JPH115803A - Production of amorphous water-soluble partially deacetylated chitin - Google Patents
Production of amorphous water-soluble partially deacetylated chitinInfo
- Publication number
- JPH115803A JPH115803A JP16122397A JP16122397A JPH115803A JP H115803 A JPH115803 A JP H115803A JP 16122397 A JP16122397 A JP 16122397A JP 16122397 A JP16122397 A JP 16122397A JP H115803 A JPH115803 A JP H115803A
- Authority
- JP
- Japan
- Prior art keywords
- chitin
- partially deacetylated
- alkali
- dope
- deacetylation
- 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.)
- Granted
Links
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- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】この発明は、Ｎ−アセチル−
Ｄ−グルコサミンとＤ−グルコサミンとを構成単位と
し、Ｎ−アセチル−Ｄ−グルコサミン単位の含量が３５
〜６５％、Ｄ−グルコサミン単位の含量が６５〜３５％
である非晶質の水溶性部分脱アセチル化キチンの製造方
法に関する。[0001] The present invention relates to N-acetyl-
D-glucosamine and D-glucosamine are the constituent units, and the content of N-acetyl-D-glucosamine unit is 35.
~ 65%, D-glucosamine unit content is 65 ~ 35%
And a method for producing an amorphous water-soluble partially deacetylated chitin.
【０００２】[0002]
【従来の技術】従来のこの種の技術としては、例えば、
特公昭５９−１９１２２号公報に開示されているよう
に、天然産キチンを５０℃以下で均一系においてアルカ
リ加水分解する際に、キチンの脱アセチル化率が４０〜
６０％となるように部分脱アセチル化し、次いで酸で中
和等する方法が知られている。2. Description of the Related Art Conventional techniques of this kind include, for example,
As disclosed in JP-B-59-19122, when a naturally produced chitin is subjected to alkaline hydrolysis in a homogeneous system at 50 ° C or lower, the deacetylation rate of chitin is 40 to 40%.
It is known to partially deacetylate to 60% and then neutralize with acid.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、上記の
ような従来の製造方法においては、原料となる天然産キ
チンにＣａＣＯ3 等の無機物やタンパク質の含量が比較
的多い粗成品を用いているので、この天然産キチン粉末
からアルカリキチンドープを効率良く調製するために
は、その粒度を８０メッシュ程度より細かくしなければ
ならず、そのため、天然産キチン粉末の調製に手間や時
間がかかるという問題点がある。However, in the above-mentioned conventional production method, a crude product having a relatively high content of inorganic substances and proteins such as CaCO 3 is used for natural chitin as a raw material. In order to efficiently prepare an alkali chitin dope from this naturally occurring chitin powder, the particle size must be finer than about 80 mesh, and therefore, there is a problem that preparation of the naturally produced chitin powder requires time and effort. is there.
【０００４】また、前記天然産キチン粉末をアルカリ水
溶液に分散させる等してアルカリキチンドープを調製し
た後、熟成させる前には濾過が必要であり、そのため、
生産効率が良くないという問題点がある。Further, after preparing the chitin dope by dispersing the above-mentioned natural chitin powder in an aqueous alkali solution, it is necessary to perform filtration before ripening the dope.
There is a problem that the production efficiency is not good.
【０００５】更に、例えばポリマー濃度１％、アルカリ
濃度１０％のアルカリキチンドープを脱アセチル化率が
４０〜６０％となるように部分脱アセチル化する場合に
は、熟成温度が２５℃では３０〜１１０時間、３０℃で
は２０〜５０時間、４０℃では１０〜３０時間必要であ
ることが開示されており、熟成に比較的長時間を要する
という問題点がある。Further, for example, when partially deacetylating an alkali chitin dope having a polymer concentration of 1% and an alkali concentration of 10% so that the deacetylation ratio becomes 40 to 60%, the ripening temperature is 25 to 30%. It is disclosed that 110 hours, 30 ° C. requires 20 to 50 hours, and 40 ° C. requires 10 to 30 hours, and there is a problem that aging requires a relatively long time.
【０００６】ここで、部分脱アセチル化した後、硫酸で
中和する場合には、部分脱アセチル化キチンは均一状態
を保つことができずにゲル化し、部分脱アセチル化キチ
ンゲルが沈殿する。この部分脱アセチル化キチンゲルの
脱水は、遠心分離により行われているが、多数回行う必
要があるために手間や時間がかかるのに加え、含水率を
８０重量％以下にはできないので、その後の乾燥に長時
間を要するという問題点がある。[0006] Here, when partially deacetylated and then neutralized with sulfuric acid, the partially deacetylated chitin gels without maintaining a uniform state, and a partially deacetylated chitin gel precipitates. Although the dehydration of the partially deacetylated chitin gel is performed by centrifugation, it requires a large number of times, so that it takes time and effort, and the water content cannot be reduced to 80% by weight or less. There is a problem that it takes a long time to dry.
【０００７】この発明は、以上のような事情や問題点に
鑑みてなされたものであり、原料となるキチン粉末の調
製を短縮化でき、アルカリキチンドープを調製した後の
濾過を不要とでき、しかもその後の熟成時間を短縮化で
きると共に、硫酸中和により沈殿する部分脱アセチル化
キチンゲルの脱水を効率良く行える非晶質の水溶性部分
脱アセチル化キチンの製造方法を提供することを目的と
する。The present invention has been made in view of the above circumstances and problems, and can shorten the preparation of chitin powder as a raw material, and can eliminate the need for filtration after preparing an alkali chitin dope. Moreover, it is an object of the present invention to provide a method for producing an amorphous water-soluble partially deacetylated chitin capable of shortening the subsequent aging time and efficiently dehydrating a partially deacetylated chitin gel precipitated by neutralization with sulfuric acid. .
【０００８】[0008]
【課題を解決するための手段】上記目的を達成するため
の手段とするところは、第１に、タンパク質含量が０．
１重量％以下、無機物含量が０．０１重量％以下の高純
度キチンを５０℃以下で均一系においてアルカリ加水分
解する際に、アルカリキチンドープの粘度を４００cps
以下として、キチンの脱アセチル化率が３５乃至６５％
となるように部分脱アセチル化し、次いで酸で中和する
か又はアルコール類、イオン交換樹脂等で脱アルカリす
ることにある。Means for achieving the above object are as follows. First, the protein content is set to 0.1.
When high-purity chitin having an inorganic content of 1 wt% or less and an inorganic content of 0.01 wt% or less is alkali-hydrolyzed in a homogeneous system at 50 ° C or less, the viscosity of the alkali chitin dope is increased to 400 cps.
The deacetylation rate of chitin is 35 to 65%
Partial deacetylation and then neutralization with an acid or dealkalization with an alcohol, ion exchange resin or the like.
【０００９】第２に、前記部分脱アセチル化した後、硫
酸中和により沈殿する部分脱アセチル化キチンゲルを圧
搾によって脱水することにある。Secondly, the partially deacetylated chitin gel which precipitates after neutralization with sulfuric acid after the partial deacetylation is dehydrated by pressing.
【００１０】[0010]
【発明の実施の形態】以下、この発明の実施形態につい
て説明する。この実施形態に係る非晶質の水溶性部分脱
アセチル化キチンの製造方法は、タンパク質含量が０．
１重量％以下、無機物含量が０．０１重量％以下の高純
度キチンを５０℃以下で均一系においてアルカリ加水分
解する際に、アルカリキチンドープの粘度を４００cps
以下として、キチンの脱アセチル化率が３５乃至６５％
となるように部分脱アセチル化し、次いで酸で中和する
か又はアルコール類、イオン交換樹脂等で脱アルカリす
るものである。Embodiments of the present invention will be described below. The method for producing the amorphous water-soluble partially deacetylated chitin according to this embodiment has a protein content of 0.1%.
When alkali-hydrolyzing high-purity chitin having an inorganic content of 1 wt% or less and an inorganic content of 0.01 wt% or less in a homogeneous system at 50 ° C or less, the viscosity of the alkali chitin dope is increased to 400 cps.
The deacetylation rate of chitin is 35 to 65%
And then neutralized with an acid or dealkalized with an alcohol, an ion exchange resin or the like.
【００１１】即ち、まず、高純度キチン粉末を所定濃度
のアルカリ水溶液に分散させ、これに氷を加えて攪拌す
るか、又は、分散液を直接凍結し、次に解凍する操作を
繰り返して、アルカリキチンドープを調製する。That is, first, high-purity chitin powder is dispersed in an aqueous alkaline solution having a predetermined concentration, and ice is added thereto and stirred, or the operation of directly freezing the dispersion and then thawing is repeated to obtain an alkaline aqueous solution. Prepare chitin dope.
【００１２】前記高純度キチンは、天然物由来のキチン
からタンパク質及びＣａＣＯ3 等の無機物を除去して、
タンパク質含量を０．１重量％以下、且つ、無機物含量
を０．０１重量％以下としたものである。このような高
純度キチンとしては、例えば、キチンＴｃ−Ｌ（商品
名，ユニチカ社製，人口皮膚用）等を好適に使用でき
る。The high-purity chitin is obtained by removing proteins and inorganic substances such as CaCO 3 from chitin derived from a natural product,
The protein content is 0.1% by weight or less and the inorganic content is 0.01% by weight or less. As such high-purity chitin, for example, chitin Tc-L (trade name, manufactured by Unitika, for artificial skin) and the like can be suitably used.
【００１３】前記アルカリ水溶液としては、アルカリ金
属水酸化物、アルカリ土類金属水酸化物、炭酸アルカリ
金属塩等の水溶液を使用すればよいが、特にＮａＯＨ、
ＫＯＨの水溶液が望ましい。As the alkaline aqueous solution, an aqueous solution of an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal carbonate or the like may be used.
An aqueous solution of KOH is preferred.
【００１４】前記アルカリキチンドープの粘度は、ポリ
マー濃度やアルカリ濃度等を適宜調整して、４００cps
以下、好ましくは３００cps 以下となるように調製すれ
ばよい。なお、このアルカリキチンドープには、生成す
る部分脱アセチル化キチンの分子量低下を抑えるため
に、チオフェノールやＮａＢＨ4 等をあらかじめ添加し
ておいてもよい。The viscosity of the alkali chitin dope is adjusted to 400 cps by appropriately adjusting the polymer concentration, the alkali concentration and the like.
It should be adjusted to be below, preferably below 300 cps. Note that thiophenol, NaBH 4, or the like may be added to the alkali chitin dope in advance in order to suppress a decrease in the molecular weight of the generated partially deacetylated chitin.
【００１５】ここで、このアルカリキチンドープを調製
する際の原料としては、上記のような高純度キチン粉末
を使用しているので、その粒度が５０メッシュより粗い
場合でも効率良くアルカリキチンドープを調製でき、そ
のため、粉砕の手間や時間等を従来より節約できるとい
う利点がある。また、アルカリキチンドープを調製した
後においては、濾過を行わないでそのまま熟成させるこ
とができるという利点もある。Here, since the high purity chitin powder as described above is used as a raw material for preparing the alkali chitin dope, even when the particle size is coarser than 50 mesh, the alkali chitin dope can be efficiently prepared. Therefore, there is an advantage that the labor and time for grinding can be saved more than before. Further, after the alkali chitin dope is prepared, there is also an advantage that it can be aged directly without filtering.
【００１６】前記アルカリキチンドープの調製段階でも
既にキチンの脱アセチル化率が２０％程度となっている
ので、脱アセチル化率を３５〜６５％とするには、更に
このアルカリキチンドープを５０℃以下、好ましくは４
０℃以下、より好ましくは３０℃以下で所定時間熟成さ
せる。Since the deacetylation ratio of chitin is already about 20% even in the preparation step of the alkali chitin dope, the alkali chitin dope is further heated to 50 ° C. in order to make the deacetylation ratio 35-65%. Below, preferably 4
Aging is carried out at 0 ° C. or lower, more preferably at 30 ° C. or lower for a predetermined time.
【００１７】このように、５０℃以下で熟成させるので
均一系の状態を保持できると共に、温和な条件で脱アセ
チル化するので、部分脱アセチル化キチンの分子量低下
を抑えることができる。また、この条件におけるアルカ
リキチンドープの粘度を４００cps 以下としているの
で、キチンの脱アセチル化率が３５乃至６５％となるま
でに要する熟成時間を従来よりも短縮化できるという利
点がある。As described above, aging at a temperature of 50 ° C. or less can maintain a homogeneous system, and deacetylation under mild conditions can suppress a decrease in the molecular weight of partially deacetylated chitin. Further, since the viscosity of the alkali chitin dope under these conditions is set to 400 cps or less, there is an advantage that the aging time required until the deacetylation rate of chitin becomes 35 to 65% can be shortened as compared with the conventional case.
【００１８】次いで、脱アセチル化率が３５乃至６５％
となった部分脱アセチル化キチンのアルカリ水溶液を塩
酸等の酸で中和するか、又は、アルコール類、イオン交
換樹脂等で脱アルカリする。その後、アセトン、メタノ
ール等の有機溶媒中に滴下すれば水溶性部分脱アセチル
化キチンが沈殿してくるので、これを濾別し、水−メタ
ノール混合溶媒で充分に洗浄して脱塩することによっ
て、精製品を得ることができる。Next, the deacetylation rate is 35 to 65%.
The alkali aqueous solution of the partially deacetylated chitin thus obtained is neutralized with an acid such as hydrochloric acid, or dealkalized with an alcohol, an ion exchange resin or the like. After that, if it is dropped into an organic solvent such as acetone or methanol, water-soluble partially deacetylated chitin is precipitated, and this is separated by filtration, washed sufficiently with a water-methanol mixed solvent and desalted. , You can get refined products.
【００１９】前記酸による中和を硫酸により行う場合に
は、均一状態を保持できずに部分脱アセチル化キチンゲ
ルが沈殿するが、これを濾過した後、湯洗等で脱塩して
圧搾することにより脱水すれば、比較的短時間で脱水で
きると共に、含水率を従来の８０重量％以上から７０重
量％程度以下にまで低下させることができるので、その
後の乾燥をより短縮化できるという利点がある。When the neutralization with the acid is carried out with sulfuric acid, a partially deacetylated chitin gel precipitates without maintaining a uniform state. After filtration, this is filtered, desalted by washing with hot water and pressed. In this case, the dehydration can be performed in a relatively short time, and the water content can be reduced from the conventional 80% by weight or more to about 70% by weight or less, so that there is an advantage that the subsequent drying can be further shortened. .
【００２０】なお、上記により得られる部分脱アセチル
化キチンは、Ｎ−アセチル−Ｄ−グルコサミン単位の含
量が３５乃至６５％、Ｄ−グルコサミン単位の含量が６
５乃至３５％であり、ランダムに脱アセチル化された非
晶質物質である。そのため、脱アセチル化率が３５〜６
５％とされたこの部分脱アセチル化キチンは、冷水、氷
水、及び水に溶解する。従って、種々の用途に使用する
ことができる。The partially deacetylated chitin thus obtained has an N-acetyl-D-glucosamine unit content of 35 to 65% and a D-glucosamine unit content of 6%.
5 to 35%, which is an amorphous substance which is randomly deacetylated. Therefore, the deacetylation rate is 35 to 6
This partially deacetylated chitin, made up to 5%, dissolves in cold, ice and water. Therefore, it can be used for various applications.
【００２１】[0021]
【実施例】次に、この発明を実施例により更に詳細に説
明するが、この発明は係る実施例に限定されるものでは
ない。Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
【００２２】４８％ＮａＯＨ１２１ｋｇに水２０Ｌ、４
３メッシュの高純度キチン粉末（商品名：キチンＴｃ−
Ｌ，ユニチカ社製，人口皮膚用）１０ｋｇを加え、４０
℃で４時間分散させた。その後、氷２３０ｋｇを加えて
２時間攪拌し、水２００Ｌと、前記ＮａＯＨに対して
０．０３％のＮａＢＨ4 を加え、加温してポリマー濃度
略１％、アルカリ濃度略１０％、粘度３００cps のアル
カリキチンドープを調製した後、３０℃で所定時間熟成
して部分脱アセチル化を行った。20 kg of water in 121 kg of 48% NaOH,
3-mesh high-purity chitin powder (trade name: Chitin Tc-
L, manufactured by Unitika Ltd., for artificial skin)
Dispersed at 4 ° C. for 4 hours. Thereafter, 230 kg of ice was added and the mixture was stirred for 2 hours, 200 L of water and 0.03% of NaBH 4 with respect to the NaOH were added, and the mixture was heated to have a polymer concentration of about 1%, an alkali concentration of about 10%, and a viscosity of 300 cps. After preparing the alkali chitin dope, it was aged at 30 ° C. for a predetermined time to perform partial deacetylation.
【００２３】次いで、脱アセチル化反応終了後、高粘度
溶液濾過器（株式会社ニッセン製，水平濾板型スパーク
ラーフィルター）により濾過し、９５％硫酸水溶液で中
和した。この際に沈殿した部分脱アセチル化キチンゲル
をゲル濾過圧搾機（薮田機械社製，特殊フィルタープレ
ス）により濾過した後、３回湯洗して脱塩し、次いで圧
搾した。次に、この脱水後の部分脱アセチル化キチンゲ
ルを温風で充分乾燥した後、粉砕して製品とした。After completion of the deacetylation reaction, the mixture was filtered with a high-viscosity solution filter (a horizontal filter plate type sparkler filter manufactured by Nissen Corporation) and neutralized with a 95% aqueous sulfuric acid solution. The partially deacetylated chitin gel precipitated at this time was filtered with a gel filtration press (manufactured by Yabuta Kikai Co., Ltd., special filter press), washed with hot water three times, desalted, and then pressed. Next, the partially deacetylated chitin gel after dehydration was sufficiently dried with warm air, and then pulverized to obtain a product.
【００２４】また、熟成時間を変えると共に、原料キチ
ン粘度の異なる高純度キチン粉末も使用して上記と同様
の操作を行った。なお、得られた製品の粘度についても
それぞれ測定した。その結果を次の表１に示す。The same operation as described above was performed by changing the aging time and using high-purity chitin powder having a different raw material chitin viscosity. In addition, the viscosity of each of the obtained products was also measured. The results are shown in Table 1 below.
【００２５】[0025]
【表１】 [Table 1]
【００２６】[0026]
【発明の効果】以上のように、請求項１の発明によれ
ば、原料としてタンパク質含量が０．１重量％以下、無
機物含量が０．０１重量％以下の高純度キチンを使用し
ているので、その粉末の粒度は５０メッシュより粗くて
もよく、そのため、粉砕の手間や時間等を従来より節約
することができる。このように、原料となるキチン粉末
の調製を短縮化できると共に、アルカリキチンドープを
調製した後、濾過を行わないでそのまま熟成させること
ができるので、非晶質の水溶性部分脱アセチル化キチン
の生産効率が良いという利点がある。As described above, according to the first aspect of the present invention, high-purity chitin having a protein content of 0.1% by weight or less and an inorganic substance content of 0.01% by weight or less is used as a raw material. The particle size of the powder may be coarser than 50 mesh, so that the labor and time for pulverization can be saved more than before. Thus, the preparation of chitin powder as a raw material can be shortened, and after preparing an alkali chitin dope, it can be aged as it is without filtration, so that amorphous water-soluble partially deacetylated chitin can be prepared. There is an advantage that production efficiency is good.
【００２７】更に、５０℃以下で熟成させるので均一系
の状態を保持できると共に、温和な条件で脱アセチル化
するので、部分脱アセチル化キチンの分子量低下を抑え
ることができる。また、この条件におけるアルカリキチ
ンドープの粘度を４００cps以下としているので、キチ
ンの脱アセチル化率が３５乃至６５％となるまでに要す
る熟成時間を従来よりも短縮化できるという利点があ
る。Furthermore, since it is aged at 50 ° C. or lower, a homogeneous state can be maintained, and since deacetylation is performed under mild conditions, a decrease in the molecular weight of partially deacetylated chitin can be suppressed. Further, since the viscosity of the alkali chitin dope under these conditions is 400 cps or less, there is an advantage that the aging time required until the deacetylation rate of chitin becomes 35 to 65% can be shortened as compared with the conventional case.
【００２８】請求項２の発明によれば、硫酸中和により
沈殿する部分脱アセチル化キチンゲルを圧搾によって脱
水するので、比較的短時間で脱水できると共に、含水率
を従来の８０重量％以上から７０重量％程度以下にまで
低下させることができ、そのため、その後の乾燥をより
短縮化できるという利点がある。According to the second aspect of the present invention, the partially deacetylated chitin gel precipitated by neutralization with sulfuric acid is dewatered by pressing, so that it can be dewatered in a relatively short time and the water content can be reduced from 80% by weight or more to 70% by weight. It is possible to reduce the amount to less than about% by weight, and there is an advantage that subsequent drying can be further shortened.
Claims (2)
機物含量が０．０１重量％以下の高純度キチンを５０℃
以下で均一系においてアルカリ加水分解する際に、アル
カリキチンドープの粘度を４００cps 以下として、キチ
ンの脱アセチル化率が３５乃至６５％となるように部分
脱アセチル化し、次いで酸で中和するか又はアルコール
類、イオン交換樹脂等で脱アルカリすることを特徴とす
る非晶質の水溶性部分脱アセチル化キチンの製造方法。1. A high-purity chitin having a protein content of 0.1% by weight or less and an inorganic substance content of 0.01% by weight or less at 50 ° C.
When the alkali hydrolysis is carried out in a homogeneous system below, the viscosity of the alkali chitin dope is set to 400 cps or less, and the deacetylation rate of chitin is partially deacetylated so as to be 35 to 65%, and then neutralized with an acid or A method for producing an amorphous, water-soluble, partially deacetylated chitin, comprising dealkalization with an alcohol, an ion exchange resin or the like.
により沈殿する部分脱アセチル化キチンゲルを圧搾によ
って脱水することを特徴とする請求項１記載の非晶質の
水溶性部分脱アセチル化キチンの製造方法。2. The amorphous water-soluble partially deacetylated chitin according to claim 1, wherein the partially deacetylated chitin gel precipitated by neutralization with sulfuric acid after the partial deacetylation is dehydrated by pressing. Manufacturing method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9161223A JP2990248B2 (en) | 1997-06-18 | 1997-06-18 | Method for producing amorphous water-soluble partially deacetylated chitin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9161223A JP2990248B2 (en) | 1997-06-18 | 1997-06-18 | Method for producing amorphous water-soluble partially deacetylated chitin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH115803A true JPH115803A (en) | 1999-01-12 |
| JP2990248B2 JP2990248B2 (en) | 1999-12-13 |
Family
ID=15730975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9161223A Expired - Fee Related JP2990248B2 (en) | 1997-06-18 | 1997-06-18 | Method for producing amorphous water-soluble partially deacetylated chitin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2990248B2 (en) |
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|---|---|---|---|---|
| WO2001072140A2 (en) * | 2000-03-25 | 2001-10-04 | Cognis Deutschland Gmbh & Co. Kg | Biopolymers and production thereof with coupled product recovery |
| WO2003011912A1 (en) * | 2001-08-02 | 2003-02-13 | Advanced Biopolymers As | Chitosan preparation |
| CN1102153C (en) * | 2000-08-28 | 2003-02-26 | 李高霖 | Water-soluble chitosan and its capsules |
| CN1112368C (en) * | 2000-04-20 | 2003-06-25 | 武汉大学 | Water soluble chitosan separating and purifying method |
| JP2006176584A (en) * | 2004-12-21 | 2006-07-06 | Univ Kansai | Neutral chitosan hydrogel and its preparation method |
| JP2008220388A (en) * | 2006-02-14 | 2008-09-25 | Koyo Chemical Kk | Sponge hemostatic material made of amorphous partial deacetylated chitin salt, and method of manufacturing the same |
| JP2008544014A (en) * | 2005-06-14 | 2008-12-04 | ジェニス イーエイチエフ． | Composition of partially deacetylated chitin derivatives |
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| CN111320711B (en) * | 2020-04-28 | 2022-05-06 | 东华大学 | Chitosan with high deacetylation degree and high molecular weight and preparation method thereof |
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1997
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001072140A2 (en) * | 2000-03-25 | 2001-10-04 | Cognis Deutschland Gmbh & Co. Kg | Biopolymers and production thereof with coupled product recovery |
| WO2001072140A3 (en) * | 2000-03-25 | 2002-09-19 | Cognis Deutschland Gmbh | Biopolymers and production thereof with coupled product recovery |
| CN1112368C (en) * | 2000-04-20 | 2003-06-25 | 武汉大学 | Water soluble chitosan separating and purifying method |
| CN1102153C (en) * | 2000-08-28 | 2003-02-26 | 李高霖 | Water-soluble chitosan and its capsules |
| WO2003011912A1 (en) * | 2001-08-02 | 2003-02-13 | Advanced Biopolymers As | Chitosan preparation |
| JP2006176584A (en) * | 2004-12-21 | 2006-07-06 | Univ Kansai | Neutral chitosan hydrogel and its preparation method |
| JP2008544014A (en) * | 2005-06-14 | 2008-12-04 | ジェニス イーエイチエフ． | Composition of partially deacetylated chitin derivatives |
| JP2014221905A (en) * | 2005-06-14 | 2014-11-27 | ジェニス イーエイチエフ．Ｇｅｎｉｓ ｅｈｆ． | Composition of partially deacetylated chitin derivative |
| JP2008220388A (en) * | 2006-02-14 | 2008-09-25 | Koyo Chemical Kk | Sponge hemostatic material made of amorphous partial deacetylated chitin salt, and method of manufacturing the same |
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| Publication number | Publication date |
|---|---|
| JP2990248B2 (en) | 1999-12-13 |
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