JPH03164191A - Production of low-molecular weight chitosan - Google Patents
Production of low-molecular weight chitosanInfo
- Publication number
- JPH03164191A JPH03164191A JP31224790A JP31224790A JPH03164191A JP H03164191 A JPH03164191 A JP H03164191A JP 31224790 A JP31224790 A JP 31224790A JP 31224790 A JP31224790 A JP 31224790A JP H03164191 A JPH03164191 A JP H03164191A
- Authority
- JP
- Japan
- Prior art keywords
- molecular weight
- chitosan
- low molecular
- weight chitosan
- low
- 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.)
- Pending
Links
- 229920001661 Chitosan Polymers 0.000 title claims abstract description 63
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- 239000004365 Protease Substances 0.000 claims abstract description 7
- 108091005804 Peptidases Proteins 0.000 claims abstract description 6
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims abstract description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 9
- 235000013305 food Nutrition 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 108090000790 Enzymes Proteins 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 12
- 229940088598 enzyme Drugs 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 108010059892 Cellulase Proteins 0.000 description 4
- 241000238557 Decapoda Species 0.000 description 4
- 229940106157 cellulase Drugs 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 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 3
- 229920002101 Chitin Polymers 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000012790 confirmation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 235000019419 proteases Nutrition 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- 241000238424 Crustacea Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 230000000850 deacetylating effect Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- SRSPZLZVGPJHJH-UHFFFAOYSA-N pavine Chemical compound C1C2=CC(OC)=C(OC)C=C2C2CC(C=C(C(=C3)OC)OC)=C3C1N2 SRSPZLZVGPJHJH-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 108091005508 Acid proteases Proteins 0.000 description 1
- 108090000526 Papain Proteins 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940055729 papain Drugs 0.000 description 1
- 235000019834 papain Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
【発明の詳細な説明】
〔技術分野〕
この発明は、天然キチンを脱アセチル化して得られるキ
トサンを分解して、低分子量キトサンを製造する方法に
関する。DETAILED DESCRIPTION OF THE INVENTION [Technical Field] The present invention relates to a method for producing low molecular weight chitosan by decomposing chitosan obtained by deacetylating natural chitin.
エビ，カニ等の甲殻類の甲皮、きのこ、細菌細胞壁等か
ら得られるキチンを脱アセチル化することにより、工業
用，医薬用あるいは食品用等の蛋白質凝集剤や、整髪料
等の化粧品等として用いられるキトサンが製造される。By deacetylating chitin obtained from the shells of crustaceans such as shrimp and crabs, mushrooms, and bacterial cell walls, it can be used as a protein flocculant for industrial, pharmaceutical, and food applications, as well as cosmetics such as hair conditioners. The chitosan used is produced.
ところが、このようなキトサンは、一般に高分子量であ
り、溶液とした場合の粘度が高すぎて扱いにくいもので
あるため、高濃度の溶液を作ることができない。したが
って、このようなキトサンを工業的に使用する場合には
、多量の溶液が必要となるため作業性が悪い。たとえば
、通常の高分子量キトサンを希酸に溶解したものでは、
ｌ重量％（以下「％」と記す〉程度の溶液でも、低粘度
になることは少なく非常に高粘度である。However, such chitosan generally has a high molecular weight, and when made into a solution, the viscosity is too high and it is difficult to handle, so it is impossible to make a highly concentrated solution. Therefore, when such chitosan is used industrially, a large amount of solution is required, resulting in poor workability. For example, when ordinary high molecular weight chitosan is dissolved in dilute acid,
Even a solution of about 1% by weight (hereinafter referred to as "%") rarely has a low viscosity and has a very high viscosity.
また、高分子量のキトサンを整髪料として使用した場合
には、毛髪への吸着を充分に行うことができない。Furthermore, when high molecular weight chitosan is used as a hair styling agent, it cannot be sufficiently adsorbed onto the hair.
キトサンを溶解するために使用される希酸としては、高
分子量の有機酸は適しておらず、ギ酸や酢酸等の低分子
量の有機酸が最適であるが、このような低分子量の有機
酸は臭気が強いため、食品用あるいは整髪料等として使
用するには問題がある。As the dilute acid used to dissolve chitosan, high molecular weight organic acids are not suitable, and low molecular weight organic acids such as formic acid and acetic acid are most suitable; Due to its strong odor, it is problematic to use as a food or hair conditioner.
この発明は、以上の事情に鑑みてなされたものであって
、分子量分布が狭くて品質が均一な低分子量キトサンを
得る製法を提供することを目的としている。The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a manufacturing method for obtaining low molecular weight chitosan having a narrow molecular weight distribution and uniform quality.
以上の目的を達戒するため、この発明は、キトサンの水
溶液を、バパイン、セルラーゼおよび酸性プロテアーゼ
のうちの少なくとも１つによって分解反応させ、低分子
量化する低分子量キトサンの製法を要旨としている。In order to achieve the above object, the gist of the present invention is a method for producing low-molecular-weight chitosan, in which an aqueous solution of chitosan is subjected to a decomposition reaction with at least one of vapain, cellulase, and acidic protease to reduce its molecular weight.
以下に、この発明を、詳しく説明する。This invention will be explained in detail below.
この発明に使用されるキトサンは、通常の方法で得るよ
うにすればよい。すなわち、エビ，カニ等の甲殻類の甲
皮、きのこ，細菌細胞壁等から得られた天然キチンを、
水酸化ナトリウム，水酸化カリウム等の濃アルカリ中で
脱アセチル化反応させれば、キトサンのケン濁液が得ら
れる。そして、このキトサンのケン濁液を濾過して粉末
を得、これを水洗後乾燥すれば、キトサンの白色粉末と
なるのである。Chitosan used in this invention may be obtained by a conventional method. In other words, natural chitin obtained from the carapace of crustaceans such as shrimp and crabs, mushrooms, bacterial cell walls, etc.
If the deacetylation reaction is carried out in a concentrated alkali such as sodium hydroxide or potassium hydroxide, a suspension of chitosan can be obtained. The chitosan suspension is then filtered to obtain a powder, which is then washed with water and dried to obtain a white chitosan powder.
以上のようなキトサンを、水に分散させたあと、これに
、パバイン．セルラーゼおよび酸性プロテアーゼのうち
少なくとも１つの酵素を加え、加熱する。そうすると、
これらの酵素がキトサンを分解する分解反応を行い、低
分子量キトサンが得られる。After dispersing the chitosan as described above in water, it was mixed with pavine. At least one enzyme of cellulase and acid protease is added and heated. Then,
These enzymes perform a decomposition reaction that decomposes chitosan, yielding low-molecular-weight chitosan.
この分解反応の条件は、この発明では特に限定されない
が、たとえば、上記キトサンを分散させる水に、ギ酸，
酢酸，乳酸等の有機酸を配合して、そのｐ｝ｌを４〜５
にすることが好ましい。また加熱の温度は、４０〜６０
℃であることが好ましい。このようなｐＨならびに温度
の条件において、前記パバインやセルラーゼ，酸性プロ
テアーゼ等が最も活発な分解反応を行えるようになるか
らである。また、前記ギ酸，酢酸，乳酸等の有機酸は、
前述したように、高分子量のキトサンを溶解させるもの
であるため、反応液にこのような有機酸を配合すれば、
それによって、キトサンが溶かされて、水と均一相を形
或でき、反応がスムースに行える、と言う効果もある．
得られたキトサン水溶液を、エタノール，イソプロパノ
ール，アセトン等の有機溶媒や、水酸化ナトリウム水溶
液，水酸化カリウム水溶液等のアルカリ水溶液と混合さ
せて沈澱を生戒させたあと、この沈澱物を濾過して分取
し、水洗，乾燥させれば、低分子量キトサンが得られる
。Conditions for this decomposition reaction are not particularly limited in the present invention, but for example, formic acid,
By blending organic acids such as acetic acid and lactic acid, the p}l is 4 to 5.
It is preferable to Also, the heating temperature is 40 to 60
Preferably it is ℃. This is because under such pH and temperature conditions, the pavine, cellulase, acidic protease, etc. can perform the most active decomposition reaction. In addition, the organic acids such as formic acid, acetic acid, and lactic acid are
As mentioned above, since it dissolves high molecular weight chitosan, if such an organic acid is added to the reaction solution,
This also has the effect of dissolving the chitosan and forming a homogeneous phase with water, allowing the reaction to proceed smoothly. The obtained chitosan aqueous solution is mixed with an organic solvent such as ethanol, isopropanol, or acetone, or an alkaline aqueous solution such as a sodium hydroxide aqueous solution or a potassium hydroxide aqueous solution to remove the precipitate, and then the precipitate is filtered. By fractionating, washing with water, and drying, low molecular weight chitosan can be obtained.
このようにして酵素による特異的な分解によって得られ
た低分子量キトサンにおいては、単Ｉｆｆが微量しか含
まれず、分子量分布の幅が、５０００〜５００００と非
常に狭く、均一な製品を得ることができる．また、この
低分子量キトサンは、長期間保存しても、溶液が褐変し
てしまう恐れもない。The low-molecular-weight chitosan obtained by specific enzymatic decomposition in this way contains only a trace amount of single If, and has a very narrow molecular weight distribution of 5,000 to 50,000, making it possible to obtain a uniform product. ．． Moreover, this low molecular weight chitosan has no fear that the solution will turn brown even if stored for a long period of time.
つぎに、この発明について、詳しく説明する。Next, this invention will be explained in detail.
（６ｉ！認試験１）
種々の酵素のなかで、この発明で用いる酵素がキトサン
を分解するのに極めて有効であることが、以下の試験で
確認された。この確認試験は、第ｌ表に示した各酵素を
用いてキトサンの分解反応を行うことによりなされた。(6i! Certification Test 1) It was confirmed in the following test that the enzyme used in this invention is extremely effective in decomposing chitosan among various enzymes. This confirmation test was conducted by carrying out a decomposition reaction of chitosan using each enzyme shown in Table 1.
なお、第１表中のＵは、酵素の存在量を表す単位（酵素
単位）であって、一定条件のもとて１分間に基質１μｍ
ｏｌｅを反応させる酵素の量をＩＵで表す。基質分子中
に作用を受ける結合が２つ以上あるときは、その結合１
μ当量を反応させる酵素量とする。したがって、第１表
中の単位（Ｕ／ ｇ ］は、蛋白質１ｍｇあたりの酵素
単位数、すなわち、比活性をあらわしている。In addition, U in Table 1 is a unit expressing the amount of enzyme present (enzyme unit), and 1 μm of substrate per minute under certain conditions.
The amount of enzyme that reacts with ole is expressed in IU. When there are two or more bonds in the substrate molecule that are affected, bond 1
Let μ equivalent be the amount of enzyme to be reacted. Therefore, the unit (U/g) in Table 1 represents the number of enzyme units per mg of protein, that is, the specific activity.
試験方法は、まず、ビーカにキトサン末４ｇを秤量し、
そこに約４５℃の温水３９０ｍｌを加えて、前記キトサ
ン末を分散させ、１％キトサン分散液を得る。つぎに、
この分散液中に所定量の９０％乳酸を加えたあと、これ
を４５℃の恒温槽中に入れ３０分間保持した。この液中
に第１表に示した酵素０．２ｇ（基質であるキトサンに
対して５％）を加え、４時間反応させて低分子量キトサ
ンを得た。反応終了後、重量補正を行ってから、２０℃
での粘度を測定し分子量を算出した．なお、粘度測定に
あたっては、Ｂ型回転粘度計を使用し、６０ｒ．ｐ．ｍ
で測定を行った。The test method was to first weigh 4g of chitosan powder into a beaker,
390 ml of warm water at about 45° C. is added thereto to disperse the chitosan powder to obtain a 1% chitosan dispersion. next,
After adding a predetermined amount of 90% lactic acid to this dispersion, it was placed in a constant temperature bath at 45° C. and maintained for 30 minutes. 0.2 g of the enzyme shown in Table 1 (5% based on chitosan as a substrate) was added to this solution, and the mixture was reacted for 4 hours to obtain low molecular weight chitosan. After completing the reaction, perform weight correction and then heat to 20°C.
The viscosity was measured and the molecular weight was calculated. In addition, when measuring the viscosity, a B-type rotational viscometer was used, and the viscosity was measured at 60 r. p. m
The measurement was carried out.
結果を第２表に示す。The results are shown in Table 2.
（確認試験２）
低分子量キトサン水溶液の平均分子量と、その平均分子
量の低分子量キトサン水溶液の濃縮可能な濃度との関係
を知るために、以下の試験を行った。(Confirmation Test 2) In order to find out the relationship between the average molecular weight of a low molecular weight chitosan aqueous solution and the concentration at which the low molecular weight chitosan aqueous solution having the average molecular weight can be concentrated, the following test was conducted.
まず、第３表に示したように、濃度が１％であって、そ
れぞれ粘度が異なる低分子量キトサン水溶液を調製した
。これらの低分子量キトサン水溶液の粘度から、その極
限粘度を求め、シュタウジンガーの粘度式により低分子
量キトサンの重合度を算出し、その重合度にキトサンの
単位量を乗じて低分子量キトサンの平均分子量を得た。First, as shown in Table 3, low molecular weight chitosan aqueous solutions having a concentration of 1% and different viscosities were prepared. From the viscosity of these low molecular weight chitosan aqueous solutions, determine their intrinsic viscosity, calculate the degree of polymerization of low molecular weight chitosan using the Staudinger viscosity formula, and multiply the degree of polymerization by the unit amount of chitosan to calculate the average molecular weight of low molecular weight chitosan. I got it.
結果を第３表右欄に示す。The results are shown in the right column of Table 3.
以上のようにして求められた平均分子量を有する各低分
子量キトサンの水溶液を、エバポレータを使用して減圧
濃縮し、：ａ縮ができなくなった時点での水溶液の濃度
を測定した。結果を同じく第３表右欄に示す。The aqueous solution of each low molecular weight chitosan having the average molecular weight determined as described above was concentrated under reduced pressure using an evaporator, and the concentration of the aqueous solution was measured at the time when :a contraction was no longer possible. The results are also shown in the right column of Table 3.
第
３
表
第３表にみるように、低分子量キトサンの平均分子量と
、その濃縮可能な濃度の限界との間には、比例関係があ
ることがわかった。すなわち、低分子量キトサンの平均
分子量が小さければ小さい程高い濃度の水溶液が得られ
るのである。Table 3 As shown in Table 3, it was found that there is a proportional relationship between the average molecular weight of low molecular weight chitosan and the limit of its concentration. In other words, the lower the average molecular weight of low molecular weight chitosan, the higher the concentration of the aqueous solution obtained.
以上２つの確認試験の結果をふまえて、以下の実施例な
らびに比較例を作威した。Based on the results of the above two confirmation tests, the following examples and comparative examples were created.
（実施例１〜６）
キトサン１０ｇを蒸留水９９０ｍｌ中に分散させ、攪拌
しながら第４表に示した各或分を配合したあと、同表に
示した条件で反応を行った。反応終了後、この反応液を
エバポレータで２０〜３０％の濃度になるまで濃縮した
あと、イソプロビルアルコールまたはアセトンの中にこ
の濃縮液を投入し、沈澱物を得た。得られた沈澱物を濾
過して分取し、水洗，乾燥させて低分子量キトサンを得
た（比較例１）
酵素のかわりに過酸化水素を使用し、反応条件を７０℃
，２時間にした以外は、実施例１〜６と同様にして低分
子量キトサンを得た。(Examples 1 to 6) 10 g of chitosan was dispersed in 990 ml of distilled water, and the respective amounts shown in Table 4 were blended with stirring, followed by reaction under the conditions shown in the table. After the reaction was completed, the reaction solution was concentrated using an evaporator to a concentration of 20 to 30%, and then the concentrated solution was poured into isopropyl alcohol or acetone to obtain a precipitate. The obtained precipitate was collected by filtration, washed with water, and dried to obtain low molecular weight chitosan (Comparative Example 1) Hydrogen peroxide was used instead of enzyme, and the reaction conditions were 70°C.
Low molecular weight chitosan was obtained in the same manner as in Examples 1 to 6, except that the heating time was changed to 2 hours.
以上の実施例ならびに比較例で得られた低分子量キトサ
ンに対し、以下の各測定を行った。The following measurements were performed on the low molecular weight chitosan obtained in the above Examples and Comparative Examples.
１％水溶液の粘度：得られた低分子量キトサンを蒸留水
に溶解して１％水溶液を作製し、その粘度を測定した。Viscosity of 1% aqueous solution: The obtained low molecular weight chitosan was dissolved in distilled water to prepare a 1% aqueous solution, and its viscosity was measured.
平均分子量：上記粘度の測定値から、予備試験３と同様
にして、得られた低分子量キトサンの平均分子量を算出
した。Average molecular weight: The average molecular weight of the obtained low molecular weight chitosan was calculated from the above-mentioned viscosity measurement value in the same manner as in Preliminary Test 3.
褐変の有無：粘度測定と同様な１％水溶液を作製し、そ
れをｌケ月間放置して褐変の有無を観察した。Presence or absence of browning: A 1% aqueous solution similar to that used for viscosity measurement was prepared, and it was left to stand for one month to observe the presence or absence of browning.
以上の結果を第４表に示す。The above results are shown in Table 4.
第４表の結果より、この発明の低分子量キトサンの製法
である実施例１〜６は、いずれも、キトサンを低分子量
化できるばかりでなく、このようにして得られた低分子
量キトサンは、比較例１のものに比べて褐変のないもの
であったので、戒分中に単糖類が含まれておらず、分子
量分布が狭くて均一なものであることがわかった。From the results in Table 4, it can be seen that Examples 1 to 6, which are the methods for producing low molecular weight chitosan of the present invention, not only can reduce the molecular weight of chitosan, but also that the low molecular weight chitosan obtained in this way is Since there was no browning compared to that of Example 1, it was found that no monosaccharides were contained in the precipitate, and the molecular weight distribution was narrow and uniform.
この発明の低分子量キトサンの製法は、以上のようであ
り、キトサンの水溶液を、パパイン，セルラーゼおよび
酸性プロテアーゼのうちの少なくとも１つによって分解
反応させ、低分子量化するようになっており、分子量分
布が狭くて品質が均一な低分子量キトサンを得ることが
できるようになる。The method for producing low molecular weight chitosan of the present invention is as described above, in which an aqueous solution of chitosan is subjected to a decomposition reaction with at least one of papain, cellulase, and acidic protease to reduce the molecular weight, and the molecular weight distribution is This makes it possible to obtain low molecular weight chitosan with a narrow and uniform quality.
Claims (3)
反応させ、低分子量化する低分子量キトサンの製法。(1) A method for producing low-molecular-weight chitosan, in which an aqueous solution of chitosan is subjected to a decomposition reaction with protease to reduce its molecular weight.
で行う特許請求の範囲第１項記載の低分子量キトサンの
製法。(2) The method for producing low molecular weight chitosan according to claim 1, wherein the decomposition reaction is carried out under conditions of pH 4 to 5 and 40 to 60°C.
００である特許請求の範囲第１項または第２項記載の低
分子量キトサンの製法。(3) The molecular weight of low molecular weight chitosan is 5000 to 500
00. The method for producing low molecular weight chitosan according to claim 1 or 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31224790A JPH03164191A (en) | 1990-11-17 | 1990-11-17 | Production of low-molecular weight chitosan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31224790A JPH03164191A (en) | 1990-11-17 | 1990-11-17 | Production of low-molecular weight chitosan |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61208435A Division JPS6363388A (en) | 1986-09-04 | 1986-09-04 | Production of low molecular weight chitosan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03164191A true JPH03164191A (en) | 1991-07-16 |
Family
ID=18026938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31224790A Pending JPH03164191A (en) | 1990-11-17 | 1990-11-17 | Production of low-molecular weight chitosan |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03164191A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011236264A (en) * | 2010-05-06 | 2011-11-24 | Yaizu Suisankagaku Industry Co Ltd | Method for producing low molecular weight chitosan |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6363388A (en) * | 1986-09-04 | 1988-03-19 | Nitta Zerachin Kk | Production of low molecular weight chitosan |
-
1990
- 1990-11-17 JP JP31224790A patent/JPH03164191A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6363388A (en) * | 1986-09-04 | 1988-03-19 | Nitta Zerachin Kk | Production of low molecular weight chitosan |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011236264A (en) * | 2010-05-06 | 2011-11-24 | Yaizu Suisankagaku Industry Co Ltd | Method for producing low molecular weight chitosan |
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