CA1265635A - Water soluble polymers - Google Patents
Water soluble polymersInfo
- Publication number
- CA1265635A CA1265635A CA000454568A CA454568A CA1265635A CA 1265635 A CA1265635 A CA 1265635A CA 000454568 A CA000454568 A CA 000454568A CA 454568 A CA454568 A CA 454568A CA 1265635 A CA1265635 A CA 1265635A
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- molecular weight
- process according
- acid
- cation
- 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 - Lifetime
Links
- 229920003169 water-soluble polymer Polymers 0.000 title claims abstract description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 154
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000002253 acid Substances 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000008346 aqueous phase Substances 0.000 claims abstract description 21
- 239000012074 organic phase Substances 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 57
- 239000000178 monomer Substances 0.000 claims description 51
- 239000000243 solution Substances 0.000 claims description 50
- 150000001768 cations Chemical class 0.000 claims description 46
- 239000002585 base Substances 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 27
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 24
- 239000012071 phase Substances 0.000 claims description 24
- 230000002378 acidificating effect Effects 0.000 claims description 22
- 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 claims description 20
- 239000002798 polar solvent Substances 0.000 claims description 19
- 229910052708 sodium Inorganic materials 0.000 claims description 19
- 239000011734 sodium Substances 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 15
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 15
- 229910052744 lithium Inorganic materials 0.000 claims description 15
- 229910052700 potassium Inorganic materials 0.000 claims description 15
- 239000011591 potassium Substances 0.000 claims description 15
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 14
- 238000005191 phase separation Methods 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 6
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 3
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 claims description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical group 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 abstract description 41
- 239000000049 pigment Substances 0.000 abstract description 26
- 239000002270 dispersing agent Substances 0.000 abstract description 22
- 239000006185 dispersion Substances 0.000 abstract description 17
- 229920002125 Sokalan® Polymers 0.000 abstract description 16
- 239000004584 polyacrylic acid Substances 0.000 abstract description 14
- 229920001577 copolymer Polymers 0.000 abstract description 12
- 230000036961 partial effect Effects 0.000 abstract description 6
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 22
- 238000005194 fractionation Methods 0.000 description 19
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000000227 grinding Methods 0.000 description 12
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 9
- 229910000019 calcium carbonate Inorganic materials 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000004579 marble Substances 0.000 description 7
- 238000003801 milling Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 3
- 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 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004160 Ammonium persulphate Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 235000019395 ammonium persulphate Nutrition 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000002152 aqueous-organic solution Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- OQMMZBPPTJEAFF-UHFFFAOYSA-N 2-methylidenebutanedioic acid;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.OC(=O)CC(=C)C(O)=O OQMMZBPPTJEAFF-UHFFFAOYSA-N 0.000 description 1
- NRVQUYCYEAKQIF-UHFFFAOYSA-N 2-phenyl-2-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound C=CC(=O)NC(CS(O)(=O)=O)(C)C1=CC=CC=C1 NRVQUYCYEAKQIF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- RGHNJXZEOKUKBD-SKNVOMKLSA-N L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SKNVOMKLSA-N 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940048053 acrylate Drugs 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 101150010487 are gene Proteins 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- VEWLDLAARDMXSB-UHFFFAOYSA-N ethenyl sulfate;hydron Chemical compound OS(=O)(=O)OC=C VEWLDLAARDMXSB-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229940047670 sodium acrylate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- NFJNJCYJOUZNSO-UHFFFAOYSA-M sodium;ethenyl sulfate Chemical compound [Na+].[O-]S(=O)(=O)OC=C NFJNJCYJOUZNSO-UHFFFAOYSA-M 0.000 description 1
- DIKJULDDNQFCJG-UHFFFAOYSA-M sodium;prop-2-ene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC=C DIKJULDDNQFCJG-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/004—Pigment pastes, e.g. for mixing in paints containing an inorganic pigment
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/04—Fractionation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Extraction Or Liquid Replacement (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000601181A CA1309795C (en) | 1983-05-20 | 1989-05-30 | Water soluble polymers |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838313976A GB8313976D0 (en) | 1983-05-20 | 1983-05-20 | Water soluble polymers |
| GB8313976 | 1983-05-20 | ||
| GB838321731A GB8321731D0 (en) | 1983-08-12 | 1983-08-12 | Water soluble polymers |
| GB8321731 | 1983-08-12 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000601181A Division CA1309795C (en) | 1983-05-20 | 1989-05-30 | Water soluble polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1265635A true CA1265635A (en) | 1990-02-06 |
Family
ID=26286181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000454568A Expired - Lifetime CA1265635A (en) | 1983-05-20 | 1984-05-17 | Water soluble polymers |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US4507422A (enExample) |
| EP (2) | EP0129329B2 (enExample) |
| JP (1) | JPH02139005A (enExample) |
| CA (1) | CA1265635A (enExample) |
| DE (2) | DE3461810D1 (enExample) |
| FI (1) | FI77674C (enExample) |
| NO (1) | NO841997L (enExample) |
Families Citing this family (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2531444A1 (fr) * | 1982-08-06 | 1984-02-10 | Coatex Sa | Agent de broyage a base de polymeres et/ou copolymeres acryliques pour suspension aqueuse de materiaux mineraux grossiers en vue d'applications pigmentaires |
| FR2539137A1 (fr) * | 1982-08-06 | 1984-07-13 | Coatex Sa | Agent de broyage a base de polymeres et/ou copolymeres acryliques neutralises pour suspension aqueuse de materiaux mineraux grossiers en vue d'applications pigmentaires |
| GB8419805D0 (en) * | 1984-08-03 | 1984-09-05 | Allied Colloids Ltd | Aqueous drilling and packer fluids |
| GB8428984D0 (en) * | 1984-11-16 | 1984-12-27 | Allied Colloids Ltd | Water soluble polymers |
| AU581417B2 (en) | 1984-11-16 | 1989-02-23 | Ciba Specialty Chemicals Water Treatments Limited | Water soluble polymers and dispersions containing them |
| AU618032B2 (en) * | 1984-11-16 | 1991-12-12 | Ciba Specialty Chemicals Water Treatments Limited | Separating water soluble polymers |
| FR2577568B1 (fr) * | 1985-02-19 | 1987-12-18 | Coatex Sa | Agent fluidifiant non polluant pour fluides de forage a base d'eau douce ou saline |
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| FR2581651B1 (fr) * | 1985-05-13 | 1988-02-26 | Rhone Poulenc Spec Chim | Dispersants pour fluides de forage et fluides de forage les contenant |
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| US4715971A (en) * | 1985-12-09 | 1987-12-29 | Engineering & Colloid, Ltd. | Well drilling and completion composition |
| US4826611A (en) * | 1985-12-09 | 1989-05-02 | Engineering & Colloid, Ltd. | Well drilling and completion composition |
| US4721576A (en) * | 1985-12-13 | 1988-01-26 | Hale Arthur H | Well drilling fluids and process for drilling wells |
| US4812244A (en) * | 1985-12-13 | 1989-03-14 | Pony Industries, Inc. | Well drilling fluids and process for drilling wells |
| US4728445A (en) * | 1985-12-13 | 1988-03-01 | Pony Industries, Inc. | Well drilling fluids and process for drilling wells |
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| US4711731A (en) * | 1986-02-06 | 1987-12-08 | Diamond Shamrock Chemicals Company | Drilling fluid dispersant |
| US4814389A (en) * | 1986-02-06 | 1989-03-21 | Diamond Shamrock Chemicals Company | Drilling fluid dispersant |
| US4745154A (en) * | 1986-04-14 | 1988-05-17 | Alco Chemical Corporation | Water soluble polymers, their preparation and their uses |
| US4891401A (en) * | 1986-09-30 | 1990-01-02 | E. I. Du Pont De Nemours And Company | Pigment dispersant resin with P-containing acid |
| WO1988002381A1 (en) * | 1986-09-30 | 1988-04-07 | E.I. Du Pont De Nemours And Company | Pigment dispersant resin with s-containing acid |
| FR2610637B1 (fr) * | 1987-02-11 | 1989-05-12 | Coatex Sa | Agent de pretraitement de materiaux mineraux grossiers en vue d'applications pigmentaires |
| US4976997A (en) * | 1987-06-15 | 1990-12-11 | Chemco Technologies, Inc. | Surface composition for a substrate and method of preparation |
| US4935463A (en) * | 1987-06-15 | 1990-06-19 | Chemco Technologies, Inc. | Surface composition for a substrate and method of preparation |
| US4770795A (en) * | 1987-08-24 | 1988-09-13 | Nalco Chemical Company | Calcium tolerant deflocculant for drilling fluids |
| IL88054A0 (en) * | 1987-10-19 | 1989-06-30 | Union Carbide Corp | Stable aqueous dispersions of water-insoluble particulate solids and processes for the preparation thereof |
| US5275650A (en) * | 1987-10-23 | 1994-01-04 | Coatex S.A. | Agent for grinding lime to augment its reactivity |
| US5693692A (en) * | 1988-05-02 | 1997-12-02 | Huntsman Petrochemical Corp. | Depressant for flotation separation of polymetallic sulphide ores |
| DE3833045A1 (de) * | 1988-09-29 | 1990-04-05 | Henkel Kgaa | Bohrspueladditive auf basis eines polymergemiches, deren verwendung sowie verfahren zur herstellung derselben |
| US5032295A (en) * | 1989-04-25 | 1991-07-16 | National Starch And Chemical Investment Holding Corporation | Polymers for use in drilling muds |
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| DE4104573A1 (de) * | 1991-02-14 | 1992-08-20 | Pluss Stauffer Ag | Verfahren und vorrichtung zur technischen fraktionierung von polymeren |
| TW213474B (enExample) * | 1991-07-17 | 1993-09-21 | Cargill Inc | |
| FR2683538B1 (fr) * | 1991-11-12 | 1993-12-31 | Coatex Sa | Procede de broyage en suspension aqueuse en presence d'un agent de broyage neutralise en partie par du magnesium. |
| FR2683537B1 (fr) * | 1991-11-12 | 1993-12-31 | Coatex Sa | Agent de broyage et/ou de dispersion a base de polymeres et/ou copolymeres neutralises en partie par du magnesium pour suspensions aqueuses de materiaux mineraux en vue d'applications pigmentaires. |
| FR2683539B1 (fr) * | 1991-11-12 | 1993-12-31 | Coatex Sa | Procede de broyage en suspension aqueuse en presence d'un agent de broyage neutralise en partie par du magnesium. |
| FR2683536B1 (fr) * | 1991-11-12 | 1993-12-31 | Coatex Sa | Agent de broyage et/ou de dispersion a base de polymeres et/ou copolymeres neutralises en partie par du magnesium pour suspensions aqueuses de materiaux mineraux en vue d'applications pigmentaires. |
| CA2080961C (fr) * | 1991-11-12 | 2002-04-02 | Jean-Bernard Egraz | Agent de broyage et/ou de dispersion a base de polymeres et/ou copolymeres neutralises en partie par du magnesium pour suspensions aqueuses de materiaux mineraux en vue d'applications pigmentaires |
| EP0542643B1 (fr) * | 1991-11-12 | 1998-01-21 | Coatex S.A. | Agent de broyage et/ou de dispersion à base de polymères et/ou copolymères neutralisés en partie par du magnésium pour suspensions aqueuses de matériaux minéraux en vue d'applications pigmentaires |
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| ZA955550B (en) | 1994-07-08 | 1996-02-16 | Gillette Co | Aqueous correction fluids |
| DE4443181C2 (de) * | 1994-11-22 | 1997-12-18 | Grace W R & Co | Mittel zur Behandlung der Preßfilze von Papiermaschinen und dessen Verwendung |
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| US5810971A (en) * | 1995-05-17 | 1998-09-22 | Nalco Canada, Inc. | Liquid slurry of bentonite |
| US5891304A (en) * | 1996-07-22 | 1999-04-06 | Nalco Chemical Company | Use of hydrophilic dispersion polymers for coated broke treatment |
| US7918289B2 (en) * | 1996-07-24 | 2011-04-05 | M-I L.L.C. | Method of completing a well with sand screens |
| US20080064613A1 (en) * | 2006-09-11 | 2008-03-13 | M-I Llc | Dispersant coated weighting agents |
| US5922400A (en) * | 1997-01-09 | 1999-07-13 | The Gillette Company | Correction fluid |
| US6248697B1 (en) | 1997-02-12 | 2001-06-19 | Kb Technologies, Ltd. | Composition and method for a dual-function soil-grouting excavating or boring fluid |
| US6897186B2 (en) * | 1997-02-12 | 2005-05-24 | Kg International, Llc | Composition and method for dual function soil grouting excavating or boring fluid |
| FR2759611B1 (fr) * | 1997-02-14 | 1999-03-19 | Coatex Sa | Nouvelle utilisation de sels d'acides polyaspartiques comme agent d'aide au broyage |
| CA2236605A1 (en) * | 1997-05-09 | 1998-11-09 | Yves Duccini | Scale inhibitors |
| US6143820A (en) * | 1998-12-18 | 2000-11-07 | The Dow Chemical Company | Preparation of a low polydisperse water-soluble polymeric composition |
| AU761689B2 (en) * | 1999-04-20 | 2003-06-05 | Union Carbide Chemicals & Plastics Technology Corporation | Pigmented compositions |
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| FR2818166B1 (fr) | 2000-12-20 | 2003-10-31 | Coatex Sas | Agent d'aide au broyage et/ou de dispersion de materiaux mineraux en suspension aqueuse. suspensions aqueuses obtenues et leurs utilisations |
| EP1262463B1 (de) * | 2001-06-02 | 2004-10-27 | Cognis Iberia, S.L. | Wässrige Rohstoffzusammensetzungen für keramische Werkstoffe |
| EP1270530A1 (de) * | 2001-06-20 | 2003-01-02 | Cognis Iberia, S.L. | Abbindeverzögerer für Gips |
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| FR2864455B1 (fr) * | 2003-12-24 | 2006-03-17 | Coatex Sas | Utilisation de polymeres hydrosolubles structures obtenus par polymerisation radicalaire controlee comme dispersant et agent d'aide au broyage de matieres minerales |
| EP1806370B1 (en) * | 2004-09-30 | 2013-05-22 | JSR Corporation | Copolymer and upper film-forming composition |
| DE602006011824D1 (de) | 2005-07-07 | 2010-03-11 | Rohm & Haas | Verfahren zur Herstellung von Schlämmen |
| EP1752499A1 (en) | 2005-07-25 | 2007-02-14 | Omya Development AG | Process to disperse and/or grind and/or concentrate calcium carbonate in aqueous media using an aqueous solution containing zirconium compounds |
| FR2895686B1 (fr) * | 2005-12-30 | 2008-05-30 | Coatex Sas | Utilisation d'agents de co-broyage dans un procede de fabrication de carbonates de calcium naturel et precipite co-broyes, suspensions et pigments secs obtenus et leurs utilisations |
| WO2007093687A1 (fr) * | 2006-02-10 | 2007-08-23 | Euracli | Argiles modifiees, procede d'obtention et applications |
| WO2009012202A1 (en) * | 2007-07-13 | 2009-01-22 | Kemira Oyj | Mineral dispersants and methods for preparing mineral slurries using the same |
| JP5113784B2 (ja) | 2008-03-31 | 2013-01-09 | ローム アンド ハース カンパニー | （メタ）アクリル酸のホモポリマーおよび／またはコポリマーを含む分散剤を使用して水性分散物中で鉱物を粉砕する方法 |
| DK2143688T3 (en) | 2008-07-07 | 2017-01-09 | Omya Int Ag | A process for the preparation of aqueous suspensions of calcium carbonate, and the resulting suspensions as well as uses thereof |
| EP2194103A1 (en) | 2008-12-04 | 2010-06-09 | Omya Development Ag | Process for manufacturing calcium carbonate materials having a particle surface with improved adsorption properties |
| EP2199348A1 (en) | 2008-12-19 | 2010-06-23 | Omya Development AG | Process for manufacturing aqueous suspensions of mineral materials or dried mineral materials, the obtained products, as well as uses thereof |
| EP2390284B2 (en) | 2010-05-28 | 2017-03-15 | Omya International AG | Process for manufacturing high solids suspensions of mineral materials |
| FR2968219B1 (fr) * | 2010-12-02 | 2012-12-14 | Coatex Sas | Utilisation de sels alcalins de carbonate pour reduire la dose de polymere acrylique dans un procede de broyage de carbonate de calcium dans l'eau. |
| US8623790B2 (en) | 2010-12-21 | 2014-01-07 | Newpark Drilling Fluids Llc | Method of drilling a subterranean well with crosslinked polyacrylic acid |
| FR2972649B1 (fr) * | 2011-03-18 | 2013-03-15 | Coatex Sas | Procede de broyage de carbonate de calcium dans l'eau en presence d'une solution de polymere acrylique et d'un sel alcalin de carbonate fabrique in situ dans ladite solution |
| MX354504B (es) | 2011-06-02 | 2018-03-07 | Rohm & Haas | Composición polimérica anfotérica. |
| FR2982887B1 (fr) | 2011-11-18 | 2014-01-31 | Coatex Sas | Polymeres faiblement anioniques pour sauces de couchage destinees a des papiers pour impression de type jet d'encre |
| FR2988396A1 (fr) | 2012-03-23 | 2013-09-27 | Coatex Sas | Utilisation de polymeres faiblement ioniques comme agents compatibilisants dans des suspensions aqueuses de charges minerales anioniques contenant un sel mineral ou organique |
| SI2712895T1 (sl) | 2012-09-26 | 2016-09-30 | Omya International Ag | Reološko stabilna vodna suspenzija mineralne snovi, ki vsebuje organske polimere, ki imajo zmanjšano vsebnost hlapno organske spojine (voc) |
| SI2910609T1 (sl) | 2014-02-21 | 2017-11-30 | Omya International Ag | Postopek za pripravo polnilnega proizvoda na osnovi kalcijevega karbonata |
| AU2015268689A1 (en) | 2014-12-16 | 2016-06-30 | Stanley Black & Decker Inc. | Chalk line device |
| EP3523381B1 (en) * | 2016-10-07 | 2020-12-09 | Basf Se | Latex paint containing titanium dioxide pigment |
| JP2019536840A (ja) * | 2016-10-07 | 2019-12-19 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 二酸化チタン顔料を含有するラテックス塗料 |
| CN116694142A (zh) * | 2023-08-07 | 2023-09-05 | 晋江厚德印花有限公司 | 着色效果好的转印膜打印用颜料及其制备方法 |
| EP4613816A1 (de) * | 2024-03-05 | 2025-09-10 | Gebrüder Dorfner GmbH & Co. KG | Partikel mit einer polymer-beschichtung sowie verfahren zur herstellung dieser beschichteten partikel und deren anwendung |
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| NL104335C (enExample) * | 1953-08-11 | |||
| US3296172A (en) * | 1963-02-28 | 1967-01-03 | Du Pont | Preparing aqueous polymer dispersions in presence of polar liquids |
| GB1375731A (enExample) * | 1971-06-03 | 1974-11-27 | ||
| GB1414964A (en) * | 1971-10-19 | 1975-11-19 | English Clays Lovering Pochin | Copolymers and their use in the treatment of materials |
| DE2225317C3 (de) * | 1972-05-25 | 1978-06-01 | Basf Ag, 6700 Ludwigshafen | Papierstreichmassen |
| US3759860A (en) * | 1972-06-19 | 1973-09-18 | Uniroyal Inc | Coating compositions and coated articles |
| AU473121B2 (en) * | 1973-02-01 | 1976-06-10 | Bayer Aktiengesellschaft | Pulverizable acrylic resins |
| US3794608A (en) * | 1973-05-11 | 1974-02-26 | Dow Chemical Co | Aqueous coating compositions thickened by a terpolymer of an alkenyl aromatic compound,an unsaturated dicarboxylic acid,and an ether of vinyl benzyl alcohol and an oxyalkylated compound |
| GB1505555A (en) * | 1975-03-04 | 1978-03-30 | Allied Colloids Ltd | Water based surface coatings |
| DE2832111A1 (de) * | 1978-07-21 | 1980-01-31 | Dynamit Nobel Ag | Waessrige fuellstoff-suspension |
| CA1146694A (en) * | 1978-08-31 | 1983-05-17 | David Z. Becher | Pigment dispersants for coating compositions |
| FR2488814A1 (fr) * | 1980-08-21 | 1982-02-26 | Coatex Sa | Agent de broyage pour suspension aqueuse de materiaux mineraux en vue d'applications pigmentaires |
| US4419466A (en) * | 1981-06-25 | 1983-12-06 | The Lubrizol Corporation | Method for continuous production of invert emulsion polymers |
| US4681918A (en) * | 1981-06-30 | 1987-07-21 | E. I. Du Pont De Nemours And Company | "Living" polymers and process for their preparation |
| FR2514746B1 (fr) * | 1981-10-20 | 1985-05-31 | Coatex Sa | Agent inhibiteur d'incrustations et de precipitation pour le traitement des eaux industrielles et/ou domestiques |
| US4435528A (en) * | 1981-12-21 | 1984-03-06 | The Dow Chemical Company | Concentrated emulsions of water-soluble polymers |
| EP0108842B1 (en) * | 1982-11-10 | 1987-03-18 | Ciba Specialty Chemicals Water Treatments Limited | Calcium carbonate dispersions |
-
1984
- 1984-05-16 DE DE8484303332T patent/DE3461810D1/de not_active Expired
- 1984-05-16 EP EP84303333A patent/EP0129329B2/en not_active Expired - Lifetime
- 1984-05-16 EP EP84303332A patent/EP0127388B1/en not_active Expired
- 1984-05-16 DE DE8484303333T patent/DE3479223D1/de not_active Expired
- 1984-05-17 CA CA000454568A patent/CA1265635A/en not_active Expired - Lifetime
- 1984-05-17 FI FI841990A patent/FI77674C/fi not_active IP Right Cessation
- 1984-05-18 NO NO841997A patent/NO841997L/no unknown
- 1984-05-21 US US06/612,516 patent/US4507422A/en not_active Expired - Lifetime
- 1984-05-21 US US06/612,185 patent/US4503172A/en not_active Expired - Lifetime
- 1984-11-16 US US06/672,308 patent/US4554307A/en not_active Expired - Lifetime
- 1984-11-16 US US06/672,312 patent/US4554298A/en not_active Expired - Lifetime
-
1989
- 1989-09-28 JP JP1256892A patent/JPH02139005A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0127388B1 (en) | 1986-12-30 |
| EP0129329B2 (en) | 1998-04-01 |
| JPH02139005A (ja) | 1990-05-29 |
| US4507422A (en) | 1985-03-26 |
| FI77674B (fi) | 1988-12-30 |
| EP0129329B1 (en) | 1989-08-02 |
| FI841990L (fi) | 1984-11-21 |
| NO841997L (no) | 1984-11-21 |
| DE3479223D1 (en) | 1989-09-07 |
| US4503172A (en) | 1985-03-05 |
| DE3461810D1 (en) | 1987-02-05 |
| EP0129329A2 (en) | 1984-12-27 |
| US4554298A (en) | 1985-11-19 |
| EP0129329A3 (en) | 1986-04-16 |
| FI77674C (fi) | 1989-04-10 |
| JPH0327563B2 (enExample) | 1991-04-16 |
| US4554307A (en) | 1985-11-19 |
| FI841990A0 (fi) | 1984-05-17 |
| EP0127388A1 (en) | 1984-12-05 |
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| MKLA | Lapsed |