DE102004040923A1 - Spezielle Calixarene, Verfahren zu ihrer Herstellung und ihre Verwendung - Google Patents
Spezielle Calixarene, Verfahren zu ihrer Herstellung und ihre Verwendung Download PDFInfo
- Publication number
- DE102004040923A1 DE102004040923A1 DE102004040923A DE102004040923A DE102004040923A1 DE 102004040923 A1 DE102004040923 A1 DE 102004040923A1 DE 102004040923 A DE102004040923 A DE 102004040923A DE 102004040923 A DE102004040923 A DE 102004040923A DE 102004040923 A1 DE102004040923 A1 DE 102004040923A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- calix
- calixarenes
- octyl
- und
- 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.)
- Withdrawn
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- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical class COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 11
- 230000008569 process Effects 0.000 title claims description 7
- 150000002500 ions Chemical class 0.000 claims abstract description 20
- 239000003513 alkali Substances 0.000 claims abstract description 17
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 16
- 241001120493 Arene Species 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 26
- -1 tert-octyl Chemical group 0.000 claims description 19
- 238000000605 extraction Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- GQPLZGRPYWLBPW-UHFFFAOYSA-N calix[4]arene Chemical compound C1C(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC2=CC=CC1=C2 GQPLZGRPYWLBPW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000001179 sorption measurement Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000003463 adsorbent Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000010626 work up procedure Methods 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 238000000926 separation method Methods 0.000 description 15
- 241000854711 Shinkai Species 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 150000003983 crown ethers Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000012491 analyte Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 229910003460 diamond Inorganic materials 0.000 description 3
- 239000010432 diamond Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 238000000622 liquid--liquid extraction Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- XSXWOBXNYNULJG-UHFFFAOYSA-N 2-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1O XSXWOBXNYNULJG-UHFFFAOYSA-N 0.000 description 2
- YEKPNMQQSPHKBP-UHFFFAOYSA-N 2-methyl-6-nitrobenzoic anhydride Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C(=O)OC(=O)C1=C(C)C=CC=C1[N+]([O-])=O YEKPNMQQSPHKBP-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000002555 ionophore Substances 0.000 description 2
- 230000000236 ionophoric effect Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 206010022528 Interactions Diseases 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004094 preconcentration Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000012982 x-ray structure analysis Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
- C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
- C22B3/26—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds
- C22B3/302—Ethers or epoxides
- C22B3/304—Crown ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/92—Systems containing at least three condensed rings with a condensed ring system consisting of at least two mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic system, e.g. cyclophanes
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B26/00—Obtaining alkali, alkaline earth metals or magnesium
- C22B26/10—Obtaining alkali metals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Geology (AREA)
- Geochemistry & Mineralogy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Environmental & Geological Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004040923A DE102004040923A1 (de) | 2004-08-24 | 2004-08-24 | Spezielle Calixarene, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US11/574,144 US7393969B2 (en) | 2004-08-24 | 2005-08-16 | Particular calixarenes method for production and use thereof |
| PCT/EP2005/008865 WO2006021342A1 (de) | 2004-08-24 | 2005-08-16 | Spezielle calixarene, verfahren zu ihrer herstellung und ihre verwendung |
| AU2005276650A AU2005276650B2 (en) | 2004-08-24 | 2005-08-16 | Particular calixarenes method for production and use therof |
| JP2007528689A JP4906726B2 (ja) | 2004-08-24 | 2005-08-16 | 特定のカリックスアレーン、その製造方法およびその使用 |
| AT05777554T ATE498602T1 (de) | 2004-08-24 | 2005-08-16 | Spezielle calixarene und ihre verwendung |
| CN2005800362711A CN101044110B (zh) | 2004-08-24 | 2005-08-16 | 特定杯芳烃及其制备方法和用途 |
| CA002577864A CA2577864A1 (en) | 2004-08-24 | 2005-08-16 | Particular calixarenes, method for production and use therof |
| EP05777554A EP1786757B1 (de) | 2004-08-24 | 2005-08-16 | Spezielle calixarene und ihre verwendung |
| DE502005010978T DE502005010978D1 (de) | 2004-08-24 | 2005-08-16 | Spezielle calixarene und ihre verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004040923A DE102004040923A1 (de) | 2004-08-24 | 2004-08-24 | Spezielle Calixarene, Verfahren zu ihrer Herstellung und ihre Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102004040923A1 true DE102004040923A1 (de) | 2006-03-02 |
Family
ID=35583392
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102004040923A Withdrawn DE102004040923A1 (de) | 2004-08-24 | 2004-08-24 | Spezielle Calixarene, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE502005010978T Expired - Lifetime DE502005010978D1 (de) | 2004-08-24 | 2005-08-16 | Spezielle calixarene und ihre verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502005010978T Expired - Lifetime DE502005010978D1 (de) | 2004-08-24 | 2005-08-16 | Spezielle calixarene und ihre verwendung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7393969B2 (enExample) |
| EP (1) | EP1786757B1 (enExample) |
| JP (1) | JP4906726B2 (enExample) |
| CN (1) | CN101044110B (enExample) |
| AT (1) | ATE498602T1 (enExample) |
| AU (1) | AU2005276650B2 (enExample) |
| CA (1) | CA2577864A1 (enExample) |
| DE (2) | DE102004040923A1 (enExample) |
| WO (1) | WO2006021342A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5248132B2 (ja) * | 2008-02-08 | 2013-07-31 | スガイ化学工業株式会社 | カリックスアレン誘導体の製造方法 |
| CN102127233A (zh) * | 2010-11-11 | 2011-07-20 | 天津工业大学 | 一种具有杯芳烃衍生物结构的高分子材料制备方法 |
| CN102880001B (zh) * | 2012-09-11 | 2013-12-25 | 中国科学院上海光学精密机械研究所 | 激光热刻蚀有机光刻胶及其制备方法 |
| CN102911071B (zh) * | 2012-09-29 | 2015-02-25 | 上海大学 | 氨基酸与水溶性柱[5]芳烃超分子配合物及其制备方法 |
| FR3031738B1 (fr) * | 2015-01-19 | 2018-10-05 | Adionics | Dispositif et methode de dessalement d'eau par deionisation thermique et liquide d'extraction ionique liquide applicable audit dispositif |
| WO2016156941A1 (en) * | 2015-04-03 | 2016-10-06 | Diasys Diagnostics India Private Limited | Solid state electrolyte biosensor |
| CN106244826B (zh) * | 2016-07-25 | 2018-06-29 | 浙江大学 | 一种从盐湖水中同时分离钾铷铯的方法 |
| CN110180504A (zh) * | 2019-06-04 | 2019-08-30 | 东华理工大学 | 一种碳基非对称双冠超分子杂化材料及其制备方法和应用 |
| CN111073467B (zh) * | 2019-12-20 | 2021-08-06 | 浙江中杭新材料科技有限公司 | 一种用于钕铁硼的耐腐蚀复合防护层材料 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4912183A (en) * | 1984-01-30 | 1990-03-27 | Loctite (Ireland) Ltd. | Polymerization catalysts and polymerization process using such catalysts |
| US4695615A (en) * | 1984-11-21 | 1987-09-22 | Loctite (Ireland) Limited | Instant adhesive composition utilizing mixed functionality calixarenes as accelerators |
| US4556700A (en) * | 1984-01-30 | 1985-12-03 | Loctite Limited | Instant adhesive composition utilizing calixarene accelerators |
| US4882449A (en) * | 1986-03-07 | 1989-11-21 | Loctite Corporation | Calixarene derivatives, and use of such compounds for sequestration of metals |
| US5132345A (en) * | 1990-12-10 | 1992-07-21 | Harris Stephen J | Ion-selective electrodes |
| JP2889424B2 (ja) * | 1992-01-19 | 1999-05-10 | 科学技術振興事業団 | イオン選択性カリックスアレーン誘導体 |
| AU2384797A (en) * | 1996-04-18 | 1997-11-12 | Novartis Ag | Fluoroionophores and their use in optical ion sensors |
| WO1998049251A1 (en) * | 1997-04-25 | 1998-11-05 | Akzo Nobel N.V. | Multiple rare-earth metal complexes |
| NL1010549C2 (nl) * | 1998-11-13 | 2000-05-16 | Priva Hortimation B V | Systeem en werkwijze voor het verwijderen van ionen uit waterige vloeistofstromen. |
-
2004
- 2004-08-24 DE DE102004040923A patent/DE102004040923A1/de not_active Withdrawn
-
2005
- 2005-08-16 AU AU2005276650A patent/AU2005276650B2/en not_active Ceased
- 2005-08-16 CN CN2005800362711A patent/CN101044110B/zh not_active Expired - Fee Related
- 2005-08-16 EP EP05777554A patent/EP1786757B1/de not_active Expired - Lifetime
- 2005-08-16 DE DE502005010978T patent/DE502005010978D1/de not_active Expired - Lifetime
- 2005-08-16 CA CA002577864A patent/CA2577864A1/en not_active Abandoned
- 2005-08-16 JP JP2007528689A patent/JP4906726B2/ja not_active Expired - Fee Related
- 2005-08-16 WO PCT/EP2005/008865 patent/WO2006021342A1/de not_active Ceased
- 2005-08-16 US US11/574,144 patent/US7393969B2/en not_active Expired - Fee Related
- 2005-08-16 AT AT05777554T patent/ATE498602T1/de active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008510749A (ja) | 2008-04-10 |
| WO2006021342A1 (de) | 2006-03-02 |
| CN101044110B (zh) | 2011-08-17 |
| ATE498602T1 (de) | 2011-03-15 |
| US7393969B2 (en) | 2008-07-01 |
| EP1786757B1 (de) | 2011-02-16 |
| AU2005276650B2 (en) | 2011-08-04 |
| JP4906726B2 (ja) | 2012-03-28 |
| CA2577864A1 (en) | 2006-03-02 |
| AU2005276650A1 (en) | 2006-03-02 |
| CN101044110A (zh) | 2007-09-26 |
| DE502005010978D1 (de) | 2011-03-31 |
| EP1786757A1 (de) | 2007-05-23 |
| US20070232826A1 (en) | 2007-10-04 |
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