preparation of these polymers by electrochemical polymerization of at least one monomer of this formula (I) in the presence of a conductive salt, the anode having a specific surface area of at least 0.01 m.sup.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: March 3, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Michael Feldhues, Thomas Mecklenburg, Peter Wegener, Gunther Kampf
  • Patent number: RE34919
    Abstract: The present invention relates to a number of innovative electrophilic substitution reactions involving 2,5-dithienylpyrrole (2,5-DTP). More specifically, these reactions are used in the synthesis of monomers for preparing functionalized conducting organic polymers.The electrophilic substitution reactions in this invention are accomplished under conditions not requiring the use of N-1 pyrrole blocking groups to direction reaction at the pyrrole C-3 position. This is because the steric bulk of the 2,5-dithienyl groups prevent N-acylation and therefore direct reactions with electrophiles at the pyrrole C-3 position.The reaction conditions chosen have also demonstrated a greater regioselectively towards functionalization at the pyrrole 3-position than the basic reaction conditions suggested in the prior art. This result may be explained by an activation of the pyrrole 3-position towards electrophilic substitution. This is attributed to an electron donating resonance contribution of the 2,5 thienyl groups.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: April 25, 1995
    Assignee: Miles Inc.
    Inventors: James P. Albarella, Nan-Horng Lin