EP2549965A2 - Procédé de préparation d'un polysaccharide contenant de l'azote - Google Patents
Procédé de préparation d'un polysaccharide contenant de l'azoteInfo
- Publication number
- EP2549965A2 EP2549965A2 EP11712745A EP11712745A EP2549965A2 EP 2549965 A2 EP2549965 A2 EP 2549965A2 EP 11712745 A EP11712745 A EP 11712745A EP 11712745 A EP11712745 A EP 11712745A EP 2549965 A2 EP2549965 A2 EP 2549965A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- cellulose
- salt
- polysaccharide
- amide
- mixture
- 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.)
- Withdrawn
Links
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 44
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 43
- -1 nitrogen-containing polysaccharide Chemical class 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 claims abstract description 55
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 150000004676 glycans Chemical class 0.000 claims abstract description 30
- 150000001408 amides Chemical class 0.000 claims abstract description 21
- 229920005862 polyol Polymers 0.000 claims abstract description 20
- 150000003077 polyols Chemical class 0.000 claims abstract description 20
- 229920002678 cellulose Polymers 0.000 claims description 93
- 239000001913 cellulose Substances 0.000 claims description 91
- 238000000034 method Methods 0.000 claims description 59
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 41
- 230000008569 process Effects 0.000 claims description 33
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 24
- 239000004202 carbamide Substances 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 19
- 239000004753 textile Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 238000001125 extrusion Methods 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 238000003825 pressing Methods 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 239000003463 adsorbent Substances 0.000 claims description 2
- 210000001124 body fluid Anatomy 0.000 claims description 2
- 239000010839 body fluid Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 238000007493 shaping process Methods 0.000 claims description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
- 235000010980 cellulose Nutrition 0.000 description 91
- 230000008961 swelling Effects 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- 239000000243 solution Substances 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 23
- 229920000642 polymer Polymers 0.000 description 22
- 239000002904 solvent Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000835 fiber Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000004090 dissolution Methods 0.000 description 9
- 229920000297 Rayon Polymers 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 238000001212 derivatisation Methods 0.000 description 7
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 6
- 230000008929 regeneration Effects 0.000 description 6
- 238000011069 regeneration method Methods 0.000 description 6
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000002608 ionic liquid Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000006184 cosolvent Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000004627 regenerated cellulose Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000004483 ATR-FTIR spectroscopy Methods 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000012991 xanthate Substances 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 229920000433 Lyocell Polymers 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 150000002772 monosaccharides Chemical group 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- 150000003567 thiocyanates Chemical class 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BSKSXTBYXTZWFI-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;acetate Chemical compound CC([O-])=O.CCCC[N+]=1C=CN(C)C=1 BSKSXTBYXTZWFI-UHFFFAOYSA-M 0.000 description 1
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 1
- ABFDKXBSQCTIKH-UHFFFAOYSA-M 1-ethylpyridin-1-ium;bromide Chemical compound [Br-].CC[N+]1=CC=CC=C1 ABFDKXBSQCTIKH-UHFFFAOYSA-M 0.000 description 1
- KBPZVLXARDTGGD-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;iron Chemical compound [Fe].OC(=O)C(O)C(O)C(O)=O KBPZVLXARDTGGD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical class OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229920002749 Bacterial cellulose Polymers 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 229920000875 Dissolving pulp Polymers 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- DBNPDRYVYQWGFW-UHFFFAOYSA-N N.[Cu]=O Chemical compound N.[Cu]=O DBNPDRYVYQWGFW-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920011250 Polypropylene Block Copolymer Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000005016 bacterial cellulose Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001720 carbohydrates Chemical class 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
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical class CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000007483 microbial process Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 238000013386 optimize process Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
- C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/16—Halogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/205—Compounds containing groups, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/21—Urea; Derivatives thereof, e.g. biuret
Definitions
- the degree of substitution is the number of hydroxyl groups substituted by carbamate per monosaccharide unit.
- the DS can vary and reach at most the number of OH groups per monosaccharide unit.
- the maximum DS 3.
- a suitable and sufficient DS for the present invention depends on the mode of application and can be changed by selecting the saccharide substrate and the reaction temperature and reaction time.
- the derivatizing melt thus produced can now be processed into shaped articles by the usual methods, e.g. by extrusion through nozzles or dissolution of the cellulosecarbamat conceptionigen polymer in sodium hydroxide solution and precipitation in an aqueous precipitation bath. If the cellulose carbamate solution is introduced directly into an aqueous solution, cellulose carbamate in amorphous form is obtained.
- the deformation of the materials takes place by the action of heat and pressure.
- the material samples described below were treated at a pressure of around 1.0 bar for a period of 30 seconds to 2 minutes at temperatures of 150 ° C to 220 ° C.
- the formation of the cellulose carbamate can be confirmed on the basis of the N content and the IR spectrum, wherein the nitrogen content increases with the use of said formulations with increasing treatment temperature and treatment time up to about 2 wt.% N from the weight of the material.
- N about 1% by weight of N is obtained after treatment at 190 ° C. for 2 minutes or 220 ° C. for 30 seconds; for a treatment at 220 ° C. for 2 minutes, formulations 1 1, 6 Wt.% N and in formulation 3 2.0 wt.% N bound in the polymer (this corresponds to a degree of substitution DS of 0.2-0.25).
- Fig. 2 shows the nitrogen content in wt.% Of the treated cellulose
- the treating solution was prepared by mixing polyethylene glycol (20% by weight), urea (60% by weight) and sodium acetate (20% by weight). The molecular weight of polyethylene glycol was varied from 4000 to 6000 from 2000. A sufficient amount of deionized water was added. Viscose fabric stored under standard conditions (20 +/- 2 ° C, 65 + 1-2% RH) for at least 48 hours was impregnated with a pad at the above solution at room temperature under 1 bar pressure at a speed of 1 m / min. Thereafter, the textile was dried in a tenter dryer at 105 ° C for 40 seconds to remove water. Thereafter, the dried textile was treated at 1 bar pressure for 2 min at 100 ° C to 250 ° C.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
L'invention concerne un mélange de substances contenant de 10 à 80 % en poids d'au moins un amide, de 10 à 80 % en poids d'au moins un sel et de 1 à 80 % en poids d'au moins un polyol. Elle concerne en outre l'utilisation de ce mélange de substances pour préparer un polysaccharide contenant de l'azote à partir d'un polysaccharide, ainsi que diverses utilisations des produits ainsi fabriqués.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT4642010A AT509621B1 (de) | 2010-03-23 | 2010-03-23 | Verfahren zur herstellung eines stickstoffenthaltenden polysaccharids |
| PCT/AT2011/000141 WO2011116403A2 (fr) | 2010-03-23 | 2011-03-22 | Procédé de préparation d'un polysaccharide contenant de l'azote |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2549965A2 true EP2549965A2 (fr) | 2013-01-30 |
Family
ID=44115745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP11712745A Withdrawn EP2549965A2 (fr) | 2010-03-23 | 2011-03-22 | Procédé de préparation d'un polysaccharide contenant de l'azote |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP2549965A2 (fr) |
| AT (1) | AT509621B1 (fr) |
| WO (1) | WO2011116403A2 (fr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU810735A1 (ru) | 1979-05-03 | 1981-03-07 | Ленинградский Технологическийинститут Целлюлозно-Бумажной Про-Мышленности | Растворитель целлюлозы и способЕЕ РАСТВОРЕНи |
| FI62318C (fi) | 1981-01-27 | 1982-12-10 | Neste Oy | Foerfarande foer framstaellning av ett alkaliloesligt cellulosaderivat |
| DD214622A1 (de) | 1983-03-18 | 1984-10-17 | Tu Dresden Sektion Chemie | Verfahren zur herstellung spinnfaehiger celluloseloesungen |
| US4789006A (en) | 1987-03-13 | 1988-12-06 | Teepak, Inc. | Cellulose aminomethanate sausage casings |
| US4999425A (en) | 1989-06-12 | 1991-03-12 | Teepak, Inc. | Cellulose aminomethanate by ion-exchange extraction |
| PL160866B1 (pl) | 1989-09-07 | 1993-04-30 | Inst Wlokien Chem | Sposób wytwarzania karbamlnlanu celulozy |
| PL163049B1 (pl) | 1990-03-26 | 1994-02-28 | Inst Wlokien Chem | Sposób wytwarzania karbaminianu celulozy |
| DE4120857A1 (de) | 1991-06-25 | 1993-01-07 | Hilti Ag | Spreizduebel |
| DE4242437C2 (de) | 1992-12-16 | 1998-08-13 | Zimmer Ag | Verfahren zur Herstellung von Cellulosecarbamat und Verwendung des erhaltenen Cellulosecarbamats zur Bildung einer Lösung für die Herstellung von Celluloseregenerat-Produkten |
| DE4407906C1 (de) | 1994-03-09 | 1995-07-27 | Fraunhofer Ges Forschung | Verfahren zur Herstellung von Cellulosecarbamat |
| DE19635473A1 (de) | 1996-08-31 | 1998-03-05 | Zimmer Ag | Verfahren zur Herstellung von Cellulosecarbamat mit verbesserten Löseeigenschaften |
| DE19635707C1 (de) | 1996-09-03 | 1998-04-02 | Inst Textil & Faserforschung | Verfahren zur Herstellung von Cellulosecarbamat |
| DE19940393C1 (de) | 1999-08-25 | 2001-03-22 | Fraunhofer Ges Forschung | Verfahren zur Herstellung von alkalilöslichem Cellulosecarbamat |
| JP2002080401A (ja) * | 2000-06-21 | 2002-03-19 | Nof Corp | ゲル状外用剤組成物 |
| DE10162791C1 (de) | 2001-12-20 | 2002-12-19 | Fraunhofer Ges Forschung | Verfahren zur Herstellung von Cellulosecarbamat |
| DE10223171A1 (de) * | 2002-05-24 | 2003-12-11 | Zimmer Ag | Verfahren zur Herstellung von Cellulosecarbamat |
| DE10223172B4 (de) * | 2002-05-24 | 2004-05-06 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur Herstellung von Cellulosecarbamat mittels reaktiver Extrusion und die Verwendung der Verfahrensprodukte zur Herstellung von Formkörpern |
| DE10223174A1 (de) | 2002-05-24 | 2003-12-11 | Fraunhofer Ges Forschung | Verfahren zur Herstellung von Cellulosecarbamatformkörpern |
| DE10253672B3 (de) | 2002-11-18 | 2004-02-12 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur Herstellung von Cellulosecarbamat in einem inerten organischen, mit Wasser nicht mischbaren Lösungsmittel |
| DE10341952B4 (de) * | 2003-09-11 | 2008-11-20 | Lurgi Gmbh | Zwischenprodukt bestehend aus einer Mischung von organischen Carbonaten und Carbamaten und ein Verfahren zu seiner Herstellung |
| CN1322012C (zh) | 2005-04-26 | 2007-06-20 | 中国科学院新疆理化技术研究所 | 尿素嵌入法制备纤维素氨基甲酸酯的方法 |
| EP1887354B1 (fr) * | 2005-05-09 | 2015-04-01 | National University Corporation Nagoya University | Procédé pour la production d'une bille pour la résolution d'isomères optiques |
| CN100427508C (zh) | 2005-10-27 | 2008-10-22 | 东华大学 | 利用超临界二氧化碳制备纤维素氨基甲酸酯的方法 |
| FI20065350A7 (fi) * | 2006-05-24 | 2007-11-25 | Scitech Service Oy | Antimikrobinen polymeerimateriaali ja sen käyttö |
| CN101265337A (zh) * | 2008-04-10 | 2008-09-17 | 深圳市富易达电子科技有限公司 | 一种具有优良离子传导性的隔膜的制备方法 |
| CN101353181A (zh) * | 2008-08-07 | 2009-01-28 | 上海交通大学 | 亲水性单分散羧基超顺磁微球的合成方法 |
| CN101525487B (zh) * | 2009-03-31 | 2012-01-11 | 武汉华丽生物材料有限公司 | 一种可环境降解的复合材料及其制备方法 |
| CN101597336A (zh) | 2009-07-03 | 2009-12-09 | 武汉大学 | 纤维素氨基甲酸酯的微波合成方法 |
-
2010
- 2010-03-23 AT AT4642010A patent/AT509621B1/de not_active IP Right Cessation
-
2011
- 2011-03-22 EP EP11712745A patent/EP2549965A2/fr not_active Withdrawn
- 2011-03-22 WO PCT/AT2011/000141 patent/WO2011116403A2/fr not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2011116403A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AT509621B1 (de) | 2012-04-15 |
| WO2011116403A2 (fr) | 2011-09-29 |
| AT509621A1 (de) | 2011-10-15 |
| WO2011116403A3 (fr) | 2011-11-24 |
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