SK128597A3 - Process for activating polysaccharides, polysaccharides produced by this process, and use thereof - Google Patents
Process for activating polysaccharides, polysaccharides produced by this process, and use thereof Download PDFInfo
- Publication number
- SK128597A3 SK128597A3 SK1285-97A SK128597A SK128597A3 SK 128597 A3 SK128597 A3 SK 128597A3 SK 128597 A SK128597 A SK 128597A SK 128597 A3 SK128597 A3 SK 128597A3
- Authority
- SK
- Slovakia
- Prior art keywords
- cellulose
- polysaccharide
- ammonia
- pressure
- liquid ammonia
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 69
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 57
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 57
- 230000008569 process Effects 0.000 title claims abstract description 31
- 230000003213 activating effect Effects 0.000 title claims abstract description 9
- 150000004676 glycans Chemical class 0.000 title claims abstract 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 187
- 229920002678 cellulose Polymers 0.000 claims abstract description 80
- 239000001913 cellulose Substances 0.000 claims abstract description 79
- 229920002907 Guar gum Polymers 0.000 claims abstract description 15
- 239000000665 guar gum Substances 0.000 claims abstract description 15
- 235000010417 guar gum Nutrition 0.000 claims abstract description 15
- 229960002154 guar gum Drugs 0.000 claims abstract description 15
- 229920002101 Chitin Polymers 0.000 claims abstract description 13
- 238000006884 silylation reaction Methods 0.000 claims abstract description 9
- 230000010933 acylation Effects 0.000 claims abstract description 7
- 238000005917 acylation reaction Methods 0.000 claims abstract description 7
- 229920002472 Starch Polymers 0.000 claims abstract description 5
- 230000029936 alkylation Effects 0.000 claims abstract description 5
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 5
- 239000008107 starch Substances 0.000 claims abstract description 5
- 235000019698 starch Nutrition 0.000 claims abstract description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- 239000000463 material Substances 0.000 claims description 39
- 239000002360 explosive Substances 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 7
- 229920001131 Pulp (paper) Polymers 0.000 claims description 5
- 238000002441 X-ray diffraction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920000926 Galactomannan Polymers 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 230000021235 carbamoylation Effects 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 claims 2
- 238000002166 wet spinning Methods 0.000 claims 1
- 235000010980 cellulose Nutrition 0.000 abstract description 67
- 238000004880 explosion Methods 0.000 abstract description 24
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 230000009257 reactivity Effects 0.000 abstract description 6
- 239000007858 starting material Substances 0.000 abstract description 5
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 150000004804 polysaccharides Chemical class 0.000 description 37
- 239000000047 product Substances 0.000 description 26
- 230000000694 effects Effects 0.000 description 14
- 238000001994 activation Methods 0.000 description 13
- 238000001212 derivatisation Methods 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 230000004913 activation Effects 0.000 description 12
- 239000000835 fiber Substances 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 230000008961 swelling Effects 0.000 description 8
- 239000004753 textile Substances 0.000 description 8
- 238000002083 X-ray spectrum Methods 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 229920005610 lignin Polymers 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229920002488 Hemicellulose Polymers 0.000 description 6
- 238000006640 acetylation reaction Methods 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 6
- 210000003746 feather Anatomy 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002028 Biomass Substances 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 230000021736 acetylation Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 229920003043 Cellulose fiber Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000012978 lignocellulosic material Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000013074 reference sample Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920001661 Chitosan Polymers 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 1
- 239000004593 Epoxy Chemical class 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920001202 Inulin Polymers 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000005280 amorphization Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229940075894 denatured ethanol Drugs 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 description 1
- 229940029339 inulin Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/02—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from solutions of cellulose in acids, bases or salts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B1/00—Preparatory treatment of cellulose for making derivatives thereof, e.g. pre-treatment, pre-soaking, activation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B1/00—Preparatory treatment of cellulose for making derivatives thereof, e.g. pre-treatment, pre-soaking, activation
- C08B1/06—Rendering cellulose suitable for etherification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B30/00—Preparation of starch, degraded or non-chemically modified starch, amylose, or amylopectin
- C08B30/12—Degraded, destructured or non-chemically modified starch, e.g. mechanically, enzymatically or by irradiation; Bleaching of starch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0087—Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
- C08B37/0096—Guar, guar gum, guar flour, guaran, i.e. (beta-1,4) linked D-mannose units in the main chain branched with D-galactose units in (alpha-1,6), e.g. from Cyamopsis Tetragonolobus; Derivatives thereof
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/24—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Emergency Medicine (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511061 | 1995-03-25 | ||
| PCT/EP1996/001274 WO1996030411A1 (fr) | 1995-03-25 | 1996-03-22 | Procede permettant d'activer des polysaccharides, polysaccharides obtenus selon ledit procede et leur utilisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK128597A3 true SK128597A3 (en) | 1998-03-04 |
Family
ID=7757778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1285-97A SK128597A3 (en) | 1995-03-25 | 1996-03-22 | Process for activating polysaccharides, polysaccharides produced by this process, and use thereof |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5939544A (fr) |
| EP (1) | EP0817803B1 (fr) |
| JP (2) | JP3390015B2 (fr) |
| KR (1) | KR100254840B1 (fr) |
| CN (1) | CN1083454C (fr) |
| AT (1) | ATE181338T1 (fr) |
| AU (1) | AU695331B2 (fr) |
| BG (1) | BG62778B1 (fr) |
| BR (1) | BR9607992A (fr) |
| CA (1) | CA2214245C (fr) |
| CZ (1) | CZ284387B6 (fr) |
| DE (2) | DE19611416A1 (fr) |
| EA (1) | EA000169B1 (fr) |
| ES (1) | ES2135221T3 (fr) |
| HU (1) | HUP9802337A3 (fr) |
| PL (1) | PL322468A1 (fr) |
| RO (1) | RO115053B1 (fr) |
| SK (1) | SK128597A3 (fr) |
| WO (1) | WO1996030411A1 (fr) |
| ZA (1) | ZA962370B (fr) |
Families Citing this family (80)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19628277C2 (de) * | 1996-07-12 | 1998-07-09 | Rhodia Ag Rhone Poulenc | Verfahren zur Aktivierung eines Cellulose und Harnstoff enthaltenden Gemisches, aktiviertes Cellulose und Harnstoff enthaltendes Gemisch und Verwendung des aktivierten Gemisches zur Herstellung von Cellulosecarbamat |
| DE19654251A1 (de) * | 1996-12-23 | 1998-06-25 | Rhodia Ag Rhone Poulenc | Verfahren zur Isolierung von Guaran aus Guar-Endosperm |
| DE19742692A1 (de) * | 1997-09-26 | 1999-04-01 | Rhodia Acetow Ag | Verfahren zur Aktivierung von Polysacchariden |
| FR2770232B1 (fr) * | 1997-10-27 | 2000-01-14 | Rhodia Ag Rhone Poulenc | Procede de preparation d'une fibre ou d'un fil de cellulose regeneree |
| DE19810740A1 (de) * | 1998-03-13 | 1999-09-16 | Rhodia Acetow Ag | Verfahren zur Dosierung eines Ammoniak/Zusatzstoff-Systems in einen Feststoff und Dosiervorrichtung |
| EP1066109A1 (fr) * | 1998-03-13 | 2001-01-10 | Rhodia Acetow GmbH | Dispositif, procede et reacteur pressurise permettant de traiter des matieres solides avec un gaz liquide sous pression |
| DE19814137A1 (de) * | 1998-03-30 | 1999-10-14 | Rhodia Acetow Ag | Verfahren zum Austreiben von Ammoniak aus einem aktivierten Polysaccharid |
| DE19921755A1 (de) * | 1999-05-11 | 2000-11-16 | Rhodia Acetow Ag | Verfahren zur Herstellung einer Spinnlösung von Zellstoff in N-Methylmorpholin-N-oxid-Monohydrat, die damit erhältlichen Lösungen sowie die daraus durch Verspinnen erhältlichen Regeneratcellulosefasern |
| DE10132366A1 (de) * | 2001-07-04 | 2003-01-30 | Degussa | Verfahren zur physikalischen Behandlung von Stärke(-Derivaten) |
| WO2004053004A1 (fr) * | 2002-12-06 | 2004-06-24 | Polaroid Corporation | Inscriptions d'indication a immersion dans l'eau et articles portant de telles inscriptions |
| US6881252B2 (en) | 2003-09-23 | 2005-04-19 | Corn Products International, Inc. | Fiber-based product |
| CA2640429C (fr) * | 2006-01-27 | 2014-04-01 | University Of Massachusetts | Systemes et procedes d'obtention de biocarburants et substances connexes |
| WO2008020901A2 (fr) * | 2006-05-01 | 2008-02-21 | Michigan State University | Séparation de protéines à partir d'herbes intégrées avec un prétraitement d'explosion des fibres à l'ammoniac (afex) et une hydrolyse de la cellulose |
| US20110201091A1 (en) * | 2007-08-29 | 2011-08-18 | Board Of Trustees Of Michigan State University | Production of microbial growth stimulant with ammonia fiber explosion (AFEX) pretreatment and cellulose hydrolysis |
| US9206446B2 (en) * | 2006-05-01 | 2015-12-08 | Board Of Trustees Of Michigan State University | Extraction of solubles from plant biomass for use as microbial growth stimulant and methods related thereto |
| US8968515B2 (en) | 2006-05-01 | 2015-03-03 | Board Of Trustees Of Michigan State University | Methods for pretreating biomass |
| WO2007130337A1 (fr) | 2006-05-01 | 2007-11-15 | Michigan State University | Procédé de traitement d'une biomasse lignocellulosique |
| EP2047030B2 (fr) † | 2006-06-14 | 2014-04-09 | Sappi Manufacturing (PTY) Ltd | Amélioration de la réactivité de la pâte de cellulose |
| US20090281303A1 (en) * | 2006-06-23 | 2009-11-12 | Basf Se | Process for silylating cellulose |
| US9499635B2 (en) | 2006-10-13 | 2016-11-22 | Sweetwater Energy, Inc. | Integrated wood processing and sugar production |
| US8323923B1 (en) | 2006-10-13 | 2012-12-04 | Sweetwater Energy, Inc. | Method and system for producing ethanol |
| US7670813B2 (en) * | 2006-10-25 | 2010-03-02 | Iogen Energy Corporation | Inorganic salt recovery during processing of lignocellulosic feedstocks |
| US8247200B2 (en) * | 2007-01-25 | 2012-08-21 | Iogen Energy Corporation | Method of obtaining inorganic salt and acetate salt from cellulosic biomass |
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| WO2008137639A1 (fr) * | 2007-05-02 | 2008-11-13 | Mascoma Corporation | Procédé de prétraitement en deux étapes de biomasse lignocellulosique |
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| US20090011474A1 (en) * | 2007-06-20 | 2009-01-08 | Board Of Trustees Of Michigan State University | Process for producing sugars from cellulosic biomass |
| US20090042259A1 (en) * | 2007-08-09 | 2009-02-12 | Board Of Trustees Of Michigan State University | Process for enzymatically converting a plant biomass |
| US20090053771A1 (en) * | 2007-08-22 | 2009-02-26 | Board Of Trustees Of Michigan State University | Process for making fuels and chemicals from AFEX-treated whole grain or whole plants |
| US8192968B2 (en) | 2007-08-27 | 2012-06-05 | Iogen Energy Corporation | Method for the production of a fermentation product from a pretreated lignocellulosic feedstock |
| US8367378B2 (en) * | 2007-10-03 | 2013-02-05 | Board Of Trustees Of Michigan State University | Process for producing sugars and ethanol using corn stillage |
| EP2257632A1 (fr) * | 2008-02-27 | 2010-12-08 | Qteros, Inc. | Procédés pour la conversion de substances végétales en carburants et en produits chimiques par l action séquentielle de deux microorganismes |
| WO2009124321A1 (fr) * | 2008-04-04 | 2009-10-08 | University Of Massachusetts | Procédés et compositions pour améliorer la production de combustibles dans les microorganismes |
| US20100105114A1 (en) * | 2008-06-11 | 2010-04-29 | University Of Massachusetts | Methods and Compositions for Regulating Sporulation |
| US8529765B2 (en) * | 2008-12-09 | 2013-09-10 | Sweetwater Energy, Inc. | Ensiling biomass for biofuels production and multiple phase apparatus for hydrolyzation of ensiled biomass |
| US9279112B2 (en) | 2009-02-27 | 2016-03-08 | Iogen Energy Corporation | Cellulase enzymes having a modified linker and reduced lignin binding |
| US20100086981A1 (en) * | 2009-06-29 | 2010-04-08 | Qteros, Inc. | Compositions and methods for improved saccharification of biomass |
| WO2010123932A1 (fr) * | 2009-04-20 | 2010-10-28 | Qteros, Inc. | Compositions et procédés pour la fermentation d'une biomasse |
| US8945245B2 (en) | 2009-08-24 | 2015-02-03 | The Michigan Biotechnology Institute | Methods of hydrolyzing pretreated densified biomass particulates and systems related thereto |
| US10457810B2 (en) | 2009-08-24 | 2019-10-29 | Board Of Trustees Of Michigan State University | Densified biomass products containing pretreated biomass fibers |
| BRPI1007699B8 (pt) | 2009-08-24 | 2021-03-23 | Univ Michigan State | produto, produto embalado e processo |
| US20110183382A1 (en) * | 2009-12-15 | 2011-07-28 | Qteros, Inc. | Methods and compositions for producing chemical products from c. phytofermentans |
| BR122022002136B1 (pt) * | 2009-12-17 | 2022-08-23 | Fina Biosolutions, Llc | Processo de conjugação de carboidratos na preparação de vacinas conjugadas e suas respectivas vacinas |
| WO2011097713A1 (fr) | 2010-02-11 | 2011-08-18 | Iogen Energy Corporation | Modules de liaison de glucide avec une liaison réduite à la lignine |
| GB2478791A (en) * | 2010-03-19 | 2011-09-21 | Qteros Inc | Ethanol production by genetically-modified bacteria |
| AU2011242896C1 (en) | 2010-04-19 | 2016-04-21 | Board Of Trustees Of Michigan State University | Digestible lignocellulosic biomass and extractives and methods for producing same |
| DK2606131T3 (en) | 2010-08-20 | 2017-06-19 | Codexis Inc | Use of proteins from glycoside hydrolase 61 family for cellulose processing |
| JP2012080818A (ja) * | 2010-10-12 | 2012-04-26 | Idemitsu Kosan Co Ltd | 固体バイオマスの糖化前処理方法、その装置、および、固体バイオマスの糖化方法 |
| US8236551B2 (en) | 2010-11-02 | 2012-08-07 | Codexis, Inc. | Compositions and methods for production of fermentable sugars |
| ES2604114T3 (es) | 2010-11-02 | 2017-03-03 | Codexis, Inc. | Cepas de hongos mejoradas |
| BR112014004171A2 (pt) | 2011-08-22 | 2018-11-06 | Codexis Inc | variantes da proteína glicósideo hidrolase gh61 e cofatores que aumentam a atividade de gh61 |
| EP2760997A4 (fr) | 2011-09-30 | 2015-02-11 | Codexis Inc | Protéases fongiques |
| CN103145873B (zh) * | 2011-12-06 | 2015-12-09 | 蔡敏郎 | 几丁质去乙酰化的方法 |
| US20140357727A1 (en) | 2011-12-20 | 2014-12-04 | Codexis, Inc. | Fatty alcohol forming acyl reductase (far) variants and methods of use |
| BR112014015030A2 (pt) | 2011-12-20 | 2017-06-13 | Codexis Inc | variantes da endoflucanase 1b (eg1b) |
| US8765430B2 (en) | 2012-02-10 | 2014-07-01 | Sweetwater Energy, Inc. | Enhancing fermentation of starch- and sugar-based feedstocks |
| US10202660B2 (en) | 2012-03-02 | 2019-02-12 | Board Of Trustees Of Michigan State University | Methods for increasing sugar yield with size-adjusted lignocellulosic biomass particles |
| US8563277B1 (en) | 2012-04-13 | 2013-10-22 | Sweetwater Energy, Inc. | Methods and systems for saccharification of biomass |
| WO2013155496A1 (fr) | 2012-04-13 | 2013-10-17 | Sweetwater Energy, Inc. | Procédés et systèmes pour la saccharification d'une biomasse |
| US20150133698A1 (en) | 2012-04-20 | 2015-05-14 | Codexis, Inc. | Production of fatty alcohols from engineered microorganisms |
| EP2859096A4 (fr) | 2012-06-11 | 2016-05-11 | Codexis Inc | Xylanases et xylosidases fongiques |
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| CN102976802B (zh) * | 2012-11-23 | 2014-09-03 | 山东嘉丰海洋生物科技有限公司 | 一种壳聚糖液体肥料的加工方法 |
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| WO2014143753A1 (fr) | 2013-03-15 | 2014-09-18 | Sweetwater Energy, Inc. | Purification de carbone de courants de sucre concentré issus de biomasse prétraitée |
| US9593447B2 (en) | 2013-08-20 | 2017-03-14 | Biomass Energy Enhancements, Llc | System and method using a reaction chamber to beneficiate organic-carbon-containing feedstock for downstream processes |
| US20150052805A1 (en) | 2013-08-20 | 2015-02-26 | Michael L Catto | Oxygen-Deficient Thermally Produced Processed Biochar from Beneficiated Organic-Carbon-Containing Feedstock |
| US9796940B2 (en) | 2014-06-16 | 2017-10-24 | Biomass Energy Enhancements, Llc | Processed biomass pellets from organic-carbon-containing feedstock |
| US9701918B2 (en) | 2014-06-16 | 2017-07-11 | Biomass Energy Enhancements, Llc | System of using a reaction chamber to beneficiate organic-carbon-containing feedstock for downstream processes |
| US9702548B2 (en) | 2014-06-16 | 2017-07-11 | Biomass Energy Enhancements, Llc | System for co-firing cleaned coal and beneficiated organic-carbon-containing feedstock in a coal combustion apparatus |
| US10024533B2 (en) | 2014-06-16 | 2018-07-17 | Ctp Biotechnology Llc | System and process for combusting cleaned coal and beneficiated organic-carbon-containing feedstock |
| US9683738B2 (en) | 2014-06-16 | 2017-06-20 | Biomass Energy Enhancements, Llc | System for co-firing coal and beneficiated organic-carbon-containing feedstock in a coal combustion apparatus |
| US10018355B2 (en) | 2014-06-16 | 2018-07-10 | CTP Biotechnology, LLC | System and process for combusting coal and beneficiated organic-carbon-containing feedstock |
| PT3230463T (pt) | 2014-12-09 | 2022-08-30 | Sweetwater Energy Inc | Pré-tratamento rápido |
| EP3196205A1 (fr) * | 2016-01-22 | 2017-07-26 | Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO | Éthérification de glucides à l'aide de vapeur surchauffée |
| US11299723B2 (en) | 2016-06-15 | 2022-04-12 | Codexis, Inc. | Engineered beta-glucosidases and glucosylation methods |
| WO2018106656A1 (fr) | 2016-12-06 | 2018-06-14 | Danisco Us Inc | Enzymes de lpmo tronqués et leur utilisation |
| US11821047B2 (en) | 2017-02-16 | 2023-11-21 | Apalta Patent OÜ | High pressure zone formation for pretreatment |
| BR112022012348A2 (pt) | 2019-12-22 | 2022-09-13 | Sweetwater Energy Inc | Métodos de fazer lignina especializada e produtos de lignina da biomassa |
| WO2024129311A1 (fr) * | 2022-12-15 | 2024-06-20 | Dow Global Technologies Llc | Procédé de production de cellulose silylée |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD98322A1 (fr) * | 1972-07-17 | 1973-06-12 | ||
| SU914563A1 (ru) * | 1980-04-04 | 1982-03-23 | Inst Khim Drevesiny An Latssr | Способ активации целлюлозы 1 |
| US5037663A (en) * | 1981-10-14 | 1991-08-06 | Colorado State University Research Foundation | Process for increasing the reactivity of cellulose-containing materials |
| US4600590A (en) * | 1981-10-14 | 1986-07-15 | Colorado State University Research Foundation | Method for increasing the reactivity and digestibility of cellulose with ammonia |
| DE3241720A1 (de) * | 1982-11-11 | 1984-05-17 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von celluloseethern aus mit ammoniak aktivierter cellulose |
| US5171592A (en) * | 1990-03-02 | 1992-12-15 | Afex Corporation | Biomass refining process |
| DE4329937C1 (de) * | 1993-09-04 | 1994-11-24 | Rhodia Ag Rhone Poulenc | Verfahren zur Behandlung von Cellulose zu deren Aktivierung für nachfolgende chemische Reaktionen |
-
1996
- 1996-03-22 HU HU9802337A patent/HUP9802337A3/hu unknown
- 1996-03-22 US US08/913,782 patent/US5939544A/en not_active Expired - Fee Related
- 1996-03-22 EP EP96908120A patent/EP0817803B1/fr not_active Expired - Lifetime
- 1996-03-22 RO RO97-01782A patent/RO115053B1/ro unknown
- 1996-03-22 AU AU51481/96A patent/AU695331B2/en not_active Ceased
- 1996-03-22 SK SK1285-97A patent/SK128597A3/sk unknown
- 1996-03-22 WO PCT/EP1996/001274 patent/WO1996030411A1/fr active IP Right Grant
- 1996-03-22 JP JP52890696A patent/JP3390015B2/ja not_active Expired - Fee Related
- 1996-03-22 ES ES96908120T patent/ES2135221T3/es not_active Expired - Lifetime
- 1996-03-22 AT AT96908120T patent/ATE181338T1/de not_active IP Right Cessation
- 1996-03-22 DE DE19611416A patent/DE19611416A1/de not_active Withdrawn
- 1996-03-22 CA CA002214245A patent/CA2214245C/fr not_active Expired - Fee Related
- 1996-03-22 CN CN96192823A patent/CN1083454C/zh not_active Expired - Fee Related
- 1996-03-22 EA EA970268A patent/EA000169B1/ru not_active IP Right Cessation
- 1996-03-22 CZ CZ973005A patent/CZ284387B6/cs unknown
- 1996-03-22 PL PL96322468A patent/PL322468A1/xx unknown
- 1996-03-22 KR KR1019970706698A patent/KR100254840B1/ko not_active IP Right Cessation
- 1996-03-22 BR BR9607992-4A patent/BR9607992A/pt not_active IP Right Cessation
- 1996-03-22 DE DE59602248T patent/DE59602248D1/de not_active Expired - Fee Related
- 1996-03-25 ZA ZA962370A patent/ZA962370B/xx unknown
-
1997
- 1997-09-15 BG BG101888A patent/BG62778B1/bg unknown
-
2001
- 2001-11-08 JP JP2001343847A patent/JP2002161101A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1083454C (zh) | 2002-04-24 |
| CA2214245A1 (fr) | 1996-10-03 |
| BR9607992A (pt) | 1999-11-30 |
| HUP9802337A3 (en) | 1999-03-29 |
| JP2002161101A (ja) | 2002-06-04 |
| WO1996030411A1 (fr) | 1996-10-03 |
| ATE181338T1 (de) | 1999-07-15 |
| BG62778B1 (bg) | 2000-07-31 |
| ZA962370B (en) | 1996-10-07 |
| MX9707309A (es) | 1997-11-29 |
| EA199700268A1 (ru) | 1998-02-26 |
| JPH10505130A (ja) | 1998-05-19 |
| PL322468A1 (en) | 1998-02-02 |
| KR19980703294A (ko) | 1998-10-15 |
| CN1179781A (zh) | 1998-04-22 |
| EP0817803A1 (fr) | 1998-01-14 |
| KR100254840B1 (ko) | 2000-05-01 |
| ES2135221T3 (es) | 1999-10-16 |
| BG101888A (en) | 1998-04-30 |
| HUP9802337A2 (hu) | 1999-02-01 |
| AU695331B2 (en) | 1998-08-13 |
| EP0817803B1 (fr) | 1999-06-16 |
| US5939544A (en) | 1999-08-17 |
| JP3390015B2 (ja) | 2003-03-24 |
| DE19611416A1 (de) | 1996-09-26 |
| CZ284387B6 (cs) | 1998-11-11 |
| AU5148196A (en) | 1996-10-16 |
| DE59602248D1 (de) | 1999-07-22 |
| CZ300597A3 (en) | 1997-12-17 |
| CA2214245C (fr) | 2001-10-02 |
| RO115053B1 (ro) | 1999-10-29 |
| EA000169B1 (ru) | 1998-10-29 |
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