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WO2010061454A1 - Procédé pour la production de suspension de chitine de haute pureté - Google Patents

Procédé pour la production de suspension de chitine de haute pureté Download PDF

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Publication number
WO2010061454A1
WO2010061454A1 PCT/JP2008/071545 JP2008071545W WO2010061454A1 WO 2010061454 A1 WO2010061454 A1 WO 2010061454A1 JP 2008071545 W JP2008071545 W JP 2008071545W WO 2010061454 A1 WO2010061454 A1 WO 2010061454A1
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WO
WIPO (PCT)
Prior art keywords
chitin
solution
slurry
acid
hydrated
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Ceased
Application number
PCT/JP2008/071545
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English (en)
Japanese (ja)
Inventor
清一 戸倉
久美子 西澤
富士 小寺
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Cluster Technology Co Ltd
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Cluster Technology Co Ltd
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Priority to PCT/JP2008/071545 priority Critical patent/WO2010061454A1/fr
Priority to JP2010540259A priority patent/JP4868428B2/ja
Publication of WO2010061454A1 publication Critical patent/WO2010061454A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof

Definitions

  • the present invention relates to a method for producing a high purity chitin slurry having a low content of impurities such as proteins.
  • Chitin is a natural mucopolysaccharide obtained from crustacean shells such as crabs and shrimps, insect epidermis, and bacterial cell walls such as mushrooms, and is a biological resource that exists in large quantities on the earth. Such chitin has been found to have various excellent properties such as moisture retention, physiological activity, and biocompatibility. For this reason, many studies have been made in order to utilize the excellent characteristics of chitin in the fields of fibers, films, cosmetics, foods, medicines, medical materials and the like.
  • Non-Patent Documents 5 and 6 Non-Patent Documents. 2
  • the hydrated chitin slurry can be applied to various uses without causing the problem of environmental pollution by methanol.
  • Chitin as a raw material for the hydrated chitin slurry is usually derived from the raw material, and a small amount of protein is bound as an impurity to the chitin polymer. Proteins can cause antigen-antibody reactions and cause health hazards. In particular, in the case of chitin derived from salmon, crustacean allergen (tropomyosin) remains, which may cause crustacean allergy.
  • chitin as a raw material contains chitosan (a polymer of N-acetylglucosamine and glucosamine having an acetylation degree of 50% or less) as an impurity, and has a relatively low acetylation degree and is close to chitosan. There is also low quality chitin. There are people who do not fit the constitution of chitosan, and if a large amount of chitosan is ingested, it may adversely affect the human body.
  • An object of the present invention is to provide a method for efficiently producing a hydrated chitin slurry having sufficiently low impurities such as protein and chitosan that can adversely affect the human body and improved quality and safety.
  • the present inventors have found that the above-mentioned problems can be solved by using a specific chitin as a starting material and, if necessary, performing a specific step, The present invention has been completed. That is, the present invention includes the following.
  • a chitin solution by dissolving in (B) filtering the chitin solution to remove insoluble matter; (C) Dilute the filtered chitin solution with water, and if necessary, wash the produced chitin precipitate with water or dialyze it to replace calcium ions or magnesium ions and alcohol contained in the solution with water molecules. And a step of obtaining a hydrated chitin slurry.
  • the method for producing the hydrated chitin slurry of the present invention comprises: (A) A chitin having a protein content of less than 0.14% by weight and an acetylation degree of 96% or more is dissolved in a solvent containing methyl alcohol or ethyl alcohol and a calcium halide salt or a magnesium halide salt. Obtaining a chitin solution; (B) a step of filtering the chitin solution to remove insoluble matter; and (c) diluting the chitin solution with water, and if necessary, washing the produced chitin precipitate with water to contain calcium ions or magnesium contained in the solution. Replacing ions and alcohol with water molecules to obtain a hydrated chitin slurry.
  • chitin may have any three-dimensional structure including ⁇ -type and ⁇ -type.
  • the protein content (calculated as amino acid content) in chitin as the starting material is less than 0.14% by weight, preferably 0.1% by weight or less, more preferably 0.01% by weight or less, and
  • the acetylation degree of the starting material chitin is 96% or more, preferably 97% or more, particularly preferably 98% or more.
  • the protein content (amino acid content) in the chitin is 18 amino acids (lysine, histidine, phenylalanine, leucine, isoleucine, methionine, valine, threonine, tryptophan, arginine, tyrosine, alanine, glycine, proline, glutamic acid, Serine, aspartic acid, cystine) is a value determined by measuring by an amino acid automatic analysis method and a high performance liquid chromatography method.
  • the value of the degree of acetylation of chitin is a value determined by neutralizing and titrating chitin treated with 2 mol / l hydrochloric acid with 0.1 mol / l NaOH.
  • the chitin as the starting material is preferably dried in advance at a temperature of preferably 60 ° C. or higher, more preferably 100 ° C. or higher before being dissolved in the solvent in the step (a).
  • the upper limit of drying temperature is not specifically limited, Preferably it is 200 degrees C or less, More preferably, it is 120 degrees C or less. A temperature of 80 ° C. to 100 ° C. is particularly preferable.
  • the drying time is not particularly limited, but is, for example, 1 hour to 48 hours, preferably 4 hours to 12 hours. Further, the drying is preferably performed under reduced pressure to vacuum. By drying in this way, it is possible to further reduce the amount of gel-like substance that interferes with filtration in the filtration step (b).
  • the starting chitin is preferably regenerated chitin.
  • “regenerated chitin” means that glucosamine in chitosan (degree of acetylation of 50% or less) or chitin / chitosan (degree of acetylation of about 50%) is acetylated again to form N-acetylglucosamine, and the degree of acetylation is 50 It means chitin obtained by re-acetylating glucosamine in chitin made higher than% and low-quality chitin (acetylation degree of 90% or less). Regenerated chitin can be produced, for example, by acetylating chitosan dissolved in acetic acid with acetic anhydride.
  • the starting chitin is preferably de-O-acylated.
  • the OH group is also acetylated (O-acylated) when N-acetylating chitosan, but the O-acylated chitin does not dissolve in the solvent in step (a) .
  • the O-acylated chitin is removed as an insoluble substance in the filtration step (b), and the amount of chitin in the resulting hydrated chitin slurry is reduced.
  • De-O-acylation can be performed, for example, by heating at 20 ° C. to 95 ° C. (particularly 80 ° C.) under alkaline conditions of pH 10 to pH 11 (particularly pH 11).
  • the concentration of the calcium halide salt or magnesium halide salt in the alcohol in the solvent is preferably a saturated concentration from the viewpoint of the amount of chitin dissolved.
  • the precipitated salt binds to chitin that has not yet dissolved, and not only prevents the chitin from dissolving, but also filters it.
  • step (b) a gel-like substance is formed, and filtration is hindered. Therefore, from the viewpoint of the yield of chitin and the efficiency of the filtration step (b) (filtration rate), it is preferable to adjust the concentration of the calcium halide salt or the magnesium halide salt so that these salts do not precipitate. .
  • the chitin solution is filtered to remove insoluble matters.
  • the chitin solution can be filtered without using external force at a much higher filtration rate than when conventional chitin is used.
  • the filter cloth used in the filtration step (b) those having various materials and various properties (thickness, pore diameter, pore density, etc.) can be used depending on the starting material chitin and the like.
  • the average pore diameter is preferably 0.01 to 1 mm, more preferably 0.05 to 0.5 mm, especially 0.13 mm and 0.2 mm, and / or the average mesh number is preferably 0.5.
  • Filter cloths of ⁇ 50 / mm, more preferably 1 ⁇ 10 / mm, especially 4 / mm can be used.
  • the average pore diameter is a value measured by an optical measuring device such as a microscope or a microscope.
  • the average number of meshes (pieces / mm) indicates the average value of the number of meshes (holes) existing per 1 mm length of the filter cloth.
  • the filtration in a filtration process (b) is not specifically limited, For example, the natural filtration and suction filtration etc. which pour a chitin solution on said filter cloth and filter by gravity are mentioned. Moreover, although the yield of chitin is reduced, the gel which is an impurity can be allowed to stand and then subjected to precipitation separation or centrifugation, followed by filtration (natural filtration, suction filtration, etc.).
  • the filtered chitin solution is diluted with water, and if necessary, the produced chitin precipitate is washed with water or dialyzed to remove calcium ions or magnesium ions and alcohol contained in the solution. By replacing with water molecules, a hydrated chitin slurry can be obtained.
  • the insoluble part is removed with a filter cloth (nel). Then, dilute with distilled water.
  • the dilution concentration at that time is such that the volume ratio of the chitin solution to water (chitin solution: water) is preferably 1: 1 to 1: 4, more preferably 1: 2 to 1: 3.
  • chitin solution: water When diluted with distilled water, chitin usually precipitates, and this is thoroughly washed to remove alcohol and calcium ions or magnesium ions.
  • dialysis may be performed in order to remove alcohol and calcium ions or magnesium ions. Further, washing with water and dialysis may be repeated.
  • the hydrated chitin slurry having a desired chitin content can be obtained by adjusting the water content of the obtained hydrated chitin slurry by a centrifugal method or the like.
  • the method of the present invention includes a step (d) of adding carbon dioxide and / or sodium hydrogen carbonate to a chitin solution or a hydrated chitin slurry to remove residual alcohol, and / or a chitin solution, if necessary.
  • a step (e) of adding an organic acid for example, citric acid, succinic acid, succinic anhydride, glutamic acid, ethylenediamine acid, asurbic acid
  • an organic acid for example, citric acid, succinic acid, succinic anhydride, glutamic acid, ethylenediamine acid, asurbic acid
  • an alcohol-containing aqueous solution liquid phase
  • chitin precipitate solid phase
  • solid-liquid separation means such as filtration and centrifugation.
  • the chitin precipitate from which the alcohol has been separated is treated in the same manner as in the step (c), whereby a hydrated chitin slurry with a further reduced alcohol content can be obtained.
  • an organic acid is added to a chitin solution (for example, obtained from the step (b)) or a hydrated chitin slurry (for example, obtained from the step (c) or (d)).
  • a chitin solution for example, obtained from the step (b)
  • a hydrated chitin slurry for example, obtained from the step (c) or (d)
  • To separate any remaining calcium or magnesium ions By adding such an acid to the chitin solution or hydrated chitin slurry, insoluble salts such as calcium carbonate or magnesium present in the chitin solution or hydrated chitin slurry are dissolved. Therefore, by performing dialysis or the like, calcium ions or magnesium ions can be separated from the chitin solution or hydrated chitin slurry.
  • Examples of the organic acid used in the above step (e) include citric acid, glutamic acid, ethylenediamine acid, asurbic acid, tartaric acid, malic acid, ascorbic acid, dicarboxylic acid group (oxalic acid, malonic acid, succinic acid, succinic anhydride). Acid, glutaric acid, adipic acid, pimelic acid, sebacic acid, phthalic acid, terephthalic acid, etc.). These may be used alone or as a mixture of two or more. Among these, it is preferable to use an organic acid selected from citric acid, succinic acid, succinic anhydride, glutamic acid, ethylenediamine acid, and asurbic acid from the viewpoint of safety, availability, and the like.
  • step (e) particularly to the hydrated chitin slurry (chitin precipitation) obtained from the step (d).
  • the calcium carbonate or magnesium accumulated in the hydrated chitin slurry in step (d) is dissolved in the liquid and easily separated as calcium ions or magnesium ions by known solid-liquid separation means such as filtration and centrifugation. can do.
  • a hydrated chitin slurry having a further reduced alcohol content, calcium ion content or magnesium ion content can be obtained.
  • the method of the present invention further includes a step of mechanically mixing the hydrated chitin slurry as necessary.
  • a hydration chitin slurry can be made more uniform.
  • Such mechanical mixing can be performed using, for example, various agitators such as a blender and a rotation / revolution type agitator.
  • the hydrated chitin slurry obtained by the method of the present invention can be suitably applied to the application fields of chitin and chitosan. That is, it can be applied to the following application fields.
  • Cosmetics field Health care, skin care, hair care, oral care, anti-aging cream, cleansing, etc. (humectant, thickener, inflammation suppression, ultraviolet light, hair damage suppression, skin damage suppression, skin regeneration), Repellents, etc.
  • Food field Improvement of intestinal metabolism (proliferation of lactic acid bacteria, promotion of production of ⁇ -galactosase necessary for lactose digestion), immunity enhancement, improvement of bread bulge, promotion of hyaluronic acid production, prevention and improvement of osteoarthritis, etc. Health food, functional food, etc.
  • Medical field Wound healing agent (material), non-woven fabric, artificial skin, surgical suture, cream, pharmaceuticals (medicine, non-woven fabric shape cancer cell proliferation suppression, immune enhancement effect (cancer cell growth suppression and opportunistic infection) Fungus-protective effect against Lisera monocytogenes), growth of lactic acid bacteria, promotion of ⁇ -galactose production necessary for lactose digestion, hyaluronic acid production, prevention and improvement of osteoarthritis, improvement of inflammation, healing (stomatitis, gingivitis, alveolar pyorrhea) Etc.), analgesic suppressants, hemostatic agents, bactericides), biomaterials (bones, teeth, etc.), (4) Plant field: soil improvement material, plant control material, etc. (5) Biotechnology field: Cell growth substrate, etc. (6) Molding material field: Fillers for plastic products (thickeners, biodegradable materials), natural material molded products, films, etc. (7) Thickener and the like.
  • the degree of acetylation of chitin was determined by the following procedure. (Preprocessing) (1) Put 100 ml of 2M hydrochloric acid and 2 g of chitin into a 100 ml beaker, and stir (magnetic stirrer) at 400 rpm for 30 minutes. (2) The mixture is filtered with a filter paper (“QUALITVE FILTER PAPRE NO.1” manufactured by ADVANTEC), and the filtration residue and 100 ml of methanol are put into a beaker and stirred and washed for 15 minutes. The mixture is then filtered again. (3) Repeat the above operation (2) four or more times.
  • the degree of acetylation is calculated from the following formula from the weight of chitin (a) and the titration amount (b) of 0.1N aqueous sodium hydroxide solution.
  • Degree of acetylation (%) (2.03 ⁇ b) / [a + (5.5 ⁇ b ⁇ 10 ⁇ 4 )]
  • the protein content of chitin was determined by the following procedure using 18 amino acids (lysine, histidine, phenylalanine, leucine, isoleucine, methionine, valine, threonine, tryptophan, arginine, tyrosine, alanine, glycine, proline, glutamic acid, serine, aspartic acid, cystine. ) was analyzed (amino acid analysis method).
  • Hydrolyze chitin hydrolysis; methionine and cystine are hydrolyzed with hydrochloric acid after formic acid oxidation treatment).
  • the amount of various amino acids is measured with an amino acid analyzer (Hitachi high-speed amino acid analyzer L8800k).
  • Only tryptophan is measured by high performance liquid chromatography (JLC-500 V, manufactured by JEOL Ltd.).
  • the amount of residual gel substance (g) is calculated by measuring the weight of the filter cloth together with the chitin solution in the funnel, and then subtracting the dry weight of the filter cloth from the weight. .
  • the dry weight (g) of the residual gel-like substance is determined by measuring the amount of the residual gel-like substance, immersing the filter cloth in ion-exchanged water placed in a beaker, taking out the gel-like substance from the filter cloth, Stir the contents of the beaker with a glass rod to dissolve water-soluble substances (calcium chloride, etc.). The solution is filtered, and the filtration residue is dried with a dryer, and then the weight is measured to obtain a dry weight.
  • Example 1 Preparation of hydrated chitin slurry (1) Calcium chloride dihydrate (8.5 kg; “Calcium chloride (2 water)” manufactured by Wako Pure Chemical Industries, Ltd.) dissolved in methanol (10 L) was dissolved in calcium chloride. A dihydrate saturated methanol solution was prepared. Next, the regenerated chitin powder (70 g) obtained in Production Example 1 above was added to the solution (11 L) in a water bath adjusted to 55 ° C. using a stirrer (“FINE FL-105N”). Then, the mixture was dissolved under the stirring conditions of dials 3 to 7 to prepare a chitin solution.
  • the dehydrated precipitate is further subjected to centrifugal dehydration while adding the same amount of ion-exchanged water as the amount of water discharged by centrifugal dewatering, and washed until the drainage conductivity reaches about 0.3 to 0.2 mS / m or less.
  • dehydration was performed to obtain a hydrated chitin slurry.
  • the residual amount of methanol in the obtained hydrated chitin slurry was measured by gas chromatography (GC14B manufactured by Shimadzu Corporation), it was less than the detection limit of 5 ppm.
  • a part of the obtained hydrated chitin slurry was dried overnight at 80 ° C.
  • Example 2 (1) Regenerated chitin powder (acetylation degree: 98.7%, protein content: 0.01% by weight) prepared in the same manner as in Production Example 1 above is placed in a dryer (EYELA VOS301SD manufactured by Tokyo Science Instruments Co., Ltd.). After drying in vacuo at 85 ° C. for 18 hours, 62.5 g of calcium chloride dihydrate saturated methanol prepared in the same manner as in Example 1 (1) above in a water bath adjusted to 55 ° C. The solution was added to the solution (7 L) and dissolved under the stirring conditions of the dials 2 to 7 using a stirrer (manufactured by IKA, LABORTECHNIK RW20.n) to prepare a chitin solution.
  • a stirrer manufactured by IKA, LABORTECHNIK RW20.n
  • the chitin solution was filtered using a filter cloth (average pore diameter of about 0.2 mm, average mesh number of about 4 / mm) to remove insoluble matters and the like. The filtration time was 6 minutes and 40 seconds.
  • the filtered chitin solution and 1.25 times its ion-exchanged water were subjected to agitation conditions of 10,300 to 15,700 rpm using a blender (Oster Blender ST-1 manufactured by Oster). Mix and then let stand overnight to precipitate chitin.
  • the precipitate was dehydrated using a centrifugal dehydrator (“H-122” manufactured by Kokusan Co., Ltd.) under conditions of 500 to 1,000 rpm and using a filter cloth (PR-20 manufactured by Kokusan).
  • Example 3 Regenerated chitin powder (80 g; degree of acetylation 96.4%, protein content 0.01% by weight) prepared in the same manner as in Production Example 1 above, in a water bath adjusted to 55 ° C., Add to calcium chloride dihydrate saturated methanol solution (11 L) prepared in the same manner as in Example 1 (1) above, and use dial 2-7 with stirrer (LABORTECHNIK RW20.n, manufactured by IKA). A chitin solution was prepared by dissolving under stirring conditions. (2) The chitin solution was filtered using a filter cloth (average pore diameter of about 0.2 mm, average mesh number of about 4 / mm) to remove insoluble matters and the like.
  • a filter cloth average pore diameter of about 0.2 mm, average mesh number of about 4 / mm
  • Example 4 Regenerated chitin (1.000 g; degree of acetylation 97.5%, protein content 0.01% by weight) prepared in the same manner as in Production Example 1 was prepared in the same manner as in Example 1 (1) above.
  • the solution was added to a calcium chloride dihydrate saturated methanol solution (137 mL), and dissolved by stirring for 7 hours with a stirrer while keeping the temperature in a water bath adjusted to 55 ° C.
  • the solution was filtered through a high speed funnel made of PP with a filter cloth (average pore size 130 ⁇ m, average mesh number 4 mesh / mm), and the time required for 100 mL and 125 mL filtration (filtration time) was measured.
  • Example 5 A chitin solution was obtained in the same manner as in Example 4 except that regenerated chitin having a high degree of acetylation (degree of acetylation 98.7%, protein content 0.01% by weight) was used. The amount of time and filtration residue was measured. As a result, it took 300 seconds for 100 mL filtration, and 721 seconds for 125 mL filtration. The amount of the residual gel substance was 5.674 g, and the dry weight was 0.111 g. The chitin solution was diluted and washed to obtain a chitin slurry.
  • Example 7 The regenerated chitin used in Example 4 (acetylation degree: 97.5%, protein content: 0.01% by weight) using a dryer (“EYELA VOS301SD” manufactured by Tokyo Science Instrument Co., Ltd.) at 100 ° C. for 12 hours Vacuum dried. Thereafter, in the same manner as in Example 4 above, a chitin solution was obtained and filtered, and the filtration time and the amount of filtration residue were measured. As a result, it took 296 seconds for 100 mL filtration, and 945 seconds for 125 mL filtration. The amount of residual gel substance was 6.971 g, and the dry weight was 0.337 g. The chitin solution was diluted and washed to obtain a chitin slurry.
  • a dryer EYELA VOS301SD
  • Example 8 (1) 50 ml of a chitin solution prepared in the same manner as in Example 4 above (chitin content 0.4 g, chitin acetylation degree 97.5%, chitin protein content 0.01 wt%) and sodium hydrogen carbonate (1 g; Sigma-Aldrich, sodium hydrogen carbonate, special grade) were mixed, stirred, and filtered to obtain a precipitate. The pH at that time was 4.5. (2) The obtained precipitate was mixed with a 1% (w / v) aqueous citric acid solution (300 ml; manufactured by Sigma-Aldrich, citric acid, first grade), filtered after stirring. (3) The obtained precipitate was repeatedly washed with ion-exchanged water and filtered to finally obtain 5.2 g of chitin slurry. The yield was 38%.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

La présente invention concerne un procédé permettant la production d'une suspension de chitine hydratée comprenant les étapes (a) à (c) suivantes : (a) la dissolution d'une chitine ayant une teneur en protéine inférieure à 0,14% en poids et un degré d'acétylation égal ou supérieur à 96% dans un solvant comportant un alcool choisi parmi l'alcool méthylique et l'alcool éthylique et un sel halogéné de calcium ou un sel halogéné de magnésium pour produire une solution à base de chitine ; (b) la filtration de la solution à base de chitine pour éliminer toute matière insoluble ; et (c) la dilution de la solution à base de chitine avec de l'eau, et éventuellement le lavage d'un précipité produit de chitine ou la réalisation d'une dialyse pour substituer un ion de calcium ou un ion de magnésium et l'alcool contenu dans la solution par une molécule d'eau, produisant ainsi la suspension de chitine hydratée.
PCT/JP2008/071545 2008-11-27 2008-11-27 Procédé pour la production de suspension de chitine de haute pureté Ceased WO2010061454A1 (fr)

Priority Applications (2)

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PCT/JP2008/071545 WO2010061454A1 (fr) 2008-11-27 2008-11-27 Procédé pour la production de suspension de chitine de haute pureté
JP2010540259A JP4868428B2 (ja) 2008-11-27 2008-11-27 高純度キチンスラリーの製造方法

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010185019A (ja) * 2009-02-12 2010-08-26 Idemitsu Technofine Co Ltd キチン−ポリアミノ酸複合組成物、その製造方法、および、キチン−ポリアミノ酸複合材料
US9527929B2 (en) 2014-01-30 2016-12-27 Sofradim Production Optimized chitosan reacetylation

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07316202A (ja) * 1994-05-25 1995-12-05 Fuji Spinning Co Ltd キチンスポンジ，キチン紙，キチンフィルムの製造方法
JP2005036109A (ja) * 2003-07-15 2005-02-10 Chitosan Kowa:Kk 甲殻類の殻からキチンゲルを製造する簡便法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07316202A (ja) * 1994-05-25 1995-12-05 Fuji Spinning Co Ltd キチンスポンジ，キチン紙，キチンフィルムの製造方法
JP2005036109A (ja) * 2003-07-15 2005-02-10 Chitosan Kowa:Kk 甲殻類の殻からキチンゲルを製造する簡便法

Non-Patent Citations (2)

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Title
"Kansai Daigaku Sentan Kagaku Gijutsu Symposium Koenshu", vol. 10, 2006, article HIROSHI TAMURA: "Chitin Kayoka Yobai no Shinten", pages: 76 - 77 *
TAMURA H. ET AL.: "N-acetylation dependent... saturated methanol", ADVANCES IN CHITIN SCIENCE, vol. 6, 2002, pages 293 - 294 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010185019A (ja) * 2009-02-12 2010-08-26 Idemitsu Technofine Co Ltd キチン−ポリアミノ酸複合組成物、その製造方法、および、キチン−ポリアミノ酸複合材料
US9527929B2 (en) 2014-01-30 2016-12-27 Sofradim Production Optimized chitosan reacetylation

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JP4868428B2 (ja) 2012-02-01

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