JPH0515728B2 - - Google Patents
Info
- Publication number
- JPH0515728B2 JPH0515728B2 JP60240896A JP24089685A JPH0515728B2 JP H0515728 B2 JPH0515728 B2 JP H0515728B2 JP 60240896 A JP60240896 A JP 60240896A JP 24089685 A JP24089685 A JP 24089685A JP H0515728 B2 JPH0515728 B2 JP H0515728B2
- Authority
- JP
- Japan
- Prior art keywords
- chitin
- porous
- water
- chitosan
- spherical
- 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 - Fee Related
Links
- 229920002101 Chitin Polymers 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 229920001661 Chitosan Polymers 0.000 claims description 15
- 239000000725 suspension Substances 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 230000007935 neutral effect Effects 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000007599 discharging Methods 0.000 claims description 4
- 238000006640 acetylation reaction Methods 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- 239000003637 basic solution Substances 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000021736 acetylation Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000002245 particle Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010299 mechanically pulverizing process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Description
本発明は、クロマトグラフイー用充填剤、固定
化生理活性物質担体、化粧品用基剤、医薬用助剤
等に極めて好適な超微小球状キチンの製造方法に
関するものである。
The present invention relates to a method for producing ultrafine spherical chitin that is extremely suitable for use as a filler for chromatography, a carrier for immobilized physiologically active substances, a base for cosmetics, an auxiliary agent for pharmaceuticals, and the like.
従来、キチンの超微小球状物を得る方法として
は、特開昭58−127736号公報の実施例に記載のよ
うにキチンの原料である蟹の外骨格を充分に水洗
した後、40℃で乾燥し、衝撃型粉砕器で100メツ
シユ、即ち147μmに粉末化して粉末キチンを得
る方法が、また、特開昭59−86640号公報には小
径オリフイスを通過させて、剪断力で粉砕させる
方法が記載されているが74μmが限度である。
又、特開昭57−139101号公報にはキチンを100
メツシユ以下に粉砕し、酢酸/メタノール混合液
に浸漬、洗浄、乾燥し、該粉末を塩酸浸清、水洗
後、苛性ソーダで処理するキチン粉末の製造法が
開示されているが、これは灰分を減らすことが目
的でキチン粉末の大きさは原料の大きさと何ら変
つていない。
Conventionally, as a method for obtaining ultrafine chitin spherules, as described in the example of JP-A-58-127736, the crab exoskeleton, which is the raw material for chitin, is sufficiently washed with water and then heated at 40°C. There is a method to obtain chitin powder by drying it and pulverizing it to 100 meshes, that is, 147 μm with an impact type pulverizer, and a method of passing it through a small-diameter orifice and pulverizing it by shearing force is described in Japanese Patent Application Laid-open No. 86640/1983. Although it is described, the limit is 74 μm. Also, in Japanese Patent Application Laid-open No. 57-139101, chitin is
A method for producing chitin powder is disclosed in which the powder is ground to a mesh size, immersed in an acetic acid/methanol mixture, washed, dried, the powder is soaked in hydrochloric acid, washed with water, and then treated with caustic soda, which reduces the ash content. For this purpose, the size of chitin powder is no different from the size of the raw material.
上述の如く、従来の方法によつて得られるキチ
ン粉末は、主として原料キチンを粉砕することに
よつて得られたものであるので、かなり粒径の大
きいもので、どちらかと言えば球状より不規則な
形態の粒子であり、これらの粒子状のものは凝集
し易く、分散性に欠けるものであつた。
本発明は、5μm以下の均一な球径をもつた分
散性に優れた超微小球状キチンを製造する方法を
提供することを目的とする。
As mentioned above, chitin powder obtained by conventional methods is obtained mainly by pulverizing raw material chitin, so the particle size is quite large, and if anything, it is irregular rather than spherical. These particles tended to aggregate and lacked dispersibility. An object of the present invention is to provide a method for producing ultrafine spherical chitin with a uniform spherical diameter of 5 μm or less and excellent dispersibility.
本発明においては、均一にして且つ球状の分散
性の良好な超微小球状キチンを得るために、まず
多孔性キチンを水中で微粉砕して分散液となし、
該キチン分散液を気体と共に高温雰囲気中に吐出
乾燥することにより超微小球状キチンを製造する
ものである。
本発明方法において使用する多孔性キチンは、
キチンを機械的に粉砕した原キチンではなく、キ
チン超微小粒子の懸濁液が得られるように、次に
述べるような方法によつて得られる多孔性キチン
を使用する。
即ち、キトサンを酸性溶液に溶解し、塩基性溶
液中で凝固再生させた後、中性になるまで充分水
洗して得た再生多孔性キトサンを、アルコールで
水を除去後、有機溶媒中でアセチル化試薬と接触
反応させ多孔性キチンとした後、再度アルコール
で洗浄後中性になるまで充分水洗して得られる多
孔性キチンを使用する。この多孔性キチンの製造
法は、本発明者が昭和60年10月1日付で先に特許
出願をなし、特開昭62−79201として公開された
発明による方法に基くものであり、キトサン、好
ましくは平均分子量が10000〜230000の低分子量
キトサンを酢酸、ジクロル酢酸、蟻酸等の単独若
しくは混合物の水溶液に溶解し、キトサン酸性水
溶液とする。このキトサン酸性水溶液を塩基性凝
固浴中で再生して再生キトサンを得る。即ち、水
酸化ナトリウム、水酸カリウム、炭酸ナトリウ
ム、炭酸カリウム、アンモニア、エチレンジアミ
ン等の塩基性物質水溶液よりなる塩基性凝固液中
に上記キトサン酸性水溶液を一定量ずつ落下せし
めると球状の再生多孔性キトサンが得られる。こ
のようにして得られた再生多孔性キトサンを中性
になるまで充分水洗してアルコールで水を除去
後、例えばエタノール中で無水酢酸を用いて反応
させN−アセチル化を行つて多孔性キチンを得
る。得られた多孔性キチンはアルコールで洗浄後
水洗し、ホモジナイザー等で微粉砕してキチン懸
濁液とする。この方法によると再生キトサンが多
孔性の球状体として得られ、従つてN−アセチル
化して得られたキチンも多孔性であるので微粉砕
を行つた場合に極めて容易に均一な懸濁液を得る
ことができる。
上記のようにして得られたキチン懸濁液は、
100〜180℃の高温雰囲気中に気体と共に吐出し、
乾燥させることによつて平均球径5μm以下の超
微小球状キチンを得ることができる。吐出された
キチン懸濁液は、分散媒である水の表面張力等に
よつて高温雰囲気中で乾燥される際に微小な球状
体が形成される。キチン懸濁液を吐出させる際に
は懸濁液の分散性を保持させることが好ましく、
ホモジナイザー等で撹拌しながら行うことができ
る。本発明方法により得られる超微小球状キチン
の球径は、高温雰囲気中に吐出させる時の気体の
吐出圧、懸濁液の吐出量及び懸濁液の濃度を適宜
調節することによつて任意に設定することができ
る。
In the present invention, in order to obtain uniform ultrafine spherical chitin with good spherical dispersibility, porous chitin is first pulverized in water to form a dispersion,
Ultrafine spherical chitin is produced by discharging and drying the chitin dispersion together with gas into a high temperature atmosphere. The porous chitin used in the method of the present invention is
In order to obtain a suspension of ultrafine chitin particles, porous chitin obtained by the method described below is used instead of raw chitin obtained by mechanically pulverizing chitin. That is, chitosan is dissolved in an acidic solution, coagulated and regenerated in a basic solution, and then thoroughly washed with water until it becomes neutral.The obtained regenerated porous chitosan is obtained by removing water with alcohol, and then acetyl in an organic solvent. After making porous chitin through a contact reaction with a chemical reagent, the porous chitin is washed again with alcohol and thoroughly washed with water until it becomes neutral. This method for producing porous chitin is based on the method according to the invention for which the present inventor previously filed a patent application on October 1, 1985, and which was published as JP-A-62-79201. Dissolves low-molecular-weight chitosan with an average molecular weight of 10,000 to 230,000 in an aqueous solution of acetic acid, dichloroacetic acid, formic acid, etc. alone or as a mixture to obtain an acidic chitosan aqueous solution. This acidic chitosan aqueous solution is regenerated in a basic coagulation bath to obtain regenerated chitosan. That is, when a certain amount of the chitosan acidic aqueous solution is dropped into a basic coagulation solution consisting of an aqueous solution of basic substances such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, ammonia, and ethylenediamine, spherical regenerated porous chitosan is formed. is obtained. The regenerated porous chitosan thus obtained is thoroughly washed with water until it becomes neutral, water is removed with alcohol, and then reacted with acetic anhydride in ethanol for N-acetylation to form porous chitin. obtain. The obtained porous chitin is washed with alcohol and then water, and pulverized using a homogenizer or the like to obtain a chitin suspension. According to this method, regenerated chitosan is obtained as a porous spherical body, and chitin obtained by N-acetylation is also porous, so it is very easy to obtain a uniform suspension when finely pulverized. be able to. The chitin suspension obtained as above is
Discharged with gas into a high temperature atmosphere of 100 to 180℃,
By drying, ultrafine spherical chitin with an average spherical diameter of 5 μm or less can be obtained. When the discharged chitin suspension is dried in a high-temperature atmosphere due to the surface tension of water, which is a dispersion medium, minute spherical bodies are formed. When discharging a chitin suspension, it is preferable to maintain the dispersibility of the suspension.
This can be done while stirring with a homogenizer or the like. The spherical diameter of the ultrafine spherical chitin obtained by the method of the present invention can be adjusted arbitrarily by appropriately adjusting the gas discharge pressure, the amount of suspension discharged, and the concentration of the suspension when discharged into a high-temperature atmosphere. Can be set to .
次に本発明の方法を実施例を挙げて説明する。
尚、実施例中に記載の部は全て重量部を表すもの
とする。又、実施例における球径の測定は走査型
電子顕微鏡(JEOL−JSM−T200 日本電子株
式会社製)を用いて写真にて行つた。
実施例
脱アセチル化度95%、平均分子量62000のキト
サン65gを酢酸32.5gを含む水935gに溶解して
25℃における粘度4000cpのキトサン酸性溶液を
得た。
これを10%苛性ソーダ、30%メタノール、60%
水からなる塩基性溶液中に孔径0.25m/mの吐出
孔より圧力下で一定量づつ落下させ凝固させた。
これを中性になるまで充分洗浄しキトサン粒状物
1を得た。
これをエタノールで4回処理(水をアルコール
で除去)した後、3倍モルの無水酢酸を用いて常
温で24時間反応させた。この操作を3回繰返した
後エタノールで洗浄、水洗し、0.5N苛性ソーダ
でエステル結合切断のため室温で1時間反応さ
せ、水洗した。該多孔性キチン100mlに水50mlを
加えてホモジナイザーで17000rpm4分間撹拌し、
水を更に100ml加え250mlの濃度2.6%の分散液と
した。これを14.0ml/minの流速で3.5Kg/cm2の加
圧空気と共に175℃の高温雰囲気中に吐出乾燥さ
せ、乾燥物をサイクロンコレクターで捕集し、平
均球径3μmの超微小球径キチン5.3gを得た。
球径分布を調べた結果は下記の通りであつた。
球径(μm) 5 4 3 2 1
球 数 11 14 35 15 10
総級数 85、平均球径3.01μm
Next, the method of the present invention will be explained by giving examples.
In addition, all parts described in the examples shall represent parts by weight. In addition, the measurement of the spherical diameter in the Examples was carried out by photographing using a scanning electron microscope (JEOL-JSM-T200 manufactured by JEOL Ltd.). Example: 65 g of chitosan with a degree of deacetylation of 95% and an average molecular weight of 62,000 was dissolved in 935 g of water containing 32.5 g of acetic acid.
A chitosan acidic solution with a viscosity of 4000 cp at 25°C was obtained. Add this to 10% caustic soda, 30% methanol, 60%
A fixed amount was dropped into a basic solution consisting of water under pressure through a discharge hole with a pore diameter of 0.25 m/m to solidify it.
This was sufficiently washed until it became neutral to obtain chitosan granules 1. This was treated with ethanol four times (water was removed with alcohol), and then reacted with 3 times the mole of acetic anhydride at room temperature for 24 hours. This operation was repeated three times, followed by washing with ethanol and water, reacting with 0.5N caustic soda at room temperature for 1 hour to cleave the ester bond, and washing with water. Add 50 ml of water to 100 ml of the porous chitin and stir with a homogenizer at 17,000 rpm for 4 minutes.
Another 100 ml of water was added to form a 250 ml dispersion with a concentration of 2.6%. This was discharged into a high-temperature atmosphere of 175℃ with 3.5Kg/ cm2 of pressurized air at a flow rate of 14.0ml/min to dry it, and the dried material was collected with a cyclone collector to form ultra-fine spheres with an average sphere diameter of 3μm. 5.3 g of chitin was obtained. The results of examining the sphere diameter distribution were as follows. Ball diameter (μm) 5 4 3 2 1 Number of balls 11 14 35 15 10 Total series 85, average ball diameter 3.01μm
本発明の方法は、キチンを微粉砕する際にキチ
ン超微小粒子の懸濁液が得られるように多孔性キ
チンを用いて水中で微分砕してこ懸濁液とし、該
懸濁液を気体と共に高温雰囲気中に吐出し乾燥す
ることによつて、吐出された懸濁液が乾燥する際
にほぼ球状の平均粒径が5μm以下の超微小球状
キチンを形成せしめるものである。本発明によつ
て得られた超微小球状キチンは、実施例に記載の
粒径分布から明らかなように粒度の揃つた球状の
ものであり、分散性の極めて優れたものであつて
粒子が凝集、接着することがないので、クロマト
グラフイー用充填剤、固定化生理活性物質担体、
化粧品用基剤、医薬用助剤等の各種用途に好適な
ものである。
In the method of the present invention, porous chitin is used to finely crush chitin in water so that a suspension of ultrafine chitin particles can be obtained when chitin is finely crushed, and the suspension is converted into a gaseous suspension. By simultaneously discharging the suspension into a high temperature atmosphere and drying it, when the discharged suspension dries, it forms ultrafine spherical chitin having a substantially spherical shape and an average particle size of 5 μm or less. As is clear from the particle size distribution described in the examples, the ultrafine spherical chitin obtained by the present invention is spherical with uniform particle size, and has extremely excellent dispersibility. Since it does not aggregate or adhere, it can be used as a packing material for chromatography, a carrier for immobilized physiologically active substances,
It is suitable for various uses such as cosmetic bases and pharmaceutical aids.
Claims (1)
で凝固再生させた後、中性になるまで充分水洗し
て得た再生多孔性キトサンをアルコールで水を除
去後、有機溶媒中でアセチル化試薬と接触反応さ
せ、多孔性キチンとした後、再度アルコールで洗
浄後中性になるまで充分水洗して得られる多孔性
キチンを微粉砕し水中に分散せしめてなる懸濁液
を、気体と共に高温零囲気中に吐出し、乾燥する
ことを特徴とする超微小球状キチンの製造方法。1 Chitosan is dissolved in an acidic solution, coagulated and regenerated in a basic solution, and then thoroughly washed with water until it becomes neutral. After removing water with alcohol, the regenerated porous chitosan obtained is mixed with an acetylation reagent in an organic solvent. After making porous chitin, the porous chitin is washed again with alcohol and thoroughly washed with water until it becomes neutral.The obtained porous chitin is finely pulverized and dispersed in water to form a suspension. A method for producing ultrafine spherical chitin characterized by discharging it into an ambient atmosphere and drying it.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP24089685A JPS62100534A (en) | 1985-10-28 | 1985-10-28 | Production of ultrafine spherical chitin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP24089685A JPS62100534A (en) | 1985-10-28 | 1985-10-28 | Production of ultrafine spherical chitin |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62100534A JPS62100534A (en) | 1987-05-11 |
JPH0515728B2 true JPH0515728B2 (en) | 1993-03-02 |
Family
ID=17066292
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP24089685A Granted JPS62100534A (en) | 1985-10-28 | 1985-10-28 | Production of ultrafine spherical chitin |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62100534A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0776287B2 (en) * | 1989-07-07 | 1995-08-16 | 日本水産株式会社 | Method for producing porous chitin molding |
JPH0768648B2 (en) * | 1991-02-20 | 1995-07-26 | 富士紡績株式会社 | Modified cellulose regenerated fiber |
FR2694894B1 (en) * | 1992-08-20 | 1994-11-10 | Coletica | Use of a transacylation reaction between an esterified polysaccharide and a polyamine or polyhydroxylated substance for the manufacture of microparticles, process and composition. |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51122100A (en) * | 1975-04-12 | 1976-10-25 | Yoshio Iwakura | A process for purifying denatured chitin by reprecipitation |
JPS60208302A (en) * | 1984-03-31 | 1985-10-19 | Unitika Ltd | Formed chitin product and its production |
-
1985
- 1985-10-28 JP JP24089685A patent/JPS62100534A/en active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51122100A (en) * | 1975-04-12 | 1976-10-25 | Yoshio Iwakura | A process for purifying denatured chitin by reprecipitation |
JPS60208302A (en) * | 1984-03-31 | 1985-10-19 | Unitika Ltd | Formed chitin product and its production |
Also Published As
Publication number | Publication date |
---|---|
JPS62100534A (en) | 1987-05-11 |
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