NL1004192C2 - Supramoleculair polymeer. - Google Patents

Supramoleculair polymeer. Download PDF

Info

Publication number: NL1004192C2
Authority: NL; Netherlands
Prior art keywords: bridging; polymer; bridges; added; dry
Prior art date: 1996-10-04

Application number

NL1004192A

Other languages

English (en)

Dutch (nl)

Inventor

Egbert Willem Meijer

Rintje Pieter Sijbesma

Felix Hugo Beijer

Lucas Brunsveld

Original Assignee

Dsm Nv

Priority date (The priority date 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 date listed.)

1996-10-04

Filing date

1996-10-04

Publication date

1998-04-07

1996-10-04 Application filed by Dsm Nv filed Critical Dsm Nv

1996-10-04 Priority to NL1004192A priority Critical patent/NL1004192C2/nl

1997-09-25 Priority to DE69718802T priority patent/DE69718802T2/de

1997-09-25 Priority to DK97942292T priority patent/DK0929597T3/da

1997-09-25 Priority to EP97942292A priority patent/EP0929597B1/de

1997-09-25 Priority to ES97942292T priority patent/ES2191853T3/es

1997-09-25 Priority to PCT/NL1997/000535 priority patent/WO1998014504A1/en

1997-09-25 Priority to AT97942292T priority patent/ATE231891T1/de

1997-09-25 Priority to AU44018/97A priority patent/AU4401897A/en

1998-04-07 Application granted granted Critical

1998-04-07 Publication of NL1004192C2 publication Critical patent/NL1004192C2/nl

1999-04-05 Priority to US09/285,781 priority patent/US6320018B1/en

Links

229920002677 supramolecular polymer Polymers 0.000 title claims abstract description 22
229920000642 polymer Polymers 0.000 claims abstract description 35
239000000178 monomer Substances 0.000 claims description 12
239000000370 acceptor Substances 0.000 claims description 11
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
238000005859 coupling reaction Methods 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
238000000034 method Methods 0.000 claims description 2
238000011835 investigation Methods 0.000 claims 2
239000013589 supplement Substances 0.000 claims 2
210000004013 groin Anatomy 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
238000005481 NMR spectroscopy Methods 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
238000010992 reflux Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 11
239000012299 nitrogen atmosphere Substances 0.000 description 11
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
125000001118 alkylidene group Chemical group 0.000 description 7
150000001450 anions Chemical class 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
150000002085 enols Chemical group 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
QIYYJBGCJGEQLN-UHFFFAOYSA-N 2-amino-6-tridecyl-1h-pyrimidin-4-one Chemical compound CCCCCCCCCCCCCC1=CC(=O)N=C(N)N1 QIYYJBGCJGEQLN-UHFFFAOYSA-N 0.000 description 4
STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
230000020176 deacylation Effects 0.000 description 4
238000005947 deacylation reaction Methods 0.000 description 4
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 4
PXZGIZYCPLIFIX-UHFFFAOYSA-N ethyl 3-oxohexadecanoate Chemical compound CCCCCCCCCCCCCC(=O)CC(=O)OCC PXZGIZYCPLIFIX-UHFFFAOYSA-N 0.000 description 4
125000000468 ketone group Chemical group 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
KXYGHDWFGFZJPJ-UHFFFAOYSA-N 2-amino-6-phenyl-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C=C1C1=CC=CC=C1 KXYGHDWFGFZJPJ-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
229930194542 Keto Natural products 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
229910001873 dinitrogen Inorganic materials 0.000 description 3
239000003480 eluent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
230000000269 nucleophilic effect Effects 0.000 description 3
239000012071 phase Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical compound NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000004821 distillation Methods 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
-1 siloxane chains Chemical group 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
238000000859 sublimation Methods 0.000 description 2
230000008022 sublimation Effects 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
XUMIQAOMRDRPMD-UHFFFAOYSA-N (6-oxo-1h-pyrimidin-2-yl)urea Chemical compound NC(=O)NC1=NC(=O)C=CN1 XUMIQAOMRDRPMD-UHFFFAOYSA-N 0.000 description 1
RBZMSGOBSOCYHR-UHFFFAOYSA-N 1,4-bis(bromomethyl)benzene Chemical group BrCC1=CC=C(CBr)C=C1 RBZMSGOBSOCYHR-UHFFFAOYSA-N 0.000 description 1
VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
REKFEEJLXFSDJC-UHFFFAOYSA-N 1-butyl-3-(4-oxo-6-phenyl-1h-pyrimidin-2-yl)urea Chemical compound N1C(NC(=O)NCCCC)=NC(=O)C=C1C1=CC=CC=C1 REKFEEJLXFSDJC-UHFFFAOYSA-N 0.000 description 1
GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 1
BQXIGUOTPSBEJD-UHFFFAOYSA-N 2-(tridecylamino)-1h-pyrimidin-6-one Chemical compound CCCCCCCCCCCCCNC1=NC=CC(=O)N1 BQXIGUOTPSBEJD-UHFFFAOYSA-N 0.000 description 1
KWXIPEYKZKIAKR-UHFFFAOYSA-N 2-amino-4-hydroxy-6-methylpyrimidine Chemical compound CC1=CC(O)=NC(N)=N1 KWXIPEYKZKIAKR-UHFFFAOYSA-N 0.000 description 1
KOMJJSHAGGNBCM-UHFFFAOYSA-N 2-amino-6-but-3-enyl-1h-pyrimidin-4-one Chemical compound NC1=NC(=O)C=C(CCC=C)N1 KOMJJSHAGGNBCM-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical compound N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 description 1
PHMHDRYYFAYWEG-UHFFFAOYSA-N Rhapontigenin Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(O)=CC(O)=C1 PHMHDRYYFAYWEG-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
YTEISYFNYGDBRV-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)C YTEISYFNYGDBRV-UHFFFAOYSA-N 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
BKXPKNYXXNYCBX-UHFFFAOYSA-N ethyl 3-oxohept-6-enoate Chemical compound CCOC(=O)CC(=O)CCC=C BKXPKNYXXNYCBX-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
230000010287 polarization Effects 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/54—Nitrogen-containing linkages
- 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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Immobilizing And Processing Of Enzymes And Microorganisms (AREA)

NL1004192A 1996-10-04 1996-10-04 Supramoleculair polymeer. NL1004192C2 (nl)

Priority Applications (9)

Application Number	Priority Date	Filing Date	Title
NL1004192A NL1004192C2 (nl)	1996-10-04	1996-10-04	Supramoleculair polymeer.
DE69718802T DE69718802T2 (de)	1996-10-04	1997-09-25	Supramolekular polymere
DK97942292T DK0929597T3 (da)	1996-10-04	1997-09-25	Supramolekylær polymer
EP97942292A EP0929597B1 (de)	1996-10-04	1997-09-25	Supramolekular polymere
ES97942292T ES2191853T3 (es)	1996-10-04	1997-09-25	Polimero supramolecular.
PCT/NL1997/000535 WO1998014504A1 (en)	1996-10-04	1997-09-25	Supramolecular polymer
AT97942292T ATE231891T1 (de)	1996-10-04	1997-09-25	Supramolekular polymere
AU44018/97A AU4401897A (en)	1996-10-04	1997-09-25	Supramolecular polymer
US09/285,781 US6320018B1 (en)	1996-10-04	1999-04-05	Supramolecular polymer

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL1004192		1996-10-04
NL1004192A NL1004192C2 (nl)	1996-10-04	1996-10-04	Supramoleculair polymeer.

Publications (1)

Publication Number	Publication Date
NL1004192C2 true NL1004192C2 (nl)	1998-04-07

Family

ID=19763617

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1004192A NL1004192C2 (nl)	1996-10-04	1996-10-04	Supramoleculair polymeer.

Country Status (9)

Country	Link
US (1)	US6320018B1 (de)
EP (1)	EP0929597B1 (de)
AT (1)	ATE231891T1 (de)
AU (1)	AU4401897A (de)
DE (1)	DE69718802T2 (de)
DK (1)	DK0929597T3 (de)
ES (1)	ES2191853T3 (de)
NL (1)	NL1004192C2 (de)
WO (1)	WO1998014504A1 (de)

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1996
- 1996-10-04 NL NL1004192A patent/NL1004192C2/nl not_active IP Right Cessation
1997
- 1997-09-25 DE DE69718802T patent/DE69718802T2/de not_active Expired - Lifetime
- 1997-09-25 EP EP97942292A patent/EP0929597B1/de not_active Expired - Lifetime
- 1997-09-25 WO PCT/NL1997/000535 patent/WO1998014504A1/en not_active Ceased
- 1997-09-25 ES ES97942292T patent/ES2191853T3/es not_active Expired - Lifetime
- 1997-09-25 DK DK97942292T patent/DK0929597T3/da active
- 1997-09-25 AT AT97942292T patent/ATE231891T1/de active
- 1997-09-25 AU AU44018/97A patent/AU4401897A/en not_active Abandoned
1999
- 1999-04-05 US US09/285,781 patent/US6320018B1/en not_active Expired - Lifetime

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Also Published As

Publication number	Publication date
AU4401897A (en)	1998-04-24
ES2191853T3 (es)	2003-09-16
US6320018B1 (en)	2001-11-20
EP0929597B1 (de)	2003-01-29
DE69718802T2 (de)	2003-11-20
DE69718802D1 (de)	2003-03-06
EP0929597A1 (de)	1999-07-21
DK0929597T3 (da)	2003-05-12
WO1998014504A1 (en)	1998-04-09
ATE231891T1 (de)	2003-02-15

Legal Events

Date	Code	Title	Description
1998-06-02	PD2B	A search report has been drawn up
2001-07-02	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20010501

Publication	Publication Date	Title
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