EP1157065A1 - Melange polymere/copolymere a base de vinylcyclohexane et systeme stabilisateur - Google Patents

Melange polymere/copolymere a base de vinylcyclohexane et systeme stabilisateur

Info

Publication number
EP1157065A1
EP1157065A1 EP00907527A EP00907527A EP1157065A1 EP 1157065 A1 EP1157065 A1 EP 1157065A1 EP 00907527 A EP00907527 A EP 00907527A EP 00907527 A EP00907527 A EP 00907527A EP 1157065 A1 EP1157065 A1 EP 1157065A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
formula
mixture according
stabilizer system
independently
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Withdrawn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
EP00907527A
Other languages
German (de)
English (en)
Inventor
Volker Wege
Konstadinos Douzinas
Friedrich Bruder
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
Teijin Ltd
Original Assignee
Bayer AG
Teijin Ltd
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 AG, Teijin Ltd filed Critical Bayer AG
Publication of EP1157065A1 publication Critical patent/EP1157065A1/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Withdrawn legal-status Critical Current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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1535—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
    • C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • 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
    • G11B7/2533—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 comprising resins

Definitions

  • the present invention relates to a mixture containing vinylcyclohexane (VCH) based polymer / copolymer and a stabilizer system containing lactone, sterically hindered phenol and phosphite component, further to a process for the preparation of this mixture and the use of the mixture for the production of moldings.
  • VCH vinylcyclohexane
  • Homopolymers with sufficient mechanical properties of the vinylcyclohexane-based polymer show a higher viscosity in a wide range of low shear rates at the same temperature compared to polycarbonate, which are currently used to manufacture optical data storage media.
  • JP 01-294 753, JP 5-242 522 are suitable for restricting the reduction in molecular weight in high concentrations, but lead to a considerable reduction in molecular weight even at processing temperatures of approximately 300 ° C.
  • JP 61-138648 describes optical data carriers which are made from i.a. Polymethyl methacrylate, polycarbonate and polystyrene are produced, the polymers containing 2-benzofuranones as stabilizers.
  • the task now is to stabilize VCH-based polymers / copolymers in such a way that processing is also possible at high temperatures without significant reduction in molecular weight.
  • the mixtures according to the invention show no significant molecular weight degradation of the polymer even at elevated temperatures.
  • the invention relates to a mixture comprising A) vinylcyclohexane-based polymer and B) stabilizer system containing lactone, sterically hindered phenol and a phosphite compound.
  • a vinylcyclohexane-based polymer with the recurring structural unit of the formula (I) is preferred
  • R 1 and R 2 are independently hydrogen or Ci-Cg-alkyl, preferably
  • R 3 and R 4 are independently hydrogen or C j -C 6 alkyl, preferably C
  • R 5 represents hydrogen or C ] -C 6 alkyl, preferably C 1 -C 4 alkyl,
  • R 1 , R 2 and R 5 independently of one another in particular represent hydrogen or
  • the linkage can have a small proportion of head-to-head linkage.
  • the VCH preferably have a predominantly isotactic or syndiotactic
  • Diad configuration in particular polymers are preferred with a syndiotactic diad fraction of 50.1 to 74%, very particularly preferably 52 to 70%.
  • comonomers can preferably be used in the polymerization of the starting polymer (optionally substituted polystyrene) and incorporated into the polymer: olefins with generally 2 to 10 carbon atoms, such as, for example, ethylene, propylene, isoprene, isobutylene, butadiene, Ci-Cg, preferably C ⁇ -C 4 - alkyl esters of acrylic or methacrylic acid, unsaturated cycloaliphatic hydrocarbons, for example cyclopentadiene, cyclohexene, cyclohexadiene, optionally substituted norbornene, dicyclopentadiene, dihydrocyclopentadiene, optionally substituted tetracyclododecenes, nuclear alkylated styrenes, divinyl-styrene, ⁇ -methyl-styrene, ⁇ -methyl-styrene, ⁇ -methyl-styrene ,
  • comonomers based on the polymer can be present in the polymer; preference is given to up to 50% by weight, in particular up to 40% by weight, very particularly preferably the polymers can contain 1 to 30% by weight .-% contain comonomers.
  • the vinylcyclohexane (co) polymers generally have absolute molecular weights Mw (weight average) of 1000-10000000, preferably 60,000-1000000, very particularly preferably 70000-600000, determined by light scattering.
  • the copolymers can be present both statistically and as block copolymers.
  • the polymers can have a linear chain structure and also have branching points due to Co units (for example graft copolymers).
  • the branching centers contain, for example, star-shaped or branched polymers.
  • the polymers according to the invention can have other geometric shapes of the primary, secondary, tertiary, optionally quaternary polymer structure. Helix, double helix, leaflet etc. or mixtures of these structures may be mentioned.
  • Block copolymers include di-blocks, tri-blocks, multi-blocks and star-shaped block copolymers.
  • the stabilizer system contains lactone of the formula (I), sterically hindered phenol of the formula (II) and phosphite component of the formula (III), it being possible to use one or more compounds of the formulas (I), (II) and (III).
  • Lactones are preferably compounds of the formula (I)
  • R ', R 2 , R 3 and R 4 independently of one another are hydrogen or C 1 -C 6 -alkyl, preferably C 1 -C 4 -alkyl, optionally a 5- or 6-membered ring, preferably cyclohexyl or cyclopentyl.
  • R 1 and R 2 independently of one another particularly preferably represent branched C3-C 4- alkyl, in particular iso-propyl and / or tert-butyl.
  • a particularly preferred lactone is 5,7-di-t-butyl-3- (3,4-dimethyl-phenyl) -3H-benzofuran-2-one.
  • Sterically hindered phenols are preferably compounds of the formula (II)
  • R 5 and R 6 independently of one another for hydrogen or -CC 6 alkyl, preferably
  • -C-C 4 alkyl optionally a 5- or 6-membered ring, preferably cyclohexyl or cyclopentyl,
  • R 5 and R 6 independently of one another are particularly preferably C 3 -C 4 alkyl, in particular iso-propyl and / or tert-butyl.
  • n stands for an integer from 1 to 4, preferably 3 or 4, in particular
  • a 1 and A 2 independently of one another are C r C 6 alkylene, preferably C 1 -C 4 alkylene, in particular methylene, ethylene.
  • R is independently hydrogen, C j-C6 alkyl, preferably C, -C 4 alkyl,
  • C -C 6 alkoxy preferably C, -C 4 alkoxy, optionally a 5- or 6-membered ring, preferably cyclohexyl or cyclopentyl.
  • Phosphite components are preferably compounds of the formula (III):
  • R 7 and R 8 are independently hydrogen or C j -CG alkyl, preferably C j -C 4 alkyl, membered 6-optionally a 5- or ring, preferably cyclohexyl or cyclopentyl,
  • x and y are independently 0, 1, 2, 3, 4, 5, preferably 0, 1 or 2 and
  • n 1 or 2.
  • R 7 and R 8 independently of one another are particularly preferably C 3 -C 4 -alkyl, in particular isopropyl and / or tert-butyl.
  • n 1
  • the valence of the carbon atom in question is hydrogen or C r C 6 alkyl, C r C 6 alkoxy optionally 5- or 6-membered ring, preferably C ] -C 4 alkyl, preferably with the at R 7 and R 8 radicals bound.
  • the structural formulas given each reflect the main components (> 90%) of the industrially used compounds, which may contain, for example, isomers, starting and secondary compounds in smaller proportions.
  • the stabilizer mixture comprising a lactone derivative I, sterically hindered phenol II and phosphite component III (phosphonite) is generally in parts by weight, based on the polymer used, of from 2% to 0.001%, preferably 1% to 0.005%, and very particularly preferably 0, 6% to 0.01% used.
  • the proportion of the individual components of lactone I, sterically hindered phenol II and phosphite component III (phosphonite) is generally 5 to 95 parts by weight, preferably 10 to 60 parts by weight, the proportions of the individual components adding up to 100.
  • lactones, hindered phenols and phosphite compounds are generally known and are commercially available.
  • VCH (co) polymers are prepared by polymerizing derivatives of styrene with the corresponding monomers by radical, anionic, cationic, or by metal complex initiators or catalysts and then hydrogenating the unsaturated aromatic bonds completely or partially (cf., for example, WO 94 / 21694, EP-A 322 731).
  • the polymers based on vinylcyclohexane generally have virtually complete hydrogenation of the aromatic units.
  • the degree of hydrogenation is> 80%, preferably> 90%, very particularly preferably> 99% to 100%.
  • the degree of hydrogenation can be determined, for example, by NMR or UV spectroscopy.
  • the starting polymers are generally known (e.g. WO 94/21694).
  • the amount of catalyst used depends on the process carried out, which can be carried out continuously, semi-continuously or batchwise.
  • the ratio of catalyst to polymer for example in the batch process, is generally 0.3-0.001, preferably 0.2-0.005, particularly preferably 0.15-0.01.
  • the hydrogenation of the starting polymers is carried out according to generally known methods (e.g. WO 94/21 694, WO 96/34 895, EP-A-322 731).
  • a large number of known hydrogenation catalysts can be used as catalysts.
  • Preferred metal catalysts are mentioned, for example, in WO 94/21 694 or WO 96/34 896.
  • Any catalyst known for the hydrogenation reaction can be used as the catalyst.
  • Catalysts with a large surface area e.g.
  • catalysts with a small surface area (for example> 10 m 2 / g) and large average pore diameters are also suitable, which are characterized in that 98% of the pore volume has pores with pore diameters greater than 600 ⁇ (for example approx. 1,000 - 4,000 ⁇ ) (see, for example, US-A 5,654,253, US-A 5,612,422, JP-A 03076706).
  • Raney nickel, nickel on silicon dioxide or silicon dioxide / aluminum oxide, nickel on carbon are used as supports and / or noble metal catalysts, for example Pt, Ru, Rh, Pd.
  • the reaction is generally carried out at temperatures between 0 and 380 ° C., preferably between 20 and 250 ° C., in particular between 60 and 200 ° C.
  • the reaction is generally carried out at pressures of 1 to 1000 bar, preferably 20 to 300 bar, in particular 40 to 200 bar.
  • the stabilizer can be in solution at any point in the manufacturing process of the vinylcyclohexane based polymer before or after a process step. be introduced in the solid, liquid or gaseous state.
  • the process steps optionally include a polymerization which leads to a prepolymer, for example polystyrene derivative, optionally a hydrogenation of the prepolymer, optionally an evaporation step and optionally an extrusion or compounding of the vinylcyclohexane-based polymer.
  • the vinylcyclohexane-based polymers or copolymers stabilized according to the invention are excellent for the production of moldings and films. These are also particularly suitable for producing optical data memories, preferably with densities of data storage> 5, in particular> 10 gigabytes, based on a disk with a diameter of 120 mm.
  • the mixtures according to the invention can contain at least one of the customary additives, such as lubricants and mold release agents, nucleating agents, antistatic agents, stabilizers and dyes and pigments.
  • customary additives such as lubricants and mold release agents, nucleating agents, antistatic agents, stabilizers and dyes and pigments.
  • the mixtures according to the invention are prepared by mixing the vinylcyclohexane-based polymers or copolymers with the stabilizer system and, if appropriate, further additives and compounding them at elevated temperatures (generally> 230 ° C.).
  • optical data storage media The following are examples of optical data storage media:
  • MO disc Magneto-optical disc
  • MD Magneto-optical disc
  • MAMMOS Magnetic Amplifying magneto optical system
  • CDs CD-R (recordable), CD-RW (rewritable), CD-I (interactive), Photo-CD Super audio CD
  • DVD, DVD-R (recordable), DVD-RAM (random access memory); DVD Digital versatile disc DVD-RW (rewritable) - PC + RW (Phase change and rewritable)
  • MMVF multimedia video file system
  • the polymers according to the invention are furthermore particularly suitable for producing optical materials, for example for lenses, prisms, mirrors, color filters etc. Furthermore, as media for holographic images (for example check cards, credit cards, ID cards, three-dimensional holographic images) .
  • the materials can be used as transparent media for inscribing three-dimensional structures, for example from focused coherent radiation (LASER), in particular as three-dimensional data storage or for three-dimensional imaging of objects.
  • LASER focused coherent radiation
  • the polymers according to the invention are particularly suitable as matrix material for photoaddressable polymers. In addition to the general effect of thermal stabilization, the addition of the stabilizer also leads to better mold release from the injection molding tool.
  • a 40 1 autoclave is flushed with inert gas (nitrogen).
  • inert gas nitrogen
  • Catalyst are added (Table 1). After sealing, the protective gas is then exposed to hydrogen several times. After relaxation, the respective hydrogen pressure is set and heated to the corresponding reaction temperature with stirring. The reaction pressure is kept constant after the onset of hydrogen absorption.
  • the relative molecular weights of the hydrogenated polystyrene are (measured according to GPC in tetrahydrofuran on polystyrene standards)
  • Example 1 (comparison): 106,000 g / mol
  • Example 2 (comparison): 161,000 g / mol
  • Example 3 (according to the invention): 167,000 g / mol
  • Table 2 shows the amount of stabilizer and the relative molecular weights of the polymers based on vinylcyclohexane after extrusion.
  • Comparative example 1 shows that without the addition of a stabilizer, a drastic molecular weight reduction (Mw) takes place at a processing temperature of 240 ° C.
  • the stabilizer system which consists only of a sterically hindered phenol and a phosphorus compound, has the disadvantage that in the for

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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)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)

Abstract

Cette invention concerne un mélange comprenant: A) un polymère à base de vinylcyclohexane (VCH) et B) un système stabilisateur contenant de la lactone, du phénol à encombrement stérique et des éléments phosphite. L'invention concerne également un procédé de production de ce mélange et l'utilisation de ce mélange pour la production de pièces moulées, telles que des supports optiques d'informations.
EP00907527A 1999-02-19 2000-02-09 Melange polymere/copolymere a base de vinylcyclohexane et systeme stabilisateur Withdrawn EP1157065A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19906983 1999-02-19
DE19906983A DE19906983A1 (de) 1999-02-19 1999-02-19 Mischung aus Vinylcyclohexan basierenden Polymer/Copolymer und Stabilisatorsystem
PCT/EP2000/001026 WO2000049078A1 (fr) 1999-02-19 2000-02-09 Melange polymere/copolymere a base de vinylcyclohexane et systeme stabilisateur

Publications (1)

Publication Number Publication Date
EP1157065A1 true EP1157065A1 (fr) 2001-11-28

Family

ID=7898028

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00907527A Withdrawn EP1157065A1 (fr) 1999-02-19 2000-02-09 Melange polymere/copolymere a base de vinylcyclohexane et systeme stabilisateur

Country Status (14)

Country Link
US (1) US6803397B1 (fr)
EP (1) EP1157065A1 (fr)
JP (1) JP2002537430A (fr)
KR (1) KR20010102253A (fr)
CN (1) CN1183189C (fr)
AU (1) AU762336B2 (fr)
BR (1) BR0008291A (fr)
CA (1) CA2362824A1 (fr)
DE (1) DE19906983A1 (fr)
HK (1) HK1045164B (fr)
RU (1) RU2246507C2 (fr)
TW (1) TW500750B (fr)
WO (1) WO2000049078A1 (fr)
ZA (1) ZA200106156B (fr)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61138648A (ja) 1984-12-10 1986-06-26 Mitsui Petrochem Ind Ltd 光学デイスク
JPH0794496B2 (ja) 1987-11-18 1995-10-11 日本合成ゴム株式会社 光学材料
JP2586575B2 (ja) * 1988-05-23 1997-03-05 三菱化学株式会社 光ディスク基板
US4911966A (en) 1988-12-02 1990-03-27 Mitsubishi Monsanto Chemical Company Optical disk substrate
JP3393655B2 (ja) 1992-02-27 2003-04-07 パイオニア株式会社 光ディスクプレーヤ
WO1999003915A1 (fr) * 1997-07-14 1999-01-28 Dover Chemical Corporation Melanges lactones/phosphites
WO1999041307A1 (fr) 1998-02-17 1999-08-19 The Dow Chemical Company Compositions polymeres aromatiques hydrogenees contenant des stabilisants

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0049078A1 *

Also Published As

Publication number Publication date
DE19906983A1 (de) 2000-08-31
TW500750B (en) 2002-09-01
HK1045164A1 (en) 2002-11-15
CN1344288A (zh) 2002-04-10
BR0008291A (pt) 2001-11-06
CN1183189C (zh) 2005-01-05
US6803397B1 (en) 2004-10-12
WO2000049078A1 (fr) 2000-08-24
ZA200106156B (en) 2002-07-26
AU762336B2 (en) 2003-06-26
JP2002537430A (ja) 2002-11-05
HK1045164B (zh) 2005-08-19
CA2362824A1 (fr) 2000-08-24
AU2908600A (en) 2000-09-04
KR20010102253A (ko) 2001-11-15
RU2246507C2 (ru) 2005-02-20

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