WO1995033803A1 - Poly(esteramides) cristallins liquide thermotropiques - Google Patents

Poly(esteramides) cristallins liquide thermotropiques Download PDF

Info

Publication number
WO1995033803A1
WO1995033803A1 PCT/US1995/006364 US9506364W WO9533803A1 WO 1995033803 A1 WO1995033803 A1 WO 1995033803A1 US 9506364 W US9506364 W US 9506364W WO 9533803 A1 WO9533803 A1 WO 9533803A1
Authority
WO
WIPO (PCT)
Prior art keywords
monomer repeat
repeat unit
fiber
liquid crystalline
esteramide
Prior art date
Application number
PCT/US1995/006364
Other languages
English (en)
Inventor
Balaram Gupta
Matthew J. Bylicki
Original Assignee
Hoechst Celanese Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst Celanese Corporation filed Critical Hoechst Celanese Corporation
Priority to JP8500962A priority Critical patent/JPH10501277A/ja
Priority to EP95919897A priority patent/EP0764195A1/fr
Publication of WO1995033803A1 publication Critical patent/WO1995033803A1/fr

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/44Polyester-amides
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38Polymers
    • C09K19/3804Polymers with mesogenic groups in the main chain
    • C09K19/3809Polyesters; Polyester derivatives, e.g. polyamides

Definitions

  • This invention relates generally to thermotropic liquid crystalline polymers, and more specifically to liquid crystalline poly(esteramides) that have a high heat distortion temperature.
  • Thermotropic liquid crystalline polymers are well known in the art. They have excellent properties that make them useful in the manufacture of molded parts.
  • the strength of molded parts at elevated temperatures, as measured by the heat distortion temperature, is ultimately limited by the melting temperature of the polymers. Nevertheless, molded parts made from some polymers retain their physical integrity at temperatures close to the melting temperature. This may be characterized as the difference between the melting temperature of the polymer and the heat distortion temperature.
  • NDA 1,3-bis(trimethacrylate)-styrene resin
  • HQ 1 ,4-hydroquinone
  • TA terephthalic acid
  • HBA 4- hydroxybenzoic acid
  • BP 4,4'-biphenol
  • Thermotropic liquid crystalline poly(esteramides) that consist essentially of monomer repeat units I, II, III, IV, V and optional VI have an excellent combination of properties, where:
  • R and R' are alike or different and are selected from the group consisting of H, alkyl groups having 1 to 4 carbon atoms, fluoroalkyl groups having 1 to 4 carbon atoms, phenyl, and mixtures thereof.
  • Some of the hydrogen atoms on the aromatic rings of monomer repeat units I, II, III, IV, V and VI optionally may be replaced with one or more substituents selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, fluoroalkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, Cl, Br, F, I, aromatic groups having up to 7 carbon atoms and mixtures thereof.
  • alkyl groups having 1 to 4 carbon atoms include linear and branched alkyl groups, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl and tert-butyl.
  • Fluoroalkyl groups having 1 to 4 carbon atoms include linear and branched fluoroalkyl groups in which some or all of the hydrogen atoms have been replaced with fluorine.
  • Alkoxy groups having 1 to 4 carbon atoms can be linear or branched, such as methoxy, ethoxy, n-propoxy or isopropoxy.
  • Aromatic groups having up to 7 carbon atoms include phenyl and methyl substituted phenyl groups.
  • the liquid crystalline poly(esteramides) contain on a mole basis about 5% to about 80%) of monomer repeat unit I, about 5% to about 35%> of monomer repeat unit II, about 3%> to about 20%) of monomer repeat unit III, about 5% to about 35%) of monomer repeat unit IV, about 2%> to about 30%> of monomer repeat unit V, and 0 to about 10%> of monomer repeat unit VI.
  • These polymers show an exceptionally high heat distortion temperature compared with their melting temperature as measured by differential scanning calorimetry. They also show excellent impact resistance, as measured by their high notched Izod impact strength values.
  • monomer unit V is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • the aromatic rings of monomer units I, II, III, IV, V and VI are not substituted.
  • Monomer unit VI may be present in amounts up to about 10%>; its presence in the polymer is not necessary.
  • Preferred polymer compositions contain on a mole basis about 20% to about 60% of monomer repeat unit I, about 10% to about 30%> of monomer repeat unit II, about 5% to about 15%) of monomer repeat unit III, about 10% to about 30%o of monomer repeat unit IV, and about 5%> to about 20% of monomer repeat unit V.
  • the preferred poly(esteramides) may optionally also include up to about 10% of monomer repeat unit VI.
  • More preferred poly(esteramides) on a mole basis are composed of about 30%) to about 50%) of monomer repeat unit I, about 15%) to about 25%) of monomer repeat unit II, about 5% to about 15%» of monomer repeat unit III, about 20%> to about 30%> of monomer repeat unit IV, and about 5%> to about 10%> of monomer repeat unit V; monomer repeat unit VI is not present.
  • An especially preferred composition on a mole basis consists essentially of about 40%) of monomer unit I, about 20%> of monomer unit II, about 10%) of monomer unit III, about 25%) of monomer unit IV, and about 5%> of monomer unit V.
  • Polymers having the compositions described above melt to form liquid crystalline melt phases.
  • the polymers described above generally have melting temperatures as measured by differential scanning calorimetry in the range of about 275 °C to about
  • compositions generally melt in the range of about 300°C to about
  • liquid crystalline poly(esteramides) can be made by any of the methods already used in the art for making aromatic polyesters and poly(esteramides). These methods include: interfacial polymerization; the reaction of preformed phenyl esters of the aromatic acid groups with the phenolic groups of other monomers to yield polyester linkages and by-product phenol; and melt acidolysis polymerization, which is the preferred method. All of these polymerization methods involve the condensation of • reactive derivatives of the monomers rather than the free monomers, since the aromatic phenols and acids do not polymerize well.
  • melt acidolysis polymerization the phenolic reactants are acetylated to yield aromatic acetate groups, and these are then heated in the melt with the aromatic acids to yield acetic acid and polyester linkages.
  • This method is described in numerous patents, including U. S. Patent No. 4,473,682.
  • the melt acidolysis method is most conveniently carried out by acetylating the phenolic groups in situ and then heating the acetylated monomers to a high enough temperature to induce polymerization.
  • the melt acidolysis method is also useful for aromatic amines, which are generally charged to the reaction as N-acetyl derivatives rather than being acetylated in situ.
  • the preferred aromatic amine, 4-aminophenol is generally charged to the polymerization reaction as N-acetyl-4- aminophenol (also referred to as 4-hydroxyacetanilide or acetaminophen).
  • N-acetyl-4- aminophenol also referred to as 4-hydroxyacetanilide or acetaminophen.
  • Examples of methods of synthesizing aromatic poly(esteramides) by this method can be found in numerous references, such as U. S. Patent Nos. 5,204,443, 4,330,457, 4,966,956, 4,355,132, 4,339,375, 4,351,917 and 4,351,918.
  • the phenolic groups are acetylated in situ by including an approximately stoichiometric amount of acetic anhydride relative to the phenolic groups.
  • acetic anhydride typically included in the "stoichiometric" reactions. It has surprisingly been found that the reaction is improved when a large excess of acetic anhydride is included in the reaction. Thus if an additional excess of about 20% acetic anhydride is included above the typical 2.5%> excess, so that a total of 23%) excess acetic anhydride is used, then the reaction rate increases and the polymeric product has a higher molecular weight, as shown by the increased inherent viscosity.
  • excess acetic anhydride is generally beneficial when the amount of excess acetic anhydride (above the 2.5%> excess that is normally used in "stoichiometric" reactions) is in the range of about 5% to about 50%, preferably in the range of about 10% to about 30%>, and most preferably is about 20% (i.e. about 23% above true stoichiometry).
  • the polymerization reaction is carried out until the polymer reaches a useful molecular weight, as indicated by the inherent viscosity measured at 25 °C of a 0.1 %> solution on a weight/volume basis in a mixture of equal volumes of pentafluorophenol and hexafluoroisopropanol.
  • the inherent viscosity of the polymer generally is at least about 2 dl/g, preferably is at least about 3 dl/g, and ideally is at least about 5 dl/g.
  • the polymers of this invention are useful in the manufacture of shaped articles, such as fibers, films (e.g. extruded sheets or films) and molded articles. They are particularly useful for making molded articles in which a high heat distortion temperature or high impact resistance is desired. These polymers have an unusually high heat distortion temperature (HDT) in comparison with the crystalline melting temperature (Tm). This is desirable because molded articles with a high HDT can be made from these polymers at lower temperatures than from other polymers that have the same HDT. Therefore, the deleterious effects that are associated with processing the polymer at a high temperature in the molten phase, such as decomposition of the polymer, fillers, or other additives, are less likely to occur.
  • HDT heat distortion temperature
  • Tm crystalline melting temperature
  • Tm-HDT melting temperature and HDT
  • the polymers of this invention are generally blended with fillers and other additives at levels up to about 70%> by weight in order to achieve optimum properties.
  • Fillers and additives that may be useful include one or more fillers or reinforcing agents selected from the following list, which is not a complete or exhaustive list: glass fiber, calcium silicate, silica, clays, talc, mica, polytetrafluoroethylene, graphite, alumina, sodium aluminum carbonate, barium ferrite, woUastonite, carbon fiber, polymeric fiber, aluminum silicate fiber, titanium fiber, rock wool fiber, steel fiber, tungsten fiber and woUastonite fiber.
  • Other kinds of additives that may be used in addition to reinforcing fillers and reinforcing fibers include oxidation stabilizers, heat stabilizers, light stabilizers, lubricants, mold release agents, dyes, pigments, and plasticizers.
  • the polymers may also be melt spun into fibers having high strength and high modulus. After heat treatment, the fibers have tensile strengths up to about 20-25 gpd and modulus values up to about 500 gpd.
  • the reactor was evacuated to approximately 1 to 2 mbar followed by breaking the vacuum with nitrogen.
  • the vacuum-nitrogen purging process was repeated twice and 1004.1 grams (9.74 moles, 2.5 mole %> excess, 99 mol %> purity) of acetic anhydride was introduced into the reactor through an addition funnel.
  • the reactor was then heated in stages using a MicRIcon® controller. The temperature at each stage was increased to the final temperature of that stage during the elapsed time. Steps 1, 12 and 13 are isothermal.
  • the program follows:
  • the acetic acid began distilling off when the reactor was at 150°C. About 99% of the theoretical amount (1165 ml) had evolved at the end of segment 13.
  • the nitrogen purge was then turned off and the reactor was evacuated to about 2 mbar.
  • the torque on the stirrer that was needed to maintain constant stirring speed started to rise.
  • the reaction was terminated when the voltage to the stirrer increased by 12 mvolts above the initial value. This time was usually about 60 minutes to 100 minutes.
  • the reactor was cooled and broken to obtain the polymer. The polymer was then cut and ground into 11 chips. The yield was 1180 grams (87%>).
  • the inherent viscosity (IN.) of each sample was measured at 25 °C as a 0.1%) solution (wt./volume) in equal parts by volume of pentafluorophenol and hexafluoroisopropanol.
  • the melting temperature (T m ), heat of melting ( ⁇ H m ), crystallization temperature on cooling from the molten state (T c ), and heat of crystallization ( ⁇ H C ) were measured by differential scanning calorimetry (DSC; 20°C/min heating rate).
  • the melt viscosity of the polymer was measured in a capillary viscometer at shear rates of 100 sec "1 and 1000 sec" 1 . These properties are reported in Table 2.
  • the molten polymer of Example 10(a) was extruded at about 340°C through a single hole spinneret (0.005 inch diameter and 0.007 inch length) at a rate of 0.15 g/min.
  • the extruded filament was drawn down at a speed of 700 meters/minute and quenched in air at ambient conditions (about 25 °C and 65%> relative humidity).
  • the tensile properties of the as-spun fiber were measured using ASTM test method D3822: tenacity, 6 gdp; elongation, 1.8%; modulus, 423 gpd.
  • the as-spun fiber was then heat treated to obtain improved fiber properties as follows.
  • Fiber in an unstressed state was heated from room temperature to 150°C over a period of 60 minutes.
  • the fiber was held at 150°C for 60 minutes, then heated to 230°C over 60 minutes, held at 230°C for 3 hours, heated to 270°C over 60 minutes, and held at 270°C for 16 hours.
  • the properties of the heat treated fibers were measured using ASTM test method D3822: tenacity, 16.3 gpd; elongation, 2.8%), modulus, 499 gpd.
  • Example 8(b) was spun at about 329 °C to yield a fiber (single filament) having an as-spun tenacity of 6.2 gpd; elongation, 1.6%; modulus, 440 gpd. After heat treatment, the fiber had tenacity, 22 gpd; elongation, 4.2%>; modulus, 463 gpd.
  • a polymer having the same composition as Example 9 and an IN. - of 3.8 dl/g was spun at 340 °C through a single hole spinneret to yield a fiber having as- spun tenacity, 7.9 gpd; elongation, 2%; modulus, 450 gpd. After heat treatment, the fiber had tenacity, 23 gpd; elongation, 4.1%>; modulus, 500 gpd.
  • Examples C-1 to C-10 are comparative examples Table2. PHYSICALPROPERTIES

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une nouvelle classe de poly(estéramides) cristallins liquides thermotropiques se composant principalement d'unités monomères obtenues à partir d'environ 5 à 80 % de moles d'acide 4-hydroxybenzoïque, d'environ 5 à 35 % de moles d'acide 2,6-naphthalènedicarboxylique, d'environ 3 à 20 % de moles d'acide téréphthalique, d'environ 2 à 30 % de moles de 1,4-hydroquinone, d'environ 2 à 30 % de moles de 4-aminophénol et éventuellement d'un maximum d'environ 10 % de moles de 4,4'-diphénol. Ces poly(estéramides) se caractérisent par des températures de distorsion thermique exceptionnellement élevées par rapport à leurs températures de fusion.
PCT/US1995/006364 1994-06-06 1995-05-22 Poly(esteramides) cristallins liquide thermotropiques WO1995033803A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP8500962A JPH10501277A (ja) 1994-06-06 1995-05-22 サーモトロピック液晶性ポリ(エステルアミド)
EP95919897A EP0764195A1 (fr) 1994-06-06 1995-05-22 Poly(esteramides) cristallins liquide thermotropiques

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US25409994A 1994-06-06 1994-06-06
US08/254,099 1994-06-06

Publications (1)

Publication Number Publication Date
WO1995033803A1 true WO1995033803A1 (fr) 1995-12-14

Family

ID=22962923

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/006364 WO1995033803A1 (fr) 1994-06-06 1995-05-22 Poly(esteramides) cristallins liquide thermotropiques

Country Status (3)

Country Link
EP (1) EP0764195A1 (fr)
JP (1) JPH10501277A (fr)
WO (1) WO1995033803A1 (fr)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997034964A1 (fr) * 1996-03-22 1997-09-25 Hoechst Celanese Corporation Procede ameliore pour fabriquer des polymeres a cristaux liquides thermotropiques contenant de l'hydroquinone
WO1998014501A1 (fr) * 1996-09-30 1998-04-09 Hoechst Celanese Corporation Procede permettant de preparer directement des polyesters aromatiques thermotropiques a partir d'esters dialcoyliques aromatiques
WO2002079755A2 (fr) * 2001-03-29 2002-10-10 Kent State University Detection et amplification de ligands
US7267957B2 (en) 1998-06-10 2007-09-11 Kent State University Detection and amplification of ligands
US7341675B2 (en) * 2005-04-19 2008-03-11 E.I. Du Pont De Nemours And Company Liquid crystalline polymer composition
US7811811B2 (en) 2003-03-20 2010-10-12 Northeastern Ohio Universities College Of Medicine Self-contained assay device for rapid detection of biohazardous agents
US7947492B2 (en) 2008-08-20 2011-05-24 Northeastern Ohio Universities College Of Medicine Device improving the detection of a ligand
WO2013074477A1 (fr) * 2011-11-15 2013-05-23 Ticona Llc Composition de polymère cristal liquide riche en naphténiques ayant une performance d'inflammabilité améliorée
WO2013074476A1 (fr) * 2011-11-15 2013-05-23 Ticona Llc Composition polymère cristal liquide à faible teneur en napthéniques
WO2013074469A1 (fr) * 2011-11-15 2013-05-23 Ticona Llc Module de caméra compact
WO2013074467A1 (fr) * 2011-11-15 2013-05-23 Ticona Llc Composition de polymère cristal liquide à faible teneur en napthéniques pour une utilisation dans des pièces moulées d'une faible tolérance dimensionnelle
WO2013074475A1 (fr) * 2011-11-15 2013-05-23 Ticona Llc Composition de polymère cristal liquide pour des composants électroniques à haute tension
WO2014074228A1 (fr) * 2012-11-09 2014-05-15 Ticona Llc Composition de polymère cristallin liquide pour des feuilles extrudées à l'état fondu
WO2014074227A1 (fr) * 2012-11-09 2014-05-15 Ticona Llc Composition de polymère cristallin liquide pour des films
US8852730B2 (en) 2011-08-29 2014-10-07 Ticona Llc Melt-extruded substrate for use in thermoformed articles
US8906258B2 (en) 2011-08-29 2014-12-09 Ticona Llc Heat-resistant liquid crystalline polymer composition having a low melting temperature
US9005475B2 (en) 2011-08-29 2015-04-14 Ticona Llc Aromatic amide compound
US9045685B2 (en) 2011-08-29 2015-06-02 Ticona Llc Cast molded parts formed from a liquid crystalline polymer
US9051514B2 (en) 2011-08-29 2015-06-09 Ticona Llc High flow liquid crystalline polymer composition
US9057016B2 (en) 2011-08-29 2015-06-16 Ticona Llc Melt polymerization of low melt viscosity liquid crystalline polymers
US9074133B2 (en) 2011-08-29 2015-07-07 Ticona Llc Thermotropic liquid crystalline polymer with improved low shear viscosity
US9096794B2 (en) 2011-08-29 2015-08-04 Ticona Llc High flow liquid crystalline polymer composition
US9353263B2 (en) 2011-11-15 2016-05-31 Ticona Llc Fine pitch electrical connector and a thermoplastic composition for use therein

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005116141A1 (fr) * 2004-05-26 2005-12-08 Polyplastics Co., Ltd. Composition de résine thermoplastique
JP4765320B2 (ja) * 2005-01-19 2011-09-07 住友化学株式会社 芳香族ポリエステルおよびその用途
JP2009280831A (ja) * 2009-08-31 2009-12-03 Sumitomo Chemical Co Ltd 液晶性ポリエステル溶液組成物

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4355132A (en) * 1981-04-07 1982-10-19 Celanese Corporation Anisotropic melt phase forming poly(ester-amide) derived from p-hydroxybenzoic acid, 2,6-naphthalenedicarboxylic acid, aromatic monomer capable of forming an amide linkage, and, optionally, hydroquinone and additional carbocyclic dicarboxylic acid
JPS61236826A (ja) * 1985-04-13 1986-10-22 Kuraray Co Ltd 全芳香族ポリエステルアミドの製法
EP0352845A1 (fr) * 1988-07-27 1990-01-31 Cables De Comunicaciones, S.A. Procédé pour la préparation de copolyesteramides aromatiques thermotropes ainsi que les copolyesteramides correspondants.
EP0356226A2 (fr) * 1988-08-24 1990-02-28 Mitsubishi Chemical Corporation Polyesters aromatiques; polyester-amides aromatiques et procédé pour leur préparation
EP0359038A2 (fr) * 1988-09-13 1990-03-21 Bayer Ag Polycondensats formant des cristaux liquides à stabilité thermique, leur procédé de préparation et leur utilisation pour fabriquer des articles en forme de feuilles, de fibres et de filaments
EP0513545A2 (fr) * 1991-04-19 1992-11-19 Hoechst Celanese Corporation Polyester-amide façonnable à l'état fondu pouvant former une masse fondue anisotrope

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4355132A (en) * 1981-04-07 1982-10-19 Celanese Corporation Anisotropic melt phase forming poly(ester-amide) derived from p-hydroxybenzoic acid, 2,6-naphthalenedicarboxylic acid, aromatic monomer capable of forming an amide linkage, and, optionally, hydroquinone and additional carbocyclic dicarboxylic acid
EP0063881A1 (fr) * 1981-04-07 1982-11-03 Celanese Corporation Poly(esteramide) dérivant d'acide p-hydroxybenzoique, d'acide 2,6 naphtalène-dicarboxylique et d'un monomère aromatique capable de former une liaison amide
JPS61236826A (ja) * 1985-04-13 1986-10-22 Kuraray Co Ltd 全芳香族ポリエステルアミドの製法
EP0352845A1 (fr) * 1988-07-27 1990-01-31 Cables De Comunicaciones, S.A. Procédé pour la préparation de copolyesteramides aromatiques thermotropes ainsi que les copolyesteramides correspondants.
US4966956A (en) * 1988-07-27 1990-10-30 Cables De Comunicaciones, S.A. Aromatic thermotropic copolyesteramide
EP0356226A2 (fr) * 1988-08-24 1990-02-28 Mitsubishi Chemical Corporation Polyesters aromatiques; polyester-amides aromatiques et procédé pour leur préparation
US5025082A (en) * 1988-08-24 1991-06-18 Mitsubishi Kasei Corporation Aromatic polyester, aromatic polyester-amide and processes for producing the same
EP0359038A2 (fr) * 1988-09-13 1990-03-21 Bayer Ag Polycondensats formant des cristaux liquides à stabilité thermique, leur procédé de préparation et leur utilisation pour fabriquer des articles en forme de feuilles, de fibres et de filaments
EP0513545A2 (fr) * 1991-04-19 1992-11-19 Hoechst Celanese Corporation Polyester-amide façonnable à l'état fondu pouvant former une masse fondue anisotrope
US5204443A (en) * 1991-04-19 1993-04-20 Hoechst Celanese Corp. Melt processable poly(ester-amide) capable of forming an anisotropic melt containing an aromatic moiety capable of forming an amide linkage

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 011, no. 085 (C - 410) 14 March 1987 (1987-03-14) *

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5798432A (en) * 1996-03-22 1998-08-25 Hoechst Celanese Corp. Method of making thermotropic liquid crystalline polymers containing hydroquinone
WO1997034964A1 (fr) * 1996-03-22 1997-09-25 Hoechst Celanese Corporation Procede ameliore pour fabriquer des polymeres a cristaux liquides thermotropiques contenant de l'hydroquinone
WO1998014501A1 (fr) * 1996-09-30 1998-04-09 Hoechst Celanese Corporation Procede permettant de preparer directement des polyesters aromatiques thermotropiques a partir d'esters dialcoyliques aromatiques
US7927827B2 (en) 1998-06-10 2011-04-19 Kent State University Detection and amplification of ligands
US7267957B2 (en) 1998-06-10 2007-09-11 Kent State University Detection and amplification of ligands
US7732219B2 (en) 1998-06-10 2010-06-08 Kent State University Detection and amplification of ligands
WO2002079755A2 (fr) * 2001-03-29 2002-10-10 Kent State University Detection et amplification de ligands
WO2002079755A3 (fr) * 2001-03-29 2004-05-06 Univ Kent State Ohio Detection et amplification de ligands
US7811811B2 (en) 2003-03-20 2010-10-12 Northeastern Ohio Universities College Of Medicine Self-contained assay device for rapid detection of biohazardous agents
US7341675B2 (en) * 2005-04-19 2008-03-11 E.I. Du Pont De Nemours And Company Liquid crystalline polymer composition
US7947492B2 (en) 2008-08-20 2011-05-24 Northeastern Ohio Universities College Of Medicine Device improving the detection of a ligand
US8852730B2 (en) 2011-08-29 2014-10-07 Ticona Llc Melt-extruded substrate for use in thermoformed articles
US9096794B2 (en) 2011-08-29 2015-08-04 Ticona Llc High flow liquid crystalline polymer composition
US9074133B2 (en) 2011-08-29 2015-07-07 Ticona Llc Thermotropic liquid crystalline polymer with improved low shear viscosity
US9057016B2 (en) 2011-08-29 2015-06-16 Ticona Llc Melt polymerization of low melt viscosity liquid crystalline polymers
US9051514B2 (en) 2011-08-29 2015-06-09 Ticona Llc High flow liquid crystalline polymer composition
US9045685B2 (en) 2011-08-29 2015-06-02 Ticona Llc Cast molded parts formed from a liquid crystalline polymer
US9005475B2 (en) 2011-08-29 2015-04-14 Ticona Llc Aromatic amide compound
US8906258B2 (en) 2011-08-29 2014-12-09 Ticona Llc Heat-resistant liquid crystalline polymer composition having a low melting temperature
US8932483B2 (en) 2011-11-15 2015-01-13 Ticona Llc Low naphthenic liquid crystalline polymer composition
WO2013074475A1 (fr) * 2011-11-15 2013-05-23 Ticona Llc Composition de polymère cristal liquide pour des composants électroniques à haute tension
US8906259B2 (en) 2011-11-15 2014-12-09 Ticona Llc Naphthenic-rich liquid crystalline polymer composition with improved flammability performance
CN103930465A (zh) * 2011-11-15 2014-07-16 提克纳有限责任公司 用于具有小尺寸公差的模塑部件的低环烷液晶聚合物组合物
US8926862B2 (en) 2011-11-15 2015-01-06 Ticona Llc Low naphthenic liquid crystalline polymer composition for use in molded parts with a small dimensional tolerance
US9353263B2 (en) 2011-11-15 2016-05-31 Ticona Llc Fine pitch electrical connector and a thermoplastic composition for use therein
TWI498351B (zh) * 2011-11-15 2015-09-01 Ticona Llc 低環烷之液晶聚合物組合物
WO2013074477A1 (fr) * 2011-11-15 2013-05-23 Ticona Llc Composition de polymère cristal liquide riche en naphténiques ayant une performance d'inflammabilité améliorée
WO2013074467A1 (fr) * 2011-11-15 2013-05-23 Ticona Llc Composition de polymère cristal liquide à faible teneur en napthéniques pour une utilisation dans des pièces moulées d'une faible tolérance dimensionnelle
TWI487726B (zh) * 2011-11-15 2015-06-11 Ticona Llc 用於具有小尺寸公差之模製部件之低環烷之液晶聚合物組合物
WO2013074469A1 (fr) * 2011-11-15 2013-05-23 Ticona Llc Module de caméra compact
WO2013074476A1 (fr) * 2011-11-15 2013-05-23 Ticona Llc Composition polymère cristal liquide à faible teneur en napthéniques
US8853344B2 (en) 2012-11-09 2014-10-07 Ticona Llc Liquid crystalline polymer composition for films
WO2014074228A1 (fr) * 2012-11-09 2014-05-15 Ticona Llc Composition de polymère cristallin liquide pour des feuilles extrudées à l'état fondu
WO2014074227A1 (fr) * 2012-11-09 2014-05-15 Ticona Llc Composition de polymère cristallin liquide pour des films

Also Published As

Publication number Publication date
JPH10501277A (ja) 1998-02-03
EP0764195A1 (fr) 1997-03-26

Similar Documents

Publication Publication Date Title
WO1995033803A1 (fr) Poly(esteramides) cristallins liquide thermotropiques
US5508374A (en) Melt processable poly(ester amide) capable of forming an anisotropic melt containing an aromatic moiety capable of forming an amide linkage
EP0242959B1 (fr) Copolyesters aromatiques formant des masses fondues optiquement anisotropes à base de t-butylhydroquinone
US5110896A (en) Thermotropic liquid crystalline polyester compositions
US5798432A (en) Method of making thermotropic liquid crystalline polymers containing hydroquinone
CA1301392C (fr) Composition de resine presentant des proprietes anisotropiques a lafusion
EP0071447A1 (fr) Polyester d'acide 6-hydroxy-2 naphtoique, d'acide 4-hydroxy-benzoique, d'acide 1,4-cyclohexanedicarbonylique et de diol aromatique, capable d'être traité en fusion pour former des objets ayant des propriétés de résistance au choc
US4837268A (en) Wholly aromatic polyester
JPS5962630A (ja) 比較的低濃度の6−オキシ−2−ナフトイル部分を含む異方性溶融加工可能なポリエステル
US6222000B1 (en) Process for producing amorphous anisotropic melt-forming polymers having a high degree of stretchability
US5731401A (en) Process for the preparation of thermotropic aromatic polyesters directly from dialkyl aromatic esters
US4746566A (en) Optically anisotropic melt forming aromatic copolyesters based on t-butyl-4-hydroxybenzoic acid
US5216091A (en) High strength polymers and blends of hydroquinone poly(iso-terephthalates) containing residues of p-hydroxybenzoic acid
US5071942A (en) Melt processable thermotropic aromatic copolyesters
US5393848A (en) Process for forming improved liquid crystalline polymer blends
EP0736054B1 (fr) Poly(esteramide)s thermotropes contenant des unites monomeres derivees de l'acide 4,4'-biphenyldicarboxylique
JP2570708B2 (ja) 流動性の良好な耐熱性芳香族ポリエステル
WO1994004612A1 (fr) Melanges de polymeres isotropes et thermotropes mis en ×uvre par fusion
WO1991010707A1 (fr) Procede pour former un poly[co(4-oxybenzoate/paraphenylene-isophtalate)] et produit resultant
WO1993004127A1 (fr) Procede de production de melanges polymeres cristallins liquides ameliores
JPH0579095B2 (fr)
JPS63251426A (ja) 全芳香族サ−モトロピツク液晶ポリエステル

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1995919897

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1995919897

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1995919897

Country of ref document: EP