JPS6363388A - Production of low molecular weight chitosan - Google Patents
Production of low molecular weight chitosanInfo
- Publication number
- JPS6363388A JPS6363388A JP61208435A JP20843586A JPS6363388A JP S6363388 A JPS6363388 A JP S6363388A JP 61208435 A JP61208435 A JP 61208435A JP 20843586 A JP20843586 A JP 20843586A JP S6363388 A JPS6363388 A JP S6363388A
- Authority
- JP
- Japan
- Prior art keywords
- molecular weight
- chitosan
- low molecular
- weight chitosan
- aqueous solution
- 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
- 229920001661 Chitosan Polymers 0.000 title claims abstract description 62
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 17
- 239000004365 Protease Substances 0.000 claims abstract description 12
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 11
- 108010059892 Cellulase Proteins 0.000 claims abstract description 6
- 108090000526 Papain Proteins 0.000 claims abstract description 6
- 108091005804 Peptidases Proteins 0.000 claims abstract description 6
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims abstract description 6
- 230000002378 acidificating effect Effects 0.000 claims abstract description 6
- 229940106157 cellulase Drugs 0.000 claims abstract description 6
- 229940055729 papain Drugs 0.000 claims abstract description 6
- 235000019834 papain Nutrition 0.000 claims abstract description 6
- 235000019419 proteases Nutrition 0.000 claims abstract description 6
- 108090000790 Enzymes Proteins 0.000 abstract description 14
- 102000004190 Enzymes Human genes 0.000 abstract description 14
- 229940088598 enzyme Drugs 0.000 abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- 229920002101 Chitin Polymers 0.000 abstract description 4
- 238000003381 deacetylation reaction Methods 0.000 abstract description 2
- 230000006196 deacetylation Effects 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000238557 Decapoda Species 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000012790 confirmation Methods 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate 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
- 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
- 238000005259 measurement Methods 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
- 235000013305 food Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002772 monosaccharides Chemical class 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
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 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
- 239000004615 ingredient Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 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
- General Preparation And Processing Of Foods (AREA)
- Jellies, Jams, And Syrups (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cosmetics (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 carapace 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、−Ｓ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（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、
１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 has a high molecular weight in -S, and when it is made into a solution, the viscosity is too high to handle (it is difficult to handle), so it is not possible to make a highly concentrated solution. When 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.
以上の目的を達成するため、この発明は、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 papain, cellulase, and acidic protease to reduce its molecular weight.
以下に、この発明の詳細な説明する。The present 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
、パパイン、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 the chitosan as described above is dispersed in water, at least one enzyme selected from papain, cellulase and acidic protease is added thereto 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ｐＨ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、前記パパインやセルラーゼ、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、水と均一相を形成
でき、反応がスムースに行える、と言う効果もある。Conditions for this decomposition reaction are not particularly limited in the present invention, but for example, formic acid,
It is preferable to mix an organic acid such as acetic acid or lactic acid to adjust the pH to 4 to 5. The heating temperature is 40 to 60℃.
It is preferable that This is because under such pH and temperature conditions, papain, cellulase, acidic protease, etc. can perform the most active decomposition reaction. In addition, as mentioned above, organic acids such as formic acid, acetic acid, and lactic acid dissolve high-molecular-weight chitosan, so if such organic acids are added to the reaction solution, chitosan will be dissolved. It also has the effect of forming a homogeneous phase with water and allowing the reaction to occur smoothly.
得られたキトサン水溶液を、エタノール、イソプロパツ
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
せて沈澱を生成させたあと、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
。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 form a precipitate, and then this precipitate is filtered. By separating, 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、単糖類が微量しか含ま
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 through specific enzymatic decomposition in this way contains only trace amounts of monosaccharides 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.
（確認試験ｌ）
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１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。(Confirmation Test I) It was confirmed in the following test that the enzyme used in this invention is extremely effective among various enzymes in decomposing chitosan. This confirmation test was conducted by performing 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、比活性をあられしている。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、ビー力にキトサン末４ｇを秤量し、
そこに約４５℃の温水３９０ｍ１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℃の恒温層中に入れ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、５ Ｑｒ、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 the reaction was completed, the weight was corrected, and then 20
The viscosity at °C was measured and the molecular weight was calculated. In addition, when measuring the viscosity, a B-type rotational viscometer was used, and 5 Qr, p
, m.
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
箪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 Stausinger's viscosity formula, and multiply the degree of polymerization by the amount of chitosan available to calculate the average of low molecular weight chitosan. The molecular weight was obtained.
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？ｔＩを、エバポレ・−タを使用し
て減圧濃縮し、濃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。Is each low molecular weight chitosan soluble in water having the average molecular weight determined as above? tI was concentrated under reduced pressure using an evaporator, and the concentration of the aqueous solution was measured at the point when concentration could no longer be achieved. 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
らびに比較例を作成した。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９９０ｍ１中に分散させ、撹拌
しながら第４表に示した各成分を配合したあと、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シロ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 each component shown in Table 4 was 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％水溶液を作成し、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.
褐変の有無二粘度測定と同様な１％水溶液を作成し、そ
れを１ケ月間放置して褐変の有無を観察した。2. Presence of Browning A 1% aqueous solution similar to that used in the viscosity measurement was prepared and 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（、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、成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 all of Examples 1 to 6, which are the methods for producing low molecular weight chitosan of the present invention, can not only reduce the molecular weight of chitosan (low molecular weight chitosan obtained in this way: Since there was no browning compared to that of Comparative Example 1, it was found that no monosaccharides were contained in the ingredients and that 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)
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。(1) 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 papain, cellulase, and acidic 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 chitosan according to claim 1 or 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61208435A JPS6363388A (en) | 1986-09-04 | 1986-09-04 | Production of low molecular weight chitosan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61208435A JPS6363388A (en) | 1986-09-04 | 1986-09-04 | Production of low molecular weight chitosan |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31224790A Division JPH03164191A (en) | 1990-11-17 | 1990-11-17 | Production of low-molecular weight chitosan |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6363388A true JPS6363388A (en) | 1988-03-19 |
| JPH0157958B2 JPH0157958B2 (en) | 1989-12-08 |
Family
ID=16556159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61208435A Granted JPS6363388A (en) | 1986-09-04 | 1986-09-04 | Production of low molecular weight chitosan |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6363388A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0220292A (en) * | 1988-07-06 | 1990-01-23 | Agency Of Ind Science & Technol | Production of depolymerized chitosan |
| JPH02200196A (en) * | 1989-01-31 | 1990-08-08 | Nippon Kayaku Co Ltd | Production of low molecular weight chitosan |
| JPH03164191A (en) * | 1990-11-17 | 1991-07-16 | Nitta Gelatin Inc | Production of low-molecular weight chitosan |
| US5762992A (en) * | 1991-08-01 | 1998-06-09 | San-Ei Chemical Industries, Ltd. | Method of preventing a decrease in sweetness of thaumatin |
| KR100367992B1 (en) * | 1998-06-15 | 2003-05-16 | 주식회사 태평양 | Manufacturing method of oligochitosan |
| KR100473445B1 (en) * | 2001-05-10 | 2005-03-08 | 씨제이 주식회사 | cholesterol reducer and health food containing chitosan and ε-polylysine |
| CN115521960A (en) * | 2022-09-20 | 2022-12-27 | 山东海锋生物工程有限公司 | Production process for reducing non-enzymatic browning of chitosan oligosaccharide |
| JP2023135748A (en) * | 2022-03-16 | 2023-09-29 | 株式会社ショウワ | Chitosan oligomer fractionation method |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07246933A (en) * | 1994-03-08 | 1995-09-26 | Kyosan Electric Mfg Co Ltd | Point switch movement |
-
1986
- 1986-09-04 JP JP61208435A patent/JPS6363388A/en active Granted
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0220292A (en) * | 1988-07-06 | 1990-01-23 | Agency Of Ind Science & Technol | Production of depolymerized chitosan |
| JPH02200196A (en) * | 1989-01-31 | 1990-08-08 | Nippon Kayaku Co Ltd | Production of low molecular weight chitosan |
| JPH03164191A (en) * | 1990-11-17 | 1991-07-16 | Nitta Gelatin Inc | Production of low-molecular weight chitosan |
| US5762992A (en) * | 1991-08-01 | 1998-06-09 | San-Ei Chemical Industries, Ltd. | Method of preventing a decrease in sweetness of thaumatin |
| KR100367992B1 (en) * | 1998-06-15 | 2003-05-16 | 주식회사 태평양 | Manufacturing method of oligochitosan |
| KR100473445B1 (en) * | 2001-05-10 | 2005-03-08 | 씨제이 주식회사 | cholesterol reducer and health food containing chitosan and ε-polylysine |
| JP2023135748A (en) * | 2022-03-16 | 2023-09-29 | 株式会社ショウワ | Chitosan oligomer fractionation method |
| CN115521960A (en) * | 2022-09-20 | 2022-12-27 | 山东海锋生物工程有限公司 | Production process for reducing non-enzymatic browning of chitosan oligosaccharide |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0157958B2 (en) | 1989-12-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |