EP2209833A2 - Verfahren zur herstellung von polyarylethern - Google Patents

Verfahren zur herstellung von polyarylethern

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Publication number
EP2209833A2
EP2209833A2 EP08849095A EP08849095A EP2209833A2 EP 2209833 A2 EP2209833 A2 EP 2209833A2 EP 08849095 A EP08849095 A EP 08849095A EP 08849095 A EP08849095 A EP 08849095A EP 2209833 A2 EP2209833 A2 EP 2209833A2
Authority
EP
European Patent Office
Prior art keywords
independently
prepared
polyaryl ethers
groups
polyaryl
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP08849095A
Other languages
German (de)
English (en)
French (fr)
Inventor
Martin Weber
Volker Warzelhan
Faissal-Ali El-Toufaili
Andreas Greiner
Heiner Stange
Seema Agrarwal
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP08849095A priority Critical patent/EP2209833A2/de
Publication of EP2209833A2 publication Critical patent/EP2209833A2/de
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • 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
    • C08G65/4093—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 characterised by the process or apparatus used
    • 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/20—Polysulfones
    • 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
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/20—Polysulfones
    • C08G75/23—Polyethersulfones

Definitions

  • the present invention relates to a process for the preparation of polyaryl ethers and molding compositions based on polyaryl ethers.
  • the polyaryl ethers prepared using radiation in the microwave range in particular polysulfones (PES), polyether sulfones (PES) and polyphenylsulfones (PPSU), have improved mechanical and optical properties in molding compositions.
  • the thermoplastic molding compositions have an improved inherent color.
  • the present invention relates to the use of such molding compositions for the production of moldings, films, membranes and foams.
  • Polyaryl ethers belong to the group of high-performance thermoplastics and are distinguished by high heat resistance, good mechanical properties and inherent flame retardancy (see EM Koch, H. M. Walter, Kunststoffe 80 (1990) 1146, E. Döring, Kunststoffe 80 (1990) ) 1149). Because of their good biocompatibility, polyaryl ethers are also used as material for the preparation of medical materials, such as dialysis membranes (S. Savariar et al., Desalination 144 (2002) 15).
  • the polyaryl ethers are usually prepared by thermal polycondensation of suitable monomer units in dipolar aprotic solvents at elevated temperature (see RN Johnson et al., J. Polym., Vol al., Polymer 25 (1984) 1827).
  • EP-A 127 852 discloses a polyaryl ether comprising a mixture of polyarylene ether sulfones with the following recurring units (III):
  • EP-A 663 426 also discloses polymer blends based on a copolyaryl ether, consisting of 91 to 97 mol% of structural units (I) and 3 to 9% by weight of structural units (II) having a disperse phase consisting of one a further copolyaryl ether which has 91 to 97 mol% of structural units (II) and 3 to 9 mol% of structural units (I).
  • These blends are characterized by improved flowability, reduced bleed tendency and improved chemical resistance.
  • polyaryl ethers are produced under the action of heat energy containing naphthalene and terphenylene structures.
  • naphthalenediphenol salts are reacted with a phenyl ether dibromide in a condensation reaction.
  • EP-A 1 13 1 12 describes thermoplastic polymers which are obtained from three different monomer building blocks by thermal condensation reaction. For this purpose, a polymerization at temperatures of 120 ° to 180 ° under a set equimolar amounts of the corresponding hydroxy compounds and the halogen compounds in the presence of an alkali metal carbonate.
  • EP-A 297 363 describes high-temperature-resistant molding compositions which are composed of polyarylethersulfone building blocks and polyarylether units and can be obtained by thermal polycondensation using potassium carbonate and having a temperature of 190 °.
  • EP-A 135 130 describes a process for the preparation of linear polyarylene polyethers in which alkali metal double salts of dihydric phenols are reacted in equimolar amounts with a dihalobenzene compound. The reaction is carried out in N-methylpyrrolidone with heating and it is added anhydrous potassium carbonate.
  • the condensation at high temperature ie usually above 160 0 C (and usually above 140 0 C) must be carried out for several hours. Therefore, the polyaryl ethers obtained have a yellowish inherent color, which can be characterized, for example, on the basis of the so-called yellowness index.
  • the object of the present invention is to provide an improved process for the preparation of polyarylethers.
  • the process should be cost-effective and lead to products with improved color properties.
  • microwaves summarizes the decibel, centimeter and millimeter waves.
  • Microwaves are electromagnetic waves whose wavelength is between 1 m and 1 mm, which corresponds to a frequency range of about 300 MHz to about 300 GHz.
  • Microwaves are used, for example, in radar technology, in the microwave oven as well as in many technical applications such as plasma systems, wireless communication systems or sensor systems.
  • microwaves are particularly suitable for exciting dipole and multipole oscillations of molecules. They can therefore accelerate chemical reactions. This effect is particularly clear in the case of the vibration excitation of water molecules in the microwave oven.
  • the heating of water is not based on a specific resonant frequency, but the water molecules as dipoles constantly try to align themselves with the electromagnetic alternating field, whereby heat is generated as a dielectric loss.
  • microwaves of different frequency and power can be produced by runtime tubes (klystrons or magnetrons).
  • magnetrons are commonly used to produce microwaves in the range of up to 500W.
  • microwave reactors can also be used for the preparation of polymers (see S. Mallakpour et al., Journal of Applied Polymer Science, 2005, 96, 435, SA Scrinivasan et al., Journal of Applied Polymer Science 1997, 64, 179), however, problems also arise with the use of microwaves for the polymerization. For example, polymerization may be incomplete or lead to unfavorable molecular weight distribution.
  • the invention thus relates to a process for the preparation of polyaryl ethers, characterized in that, starting from the monomer building blocks, a polycondensation is carried out using microwave irradiation.
  • the resulting products also have a significantly improved intrinsic color.
  • the products of the same viscosity number produced by microwave-assisted reaction have improved processing stability and reduced oligomer content.
  • the molding compositions which can be prepared by the novel process comprise the polyaryl ether or ethers (component A) in a proportion of from 5 to 100, in particular from 5 to 99.8, usually from 5 to 98, preferably from about 20 to 96,% by weight.
  • Polyaryl ethers (component A) which can be prepared according to the invention are preferably composed of recurring units of the general formula (I)
  • x is 0.5 or 1
  • t and q independently of one another are 0, 1, 2 or 3
  • R a and R b independently of one another each represent a hydrogen atom or a C 1 -C 2 -alkyl group
  • R c and R d are each independently a hydrogen atom or a d-Ci2 alkyl, Ci-Ci2 alkoxy or C 6 -C 8 - are aryl group wherein R c and R d optionally substituted independently with fluorine and / or chlorine atoms are substituted or optionally together with the
  • Ar 1 is C 6 -C 8 arylene groups are independently of one another, which is optionally substituted with CrCl 2 -AIkIy-, C 6 -C 8 -aryl, CrCl 2 - alkoxy groups or halogen atoms are substituted.
  • x is 0.5 or 1
  • t and q are independently 0, 1, 2 or 3
  • Q, T and Z are each independently a chemical bond or a
  • Ar 1 is C 6 -C 2 are independently arylene groups, which is optionally substituted with CrCl 2 -AIkIy-, C 6 -C 2 aryl, CrCl 2 - alkoxy groups or halogen atoms are substituted.
  • polyaryl ether A based thereon by thermal reaction is described, for example, in GB-A 1 152 035 and US Pat. No. 4,870,153.
  • the classical thermal process conditions for the synthesis of polyaryl ethers are described, for example, in EP-A 0 113 112 and EP-A 0 135 130.
  • the reaction of the monomers in aprotic polar solvents in the presence of anhydrous alkali carbonate is described.
  • a preferred combination is N-methylpyrrolidone as solvent and potassium carbonate as catalyst.
  • the reaction in the melt is also known.
  • Suitable polyaryl ethers A are those having at least one of the following recurring structural units I 1 to I 29 :
  • Particularly preferred units of the formula (I) are units of the formulas (I 1 ), (I 2 ) and (I 8 ) which may be present individually or in a mixture.
  • polyaryl ethers which can be prepared according to the invention and consist of recurring units having at least one of the structures I 1 , I 2 and I 8 .
  • the polyaryl ethers A can also be copolymers or block copolymers in which polyarylene ether segments and segments of other thermoplastic polymers, such as polyamides, polyesters, aromatic polycarbonates, polyester carbonates, polysiloxanes, polyimides or polyetherimides are present.
  • polyarylene ether segments and segments of other thermoplastic polymers such as polyamides, polyesters, aromatic polycarbonates, polyester carbonates, polysiloxanes, polyimides or polyetherimides are present.
  • the molecular weights (number average) of the block or the graft arms in the copolymers are generally in the range from 1,000 to 30,000 g / mol.
  • the blocks of different structure may be arranged alternately or statistically.
  • the overall winhtc ⁇ ntoii n e r polyaryl ethers in the copolymers or block copolymers is undertaken at least 10% by weight.
  • the proportion by weight of the polyaryl ethers can be up to 99.8, in particular 97 wt .-%.
  • Particular preference is given to copolymers or block copolymers containing from 20 to 80% by weight of polyaryl ether.
  • the polyarylether have average molecular weights M n (number average) in the range of 5,000 to 60,000g / mol and relative viscosities of 0.20 to 0.95 dl / g.
  • M n number average
  • relative viscosities are measured either in 1% strength by weight N-methylpyrrolidone solution, in mixtures of phenol and dichlorobenzene or in 96% strength sulfuric acid at 20 ° C. or 25 ° C.
  • thermoplastic molding compositions according to the invention contain 0 to 50, preferably 0 to 45 and in particular 0 to 40 wt .-% of additives, such as fillers and reinforcing agents or impact-modifying rubbers.
  • the molding compositions of the polyarylethers prepared according to the invention may also contain other components, in particular auxiliaries, such as, for example, processing aids, pigments, stabilizers or mixtures of various additives.
  • auxiliaries such as, for example, processing aids, pigments, stabilizers or mixtures of various additives.
  • fibrous or particulate fillers or reinforcing materials or mixtures thereof may be included.
  • the quantities are in each case based on the total mass of the components.
  • Preferred fibrous fillers or reinforcing materials are carbon fibers, potassium tantanate whiskers, aramid fibers and particularly preferably glass fibers.
  • glass fibers can be provided with a size, preferably a polyurethane size, and a primer for better compatibility with the matrix material.
  • the carbon and glass fibers used have a diameter in the range of 6 to 20 microns.
  • the incorporation of the glass fibers can take place both in the form of short glass fibers and in the form of endless strands (rovings).
  • the average length of the glass fibers is preferably in the range of 0.08 to 0.5 mm.
  • Carbon or glass fibers can also be used in the form of woven fabrics, mats or glass silk rovings.
  • Suitable particulate fillers are amorphous silicic acid, carbonates, such as magnesium carbonate (chalk), powdered quartz, mica, various silicates, such as clays, muscovite, biotite, suzoite, tin malite, talc, chlorite, phlogophite, feldspar, calcium carbonate.
  • silicates such as wollastonite or aluminum silicates, such as kaolin, especially calcined kaolin.
  • particulate fillers are used, of which at least 95% by weight, preferably at least 98% by weight, of the particles have a diameter (largest dimension) determined on the finished product of less than 45 ⁇ m, preferably less than 40 ⁇ m, and whose so-called aspect ratio is in the range from 1 to 25, preferably in the range from 2 to 20, determined on the finished product.
  • the particle diameter can be determined, for example, by taking electron micrographs of thin sections of the polymer mixture and using at least 25, preferably at least 50 filler particles for the evaluation.
  • the particle diameters can also be determined by sedimentation analysis, for example according to "Transactions of ASAE", page 491 (1983) .
  • the proportion by weight of the fillers which is less than 40 ⁇ m can also be measured by sieve analysis from particle diameter to thickness (largest dimension to smallest dimension).
  • Particularly preferred particulate fillers are talc, kaolin, such as calcined kaolin or wollastonite or mixtures of two or all of these fillers.
  • talc with a proportion of at least 95 wt .-% of particles having a diameter of less than 40 microns and an aspect ratio of 1, 5 to 25, each determined on the finished product, particularly preferred.
  • Kaolin preferably has a content of at least 95% by weight of particles with a diameter of less than 20 ⁇ m and an aspect ratio of 1.2 to 20, in each case determined on the finished product.
  • the molding compositions according to the invention may also contain, as further component E, auxiliaries or additives, such as processing aids, pigments, stabilizers, flame retardants or mixtures of different additives.
  • auxiliaries or additives such as processing aids, pigments, stabilizers, flame retardants or mixtures of different additives.
  • Conventional additives are, for example, also oxidation inhibitors, agents against heat decomposition and decomposition by ultraviolet light, lubricants and mold release agents, dyes and plasticizers.
  • Their proportion is according to the invention from 0 to 30, preferably 0.2 to 30, preferably from 0 to 20 wt .-%, in particular 0 to 15 wt .-%, based on the total weight of the components.
  • the proportion of these stabilizers is usually up to 2% by weight. %, preferably 0.01 to 1 wt .-%, in particular 0.01 to 0.5 wt .-%, based on the total weight of A to E.
  • Pigments and dyes are generally present in amounts of up to 6, preferably 0.05 to 5 and in particular 0.1 to 3 wt .-%, based on the sum of all components.
  • the pigments for coloring thermoplastics are generally known, see, for example, R. Gumbleter and H. Müller, Taschenbuch der Kunststoffadditive, Carl Hanser Verlag, 1983, pages 494 to 510.
  • As the first preferred group of pigments are white pigments, such as zinc oxide , Zinc sulfide, lead white [2 PbCOs-Pb (OH) 2 ], lithlone, antimony white and titanium dioxide.
  • white pigments such as zinc oxide , Zinc sulfide, lead white [2 PbCOs-Pb (OH) 2 ], lithlone, antimony white and titanium dioxide.
  • rutile and anatase-type of titanium dioxide, in particular the rutile form is used for the whitening of the molding compositions according to the invention.
  • Black color pigments which can be used in the present invention are iron oxide black (Fe 3 O 4 ), spinel black [Cu (Cr, Fe) 2 O 4 ], manganese black (mixture of manganese dioxide, silica and iron oxide), cobalt black and antimony black, and particularly preferable Carbon black, which is usually used in the form of furnace or gas black [see G. Benzing, pigments for paints, Expert-Verlag (1988), pages 78 ff.].
  • inorganic colored pigments such as chromium oxide green or organic colored pigments, such as azo pigments or phthalocyanines, can be used according to the invention.
  • organic colored pigments such as azo pigments or phthalocyanines.
  • Such pigments are generally commercially available.
  • Oxidation inhibitors and heat stabilizers which can be added to the thermoplastic compositions according to the invention are, for example, halides of Group I metals of the periodic table, for example sodium, potassium, lithium halides, for example chlorides, bromides or iodides. Furthermore, zinc fluoride and zinc chloride can be used.
  • sterically hindered phenols hydroquinones, substituted members of this group, secondary aromatic amines, optionally in combination with phosphorus-containing acids or their salts, and mixtures of these compounds, preferably in concentrations up to 1 wt .-%, by weight of the entire composition.
  • UV stabilizers are various substituted resorcinols, salicylates, benzotriazoles and benophenones, which are generally used in amounts of up to 2 wt .-%.
  • Lubricants and mold release agents which are generally added in amounts of up to 1% by weight of the thermoplastic composition, are stearyl alcohol, stearic acid alkyl esters and amides, and also esters of pentaerythritol with long-chain fatty acids. It is also possible to use dialkyl ketones, for example distearyl ketone.
  • nucleating agents such as talc
  • a further embodiment of the invention relates to a process, characterized in that the reaction mixture containing the monomer units in the polycondensation reaction by irradiation of microwaves with frequencies in the range of 0.1 to 100 GHz to a temperature of 120 0 C to 280 0 C, preferably to a temperature of 120 0 C to 250 0 C, is brought.
  • One embodiment of the invention relates to a process in which a solvent and optionally a component collecting the resulting water are used in the polycondensation.
  • a further embodiment of the invention relates to a process, wherein in the polycondensation at least two different monomer units are used, wherein at least one dihalo-diarylsulphone and at least one dihydroxy-diarylsulphone and / or bisphenol A are used.
  • thermoplastic molding composition comprising, based on the total weight of the molding composition, the following components:
  • thermoplastic molding composition comprising, based on the total weight of the molding composition, the following components: a) 20 to 96 wt .-% of at least one polyaryl ether, prepared according to a method according to any one of claims 1 to 9,
  • the invention further relates to the use of thermoplastic molding compositions described above for the production of fibers, films and moldings. It also relates to the fibers, films, molded articles produced using a molding composition as described above.
  • Another embodiment of the invention relates to a shaped body, in particular selected from household articles, electronic components, laboratory equipment, medical devices or parts thereof.
  • the molding compositions according to the invention can be prepared by processes known per se, for example by means of extrusion.
  • the molding compositions can be prepared, for example, by mixing the starting components A, and optionally D and E in conventional mixing devices, such as screw extruders, preferably twin-screw extruders, Brabender mills or Banbury mills and kneaders and then extruded.
  • screw extruders preferably twin-screw extruders, Brabender mills or Banbury mills and kneaders
  • the extrudate is cooled and comminuted after extrusion.
  • the molding compositions according to the invention can preferably also be prepared by precipitating the components from a solution containing the components A in a solvent (L) (such as N-methylpyrollidone) and then extracting them if necessary, and then adding the components if appropriate D and E mixed in conventional mixing devices and then extruded.
  • a solvent such as N-methylpyrollidone
  • the order of mixing of the components can be varied, so two or possibly three components can be premixed, but it can also be mixed all components together.
  • Components A can also be premixed in the solution.
  • the addition of components D and E optionally takes place via the state of the melt.
  • intensive mixing is advantageous. For this purpose, average mixing times of 0.2 to 30 minutes, in particular 1 to 20 minutes at temperatures of 280 ° to 420 °, preferably 290 ° to 380 0 C, are generally required.
  • the molding compositions according to the invention are characterized by good mechanical properties, good flowability, improved toughness, especially elongation at break and notched impact strength and by an improved intrinsic color.
  • the molding compositions according to the invention are therefore suitable for the production of moldings for household articles, electrical or electronic components and moldings for the vehicle sector.
  • the viscosity number of the polyarylethersulfones is determined in 1% solution of N-methylpyrrolidone at 25 0 C.
  • the heat resistance of the samples is determined according to ISO 306 (Vicat B) (load 50 N, temperature increase of 50 K per hour, on ISO rods).
  • the notched impact strength of the products is determined in accordance with ISO 179 1 eB.
  • the elongation at break of the materials is determined according to ISO 527.
  • the flowability of the products is determined by measurement in a capillary rheometer at 370 0 C.
  • the melt stability of the products is determined by measuring the melt viscosity in a plate-plate rheometer at 400 ° C. The change in the viscosity determined at 55 Hz over a period of 5 or 60 minutes is considered.
  • the surface quality is determined visually on plates and classified according to the school grading system between 1 (very good) and 6 (insufficient).
  • the intrinsic color of the products was determined on the basis of the yellowness index (YI) according to the standard DIN 6167.
  • the reaction time, the residence time at 190 0 C is considered.
  • the water of reaction is distilled off and the level is kept constant by adding NMP during the reaction.
  • the reaction is stopped by dilution with cold NMP, then methyl chloride (10 l / h) is introduced into the batch at 140 ° C. for 45 minutes (45 minutes). Thereafter, nitrogen is introduced (20 l / h) and cooled the approach. The resulting potassium chloride is filtered off and the polymer solution is precipitated in water. The product is then extracted with 80 0 C hot water for 24 h, then dried at 120 0 C in a vacuum. The resulting powder is then granulated on a twin-screw extruder. The polymer viscosity is evaluated by the viscosity number (VZ / ml / g).
  • Example 2.2 of anhydrous potash with 20 ml of NMP, 11, 483 g DCDPS, 9.857 g DHDPS and 5,804 g (potassium carbonate) and in a single mode microwave oven with Powemax ® - Technology introduced.
  • microwaves 70 W
  • the reaction mixture was brought to 190 0 C.
  • the reaction was stopped.
  • the polymers obtained were isolated by precipitation in water, extraction of the resulting powder with hot water and subsequent drying.
  • Example 2.1 Corresponding experiments were carried out as Example 2.1 for the preparation of polysulfone.
  • the starting materials used were: 20 ml of NMP, 1 l, 483 g of DCDPS, 8.991 g of bisphenol A and 5.804 g of anhydrous potash.

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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)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polyesters Or Polycarbonates (AREA)
EP08849095A 2007-11-13 2008-11-11 Verfahren zur herstellung von polyarylethern Withdrawn EP2209833A2 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08849095A EP2209833A2 (de) 2007-11-13 2008-11-11 Verfahren zur herstellung von polyarylethern

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07120546 2007-11-13
PCT/EP2008/065273 WO2009062923A2 (de) 2007-11-13 2008-11-11 Verfahren zur herstellung von polyarylethern
EP08849095A EP2209833A2 (de) 2007-11-13 2008-11-11 Verfahren zur herstellung von polyarylethern

Publications (1)

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EP2209833A2 true EP2209833A2 (de) 2010-07-28

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US (1) US8378054B2 (enrdf_load_stackoverflow)
EP (1) EP2209833A2 (enrdf_load_stackoverflow)
JP (1) JP5490011B2 (enrdf_load_stackoverflow)
KR (1) KR20100100863A (enrdf_load_stackoverflow)
CN (1) CN101855271B (enrdf_load_stackoverflow)
IN (1) IN2010CN02651A (enrdf_load_stackoverflow)
MY (1) MY150563A (enrdf_load_stackoverflow)
WO (1) WO2009062923A2 (enrdf_load_stackoverflow)

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JP5490011B2 (ja) 2014-05-14
CN101855271B (zh) 2013-11-06
KR20100100863A (ko) 2010-09-15
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