DE2504031C2 - - Google Patents
Info
- Publication number
- DE2504031C2 DE2504031C2 DE2504031A DE2504031A DE2504031C2 DE 2504031 C2 DE2504031 C2 DE 2504031C2 DE 2504031 A DE2504031 A DE 2504031A DE 2504031 A DE2504031 A DE 2504031A DE 2504031 C2 DE2504031 C2 DE 2504031C2
- Authority
- DE
- Germany
- Prior art keywords
- water
- gel
- washed
- mixture
- acetone
- 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.)
- Expired
Links
- 239000000499 gel Substances 0.000 claims description 82
- 229920001577 copolymer Polymers 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- -1 hydroxyalkyl methacrylates Chemical class 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 229920001222 biopolymer Polymers 0.000 claims description 2
- 238000005341 cation exchange Methods 0.000 claims description 2
- 239000007857 degradation product Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- OIEWLITYBUYJOH-UHFFFAOYSA-N 2,3-bis(ethenyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=C)=C1C=C OIEWLITYBUYJOH-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 claims 1
- 229920000151 polyglycol Polymers 0.000 claims 1
- 239000010695 polyglycol Substances 0.000 claims 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 claims 1
- 229920000193 polymethacrylate Polymers 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 124
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 101
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 98
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
- 239000000203 mixture Substances 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 29
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 24
- 230000007717 exclusion Effects 0.000 description 24
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 13
- 239000012153 distilled water Substances 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 238000004448 titration Methods 0.000 description 5
- 238000000954 titration curve Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical class OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 2
- OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical compound CC(=C)C(=O)OO OELQSSWXRGADDE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 1
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 description 1
- MZGMQAMKOBOIDR-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCO MZGMQAMKOBOIDR-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- KBXUTBMGSKKPFL-UHFFFAOYSA-N 3-hydroxy-2-methylprop-2-enoic acid Chemical class OC=C(C)C(O)=O KBXUTBMGSKKPFL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 108010038061 Chymotrypsinogen Proteins 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910004879 Na2S2O5 Inorganic materials 0.000 description 1
- 108010047320 Pepsinogen A Proteins 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- BVIXLMYIFZGRBH-UHFFFAOYSA-M sodium;2-chloroethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCl BVIXLMYIFZGRBH-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C08F8/00—Chemical modification by after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS704A CS171963B1 (en, 2012) | 1974-02-01 | 1974-02-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2504031A1 DE2504031A1 (de) | 1975-08-07 |
| DE2504031C2 true DE2504031C2 (en, 2012) | 1988-06-30 |
Family
ID=5339634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752504031 Granted DE2504031A1 (de) | 1974-02-01 | 1975-01-31 | Verfahren zur herstellung von kationenaustauschern durch substitution der hydrophilen polymeren gele |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3991018A (en, 2012) |
| JP (1) | JPS5921882B2 (en, 2012) |
| AT (1) | AT336510B (en, 2012) |
| AU (1) | AU498969B2 (en, 2012) |
| CH (1) | CH623836A5 (en, 2012) |
| CS (1) | CS171963B1 (en, 2012) |
| DE (1) | DE2504031A1 (en, 2012) |
| FR (1) | FR2259868B1 (en, 2012) |
| GB (4) | GB1503601A (en, 2012) |
| NL (1) | NL182885C (en, 2012) |
| SE (1) | SE424187B (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL49752A (en) * | 1975-07-09 | 1979-07-25 | Kabi Ab | Compositions having affinity for hepatitis virus and method for hepatitis virus removal or concentration |
| US4169051A (en) * | 1976-06-22 | 1979-09-25 | Eisai Co., Ltd. | Blood purification with coated activated carbon spheres |
| US4239854A (en) * | 1978-04-24 | 1980-12-16 | Sumitomo Chemical Company, Limited | Enzyme-immobilization carriers and preparation thereof |
| US4415679A (en) * | 1981-10-26 | 1983-11-15 | E. I. Du Pont De Nemours & Co. | Process for esterifying fluorinated carboxylic acid polymer |
| JPS5964635A (ja) * | 1982-10-06 | 1984-04-12 | Fujikura Kasei Kk | 吸水性樹脂の製造方法 |
| US4543363A (en) * | 1983-06-15 | 1985-09-24 | Asahi Kasei Kogyo Kabushiki Kaisha | Ion exchanger having hydroxyl groups bonded directly to backbone skeleton |
| AT393114B (de) * | 1989-06-08 | 1991-08-26 | Chemiefaser Lenzing Ag | Verfahren zur abtrennung von aminen |
| US5679281A (en) * | 1992-07-24 | 1997-10-21 | Yeda Research And Development Co. Ltd. | Gelled material compositions with modified halopolymer |
| IL102636A (en) * | 1992-07-24 | 1996-10-16 | Yeda Res & Dev | Gelled material compositions and their preparation |
| DE4244548C2 (de) * | 1992-12-30 | 1997-10-02 | Stockhausen Chem Fab Gmbh | Pulverförmige, unter Belastung wäßrige Flüssigkeiten sowie Blut absorbierende Polymere, Verfahren zu ihrer Herstellung und ihre Verwendung in textilen Konstruktionen für die Körperhygiene |
| FR2777286A1 (fr) * | 1998-04-09 | 1999-10-15 | Atochem Elf Sa | Polymeres hydrophiles fluores et compositions de lutte contre l'incendie les contenant |
| US7232520B1 (en) * | 1998-06-12 | 2007-06-19 | Waters Investments Limited | Ion exchange porous resins for solid phase extraction and chromatography |
| JP4883837B2 (ja) * | 1998-06-12 | 2012-02-22 | ウォーターズ・テクノロジーズ・コーポレーション | 固相抽出及びクロマトグラフィー用の新規なイオン交換多孔質樹脂 |
| US6759442B2 (en) * | 2000-06-02 | 2004-07-06 | Showa Denko Kabushiki Kaisha | Packing material for solid phase extraction and solid phase extraction method |
| US6624205B2 (en) * | 2001-01-29 | 2003-09-23 | Tosoh Corporation | Cation exchanger, process for producing same, and its use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3880818A (en) * | 1972-01-03 | 1975-04-29 | Mitchel Shen | Physiologically compatible plastic contact lenses and a method for their production |
| CS158458B1 (en, 2012) * | 1972-05-02 | 1974-11-25 |
-
1974
- 1974-02-01 CS CS704A patent/CS171963B1/cs unknown
-
1975
- 1975-01-28 GB GB3746/75A patent/GB1503601A/en not_active Expired
- 1975-01-28 GB GB40272/77A patent/GB1503603A/en not_active Expired
- 1975-01-28 GB GB40271/77A patent/GB1503602A/en not_active Expired
- 1975-01-28 GB GB40273/77A patent/GB1503604A/en not_active Expired
- 1975-01-29 US US05/545,017 patent/US3991018A/en not_active Expired - Lifetime
- 1975-01-29 CH CH103775A patent/CH623836A5/de not_active IP Right Cessation
- 1975-01-29 SE SE7500959A patent/SE424187B/xx not_active IP Right Cessation
- 1975-01-30 NL NLAANVRAGE7501134,A patent/NL182885C/xx not_active IP Right Cessation
- 1975-01-30 JP JP50011976A patent/JPS5921882B2/ja not_active Expired
- 1975-01-31 DE DE19752504031 patent/DE2504031A1/de active Granted
- 1975-02-03 FR FR7503207A patent/FR2259868B1/fr not_active Expired
- 1975-02-03 AT AT79575A patent/AT336510B/de not_active IP Right Cessation
- 1975-02-10 AU AU78041/75A patent/AU498969B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1503601A (en) | 1978-03-15 |
| CS171963B1 (en, 2012) | 1976-11-29 |
| GB1503603A (en) | 1978-03-15 |
| JPS50114492A (en, 2012) | 1975-09-08 |
| DE2504031A1 (de) | 1975-08-07 |
| GB1503604A (en) | 1978-03-15 |
| AU7804175A (en) | 1976-08-12 |
| CH623836A5 (en, 2012) | 1981-06-30 |
| AT336510B (de) | 1977-05-10 |
| NL182885B (nl) | 1988-01-04 |
| SE7500959L (en, 2012) | 1975-08-04 |
| JPS5921882B2 (ja) | 1984-05-23 |
| SE424187B (sv) | 1982-07-05 |
| NL182885C (nl) | 1988-06-01 |
| FR2259868B1 (en, 2012) | 1979-01-12 |
| US3991018A (en) | 1976-11-09 |
| NL7501134A (nl) | 1975-08-05 |
| AU498969B2 (en) | 1979-03-29 |
| ATA79575A (de) | 1976-08-15 |
| GB1503602A (en) | 1978-03-15 |
| FR2259868A1 (en, 2012) | 1975-08-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2504031C2 (en, 2012) | ||
| DE2655361C2 (de) | Dextranderivat-Gel | |
| DE2552510C3 (de) | Biologisch aktive Verbindungen und Verfahren zu ihrer Herstellung | |
| DE2505870C2 (en, 2012) | ||
| CH622716A5 (en, 2012) | ||
| CH619244A5 (en, 2012) | ||
| SU806692A1 (ru) | Способ получени целлюлозных волок-НиСТыХ иОНиТОВ | |
| DE3872346T2 (de) | Ionenaustauscher aus basis von vernetztem glukomannan. | |
| EP1432513B1 (de) | Alkalistabile hydrophile sorbentien für die ionenaustauschchromatographie | |
| CH615440A5 (en, 2012) | ||
| DE19837294A1 (de) | Verfahren zur Herstellung von Selektivaustauschern | |
| DE4439444A1 (de) | Trennmaterialien und Verfahren zu ihrer Herstellung | |
| EP0416565B1 (de) | Verfahren zur Herstellung von Desoxycelluloseverbindungen | |
| DE2340520C2 (de) | Verfahren zur Herstellung von hydrophilen merkurierten Polymeren | |
| WO1996014151A9 (de) | Trennmaterialien und verfahren zu ihrer herstellung | |
| DE69314606T2 (de) | Verfahren zur Herstellung eines kugelförmigen Ionen-Austauscherharzes | |
| DE3750788T2 (de) | Polymerträger für topochemische Reaktionen, Verfahren zur Herstellung davon, hergestellte Träger und Verwendung davon. | |
| DE1094099B (de) | Photographische, lichtempfindliche Emulsion und Verfahren zu deren Herstellung | |
| CH618187A5 (en, 2012) | ||
| AT205938B (de) | Verfahren zur Herstellung von Kationenaustauschharzen der Carboxyltype | |
| CA1048200A (en) | Method for preparation of cation exchangers by substitution of hydrophilic polymeric gels | |
| AT357982B (de) | Verfahren zur herstellung von neuen vernetzten hydrophilen polymer-gelen | |
| SU622820A1 (ru) | Способ получени ионитов | |
| EP1263806B1 (de) | Alkalistabile beschichtung auf trägermaterialien | |
| DE2339111C3 (de) | Verfahren zur Reinigung von Proteinen und anderen biospezifisch adsorbierbaren Substanzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: BEETZ SEN., R., DIPL.-ING. BEETZ JUN., R., DIPL.-ING. DR.-ING. TIMPE, W., DR.-ING. SIEGFRIED, J., DIPL.-ING. SCHMITT-FUMIAN, W., PROF. DIPL.-CHEM. DR.RER.NAT. MAYR, C., DIPL.-PHYS.DR.RER.NAT., PAT.-ANWAELTE, 8000 MUENCHEN |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |