OA10943A - Spray-dried polymer compositions and methods - Google Patents
Spray-dried polymer compositions and methods Download PDFInfo
- Publication number
- OA10943A OA10943A OA9800244A OA9800244A OA10943A OA 10943 A OA10943 A OA 10943A OA 9800244 A OA9800244 A OA 9800244A OA 9800244 A OA9800244 A OA 9800244A OA 10943 A OA10943 A OA 10943A
- Authority
- OA
- OAPI
- Prior art keywords
- water
- polymer
- oil
- spray
- vinyl
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 330
- 238000000034 method Methods 0.000 title claims abstract description 88
- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 239000002245 particle Substances 0.000 claims abstract description 173
- 239000004530 micro-emulsion Substances 0.000 claims abstract description 106
- 238000001694 spray drying Methods 0.000 claims abstract description 62
- 239000006185 dispersion Substances 0.000 claims abstract description 57
- 239000002253 acid Substances 0.000 claims description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
- 229910001868 water Inorganic materials 0.000 claims description 52
- 239000007787 solid Substances 0.000 claims description 35
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 18
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 17
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 13
- 238000004090 dissolution Methods 0.000 claims description 12
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical group O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001408 amides Chemical group 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 229940015043 glyoxal Drugs 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 239000010893 paper waste Substances 0.000 claims description 3
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical group OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 45
- 239000000839 emulsion Substances 0.000 abstract description 9
- 238000005065 mining Methods 0.000 abstract description 6
- 238000011084 recovery Methods 0.000 abstract description 6
- 239000002689 soil Substances 0.000 abstract description 5
- 230000008719 thickening Effects 0.000 abstract description 4
- 230000003750 conditioning effect Effects 0.000 abstract description 3
- 235000013305 food Nutrition 0.000 abstract description 3
- 238000012545 processing Methods 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 215
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 43
- 239000007789 gas Substances 0.000 description 43
- 239000002585 base Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- 239000007921 spray Substances 0.000 description 37
- 239000000872 buffer Substances 0.000 description 35
- 238000001035 drying Methods 0.000 description 32
- 229920002401 polyacrylamide Polymers 0.000 description 27
- CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical compound CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 description 21
- 239000000126 substance Substances 0.000 description 20
- 239000000178 monomer Substances 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 19
- 239000003039 volatile agent Substances 0.000 description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229920003169 water-soluble polymer Polymers 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 229940048053 acrylate Drugs 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 9
- 239000012530 fluid Substances 0.000 description 9
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 125000000129 anionic group Chemical group 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 230000008859 change Effects 0.000 description 8
- 238000009826 distribution Methods 0.000 description 7
- 239000011325 microbead Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000004815 dispersion polymer Substances 0.000 description 6
- 238000005189 flocculation Methods 0.000 description 6
- 230000016615 flocculation Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000017550 sodium carbonate Nutrition 0.000 description 6
- 238000013517 stratification Methods 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 238000010410 dusting Methods 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 229960001407 sodium bicarbonate Drugs 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000008394 flocculating agent Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000003926 acrylamides Chemical class 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- -1 dry Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229940050176 methyl chloride Drugs 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical class [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical class [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000005703 Trimethylamine hydrochloride Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000006085 branching agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920003118 cationic copolymer Polymers 0.000 description 2
- 229920006317 cationic polymer Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920005570 flexible polymer Polymers 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 229960000448 lactic acid Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Chemical class 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000010079 rubber tapping Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical group [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229960002668 sodium chloride Drugs 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 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
- 238000012546 transfer Methods 0.000 description 2
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- 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 description 1
- VAPQAGMSICPBKJ-UHFFFAOYSA-N 2-nitroacridine Chemical compound C1=CC=CC2=CC3=CC([N+](=O)[O-])=CC=C3N=C21 VAPQAGMSICPBKJ-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CJRJTCMSQLEPFQ-UHFFFAOYSA-N 6-cat Chemical compound ClC1=CC=C2CC(N)CCC2=C1 CJRJTCMSQLEPFQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- GUTLYIVDDKVIGB-OUBTZVSYSA-N Cobalt-60 Chemical compound [60Co] GUTLYIVDDKVIGB-OUBTZVSYSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229920006322 acrylamide copolymer Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229920006318 anionic polymer Polymers 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- WPKYZIPODULRBM-UHFFFAOYSA-N azane;prop-2-enoic acid Chemical compound N.OC(=O)C=C WPKYZIPODULRBM-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
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- 239000001508 potassium citrate Substances 0.000 description 1
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- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
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Classifications
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- 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
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/122—Pulverisation by spraying
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D1/00—Evaporating
- B01D1/14—Evaporating with heated gases or vapours or liquids in contact with the liquid
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
- C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
- C02F1/56—Macromolecular compounds
-
- 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
- C08J11/00—Recovery or working-up of waste materials
- C08J11/02—Recovery or working-up of waste materials of solvents, plasticisers or unreacted monomers
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
-
- 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
- C08J2300/00—Characterised by the use of unspecified polymers
- C08J2300/14—Water soluble or water swellable polymers, e.g. aqueous gels
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S210/00—Liquid purification or separation
- Y10S210/928—Paper mill waste, e.g. white water, black liquor treated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/904—Powder coating compositions
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/934—Powdered coating composition
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Sustainable Development (AREA)
- Water Supply & Treatment (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Processing Of Solid Wastes (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Paper (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/670,194 US6011089A (en) | 1995-06-07 | 1996-06-21 | Spray drying of polymer-containing dispersions, water-in-oil emulsions and water-in-oil microemulsions, and dry polymer products formed thereby |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA10943A true OA10943A (en) | 2003-02-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| OA9800244A OA10943A (en) | 1996-06-21 | 1998-12-18 | Spray-dried polymer compositions and methods |
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| US (2) | US6011089A (fr) |
| EP (1) | EP0906358B1 (fr) |
| JP (1) | JP2000513395A (fr) |
| KR (1) | KR20000016794A (fr) |
| CN (3) | CN1229442C (fr) |
| AR (1) | AR008394A1 (fr) |
| AT (1) | ATE204006T1 (fr) |
| AU (1) | AU728983B2 (fr) |
| BG (1) | BG63635B1 (fr) |
| BR (1) | BR9709861A (fr) |
| CA (1) | CA2258751C (fr) |
| CO (1) | CO4820407A1 (fr) |
| DE (1) | DE69706052T2 (fr) |
| ES (1) | ES2161471T3 (fr) |
| GR (1) | GR3036742T3 (fr) |
| ID (1) | ID17106A (fr) |
| MX (1) | MX9810585A (fr) |
| NO (1) | NO985967L (fr) |
| OA (1) | OA10943A (fr) |
| PE (1) | PE86198A1 (fr) |
| PH (1) | PH11997057030B1 (fr) |
| PL (1) | PL330713A1 (fr) |
| PT (1) | PT906358E (fr) |
| RU (1) | RU2191197C2 (fr) |
| TW (1) | TW502048B (fr) |
| UA (1) | UA52667C2 (fr) |
| WO (1) | WO1997048732A2 (fr) |
| ZA (1) | ZA975438B (fr) |
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| JP3914567B2 (ja) * | 1994-03-17 | 2007-05-16 | エクソンモービル・ケミカル・パテンツ・インク | 触媒担持体用の噴霧乾燥ポリマー |
| GB9700528D0 (en) * | 1997-01-13 | 1997-03-05 | Allied Colloids Ltd | Polymerisation processes and products |
| GB9724032D0 (en) * | 1997-11-13 | 1998-01-14 | Allied Colloids Ltd | Ore pelletisation |
| US6342652B1 (en) * | 1999-09-01 | 2002-01-29 | Nippon Shokubai Co., Ltd. | Water-swellable crosslinked polymer, its composition, and their production processes and uses |
| US6372882B1 (en) * | 2000-04-03 | 2002-04-16 | Nalco Chemical Company | Method for producing substantially dry water-insoluble polymers for improved flocculation in the bayer process |
| JP3963361B2 (ja) * | 2002-06-27 | 2007-08-22 | ハイモ株式会社 | 凝集処理薬剤及びその使用方法 |
| SE0300726D0 (sv) * | 2003-03-14 | 2003-03-14 | Amersham Biosciences Ab | Method for preparing a separation medium |
| US20050261399A1 (en) * | 2004-05-19 | 2005-11-24 | David Hunkeler | Powdered flocculants prepared by using evaporative cooling to coat polymeric materials on a porous substrate |
| DE102005016401A1 (de) * | 2005-04-08 | 2006-10-12 | Stockhausen Gmbh | Verfahren und Vorrichtung zur Herstellung konzentrierter Polymerlösungen |
| JP5557366B2 (ja) * | 2008-05-20 | 2014-07-23 | ハイモ株式会社 | 粉末からなるイオン性水溶性高分子とその製造方法およびその用途 |
| CN103787569A (zh) * | 2009-03-17 | 2014-05-14 | 勒瓦研究开发股份有限公司 | 用于调节污泥的组合物 |
| US9404686B2 (en) | 2009-09-15 | 2016-08-02 | Suncor Energy Inc. | Process for dying oil sand mature fine tailings |
| CA2936031C (fr) | 2009-09-15 | 2019-09-03 | Adrian Peter Revington | Techniques de floculation et de deshydratation de residus fins |
| WO2011050440A1 (fr) | 2009-10-30 | 2011-05-05 | Suncor Energy Inc. | Procédés de sédimentation et de traitement agricole pour le séchage de résidus fins mûrs de sables bitumineux |
| US9332776B1 (en) | 2010-09-27 | 2016-05-10 | ZoomEssence, Inc. | Methods and apparatus for low heat spray drying |
| US8939388B1 (en) | 2010-09-27 | 2015-01-27 | ZoomEssence, Inc. | Methods and apparatus for low heat spray drying |
| US8859482B2 (en) | 2011-02-14 | 2014-10-14 | Chemlink Laboratories, Llc | Method for preparing a solid form of acetic acid and products thereof |
| PE20141338A1 (es) * | 2012-01-25 | 2014-10-04 | Sortwell & Co | Metodo para dispersar y agregar componentes de suspensiones minerales y polimeros multivalentes de bajo peso molecular para agregacion mineral |
| WO2015051364A1 (fr) * | 2013-10-05 | 2015-04-09 | Omnova Solutions Inc | Superparticules comprenant des particules polymères creuses |
| US10486173B2 (en) | 2017-08-04 | 2019-11-26 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
| US9993787B1 (en) | 2017-08-04 | 2018-06-12 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
| US9861945B1 (en) | 2017-08-04 | 2018-01-09 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
| US10155234B1 (en) | 2017-08-04 | 2018-12-18 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
| WO2019028446A1 (fr) | 2017-08-04 | 2019-02-07 | ZoomEssence, Inc. | Appareil et procédé de séchage par pulvérisation à très haut rendement |
| EP3676548B1 (fr) | 2017-08-31 | 2023-05-10 | Capsugel Belgium NV | Méthode de séchage par pulvérisation utilisant une chambre de séchage à usage unique |
| US10569244B2 (en) | 2018-04-28 | 2020-02-25 | ZoomEssence, Inc. | Low temperature spray drying of carrier-free compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA672769A (en) * | 1963-10-22 | G. Hedberg Johan | Elastomers compounded by spray drying | |
| US3275449A (en) * | 1962-06-26 | 1966-09-27 | Pillsbury Co | Method of agglomerating solid particulate material |
| US3325425A (en) * | 1962-12-03 | 1967-06-13 | Monsanto Co | Spray drying of aqueous acrylic polymer dispersion paints |
| US3279924A (en) * | 1963-12-12 | 1966-10-18 | Carnation Co | Contacting apparatus and process for forming aggregates |
| US3803111A (en) * | 1972-05-15 | 1974-04-09 | Celanese Coatings Co | Process for spray-drying acrylic polymer solutions |
| JPS49124979A (fr) * | 1973-04-02 | 1974-11-29 | ||
| JPS5324115B2 (fr) * | 1974-03-22 | 1978-07-19 | ||
| US4112215A (en) * | 1975-03-20 | 1978-09-05 | Rohm Gmbh | Copolymeric resin binder powders |
| US4079027A (en) * | 1975-04-18 | 1978-03-14 | Nalco Chemical Company | Quaternary modified acrylamide polymers |
| US4035317A (en) * | 1975-06-30 | 1977-07-12 | American Cyanamid Company | Rapidly dissolving, water-soluble polymers and spray drying method for their production |
| US4171296A (en) * | 1976-07-15 | 1979-10-16 | Nalco Chemical Company | Method of hydrolyzing polyacrylamide |
| US4387499A (en) * | 1977-02-03 | 1983-06-14 | Verbatim Corporation | Leader to hub locking system |
| US4212784A (en) * | 1979-05-04 | 1980-07-15 | Nalco Chemical Co. | Polymerization of water soluble polymers in water-in-oil latex form to produce emulsions containing high polymer solids levels and low oil levels |
| US4405728A (en) * | 1982-01-15 | 1983-09-20 | Nalco Chemical Company | Compositions for on-site mannich polymer process |
| US4569991A (en) * | 1982-01-26 | 1986-02-11 | Mitsubishi Monsanto Chemical Company | Production of thermoplastic resin |
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-
1996
- 1996-06-21 US US08/670,194 patent/US6011089A/en not_active Expired - Lifetime
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1997
- 1997-05-06 UA UA99010286A patent/UA52667C2/uk unknown
- 1997-05-22 TW TW086106900A patent/TW502048B/zh not_active IP Right Cessation
- 1997-06-05 CN CNB011047127A patent/CN1229442C/zh not_active Expired - Lifetime
- 1997-06-05 AU AU34781/97A patent/AU728983B2/en not_active Expired
- 1997-06-05 EP EP97931055A patent/EP0906358B1/fr not_active Expired - Lifetime
- 1997-06-05 AT AT97931055T patent/ATE204006T1/de not_active IP Right Cessation
- 1997-06-05 KR KR1019980710404A patent/KR20000016794A/ko not_active Ceased
- 1997-06-05 JP JP10503063A patent/JP2000513395A/ja active Pending
- 1997-06-05 CN CN97195714A patent/CN1076027C/zh not_active Expired - Lifetime
- 1997-06-05 CA CA002258751A patent/CA2258751C/fr not_active Expired - Lifetime
- 1997-06-05 PL PL97330713A patent/PL330713A1/xx unknown
- 1997-06-05 BR BR9709861-2A patent/BR9709861A/pt not_active IP Right Cessation
- 1997-06-05 WO PCT/US1997/009788 patent/WO1997048732A2/fr not_active Ceased
- 1997-06-05 CN CNB2004100642368A patent/CN1284818C/zh not_active Expired - Lifetime
- 1997-06-05 RU RU99101089/04A patent/RU2191197C2/ru active
- 1997-06-05 ES ES97931055T patent/ES2161471T3/es not_active Expired - Lifetime
- 1997-06-05 PT PT97931055T patent/PT906358E/pt unknown
- 1997-06-05 DE DE69706052T patent/DE69706052T2/de not_active Expired - Lifetime
- 1997-06-10 PE PE1997000476A patent/PE86198A1/es not_active Application Discontinuation
- 1997-06-18 CO CO97033790A patent/CO4820407A1/es unknown
- 1997-06-19 PH PH57030A patent/PH11997057030B1/en unknown
- 1997-06-19 ZA ZA9705438A patent/ZA975438B/xx unknown
- 1997-06-19 ID IDP972108A patent/ID17106A/id unknown
- 1997-06-20 AR ARP970102730A patent/AR008394A1/es not_active Application Discontinuation
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1998
- 1998-05-29 US US09/087,089 patent/US6039881A/en not_active Expired - Lifetime
- 1998-12-11 MX MX9810585A patent/MX9810585A/es not_active Application Discontinuation
- 1998-12-18 OA OA9800244A patent/OA10943A/en unknown
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1999
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2001
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