CN1371405A - Radio-opaque molded plastic parts - Google Patents
Radio-opaque molded plastic parts Download PDFInfo
- Publication number
- CN1371405A CN1371405A CN00812092A CN00812092A CN1371405A CN 1371405 A CN1371405 A CN 1371405A CN 00812092 A CN00812092 A CN 00812092A CN 00812092 A CN00812092 A CN 00812092A CN 1371405 A CN1371405 A CN 1371405A
- Authority
- CN
- China
- Prior art keywords
- iodo
- plastics
- benzoic acid
- acid derivative
- polycarbonate
- 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.)
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- 239000002991 molded plastic Substances 0.000 title abstract 3
- 229920003023 plastic Polymers 0.000 claims abstract description 37
- 239000004033 plastic Substances 0.000 claims abstract description 35
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- 229920000515 polycarbonate Polymers 0.000 claims description 37
- 239000004417 polycarbonate Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 15
- 238000000465 moulding Methods 0.000 claims description 15
- 239000002131 composite material Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 229940039231 contrast media Drugs 0.000 claims description 6
- 239000002872 contrast media Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 5
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- 230000000052 comparative effect Effects 0.000 description 16
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- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
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
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- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (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
The invention relates to the use of derivatives of the iodobenzoic acid for producing radio-opaque molded parts and to plastic materials, molded plastic materials and molded plastic bodies that contain at least one ester of the iodobenzoic acid.
Description
The application relates to the iodo-benzoic acid derivative making the application of X-ray in can correlated plastics moulded body, also relates to the plastics, plastic composition and the plastics moulded body that contain at least a iodo-benzoic acid derivative.
For medical field and toy for children, seeking the transparent plastics molding that has good mechanical properties and can in X-ray examination, be detected in vivo.For the use at interior of building, such material should also have enough stability to light at least.
The commercially available molding based on polycarbonate is not suitable for above-mentioned purpose, because their contrast gradients in the X ray video are too low.Therefore the once paid X-ray contrast media that contains barium or bismuth on probation replaces polycarbonate.Yet, because toxicological reason, and the machinery of commercial polymer and the effect of optical property because they change, this contrast media is not fit to completely.
In moulding compound and molding, use as what describe among US-3 469 704, DE-A-17 20812, GB-A-11 63 816, US-3 382 207 and the US-3 535 300 and contain iodine compound and can not satisfy desired performance profile too as medical use and toy part.For example, have been found that such moulding compound or molding promptly become blush after only several weeks under room light, and/or has an inferior mechanical properties, and/or has an inadequate thermostability, and/or the iodine amount that contains very little, be not enough in an X-ray video, be detected.
Therefore, the purpose of this invention is to provide the X-ray contrast media that essential nature of plastics is not had disadvantageous effect.
Amazing is to have been found that the iodo-benzoic acid derivative satisfies desired demand distribution.Can only make by the molding of X-X-ray detection X with a spot of iodo-benzoic acid derivative.
Therefore, the present invention relates to of the application of iodo-benzoic acid derivative as X-ray contrast media, especially in plastics---especially for the application of transparent plastics, also relate to the plastics, plastic composition and the plastics moulded body that contain at least a iodo-benzoic acid ester.
According to iodo-benzoic acid derivative of the present invention be acid amides, alkylamide, dialkyl amide and, ester especially.Preferably from the ester and the acid amides of monohydroxy or poly-hydroxy, aliphatics or aromatic alcohol or amine preparation.
As an example and be preferably, the aliphatics alkohol and amine is the alkohol and amine that 1 to 30 carbon atom is arranged.Carbochain can be a straight or branched.Carbochain can comprise one or more alcohol or amine functional group, and alcohol or amine functional group can be arranged in any desired position of carbochain.Alcohol also can be randomly by halogenation.
Preferably based on the ester of following alcohol: methyl alcohol, ethanol, the 1-propyl alcohol, the 2-propyl alcohol, the 1-butanols, the 2-butanols, the trimethyl carbinol, the 1-amylalcohol, the 2-amylalcohol, the 3-amylalcohol, 2-methyl-1-butene alcohol, 2-methyl-2-butanols, 3-methyl isophthalic acid-butanols, 3-methyl-2-butanols, 2,2-dimethyl propyl alcohol, hexanol, enanthol, octanol, nonyl alcohol, decyl alcohol, undecyl alcohol, dodecanol, tridecyl alcohol, tetradecanol, pentadecylic alcohol, cetyl alcohol, heptadecanol, Stearyl alcohol, and their structure isomeride randomly, 1,2-ethylene glycol, Pehanorm, tetramethylolmethane, 1,2-propylene glycol and 1, ammediol.
Under the situation of polyhydroxy-alcohol, mixed ester, for example partly with iodo-benzoic acid and partly with the mixed ester of another kind of acid, perhaps not fully the compound of esterification also be suitable for according to the present invention.
Aromatic alcohol is phenol and bisphenols especially.
Except that iodine, the iodo-benzoic acid derivative can also be by F, Cl or Br halogenation.A preferably not halogenated iodo-benzoic acid derivative, especially preferred 4-iodo-benzoic acid derivative.
According to the present invention, the different mixtures that contains the iodo-benzoic acid derivative also is suitable for.
Described iodo-benzoic acid derivative is known or prepares by currently known methods.
Described iodo-benzoic acid derivative preferably adds in the plastics with the amount of 0.001 to 20 weight %, preferred 1 to 6 weight %.
Used " plastics " speech should be understood that preferably to be meant thermoplastics, especially transparent thermoplastics, the preferably polycondensation product of unsaturated polymer of monomers of olefinic and/or bifunctional reactivity compound.The mixture of several plastics also is possible within the scope of the invention.
Especially the plastics of Shi Yonging are based on the polycarbonate or the Copolycarbonate of bis-phenol, polyacrylic ester or copolymer acrylate and polymethacrylate or copolymerization methacrylic ester, for example and be preferably polymethylmethacrylate, cinnamic polymkeric substance or multipolymer, for example and be preferably transparent polystyrene or polystyrene vinyl cyanide (SAN), transparent thermoplastic polyurethane, and polyolefine, for example and be preferably the transparent polypropylene type or based on the polyolefine of cyclenes (such as the TOPAS of Hoechst
), the polycondensation product or the copolycondensation product of terephthalic acid, for example and be preferably poly--or copolymerization of ethylene terephthalate (PET or CoPET) or glycol-modified PET (PETG).
Especially preferred is polycarbonate or Copolycarbonate, especially not halogenated polycarbonate and/or Copolycarbonate, its molecular weight M
WBe 600 to 100,000, be preferably 2,000 to 80,000, especially be preferably 18,000 to 40,000.
Thermoplastic aromatic polycarbonate within the scope of the present invention be homo-polycarbonate be again Copolycarbonate; These polycarbonate are straight or branched in a known way.
Described polycarbonate also can be by bromination completely or partially.
The preparation of described polycarbonate can be in the known manner from bis-phenol, carbonic acid derivatives, randomly chain terminator and randomly branching agent carry out.
Over about 40 years, the details of relevant preparation polycarbonate has seen in many patent specifications.Here only lifting below with reference to document is example: Schnell at " polymkeric substance comment " (PolymerReviews) " polycarbonate chemistry and physics " (IntersciencePublishers on the 9th volume, New York, London, Sydney 1964), the D.Freitag of Beyer Co., Ltd (BayerAG), U.Grigo, P.R.M ü ller and H.Nouvertne " polycarbonate " on the 648th to 718 page of " Encyclopedia of Polymer Science and Engineering " 1988 the 2nd edition the 11st volume; With last Dres.U.Grigo, K.Kirchner, with P.R.M ü ller at " Becker/Braun, Kunststoff-Handbuch " the 3/1st volume " polycarbonate, polyacetal, polyester, cellulose ester " in " polycarbonate " (Carl Hanser Verlag Munich, Vienna 1992) of the 117th to 299 page.
Bis-phenol is preferred in the polycarbonate:
4,4 '-dihydroxybiphenyl, 2,2-two (4-hydroxy phenyl) propane, 2,4-two (4-hydroxy phenyl)-2-methylbutane, 1,1-two (4-hydroxy phenyl) is to diisopropyl benzene, and 2, two (3-methyl-4-hydroxy phenyl) propane of 2-, 2, two (the 3-chloro-4-hydroxy phenyl) propane of 2--, two (3,5-dimethyl-4-hydroxy phenyl) methane, 2, two (3, the 5-dimethyl-4-hydroxy phenyl) propane of 2-, two (3,5-dimethyl-4-hydroxy phenyl) sulfone, 2,4-two (3,5-dimethyl-4-hydroxy phenyl)-and the 2-methylbutane, 1,1-two (3,5-dimethyl-4-hydroxy phenyl) to diisopropyl benzene, 2,2-two (3,5-two chloro-4-hydroxy phenyls) propane, 2,2 pairs (3,5-two bromo-4-hydroxy phenyls) propane and 1, two (the 4-hydroxy phenyls)-3,3 of 1-, the 5-trimethyl-cyclohexane.
Especially preferred bis-phenol is 2,2-two (4-hydroxy phenyl) propane, 2, two (3, the 5-dimethyl-4-hydroxy phenyl) propane, 2 of 2-, 2-two (3,5-two chloro-4-hydroxy phenyls) propane, 2,2 pairs of (3,5-two bromo-4-hydroxy phenyls) propane, 1,1-bis(4-hydroxyphenyl) cyclohexane and 1, two (the 4-hydroxy phenyls)-3,3 of 1-, the 5-trimethyl-cyclohexane.
Preferred branching agent is triphenol, trimesic acid (trichloride), tricyanic acid trichloride and 3,3-two (3-methyl-4-hydroxy phenyl)-2-oxo-2,3-indoline.
In order to obtain improved plastics composite, may and advantageously also mix routine and be present in thermoplastics, at least a other additive in optimization polycarbonate and the Copolycarbonate, for example, stablizer (for example described in EP 0 839 623 A1 or EP 0 500 496 A1), especially thermo-stabilizer, especially organic hindered phenol, hindered amine (HALS), phosphite or phosphine, for example and be preferably triphenylphosphine, releasing agent, for example and be preferably the fatty acid ester of glycerine or pentaerythritol, wherein unsaturated fatty acids also can be by epoxidation whole or in part, especially monostearin or pentaerythritol tetrastearate (PETS), fire retardant, static inhibitor, UV light absorber, for example and be preferably hydroxybenzotriazole and hydroxyl triazine, weighting agent, whipping agent, tinting material, pigment, optical whitening agent, catalyst for ester exchange reaction and nucleator etc., preferably amount separately is maximum 5 weight %, preferred 0.01 to 5 weight %, this is based on whole mixture meter, especially preferred 0.01 to 1 weight %, and this is based on the amount meter of plastics.
Mix the iodo-benzoic acid ester and randomly blast blending or additive agent mixture carry out in the mode of common routine, for example, before the polymerization among or by subsequently with the mixing of plastics, preferably by extruding.
The common form of the plastics composite that obtains like this is solution, dispersion, emulsion, dust, powder, particle, small pieces or thin slice (moulding compound), and is used to the manufacturing (molding) of moulded products.The manufacturing of plastics moulded body is undertaken by the method for routine, such as hot pressing, spinning, extrude or injection-molded.
Usually the iodine that contains the combination of 0.01 to 10 weight %, preferred 1 to 3 weight % according to plastics composite of the present invention.
Moulded products is the goods of translucidus preferably, in particular for medical, such as and preferably detector and interconnecting piece, or the also little article used of children.Yet, use according to plastics composite of the present invention and can certainly make conventional moulded products, such as film, band, sheet, wallpaper, laminated paper, container, pipe and others.Plastics composite also can processedly be cast film.
In making multilayer system, use also very useful according to plastics composite of the present invention.In this case, be applied to plastic shaping goods that do not contain X-ray contrast media according to plastics composite of the present invention by form with thin layer.This application can be carried out when making the molding moulding simultaneously, or carries out following closely, such as the mode by co-extrusion or multi-material injection system.Yet composition also can be used to the matrix of moulding at last, such as by rolling with film or passing through solution coatings.
The plastics composite that contains the iodo-benzoic acid ester is preferably applied the manufacturing with widget in children, especially such as the manufacturing of the toy of building puzzle and so on.
The following examples are used to illustrate the present invention.The present invention not only is confined to these embodiment.In the following embodiments, per-cent and umber are meant weight percent and parts by weight.
Embodiment 1
29.3 parts 4-iodobenzene formyl chloride (Aldrich) is dissolved in 100 parts of pyridines.Then 3.1 parts ethylene glycol (Aldrich) is under agitation splashed into.After 10 minutes, heated 1 hour down at 75 ℃.Then product is extracted water, bronsted lowry acids and bases bronsted lowry washing in addition, drying in methylene dichloride.The diester theoretical yield that obtains is 98.7%.The fusing point of these leucocompound is 146 ℃.
Embodiment 2
With 95.5 parts non-additive, the polycarbonate of stabilization not, its molecular-weight average is about 30,000 (according to MW of GPC), the soltion viscosity η=1.293 (Makrolon of Bayer AG 2808
), use twin screw extruders to mix with 1-two-4-iodo-benzoic acid ester (from embodiment 1) of 0.3 part PETS and 4 parts down at 300 ℃, injection-molded generates coloured print (155mm * 75mm * 2mm) then.
Embodiment 3
From the light stability of coloured print of embodiment 2 by measuring with ultraviolet lamp, Xe-WOM-lamp and sun-exposed mode.The results are shown in the table 1.
Thickness is the light stability of the sample of 2mm among table 1: the embodiment 2
Embodiment 4
| Before aging | After aging | |
| 8h ultraviolet lamp 254nm | Colourless | There is not the variation that to distinguish |
| 200?h?Xe-WOM | Colourless | There is not the redness that to distinguish |
| Two months room lights | Colourless | There is not the variation that to distinguish |
With 4 parts of ethylene glycol-two-4-iodo-benzoic acid ester (from embodiment 1) and 96 parts of polymethylmethacrylate (Plexiglas
) be dissolved in 150 parts of methylene dichloride, be processed into the film that thickness is 180 μ m, dry in a vacuum.Then film was exposed 8 hours under the 254nm ultraviolet lamp.There is not visual can observedly fading.Further, with afterwards, the visible spectrum between 400 to 1200nm is consistent in the framework of measuring accuracy before the uviolizing.
Embodiment 5
13.3 gram 4-iodobenzene formyl chlorides are dissolved in 30 milliliters the ethylene dichloride and 4 milliliters of pyridines.6.5 gram dibutylamine are dripped in the solution lentamente, at room temperature further carry out 30 minutes stirring.Reaction mixture water, 10% sodium hydroxide solution, 10% hydrochloric acid and wash with water are once more used dried over sodium sulfate, concentrate at last.Output is 18 gram pale yellow crystals.Product can melt with polycarbonate at 320 ℃, the generation of not fading.
Embodiment 6
At auxiliary Makrolon 2808 cast films that contain product 5% among the embodiment 5 of making down of methylene dichloride.Film is transparent and colourless.When film exposed 14 hours the time, there be not visual can observedly fading under 254 nm ultraviolet lamps.Comparative Examples 1
With 161.1 gram (0.11mol) oligomeric-[2,2-two (4-hydroxy phenyl) propane carbonic ether] chloro-formic ester (polymerization degree is approximately 5) is (according to U.Grigo, K.Kirchner, roll up " polycarbonate with P.R.M ü ller at " Becker/Braun, Kunststoff-Handbuch " the 3/1st, polyacetal, polyester, cellulose ester " in the 143rd page of " polycarbonate " (CarlHanser Verlag Munich, Vienna 1992) in reaction formula (3.9) preparation) be dissolved in the 1000 gram methylene dichloride.To stir at 20-25 ℃ by the clear solution that 45% sodium hydroxide solution and the 800 gram water of 89.1 gram (0.189mol) 2,35.6 grams (0.40mol) are formed and add.After 5 minutes, add the N-ethylpiperidine of 0.71 gram, mixture was by vigorous stirring 30 minutes.With methylene dichloride phase and aqueous phase separation, washing makes it not contain ionogen.Evaporating solvent, spissated solution is dry under 120 ℃ pump vacuum.
Output: 202 gram colorless solids
Analyze: phenol OH:160mg/kg, saponifiable chlorine:＜0.2mg/kg
Iodine content: about 27%
When sample was heated 5 minutes with polycarbonate in 300 ℃ crucible, not fading was observed.Comparative Examples 2
With 94.7 parts of polycarbonate (Makrolon of Bayer AG 2808
) with mixing with twin screw extruder under 280 ℃ from the oligo-ester carbonate (iodophenisic acid end group) of 5.9 weight % of Comparative Examples 1 and the releasing agent PETS (pentaerythritol tetrastearate) of 0.5 weight %, injection mould becomes the strip of all thickness then.
Under each situation, the transparency of moulding bodies all is higher than 85%.Use is for parameter conventional in the medical field, shown the detectability of X-ray in thickness is 1.2 to 3.2mm sample.
Table 2: thickness is the light stability of the sample of 2mm in the Comparative Examples 2
Comparative Examples 3
| Before aging | After aging | |
| 8h ultraviolet lamp 254nm | Colourless | The obvious redness that can distinguish |
| 200?h?Xe-WOM | Colourless | The obvious redness that can distinguish |
| Two months room lights | Colourless | The obvious redness that can distinguish |
With 94.7 parts of Makrolon 2808
With 0.3 part of PETS and 5 part 4,4 '-diiodobiphenyl (Aldrich) is mixed with twin screw extruder under 280 ℃ together, and injection mould is the strip of all thickness then.
Under each situation, the transparency of molding all is higher than 85%.
Thickness is that the sample of 2mm is at 0.35W/m
2Xe-WOM under do not water aging 1000 hours.Colourless in the past sample is the intensive redness subsequently.If such sample exposed 8 hours, also can produce the redness that obviously can debate under the 254nm ultraviolet lamp.Comparative Examples 4
With 9.87 the gram (0.067mol) oligomeric-[2,2-two (4-hydroxy phenyl) propane carbonic ether] chloro-formic ester (referring to Comparative Examples 1) be dissolved in 56 the gram methylene dichloride in.To stir at 20-25 ℃ by the clear solution that 45% sodium hydroxide solution and the 72 gram water of 2.48 gram (0.01mol) 4-iodo-benzoic acids, 1.33 grams (0.015mol) are formed and add.After 5 minutes, add the N-ethylpiperidine of 0.084 gram, with mixture vigorous stirring 30 minutes.Methylene dichloride is separated from aqueous phase, and flushing makes it not contain ionogen.Evaporating solvent, spissated solution is dry under 120 ℃ pump vacuum.
Output: 9.7 gram colorless solids
Analyze: phenol OH:0.09%, saponifiable chlorine: 3ppm, iodine content: about 4.6%
When sample was heated 5 minutes with polycarbonate in 300 ℃ crucible, not fading can be observed.Similar with Comparative Examples 2, iodine content is too low, so that can't obtain containing the iodometric polycarbonate blend that can be arrived by the X-X-ray detection X.Comparative Examples 5
Preparation is by 50 parts of Makrolon 3208,50 parts of oligopolymer and 0.5 part of solution film that Tinuvin 234 forms according to Comparative Examples 4.Film exposure under ultraviolet lamp (254nm) showed after 6 hours fades.Comparative Examples 6
With 23 parts of BPA and 17 parts of phosgene and 21 part 2,3,5-iodobenzene formyl chloride is (according to WO 9859005) reaction under the phase boundary condition, generates and contains 2,3, the oligopolymer of 5-iodobenzene formyl radical end group.When sample heats 5 minutes with polycarbonate in 300 ℃ crucible, can observe tangible redness.Comparative Examples 7
6 parts of 4-iodo-benzoic acids were heated 5 minutes with 94 parts of polycarbonate in 300 ℃ crucible.Some 4-iodo-benzoic acids are deposited on the crucible edge by distillation.Comparative Examples 8
With 4 part 3, the 5-diiodosalicylic acid heated 5 minutes with 96 parts of polycarbonate in 300 ℃ crucible.The mixture color obviously becomes redness.Comparative Examples 9
4 parts of 2,3,5 triiodobenzoic acids were heated 5 minutes with 96 parts of polycarbonate in 300 ℃ crucible.The mixture color obviously becomes redness.Comparative Examples 10
By solution coat preparation by 96 parts of Makrolon 2808 and 4 part 1, the film that 4-diiodo-tetra fluoro benzene is formed.After the drying, water white film exposed 6 hours under the 254nm ultraviolet lamp.Can offer an explanation out tangible redness subsequently.Comparative Examples 11
6 parts of Iohexol (Sigma) were heated 5 minutes with 94 parts of polycarbonate in 300 ℃ crucible.Significant decolourization takes place.
Claims (10)
1. the iodo-benzoic acid derivative is as the application of X-ray contrast media.
2. the iodo-benzoic acid derivative is used for the application of the X-ray detectability processing of plastics.
3. the plastics composite that contains at least a iodo-benzoic acid derivative.
4. the method for plastics composite of preparation as definition in the claim 3 is characterized in that, with at least a iodo-benzoic acid derivative before the plastics polymerization, during and adding afterwards.
5. contain the application of plastics composite in the production plastics moulded body of iodo-benzoic acid derivative.
6. produce method, it is characterized in that, at least a plastics composite as definition in the claim 3 is used as raw material the opaque molding of X-ray.
7. the plastics moulded body that contains at least a iodo-benzoic acid derivative.
8. based on the molding with X-ray detectability of (being total to) polycarbonate or its mixture, its amount that contains the iodo-benzoic acid derivative is 0.001 to 20 weight %.
9. by the molding of producing according to the plastics composite of claim 3.
10. according to each molding in the aforementioned claim, it contains releasing agent, thermo-stabilizer and/or UV light absorber, and its content respectively is 0.001 to 1 weight %.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19940862A DE19940862A1 (en) | 1999-08-27 | 1999-08-27 | X-ray contrasting molded plastic parts |
| DE19940862.9 | 1999-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1371405A true CN1371405A (en) | 2002-09-25 |
Family
ID=7919914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00812092A Pending CN1371405A (en) | 1999-08-27 | 2000-08-16 | Radio-opaque molded plastic parts |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1228131A1 (en) |
| JP (1) | JP2003508569A (en) |
| KR (1) | KR20020021814A (en) |
| CN (1) | CN1371405A (en) |
| AU (1) | AU7276400A (en) |
| BR (1) | BR0013546A (en) |
| CA (1) | CA2382954A1 (en) |
| DE (1) | DE19940862A1 (en) |
| HK (1) | HK1050021A1 (en) |
| IL (1) | IL147805A0 (en) |
| MX (1) | MXPA02002040A (en) |
| NO (1) | NO20020732L (en) |
| WO (1) | WO2001016225A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109715700A (en) * | 2016-09-22 | 2019-05-03 | 科思创德国股份有限公司 | With the transparent mould plastic compared with low thickness |
Families Citing this family (2)
| 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 |
| 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 |
Family Cites Families (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 |
| GB9410578D0 (en) * | 1994-05-26 | 1994-07-13 | London Hospital Med Coll | Novel (meth)acrylate monomers and denture base compositions prepared therefrom |
| DE19857149A1 (en) * | 1998-12-11 | 2000-06-15 | Bayer Ag | X-ray contrasting plastic masses |
-
1999
- 1999-08-27 DE DE19940862A patent/DE19940862A1/en not_active Withdrawn
-
2000
- 2000-08-16 IL IL14780500A patent/IL147805A0/en unknown
- 2000-08-16 WO PCT/EP2000/007983 patent/WO2001016225A1/en not_active Application Discontinuation
- 2000-08-16 CN CN00812092A patent/CN1371405A/en active Pending
- 2000-08-16 JP JP2001520776A patent/JP2003508569A/en active Pending
- 2000-08-16 AU AU72764/00A patent/AU7276400A/en not_active Abandoned
- 2000-08-16 MX MXPA02002040A patent/MXPA02002040A/en not_active Application Discontinuation
- 2000-08-16 KR KR1020027002471A patent/KR20020021814A/en not_active Application Discontinuation
- 2000-08-16 CA CA002382954A patent/CA2382954A1/en not_active Abandoned
- 2000-08-16 EP EP00960464A patent/EP1228131A1/en not_active Withdrawn
- 2000-08-16 BR BR0013546-1A patent/BR0013546A/en not_active Application Discontinuation
-
2002
- 2002-02-13 NO NO20020732A patent/NO20020732L/en unknown
-
2003
- 2003-03-19 HK HK03102028.9A patent/HK1050021A1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109715700A (en) * | 2016-09-22 | 2019-05-03 | 科思创德国股份有限公司 | With the transparent mould plastic compared with low thickness |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20020021814A (en) | 2002-03-22 |
| NO20020732D0 (en) | 2002-02-13 |
| IL147805A0 (en) | 2002-08-14 |
| BR0013546A (en) | 2002-05-14 |
| HK1050021A1 (en) | 2003-06-06 |
| JP2003508569A (en) | 2003-03-04 |
| WO2001016225A1 (en) | 2001-03-08 |
| DE19940862A1 (en) | 2001-03-01 |
| EP1228131A1 (en) | 2002-08-07 |
| MXPA02002040A (en) | 2002-10-31 |
| AU7276400A (en) | 2001-03-26 |
| CA2382954A1 (en) | 2001-03-08 |
| NO20020732L (en) | 2002-02-13 |
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