WO2001016225A1 - Röntgenkontrasierbare kunststoffformteile - Google Patents
Röntgenkontrasierbare kunststoffformteile Download PDFInfo
- Publication number
- WO2001016225A1 WO2001016225A1 PCT/EP2000/007983 EP0007983W WO0116225A1 WO 2001016225 A1 WO2001016225 A1 WO 2001016225A1 EP 0007983 W EP0007983 W EP 0007983W WO 0116225 A1 WO0116225 A1 WO 0116225A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- iodobenzoic acid
- plastic
- parts
- ray
- bis
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
-
- 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
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0442—Polymeric X-ray contrast-enhancing agent comprising a halogenated group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
Definitions
- the application relates to the use of derivatives of iodobenzoic acid for the production of X-ray-controllable molded articles made of plastic and plastics,
- Plastic molding compositions and plastic moldings containing at least one derivative of iodobenzoic acid are disclosed.
- Bodies can be detected. Furthermore, these materials should have sufficient light stability, at least for use in the interior of buildings.
- the present application therefore relates to the use of iodobenzoic acid derivatives as X-ray contrast media, in particular in plastics, in particular for transparent plastics, and also plastics, plastic molding compositions and plastic moldings containing at least one ester of iodobenzoic acid.
- iodobenzoic acid is amides, alkylamides, dialkylamides and in particular esters.
- Esters and amides which are prepared from mono- or polyhydric, aliphatic or aromatic alcohols or amines are preferred.
- Aliphatic alcohols and amines are exemplary and preferably alcohols and amines having 1 to 30 carbon atoms.
- the carbon chain can be linear or branched.
- the carbon chain can contain one or more alcohol or amine functionalities, and the alcohol or amine functionality can be located anywhere in the carbon chain.
- the alcohol can also be halogenated.
- Esters based on methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, tert-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol are preferred.
- mixed esters for example partly with an iodobenzoic acid and partly with another acid, or incompletely esterified compounds are also suitable according to the invention.
- Aromatic alcohols are especially phenols and bisphenols.
- the iodobenzoic acid derivatives can also be halogenated with F, Cl or Br.
- Non-halogenated monoiodobenzoic acid derivatives are preferred, and the derivatives of 4-iodobenzoic acid are particularly preferred.
- the derivatives of iodobenzoic acid are known or are produced by known methods.
- the derivatives of iodobenzoic acid are preferably used in amounts of 0.001 to
- Plastic is preferably understood to mean thermoplastics, in particular transparent thermoplastics, preferably the polymers of ethylenically unsaturated monomers and / or polycondensates of bifunctional reactive compounds.
- plastics are polycarbonates or copolycarbonates based on diphenols, the poly- or copolyacrylates and poly- or copolymethacrylates such as, for example and preferably, polymethyl methacrylate, poly- or copolymers with styrene, for example and preferably transparent polystyrene or polystyrene.
- rolacrylnitril SAN
- transparent thermoplastic polyurethanes such as for example and preferably transparent polypropylene types, or polyolefins based on cyclic olefins (for example, TOPAS ®, Hoechst), poly- or copoly condensates of terephthalic acid, such as for example and preferably poly- or Copolyethylene terephthalate (PET or CoPET) or glycol-modified PET
- Polycarbonates or copolycarbonates in particular non-halogenated polycarbonates and / or copolycarbonates with molecular weights M w between 600 and 100,000, preferably between 2,000 and 80,000, particularly preferably between 18,000 and 40,000, are particularly preferred.
- 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.
- the polycarbonates can also be fully or partially brominated.
- polycarbonates are produced in a known manner from diphenols, carbonic acid derivatives, optionally chain terminators and optionally branching agents.
- 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.
- Preferred branching agents are triphenols, trimesic acid (trichloride), cyanuric acid trichloride and 3,3-bis- (3-methyl-4-hydroxyphenyl) -2-oxo-2,3-dihydroindole.
- thermoplastics preferably poly- and copolycarbonates
- stabilizers as described, for example, in EP 0 839 623 AI or EP 0 500 496 AI
- thermal stabilizers in particular organic hindered phenols, hindered amines (HALS), phosphites or phosphines, by way of example and preferably triphenylphosphine
- mold release agents by way of example and preferably fatty acid esters of glycerol or tetramethanolmethane, where unsaturated fatty acid can also be completely or partially epoxidized, in particular glycerol monostearate or Pentaerythritol tetrastearate (PETS), flame retardants, antistatic agents, UV absorbers, for example and preferably hydroxybenzotriazoles and hydroxytriazines, fillers, foaming agents, dyes, pigments, optical brighten
- esters of iodobenzoic acid and optionally the additives or mixtures of the additives is carried out in a generally customary manner, for example before or during the polymerization or by subsequent mixing with the plastic, preferably by extrusion.
- plastic compositions obtained in this way are generally in the form of solutions, dispersions, emulsions, dusts, powders, granules, platelets or flakes (molding compositions) and are used for the production of shaped articles (molded articles).
- the production of plastic moldings is carried out using conventional methods such as Hot pressing, spinning, extruding or injection molding.
- the plastic compositions according to the invention generally contain 0.01-10% by weight, preferably 1-3% by weight of organically bound iodine.
- Shaped objects are preferably translucent objects, in particular for medical applications, such as, for example, and preferably probes or joint parts or small objects that are used by children.
- customary shaped objects such as foils, tapes, plates, multi-wall sheets, multi-wall sheets, vessels, pipes and others can also be used
- Plastic compositions according to the invention are produced with the plastic compositions according to the invention.
- the plastic compositions can also be processed into cast films.
- the invention for the production of multilayer systems is also of interest.
- the invention contemporary plastic composition in a thin layer on a molded object made of a plastic that is not with an X-ray contrast agent.
- the application can take place simultaneously with or immediately after the shaping of the molded body, for example by coextrusion or multi-component injection molding.
- the application can also be done on the finished molded body, for example by lamination with a film or by coating with a solution.
- Esters of iodobenzoic acid-containing plastic compositions are preferred for the production of small parts which are used by children, in particular for the production of toys such as building blocks.
- the Farbmuste ⁇ lättchen from Example 2 are examined for their light stability by irradiation with a UV lamp, a Xe-WOM lamp and daylight. The results are given in Table 1.
- ethylene glycol-bis-4-jodbenzoeklareester from Example 1 are dissolved with 96 parts of polymethyl methacrylate (Plexiglas ®) in 150 parts of methylene chloride, and processed to give a 180 .mu.m thick film and dried in vacuo. The film is then exposed for 8 hours under a UV lamp at 254 nm. No discoloration can be detected visually. Furthermore, the VIS spectra between 400 and 1200 nm are congruent before and after the UV irradiation within the scope of the measurement accuracy.
- a cast film made of Makrolon 2808 with 5% of the product from Example 5 is produced using methylene chloride.
- the film is transparent and colorless. No discoloration of the eye can be observed when the film is exposed to UV light at 254 nm for 14 h.
- Samples with a thickness of 2 mm are weathered for 1000 h under Xe-WOM 0.35 W / m 2 without irrigation.
- the previously colorless samples were then colored intensely red.
- a clearly visible red color can also be produced.
- a solution film consisting of 50 parts Makrolon 3208, 50 parts oligomer according to Comparative Example 4 and 0.5 part Tinuvin 234 is produced.
- the film shows no discoloration even after exposure for 6 hours under a UV lamp (254 nm).
- a film consisting of 96 parts Makrolon 2808 and 4 parts 1,4-diiodotetrafluorobenzene (Aldrich) is produced by solution casting. After drying, the colorless and transparent film is exposed to a UV lamp at 254 nm for 6 hours. A clear red color can then be seen.
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Materials For Medical Uses (AREA)
- Analysing Materials By The Use Of Radiation (AREA)
Abstract
Description
Claims
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00960464A EP1228131A1 (de) | 1999-08-27 | 2000-08-16 | Röntgenkontrasierbare kunststoffformteile |
CA002382954A CA2382954A1 (en) | 1999-08-27 | 2000-08-16 | Radio-opaque molded plastic parts |
IL14780500A IL147805A0 (en) | 1999-08-27 | 2000-08-16 | Radio-opaque molded plastic parts |
KR1020027002471A KR20020021814A (ko) | 1999-08-27 | 2000-08-16 | 방사선 비투과성 플라스틱 성형체 |
MXPA02002040A MXPA02002040A (es) | 1999-08-27 | 2000-08-16 | Piezas moldeadas de material sintetico opacas a los rayos x. |
AU72764/00A AU7276400A (en) | 1999-08-27 | 2000-08-16 | Radio-opaque molded plastic parts |
BR0013546-1A BR0013546A (pt) | 1999-08-27 | 2000-08-16 | Peças moldadas de material plástico contrastáveis aos raios x |
JP2001520776A JP2003508569A (ja) | 1999-08-27 | 2000-08-16 | X線検出可能な成形体 |
NO20020732A NO20020732L (no) | 1999-08-27 | 2002-02-13 | Röntgenkontrasterbare plastformdeler |
HK03102028.9A HK1050021A1 (zh) | 1999-08-27 | 2003-03-19 | X-射線可對比的塑料模制體 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19940862A DE19940862A1 (de) | 1999-08-27 | 1999-08-27 | Röntgenkontrastierbare Kunststoffformteile |
DE19940862.9 | 1999-08-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001016225A1 true WO2001016225A1 (de) | 2001-03-08 |
Family
ID=7919914
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/007983 WO2001016225A1 (de) | 1999-08-27 | 2000-08-16 | Röntgenkontrasierbare kunststoffformteile |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP1228131A1 (de) |
JP (1) | JP2003508569A (de) |
KR (1) | KR20020021814A (de) |
CN (1) | CN1371405A (de) |
AU (1) | AU7276400A (de) |
BR (1) | BR0013546A (de) |
CA (1) | CA2382954A1 (de) |
DE (1) | DE19940862A1 (de) |
HK (1) | HK1050021A1 (de) |
IL (1) | IL147805A0 (de) |
MX (1) | MXPA02002040A (de) |
NO (1) | NO20020732L (de) |
WO (1) | WO2001016225A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8404338B2 (en) | 2008-09-30 | 2013-03-26 | Sabic Innovative Plastics Ip B.V. | X-ray and/or metal detectable articles and method of making the same |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20190057291A (ko) * | 2016-09-22 | 2019-05-28 | 코베스트로 도이칠란트 아게 | 감소된 두께를 갖는 투명 성형품 |
EP3930770A1 (de) | 2019-02-28 | 2022-01-05 | Speed Care Mineral GmbH | Paste für die markierung von textilen gebilden und/oder anderweitigen röntgenkontrastunfähigen erzeugnissen |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3645955A (en) * | 1970-03-18 | 1972-02-29 | Scient Tube Products Inc | Plasticized radiopaque vinyl resin compositions |
US4283447A (en) * | 1979-05-18 | 1981-08-11 | Flynn Vincent J | Radiopaque polyurethane resin compositions |
EP0684222A1 (de) * | 1994-05-26 | 1995-11-29 | The London Hospital Medical College | Monomere (Meth)acrylate und damit hergestellte künstliche Gebisscompositionen |
WO2000036002A1 (de) * | 1998-12-11 | 2000-06-22 | Bayer Aktiengesellschaft | Röntgenkontrastierbare kunststofformmassen |
-
1999
- 1999-08-27 DE DE19940862A patent/DE19940862A1/de not_active Withdrawn
-
2000
- 2000-08-16 JP JP2001520776A patent/JP2003508569A/ja active Pending
- 2000-08-16 MX MXPA02002040A patent/MXPA02002040A/es not_active Application Discontinuation
- 2000-08-16 CN CN00812092A patent/CN1371405A/zh active Pending
- 2000-08-16 IL IL14780500A patent/IL147805A0/xx unknown
- 2000-08-16 KR KR1020027002471A patent/KR20020021814A/ko not_active Application Discontinuation
- 2000-08-16 BR BR0013546-1A patent/BR0013546A/pt not_active Application Discontinuation
- 2000-08-16 EP EP00960464A patent/EP1228131A1/de not_active Withdrawn
- 2000-08-16 WO PCT/EP2000/007983 patent/WO2001016225A1/de not_active Application Discontinuation
- 2000-08-16 AU AU72764/00A patent/AU7276400A/en not_active Abandoned
- 2000-08-16 CA CA002382954A patent/CA2382954A1/en not_active Abandoned
-
2002
- 2002-02-13 NO NO20020732A patent/NO20020732L/no unknown
-
2003
- 2003-03-19 HK HK03102028.9A patent/HK1050021A1/zh unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3645955A (en) * | 1970-03-18 | 1972-02-29 | Scient Tube Products Inc | Plasticized radiopaque vinyl resin compositions |
US4283447A (en) * | 1979-05-18 | 1981-08-11 | Flynn Vincent J | Radiopaque polyurethane resin compositions |
EP0684222A1 (de) * | 1994-05-26 | 1995-11-29 | The London Hospital Medical College | Monomere (Meth)acrylate und damit hergestellte künstliche Gebisscompositionen |
WO2000036002A1 (de) * | 1998-12-11 | 2000-06-22 | Bayer Aktiengesellschaft | Röntgenkontrastierbare kunststofformmassen |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8404338B2 (en) | 2008-09-30 | 2013-03-26 | Sabic Innovative Plastics Ip B.V. | X-ray and/or metal detectable articles and method of making the same |
Also Published As
Publication number | Publication date |
---|---|
CN1371405A (zh) | 2002-09-25 |
AU7276400A (en) | 2001-03-26 |
DE19940862A1 (de) | 2001-03-01 |
KR20020021814A (ko) | 2002-03-22 |
HK1050021A1 (zh) | 2003-06-06 |
JP2003508569A (ja) | 2003-03-04 |
MXPA02002040A (es) | 2002-10-31 |
NO20020732D0 (no) | 2002-02-13 |
NO20020732L (no) | 2002-02-13 |
CA2382954A1 (en) | 2001-03-08 |
BR0013546A (pt) | 2002-05-14 |
IL147805A0 (en) | 2002-08-14 |
EP1228131A1 (de) | 2002-08-07 |
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