EP1240231A1 - Supports de donnees optiques et procede permettant de les produire - Google Patents

Supports de donnees optiques et procede permettant de les produire

Info

Publication number
EP1240231A1
EP1240231A1 EP00969530A EP00969530A EP1240231A1 EP 1240231 A1 EP1240231 A1 EP 1240231A1 EP 00969530 A EP00969530 A EP 00969530A EP 00969530 A EP00969530 A EP 00969530A EP 1240231 A1 EP1240231 A1 EP 1240231A1
Authority
EP
European Patent Office
Prior art keywords
polycarbonate
phase
separated
data carriers
optical data
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Withdrawn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
EP00969530A
Other languages
German (de)
English (en)
Inventor
Wilfried Haese
Friedrich-Karl Bruder
Thomas Bieringer
Steffen Kühling
Franky Bruynseels
Dirk Van Meirvenne
Réne DE CLEYN
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.)
Bayer Antwerpen NV
Covestro Deutschland AG
Original Assignee
Bayer Antwerpen NV
Bayer 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 Antwerpen NV, Bayer AG filed Critical Bayer Antwerpen NV
Publication of EP1240231A1 publication Critical patent/EP1240231A1/fr
Withdrawn legal-status Critical Current

Links

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
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
    • G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
    • 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
    • C08G64/22—General preparatory processes using carbonyl halides
    • C08G64/24—General preparatory processes using carbonyl halides and phenols
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/21—Circular sheet or circular blank

Definitions

  • the invention relates to optical data carriers with particular stability when irradiated with blue laser light and to a method for their production.
  • High-purity polycarbonate is required for optical data carriers, since the polycarbonate is located in the optical beam path of the laser and the information structures stored in the polycarbonate have orders of magnitude in the micrometer range or submicron range.
  • the development continues to refine the information structures even further and to use lasers of shorter wavelength, e.g. those that emit blue light, which has a higher energy compared to the laser wavelengths common today. It was therefore the task of developing data carriers or processes for their production which have particular stability when irradiated with blue laser light.
  • Polycarbonate is produced by the so-called phase interface process, in which dihydroxydiarylalkanes in the form of their alkali salts are reacted with phosgene in the heterogeneous phase in the presence of inorganic bases such as sodium hydroxide solution and an organic solvent in which the product polycarbonate is readily soluble.
  • phase interface process in which dihydroxydiarylalkanes in the form of their alkali salts are reacted with phosgene in the heterogeneous phase in the presence of inorganic bases such as sodium hydroxide solution and an organic solvent in which the product polycarbonate is readily soluble.
  • EP-A-264 885 proposes to stir the aqueous washing liquid with the polycarbonate solution and to separate the aqueous phase by centrifugation.
  • Japanese application JP-A-07 19 67 83 describes a process for the production of polycarbonate, in which a favorable color behavior is achieved the iron content in the sodium hydroxide solution used should be below 2 ppm.
  • the object of the present invention is to provide an alternative and improved method for producing pure polycarbonate substrates and to provide optical data carriers which have particular stability when irradiated with blue laser light.
  • the application therefore relates to a process for the preparation of polycarbonate by the interfacial process, dihydroxydiarylalkanes in the form of their alkali metal salts being reacted with phosgene in the heterogeneous phase in the presence of sodium hydroxide solution and an organic solvent, characterized in that
  • the starting materials are low in Fe, Cr, Ni, Zn, Ca, Mg, Al metals or their homologues
  • the organic solvent is separated off and c) the polycarbonate obtained is worked up.
  • poor in the metals mentioned or their chemical homologues means that preferably not more than 2 ppm, preferably not more than 1 ppm and particularly preferably not more than 0.5 ppm and very particularly preferably not more than 0.2 ppm Total metal, in particular the metals listed above and their homologues, is contained in the starting materials.
  • the alkali metals are excluded from these limit values.
  • the sodium hydroxide solution should preferably be low in the metals mentioned. In particular, based on a 100% by weight NaOH content, the sodium hydroxide solution should not contain more than 1 ppm, preferably not more than 0.5 ppm, preferably not more than 0.3 ppm, of alkaline earth metal or its homologues. In particular, the sodium hydroxide feed should be based on a 100% by weight
  • the sodium hydroxide solution is preferably used in the process according to the invention as a 20 to 55% by weight, particularly preferably 30-50% by weight solution.
  • Low in metal in particular low in Fe, Cr, Ni, Zn, Ca, Mg, Al.
  • Embodiments are also included, in which sodium hydroxide and
  • These low-metal feedstocks are obtained by distilling the solvent in a preferred variant, crystallizing the bisphenol, preferably repeatedly crystallizing or distilling, and using water of VE quality.
  • the deionized water is preferably desalinated, degassed and / or silicified.
  • the quality criterion is, for example, the electrical conductivity (sum parameter for ionogenic substances of the salts still present in traces in the water).
  • the demineralized water has an electrical conductivity of 0.2 ⁇ S / cm (DIN 38404 C 8) and a SiO 2 concentration of 0.02 mg / kg (VGB 3.3.1.1) or less.
  • At least the sodium hydroxide solution preferably also the bisphenol, particularly preferably the sodium hydroxide solution, the bisphenol and the water, very particularly preferably the sodium hydroxide solution, the bisphenol, the water and the organic solvent are selected from the group of starting materials at least once, preferably filtered twice, particularly preferably gradually three times before the start of the reaction.
  • Another object of the invention is a process for the production of polycarbonate by the phase interface process, dihydroxydiarylalkanes in the form of their alkali metal salts being reacted with phosgene in the heterogeneous phase in the presence of sodium hydroxide solution and an organic solvent, characterized in that
  • the starting materials are low in Fe, Cr, Ni, Zn, Ca, Mg, Al metals or their homologues, d) the aqueous phase formed in the reaction is separated off and the separated organic polycarbonate Phase is washed with an aqueous liquid and e) the washed and separated from the washing liquid organic polycarbonate phase, optionally after filtration, is heated and filtered at least once hot, b) the organic solvent is separated off and c) the polycarbonate obtained is worked up.
  • the reaction mixture is filtered in process step a) directly after the reaction and / or the organic polycarbonate phase obtained and separated is filtered and / or the organic polycarbonate phase separated in process step b) is filtered. At least two of these filtrations, in particular all three filtrations, are preferably carried out.
  • the mixture is filtered at least once, preferably twice, particularly preferably at least three times, in particular stepwise.
  • Step-by-step filtration starts with coarser filters and then changes to finer filters. It is preferred that the filtration of the two-phase media in process step a) is carried out using coarser filters.
  • filters with a small pore size are used for the hot filtration. It is important for this that the polycarbonate phase is as homogeneous as possible. This is achieved by heating the organic polycarbonate phase, which generally still contains residues of aqueous washing liquid. The washing liquid is dissolved and a clear solution is created. The previously dissolved impurities, especially the dissolved alkali salts, precipitate out and can be filtered off.
  • the known freezing-out method can also be used to achieve a homogeneous solution.
  • membrane filters and sintered metal filters or bag filters are used as filters.
  • the pore size of the filter is usually 0.01 to 5 ⁇ m, preferably 0.02 to 1.5 ⁇ m, preferably 0.05 ⁇ m to 1.0 ⁇ m.
  • filters are commercially available from companies, for example
  • the aqueous phase is emulsified in the organic phase during the reaction. This creates droplets of different sizes.
  • the organic phase containing the polycarbonate is usually washed several times with an aqueous liquid and, after each washing process, is removed from the aqueous one
  • the washing is preferably carried out with finely filtered, low-metal water.
  • the polymer solution is usually cloudy after washing and separating the washing liquid.
  • Aqueous liquid for separating the catalyst, a dilute mineral acid such as HC1 or H3PO4 and further purification of demineralized water are used as washing liquid.
  • the concentration of HC1 or H3PO4 in the washing liquid can be, for example, 0.5 to 1.0% by weight.
  • the organic phase is washed by way of example and preferably in a final manner.
  • phase separation devices for separating the washing liquid from the organic phase.
  • the solvent is evaporated to obtain the high-purity polycarbonate.
  • Evaporation can be done in several evaporator stages.
  • the solvent or part of the solvent can be removed by spray drying.
  • the high-purity polycarbonate is then obtained as a powder.
  • extrusion is a suitable means for evaporating residual solvents.
  • Another technology is the strand evaporator technology.
  • Compounds preferably to be used as starting materials are bisphenols of the general formula HO-Z-OH, in which Z is a divalent organic radical having 6 to 30 Is carbon atoms containing one or more aromatic groups.
  • Z is a divalent organic radical having 6 to 30 Is carbon atoms containing one or more aromatic groups.
  • Examples of such compounds are bisphenols which belong to the group of dihydroxydiphenyls, bis (hydroxyphenyl) alkanes, indane bisphenols, bis (hydroxyphenyl) ethers, bis (hydroxyphenyl) sulfones, bis (hydroxyphenyl) ketones and ⁇ , ⁇ '-bis (hydroxyphenyl) diisopropylbenzenes belong.
  • Particularly preferred bisphenols which belong to the abovementioned connecting groups are 2,2-bis- (4-hydroxyphenyl) propane (BPA), tetraalkylbisphenol-A, 4,4- (meta-phenylenediisopropyl) diphenol (bisphenol M), l, l-bis- (4-hydroxyphenyl) -3,3,5-trimethylcyclohexanone and optionally their mixtures.
  • Particularly preferred copolycarbonates are those based on the monomers bisphenol-A and l, l-bis- (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane.
  • the bisphenol compounds to be used according to the invention are reacted with carbonic acid compounds, in particular phosgene.
  • the polyester carbonates are obtained by reacting the bisphenols already mentioned, at least one aromatic dicarboxylic acid and optionally carbonic acid.
  • aromatic dicarboxylic acids are, for example, orthophthalic acid, terephthalic acid, isophthalic acid, 3,3'- or 4,4'-diphenyldicarboxylic acid and benzophenone dicarboxylic acids.
  • Inert organic solvents used in the process are, for example, dichloromethane, the various dichloroethanes and chloropropane compounds, chlorobenzene and chlorotoluene, dichloromethane and mixtures of dichloromethane and chlorobenzene are preferably used.
  • reaction can be carried out by catalysts such as tertiary amines, N-alkylpiperidines or
  • N-ethylpiperidine used.
  • a monofunctional phenol such as phenol, cumylphenol, p.-tert.-butylphenol or 4- (l, l, 3,3-tetramethylbutyl) phenol can be used.
  • isatin biscresol can be used as branching agent.
  • the bisphenols are dissolved in an aqueous alkaline phase, preferably sodium hydroxide solution.
  • the chain terminators which may be required for the production of copolycarbonates are dissolved in amounts of 1.0 to 20.0 mol% per mole of bisphenol, in the aqueous alkaline phase or added to them in bulk in an inert organic phase.
  • phosgene is introduced into the mixer containing the other reaction components and the polymerization is carried out.
  • Chain terminators which may be used are both monophenols and monocarboxylic acids.
  • Suitable monophenols are phenol itself, alkylphenols such as cresols, p-tert-butylphenol, p-cumylphenol, pn-octylphenol, p-iso-octylphenol, pn-nonylphenol and p-iso-nonylphenol, halophenols such as p-chlorophenol, 2,4 -
  • Suitable monocarboxylic acids are benzoic acid, alkylbenzoic acids and halogenated benzoic acids.
  • Preferred chain terminators are the phenols of the formula (I)
  • R is hydrogen, tert-butyl or a branched or unbranched Cg and / or C alkyl radical.
  • the preferred chain terminator is phenol and p-tert-butylphenol.
  • the amount of chain terminator to be used is 0.1 mol% to 7 mol%, based on moles of diphenols used in each case.
  • the chain terminators can be added before, during or after phosgenation.
  • branching agents can also be added to the reaction.
  • branching agents can also be added to the reaction.
  • Branchers are the tri- or more than trifunctional compounds known in polycarbonate chemistry, in particular those with three or more than three phenolic OH groups.
  • Branches are exemplary and preferably also phloroglucin, 4,6-dimethyl-2,4,6-tri- (4-hydroxyphenyl) -hepten-2, 4,6-dimethyl-2,4,6-tri- (4-hydroxyphenyl ) -heptan, 1, 3,5-tri- (4-hydroxyphenyl) -benzene, 1,1,1-tri- (4-hydroxyphenyl) -ethane, tri- (4-hydroxyphenyl) -phenylmethane, 2,2- Bis- [4,4-bis (4-hydroxyphenyl) cyclohexyl] propane, 2,4-bis (4-hydroxyphenylisopropyl) phenol, 2,6-bis (2-hydroxy-5'- methylbenzyl) -4-methylphenol, 2- (4-hydroxyphenyl) -2- (2,4-dihydroxyphenyl) propane, hexa-
  • the amount of branching agents which may be used is 0.05 mol% to 2 mol%, based in turn on moles of diphenols used in each case.
  • the branching agents can either be introduced with the diphenols and the chain terminators in the aqueous alkaline phase, or added dissolved in an organic solvent before the phosgenation.
  • the polycarbonates according to the invention are both homopolycarbonates and copolycarbonates and mixtures thereof.
  • the polycarbonates according to the invention can be aromatic polyester carbonates or polycarbonates which are present in a mixture with aromatic polyester carbonates.
  • the term polycarbonate is representative of the polycarbonate substrates obtainable by the processes according to the invention.
  • the polycarbonates according to the invention have average molecular weights M w (determined by gel permeation chromatography after prior calibration) of
  • Another subject of the application are polycarbonate substrates with high purity and the optical data carriers which can be produced therefrom with particular stability when irradiated with blue laser light.
  • Optical data carriers according to the invention which can be produced from the high-purity polycarbonate according to the invention are, in particular, those which are read out, can be written to once or can be written to multiple times, a laser beam being used during the reading or writing process.
  • a laser beam in the wavelength range from 390 to 650 nm, particularly preferably from 400 to 450 nm, for writing or reading.
  • the optical data carriers can have one information layer per disc, e.g. in the case of CD audio, the DVD5 or in the case of magneto-optical writing, such as the mini disc, have two information layers, such as the DVD9, the DVD 10 or more than two
  • the optical data carriers are manufactured using known methods such as injection molding or injection molding.
  • the optical data carriers made from the polycarbonates produced according to the invention have a particularly high stability when irradiated with blue laser light. This gives them a longer service life.
  • BPA BPA is melted continuously with sodium hydroxide solution
  • sodium hydroxide solution sodium hydroxide solution
  • the sodium hydroxide solution used has different concentrations and
  • the organic solution is separated from the aqueous solution and, after the organic solution has been heated to 55 ° C., is filtered first with a 0.6 ⁇ a filter and then through a 0.2 ⁇ a filter. After isolation, the poly 2,2-bis (4-hydroxylphenyl) propane carbonate is obtained.
  • Optical data carriers in the format of a compact disk (12 cm in diameter and a thickness of approximately 1.2 mm) are produced from the polycarbonates produced according to experiments 1 and 2.
  • No information structure is embossed on the disc.
  • H. an unstructured matrix is used so that no annoying diffraction effects occur when irradiated with the laser.
  • the discs are not metallized and are not provided with protective lacquer.
  • the discs are produced on a Netstal Discjet 600 CD injection molding machine at cylinder temperatures of 315/340/350 and 350 ° C (intake / compression / cylinder head nozzle), a maximum injection speed of 130 mm / sec and a mold temperature of 55 ° C.
  • the cycle time is 4.9 seconds.
  • the stability of the disks thus produced when irradiated with the blue laser was determined in the following test setup.
  • Laser light with a wavelength of 407 nm and a beam diameter of 1.35 mm from a krypton-ion laser was focused on the disk with the aid of a lens with a focal length of 20 mm.
  • the laser beam diameter in focus is 8.6 ⁇ m, which results in the power density I (GW / m 2 ) in the focus of the laser beam in Table 3.
  • the intensity of the transmitted laser light is registered behind the disc with a photodetector. The times are determined until a significant decrease in the intensity of the transmitted laser light is found. The decrease in light intensity tat means that damage processes occur in the polycarbonate. The tests are carried out with different laser powers.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Information Retrieval, Db Structures And Fs Structures Therefor (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Optical Recording Or Reproduction (AREA)

Abstract

L'invention concerne des supports de données optiques, particulièrement stables lorsqu'ils sont exposés à la lumière de lasers bleus, ainsi qu'un procédé permettant de les produire.
EP00969530A 1999-11-03 2000-10-23 Supports de donnees optiques et procede permettant de les produire Withdrawn EP1240231A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19952849 1999-11-03
DE19952849A DE19952849A1 (de) 1999-11-03 1999-11-03 Optische Datenträger und Verfahren zu ihrer Herstellung
PCT/EP2000/010398 WO2001032747A1 (fr) 1999-11-03 2000-10-23 Supports de donnees optiques et procede permettant de les produire

Publications (1)

Publication Number Publication Date
EP1240231A1 true EP1240231A1 (fr) 2002-09-18

Family

ID=7927750

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00969530A Withdrawn EP1240231A1 (fr) 1999-11-03 2000-10-23 Supports de donnees optiques et procede permettant de les produire

Country Status (11)

Country Link
US (1) US6855390B1 (fr)
EP (1) EP1240231A1 (fr)
JP (1) JP2003527464A (fr)
KR (1) KR20020053835A (fr)
CN (1) CN1387543A (fr)
AU (1) AU7921400A (fr)
BR (1) BR0015255A (fr)
DE (1) DE19952849A1 (fr)
HK (1) HK1052192A1 (fr)
MX (1) MXPA02004398A (fr)
WO (1) WO2001032747A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003026793A (ja) * 2001-07-16 2003-01-29 Teijin Chem Ltd 精製ポリカーボネート樹脂の製造方法
JP2009227840A (ja) * 2008-03-24 2009-10-08 Nippon Zeon Co Ltd 環状オレフィン系付加型重合体を含有する樹脂材料からなる光学成形品

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0653793B2 (ja) 1986-10-22 1994-07-20 出光石油化学株式会社 ポリカ−ボネ−ト有機溶剤液の洗浄方法
JPH0827978B2 (ja) * 1989-01-25 1996-03-21 出光石油化学株式会社 光学式ディスク基板及び該基板を用いた光学式情報記録媒体
US5412060A (en) * 1991-08-20 1995-05-02 Bayer Aktiengesellschaft Process for the production of polycarbonate of constant viscosity
JPH07196783A (ja) 1994-01-07 1995-08-01 Mitsui Toatsu Chem Inc 芳香族ポリカーボネートの製造方法
JP3436466B2 (ja) * 1996-03-07 2003-08-11 出光石油化学株式会社 デジタルビデオディスク基板
DE69634451T2 (de) * 1996-03-28 2005-09-15 Idemitsu Kosan Co., Ltd. Substrat für digital video disk
US6646098B2 (en) * 1998-08-18 2003-11-11 Teijen Chemicals Polycarbonate resin molding material for optical use and optical disk substrate
SG87068A1 (en) * 1999-01-11 2002-03-19 Mitsubishi Gas Chemical Co Process for purifying polycarbonate resin solution

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0132747A1 *

Also Published As

Publication number Publication date
DE19952849A1 (de) 2001-05-10
CN1387543A (zh) 2002-12-25
WO2001032747A1 (fr) 2001-05-10
JP2003527464A (ja) 2003-09-16
AU7921400A (en) 2001-05-14
KR20020053835A (ko) 2002-07-05
US6855390B1 (en) 2005-02-15
BR0015255A (pt) 2002-11-19
HK1052192A1 (zh) 2003-09-05
MXPA02004398A (es) 2002-09-02

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