EP1421072A1 - Polycarbonates de polyester obtenus a partir de diphenols particuliers - Google Patents

Polycarbonates de polyester obtenus a partir de diphenols particuliers

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Publication number
EP1421072A1
EP1421072A1 EP02762440A EP02762440A EP1421072A1 EP 1421072 A1 EP1421072 A1 EP 1421072A1 EP 02762440 A EP02762440 A EP 02762440A EP 02762440 A EP02762440 A EP 02762440A EP 1421072 A1 EP1421072 A1 EP 1421072A1
Authority
EP
European Patent Office
Prior art keywords
diphenols
formula
polycarbonates
preparation
mol
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Withdrawn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
EP02762440A
Other languages
German (de)
English (en)
Inventor
Rolf Wehrmann
Helmut-Werner Heuer
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.)
Covestro Deutschland AG
Original Assignee
Bayer MaterialScience AG
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 Bayer MaterialScience AG filed Critical Bayer MaterialScience AG
Publication of EP1421072A1 publication Critical patent/EP1421072A1/fr
Withdrawn legal-status Critical Current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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/30—General preparatory processes using carbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • 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
    • C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups

Definitions

  • the present invention relates to new polyester polycarbonates from special diphenols, processes for their preparation, their use for the production of moldings and extrudates, the moldings and extrudates obtainable therefrom, in particular substrates for optical data carriers containing them, and special diphenols themselves and their preparation and use for the preparation of polycarbonates.
  • low birefringence and low water absorption are not the only important properties for the substrate materials of optical data media, the optimal combination of other properties such as high transparency, heat resistance, flowability, toughness, high purity, low density, low inhomogeneities or particle proportions is required, as well especially low raw material and manufacturing costs.
  • Carboxylic acids, diphenols and carbonate precursors are described, for example, in EP-A 433 716, US-A 4 983 706 and US-A 5 274 068, which describe various processes for their synthesis.
  • the skilled worker is aware that the installation of Dicarboxylic acids lead to a lowering of the glass temperature and to an increase in fluidity.
  • the reduction in the glass temperature means that the usability of the discs is restricted, since this reduces their climate resistance.
  • these products have one for use in optical
  • polyester polycarbonates in particular those made from linear and longer-chain dicarboxylic acids, have an undesirable tendency to crystallize, which has a particularly disruptive effect on very slow cooling, which can be necessary for molding extremely fine structures and reducing process-related birefringence.
  • Dimer fatty acids as possible acid building blocks in polyester polycarbonates are listed, for example, in DE-A 43 06 961, US-A 5 134 220 and EP-A 443 058. There is no precise definition of the acids to be used. However, thermo-oxidative problems occur with non-hydrogenated dimer fatty acids. In addition, the common commercial products contain more than 3 mol% of three- and polybasic carboxylic acids, which leads to a high zero viscosity, which is undesirable when molding microstructures such as pits or grooves. For this reason, these polyester polycarbonates have so far generally not been considered suitable for substrates for optical data storage media.
  • the products described in the prior art are polymers which have too high a glass temperature for use as a substrate material for optical data storage media.
  • the invention is therefore based on the object of providing polyester polycarbonates which do not have the disadvantages mentioned above, but in particular have improved optical properties and are easy to produce.
  • polyester carbonates which are produced by one of the customary production processes for polycarbonates, characterized in that, in addition to the customary carbonic acid derivatives, dicarboxylic acids of the formula (I)
  • T is a branched or linear, saturated or unsaturated alkyl, arylalkyl or cycloalkyl part of 8-40 carbons, preferably saturated, linear
  • Rj to R 7 independently of one another, each for hydrogen, halogen, ad to C ⁇ -alkyl radical, preferably Ci to C 3 alkyl radical, particularly preferably methyl, a C 6 to Ci 9 aryl, preferably phenyl radical, a C 7 to C 1 2 - Aralkyl, preferably phenyl-C 1 to C 4 -alkyl, particularly preferably hydrogen, halogen, preferably chlorine or bromine, can be used for the preparation.
  • halogen ad to C ⁇ -alkyl radical
  • Ci to C 3 alkyl radical particularly preferably methyl
  • a C 6 to Ci 9 aryl preferably phenyl radical
  • a C 7 to C 1 2 - Aralkyl preferably phenyl-C 1 to C 4 -alkyl
  • halogen preferably chlorine or bromine
  • proportionately means that the special diphenols of the formulas Ha and Ui represent> 0% of the total amount of diphenols used.
  • the proportion of the diphenols of the formulas Ha and Ui is 100% of the diphenols used. In all other cases, the respective molar parts of the individual diphenols add up to 100%. In these mixtures of diphenols, the proportion of the diphenols is of the formulas Ua and
  • fatty acids particularly preferably hydrogenated dimeric fatty acids
  • dicarboxylic acids are particularly suitable as dicarboxylic acids.
  • dicarboxylic acids of the formula (I) or mixtures of such fatty acids are particularly suitable as dicarboxylic acids.
  • Sebacic acid dodecanedioic acid, hydrogenated dimer fatty acids, e.g. Pripol 1009 from Uniqema.
  • Uniqema's Pripol 1009 is a mixture of hydrogenated dimeric fatty acids which, according to Uniqema, is composed approximately as follows:
  • Dodecanedioic acid and Pripol 1009 are particularly preferred.
  • the invention also includes mixtures of dimeric fatty acids with other difunctional carboxylic acids with 4 to 40 carbon atoms such as adipic acid, sebacic acid, ⁇ , ⁇ -dodecanedicarboxylic acid, terephthalic acid, ice or trans-9-octadecen- ⁇ , ⁇ -dicarboxylic acid or hydroxycarboxylic acids with 4 to 40 carbon atoms such as salicylic acid or p-hydroxybenzoic acid.
  • dimeric fatty acids with other difunctional carboxylic acids with 4 to 40 carbon atoms such as adipic acid, sebacic acid, ⁇ , ⁇ -dodecanedicarboxylic acid, terephthalic acid, ice or trans-9-octadecen- ⁇ , ⁇ -dicarboxylic acid or hydroxycarboxylic acids with 4 to 40 carbon atoms such as salicylic acid or p-hydroxybenzoic acid.
  • the dimer fatty alcohols obtained from dimer fatty acids by reduction or mixtures of esters of dimer fatty alcohols with dimer fatty acids can also be used and converted to polyester polycarbonates.
  • Particularly preferred diphenols of the formulas (Ua) and (Ü) are:
  • Diphenol (in) which is obtained from resorcinol and acetone, is very particularly preferred.
  • the compounds of the formulas Ha, Hb and HI can be used both individually and in mixtures with one another.
  • polyester polycarbonates according to the invention are to be illustrated by way of example and preferred, but not by way of limitation, by the following structural description of the polyester carbonates:
  • Ei, E 2 , E 3 and E in formula Ic and Id each represent one of the substituents - (CH 2 ) j-, - (CH 2 ) j -, - (CH 2 ) CH 3 and - (CH 2 ) ⁇ CH and a, b, c, d, e, f, g, h, i, j, k, 1, m, n, o and p independently of one another represent an integer between 1 and 10,
  • radical -O-R-O- stands for diphenolate radicals derived from the above-mentioned diphenols of the formulas (Ua) and (Hb) or conventional diphenols, such as bisphenol A or bisphenol TMC.
  • Polycarbonate production usable diphenols meant, see. e.g. US-A 3 028 635, 2 999 835, 3 148 172, 2 991 273, 3 271 367, 4 982 014 and 2 999 846, DE-A 1 570 703, 2 063 050, 2 036 052, 2 211 956 and 3,832,396, French Patent 1,561,518, the monograph "H. Schnell, Chemistry and Physics of Polycarbonates, Interscience Publishers, New York 1964", p. 77 ff. And JP-A
  • 2,2-bis (4-hydroxyphenyl) propane bisphenol A
  • 1,1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane bisphenol TMC
  • 1,3-bis [2- (4-hydroxyphenyl) -2-propyl] benzene 1,1-bis (4-hydroxyphenyl) -1-phenylethane
  • 1,3-bis (4-hydroxyphenyl) cyclohexane bisphenol Z
  • 2,2-bis (4-hydroxyphenyl) propane bisphenol A
  • l, l-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane bisphenol TMC
  • very particularly preferably 2.2 -Bis called (4-hydroxyphenyl) propane bisphenol A
  • bifunctional monophenols such as resorcinol, hydroquinone or their derivatives substituted one or more times by C 1 to C 2 alkyl, C 6 to C 1 -aryl or C to cig-aralkyl can also be used for the preparation of the polyester polycarbonates according to the invention.
  • the substrates made from the polyester polycarbonates according to the invention are distinguished by a surprisingly particularly low water absorption, surprisingly low birefringence, very low tendency to crystallize, low refractive index, good flowability and low density and a low glass transition temperature
  • the substrates for data carriers made of the new polyester polycarbonates also have high transparency, good mechanical properties, especially at low temperatures, and high flowability.
  • Hydrogenated dimeric fatty acids in connection with this invention are to be understood as acids which can be obtained by dimerization of unsaturated monobasic fatty acids with 16 to 22 carbon atoms and subsequent hydrogenation.
  • the required acids can be obtained, for example, from plant or animal sources. Synthesis and properties are eg th ed Encyclopedia of Chemical Technology, Vol 8, 4, John Wiley & Sons.. 1993, pages 223-237 set.
  • These hydrogenated dimer fatty acids can still contain small amounts of unsaturated aliphatic groups. Dimer fatty acids with an iodine number of less than about 15 are preferred.
  • the diphenols of formula (Ha) and (Hb) can be prepared according to the reaction sequences shown in Schemes 1 and 2.
  • the diphenols prepared according to Scheme 1 are obtained after condensation of ketones (eg acetone, methyl ethyl ketone etc., from Aldrich) and optionally substituted resorcinol derivatives (eg 4-hexylresorcinol from Aldrich) with elimination of water under acidic conditions.
  • ketones eg acetone, methyl ethyl ketone etc., from Aldrich
  • resorcinol derivatives eg 4-hexylresorcinol from Aldrich
  • the condensation can also originate from phoron (2,6-dimethyl-2,5-heptadien-4-one) (from Aldrich) or substituted phorons.
  • Inorganic acids such as sulfuric acid are suitable as acids.
  • Acidic cation exchangers such as Lewatite ® are also possible.
  • JP-A 10265476 corresponding condensation methods for the production of spiro building blocks by reaction of resorcinol with ketones.
  • the condensations are usually carried out in common solvents such as hydrocarbons, toluene, NMP or chlorobenzene at temperatures between 20 and 200 ° C, preferably 30-180 ° C, particularly preferably 50-150 ° C and very particularly preferably 60-130 ° C ,
  • Preferred polyester polycarbonates according to the invention are those which have 0.5 to 49 mol%, preferably 2 to 40 mol%, particularly preferably 5 to 20 mol%, based on 100 mol% of the bifunctional structural units A and B, structural units A.
  • Preferred, particularly preferred or very particularly preferred are compounds or embodiments which fall under the definitions mentioned as preferred, particularly preferred or very particularly preferred or which make use of the definitions or explanations and parameters listed in preferred ranges.
  • the polyester polycarbonates according to the invention are distinguished in particular by a glass transition temperature of 120 to 195 ° C., preferably 125-180 ° C., particularly preferably 130 to 170 ° C. and very particularly preferably 135 to 165 ° C.
  • polyester polycarbonates according to the invention are notable for a low water absorption of ⁇ 0.40%, preferably ⁇ 0.38%, particularly preferably ⁇ 0.36%, very particularly preferably ⁇ 0.35% when saturated.
  • Moisture storage in 94% relative humidity at 30 ° C is understood.
  • the water content is then determined using quantitative Karl Fischer titration.
  • the substrates according to the invention can be produced by the known three methods (cf. H. Schnell "Chemistry and Physics of Polycarbonates",
  • the diphenols and bifunctional acids to be used are dissolved in an aqueous alkaline phase.
  • the chain terminators required for the preparation of the polyester polycarbonates according to the invention are dissolved in an aqueous alkaline phase, preferably sodium hydroxide solution, in an amount of 1.0 to 20 mol%, based on mol diphenol plus acid to be used according to the invention, or to this and an inert solution organic phase, added in bulk.
  • an inert, preferably polycarbonate-dissolving, organic phase is reacted with phosgene.
  • the reaction temperature is between
  • Alkali or inert organic solvents Alkali or inert organic solvents.
  • the reaction can be accelerated by catalysts such as tertiary amines or onium salts.
  • catalysts such as tertiary amines or onium salts.
  • Tributylamine, triethylamine and N-ethylpiperidine and tetrabutylammonium, tetrathylammonium and N-ethylpiperidinium salts are preferred.
  • their chlorocarbonic acid esters and / or bischlorocarbonic acid esters can also be used or added during the synthesis.
  • dimer fatty acids their acid chlorides can also be used.
  • Suitable solvents are, for example, methylene chloride, chlorobenzene, toluene and mixtures thereof.
  • the diphenols and acids according to the invention are dissolved in organic bases such as pyridine, optionally with the addition of further organic solvents, then, as described under 1.
  • organic bases such as pyridine
  • chain terminators and branching agents required for the preparation of the polyester polycarbonates according to the invention are optionally added.
  • phosgene The reaction temperature is between 10 and 50 ° C.
  • Suitable organic bases besides pyridine are e.g. Triethylamine, tri-butylamine, N-ethylpiperidine and N, N-dialkyl-substituted anilines, such as N, N-dimethylaniline.
  • Suitable solvents are, for example, methylene chloride, chlorobenzene, toluene, tetrahydrofuran, 1,3-dioxolane and mixtures thereof.
  • fatty acids according to the invention can be replaced by their acid chlorides.
  • the necessary chain terminators, branching agents and acids according to the invention can also be added during the phosgenation or as long as chlorocarbonic acid esters are present in the synthesis mixture, in bulk, as a melt or as a solution in inert organic solvents.
  • Processes 1 and 2 isolate the polyester polycarbonates according to the invention in a known manner. Suitable processing procedures are particularly in particular the precipitation, the spray drying and the evaporation of the solvent in vacuo.
  • Phosphonium salts for the purposes of the invention are those of the formula (V)
  • R 1 '4 the same or different C ⁇ -C ⁇ 0 alkyls, C ö -Cio-aryl, C -C ⁇ o-
  • Aralkyls or C 5 -C 6 cycloalkyls can be, preferably methyl or C 6 -C 4 aryls, particularly preferably methyl or phenyl, and X "is an anion such as hydroxide, sulfate, hydrogen sulfate, hydrogen carbonate, carbonate, a halide, preferably chloride , or an alcoholate of the formula OR, where RC 6 -C 14 aryl or C 7 -C 12 aralkyl, preferably phenyl, can be.
  • Preferred catalysts are Tetraphenylphosphonium chloride, tetraphenylphosphonium hydroxide, tetraphenylphosphoniumphenolate, particularly preferably tetraphenylphosphoniumphenolate.
  • acids to be used according to the invention their aromatic or aliphatic esters, e.g. Methyl, ethyl, isopropyl or phenyl esters can be used.
  • chain terminators and / or branching agents can also be used for the production of the polyester polycarbonates according to the invention.
  • the corresponding chain terminators and / or branching devices are, inter alia, from EP-A 335 214 (pages 3-5) and DE-A 30 07 934 (pages 8-9) and EP-A 411 433 (pages 4 and 5) and EP-A 691 361 (page 5) is known.
  • the branching agents and / or chain terminators can be replaced in whole or in part by dimer fatty acids with a higher content of tri- and / or monofunctional carboxylic acids.
  • the substrates made from the polyester polycarbonates according to the invention can be mixed with various thermoplastic polymers in a weight ratio of 2:98 to 98: 2 and used as blends.
  • polyester polycarbonates according to the invention have average molecular weights M w (weight average, determined by gel chromatography (column combination from Merck consisting of PS4000, PS400 and PS40) after prior calibration
  • the polyester polycarbonates for the production of the data carriers according to the invention can contain the additives customary for thermoplastic polycarbonates, such as stabilizers, for example thermal stabilizers, organic phosphites, optionally in combination with monomeric or oligomeric epoxides; UV stabilizers, especially those based on nitrogenous ones
  • Heterocycles such as triazoles; optical brighteners, flame retardants, in particular fluorine-containing, such as perfluorinated salts of organic acids, polyperfluoroethylene, salts of organic sulfonic acids and combinations thereof; mold release agents; Flow aids; Fire retardants; Colorant; pigments; antistatic agents; Fillers and reinforcing materials, divided minerals, fibrous materials, e.g. Alkyl and aryl phosphites, phosphates,
  • the data carriers according to the invention or other molded bodies can be produced in a known manner by injection molding or injection molding on known machines.
  • the invention also relates to extrudates and moldings containing them, such as optical lenses, plates and foils which contain the polyesters polycarbonates according to the invention, and the use of these polyesters polycarbonates to produce such moldings and extrudates.
  • extrudates and moldings containing them such as optical lenses, plates and foils which contain the polyesters polycarbonates according to the invention, and the use of these polyesters polycarbonates to produce such moldings and extrudates.
  • the excellent properties of these polyesters are particularly useful for optical lenses and data storage devices.
  • polyester carbonate according to the invention examples are, but are not limited to, the following: 1. Safety windows, which are known to be required in many areas of buildings, vehicles and aircraft, and as shields for helmets.
  • blow bodies for example 1 to 5 gallon water bottles.
  • optical device parts in particular lenses for photo and film cameras (see for example DE-OS 2 701 173).
  • a light transmission carrier in particular as an optical fiber cable (see for example EP-AI 0 089 801).
  • Headlight lamps For the manufacture of lights, e.g. Headlight lamps, as so-called “head lamps”, scattered light panes or inner lenses. 19.
  • Oxygenators For medical applications, e.g. Oxygenators, dialyzers.
  • Polyesters polycarbonates according to the invention containing structural units A and B, the structural unit B of which are derived from the compounds of the formulas Ha and Hb, but in particular from formula HI, and 0.5 to 49 mol%, preferably 2 to 40 mol%, particularly preferably 10 to 25 mol %, based on 100 mol% of the bifunctional structural units A and B, containing bifunctional ester structural units A are, owing to their low rheo-optical constant C R , particularly suitable for the production of the data carriers according to the invention.
  • the substrates must have a high degree of purity. This is achieved by reducing the residual monomer, solvent, foreign particle (inorganic or organic type, in particular salts and dust) and the chlorine content to the lowest possible values in a known manner when working up and isolating the substrate resin.
  • the data carriers according to the invention can be designed in various forms. Known forms such as optical cards or cylindrical perforated disks such as compact disks (CD), CD recordables (CD-R), CD rewritable (CD-RW), digital versatile disks (DVD) or mini disks (MD) are particularly preferred.
  • CD compact disks
  • CD-R CD recordables
  • CD-RW CD rewritable
  • DVD digital versatile disks
  • MD mini disks
  • Information storage layers e.g. phase change
  • Layers magneto-optical layers, dyes, fluorescent dyes, photopolymers), dielectric (e.g. Si / N), reflective (e.g. silver, gold or aluminum), semi-reflective (e.g. Si, Ge), protective layers (e.g. acrylic paints) and other functional layers. Different sequences of such layers are possible.
  • the stored information can be embossed in the substrate (e.g. as a pit structure) or stored in separate information layers.
  • the information can be read out through the transparent substrate or from the information side.
  • Optical information storage media in which the substrate material according to the invention in the form of foils, for example to cover the information layer in DVR (Direct Video Recording) or as a substrate of multilayer systems (if appropriate with embossed information) are also part of the invention.
  • DVR Direct Video Recording
  • multilayer systems if appropriate with embossed information
  • iodine number ⁇ 10, monomer content ⁇ 0.1%, trimer content ⁇ 1%.
  • 0.42 g of phosgene is passed into a mixture of 1.22 g of Pripol 1009, 0.169 g, NaOH, 87.6 g of water and 175.1 ml of methylene chloride at room temperature. Allow to stir briefly. A mixture of 10.21 g of diphenol from Example 1, 0.09 g of tert-butylphenol, 2.64 g of NaOH, 87.6 g of water and 0.04 ml of N-ethylpiperidine is then added from a storage vessel. For condensation, 5.93 g of phosgene are introduced, the pH being kept in the range from 12.5 to 12.8 by occasional addition of sodium hydroxide solution.
  • the mixture is acidified with dilute phosphoric acid and then washed with distilled water until free of electrolytes.
  • the organic phase is separated off and concentrated on a rotary evaporator.
  • the product is precipitated by introduction into methanol, isolated by filtration and dried in a water jet vacuum.
  • a polyester polycarbonate was produced from the diphenol from Example 1 and Pripol 1009 with 13% by weight Pripol 1009. To isolate the polymer, the organic phase was evaporated to dryness (no precipitation).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention concerne de nouveaux polycarbonates de polyester obtenus à partir de diphénols particuliers ; des procédés pour leur production ; leur utilisation pour la production de corps moulés et d'articles extrudés ; les corps moulés et articles extrudés ainsi obtenus, notamment des substrats les contenant, destinés à des supports de données optiques ; les diphénols eux-mêmes ; leur production et leur utilisation pour la production de polycarbonates de polyester.
EP02762440A 2001-08-24 2002-08-12 Polycarbonates de polyester obtenus a partir de diphenols particuliers Withdrawn EP1421072A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10141621 2001-08-24
DE10141621A DE10141621A1 (de) 2001-08-24 2001-08-24 Polyesterpolycarbonate aus speziellen Diphenolen
PCT/EP2002/008997 WO2003020714A1 (fr) 2001-08-24 2002-08-12 Polycarbonates de polyester obtenus a partir de diphenols particuliers

Publications (1)

Publication Number Publication Date
EP1421072A1 true EP1421072A1 (fr) 2004-05-26

Family

ID=7696549

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EP02762440A Withdrawn EP1421072A1 (fr) 2001-08-24 2002-08-12 Polycarbonates de polyester obtenus a partir de diphenols particuliers

Country Status (8)

Country Link
US (1) US6696543B2 (fr)
EP (1) EP1421072A1 (fr)
JP (1) JP2005507956A (fr)
KR (1) KR20040044469A (fr)
CN (1) CN1294128C (fr)
DE (1) DE10141621A1 (fr)
TW (1) TW583183B (fr)
WO (1) WO2003020714A1 (fr)

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Publication number Priority date Publication date Assignee Title
DE10315290A1 (de) * 2003-04-04 2004-10-14 Bayer Materialscience Ag Hochverzweigte Polycarbonate und Copolycarbonate mit verbesserter Fließfähigkeit, ihre Herstellung und Verwendung
WO2005058995A1 (fr) * 2003-12-17 2005-06-30 Dsm Ip Assets B.V. Compositions aqueuses de revetement d'urethanne-vinyl antitaches
US7848025B2 (en) * 2008-12-31 2010-12-07 Sabic Innovative Plastics Ip B.V. Transparent articles prepared from thermoplastic compositions having high flow and ductility, and method of preparing articles
US8064140B2 (en) * 2008-12-31 2011-11-22 Sabic Innovative Plastics Ip B.V. Transparent articles prepared from thermoplastic compositions having low birefringence
CN113667110B (zh) * 2021-09-06 2023-01-13 万华化学集团股份有限公司 一种光学聚碳酸酯树脂及其制备方法

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JP2828699B2 (ja) 1989-11-21 1998-11-25 出光興産株式会社 高分子化合物及びそれよりなる光学成形品
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US4983706A (en) 1990-01-30 1991-01-08 General Electric Company Interfacial process comprising reacting a dihydric phenol, a carbonate precursor and an aliphatic alpha omega dicarboxylic salt
DE4010029A1 (de) 1990-03-29 1991-10-02 Bayer Ag Polyester und polyestercarbonate auf basis von 3,8-dihydroxy-5a,10b-diphenylcumarano -2',3',2,3-cumaran
US5274068A (en) 1992-04-23 1993-12-28 General Electric Company Catalytic, interfacial, pH controlled preparation of polyester polycarbonate
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JP3468873B2 (ja) 1994-10-19 2003-11-17 出光興産株式会社 電子写真感光体
JPH10251395A (ja) * 1997-03-11 1998-09-22 Mitsubishi Gas Chem Co Inc コポリカーボネート重合体およびそれを用いた電子写真感光体
JPH11227666A (ja) * 1998-02-13 1999-08-24 Bridgestone Cycle Co 自転車用補助動力装置
JP3740309B2 (ja) * 1999-02-04 2006-02-01 キヤノン株式会社 電子写真感光体、プロセスカートリッジ及び電子写真装置

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Also Published As

Publication number Publication date
JP2005507956A (ja) 2005-03-24
KR20040044469A (ko) 2004-05-28
DE10141621A1 (de) 2003-03-06
WO2003020714A1 (fr) 2003-03-13
US6696543B2 (en) 2004-02-24
CN1564819A (zh) 2005-01-12
CN1294128C (zh) 2007-01-10
US20030120024A1 (en) 2003-06-26
TW583183B (en) 2004-04-11

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