CA1122209A - Crosslinked polymeric substance - Google Patents
Crosslinked polymeric substanceInfo
- Publication number
- CA1122209A CA1122209A CA000348930A CA348930A CA1122209A CA 1122209 A CA1122209 A CA 1122209A CA 000348930 A CA000348930 A CA 000348930A CA 348930 A CA348930 A CA 348930A CA 1122209 A CA1122209 A CA 1122209A
- Authority
- CA
- Canada
- Prior art keywords
- chitin
- polymeric substance
- crosslinked polymeric
- degree
- crosslinked
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000126 substance Substances 0.000 title claims abstract description 41
- 229920002101 Chitin Polymers 0.000 claims abstract description 59
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 238000004132 cross linking Methods 0.000 claims description 19
- 238000006640 acetylation reaction Methods 0.000 claims description 12
- 238000006467 substitution reaction Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- QWVCIORZLNBIIC-UHFFFAOYSA-N 2,3-dibromopropan-1-ol Chemical compound OCC(Br)CBr QWVCIORZLNBIIC-UHFFFAOYSA-N 0.000 claims description 2
- GIFYLSXAYQQOAU-UHFFFAOYSA-N 2,3-dibromopropane-1-thiol Chemical compound SCC(Br)CBr GIFYLSXAYQQOAU-UHFFFAOYSA-N 0.000 claims description 2
- OCMDEHWOXQGQOZ-UHFFFAOYSA-N 2,5-dibromopentan-1-ol Chemical compound OCC(Br)CCCBr OCMDEHWOXQGQOZ-UHFFFAOYSA-N 0.000 claims description 2
- PXESMAOTBGZAIZ-UHFFFAOYSA-N 2,5-dibromopentane-1-thiol Chemical compound SCC(Br)CCCBr PXESMAOTBGZAIZ-UHFFFAOYSA-N 0.000 claims description 2
- ZRRZAIJKJYIGIV-UHFFFAOYSA-N 2-(3-bromopropyl)oxirane Chemical compound BrCCCC1CO1 ZRRZAIJKJYIGIV-UHFFFAOYSA-N 0.000 claims description 2
- PTPMSMVSPQLTOU-UHFFFAOYSA-N 2-(3-bromopropyl)thiirane Chemical compound BrCCCC1CS1 PTPMSMVSPQLTOU-UHFFFAOYSA-N 0.000 claims description 2
- VTFRCOGCPHVIHW-UHFFFAOYSA-N 2-(bromomethyl)thiirane Chemical compound BrCC1CS1 VTFRCOGCPHVIHW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003463 adsorbent Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- OSXSWVHSLRHTHZ-UHFFFAOYSA-N 2,4-dibromobutan-1-ol Chemical compound OCC(Br)CCBr OSXSWVHSLRHTHZ-UHFFFAOYSA-N 0.000 claims 1
- RGMCQAFLVVGKMM-UHFFFAOYSA-N 2,4-dibromobutane-1-thiol Chemical compound SCC(Br)CCBr RGMCQAFLVVGKMM-UHFFFAOYSA-N 0.000 claims 1
- ZKODPGZNBMIZFX-UHFFFAOYSA-N 2-(2-bromoethyl)oxirane Chemical compound BrCCC1CO1 ZKODPGZNBMIZFX-UHFFFAOYSA-N 0.000 claims 1
- RXDOURUYCDFWDE-UHFFFAOYSA-N 2-(2-bromoethyl)thiirane Chemical compound BrCCC1CS1 RXDOURUYCDFWDE-UHFFFAOYSA-N 0.000 claims 1
- XRWMHJJHPQTTLQ-UHFFFAOYSA-N 2-(chloromethyl)thiirane Chemical compound ClCC1CS1 XRWMHJJHPQTTLQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000047 product Substances 0.000 description 28
- 239000003513 alkali Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 108010088751 Albumins Proteins 0.000 description 9
- 102000009027 Albumins Human genes 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 239000000499 gel Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000005341 cation exchange Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000007710 freezing Methods 0.000 description 4
- 230000008014 freezing Effects 0.000 description 4
- 108010074605 gamma-Globulins Proteins 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000009938 salting Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 108010049003 Fibrinogen Proteins 0.000 description 3
- 102000008946 Fibrinogen Human genes 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000005349 anion exchange Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229940098773 bovine serum albumin Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- 229940012952 fibrinogen Drugs 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229950006780 n-acetylglucosamine Drugs 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 2
- IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 2
- -1 N-acetyl D-glucosamines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- ZXKFFOMHVCMTEV-UHFFFAOYSA-N 2-ethylthiirane Chemical compound CCC1CS1 ZXKFFOMHVCMTEV-UHFFFAOYSA-N 0.000 description 1
- DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-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
- GRHQDJDRGZFIPO-UHFFFAOYSA-N 4-bromobutanoic acid Chemical compound OC(=O)CCCBr GRHQDJDRGZFIPO-UHFFFAOYSA-N 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 102100025597 Caspase-4 Human genes 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 101100273284 Homo sapiens CASP4 gene Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical class CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 239000012888 bovine serum Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Chemical class 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000012460 protein solution Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/08—Polysaccharides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4181279A JPS55134646A (en) | 1979-04-06 | 1979-04-06 | Amphoteric ion exchanger |
| JP41812/79 | 1979-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1122209A true CA1122209A (en) | 1982-04-20 |
Family
ID=12618718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000348930A Expired CA1122209A (en) | 1979-04-06 | 1980-04-01 | Crosslinked polymeric substance |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US4373096A (en]) |
| EP (1) | EP0018131B1 (en]) |
| JP (1) | JPS55134646A (en]) |
| CA (1) | CA1122209A (en]) |
| DE (1) | DE3061737D1 (en]) |
| DK (1) | DK147880A (en]) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637681A (en) * | 1992-08-19 | 1997-06-10 | Stockel; Richard F. | Aminosaccharide biguanides |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4536207A (en) * | 1983-07-26 | 1985-08-20 | Igi Biotechnology, Inc. | Nematocidally active chitin-protein complex |
| US4863907A (en) * | 1984-06-29 | 1989-09-05 | Seikagaku Kogyo Co., Ltd. | Crosslinked glycosaminoglycans and their use |
| WO1986004586A1 (en) * | 1985-02-08 | 1986-08-14 | Igi Biotechnology, Inc. | Nematocidally active chitin-protein complex |
| JPS6270401A (ja) * | 1985-09-24 | 1987-03-31 | Fuji Boseki Kk | カルボキシアルキルキトサン粒状体の製造方法 |
| SE452469B (sv) * | 1986-06-18 | 1987-11-30 | Pharmacia Ab | Material bestaende av en tverbunden karboxylgrupphaltig polysackarid och forfarande vid framstellning av detsamma |
| DE3644097A1 (de) * | 1986-12-23 | 1988-07-07 | Wella Ag | Kosmetisches mittel auf der basis von chitosan und ampholytischen copolymerisaten sowie ein neues chitosan/polyampholyt-salz |
| DE3830365C2 (de) * | 1988-09-07 | 1996-06-27 | Metallgesellschaft Ag | Verwendung von ferritischen Chrom - Molybdän-Stählen als gegen konzentrierte Schwefelsäure beständigem Werkstoff |
| US5169535A (en) * | 1989-09-22 | 1992-12-08 | Kurita Water Industries Ltd. | Method of removing endotoxin |
| CA2072918A1 (en) * | 1992-02-14 | 1993-08-15 | Jian Qin | Modified polysaccharides having improved absorbent properties and process for the preparation thereof |
| US5550189A (en) * | 1992-04-17 | 1996-08-27 | Kimberly-Clark Corporation | Modified polysaccharides having improved absorbent properties and process for the preparation thereof |
| US5599916A (en) * | 1994-12-22 | 1997-02-04 | Kimberly-Clark Corporation | Chitosan salts having improved absorbent properties and process for the preparation thereof |
| US5498705A (en) * | 1995-02-22 | 1996-03-12 | Kimberly-Clark Corporation | Modified polysaccharides having improved absorbent properties and process for the preparation thereof |
| JP4124483B2 (ja) * | 1996-05-09 | 2008-07-23 | 大正製薬株式会社 | ミセル様水性組成物及び疎水性薬物の可溶化方法 |
| KR100477891B1 (ko) * | 2002-07-19 | 2005-03-18 | 한국화학연구원 | 다당류를 이용한 키랄성 분리막 |
| FR3016882A1 (fr) | 2014-01-30 | 2015-07-31 | Sofradim Production | Procede de preparation de chitosane a haut degre d’acetylation |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2168375A (en) * | 1936-07-09 | 1939-08-08 | Visking Corp | Chitin xanthate |
| DE858696C (de) * | 1943-05-13 | 1952-12-08 | Henkel & Cie Gmbh | Verfahren zur Herstellung von AEther des Chitosans enthaltenden Erzeugnissen |
| US3251824A (en) * | 1961-08-22 | 1966-05-17 | Fmc Corp | Method of preparing stable aqueous dispersion-forming cellulosic aggregates |
| US4076930A (en) * | 1968-12-13 | 1978-02-28 | James Ellingboe | Polysaccharide polyols |
| US4027068A (en) * | 1975-09-12 | 1977-05-31 | American Cyanamid Company | Use of chitin derivatives in automobile products |
| JPS596695B2 (ja) * | 1976-06-30 | 1984-02-14 | 積水化学工業株式会社 | 吸着剤 |
| US4119619A (en) * | 1976-12-16 | 1978-10-10 | Sergei Vasilievich Rogozhin | Emulsification method for the processing of kriel to produce protein, lipids and chitin |
| JPS53161389U (en]) * | 1977-05-25 | 1978-12-18 | ||
| JPS53161391U (en]) * | 1977-05-26 | 1978-12-18 | ||
| US4308377A (en) * | 1978-12-29 | 1981-12-29 | Kureha Kagaku Kogyo Kabushiki Kaisha | Shaped material comprising denatured chitin and process for preparing same |
-
1979
- 1979-04-06 JP JP4181279A patent/JPS55134646A/ja active Granted
-
1980
- 1980-03-24 US US06/132,787 patent/US4373096A/en not_active Expired - Lifetime
- 1980-04-01 CA CA000348930A patent/CA1122209A/en not_active Expired
- 1980-04-01 DE DE8080301032T patent/DE3061737D1/de not_active Expired
- 1980-04-01 EP EP80301032A patent/EP0018131B1/en not_active Expired
- 1980-04-02 DK DK147880A patent/DK147880A/da not_active Application Discontinuation
-
1982
- 1982-06-22 US US06/390,832 patent/US4493928A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637681A (en) * | 1992-08-19 | 1997-06-10 | Stockel; Richard F. | Aminosaccharide biguanides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55134646A (en) | 1980-10-20 |
| DK147880A (da) | 1980-10-07 |
| US4373096A (en) | 1983-02-08 |
| EP0018131A1 (en) | 1980-10-29 |
| JPS6219897B2 (en]) | 1987-05-01 |
| US4493928A (en) | 1985-01-15 |
| EP0018131B1 (en) | 1983-01-26 |
| DE3061737D1 (en) | 1983-03-03 |
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