JPH0841106A - Low-viscosity chitosan and its production - Google Patents

Low-viscosity chitosan and its production

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Publication number
JPH0841106A
JPH0841106A JP19378194A JP19378194A JPH0841106A JP H0841106 A JPH0841106 A JP H0841106A JP 19378194 A JP19378194 A JP 19378194A JP 19378194 A JP19378194 A JP 19378194A JP H0841106 A JPH0841106 A JP H0841106A
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viscosity
chitosan
low
chitin
preferably
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JP2901176B2 (en )
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Hiroshi Kameyama
Akira Sato
Tadao Sekiguchi
博 亀山
亮 佐藤
忠雄 関口
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Nippon Kayaku Co Ltd
日本化薬株式会社
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Abstract

PURPOSE:To economically obtain a low-viscosity chitosan containing none of oxidizing agent, reducing agent and enzyme and having high safety by the deacetylation of an aqueous alkaline solution of the carapace of a crustacean, a chitin or the like. CONSTITUTION:The chitosan is substantially free from oxidizing agent, reducing agent and chitosan hydrolase, has a viscosity of preferably 5-50mPa.c or lower and a degree of acetylation of preferably at least 85%. The process for producing the chitosan comprises deacetylating a chitin preferably of a viscosity as low as at most 100mPa.c with a concentrated aqueous alkali to give a chitosan having a viscosity as low as at most 100mPa.c and still preferably having a degree of acetylation of at least 85%. A preferable example of the chitin of a viscosity as low as at most 100mPa.c is one obtained by treating the carapace of a crustacean, optionally deproteinized, or a chitin having a viscosity of at least 200mPa.c with a dilute aqueous acid at 50 deg.C or higher.

Description

【発明の詳細な説明】 DETAILED DESCRIPTION OF THE INVENTION

【0001】 [0001]

【産業上の利用分野】キチン及びキトサンは難消化性により食物繊維の効果が期待されている。 Chitin and chitosan BACKGROUND OF THE effect of dietary fiber has been expected by the indigestible. 中でもキトサンは多くのアミノ基をもつことにより、消化管内で胆汁酸を吸着し、血清コレステロ−ル低下作用を示すことから、今後キトサンは降コレステロ−ル作用を活用した機能性食品への応用が期待されている。 By having many amino groups among others chitosan adsorbs bile acids in the digestive tract, serum cholesterol - the exhibit Le lowering effect, future chitosan later cholesterol - the application to functional food utilizing le action It is expected. 又、低分子化したキトサンの中である特定の分子量を有するものが抗菌力を示したり、抗癌活性が認められている。 Further, those having a specific molecular weight is in the low molecular weight chitosan is or exhibit antimicrobial power, anticancer activity was observed. 今後は、工業用、医療用、食品用とあらゆる分野での応用が展開され、安価で安全性の高い低粘度キトサンが望まれている。 In the future, industrial, medical, food and application of in every field is expanded, are inexpensive and highly secure low-viscosity chitosan is desired. 本発明は低粘度キトサン及びその製造方法に関する。 The present invention relates to low viscosity chitosan and a manufacturing method thereof.

【0002】 [0002]

【従来の技術】従来の低粘度キチン及び低粘度キトサンの製造は、甲殻類の甲皮等を加温希アルカリで除タンパクした後、常温で塩酸水溶液で脱カルシウム処理してキチンを得、キチンを強アルカリ中90〜120℃で脱アセチル化してキトサンを製造した後、得られたキトサンを過酸化水素、過ホウ酸ソーダ等の酸化剤、又は、アスコルビン酸等の還元剤で処理する方法、及び、キトサンを分解する酵素例えばプロテアーゼ、パパイン等のタンパク分解酵素、セルラーゼ等の糖分解酵素あるいはキチナーゼ、キトサナーゼ等の酵素(これらを総称してキトサン分解酵素という)で処理して低粘度キチン及び低粘度キトサンを製造する方法が知られている。 Manufacture of conventional low viscosity chitin and low viscosity chitosan, after deproteinization instep skin like a pressurized YutakaNozomi alkaline crustaceans, to obtain a chitin with calcium-depleted aqueous hydrochloric acid at room temperature, chitin after producing a chitosan deacetylated with a strong alkaline in 90 to 120 ° C., and the resulting chitosan hydrogen peroxide, oxidizing agent such as perborate sodium, or a method of treatment with a reducing agent such as ascorbic acid, and chitosan degrades enzymes such as a protease, a proteolytic enzyme, glycolytic enzyme or chitinase cellulase, such enzymatic treatment to low viscosity chitin and low in (these are collectively called chitosan degrading enzymes) chitosanase such papain there is known a method of producing a viscosity chitosan.

【0003】 [0003]

【発明が解決しようとする課題】しかし、酸化剤や還元剤及び酵素で処理する方法は、生産効率が悪い上に、得られたキトサン中にそれらの薬剤が含まれるため、その安全性が疑問視されている。 [0006] However, a method of treating with an oxidizing agent or a reducing agent and enzymes, on the production efficiency, because it contains these agents in the resulting chitosan, its safety is questionable It has been seen. 特に、食品用としての製造方法としては好ましくなかった。 In particular, as a method of manufacturing as for food it is not preferable.

【0004】 [0004]

【課題を解決するための手段】そこで本発明者らは種々検討した結果、甲殻類の甲皮及び脱タンパクされた甲殻類の甲皮又は200mPa・c以上の粘度を有するキチンを50℃以上の希酸水溶液で処理することで100m [SUMMARY OF] The present inventors have results of various studies, crustaceans chitin than 50 ° C. with a carapace or 200 mPa · c more viscosity of carapace and deproteinized been shellfish 100m by treatment with dilute aqueous acid
Pa・c以下の低粘度キチンが得られることおよび得られた低粘度キチンを脱アセチル化処理することで100 It Pa · c or lower viscosity chitin is obtained and the low viscosity chitin obtained with treating deacetylation 100
mPa・c以下の低粘度キトサンが得られることを見いだした。 It found that the following low viscosity chitosan mPa · c is obtained. 本発明は、酸及びアルカリ処理のみで容易に得られるので生産効率が高く、しかも、酸化剤、還元剤、 The present invention has a high production efficiency since it is easily obtained only by acid and alkali treatment, moreover, oxidizing agents, reducing agents,
及びキトサン分解酵素等を一切使用していないので極めて安全性の高い製造方法である。 And an extremely high safety manufacturing method since chitosan enzyme, or the like is not used at all. 本発明は上記知見に基づいて完成されたものである。 The present invention has been completed based on the above findings. 即ち、本発明は実質上、 That is, the present invention is substantially,
酸化剤、還元剤及びキトサン分解酵素を含まないことを特徴とする低粘度キトサン及びその製造方法に関する。 Oxidizing agent to low viscosity chitosan and a manufacturing method thereof, characterized in that it is free of reducing agent and chitosan degrading enzymes.

【0005】より詳しくは、本発明の低粘度キトサンは、甲殻類の甲皮及び脱タンパクされた甲殻類の甲皮又は200mPa・c以上の粘度を有するキチンを50℃ [0005] More specifically, a low viscosity chitosan of this invention, 50 ° C. chitin having a carapace and carapace or 200 mPa · c more viscosity of deproteinized been crustacean shellfish
以上の希酸水溶液で処理して得られる100mPa・c 100 mPa · c obtained by treating the above dilute aqueous acid solution
以下の低粘度キチンを濃アルカリ水溶液で脱アセチル化し、100mPa・c以下の低粘度キトサンとすることにより得ることができる。 The following low viscosity chitin deacetylation by concentrated alkali aqueous solution can be obtained by the following low-viscosity chitosan 100 mPa · c.

【0006】本発明における原材料の甲殻類の甲皮及び脱タンパクされた甲殻類の甲皮及びキチンとしては、 [0006] As the carapace and carapace and chitin of deproteinized been crustacean crustaceans of raw materials in the present invention,
蟹、シャコ、海老、オキアミ等を原料とし、それを希アルカリ水溶液で脱蛋白して得るか、更に希酸で脱カルシウムすることによって得られる。 Crab, clam, shrimp, krill, etc. as a raw material, or it may be deproteinized by a dilute aqueous alkaline solution, obtained by decalcified further with dilute acid. その粒度及び甲殻類の種類は特に限定するものではない。 Type of particle size and crustaceans are not particularly limited. 又、甲殻類の甲皮等を先に脱カルシウム処理した後、脱タンパク処理しても同様に得られるが製造上脱タンパク処理して脱カルシウム処理する方が好ましい。 Further, after the calcium-depleted instep skins like in the previous crustaceans, it is better to be deproteinized obtained similarly although calcium depleted and deproteinized manufacturing preferred.

【0007】本発明の原料である低粘度キチンを得るための希酸水溶液での処理温度は50℃以上でよいが、6 [0007] treatment temperature in the dilute aqueous acid solution to obtain a low viscosity chitin, which is a raw material of the present invention may at 50 ° C. or higher, but 6
0℃以上が好ましい。 0 ℃ or more. 又、処理時間は使用する原材料の粒度及びカルシウム含有量により異なるが、0.5〜1 Further, the processing time varies depending on the particle size and calcium content of the raw materials used, 0.5 to 1
0時間でよいが、生産効率上1〜3時間程度が好ましい。 Or 0 hours, 1-3 hours about the production efficiency is preferred. 処理温度が高い程、また処理時間が長い程、また希酸濃度が高い程、低粘度のものが得られる。 Higher treatment temperature is high, also the longer the processing time, also as the dilute acid concentration is high, the low viscosity ones are obtained.

【0008】希酸水溶液としては、希酸水溶液であれば塩酸、硝酸、酢酸、硫酸、炭酸、蓚酸等いずれでも良いが希塩酸水溶液が好ましい。 [0008] As the dilute aqueous acid solution, hydrochloric acid if dilute aqueous acid solution, nitric acid, acetic acid, sulfuric acid, carbonic acid, good dilute aqueous hydrochloric acid either oxalic acid are preferred. 酸の濃度は2〜15w/w The concentration of the acid 2~15w / w
%、好ましくは3〜10w/w%程度がよい。 %, Preferably from about 3~10w / w%. 又、その量は、原材料の甲殻類の甲皮等が浸る量であれば特に制限は無いが、5〜20倍程度が好ましい。 In addition, the amount is not particularly limited as long as it is an amount that the instep skin or the like is immersed crustaceans of raw materials, preferably about 5 to 20 times.

【0009】希酸水溶液での処理後の水洗は充分に洗浄することが望ましい。 [0009] washing after treatment with dilute aqueous acid, it is desirable to sufficiently cleaned. なぜなら、洗浄が不充分な場合、 This is because, if the cleaning is insufficient,
更に分子量又は粘度が低下して分子量又は粘度のコントロールが不安定になるからである。 Molecular weight or control the viscosity decreases more molecular weight or viscosity is because unstable. 又、この乾燥条件のみでの低分子化又は低粘度化の可能性はあるが物性の変動が激しく実用的ではない。 Moreover, the drying conditions only there is a possibility of a low molecular weight or low viscosity in but is not intensely practical variations in properties.

【0010】低粘度のキトサンを得るには、低粘度キチンを使用すればよく、脱アセチル化反応温度と反応時間は、特に制限されないが通常50〜120℃、好ましくは80℃〜120℃より好ましくは90℃〜120℃の範囲の温度で、1〜25時間反応させると好ましい。 [0010] To obtain a low viscosity chitosan may be used a low viscosity chitin, reaction time deacetylation reaction temperature is particularly unrestricted usually 50 to 120 ° C., preferably more preferably 80 ° C. to 120 ° C. preferably at a temperature in the range of 90 ° C. to 120 ° C., the reaction 1 to 25 hours.

【0011】脱アセチル化剤としては、例えば水酸化ナトリウム、水酸化カリウム等のアルカリ水溶液などがあげられるが、水酸化ナトリウムが好ましい。 [0011] As deacetylating agents, for example sodium hydroxide, an alkaline aqueous solution such as potassium hydroxide and the like, sodium hydroxide is preferred. 反応時のアルカリ濃度は30〜60w/w%、好ましくは45〜5 Alkali concentration during the reaction is 30 to 60 W / w%, preferably 45 to 5
5w/w%程度がよい。 About 5w / w% is good. 又、その量は、キチンが浸る量であれば特に制限は無いが、10〜30倍程度が好ましい。 Further, the amount is not particularly limited as long as it is an amount that chitin is immersed, preferably about 10 to 30 times.

【0012】このようにして得られる本発明の低粘度キトサンの平均分子量としては、数万〜数十万であり、また、粘度としては、100mPa・c以下であり、好ましくは5〜50mPa・cである。 [0012] The average molecular weight of the low viscosity chitosan of this invention thus obtained, a several tens of thousand to several hundreds of thousand, The viscosity no greater than 100 mPa · c, preferably 5 to 50 mPa · c it is. 好ましい脱アセチル化度は80%以上、より好ましくは85%以上である。 Preferred degree of deacetylation of 80% or more, more preferably 85% or more.

【0013】以上から本発明の低粘度キチン及び低粘度キトサンの製造方法は実質上、酸化剤、還元剤、酵素等を一切含まない極めて安全な実用性の高いものである。 [0013] The method of producing low-viscosity chitin and low viscosity chitosan of this invention from the above effect, oxidizing agents, reducing agents, those extremely high safety utility that does not contain any enzyme or the like.
尚、ここで用いるキトサンの平均分子量の測定方法及びキチン又はキトサンの粘度の測定方法は下記の通りである。 The measurement method of viscosity measurement method and chitin or chitosan with an average molecular weight of the chitosan used herein is as follows. 又、脱アセチル化度の測定は、ポリビニル硫酸カリウム溶液によるコロイド滴定法を採用した。 Also, the measurement of the deacetylation degree was adopted colloid titration with potassium polyvinyl sulfate solution.

【0014】[キチン粘度の測定方法]300mlビーカーに乾燥キチン試料0.6gを正確に採取し、溶解液(ジメチルアセトアミド100:8塩化リチウム)30 [0014] The 300ml beaker dry chitin sample 0.6g accurately collected Measurement method of chitin viscosity, solution (dimethylacetamide 100: 8 lithium chloride) 30
0gを加えて24時間撹拌溶解する。 It added 0g to 24 hours of stirring dissolved. 試料溶液の温度を30±0.5℃に保持し、B型粘度計を用いて30回転で回転粘度(mPa・c)を測定する。 The temperature of the sample solution was maintained at 30 ± 0.5 ° C., to measure the rotational viscosity (mPa · c) at 30 revolutions using a B-type viscometer.

【0015】[キトサン粘度の測定方法]300mlビーカーに乾燥キトサン試料1.5gを正確に採取し、純水297gを加えて撹拌し試料を分散した後、酢酸1.5 [0015] The dried chitosan samples 1.5g in 300ml beaker Measurement method of chitosan Viscosity accurately taken, after dispersing the sample stirred with pure water 297 g, acetic acid 1.5
gを添加して2時間撹拌溶解する。 It was added g to 2 hours dissolved by stirring. 試料溶液の温度を2 The temperature of the sample solution 2
0±0.5℃に保持し、B型粘度計を用いて30回転で回転粘度(mPa・c)を測定する。 0 holds in the ± 0.5 ° C., to measure the rotational viscosity (mPa · c) at 30 revolutions using a B-type viscometer.

【0016】[キトサン平均分子量の測定方法]プルラン分子量標準を用い検量線を作成する。 [0016] To create a calibration curve using pullulan molecular weight standards [Measurement method of chitosan average molecular weight. キトサンを溶離液で溶解した溶液の分子量を測定する。 Determining the molecular weight of solution of chitosan in the eluent. カラムは水素G Column hydrogen G
PCカラムを用いた。 Using a PC column.

【0017】 [0017]

【実施例】以下に実施例を挙げて本発明を具体的に説明するが、本発明はこれらに限定されるものではない。 EXAMPLES The following examples illustrate the present invention in detail, but the present invention is not limited thereto.

【0018】実施例1 脱タンパクされた2〜8メッシュのズワイ蟹の殻100 [0018] The shell 100 of Snow crab of 2-8 mesh, which is the first embodiment deproteinized
gを、5w/w%塩酸600gに投入し50℃で5時間撹拌して脱カルシウム処理した。 g were calcium-depleted stirred 5 hours at poured into 5w / w% hydrochloric acid 600 g 50 ° C.. 得られたキチンを濾過し、充分水洗して乾燥しキチン23.6gを得た。 The resulting chitin was filtered and dried to obtain chitin 23.6g and sufficiently washed with water. 得られたキチンの粘度は63mPa・cであった。 The viscosity of the resulting chitin was 63 MPa · c.

【0019】実施例2 10〜20メッシュのズワイ蟹の乾燥殻200gを、6 [0019] The dry shell 200g of Snow crab of Example 2 10 to 20 mesh, 6
w/w%塩酸1.3kgに投入し70℃で1.0時間撹拌して脱カルシウム処理した。 It was 1.0 hours with stirring to calcium depleted in put into w / w% hydrochloric acid 1.3 kg 70 ° C.. 得られたキチンを8%水酸化ナトリウムで80℃で2時間脱タンパク処理した後、濾過し、充分水洗して乾燥しキチン41.0gを得た。 The resulting was chitin 2 hours deproteinization treatment at 80 ° C. in 8% sodium hydroxide, filtered and dried to obtain chitin 41.0g and sufficiently washed with water. 得られたキチンの粘度は34mPa・cであった。 The viscosity of the resulting chitin was 34 mPa · c.

【0020】実施例3 脱タンパクされた10〜20メッシュのズワイ蟹の殻1 [0020] Example 3 shell 1 of Snow crab of 10 to 20 mesh, which is deproteinized
00gを、9w/w%塩酸600gに投入し70℃で3 The 200 g, at poured into 9w / w% hydrochloric acid 600 g 70 ° C. 3
時間撹拌して脱カルシウム処理した。 It was treated decalcified by stirring time. 得られたキチンを濾過し、充分水洗して乾燥しキチン24.2gを得た。 The resulting chitin was filtered and dried to obtain chitin 24.2g and sufficiently washed with water.
得られたキチンの粘度は13mPa・cであった。 The viscosity of the resulting chitin was 13 mPa · c.

【0021】実施例4 粘度800mPa・cの未粉砕キチン100kgを、3 The unground chitin 100kg of Example 4 Viscosity 800 mPa · c, 3
w/w%塩酸600kgに投入し60℃で2時間撹拌して再脱カルシウム処理した。 2 hours to re-calcium-depleted stirred at charged to 60 ° C. in w / w% hydrochloric acid 600 kg. 得られたキチンを濾過し、 The obtained chitin was filtered,
充分水洗して乾燥しキチン99.2kgを得た。 And dried thoroughly washed with water to obtain a chitin 99.2kg. 得られたキチンの粘度は39mPa・cであった。 The viscosity of the resulting chitin was 39 MPa · c.

【0022】実施例5 実施例1〜4で得られた乾燥キチンを各5gづつ採取し、50w/w%水酸化ナトリウム溶液120gを加えて110℃で3時間反応して脱アセチル化した。 [0022] The dry chitin obtained in Example 5 Examples 1-4 were taken each 5g increments, and 3 hours to deacetylation at 110 ° C. was added a 50 w / w% sodium hydroxide solution 120 g. 得られたキトサンを濾過、水洗、乾燥し、キトサンを得た。 The obtained chitosan is filtered, washed with water, and dried to obtain a chitosan. 得られたキトサンの重量、脱アセチル化度及び粘度は表1 The weight of the obtained chitosan deacetylation degree and viscosity Table 1
の通りであった。 It was as.

【0023】 [0023]

【表1】 表1 実施例No キチン 粘度 脱アセチル化度 キトサン重量 キトサン粘度 キトサン平均分子量 (mPa・ c) (%) (g) (mPa・ c) 1 63 93.6 39.8 31 28万 2 34 94.7 39.4 18 15万 3 13 94.9 39.9 6 5万 4 39 92.0 40.5 20 18万 TABLE 1 Example No chitin viscosity deacetylation degree of chitosan by weight chitosan viscosity chitosan-average molecular weight (mPa · c) (%) (g) (mPa · c) 1 63 93.6 39.8 31 28 million in 2 34 94.7 39.4 18 150003 13 94.9 399 650 4 39 92.0 40.5 20 180,000

【0024】実施例6 実施例1〜4で得られた低粘度キチンを各5gづつ採取し、45w/w%水酸化ナトリウム溶液150gを加えて90℃で12時間反応して脱アセチル化した。 [0024] The low viscosity chitin obtained in Example 6 Examples 1-4 were taken each 5g increments was deacetylated by reacting 12 hours at 90 ° C. was added a 45 w / w% sodium hydroxide solution 150 g. 得られたキトサンを濾過、水洗、乾燥し、キトサンを得た。 The obtained chitosan is filtered, washed with water, and dried to obtain a chitosan. 得られたキトサンの重量、脱アセチル化度及び粘度は表2 The weight of the obtained chitosan deacetylation degree and viscosity Table 2
の通りであった。 It was as.

【0025】 [0025]

【表2】 表2 実施例No キチン 粘度 脱アセチル化度 キトサン重量 キトサン粘度 キトサン平均分子量 (mPa・ c) (%) (g) (mPa・ c) 1 63 94.3 39.6 62 58万 2 34 95.0 39.5 37 33万 3 13 95.9 39.0 22 19万 4 39 94.0 40.8 41 38万 TABLE 2 Example No chitin viscosity deacetylation degree of chitosan by weight chitosan viscosity chitosan-average molecular weight (mPa · c) (%) (g) (mPa · c) 1 63 94.3 39.6 62 58 million in 2 34 95.0 39.5 37 330003 13 95.9 39.0 22 190 004 39 94.0 40.8 41 380,000

【0026】実施例7 実施例1〜4で得られたキチンを各10gづつ採取し、 The chitin obtained in Example 7 Examples 1-4 were taken each 10g increments,
48w/w%水酸化ナトリウム溶液200gを加えて6 Adding 48 w / w% sodium hydroxide solution 200 g 6
5℃で20時間反応して脱アセチル化した。 At 5 ° C. and reacted for 20 hours deacetylated. 得られたキトサンを濾過、水洗、乾燥し、キトサンを得た。 The obtained chitosan is filtered, washed with water, and dried to obtain a chitosan. 得られたキトサンの重量、脱アセチル化度及び粘度は表3の通りであった。 The weight of the obtained chitosan deacetylation degree and viscosity were as shown in Table 3.

【0027】 [0027]

【表3】 表3 実施例No キチン 粘度 脱アセチル化度 キトサン重量 キトサン粘度 キトサン平均分子量 (mPa・ c) (%) (g) (mPa・ c) 1 63 89.3 39.9 84 71万 2 34 90.5 39.3 69 64万 3 13 91.2 39.6 29 22万 4 39 88.0 40.2 53 46万 TABLE 3 Example No chitin viscosity deacetylation degree of chitosan by weight chitosan viscosity chitosan-average molecular weight (mPa · c) (%) (g) (mPa · c) 1 63 89.3 39.9 84 71 million in 2 34 90.5 39.3 69 640003 13 91.2 39.6 29 220 004 39 88.0 40.2 53 460,000

【0028】本発明によれば、酸化剤・還元剤及びキトサン分解酵素を一切含まない安全性の高い低粘度キトサンが効率良く得られ、特に食品用等のあらゆる分野での応用展開が可能となる。 According to the invention, high low viscosity chitosan safety containing no oxidizing agent, a reducing agent and chitosan degrading enzyme are obtained efficiently, it is possible to particularly application and development in all areas of food, etc. .

Claims (6)

    【特許請求の範囲】 [The claims]
  1. 【請求項1】 酸化剤、還元剤、及びキトサン分解酵素を実質的に含まないことを特徴とする低粘度キトサン 1. A oxidizer, low viscosity chitosan characterized in that it is free reducing agent, and chitosan degrading enzyme substantially
  2. 【請求項2】 粘度が5〜50mPa・c以下である請求項1記載の低粘度キトサン 2. A low-viscosity chitosan according to claim 1, wherein the viscosity is less than 5 to 50 mPa · c
  3. 【請求項3】 脱アセチル化度が85%以上である請求項1記載の低粘度キトサン 3. A low-viscosity chitosan according to claim 1, wherein the degree of deacetylation is 85% or more
  4. 【請求項4】 100mPa・c以下の低粘度キチンを濃アルカリ水溶液で脱アセチル化し、100mPa・c 4. deacetylated 100 mPa · c or lower viscosity chitin with concentrated alkali aqueous solution, 100 mPa · c
    以下の低粘度キトサンを得ることを特徴とする請求項1 Claim 1, characterized in that to obtain the following low viscosity chitosan
    記載の低粘度キトサンの製造方法 The method of producing low-viscosity chitosan according
  5. 【請求項5】 低粘度キトサンの脱アセチル化度が85 Deacetylation degree of 5. The low viscosity chitosan 85
    %以上である請求項4記載の製造方法 Method of manufacturing% or more in a claim 4, wherein
  6. 【請求項6】 100mPa・c以下の低粘度キチンとして、甲殻類の甲皮、脱タンパクされた甲殻類の甲皮または200mPa・c以上の粘度を有するキチンを50 As 6. 100 mPa · c or lower viscosity chitin, the carapace of crustaceans, chitin having a carapace or 200 mPa · c more viscosity of deproteinized by shellfish 50
    ℃以上の希酸水溶液で処理して得られる100mPa・ ° C. 100 mPa · obtained by treating the above dilute aqueous acid solution
    c以下の低粘度キチンを用いる請求項4記載の低粘度キトサンの製造方法 The method of producing low-viscosity chitosan according to claim 4, wherein using the following low viscosity chitin c
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WO2001068714A1 (en) * 2000-03-15 2001-09-20 Cargill, Incorporated Chitosan and method of preparing chitosan
US6693188B2 (en) 2001-08-08 2004-02-17 Cargill Incorporated N-acetyl-D-glucosamine and process for producing N-acetyl-D-glucosamine
JP2007002123A (en) * 2005-06-24 2007-01-11 Dainichiseika Color & Chem Mfg Co Ltd Fine chitosan particle
US7488812B2 (en) 2002-04-02 2009-02-10 Cargill, Incorporated Chitosan production
JP2009167140A (en) * 2008-01-18 2009-07-30 Koyo Chemical Kk Method for producing n-acetylglucosamine and application thereof
US7816514B2 (en) 2001-02-16 2010-10-19 Cargill, Incorporated Glucosamine and method of making glucosamine from microbial biomass
US7923437B2 (en) 2001-02-16 2011-04-12 Cargill, Incorporated Water soluble β-glucan, glucosamine, and N-acetylglucosamine compositions and methods for making the same
US8222232B2 (en) 2001-02-16 2012-07-17 Cargill, Incorporated Glucosamine and N-acetylglucosamine compositions and methods of making the same fungal biomass

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001068714A1 (en) * 2000-03-15 2001-09-20 Cargill, Incorporated Chitosan and method of preparing chitosan
US6972284B2 (en) 2000-03-15 2005-12-06 Cargill, Incorporated Chitosan and method of preparing chitosan
US7413881B2 (en) 2000-03-15 2008-08-19 Cargill, Incorporated Chitosan and method of preparing chitosan
US7816514B2 (en) 2001-02-16 2010-10-19 Cargill, Incorporated Glucosamine and method of making glucosamine from microbial biomass
US8034925B2 (en) 2001-02-16 2011-10-11 Cargill, Incorporated Glucosamine and method of making glucosamine from microbial biomass
US7923437B2 (en) 2001-02-16 2011-04-12 Cargill, Incorporated Water soluble β-glucan, glucosamine, and N-acetylglucosamine compositions and methods for making the same
US8222232B2 (en) 2001-02-16 2012-07-17 Cargill, Incorporated Glucosamine and N-acetylglucosamine compositions and methods of making the same fungal biomass
US6693188B2 (en) 2001-08-08 2004-02-17 Cargill Incorporated N-acetyl-D-glucosamine and process for producing N-acetyl-D-glucosamine
US7488812B2 (en) 2002-04-02 2009-02-10 Cargill, Incorporated Chitosan production
JP2007002123A (en) * 2005-06-24 2007-01-11 Dainichiseika Color & Chem Mfg Co Ltd Fine chitosan particle
JP2009167140A (en) * 2008-01-18 2009-07-30 Koyo Chemical Kk Method for producing n-acetylglucosamine and application thereof

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