WO1988000605A1 - Melanges contenant des polyesters cristallins liquides - Google Patents

Melanges contenant des polyesters cristallins liquides Download PDF

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Publication number
WO1988000605A1
WO1988000605A1 PCT/US1987/001703 US8701703W WO8800605A1 WO 1988000605 A1 WO1988000605 A1 WO 1988000605A1 US 8701703 W US8701703 W US 8701703W WO 8800605 A1 WO8800605 A1 WO 8800605A1
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WO
WIPO (PCT)
Prior art keywords
poly
acid
liquid crystalline
aryl ether
carried out
Prior art date
Application number
PCT/US1987/001703
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English (en)
Inventor
Marcus Matzner
Donald Mark Papuga
Original Assignee
Amoco Corporation
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Filing date
Publication date
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Publication of WO1988000605A1 publication Critical patent/WO1988000605A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers

Definitions

  • PAE poly(aryl ethers)
  • PEEK is the acronym of poly(aryl ether ketone)
  • PEEK is the acronym of poly(ether ether ketone) in which the phenylene units in the structure are assumed.
  • poly(aryl ether ketone)s exhibit an excellent combination of properties; i.e., thermal and hydrolytic stability, high strength and toughness, wear and abrasion resistance and solvent resistance.
  • articles molded from poly(aryl ether ketones) have utility where high performance is required.
  • fabrication difficulties arise due to the high melt viscosity of the poly(aryl ether ketones).
  • Poly(aryl ethers) have been known for about two decades; they are tough linear polymers that possess a number of attractive features such as excellent high temperature resistance, good electrical properties, and very good hydrolytic stability. Two poly(aryl ethers) are commercially available. A poly(aryl ether sulfone) is available from Imperial Chemical Industries Limited. It has the formula (3) and is produced by the
  • liquid crystalline aromatic polyesters which may be used herein are well known from the art. These liquid crystalline polyesters are described in, for example, U.S. Patents 3,804,805; 3,637,595; 4,130,545; 4,161,470; 4,230,817 and 4,265,802.
  • the materials are characterized in that they exhibit optical anisotropy in the melt phase.
  • Liquid crystalline polyesters are ordered, high strength materials, having very good high temperature properties; they are characterized by a relatively low melt viscosity and are particularly suitable for high strength fibers and filaments. Due to their high crystallinity their solvent and chemical resistance are excellent. Their main drawback as molding materials resides in the anisotropy of properties displayed by molded parts. Liquid crystalline polyesters were reviewed several times, see, for example, W.J. Jackson, Jr. Journal of Applied Polymer Science, Applied Polymer Symposium 41, 25-33 (1985).
  • the present invention is directed to improved blends wherein one component is a poly(aryl ether ketone), a poly(aryl ether), or a poly(phenylene oxide), and wherein the second component is a liquid crystalline polyester. More particularly, the invention is directed to a new process whereby the subject blends are prepared. The process consists in preparing the liquid crystalline polyester in the presence of a preformed poly(aryl ether ketone), poly(aryl ether), or poly(phenylene oxide). The method leads to blends having a better and more intimate degree of mixing than those obtained by mixing the two preformed polymers. As a result, products with improved mechanical properties and good melt-fabricability are obtained. These properties are superior to those of the materials made as described for example in U.S. Pat. Nos. 4,460,736 and 4,438,236.
  • Ar is independently a divalent aromatic radical selected from phenylene, biphenylene, or
  • naphthalene is independently O, , SO 2 , or a direct bond and a is an integer of from 1 to 4, b, c, d and e are 0 to 1 and preferably d is 0 when b is 1.
  • the process for preparing the poly(aryl ether ketones) comprises reacting a mixture (substantially equimolar amounts when maximum molecular weight is sought) of at least one bisphenol and at least one dihalobenzenoid compound or a halophenol.
  • the bisphenols may be depicted as follows:
  • the dihalobenzenoid compound may be depicted as follows:
  • Y is halogen, preferably fluorine, chlorine, or nitro; the Y's may be the same or different and are ortho or para to the X or X'; Ar, X, and X' are as defined above with the proviso that X or X' ortho or para to the Y's are electron withdrawing groups,
  • each aromatic radical is para substituted and most preferably, 1,4-phenylene.
  • the halophenols may be depicted as follows:
  • withdrawing group i.e., or SO 2 .
  • Preferred dihalobenzenoid and halophenol compounds include:
  • the reaction is carried out by heating a mixture of one or more bisphenols and one or more dihalobenzenoid compounds or halophenols at a temperature of from about 100 to about 400°C.
  • the reactions are conducted in the presence of an alkali metal carbonate or bicarbonate.
  • an alkali metal carbonate or bicarbonate Preferably a mixture of alkali metal carbonates or bicarbonates is used.
  • the mixture comprises sodium carbonate or bicarbonate with a second alkali metal carbonate or bicarbonate wherein the alkali metal of the second carbonate or bicarbonate has a higher atomic number than that of sodium.
  • the amount of the second alkali metal carbonate or bicarbonate is such that there is from 0.01 to about 0.25 gram atoms of the second alkali metal per gram atom of sodium.
  • the higher alkali metal carbonates or bicarbonates are thus selected from the group consisting of potassium, rubidium and cesium carbonates and bicarbonates. Preferred combinations are sodium carbonate or bicarbonate with potassium carbonate or cesium carbonate.
  • the alkali metal carbonates or bicarbonates should be anhydrous although, if hydrated salts are employed, where the polymerization temperature is relatively low, e.g. 100 to 250°C, the water should be removed, e.g. by heating under reduced pressure, prior to reaching the polymerization temperature.
  • an entraining organic medium can be used to remove water from the reaction such as toluene, xylene, chlorobenzene, and the like.
  • the total amount of alkali metal carbonate or bicarbonate employed should be such that there is at least 1 atom of alkali metal for each phenol group.
  • a diphenol there should be at least 1 mole of carbonate, or 2 moles of bicarbonate, per mole of the aromatic diol.
  • a halophenol is employed there should be at least 0.5 mole of carbonate, or 1 mole of bicarbonate, per mole of the halophenol.
  • An excess of carbonate or bicarbonate may be employed. Hence there may be 1 to 1.2 atoms of alkali metal per phenol group. While the use of an excess of carbonate or bicarbonate may give rise to faster reactions, there is the attendant risk of cleavage of the resulting polymer, particularly when using high temperatures and/or the more active carbonates.
  • the amount of the second (higher) alkali metal carbonate or bicarbonate employed is such that there are 0.001 to about 0.2 grams atoms of the alkali metal of higher atomic number per gram atom of sodium.
  • a mixed carbonate for example sodium and potassium carbonate, may be employed as the second alkali metal carbonate.
  • one of the alkali metal atoms of the mixed carbonate is sodium
  • the amount of sodium in the mixed carbonate should be added to that in the sodium carbonate when determining the amount of mixed carbonate to be employed.
  • the alkali metal of the second alkali metal carbonate or bicarbonate per gram atom of sodium is used.
  • a bisphenol and a dihalobenzenoid compound are employed, they should be used in substantially equimolar amounts. An excess of one over the other leads to the production of lower molecular weight products. However a slight excess, up to 5 mole %, of the dihalide or of the diphenol may be employed if desired.
  • the reaction is carried out in the presence of an inert solvent or partially in the absence of a solvent.
  • the solvent is an aliphatic or aromatic sulphoxide or sulphone of the following formula
  • R and R' are alkyl or aryl groups and may be the same or different.
  • R and R' may together form a divalent radical.
  • Preferred solvents include dimethyl sulphoxide, dimethyl sulphone, sulpholane (1,1 dioxothiolan), or aromatic sulphones of the formula: where R 2 is a direct link, an oxygen atom or two hydrogen atoms (one attached to each benzene ring) and R 3 and R' 3 , which may be the same or different, are hydrogen atoms and alkyl or phenyl groups.
  • aromatic sulphones examples include diphenylsulphone, dibenzothiophen dioxide, phenoxathiin dioxide and 4-phenylsulphonyl biphenyl.
  • Diphenylsulphone is the preferred solvent.
  • Other solvents that may be used include benzophenone, N,N-dimethyl acetamide, N,N-dimethyl formamide and N-methyl-2-pyrrolidone.
  • the polymerization temperature is in the range of from about 100° to about 400°C and will depend on the nature of the reactants and the solvent, if any, employed.
  • the preferred temperature is above 270°C.
  • the reactions are generally performed under atmospheric pressure. However, higher or lower pressures may be used.
  • the maximum polymerization temperature be below 350°C.
  • the polymerization reaction may be terminated by mixing a suitable end capping reagent, e.g. a mono or polyfunctional halide such as methyl chloride, difluorobenzophenone, monofluoro benzophenone, 4,4'-dichlorodiphenylsulphone with the reaction mixture at the polymerization temperature, heating for a period of up to one hour at the polymerization temperature and then discontinuing the polymerization.
  • a suitable end capping reagent e.g. a mono or polyfunctional halide such as methyl chloride, difluorobenzophenone, monofluoro benzophenone, 4,4'-dichlorodiphenylsulphone
  • This invention is also directed to an improved process for making the poly(aryl ether ketones). Specifically, this process is directed to preparing the poly(aryl ether ketone) polymer by the reaction of a mixture of at least one bisphenol and at least one dihalobenzenoid compound and/or by the reaction of a halophenol. The reactions are carried out by heating the above reactants at a temperature of from about 100 to about 400°C. The reaction is conducted in the presence of added sodium carbonate and/or bicarbonate, and potassium, rubidium or cesium fluorides or chlorides. The sodium carbonate or bicarbonate and the chloride and fluoride salts should be anhydrous although, if hydrated salts are employed, where the reaction temperature is relatively low, e.g. 100 to 250°C, the water should be removed, e.g. by heating under reduced pressure, prior to reaching the reaction temperature.
  • an entraining organic medium can be used to remove water from the reaction such as toluene, xylene, chlorobenzene, and the like.
  • the total amount of sodium carbonate and/or bicarbonate and potassium, rubidium or cesium fluoride or chloride employed should be such that there is at least 1 atom of total alkali metal for each phenol group, regardless of the anion (carbonate, bicarbonate or halide).
  • a halophenol is employed there should be at least one mole of total alkali metal per mole of halophenol.
  • alkali metal derived from alkali metal halide
  • the sodium carbonate and/or bicarbonate and potassium fluoride are used such that the ratio of potassium to sodium therein is from about 0.001 to about 0.5, preferably from about 0.01 to about 0.25, and most preferably from about 0.02 to about 0.20.
  • An excess of total alkali metal may be employed. Hence there may be about 1 to about 1.7 atoms of alkali metal per phenol group. While the use of a large excess of alkali metal may give rise to faster reactions, there is the attendant risk of cleavage of the resulting polymer, particularly when using high temperatures and/or the more active alkali metal salts.
  • cesium is a more active metal and potassium is a less active metal so that less cesium and more potassium are used.
  • the chloride salts are less active than the fluoride salts so that more chloride and less fluoride is used.
  • a bisphenol and dihalobenzenoid compound are employed, they should be used in substantially equimolar amounts when maximum molecular weight is sought. However an excess of bisphenol or dihalide may be employed if desired. An excess of one monomer over the other leads to the production of low molecular weight products which can be desirable when the process is directed to making lower molecular weight PAEK.
  • the reaction may be carried out in the presence of an inert solvent, or partially in the absence of a solvent.
  • a solvent is employed and is an aliphatic or aromatic sulphoxide or sulphone of the formula
  • R and R' are alkyl or aryl groups and may be the same or different. R and R' may together form a divalent radical.
  • Preferred solvents include dimethyl sulphoxide, dimethyl sulphone, sulpholane (1,1 dioxothiolan), or aromatic sulphones of the formula.
  • R 2 is a direct link, an oxygen atom or two hydrogen atoms (one attached to each benzene ring) and R 3 and R' 3 , which may be the same or different, are hydrogen atoms or phenyl groups.
  • poly(aryl ether), polymers suitable for the purposes of this invention are linear thermoplastic polyarylene polyethers containing recurring units of the formula:
  • liquid crystalline copolyesters Two commercially available liquid crystalline copolyesters are Ekonol, a homopolymer of p-hydroxybenzoic acid, and Ekkcel, a copolymer of p-hydroxybenzoic acid, terephthalic and isophthalic acids, and 4,4-'biphenol.
  • Other liquid crystalline polyarylates of interest include the copolyester of p-hydroxybenzoic acid and 6-hydroxy-2-naphthoic acid in a 75/25 molar ratio.
  • the groups Ar 5 and Ar 6 are divalent aromatic radicals which are residues of diphenols and diacids that are suitable components for the liquid crystalline polyester.
  • the method depicted above consists in first preparing an ester of the hydroxyl-containing reactants with a lower mono-carboxylic acid.
  • R 7 preferably a C 1 to C 4 alkyl or a phenyl group. These esters are then reacted under acidolysis conditions with the acid containing reactants to yield the polyester and the lower monocarboxylic acid which can be recycled.
  • the two steps, i.e., the preparation of the monocarboxylic acid esters of the phenolic reactants and their polymerization can be performed separately, or in a one-pot procedure.
  • phenyl esters of the carboxylic acids are used.
  • the ester-exchange reaction is generally carried out in the temperature range of about 200 to about 350°C. However, lower and higher temperatures can also be used.
  • the molecular weights of the block copolymers can be further advanced using solid state techniques, vide ultra.
  • the reaction can be performed at atmospheric, reduced, or higher than atmospheric pressures. Catalysts such as, for example, alkali metal phenoxides, may be used to accelerate the polymerization.
  • Typical solvents useful for this type of polymerization are, for example, the chlorinated aromatic hydrocarbons such as chlorobenzene, dichloro-, trichloro-, and tetrachlorobenzenes, chlorinated diphenyls or diphenyl ethers, chlorinated naphthalenes, as well as nonchlorinated aromatics such as terphenyl, benzophenone, dibenzylbenzenes, and the like.
  • the reaction can be run with or without catalysts.
  • Typical catalysts are metallic magnesium, as described in U.S. Pat. No. 3,733,306, tetravalent titanium esters, as described in German Patent Application 1,933,687, and the like.
  • the weight ratio of the blend components i.e., the ratio of the poly(aryl ether ketone) or of the poly(aryl ether), or of the poly(phenylene oxide) to the liquid crystalline polyester may be within the range of 90:10 to 10:90 by weight. It is preferably in the range of 20:80 to 80:20, and most preferably in the range of 25:75 to 75:25.
  • the blends of this invention may include mineral fillers such as carbonates including chalk, calcite and dolomite; silicates including mica, talc, wollastonite; silicon dioxide; glass spheres; glass powders; aluminum; clay; quartz; and the like. Also, reinforcing fibers such as fiberglass, carbon fibers, and the like may be used.
  • the blends may also include additives such as titanium dioxide; thermal stabilizers, ultraviolet light stabilizers, plasticizers, and the like.
  • the blends of this invention may be fabricated into any desired shape, i.e., moldings, coatings, films, or fibers. They are particularly desirable for molding, for fiber, and for use as electrical insulation for electrical conductors. Also, the blends may be woven into monofilament threads which are then formed into industrial fabrics by methods well known in the art as exemplified by U.S. Patent 4,359,501. Further, the blends may be used to mold gears, bearings and the like.
  • Poly(aryl ether) II A polymer having a repeat unit of the formula:
  • Poly(phenylene oxide) A polymer having the formula:

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyethers (AREA)

Abstract

Les mélanges améliorés décrits, dont un constituant est un poly(cétone d'aryléther), un poly(aryléther) ou un poly(oxyde de phénylène) et dont le second constituant est un polyester cristallin liquide, présentent des propriétés mécaniques améliorées, une bonne stabilité aux hautes températures et une bonne résistance aux solvants ainsi qu'une bonne aptitude au formage à l'état fondu.
PCT/US1987/001703 1986-07-21 1987-07-15 Melanges contenant des polyesters cristallins liquides WO1988000605A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US88718886A 1986-07-21 1986-07-21
US887,188 1986-07-21

Publications (1)

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WO1988000605A1 true WO1988000605A1 (fr) 1988-01-28

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PCT/US1987/001703 WO1988000605A1 (fr) 1986-07-21 1987-07-15 Melanges contenant des polyesters cristallins liquides

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EP (1) EP0275295A4 (fr)
JP (1) JPH01501066A (fr)
WO (1) WO1988000605A1 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0423311A1 (fr) * 1989-04-28 1991-04-24 Univ Akron Thermoplastique hautes performances renforce par une fibre polyester entierement aromatique et procede pour sa preparation.
EP0438128A2 (fr) * 1990-01-19 1991-07-24 Unitika Ltd. Composition de polymère À  mouler par fusion
WO1991010707A1 (fr) * 1990-01-16 1991-07-25 Hoechst Celanese Corporation Procede pour former un poly[co(4-oxybenzoate/paraphenylene-isophtalate)] et produit resultant
EP0522404A2 (fr) * 1991-07-06 1993-01-13 BASF Aktiengesellschaft Copolycondensats à blocs résistant aux hautes températures
US5182334A (en) * 1991-04-03 1993-01-26 Hoechst Celanese Corp. Compatible LCP blends via direct esterification
EP0542232A1 (fr) * 1991-11-11 1993-05-19 Sumitomo Chemical Company, Limited Composition de polyester liquide cristallin
US5321087A (en) * 1989-03-08 1994-06-14 Mitsui Toatsu Chemicals, Incorporated Preparation process of thermoplastic resin composite
US5393848A (en) * 1990-01-16 1995-02-28 Hoechst Celanese Corp. Process for forming improved liquid crystalline polymer blends
EP0722985A2 (fr) * 1995-01-20 1996-07-24 Sumitomo Chemical Company, Limited Compositions à base de polyéthercétones et support pour la transformation et traitement des plaquettes semi-conductrices
US5571875A (en) * 1989-11-30 1996-11-05 Mitsui Toatsu Chemicals, Inc. Polyimide based resin composition
US5677392A (en) * 1995-01-25 1997-10-14 Polyplastics Co. Ltd. Reinforced composite resin material and method for its production
US5698632A (en) * 1995-06-07 1997-12-16 General Electric Company Compatible compositions of poly(phenylene ether) resins and semi-crystalline resins
US5789492A (en) * 1990-01-16 1998-08-04 Hoechst Aktiengesellschaft Weathering-resistant polymer alloys
US6048948A (en) * 1994-09-07 2000-04-11 Mazda Motor Corporation Method for producing a polymer composite material
WO2000040655A1 (fr) * 1999-01-08 2000-07-13 E.I. Du Pont De Nemours And Company Compositions a base de melanges de polymeres cristallins liquides poly(phenylene oxydes) a indice de cheminement d'arc eleve
US6579954B1 (en) * 1998-02-20 2003-06-17 Sumitomo Chemical Company, Limited Aromatic polysulfone resin composition and molded article containing the same
WO2016028614A1 (fr) 2014-08-21 2016-02-25 Ticona Llc Composition contenant une polyaryléthercétone et un polymère cristallin liquide à faible teneur en napthène

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US4075173A (en) * 1976-01-29 1978-02-21 Sumitomo Chemical Company, Limited Process for the production of aromatic polyesters from hydroxybenzoic acid and products thereof
US4386174A (en) * 1979-11-30 1983-05-31 Imperial Chemical Industries Limited Compositions of melt-processable polymers having improved processability
US4386186A (en) * 1982-03-29 1983-05-31 Union Carbide Corporation Process for preparing polyarylates
US4414365A (en) * 1981-03-16 1983-11-08 Sumitomo Chemical Company, Limited Process for producing an aromatic polyester composition
EP0170067A2 (fr) * 1984-06-29 1986-02-05 Amoco Corporation Mélanges de polyaryléthercétones et de polyarylates

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
US4075173A (en) * 1976-01-29 1978-02-21 Sumitomo Chemical Company, Limited Process for the production of aromatic polyesters from hydroxybenzoic acid and products thereof
US4386174A (en) * 1979-11-30 1983-05-31 Imperial Chemical Industries Limited Compositions of melt-processable polymers having improved processability
US4414365A (en) * 1981-03-16 1983-11-08 Sumitomo Chemical Company, Limited Process for producing an aromatic polyester composition
US4386186A (en) * 1982-03-29 1983-05-31 Union Carbide Corporation Process for preparing polyarylates
EP0170067A2 (fr) * 1984-06-29 1986-02-05 Amoco Corporation Mélanges de polyaryléthercétones et de polyarylates

Non-Patent Citations (1)

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Title
See also references of EP0275295A4 *

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5478888A (en) * 1989-03-08 1995-12-26 Mitsui Toatsu Chemicals, Inc. Preparation process of thermoplastic resin composite
US5321087A (en) * 1989-03-08 1994-06-14 Mitsui Toatsu Chemicals, Incorporated Preparation process of thermoplastic resin composite
EP0423311A4 (en) * 1989-04-28 1991-11-21 The University Of Akron Wholly aromatic polyester fiber-reinforced high performance thermoplastic and process for preparing same
EP0423311A1 (fr) * 1989-04-28 1991-04-24 Univ Akron Thermoplastique hautes performances renforce par une fibre polyester entierement aromatique et procede pour sa preparation.
US5571875A (en) * 1989-11-30 1996-11-05 Mitsui Toatsu Chemicals, Inc. Polyimide based resin composition
US5393848A (en) * 1990-01-16 1995-02-28 Hoechst Celanese Corp. Process for forming improved liquid crystalline polymer blends
WO1991010707A1 (fr) * 1990-01-16 1991-07-25 Hoechst Celanese Corporation Procede pour former un poly[co(4-oxybenzoate/paraphenylene-isophtalate)] et produit resultant
US5789492A (en) * 1990-01-16 1998-08-04 Hoechst Aktiengesellschaft Weathering-resistant polymer alloys
EP0438128A2 (fr) * 1990-01-19 1991-07-24 Unitika Ltd. Composition de polymère À  mouler par fusion
EP0438128A3 (en) * 1990-01-19 1992-08-26 Unitika Ltd. Polymer blend composition for melt molding
US5182334A (en) * 1991-04-03 1993-01-26 Hoechst Celanese Corp. Compatible LCP blends via direct esterification
EP0522404A3 (en) * 1991-07-06 1993-03-17 Basf Aktiengesellschaft High temperature-resistant block copoly condensates
EP0522404A2 (fr) * 1991-07-06 1993-01-13 BASF Aktiengesellschaft Copolycondensats à blocs résistant aux hautes températures
US5278254A (en) * 1991-11-11 1994-01-11 Sumitomo Chemical Company, Limited Liquid crystalline polyester resin composition containing polyphenylene ether modified with amine
EP0542232A1 (fr) * 1991-11-11 1993-05-19 Sumitomo Chemical Company, Limited Composition de polyester liquide cristallin
US6048948A (en) * 1994-09-07 2000-04-11 Mazda Motor Corporation Method for producing a polymer composite material
EP0722985A3 (fr) * 1995-01-20 1997-11-12 Sumitomo Chemical Company Limited Compositions à base de polyéthercétones et support pour la transformation et traitement des plaquettes semi-conductrices
EP0722985A2 (fr) * 1995-01-20 1996-07-24 Sumitomo Chemical Company, Limited Compositions à base de polyéthercétones et support pour la transformation et traitement des plaquettes semi-conductrices
US5677392A (en) * 1995-01-25 1997-10-14 Polyplastics Co. Ltd. Reinforced composite resin material and method for its production
US5698632A (en) * 1995-06-07 1997-12-16 General Electric Company Compatible compositions of poly(phenylene ether) resins and semi-crystalline resins
US5719236A (en) * 1995-06-07 1998-02-17 General Electric Company Compatible compositions of poly(phenylene ether) resins and semi-crystalline resins
US5723551A (en) * 1995-06-07 1998-03-03 General Electric Company Compatible compositions of poly-phenylene ether) resins and semi-crystalline resins
US6579954B1 (en) * 1998-02-20 2003-06-17 Sumitomo Chemical Company, Limited Aromatic polysulfone resin composition and molded article containing the same
WO2000040655A1 (fr) * 1999-01-08 2000-07-13 E.I. Du Pont De Nemours And Company Compositions a base de melanges de polymeres cristallins liquides poly(phenylene oxydes) a indice de cheminement d'arc eleve
US6441074B1 (en) 1999-01-08 2002-08-27 E. I. Du Pont De Nemours And Company High ARC tracking-index poly(phenylene oxide)-liquid crystalline poly
WO2016028614A1 (fr) 2014-08-21 2016-02-25 Ticona Llc Composition contenant une polyaryléthercétone et un polymère cristallin liquide à faible teneur en napthène
CN106574184A (zh) * 2014-08-21 2017-04-19 提克纳有限责任公司 包含聚芳基醚酮和低环烷液晶聚合物的组合物
EP3183320A4 (fr) * 2014-08-21 2018-01-31 Ticona LLC Composition contenant une polyaryléthercétone et un polymère cristallin liquide à faible teneur en napthène
US10774215B2 (en) 2014-08-21 2020-09-15 Ticona Llc Composition containing a polyaryletherketone and low naphthenic liquid crystalline polymer

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EP0275295A4 (fr) 1990-02-21
JPH01501066A (ja) 1989-04-13
EP0275295A1 (fr) 1988-07-27

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