AU2014278745B2 - Polymer compositions with enhanced radiopacity - Google Patents
Polymer compositions with enhanced radiopacity Download PDFInfo
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- AU2014278745B2 AU2014278745B2 AU2014278745A AU2014278745A AU2014278745B2 AU 2014278745 B2 AU2014278745 B2 AU 2014278745B2 AU 2014278745 A AU2014278745 A AU 2014278745A AU 2014278745 A AU2014278745 A AU 2014278745A AU 2014278745 B2 AU2014278745 B2 AU 2014278745B2
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- 229920000642 polymer Polymers 0.000 title claims abstract description 178
- 239000000203 mixture Substances 0.000 title claims abstract description 165
- 239000000178 monomer Substances 0.000 claims abstract description 209
- 238000000034 method Methods 0.000 claims abstract description 30
- 229920006037 cross link polymer Polymers 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 239000003153 chemical reaction reagent Substances 0.000 claims description 50
- 239000002243 precursor Substances 0.000 claims description 35
- 125000002947 alkylene group Chemical group 0.000 claims description 27
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 230000008859 change Effects 0.000 claims description 24
- 230000009477 glass transition Effects 0.000 claims description 24
- 229910052740 iodine Inorganic materials 0.000 claims description 23
- 229910052797 bismuth Inorganic materials 0.000 claims description 22
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- 125000004450 alkenylene group Chemical group 0.000 claims description 19
- 125000004419 alkynylene group Chemical group 0.000 claims description 19
- 125000000732 arylene group Chemical group 0.000 claims description 19
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 19
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 19
- 125000005549 heteroarylene group Chemical group 0.000 claims description 19
- 230000001225 therapeutic effect Effects 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 17
- 239000003999 initiator Substances 0.000 claims description 17
- 238000003860 storage Methods 0.000 claims description 16
- 230000006870 function Effects 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229920000515 polycarbonate Polymers 0.000 claims description 12
- 239000004417 polycarbonate Substances 0.000 claims description 12
- 229920002635 polyurethane Polymers 0.000 claims description 11
- 239000004814 polyurethane Substances 0.000 claims description 11
- 239000012530 fluid Substances 0.000 claims description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- 210000003484 anatomy Anatomy 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
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- 210000000056 organ Anatomy 0.000 claims description 5
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
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- 230000001079 digestive effect Effects 0.000 claims description 3
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- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 239000004971 Cross linker Substances 0.000 abstract description 113
- 229920000431 shape-memory polymer Polymers 0.000 description 59
- 150000001875 compounds Chemical class 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 31
- 238000006116 polymerization reaction Methods 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- 238000011084 recovery Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- -1 poly(epsilon- caprolactone) Polymers 0.000 description 21
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 20
- 239000011630 iodine Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 125000004429 atom Chemical group 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000004132 cross linking Methods 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 13
- 238000003384 imaging method Methods 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical group 0.000 description 12
- 230000036760 body temperature Effects 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
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- 150000003254 radicals Chemical class 0.000 description 11
- 125000006850 spacer group Chemical group 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 125000004386 diacrylate group Chemical group 0.000 description 9
- 230000000977 initiatory effect Effects 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000010348 incorporation Methods 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 6
- 239000012620 biological material Substances 0.000 description 6
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 6
- 230000003073 embolic effect Effects 0.000 description 6
- 238000002594 fluoroscopy Methods 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 238000002595 magnetic resonance imaging Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
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- 230000001960 triggered effect Effects 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 206010002329 Aneurysm Diseases 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
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- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 4
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- 239000012044 organic layer Substances 0.000 description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
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- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 125000006834 (C4-C20) alkylene group Chemical group 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
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- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 229910052697 platinum Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 2
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
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- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
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- 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
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/04—Macromolecular materials
- A61L29/041—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
- A61L29/18—Materials at least partially X-ray or laser opaque
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- A—HUMAN NECESSITIES
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/048—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/18—Materials at least partially X-ray or laser opaque
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/303—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one or more carboxylic moieties in the chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/16—Materials with shape-memory or superelastic properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/105—Esters of polyhydric alcohols or polyhydric phenols of pentaalcohols
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Vascular Medicine (AREA)
- Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Materials For Medical Uses (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
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| US201361787345P | 2013-03-15 | 2013-03-15 | |
| US61/787,345 | 2013-03-15 | ||
| PCT/US2014/028786 WO2014200594A1 (en) | 2013-03-15 | 2014-03-14 | Polymer compositions with enhanced radiopacity |
Publications (2)
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| AU2014278745A1 AU2014278745A1 (en) | 2015-09-17 |
| AU2014278745B2 true AU2014278745B2 (en) | 2019-03-14 |
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| AU2014278745A Ceased AU2014278745B2 (en) | 2013-03-15 | 2014-03-14 | Polymer compositions with enhanced radiopacity |
Country Status (7)
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|---|---|
| US (1) | US10590218B2 (https=) |
| EP (1) | EP2968620B1 (https=) |
| JP (1) | JP6543831B2 (https=) |
| CN (1) | CN105209078B (https=) |
| AU (1) | AU2014278745B2 (https=) |
| CA (1) | CA2903060A1 (https=) |
| WO (1) | WO2014200594A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014124225A1 (en) | 2013-02-08 | 2014-08-14 | Endoshape, Inc. | Radiopaque polymers for medical devices |
| CN105209078B (zh) | 2013-03-15 | 2021-11-09 | 恩多沙普公司 | 具有增强的不透射线性的聚合物组合物 |
| WO2018053314A1 (en) | 2016-09-16 | 2018-03-22 | Greg Mirigian | Occlusive implants with fiber-based release structures |
| AU2017366683A1 (en) * | 2016-12-02 | 2019-05-23 | Endoshape, Inc. | Radiopaque polymers with enhanced radiopacity |
| US11597792B2 (en) * | 2017-10-30 | 2023-03-07 | The Texas A&M University System | Radiopaque thermoplastic polymer |
| CN113286549A (zh) | 2019-06-05 | 2021-08-20 | 恩多沙普公司 | 用于改进的阻塞和递送的系统、装置和方法 |
| EP4025616A4 (en) * | 2019-09-12 | 2023-11-08 | Endoshape, Inc. | X-RAY DENSITY POLYMERS FOR MEDICAL DEVICES |
| EP4041319A1 (fr) * | 2019-10-07 | 2022-08-17 | Guerbet | Microsphere d'embolisation non degradable radio-opaque |
| KR102202101B1 (ko) * | 2019-11-28 | 2021-01-14 | 주식회사 신아티앤씨 | 다관능 아크릴레이트 화합물, 이를 포함하는 양자점층 형성용 조성물 및 광학 필름 |
| CN121237997A (zh) * | 2025-07-02 | 2025-12-30 | 深圳市贝特瑞新能源技术研究院有限公司 | 固态电解质、其制备方法、锂离子电池和涉电设备 |
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-
2014
- 2014-03-14 CN CN201480027781.1A patent/CN105209078B/zh not_active Expired - Fee Related
- 2014-03-14 CA CA2903060A patent/CA2903060A1/en not_active Abandoned
- 2014-03-14 US US14/776,875 patent/US10590218B2/en active Active - Reinstated
- 2014-03-14 AU AU2014278745A patent/AU2014278745B2/en not_active Ceased
- 2014-03-14 EP EP14811002.6A patent/EP2968620B1/en not_active Not-in-force
- 2014-03-14 JP JP2016502897A patent/JP6543831B2/ja not_active Expired - Fee Related
- 2014-03-14 WO PCT/US2014/028786 patent/WO2014200594A1/en not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4644025A (en) * | 1984-06-20 | 1987-02-17 | Kureha Kagaku Kogyo Kabushiki Kaisha | Lens materials of high refractive indexes |
| US5780668A (en) * | 1994-05-30 | 1998-07-14 | Ivoclar Ag | X-ray opaque dental materials |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2014278745A1 (en) | 2015-09-17 |
| CA2903060A1 (en) | 2014-12-18 |
| JP2016513750A (ja) | 2016-05-16 |
| EP2968620B1 (en) | 2019-02-13 |
| US10590218B2 (en) | 2020-03-17 |
| CN105209078B (zh) | 2021-11-09 |
| EP2968620A4 (en) | 2016-10-05 |
| US20160024239A1 (en) | 2016-01-28 |
| WO2014200594A1 (en) | 2014-12-18 |
| JP6543831B2 (ja) | 2019-07-17 |
| CN105209078A (zh) | 2015-12-30 |
| EP2968620A1 (en) | 2016-01-20 |
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| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |