CZ102393A3 - Cross-linked copolymers of methacrylic acid anhydride - Google Patents
Cross-linked copolymers of methacrylic acid anhydride Download PDFInfo
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- CZ102393A3 CZ102393A3 CZ931023A CZ102393A CZ102393A3 CZ 102393 A3 CZ102393 A3 CZ 102393A3 CZ 931023 A CZ931023 A CZ 931023A CZ 102393 A CZ102393 A CZ 102393A CZ 102393 A3 CZ102393 A3 CZ 102393A3
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- monomer
- polymerization
- mixture
- resin
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- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 229920003145 methacrylic acid copolymer Polymers 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 72
- 229920001577 copolymer Polymers 0.000 claims abstract description 65
- 229920000642 polymer Polymers 0.000 claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 150000008064 anhydrides Chemical group 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 15
- 230000008569 process Effects 0.000 claims abstract description 13
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 7
- 238000001042 affinity chromatography Methods 0.000 claims abstract description 3
- 239000002243 precursor Substances 0.000 claims abstract description 3
- 239000002245 particle Substances 0.000 claims description 129
- 239000000178 monomer Substances 0.000 claims description 122
- 239000011347 resin Substances 0.000 claims description 67
- 229920005989 resin Polymers 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 53
- 238000006116 polymerization reaction Methods 0.000 claims description 36
- 238000004132 cross linking Methods 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 230000015572 biosynthetic process Effects 0.000 claims description 27
- 239000003999 initiator Substances 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 24
- -1 ethynylene glycol Chemical compound 0.000 claims description 22
- 239000000523 sample Substances 0.000 claims description 22
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 20
- 102000004169 proteins and genes Human genes 0.000 claims description 19
- 108090000623 proteins and genes Proteins 0.000 claims description 19
- 102100030497 Cytochrome c Human genes 0.000 claims description 16
- 108010075031 Cytochromes c Proteins 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000011148 porous material Substances 0.000 claims description 16
- 238000001179 sorption measurement Methods 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 15
- 239000003361 porogen Substances 0.000 claims description 13
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000008367 deionised water Substances 0.000 claims description 11
- 229910021641 deionized water Inorganic materials 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 9
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 9
- 239000008346 aqueous phase Substances 0.000 claims description 9
- 239000007900 aqueous suspension Substances 0.000 claims description 9
- 238000005342 ion exchange Methods 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 238000000354 decomposition reaction Methods 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 238000007306 functionalization reaction Methods 0.000 claims description 8
- 150000002978 peroxides Chemical class 0.000 claims description 8
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 230000008859 change Effects 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000005395 methacrylic acid group Chemical class 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 6
- 238000005191 phase separation Methods 0.000 claims description 6
- 230000008929 regeneration Effects 0.000 claims description 6
- 238000011069 regeneration method Methods 0.000 claims description 6
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 5
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 4
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 238000002835 absorbance Methods 0.000 claims description 4
- 239000008351 acetate buffer Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 230000008901 benefit Effects 0.000 claims description 4
- 239000000872 buffer Substances 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims description 4
- 230000002209 hydrophobic effect Effects 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 238000010526 radical polymerization reaction Methods 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- 238000005185 salting out Methods 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- 229960005322 streptomycin Drugs 0.000 claims description 4
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 claims description 3
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 claims description 3
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 claims description 3
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 3
- 229920000609 methyl cellulose Polymers 0.000 claims description 3
- 239000001923 methylcellulose Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 claims description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims description 2
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 claims description 2
- WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 claims description 2
- 241000195493 Cryptophyta Species 0.000 claims description 2
- 108010052832 Cytochromes Proteins 0.000 claims description 2
- 102000018832 Cytochromes Human genes 0.000 claims description 2
- 102000004127 Cytokines Human genes 0.000 claims description 2
- 108090000695 Cytokines Proteins 0.000 claims description 2
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
- 241001611408 Nebo Species 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 229920002873 Polyethylenimine Polymers 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229920000297 Rayon Polymers 0.000 claims description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
- 241000244317 Tillandsia usneoides Species 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 229910052925 anhydrite Inorganic materials 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000013011 aqueous formulation Substances 0.000 claims description 2
- 238000003556 assay Methods 0.000 claims description 2
- FPODCVUTIPDRTE-UHFFFAOYSA-N bis(prop-2-enyl) hexanedioate Chemical compound C=CCOC(=O)CCCCC(=O)OCC=C FPODCVUTIPDRTE-UHFFFAOYSA-N 0.000 claims description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 2
- 238000005341 cation exchange Methods 0.000 claims description 2
- 239000003729 cation exchange resin Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 claims description 2
- 238000005520 cutting process Methods 0.000 claims description 2
- 229960002887 deanol Drugs 0.000 claims description 2
- 238000009792 diffusion process Methods 0.000 claims description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
- 230000009977 dual effect Effects 0.000 claims description 2
- 210000005069 ears Anatomy 0.000 claims description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 2
- 230000007613 environmental effect Effects 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 claims description 2
- 239000007863 gel particle Substances 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002432 hydroperoxides Chemical class 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 210000004417 patella Anatomy 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 230000003389 potentiating effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000012716 precipitator Substances 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims description 2
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 239000012966 redox initiator Substances 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 239000013074 reference sample Substances 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 claims description 2
- LNDCCSBWZAQAAW-UHFFFAOYSA-M sodium hydrogen sulfate sulfuric acid Chemical compound [Na+].OS(O)(=O)=O.OS([O-])(=O)=O LNDCCSBWZAQAAW-UHFFFAOYSA-M 0.000 claims description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 claims description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000012086 standard solution Substances 0.000 claims description 2
- 229960002385 streptomycin sulfate Drugs 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000000375 suspending agent Substances 0.000 claims description 2
- 230000008961 swelling Effects 0.000 claims description 2
- 239000002699 waste material Substances 0.000 claims description 2
- 239000002351 wastewater Substances 0.000 claims description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- HGDULKQRXBSKHL-UHFFFAOYSA-N 1,1-bis(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(CC)(OC(=O)C(C)=C)OC(=O)C(C)=C HGDULKQRXBSKHL-UHFFFAOYSA-N 0.000 claims 1
- NNNLYDWXTKOQQX-UHFFFAOYSA-N 1,1-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OC(CC)(OC(=O)C=C)OC(=O)C=C NNNLYDWXTKOQQX-UHFFFAOYSA-N 0.000 claims 1
- ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 claims 1
- LMWVCJZYRYMGSL-UHFFFAOYSA-N 2-methylprop-2-enoic acid;propane Chemical compound CCC.CC(=C)C(O)=O.CC(=C)C(O)=O LMWVCJZYRYMGSL-UHFFFAOYSA-N 0.000 claims 1
- KHAHWKLZGBIAKT-UHFFFAOYSA-N 4-(4-methylpyrimidin-2-yl)benzaldehyde Chemical compound CC1=CC=NC(C=2C=CC(C=O)=CC=2)=N1 KHAHWKLZGBIAKT-UHFFFAOYSA-N 0.000 claims 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- XCHLRFRZJLYDOF-UHFFFAOYSA-N CCC.OC(=O)C=C.OC(=O)C=C Chemical compound CCC.OC(=O)C=C.OC(=O)C=C XCHLRFRZJLYDOF-UHFFFAOYSA-N 0.000 claims 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- ZPOLOEWJWXZUSP-AATRIKPKSA-N bis(prop-2-enyl) (e)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C\C(=O)OCC=C ZPOLOEWJWXZUSP-AATRIKPKSA-N 0.000 claims 1
- BKXRKRANFLFTFU-UHFFFAOYSA-N bis(prop-2-enyl) oxalate Chemical compound C=CCOC(=O)C(=O)OCC=C BKXRKRANFLFTFU-UHFFFAOYSA-N 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 claims 1
- 125000004386 diacrylate group Chemical group 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- UUQPAGXXWIOCCL-UHFFFAOYSA-N ethyl 2-[(1-ethoxy-2-methyl-1-oxopentan-2-yl)diazenyl]-2-methylpentanoate Chemical compound CCOC(=O)C(C)(CCC)N=NC(C)(CCC)C(=O)OCC UUQPAGXXWIOCCL-UHFFFAOYSA-N 0.000 claims 1
- HJWBBBADPXPUPA-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylate Chemical compound CCOC(=O)C1=C(C)ON=C1C1=CC=C(Cl)C=C1 HJWBBBADPXPUPA-UHFFFAOYSA-N 0.000 claims 1
- QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 claims 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical class C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract 2
- 239000011324 bead Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/16—Making expandable particles
- C08J9/20—Making expandable particles by suspension polymerisation in the presence of the blowing agent
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/38—Selective adsorption, e.g. chromatography characterised by the separation mechanism involving specific interaction not covered by one or more of groups B01D15/265 and B01D15/30 - B01D15/36, e.g. affinity, ligand exchange or chiral chromatography
- B01D15/3804—Affinity chromatography
- B01D15/3809—Affinity chromatography of the antigen-antibody type, e.g. protein A, G or L chromatography
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
-
- 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
-
- 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
- B01J43/00—Amphoteric ion-exchange, i.e. using ion-exchangers having cationic and anionic groups; Use of material as amphoteric ion-exchangers; Treatment of material for improving their amphoteric ion-exchange 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/08—Anhydrides
-
- 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
- C08F220/08—Anhydrides
-
- 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
-
- 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
- C08F8/12—Hydrolysis
-
- 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
- C08F8/44—Preparation of metal salts or ammonium salts
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polymerisation Methods In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89138192A | 1992-05-29 | 1992-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ102393A3 true CZ102393A3 (en) | 1993-12-15 |
Family
ID=25398095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ931023A CZ102393A3 (en) | 1992-05-29 | 1993-05-28 | Cross-linked copolymers of methacrylic acid anhydride |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5639861A (OSRAM) |
| EP (1) | EP0572115B1 (OSRAM) |
| JP (1) | JP3594629B2 (OSRAM) |
| KR (1) | KR100286528B1 (OSRAM) |
| CN (1) | CN1042434C (OSRAM) |
| AT (1) | ATE163657T1 (OSRAM) |
| AU (1) | AU3710093A (OSRAM) |
| BR (1) | BR9302022A (OSRAM) |
| CA (1) | CA2096492A1 (OSRAM) |
| CZ (1) | CZ102393A3 (OSRAM) |
| DE (1) | DE69317154T2 (OSRAM) |
| HU (1) | HU213523B (OSRAM) |
| MX (1) | MX9302873A (OSRAM) |
| NO (1) | NO931883L (OSRAM) |
| NZ (1) | NZ247458A (OSRAM) |
| SK (1) | SK52493A3 (OSRAM) |
| TW (1) | TW222283B (OSRAM) |
| ZA (1) | ZA933060B (OSRAM) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6107429A (en) * | 1994-10-24 | 2000-08-22 | Amcol International Corporation | Process for producing an oil and water adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
| US5830967A (en) * | 1994-10-24 | 1998-11-03 | Amcol International Corporation | Process for producing an oil and water adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
| US5837790A (en) | 1994-10-24 | 1998-11-17 | Amcol International Corporation | Precipitation polymerization process for producing an oil adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
| US5712358A (en) * | 1995-06-07 | 1998-01-27 | Amcol International Corporation | Process for producing an oil sorbent copolymer and the product thereof |
| IT1282651B1 (it) * | 1996-02-19 | 1998-03-31 | Atohaas Holding Cv | Processo per la preparazione di perle di polimeri a base acrilica |
| US6228340B1 (en) | 1997-08-25 | 2001-05-08 | The Regents Of The University Of California | Method for the production of macroporous ceramics |
| US6274687B1 (en) * | 1997-09-04 | 2001-08-14 | Daiso Co., Ltd. | Powder of agglomerated fine particles of crosslinked allyl copolymer |
| FR2781232B1 (fr) * | 1998-07-15 | 2000-09-08 | Centre Nat Rech Scient | Polymere reactif utilisable pour la separation et l'adsorption de substances organiques, et materiau le contenant |
| DE19907023A1 (de) * | 1999-02-19 | 2000-08-24 | Bayer Ag | Verfahren zur Isolierung von Nucleinsäuren |
| GB9918437D0 (en) * | 1999-08-05 | 1999-10-06 | Anglo American Platinum Corp | Separation of platinium group metals |
| DE50205698D1 (de) * | 2002-10-22 | 2006-04-13 | Metrohm Ag Herisau | Verfahren zur Herstellung von porösen Polymerteilchen auf Acrylat- und/oder Methacrylatbasis |
| US6752853B2 (en) * | 2002-10-31 | 2004-06-22 | Samsung Electronics Co., Ltd. | Article and method for elimination of hydrocarbon emissions from printer exhaust |
| CN1689695B (zh) * | 2004-04-30 | 2010-06-23 | 北京九强生物技术有限公司 | 层析颗粒介质的制备方法 |
| CA2655026C (en) | 2006-06-15 | 2016-08-02 | Microvention, Inc. | Embolization device constructed from expansible polymer |
| BRPI1014645B1 (pt) * | 2009-04-30 | 2020-07-07 | Technip France | método e sistema para compartilhar linhas de amarração |
| US10639396B2 (en) * | 2015-06-11 | 2020-05-05 | Microvention, Inc. | Polymers |
| US9499642B2 (en) * | 2011-11-11 | 2016-11-22 | Rohm And Haas Company | Small particle size hypophosphite telomers of unsaturated carboxylic acids |
| EP2748214A1 (en) | 2011-11-11 | 2014-07-02 | Rohm and Haas Company | Polymethacrylic acid anhydride telomers |
| EP2778183B1 (en) | 2013-03-15 | 2015-04-29 | Rohm and Haas Company | Polymethacrylic acid anhydride telomers |
| WO2015167752A1 (en) | 2014-04-29 | 2015-11-05 | Microvention, Inc. | Polymers including active agents |
| TW201625754A (zh) * | 2014-11-21 | 2016-07-16 | 艾倫塔斯有限公司 | 單一成份、儲存穩定、可硬化之聚矽氧組成物 |
| EP3538266B1 (en) | 2016-11-14 | 2024-08-21 | Lilac Solutions, Inc. | Lithium extraction with coated ion exchange particles |
| US11253848B2 (en) | 2017-08-02 | 2022-02-22 | Lilac Solutions, Inc. | Lithium extraction with porous ion exchange beads |
| CA3071649C (en) | 2017-08-02 | 2025-05-20 | Lilac Solutions, Inc. | ION EXCHANGE SYSTEM FOR LITHIUM EXTRACTION |
| MA52428A (fr) | 2018-02-28 | 2021-06-02 | Lilac Solutions Inc | Réacteur d'échange d'ions à piège à particules pour extraction de lithium |
| WO2020035733A1 (en) * | 2018-08-14 | 2020-02-20 | 1441413 Alberta Inc. DBA EPT | Highly porous coolant conditioning and remediation media |
| JP2023514803A (ja) | 2020-01-09 | 2023-04-11 | ライラック ソリューションズ，インク． | 望ましくない金属を分離するための方法 |
| CA3178825A1 (en) | 2020-06-09 | 2021-12-16 | David Henry SNYDACKER | Lithium extraction in the presence of scalants |
| EP4247759A1 (en) | 2020-11-20 | 2023-09-27 | Lilac Solutions, Inc. | Lithium production with volatile acid |
| JP7516243B2 (ja) * | 2020-12-25 | 2024-07-16 | 株式会社カネカ | ポリ（３－ヒドロキシアルカノエート）系発泡粒子およびポリ（３－ヒドロキシアルカノエート）系発泡成形体 |
| JP7646352B2 (ja) * | 2020-12-25 | 2025-03-17 | 株式会社カネカ | ポリ（３－ヒドロキシアルカノエート）系発泡粒子およびポリ（３－ヒドロキシアルカノエート）系発泡成形体 |
| KR20240014047A (ko) | 2021-04-23 | 2024-01-31 | 리락 솔루션즈, 인크. | 리튬 추출을 위한 이온 교환 장치 |
| WO2023192192A1 (en) | 2022-03-28 | 2023-10-05 | Lilac Solutions, Inc. | Lithium extraction enhanced by an alternate phase |
| CA3245669A1 (en) | 2022-04-01 | 2023-10-05 | Lilac Solutions, Inc. | Extraction of lithium with chemical additives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2324935A (en) * | 1938-05-20 | 1943-07-20 | Rohm & Haas | Process for polymerizing derivatives of methacrylic acid |
| US2308581A (en) * | 1939-05-05 | 1943-01-19 | Du Pont | Copolymerized substances containing methacrylic anhydride |
| GB781400A (en) * | 1954-09-13 | 1957-08-21 | Roehm & Haas Gmbh | Improvements in or relating to ion-exchange resins |
| NL213286A (OSRAM) * | 1955-12-27 | |||
| SE328716B (OSRAM) * | 1961-12-15 | 1970-09-21 | Rio Rad Lab | |
| FR1603393A (OSRAM) * | 1967-12-27 | 1971-04-13 | ||
| US4221871A (en) * | 1970-12-16 | 1980-09-09 | Rohm And Haas Company | Reticular crosslinked monovinylidene N-heterocyclic copolymer |
| DE2215687C3 (de) * | 1972-03-30 | 1980-12-11 | Bayer Ag, 5090 Leverkusen | Neue wasserunlösliche Proteinpräparate |
| US4070348A (en) * | 1973-07-25 | 1978-01-24 | Rohm Gmbh | Water-swellable, bead copolymer |
| US4229547A (en) * | 1979-03-19 | 1980-10-21 | The B. F. Goodrich Company | Method of preparing spherical porous bead-type polymers |
| JPS59225064A (ja) * | 1983-06-03 | 1984-12-18 | ユニチカ株式会社 | 生理活性物質固定化用担体 |
| PT80975B (pt) * | 1984-08-17 | 1987-11-11 | Shinetsu Chemical Co | Processo para a preparacao de um polimero de vinilo |
-
1993
- 1993-04-21 AT AT93303125T patent/ATE163657T1/de not_active IP Right Cessation
- 1993-04-21 DE DE69317154T patent/DE69317154T2/de not_active Expired - Lifetime
- 1993-04-21 NZ NZ247458A patent/NZ247458A/en unknown
- 1993-04-21 EP EP93303125A patent/EP0572115B1/en not_active Expired - Lifetime
- 1993-04-23 TW TW082103119A patent/TW222283B/zh active
- 1993-04-23 AU AU37100/93A patent/AU3710093A/en not_active Abandoned
- 1993-04-30 ZA ZA933060A patent/ZA933060B/xx unknown
- 1993-05-18 CA CA002096492A patent/CA2096492A1/en not_active Abandoned
- 1993-05-18 MX MX9302873A patent/MX9302873A/es not_active IP Right Cessation
- 1993-05-20 BR BR9302022A patent/BR9302022A/pt not_active Application Discontinuation
- 1993-05-24 SK SK524-93A patent/SK52493A3/sk unknown
- 1993-05-25 NO NO931883A patent/NO931883L/no unknown
- 1993-05-27 KR KR1019930009366A patent/KR100286528B1/ko not_active Expired - Fee Related
- 1993-05-28 JP JP12733293A patent/JP3594629B2/ja not_active Expired - Fee Related
- 1993-05-28 CN CN93106493A patent/CN1042434C/zh not_active Expired - Fee Related
- 1993-05-28 HU HU9301586A patent/HU213523B/hu not_active IP Right Cessation
- 1993-05-28 CZ CZ931023A patent/CZ102393A3/cs unknown
-
1995
- 1995-06-06 US US08/467,675 patent/US5639861A/en not_active Expired - Lifetime
- 1995-06-06 US US08/467,674 patent/US5539071A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0572115A3 (OSRAM) | 1994-03-16 |
| HU213523B (en) | 1997-07-28 |
| AU3710093A (en) | 1993-12-02 |
| KR100286528B1 (ko) | 2001-04-16 |
| JP3594629B2 (ja) | 2004-12-02 |
| HUT66373A (en) | 1994-11-28 |
| CA2096492A1 (en) | 1993-11-30 |
| DE69317154D1 (de) | 1998-04-09 |
| HU9301586D0 (en) | 1993-09-28 |
| NO931883L (no) | 1993-11-30 |
| TW222283B (OSRAM) | 1994-04-11 |
| KR930023390A (ko) | 1993-12-18 |
| JPH0649139A (ja) | 1994-02-22 |
| EP0572115A2 (en) | 1993-12-01 |
| EP0572115B1 (en) | 1998-03-04 |
| ZA933060B (en) | 1993-11-29 |
| CN1042434C (zh) | 1999-03-10 |
| DE69317154T2 (de) | 1998-11-12 |
| NO931883D0 (no) | 1993-05-25 |
| CN1079229A (zh) | 1993-12-08 |
| US5639861A (en) | 1997-06-17 |
| MX9302873A (es) | 1993-11-01 |
| NZ247458A (en) | 1994-09-27 |
| US5539071A (en) | 1996-07-23 |
| ATE163657T1 (de) | 1998-03-15 |
| SK52493A3 (en) | 1993-12-08 |
| BR9302022A (pt) | 1993-12-07 |
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