WO2000037551A1 - Pieces moulees detectables aux rayons x et ayant une stabilite longue duree amelioree - Google Patents

Pieces moulees detectables aux rayons x et ayant une stabilite longue duree amelioree Download PDF

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Publication number
WO2000037551A1
WO2000037551A1 PCT/EP1999/009558 EP9909558W WO0037551A1 WO 2000037551 A1 WO2000037551 A1 WO 2000037551A1 EP 9909558 W EP9909558 W EP 9909558W WO 0037551 A1 WO0037551 A1 WO 0037551A1
Authority
WO
WIPO (PCT)
Prior art keywords
bis
hydroxyphenyl
propane
iodinated
brominated
Prior art date
Application number
PCT/EP1999/009558
Other languages
German (de)
English (en)
Inventor
Martin Döbler
Wolfgang Ebert
Siegfried Neumann
Walter Köhler
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to JP2000589615A priority Critical patent/JP2002533509A/ja
Priority to EP99958171A priority patent/EP1141113A1/fr
Priority to AU15596/00A priority patent/AU1559600A/en
Priority to CA002355139A priority patent/CA2355139A1/fr
Publication of WO2000037551A1 publication Critical patent/WO2000037551A1/fr
Priority to HK02104735.0A priority patent/HK1042912A1/zh

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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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings
    • 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
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
    • C08G64/10—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing halogens
    • 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
    • C08K5/10—Esters; Ether-esters
    • C08K5/109—Esters; Ether-esters of carbonic acid, e.g. R-O-C(=O)-O-R
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
    • A61B90/00—Instruments, implements or accessories specially adapted for surgery or diagnosis and not covered by any of the groups A61B1/00 - A61B50/00, e.g. for luxation treatment or for protecting wound edges
    • A61B90/39—Markers, e.g. radio-opaque or breast lesions markers
    • 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
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent

Definitions

  • the present invention relates to the use of a mixture of at least one brominated and / or iodinated oligo-, poly- and / or copolycarbonates and at least one stabilizer for the production of X-ray-contrasting molded parts made of plastic.
  • Special molded parts in the sense of the present invention are in particular those for medical applications, such as probes or joint parts and toys for
  • Polycarbonate bases are unsuitable for this purpose because their contrast in the X-ray image is too low.
  • a material used for this purpose is e.g. PVC, however, is not transparent.
  • Known iodine-containing polymers also have inadequate mechanical properties and / or are difficult to produce.
  • the task was therefore to develop molding compositions which, with good mechanical properties and high transparency and a glass temperature well above 100 ° C., have a good contrast in X-ray examinations.
  • Dipodyl carbonates containing iodine and their addition to polycarbonates are known from US Pat. No. 3,382,207.
  • iodine-containing phenols are known as chain terminators for polycarbonates. See also the corresponding GB-PA 1 1 63 816.
  • iodine-containing compounds are known as additives to polycarbonates (column 4, line 64; column 5, line 43).
  • X-ray contrast medium The use as an X-ray contrast medium is not described for these materials, nor is it used for the production of X-ray contrastable moldings. It has now been found that molded parts with at least one brominated and / or iodinated oligo-, poly- and / or copolycarbonate are excellent in X-ray contrast, but change color in daylight even in closed rooms. Surprisingly, this can be remedied by adding stabilizers from the benzotriazole series or benzophenone series.
  • the present application accordingly relates to the use of a mixture of at least one brominated and / or iodinated oligo-, poly- and / or copolycarbonates and at least one stabilizer for the production of X-ray-contrasting molded parts made of plastic.
  • Oligo-, poly- or copolycarbonates according to the invention have, for example, an M w between 600 and 100,000, preferably between 1000 and 80,000, particularly preferably between 3,000 and 40,000 and have iodine or bromophenyl carbonate end groups, preferably end groups of the general formula (I) on wherein
  • R 1 to R 3 represent H, C 1 -C 8, optionally branched alkyl, Cl, Br or J, with the proviso that at least one of the radicals R 1, R 2 and R 3 represents J and / or Br.
  • Preferred end groups are 4-iodophenyl carbonate and 2,4,6-triiodophenyl carbonate end groups.
  • the iodophenols are compounds available in the chemical trade or are accessible in organic syntheses from aromatic intermediates, possibly via the detour via diazonium salts. You can individually, in combinations, possibly can also be used in combination with conventional chain terminators such as phenol, p-tert-butylphenol, hexylphenol, i-octylphenol or nonylphenol.
  • Diphenols such as, for example, come as diol components for the oligo-, poly- or copolycarbonates according to the invention with end groups of the general formula (I)
  • Preferred diphenols are 4,4'-dihydroxydiphenyl, 2,2-bis (4-hydroxyphenyl) propane, 2,4-bis (4-hydroxyphenyl) -2-methylbutane, 1,1-bis (4th -hydroxyphenyl) -p-diisopropylbenzene, 2,2-bis (3-methyl-4-hydroxyphenyl) propane, 2,2-bis (3-chloro-4-hydroxyphenyl) propane, bis- (3,5-dimethyl-4-hydroxyphenyl) methane, 2,2-bis (3,5-dimethyl-4-hydroxyphenyl) propane, bis (3,5-dimethyl-4-hydroxyphenyl) sulfone, 2,4-bis (3,5-dimethyl-4-hydroxyphenyl) -2-methylbutane, l, l-bis (3,5-dimethyl-4-hydroxyphenyl) -p-diisopropylbenzene, 2,2- Bis (3,5-dichloro-4-hydroxyphenyl) propane, 2,2-bis
  • diphenols are 2,2-bis (4-hydroxyphenyl) propane, 2,2-bis (3,5-dimethyl-4-hydroxyphenyl) propane, 2,2-bis (3,5-dichloro) -4-hydroxyphenyl) propane, 2,2-bis (3,5-dibromo-4-hydroxyphenyl) propane, 1,1-bis (4-hydroxyphenyl) cyclohexane and 1,1-bis- (4th -hydroxyphenyl) -3,3,5-trimethylcyclohexane.
  • oligo-, poly- or copolycarbonates according to the invention with end groups of the general formula (I) can be linear or branched in a known manner.
  • Suitable branching agents are triphenols, trimesic acid (trichloride), cyanuric acid trichloride and 3,3-bis (3-methyl-4-hydroxyphenyl) -2-oxo-2,3-dihydroindole.
  • oligo-, poly- or copolycarbonates are those with iodinated and / or brominated diols, such as, for example, iodinated or brominated derivatives of hydroquinone, resorcinol, dihydroxydiphenyls, bis (hydroxyphenyl) alkanes, bis (hydroxyphenyl) cycloalkanes , Bis (hydroxyphenyl) sulfides, bis (hydroxyphenyl) ether, bis (hydroxyphenyl) ketones, bis (hydroxyphenyl) sulfones, bis (hydroxyphenyl) sulfoxides, ä, ä'-bis (hydroxyphenyl ) -diisopropylbenzenes, as well as their nuclear alkylated compounds, the iodine and / or bromine atoms preferably sitting on the aromatic nucleus of the diols.
  • iodinated or brominated diols such as, for example, io
  • Preferred iodinated and / or brominated diphenols are the single or multiple iodinated and / or brominated derivatives of 4,4'-dihydroxydiphenyl, 2,2-bis (4-hydroxyphenyl) propane, 2,4-bis ( 4-hydroxyphenyl) -2-methylbutane, 1,1-bis (4-hydroxyphenyl) p-diisopropylbenzene, 2,2-bis (3-methyl-4-hydroxyphenyl) propane, 2,2-bis - (3-chloro-4-hydroxyphenyl) propane, bis (3,5-dimethyl-4-hydroxyphenyl) methane, 2,2-bis (3,5-dimethyl-4-hydroxyphenyl) propane, bis - (3,5-dimethyl-4-hydroxyphenyl) sulfone,
  • Particularly preferred iodinated and / or brominated diphenols are the single or multiple iodinated and / or brominated derivatives of 2,2-bis (4-hydroxyphenyl) propane, 2,2-bis (3,5-dimethyl-4-) hydroxyphenyl) propane, 2,2-bis (3,5-dichloro-4-hydroxyphenyl) propane, 2,2-bis (3,5-dibromo-4-hydroxyphenyl) propane, 1,1-bis - (4-hydroxyphenyl) cyclohexane and l, l-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane.
  • 2,2-bis (3,5-dibromo-4-hydroxyphenyl) propane (tetrabromobisphenol) and / or and 2,2-bis (4-hydroxy) are preferred for the oligo-, poly- and / or copolycarbonates according to the invention -3,5-diiodophenyl) propane (tetraiodobisphenol), optionally in a mixture with one another or optionally with other diols.
  • the oligo-, poly- and / or copolycarbonates according to the invention are preferred in amounts between 0.1 to 100% by weight, preferably 0.1 to 20% by weight, particularly preferably 1 to 10% by weight and very particularly preferably 2 to 7 wt .-% based on the molded part used.
  • the mixture contains a stabilizer from the benzotriazole series in amounts between 0.01 and 10% by weight, preferably in amounts between 0.1 and 1% by weight.
  • Preferred stabilizers are UV absorbers, as described, for example, in EP 0 839 623
  • Benzotriazoles such as, for example, 2- (3 ' , 5- ' bis (1, 1-dimethylbenzyl) -2 ' -hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-5' - (tert -octyl) -phenyl) -benzotriazole, 2- (2'-hydroxy-3 '- (2-butyl) -5' - (tert-butyl) -phenyl) -benzotriazole, bis- (3- (2H-benzotriazolyl) -2-hydroxy-5-tert-octyl) methane.
  • the molded parts there is preferably at least one transparent thermoplastic, preferably a non-halogenated polycarbonate or copolycarbonate in amounts of 85 to 99.9% by weight, preferably 90 to 99% by weight, particularly preferably 93 to 98% by weight, based on the molding included.
  • a transparent thermoplastic preferably a non-halogenated polycarbonate or copolycarbonate in amounts of 85 to 99.9% by weight, preferably 90 to 99% by weight, particularly preferably 93 to 98% by weight, based on the molding included.
  • the polymers of ethylenically unsaturated monomers and / or polycondensates of bifunctional reactive compounds are particularly preferably used as transparent thermoplastics.
  • Particularly suitable transparent thermoplastics are polycarbonates or copolycarbonates based on diphenols.
  • the oligomers according to the invention can, however also with poly- or copolyacrylates and poly- or copolymethacrylates such as poly- or copolymethyl methacrylate, but also as copolymers with styrene such as transparent polystyrene-acrylonitrile (SAN).
  • SAN transparent polystyrene-acrylonitrile
  • Terephthalic acid e.g. Poly or copolyethylene terephthalate (PET or CoPET) or glycol-modified PET (PETG) can be mixed in.
  • PET or CoPET copolyethylene terephthalate
  • PETG glycol-modified PET
  • Thermoplastic, aromatic polycarbonates in the sense of the present invention are both homopolycarbonates and copolycarbonates; the polycarbonates can be linear or branched in a known manner.
  • polycarbonates are produced in a known manner from diphenols, carbonic acid derivatives, optionally chain terminators and optionally branching agents.
  • Diphenols suitable for the preparation of the polycarbonates are, for example, hydroquinone, resorcinol, dihydroxydiphenyls, bis (hydroxyphenyl) alkanes, bis (hydroxyphenyl) cycloalkanes, bis (hydroxyphenyl) sulfides, bis (hydroxyphenyl) ethers, Bis (hydroxyphenyl) ketones, bis (hydroxyphenyl) sulfones, bis (hydroxyphenyl) sulfoxides, ⁇ , ⁇ ′-bis (hydroxyphenyl) diisopropylbenzenes, and also their alkylated compounds.
  • the x-ray-opaque polymer compositions thus obtained can be prepared by the usual methods, e.g. Hot pressing, spinning, extruding or injection molding, can be converted into shaped objects, e.g. Toy parts, but also fibers,
  • the polymer compositions can also be processed into cast films.
  • composition of the invention with a relatively high content of iodine
  • Additives applied in a thin layer to a molded article made of a polymer that is X-ray transparent can take place simultaneously or immediately afterwards with the shaping of the base body, for example by coextrusion or multi-component injection molding. However, it can also be applied to the fully formed base body, for example by lamination with a film or by coating with a solution.
  • the molding compounds are particularly suitable for transparent children's toy parts or for medical applications. Such molded parts are particularly suitable for small parts of children's toys.
  • ⁇ re measured in dichloromethane at 25 ° C. and a concentration of 0.5% by weight.
  • An oligocarbonate containing tetrabromobisphenol can be obtained commercially under the designation Great Lakes BC 52.
  • the brominated and / or iodinated oligo-, poly- and / or copolycarbonates (9.5% by weight) obtained according to Examples 1 to 6 are mixed with polycarbonate based on bisphenol A (Makrolon 2808, Bayer AG) and 0.5% by weight .-% Tinuvin 234 (2- (3 ', 5-'-bis (l, l-dimethylbenzyl) -2 ' -hydroxyphenyl) benzotriazole from Ciba Specialty Chemicals, Basel, Switzerland) as a stabilizer in the usual manner in Mixed methylene chloride. Then a film is made and 200 hours with one Xenon WOM 0.5 W / mm 2 102: 18 weathered. The yellowness index (YI) was measured before and after weathering.
  • YI yellowness index
  • the mixtures can also be processed on an injection molding machine and, for example, molded into building blocks.

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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)
  • Toys (AREA)
  • Materials For Medical Uses (AREA)

Abstract

L'invention concerne l'utilisation d'un mélange contenant au moins un oligo-carbonate, polycarbonate et/ou copolycarbonate bromé et/ou iodé et au moins un stabilisant pour produire des pièces moulées en plastique détectables aux rayons X et ayant une meilleure stabilité longue durée améliorée.
PCT/EP1999/009558 1998-12-18 1999-12-07 Pieces moulees detectables aux rayons x et ayant une stabilite longue duree amelioree WO2000037551A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2000589615A JP2002533509A (ja) 1998-12-18 1999-12-07 改良された長期安定性を有するｘ線コントラスト性成形物
EP99958171A EP1141113A1 (fr) 1998-12-18 1999-12-07 Pieces moulees detectables aux rayons x et ayant une stabilite longue duree amelioree
AU15596/00A AU1559600A (en) 1998-12-18 1999-12-07 X-ray contrasting moulded part with improved long-term stability
CA002355139A CA2355139A1 (fr) 1998-12-18 1999-12-07 Pieces moulees detectables aux rayons x et ayant une stabilite longue duree amelioree
HK02104735.0A HK1042912A1 (zh) 1998-12-18 2002-06-25 具有改進的長期穩定性的可用x射線造影的模製品

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19858787 1998-12-18
DE19858787.2 1998-12-18

Publications (1)

Publication Number Publication Date
WO2000037551A1 true WO2000037551A1 (fr) 2000-06-29

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Application Number Title Priority Date Filing Date
PCT/EP1999/009558 WO2000037551A1 (fr) 1998-12-18 1999-12-07 Pieces moulees detectables aux rayons x et ayant une stabilite longue duree amelioree

Country Status (7)

Country Link
EP (1) EP1141113A1 (fr)
JP (1) JP2002533509A (fr)
CN (1) CN1330682A (fr)
AU (1) AU1559600A (fr)
CA (1) CA2355139A1 (fr)
HK (1) HK1042912A1 (fr)
WO (1) WO2000037551A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006058856A1 (fr) * 2004-12-03 2006-06-08 Ciba Specialty Chemicals Holding Inc. Combinaison de stabiliseurs et d'absorbeurs de rayons ultraviolets
WO2007074138A1 (fr) * 2005-12-23 2007-07-05 Evonik Röhm Gmbh Film de pmma ayant une resistance aux intemperies particulierement elevee et assurant une protection elevee contre le rayonnement u.v.

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107915832B (zh) * 2017-10-19 2020-07-28 复旦大学 X-射线显影的含碘聚碳酸酯/聚酯材料及其制备方法与应用

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4182787A (en) * 1978-06-19 1980-01-08 General Electric Company Optically transparent, radiographically opaque tubing
EP0156219A2 (fr) * 1984-03-13 1985-10-02 Daicel Chemical Industries, Ltd. Composition de résine ignifugeante
EP0183276A2 (fr) * 1984-11-30 1986-06-04 Mitsubishi Rayon Co., Ltd. Composition de résine retardatrice de flamme
EP0272422A2 (fr) * 1986-12-23 1988-06-29 General Electric Company Mélanges de résine polycarbonate et interpolymère modificateur stabilisés contre les radiations UV
EP0311008A2 (fr) * 1987-10-07 1989-04-12 Idemitsu Petrochemical Co. Ltd. Composition de résine de polycarbonate
EP0416404A1 (fr) * 1989-09-07 1991-03-13 Bayer Ag Polycarbonates contenant des absorbeurs UV
JPH04325551A (ja) * 1991-04-25 1992-11-13 Asahi Chem Ind Co Ltd 難燃性強化ポリエチレンテレフタレート樹脂組成物
JPH0641416A (ja) * 1992-07-24 1994-02-15 Nippon Steel Chem Co Ltd 難燃性ポリカーボネート樹脂組成物およびその成形品
JPH06299057A (ja) * 1993-04-19 1994-10-25 Mitsubishi Kasei Corp 芳香族ポリカーボネート樹脂組成物及びそれからなる押出成形シート
JPH0857034A (ja) * 1994-08-25 1996-03-05 Terumo Corp Ｘ線造影性医療用成型品
JPH08311325A (ja) * 1995-05-17 1996-11-26 Idemitsu Petrochem Co Ltd ポリカーボネート樹脂組成物
DE19726191A1 (de) * 1997-06-20 1998-12-24 Bayer Ag Verwendung von Jod-phenyl-carbonat-haltigen Polycarbonaten zur Herstellung von speziellen Formteilen

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4182787A (en) * 1978-06-19 1980-01-08 General Electric Company Optically transparent, radiographically opaque tubing
EP0156219A2 (fr) * 1984-03-13 1985-10-02 Daicel Chemical Industries, Ltd. Composition de résine ignifugeante
EP0183276A2 (fr) * 1984-11-30 1986-06-04 Mitsubishi Rayon Co., Ltd. Composition de résine retardatrice de flamme
EP0272422A2 (fr) * 1986-12-23 1988-06-29 General Electric Company Mélanges de résine polycarbonate et interpolymère modificateur stabilisés contre les radiations UV
EP0311008A2 (fr) * 1987-10-07 1989-04-12 Idemitsu Petrochemical Co. Ltd. Composition de résine de polycarbonate
EP0416404A1 (fr) * 1989-09-07 1991-03-13 Bayer Ag Polycarbonates contenant des absorbeurs UV
JPH04325551A (ja) * 1991-04-25 1992-11-13 Asahi Chem Ind Co Ltd 難燃性強化ポリエチレンテレフタレート樹脂組成物
JPH0641416A (ja) * 1992-07-24 1994-02-15 Nippon Steel Chem Co Ltd 難燃性ポリカーボネート樹脂組成物およびその成形品
JPH06299057A (ja) * 1993-04-19 1994-10-25 Mitsubishi Kasei Corp 芳香族ポリカーボネート樹脂組成物及びそれからなる押出成形シート
JPH0857034A (ja) * 1994-08-25 1996-03-05 Terumo Corp Ｘ線造影性医療用成型品
JPH08311325A (ja) * 1995-05-17 1996-11-26 Idemitsu Petrochem Co Ltd ポリカーボネート樹脂組成物
DE19726191A1 (de) * 1997-06-20 1998-12-24 Bayer Ag Verwendung von Jod-phenyl-carbonat-haltigen Polycarbonaten zur Herstellung von speziellen Formteilen

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 121, no. 4, 25 July 1994, Columbus, Ohio, US; abstract no. 36947, XP002132274 *
CHEMICAL ABSTRACTS, vol. 126, no. 12, 24 March 1997, Columbus, Ohio, US; abstract no. 158302, XP002132275 *
DATABASE WPI Section Ch Week 199252, Derwent World Patents Index; Class A23, AN 1992-429024, XP002132276 *
DATABASE WPI Section Ch Week 199619, Derwent World Patents Index; Class A96, AN 1996-182600, XP002132277 *
PATENT ABSTRACTS OF JAPAN vol. 1995, no. 01 28 February 1995 (1995-02-28) *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006058856A1 (fr) * 2004-12-03 2006-06-08 Ciba Specialty Chemicals Holding Inc. Combinaison de stabiliseurs et d'absorbeurs de rayons ultraviolets
WO2007074138A1 (fr) * 2005-12-23 2007-07-05 Evonik Röhm Gmbh Film de pmma ayant une resistance aux intemperies particulierement elevee et assurant une protection elevee contre le rayonnement u.v.
WO2007073952A1 (fr) * 2005-12-23 2007-07-05 Evonik Röhm Gmbh Film de pmma ayant une resistance aux intemperies particulierement elevee, et assurant une protection elevee contre le rayonnement u.v.
US8088847B2 (en) 2005-12-23 2012-01-03 Evonik Roehm Gmbh PMMA film featuring particularly great weather resistance and great UV protection

Also Published As

Publication number Publication date
JP2002533509A (ja) 2002-10-08
CA2355139A1 (fr) 2000-06-29
CN1330682A (zh) 2002-01-09
EP1141113A1 (fr) 2001-10-10
AU1559600A (en) 2000-07-12
HK1042912A1 (zh) 2002-08-30

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