JPH0157958B2 - - Google Patents
Info
- Publication number
- JPH0157958B2 JPH0157958B2 JP61208435A JP20843586A JPH0157958B2 JP H0157958 B2 JPH0157958 B2 JP H0157958B2 JP 61208435 A JP61208435 A JP 61208435A JP 20843586 A JP20843586 A JP 20843586A JP H0157958 B2 JPH0157958 B2 JP H0157958B2
- Authority
- JP
- Japan
- Prior art keywords
- chitosan
- molecular weight
- low molecular
- aqueous solution
- viscosity
- 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.)
- Expired
Links
- 229920001661 Chitosan Polymers 0.000 claims description 56
- 239000007864 aqueous solution Substances 0.000 claims description 17
- 239000004365 Protease Substances 0.000 claims description 10
- 238000000354 decomposition reaction Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 108010059892 Cellulase Proteins 0.000 claims description 5
- 108090000526 Papain Proteins 0.000 claims description 5
- 108091005804 Peptidases Proteins 0.000 claims description 5
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 229940106157 cellulase Drugs 0.000 claims description 5
- 229940055729 papain Drugs 0.000 claims description 5
- 235000019834 papain Nutrition 0.000 claims description 5
- 235000019419 proteases Nutrition 0.000 claims description 5
- 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 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 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
- 238000012790 confirmation Methods 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
- 229920002101 Chitin Polymers 0.000 description 3
- 230000000052 comparative effect Effects 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
- 235000005985 organic acids 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
- 235000011054 acetic acid Nutrition 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
- 238000001035 drying Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method 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)
Description
〔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。
〔背景技術〕
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。
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。したがつて、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。
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。
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。
〔発明の目的〕
この発明は、以上の事情に鑑みてなされたもの
であつて、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。
〔発明の開示〕
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つによつて
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。
以下に、この発明を、詳しく説明する。
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。
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。
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、それによつて、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。
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。
このようにして酵素による特異的な分解によつ
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。
つぎに、この発明について、詳しく説明する。
（確認試験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。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
つて、一定条件のもとで１分間に基質1μmoleを
反応させる酵素の量を1U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1μ当量を反応させる酵素量とする。したがつ
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。
[Technical Field] The present invention relates to a method for producing low molecular weight chitosan by decomposing chitosan obtained by deacetylating natural chitin. [Background technology] By deacetylating chitin obtained from the carapace of crustaceans such as shrimp and crabs, mushrooms, bacterial cell walls, etc., it can be used as a protein flocculant for industrial, pharmaceutical, or food use, hair styling products, etc. Chitosan, which is used in cosmetics, etc., is produced. 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 a dilute acid, even a solution of about 1% by weight (hereinafter referred to as "%") hardly has a low viscosity and has a very high viscosity. Furthermore, when high molecular weight chitosan is used as a hair styling agent, it cannot be sufficiently adsorbed onto the hair. 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. [Object of the Invention] The present invention has been made in view of the above circumstances, and an object thereof is to provide a manufacturing method for obtaining low molecular weight chitosan having a narrow molecular weight distribution and uniform quality. [Disclosure of the Invention] In order to achieve the above object, the present invention provides 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 the molecular weight. The gist is: This invention will be explained in detail below. Chitosan used in this invention may be obtained by a conventional method. In other words, if natural chitin obtained from the shells of crustaceans such as shrimp and crabs, mushrooms, and bacterial cell walls is subjected to a deacetylation reaction in a concentrated alkali such as sodium hydroxide or potassium hydroxide, chitosan can be quenched. A cloudy liquid is 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. After dispersing the above chitosan in water, adding at least one enzyme among papain, cellulase and acidic protease,
Heat. Then, these enzymes perform a decomposition reaction that decomposes chitosan, yielding low-molecular-weight chitosan. The conditions for this decomposition reaction are not particularly limited in the present invention, but for example, it is preferable to mix an organic acid such as formic acid, acetic acid, or lactic acid into the water in which the chitosan is dispersed to adjust its pH to 4 to 5. . Further, the heating temperature is preferably 40 to 60°C.
This is because under such PH and temperature conditions, papain, 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 chitosan with a high molecular weight is dissolved, if such an organic acid is added to the reaction solution, chitosan can be dissolved and form a homogeneous phase with water, and the reaction can proceed. It also has the effect of making it smoother. 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 the precipitate is filtered and separated. By taking the sample, washing it with water, and drying it, low molecular weight chitosan can be obtained. The low molecular weight chitosan obtained through specific enzymatic decomposition in this way contains only trace amounts of monosaccharides and has a molecular weight distribution range of 5000 to 5000.
50,000 and can obtain a very narrow and 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. Next, this invention will be explained in detail. (Confirmation Test 1) The following test confirmed that among various enzymes, the enzyme used in this invention is extremely effective in decomposing chitosan. This confirmation test is
The decomposition reaction of chitosan was carried out using each enzyme shown in Table 1. Note that U in Table 1 is a unit (enzyme unit) representing the amount of enzyme present, and 1 U represents the amount of enzyme that reacts 1 μmole of substrate in 1 minute under certain conditions. When there are two or more bonds in the substrate molecule that are affected, the amount of enzyme to be reacted is 1μ equivalent of the bonds. Therefore, the unit [U/g] in Table 1 represents the number of enzyme units per mg of protein, that is, the specific activity.
【表】
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0.2
ｇ（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、重量補正を行つてから、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
つては、Ｂ型回転粘度計を使用し、60r.p.mで測
定を行つた。
結果を第２表に示す。[Table] The test method is to first weigh 4 g of chitosan powder into a beaker, add 390 ml of warm water at about 45°C to disperse the chitosan powder, and obtain a 1% chitosan dispersion. Next, a predetermined amount of 90% lactic acid was added to this dispersion, which was then placed in a constant temperature bath at 45° C. and maintained for 30 minutes. In this solution, 0.2% of the enzyme shown in Table 1 is added.
g (5% based on the substrate chitosan),
The reaction was carried out for 4 hours to obtain low molecular weight chitosan. After the reaction was completed, the weight was corrected, the viscosity at 20°C was measured, and the molecular weight was calculated. The viscosity was measured using a B-type rotational viscometer at 60 rpm. The results are shown in Table 2.
【表】
（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、以下の試験を行つ
た。
まず、第３表に示したように、濃度が１％であ
つて、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、シユタウジ
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。結果を
第３表右欄に示す。
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、濃縮ができなくなつた時
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。[Table] (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 that average molecular weight can be concentrated, the following test was conducted. 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 Schyutausinger's viscosity formula, and calculate the average molecular weight of low molecular weight chitosan by multiplying the degree of polymerization by the unit amount of chitosan. I got it. The results are shown in the right column of Table 3. Each aqueous solution of low molecular weight chitosan having the average molecular weight determined as above 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.
【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つた。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。
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。
実施例 １〜６
キトサン10ｇを蒸留水990ml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つた。反応終了
後、この反応液をエバポレータで20〜30％の濃度
にまるまで濃縮したあと、イソプロピルアルコー
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。
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、以下の各測定を行つた。
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。
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。
褐変の有無：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。
以上の結果を第４表に示す。[Table] 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. That is,
The lower the average molecular weight of low molecular weight chitosan, the higher the concentration of the aqueous solution that can be obtained. Based on the results of the above two confirmation tests, the following examples and comparative examples were created. 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 a 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 filtered and fractionated,
After washing with water and drying, low molecular weight chitosan was obtained. Comparative Example 1 Low molecular weight chitosan was obtained in the same manner as in Examples 1 to 6, except that hydrogen peroxide was used instead of enzyme and the reaction conditions were 70° C. and 2 hours. The following measurements were performed on the low molecular weight chitosan obtained in the above Examples and Comparative Examples. 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. Average molecular weight: From the above viscosity measurement value, preliminary test 3
In the same manner as above, the average molecular weight of the obtained low molecular weight chitosan was calculated. 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. The above results are shown in Table 4.
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つによつて分解反応させ、低分子量化する
ようになつており、分子量分子が狭くて品質が均
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. It becomes possible to obtain low molecular weight chitosan with narrow molecular weight molecules and uniform quality.
Claims (1)
および酸性プロテアーゼのうちの少なくとも１つ
によつて分解反応させ、低分子量化する低分子量
キトサンの製法。 ２ 分解反応を、PH４〜５、40〜60℃の条件下で
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。 ３ 低分子量キトサンの分子量が、5000〜50000
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。[Scope of Claims] 1. A method for producing low-molecular-weight chitosan, which comprises subjecting an aqueous solution of chitosan to a decomposition reaction using at least one of papain, cellulase, and acidic protease to reduce its molecular weight. 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. 3 The molecular weight of low molecular weight chitosan is 5000 to 50000
A 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 JPS6363388A (en) | 1988-03-19 |
| JPH0157958B2 true 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 (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 |
Families Citing this family (7)
| 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 |
| JP2732107B2 (en) * | 1989-01-31 | 1998-03-25 | 日本化薬株式会社 | Method for producing low molecular weight chitosan |
| JPH03164191A (en) * | 1990-11-17 | 1991-07-16 | Nitta Gelatin Inc | Production of low-molecular weight chitosan |
| JP3105031B2 (en) * | 1991-08-01 | 2000-10-30 | 三栄源エフ・エフ・アイ株式会社 | How to prevent thaumatin from reducing sweetness |
| 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 |
-
1986
- 1986-09-04 JP JP61208435A patent/JPS6363388A/en active Granted
Cited By (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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6363388A (en) | 1988-03-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |