CN1330688A - Use of polycarbonates containing iodine and/or bromine for moulded parts with high x-ray contrast and moulded parts produced with same - Google Patents

Use of polycarbonates containing iodine and/or bromine for moulded parts with high x-ray contrast and moulded parts produced with same Download PDF

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Publication number
CN1330688A
CN1330688A CN99814500A CN99814500A CN1330688A CN 1330688 A CN1330688 A CN 1330688A CN 99814500 A CN99814500 A CN 99814500A CN 99814500 A CN99814500 A CN 99814500A CN 1330688 A CN1330688 A CN 1330688A
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preferred
contain
bromination
iodinating
polycarbonate
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M·德布勒
S·纽曼
A·布伦纳
W·科勒
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Bayer AG
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    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • 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
    • A—HUMAN NECESSITIES
    • A63—SPORTS; GAMES; AMUSEMENTS
    • A63H—TOYS, e.g. TOPS, DOLLS, HOOPS OR BUILDING BLOCKS
    • A63H33/00—Other toys
    • A63H33/001—Toy-moulding appliances; Toy moulding

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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)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Toys (AREA)
  • Materials For Medical Uses (AREA)
  • Laminated Bodies (AREA)

Abstract

The invention relates to the use of thermoplastic materials containing iodine and/or bromine for moulded parts with high X-ray contrast. The invention also relates to moulded parts produced therewith, notably toys and medical devices.

Description

Purposes and the thus moulded parts of material produce of the polycarbonate that contains iodine and/or bromine in having the moulded parts of high x-ray contrast
The present invention relates to contain the purposes of thermoplastic material in moulded parts of iodine and/or bromine with high x-ray contrast (contrast).The present invention also relates to the moulded parts with this material produce, particularly toy and medical equipment.
Concerning medical field and toy for children, wish that material has high as far as possible transparency and mechanical property as well as possible, and, in carrying out human body X-X-ray examination X process, can be detected.Opposite with metal object, X-ray photograph can not identify the object of being made by plastic material usually, or can only discern very poorly.By suitable additive, but can make this type of moulding compound become X-light radiography.
By suitable additive, but can make become X-ray radiography of this type of moulding compound.
For example among the DE-A 195 45 289 such moulding compound has been described.In this patent, described and for example added BaSO 4But the X-ray radiography ABS type thermoplastic composition.
In addition, Silberman-Hazony, Encycl.Polym.Sci.Eng. (1988), 14,1-8 has described the detectable plastic composition of X-ray.It has described the thermoplastic material that contains various heavy metals as x-ray contrast agent.It has also mentioned the Halogen trimer.
At last, FR 2223403 has described PVC and other and the vinyl polymer that contains iodo-salicylic acid, phenylformic acid and ester thereof, they and US 3 361 700 and US 3 645 955 disclosed polymer analog.Yet PVC is not suitable for the situation of requirement high-clarity and favorable mechanical performance.
US 3 469 704 and DE-A 17 20 812 have also described the transparent plastics moulding compound with the polycarbonate that contains the iodine end group.Yet this method can only be incorporated into end group with iodine.All other monomer does not still have modification, so the weight ratio of iodine is restricted.
At last, US 3 382 207 discloses and has contained the additive of iodine diphenyl carbonate as polycarbonate.
For clear plastic articles, but still do not have in the prior art available suitable X-ray radiography plastics composite.Consider the mechanical property that polycarbonate is outstanding, it still is used for particularly high mechanical stress and transparent toy for children goods so far.Therefore, must develop a kind of plastic material, it can be discerned in the X ray image of routine when keeping high-clarity and mechanical property only to be subjected to small as far as possible change.Plastic material still can be identified layer thickness should be low as far as possible, and be at most 1.2mm.
Therefore, the objective of the invention is to develop a kind of favorable mechanical performance and transparency and in X-ray examination, have the moulding compound that abundant contrast gradient combines.Because moulding compound is the material that is used to produce toy for children,, should avoid adding heavy metal so consider from toxicology.
Therefore, the present invention relates to contain iodine and/or the purposes of bromated transparent thermoplastic material in moulded parts with high X-ray contrast.Relevant therewith suitable be the polycondensate of the polymkeric substance of ethylenically unsaturated monomer and/or the difunctionality active compound that contains bromine or iodine.
Specially suitable plastic material is based on the polycarbonate or the Copolycarbonate of diphenol.Yet, also can with oligopolymer of the present invention and polycarbonate or Copolycarbonate and polymethacrylate or copolymerization methacrylic ester for example bromination and/or iodinating polymethylmethacrylate or copolymerization methyl methacrylate, and with cinnamic multipolymer, polystyrene-vinyl cyanide for example transparent bromination and/or iodinating (SAN) uses together.
In addition, above-mentioned plastic material also can also mix with polycondensate or co-condensation polymer PET (PETG) for example poly-or co-polyethylene terephthalate (PET or CoPET) or glycol modification transparent bromination and/or iodinating cycloolefin, terephthalic acid.
Bromination and/or iodinating polycarbonate is the moulded parts that very preferably is suitable for having high X ray contrast, and wherein, polycarbonate contains diphenol and its weight-average molecular weight M of iodinating and/or bromination wBe 500 to 100000, preferred 1000 to 40000 and preferred especially 1000 to 8000.
The mixture that contains iodine compound that all are above-mentioned also is fit to.
Specially suitable is polycarbonate, its as two phenol units contain 0.1 to 100wt%, the bromination of preferred 1 to 100wt%, preferred especially 10 to 100wt%, preferred 100wt% and/or iodinating 2,2-two (4-hydroxy phenyl) propane.Preferred especially suitable diphenol is 2,2-two (3,5-two bromo-4-hydroxy phenyls) propane (tetrabromobisphenol) and 2,2-two (4-hydroxyl-3,5-diiodo-phenyl) propane (tetraiodo bis-phenol).
Moulded parts can be fully by containing iodine and/or bromated polycarbonate is formed.Like this, the content of iodine in the moulded parts and/or bromine is 0.2 to 70wt%, preferred 1 to 25wt% and preferred especially 2 to 15wt%.
Yet, also can comprise other component.Like this, the amount that contains iodine and/or bromated polycarbonate that moulded parts contains is 0.1 to 100wt%, preferred 1 to 30wt%, preferred especially 2 to 20wt% and very particularly preferably 2 to 10wt% with respect to moulded parts.
In addition, moulded parts can be chosen wantonly and contain at least a transparent thermoplastic material, preferred non-halogenated polycarbonate or Copolycarbonate, and its amount with respect to moulded parts is 70 to 99wt%, preferred 80 to 98wt% and preferred especially 90 to 98wt%.
Especially preferably the polycondensate that uses the polymkeric substance of ethylenically unsaturated monomer and/or difunctionality active compound is as the transparent thermoplastic material.
Specially suitable transparent thermoplastic material comprises based on the polycarbonate of diphenol or Copolycarbonate.Yet, oligopolymer of the present invention also can with polycarbonate or Copolycarbonate and polymethacrylate or copolymerization methacrylic ester for example polymethylmethacrylate or copolymerization methyl methacrylate, and as using with for example transparent polystyrene-vinyl cyanide of cinnamic multipolymer (SAN).
In addition, they can with transparent cycloolefin, the polycondensate or the co-condensation polymer of terephthalic acid, for example poly--or the PET (PETG) of co-polyethylene terephthalate (PET or CoPET) or glycol modification mix.
Those skilled in the art uses polycarbonate and/or Copolycarbonate, preferred non-halogenated polycarbonate and/or Copolycarbonate to obtain splendid result.
Thermoplasticity aromatic copolycarbonate in the scope of the invention comprises homo-polycarbonate and Copolycarbonate; Polycarbonate can be straight chain or with known method branching.
The production of these polycarbonate by diphenol, carbonic acid derivatives, randomly chain terminator and randomly branching agent carry out with known method.
The details of producing polycarbonate are disclosed in the many patent specifications over about 40 years.For example can be with reference to following document: Schnell " polycarbonate chemistry and physics ", polymkeric substance commentary, the 9th volume, inner Science Press, New York, London, Sydney 1964; D.Freitag, U.Grigo, P.R.m ü ller, H.Nouvertne, BAYER AG, " polycarbonate " in polymer science and the engineering encyclopedia, the 11st volume, second edition, 1988,648-718 page or leaf and Dres.U.Grigo, K.Kirchner and P.R.M ü ller be at Becher/Braun, Kunstoff-Handbuch, Vol.3/1, " polycarbonate " in polycarbonate, polyacetal, polyester and the cellulose ester, Carl Hanser Verlag M ü nich, Vienna, 1992, the 117-299 page or leaf.
The suitable diphenol that is used to produce polycarbonate is for example Resorcinol, Resorcinol, dihydroxybiphenyl, two (hydroxy phenyl) alkane, two (hydroxy phenyl) naphthenic hydrocarbon, two (hydroxy phenyl) thioether, two (hydroxy phenyl) ether, two (hydroxy phenyl) ketone, two (hydroxy phenyl) sulfone, two (hydroxy phenyl) sulfoxide, α, α '-two (hydroxy phenyl) diisopropyl benzene, and alkylating compound on their ring.
The iodate of these diphenol and/or the derivative of bromination also are applicable to produces polycarbonate of the present invention and/or Copolycarbonate.
What be preferred for polycarbonate of the present invention and/or Copolycarbonate is tetrabromobisphenol and/or tetraiodo bis-phenol, randomly their intermingling or randomly they mix with other diphenol.
The multipolymer that is preferred for polycarbonate of the present invention and/or Copolycarbonate is tetrabromobisphenol and the dihydroxyphenyl propane multipolymer as comonomer.
The mixture that is preferred for polycarbonate of the present invention and/or Copolycarbonate is the mixture of polymers of the polymkeric substance and the dihydroxyphenyl propane of tetrabromobisphenol.
Polycarbonate and/or the preferred diphenol of Copolycarbonate for other are 4,4 '-dihydroxybiphenyl, 2,2-two (4-hydroxy phenyl) propane, 2,4-two (4-hydroxy phenyl)-2-methylbutane, 1,1-two (4-hydroxy phenyl)-p-diisopropyl benzene, 2,2-two (3-methyl-4-hydroxy phenyl) propane, 2,2-two (3-chloro-4-hydroxy phenyl) propane, two (3,5-dimethyl-4-hydroxy phenyl) methane, 2,2-two (3,5-dimethyl-4-hydroxy phenyl) propane, two (3,5-dimethyl-4-hydroxy phenyl) sulfone, 2,4-two (3,5-dimethyl-4-hydroxy phenyl)-2-methylbutane, 1,1-two (3,5-dimethyl-4-hydroxy phenyl)-the p-diisopropyl benzene, 2,2-two (3,5-two chloro-4-hydroxy phenyls) propane, 2,2-two (3,5-two bromo-4-hydroxy phenyls) propane and 1,1-two (4-hydroxy phenyl)-3,3, the 5-trimethyl-cyclohexane.
Polycarbonate and/or the particularly preferred diphenol of Copolycarbonate for other are 2,2-two (4-hydroxy phenyl) propane, 2,2-two (3,5-dimethyl--4-hydroxy phenyl) propane, 2,2-two (3,5-two chloro-4-hydroxy phenyls) propane, 2,2-two (3,5-two bromo-4-hydroxy phenyls) propane, 1,1-two (4-hydroxy phenyl) hexanaphthene and 1,1-two (4-hydroxy phenyl)-3,3, the 5-trimethyl-cyclohexane.
For example in the following document these and other suitable diphenol: US-PS 3 028635 is being described, US-PS 2 999 835, US-PS 3 148 172, US-PS 2 991 273, US-PS3 271 367, US-PS 4 982 014, US-PS 2 999 846, Germany's prospectus 1 570 703,2 063 050,2 036 052,2 211 956 and 3 832 396, French Patent specification sheets 1 561 518, the monograph of H.Schnell " polycarbonate chemistry and physics " (inner Science Press, New York 1964) and day present disclosure specification 62039/1986,62040/1986 and 105550/1986.
Under the homo-polycarbonate situation, only use a kind of diphenol, and under the Copolycarbonate situation, use multiple diphenol.
Suitable carbonic acid derivatives is for example phosgene or diphenyl carbonate.
Be used for that of the present invention to contain iodine and/or bromated polycarbonate and also have the suitable chain terminator of other polycarbonate and/or Copolycarbonate be single phenol and monocarboxylic acid.Suitable single phenol is phenol self, alkylphenol such as cresols, p-tert-butylphenol, align octyl phenol, to isooctylphenol, align nonyl phenol and to different nonyl phenol, halogenated phenol such as P-Chlorophenol, 2,4-two chlorophenols, to bromine phenol and 2,4, the 6-bromophenisic acid especially also has 2,4,6-triiodo phenol, p-iodophenol, and their mixture.
A kind of preferred chain terminator is a p-tert-butylphenol.
Suitable monocarboxylic acid is phenylformic acid, alkylbenzoic acid and halogenated benzoic acid.
Preferred chain terminator is the phenol of formula (I)
Figure A9981450000081
Wherein R is the C of hydrogen, the tertiary butyl, side chain or non-side chain 8-and/or C 9-alkyl.
The consumption of chain terminator is the mole number 0.1mo1% to 5mol% based on used diphenol under every kind of situation.Can before the phosgenation, during or add chain terminator afterwards.
Suitable branching agent is the known trifunctional of polycarbonate chemistry or the compound of high functionality more, and particularly those contain the compound of three or more phenolic hydroxyl group groups.
Suitable branching agent is a Phloroglucinol for example, 4,6-dimethyl-2,4,6-three (hydroxy phenyl) heptene-2,4,6-dimethyl-2,4,6-three (hydroxy phenyl) heptane, 1,3,5-three (4-hydroxy phenyl) benzene, 1,1,1-three (4-hydroxy phenyl) ethane, three (4-hydroxy phenyl) phenylmethane, 2,2-two [4,4-two (4-hydroxy phenyl) cyclohexyl] propane, 2,4-two (4-hydroxy phenyl sec.-propyl) phenol, 2,6-two (2-hydroxyl-5 '-methyl-benzyl)-4-cresols, 2-(4-hydroxy phenyl)-2-(2, the 4-dihydroxy phenyl) propane, six (4-(4-hydroxy phenyl sec.-propyl) phenyl) adjacency pair phthalic acid ester, four (4-hydroxy phenyl) methane, four (4-(4-hydroxy phenyl sec.-propyl) phenoxy group) methane and 1,4-two-((4 ', 4 "-the dihydroxyl triphenyl) methyl) benzene and 2,4-resorcylic acid; trimesic acid; cyanuric acid chlorine and 3; 3-two-(3-methyl-4-hydroxy phenyl)-2-oxo-2,3-indoline.
The amount of the optional branching agent that uses is 0.05 to 2mol% with respect to the mole number of diphenol used under every kind of situation.
Branching agent can be mixed in buck with diphenol and chain terminator, or be dissolved in the organic solvent and before the phosgene effect, adding.In the transesterification method, branching agent and diphenol are added together.
All these technological processs of producing thermoplastic poly carbonic ether are known for a person skilled in the art.
Other polycarbonate and/or Copolycarbonate can with relative moulded parts 0 to 99.9wt%, preferred 70 to 99wt%, preferred especially 80 to 98wt% and very particularly preferably 90 to 98wt% amount exist.
In order to obtain improved composition, also can add in addition at least a other be present in thermoplastic materials usually, additive in optimization polycarbonate and the Copolycarbonate, stablizer (described) for example as EP 0 839 623 A1 or EP 0 500 496 A1, thermo-stabilizer particularly, especially organic phosphite (or ester or phosphine), releasing agent is as wherein unsaturated fatty acids can be all or part of by epoxidised glycerol fatty acid ester or tetramethylol methane, particularly glycerine monostearate or pentaerythritol tetrastearate (PETS), fire retardant, static inhibitor, UV-absorption agent such as triazole, filler, whipping agent, dyestuff, pigment, white dyes and nucleator or the like, preferably the relative amount of the mixture of its consumption separately mostly is most 5wt%, preferred 0.01 to 5wt% is 0.01 to 1wt% with the amount of preferred especially relative plastic material.
The mixture of these additives also is fine.
In addition, under the situation of the mixture that contains multiple thermoplastic materials, in order to reach component compatibility and higher transparency preferably, also can randomly use known transesterification catalyst such as organotin or titanium compound in the document, disclosed in its consumption such as the document, preferable amount is 10 to 1000ppm.
Use the UV-stablizer of triazole series can obtain good especially performance.The example that this paper mentions especially is 2-(3 ', 5-two-(1, the 1-dimethyl benzyl)-2 '-hydroxy phenyl) benzotriazole, 2-(2 '-hydroxyl-5 '-(uncle's octyl group) phenyl) benzotriazole, 2-(2 '-hydroxyl-3 '-(2-butyl)-5 '-(uncle's octyl group) phenyl) benzotriazole, two (3-(2H-benzotriazole base)-2-hydroxyl-uncle's 5-octyl group) methane, 2-(4-hexyloxy-2 hydroxy phenyl)-4,6-biphenyl-1,3,5-triazine and benzophenone such as 2,4 dihydroxy benzophenone.
Surprisingly, (as usually for the situation of for example toy and medical equipment) also do not add the UV absorption agent up to now in household application.
Can be with method such as impact molding, the spinning method of routine, extrude or jet molding is converted into formed article with the opaque polymer composition of the X ray of above-mentioned acquisition, as toy for children, but also can be processed into fiber, film, band, sheet material, sheet material, container, pipe and other section bar with ribbing.Also polymer composition can be processed into casting film.Therefore, the present invention also relates to the purposes of polymer composition of the present invention in producing moulded products.The purposes of multilayer system also is interesting.Therefore, the polymer composition that contains the brominated of high level or contain iodine additives of the present invention is applied to the transparent forming polymer goods of X-ray with thin layer form.Just carry out when this is applied in basic goods for example by coextrusion or the moulding of multi-material injection molding method or after the moulding.Yet thin layer also can be applied to the basic goods of final molding, for example by film laminating or use solution coating.Moulding compound of the present invention is particularly suitable for transparent toy for children or medical.Such moulded parts is suitable for the little goods in the toy for children most.
Embodiment Embodiment 1-4
(Makrolon 2808 with 92.5 parts of (weight) polycarbonate and dihydroxyphenyl propane Bayer AG) and 5-20 part (weight) big lake chemical company (Great Lakes ChemicalCorp., Lafayette, IN, USA) the tetrabromobisphenol oligo-ester carbonate (TBBOC) of Sheng Chaning arises from compounding in Bitruder under 280 ℃, then it is squeezed into the experiment slice of different thickness.
The embodiment sequence number ????1 ????2 ????3 ????4
TBBOC content ????5wt.％ ????7.5wt.％ ????10wt.％ ????20wt.％
X-ray can detect (1.2mm) Be Be Be Be
The transparency Transparent Transparent Opaque a little Opaque a little
Glass transition temperature Undetermined Undetermined ????155℃ ????156℃
Extension at break ????137％ ????130％ ????130％ Undetermined
4mm thick and contain 5 or the platelet of the TBBOC of 7.5wt% be fully transparent.
The X ray contrast of these plates is excellent.Even when the thickness of these plates has only 1.2mm, in the X-ray picture, still can clearly be discerned.

Claims (9)

1. contain the purposes of polycarbonate in the moulded parts with high X ray contrast of iodine and/or bromine, it is characterized in that: they contain two phenol units and its weight-average molecular weight M of iodinating and/or bromination wBe 500 to 100000, preferred 1000 to 40000 and preferred especially 1000 to 8000.
2. the described purposes of claim 1 is characterized in that: iodine in the moulded parts and/or bromine content are 0.2 to 70wt%, preferred 1 to 25wt% and preferred especially 2 to 15wt%.
3. at least one described purposes of aforementioned claim, it is characterized in that: moulded parts also contains at least a transparent thermoplastic material, preferred non-halogenated polycarbonate or Copolycarbonate, its relatively the amount of this moulded parts be 70 to 99wt%, preferred 80 to 98wt% and preferred especially 90 to 98wt%.
4. at least one described purposes of aforementioned claim, it is characterized in that: composition also contain at least a other be present in additive in polycarbonate and the Copolycarbonate usually, stablizer for example, thermo-stabilizer particularly, especially organic phosphite or ester or phosphine, releasing agent is as wherein unsaturated fatty acids can be all or part of by the fatty acid ester of epoxidised glycerine or tetramethylol methane, particularly glycerine monostearate or pentaerythritol tetrastearate (PETS), fire retardant, static inhibitor, UV-absorption agent such as triazole, filler, whipping agent, dyestuff, pigment, white dyes, transesterification catalyst and nucleator or the like, the relative amount of the mixture of its each plant demand preferably mostly is most 5wt%, preferred 0.01 to 5wt% is 0.01 to 1wt% with the amount of preferred especially relative plastic material.
5. at least one described purposes of aforementioned claim is characterized in that: stablizer is the UV-stablizer, preferably from triazole series with especially preferably from benzotriazole series.
6. contain the toy of the polycarbonate of iodinating and/or bromination, it is characterized in that: they contain two phenol units and the weight-average molecular weight M of iodinating and/or bromination wBe 500 to 100000, preferred 1000 to 40000 and preferred especially 1000 to 8000, to improve the X-ray contrast.
7. contain iodinating and/or bromination polycarbonate medical equipment such as probe or the parts of movable joint are arranged, it is characterized in that: they contain two phenol units and the weight-average molecular weight M of iodinating and/or bromination wBe 500 to 100000, preferred 1000 to 40000 and preferred especially 1000 to 8000, to improve the X-ray contrast.
8. contain the transparent thermoplastic material's of iodinating and/or bromination toy, it is characterized in that: they contain the monomeric unit and the weight-average molecular weight M of at least a iodinating and/or bromination wBe 500 to 1000000 and preferred 10000 to 40000, to improve the X-ray contrast.
9. contain iodinating and/or bromination the transparent thermoplastic material medical equipment such as probe or the parts of movable joint are arranged, it is characterized in that: they contain the monomeric unit and the weight-average molecular weight M of at least a iodinating and/or bromination wBe 500 to 1000000 and preferred 10000 to 40000, to improve the X-ray contrast.
CN99814500A 1998-12-18 1999-12-07 Use of polycarbonates containing iodine and/or bromine for moulded parts with high x-ray contrast and moulded parts produced with same Pending CN1330688A (en)

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CN107108863A (en) * 2014-12-23 2017-08-29 新泽西鲁特格斯州立大学 The iodate diphenol monomer and polymer of biocompatibility

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JP2005325319A (en) * 2004-04-15 2005-11-24 Teijin Chem Ltd Polycarbonate resin composition
CN101014642B (en) * 2004-08-13 2010-04-21 雷瓦医药公司 Inherently radiopaque bioresorbable polymers for multiple uses
JP5347244B2 (en) * 2006-08-04 2013-11-20 三菱化学株式会社 Method for producing halogen-containing polycarbonate resin
WO2020173665A1 (en) 2019-02-28 2020-09-03 Speed Care Mineral Gmbh Paste for marking textile fabrics and/or other products incapable of x-ray contrast

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US4182787A (en) * 1978-06-19 1980-01-08 General Electric Company Optically transparent, radiographically opaque tubing
EP0359366B1 (en) * 1988-09-06 1994-03-09 Mitsubishi Kasei Corporation Medical moldings and method for their preparation
JPH0641416A (en) * 1992-07-24 1994-02-15 Nippon Steel Chem Co Ltd Flame-retardant polycarbonate resin composition and molded object thereof
DE4229642A1 (en) * 1992-09-04 1994-03-10 Bayer Ag Powder mixtures for matt polycarbonate molding compounds
JPH0857033A (en) * 1994-08-25 1996-03-05 Terumo Corp X-ray contrasting medical molding
DE19726191A1 (en) * 1997-06-20 1998-12-24 Bayer Ag Use of iodophenyl carbonate-containing polycarbonates for the production of special molded parts

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107108863A (en) * 2014-12-23 2017-08-29 新泽西鲁特格斯州立大学 The iodate diphenol monomer and polymer of biocompatibility
CN107108863B (en) * 2014-12-23 2021-03-19 新泽西鲁特格斯州立大学 Biocompatible diphenoliodide monomers and polymers

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