JPH01215836A - Chitosan gel composition and its production - Google Patents
Chitosan gel composition and its productionInfo
- Publication number
- JPH01215836A JPH01215836A JP63043068A JP4306888A JPH01215836A JP H01215836 A JPH01215836 A JP H01215836A JP 63043068 A JP63043068 A JP 63043068A JP 4306888 A JP4306888 A JP 4306888A JP H01215836 A JPH01215836 A JP H01215836A
- Authority
- JP
- Japan
- Prior art keywords
- chitosan
- gel composition
- pyrolignous acid
- gel
- acid
- 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 55
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 14
- 239000000052 vinegar Substances 0.000 claims description 21
- 235000021419 vinegar Nutrition 0.000 claims description 21
- 239000003814 drug Substances 0.000 abstract description 11
- 229940079593 drug Drugs 0.000 abstract description 11
- 239000002537 cosmetic Substances 0.000 abstract description 10
- 235000013305 food Nutrition 0.000 abstract description 7
- 239000000243 solution Substances 0.000 abstract description 7
- 230000006196 deacetylation Effects 0.000 abstract description 6
- 238000003381 deacetylation reaction Methods 0.000 abstract description 6
- 239000002778 food additive Substances 0.000 abstract description 6
- 235000013373 food additive Nutrition 0.000 abstract description 6
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 8
- 239000000499 gel Substances 0.000 description 20
- 239000002023 wood Substances 0.000 description 10
- 229920002101 Chitin Polymers 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 244000005700 microbiome Species 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000238557 Decapoda Species 0.000 description 2
- CBOJBBMQJBVCMW-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;hydrochloride Chemical compound Cl.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO CBOJBBMQJBVCMW-BTVCFUMJSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- IUPHTVOTTBREAV-UHFFFAOYSA-N 3-hydroxybutanoic acid;3-hydroxypentanoic acid Chemical compound CC(O)CC(O)=O.CCC(O)CC(O)=O IUPHTVOTTBREAV-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229920013642 Biopol™ Polymers 0.000 description 1
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000850 deacetylating effect Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
Landscapes
- Jellies, Jams, And Syrups (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- General Preparation And Processing Of Foods (AREA)
Abstract
Description
【発明の詳細な説明】
(産業上の利用分野)
本発明は、キトサンゲル組成物に関し、特にキトサンと
木酢液とから成るキトサンゲル組成物及びその製造方法
に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a chitosan gel composition, and particularly to a chitosan gel composition comprising chitosan and wood vinegar, and a method for producing the same.
(従来の技術)
キチン(β−1,4−ポリ−N−アセチルグルコサミン
)は、カニ、エビなどの甲殻類、昆虫、きのこ及び微生
物の細胞壁に存在しており、年間1000億トン(推定
)も生物生産され、セルロースについで多く自然界に存
在する天然高分子である。(Prior art) Chitin (β-1,4-poly-N-acetylglucosamine) exists in the cell walls of crustaceans such as crabs and shrimp, insects, mushrooms, and microorganisms, and is estimated to reach 100 billion tons per year (estimated). It is also biologically produced and is the second most abundant natural polymer found in nature after cellulose.
キトサン(chitosan )は、このキチンを濃ア
ルカリで処理することによって得られるキチンの脱アセ
チル化物であり、グルコサミン(2−アミノ−D−グル
コース)からなる下記の一般式からなる塩基性多vM類
である。Chitosan is a deacetylated product of chitin obtained by treating this chitin with concentrated alkali, and is a basic multi-vM compound consisting of glucosamine (2-amino-D-glucose) with the following general formula. be.
近年、未利用資源の有効利用についての研究が盛んにな
るにつれ、キチン、キトサンについても研究がなされ、
多くの報告がなされている。例えば、キトサンが植物病
原性のカビの生育に対して影響を及ぼすこと〔ストエラ
セル等、フィットパソロギッシュ ツアイトシュリフト
(Stoessel et al、、 ″Phytop
atl+ologischeZeitschrift
” ) 、第111巻、第82〜89頁(1984年)
〕、キキチンが細菌の生育の及び増殖に効果のあること
(特開昭62−83877号)などの報告がある。In recent years, as research into the effective use of unused resources has become more active, research has also been conducted on chitin and chitosan.
Many reports have been made. For example, chitosan affects the growth of phytopathogenic molds [Stoessel et al., ``Phytop.
atl+ologische Zeitschrift
), Vol. 111, pp. 82-89 (1984)
], it has been reported that Kikitin is effective for the growth and proliferation of bacteria (Japanese Patent Application Laid-open No. 83877/1983).
また、キトサンのゲル化に関しても幾つかの報告がされ
ており、この中でキトサンゲルの利用法として、平野、
[別冊フードケミカル」、1.1 (1987年)には
、機能性紙食品素材、栄養素、酵素、有効微生物などの
固定化担体、或いは食品形成材として有用であることが
報告されている。In addition, there have been several reports regarding the gelation of chitosan, and among these, Hirano,
[Bessatsu Food Chemicals], 1.1 (1987) reports that it is useful as a functional paper food material, a carrier for immobilizing nutrients, enzymes, effective microorganisms, etc., or a food forming material.
さらに、キトサンゲルの製法については、キチンゲルと
する方法〔平野等、「バイオポリマー (Biopol
ymer) J 、第15巻、第1685頁(1976
年)]、及びその方法に従ってN−プロピオニル、N−
ヘキサノイル、N−オクタノイル、N−デカノイル、N
−ラウロイル、N−ベンゾイルキトサンゲルを調製する
方法が開示されている〔平野等、”Carbohyd、
Res、” 、 47.315 (1976)
;平野等、”Agric、 Biol、 Chem、”
、 39.1335 (1975);平野等、”Ag
ric、 Biol、 Chem、” + 41+ 1
547 (1977) i平野等、”8th Int
ernational Symposium on C
arbohydrate Chemistry I+
。Furthermore, regarding the manufacturing method of chitosan gel, a method for making chitin gel [Hirano et al., "Biopol.
ymer) J, vol. 15, p. 1685 (1976
], and according to that method N-propionyl, N-
hexanoyl, N-octanoyl, N-decanoyl, N
- A method for preparing lauroyl, N-benzoyl chitosan gel is disclosed [Hirano et al., “Carbohyd.
Res,” 47.315 (1976)
; Hirano et al., “Agric, Biol, Chem,”
, 39.1335 (1975); Hirano et al., “Ag
ric, Biol, Chem,” + 41+ 1
547 (1977) i Hirano et al., “8th Int.
National Symposium on C
Arbohydrate Chemistry I+
.
Kyoto、 August 16−20 (197
6) Abst、 p、766 )。Kyoto, August 16-20 (197
6) Abst, p. 766).
また、キトサンを酢酸に溶解した後ホルマリンを加えて
放置することでゲル化させる方法〔平野等、”Agri
c、 Biol、 Chem、” 、 41.1547
(1977) ) 、或いは同様の方法でグルタルア
ルデヒドゲルを製造する方法が開示されている。(発明
が解決しようとする問題点)
上記したように、キトサンは天然に多量に存在するキチ
ンを脱アセチル化して得られる塩基性多糖類であるので
、そのゲル化したキトサンゲルが、食品、化粧品、或い
は薬品素材として利用できれば、製造コストなどの面か
ら有利である。Another method is to dissolve chitosan in acetic acid and then add formalin and leave it to gel.
c, Biol, Chem,” 41.1547
(1977) ) or a similar method to produce glutaraldehyde gel. (Problems to be Solved by the Invention) As mentioned above, chitosan is a basic polysaccharide obtained by deacetylating chitin, which exists in large amounts in nature. Alternatively, if it can be used as a drug material, it would be advantageous in terms of manufacturing costs.
しかしながら、上記した従来の方法のキトサンゲルの調
製方法によれば、その製造工程において、食品、化粧品
、或いは薬品素材として好ましくない、例えばホルマリ
ンなどを使用するため、上記した食品、化粧品、或いは
薬品素材として利用するには、安全性の点で問題があっ
た。However, according to the above-mentioned conventional chitosan gel preparation method, the manufacturing process uses formalin, which is undesirable as a food, cosmetic, or drug material. There was a problem with safety when using it as such.
従って、食品添加物として認可されでいるもの、化粧品
として認可されているもの、或いは薬品素材として認可
されているもので、キトサンをゲル化できれば好都合で
ある。Therefore, it would be advantageous if chitosan could be gelled using a material that is approved as a food additive, a cosmetic, or a drug material.
(問題点を解決するための手段)
本発明は上述の問題点に鑑かみ発明なされたものであり
、本発明者等は、キトサンを木酢液、特に食品添加物、
化粧品、或いは薬品素材として認可されている木酢液に
溶解させることにより、容易にキトサンがゲル化するこ
とを見出し本発明を完成したものである。(Means for solving the problems) The present invention was made in view of the above-mentioned problems, and the present inventors have discovered that chitosan can be used as a wood vinegar solution, especially as a food additive.
The present invention was completed by discovering that chitosan easily gels by dissolving it in wood vinegar, which is approved as a cosmetic or drug material.
すなわち、本発明のキトサンゲル組成物は、キトサンを
木酢液中に加え熔解した後、所定の時間、所定温度で放
置することにより、溶解物をゲル化させて得られる、キ
トサンと木酢液とから成るキトサンゲル組成物である。That is, the chitosan gel composition of the present invention is made from chitosan and wood vinegar, which is obtained by adding chitosan to pyroligneous vinegar and melting it, and then allowing the melt to gel by standing at a predetermined temperature for a predetermined period of time. This is a chitosan gel composition consisting of:
本発明に使用するキトサンとしては、好ましくはその脱
アセチル化度が、60%以上のものを使用するが、脱ア
ザチル化度が60%未満のものを使用し木酢液に熔解し
た場合には、不溶物を生じてしまうので好ましくないか
らである。The chitosan used in the present invention preferably has a deacetylation degree of 60% or more, but if a chitosan with a deazacylation degree of less than 60% is used and is dissolved in pyroligneous vinegar, This is because insoluble matter is generated, which is not preferable.
また、使用する木酢液としてはいずれも使用可能である
が、好ましくは、食品添加物、化粧品、或いは薬品素材
として認可されているもの(好ましくは有機酸を、酢酸
として定量した場合に約3〜10%含み、pnが約1.
0〜3.0であるもの)を用い、好ましくは20〜10
0%木酢液を含む水溶液として用いるのが有利である(
下記参考側参照)。In addition, any wood vinegar can be used, but preferably one that is approved as a food additive, cosmetics, or drug material (preferably an organic acid with a concentration of about 3 to 30% when measured as acetic acid) Contains 10%, pn is approximately 1.
0 to 3.0), preferably 20 to 10
It is advantageous to use it as an aqueous solution containing 0% wood vinegar (
(See reference side below).
上記のように調製したキトサンを木酢液に加えて、室温
にて、好ましくは2時間以上撹拌溶解を行い、その後、
室温にて、所定時間静置すれば、褐色のキトサンゲル組
成物が得られる。Add the chitosan prepared as above to the wood vinegar solution, stir and dissolve at room temperature, preferably for at least 2 hours, and then
If left to stand for a predetermined time at room temperature, a brown chitosan gel composition will be obtained.
参考例 (キトサンゲル化に及ぼす主1−サンと木酢液
との割合)
0.5 g 、 1 g 、 2 g 、 3 g 、
4 g 、 5 g 。Reference example (ratio of main 1-san and wood vinegar on chitosan gelation) 0.5 g, 1 g, 2 g, 3 g,
4g, 5g.
6gのキトサン(脱アセチル化度90%)をそれぞれ、
木酢液([香味煙SF2に東海化成株式%式%
g、94g(原液〜10倍希釈)に加えて、室温にて、
約2時間撹拌溶解を行い、その後、室温にて、22時間
静置してキトサンのゲル化実験を行った。その結果を下
記の表に示した。ただし、ゲル化の判断は目視にて行っ
た。6 g of chitosan (degree of deacetylation 90%), respectively,
In addition to wood vinegar solution ([Tokai Kasei Co., Ltd. % formula % g, 94 g (undiluted solution ~ 10 times diluted) to flavor smoke SF2, at room temperature,
The mixture was stirred and dissolved for about 2 hours, and then left at room temperature for 22 hours to conduct a gelation experiment of chitosan. The results are shown in the table below. However, gelation was determined visually.
表 キトサンゲル1.(しこ及ぼすキトサンと木酢液と
の割合実施例1
キトサン(ヤエガキ醗酵技研株式会社製;脱アセチル化
度90%)3gを、200 ml容のビーカーに入れ
た木酢液(「香味煙SF 2J 、東海化成株式会社製
)の原液97 gに加えた後、室温にて撹拌溶解させ、
その後室温にて5時間静置すると、褐色のキトサンゲル
98.2 gが得られた。Table Chitosan gel 1. (Ratio of chitosan and pyroligneous vinegar) 3 g of chitosan (manufactured by Yaegaki Hakko Giken Co., Ltd.; degree of deacetylation 90%) was placed in a 200 ml beaker and mixed with pyroligneous vinegar (“Fragrance Smoke SF 2J, Tokai Kasei Co., Ltd.) was added to 97 g of stock solution, stirred and dissolved at room temperature,
Thereafter, when the mixture was allowed to stand at room temperature for 5 hours, 98.2 g of brown chitosan gel was obtained.
実施例2
キトサン(ヤエガキ醗酵技研株式会社製;脱アセチル化
度70%)2gを、200 +nj2容のビーカーに
入れた木酢液(「香味煙SF 2J 、東海化成株式会
社製)の2倍希釈液98 gに加えた後、室温にて撹拌
熔解させ、その後室温にて20時間静置すると、褐色の
キトサンゲル98.4 gが得られた。Example 2 2 g of chitosan (manufactured by Yaegaki Hakko Giken Co., Ltd.; degree of deacetylation 70%) was placed in a 200 + nj 2-volume beaker to make a 2-fold dilution of wood vinegar solution (Komai Smoke SF 2J, manufactured by Tokai Kasei Co., Ltd.) After adding the mixture to 98 g, the mixture was stirred and melted at room temperature, and then left to stand at room temperature for 20 hours to obtain 98.4 g of brown chitosan gel.
(効果)
本発明によるキトサンゲル組成物は、キトサンと、木酢
液、特に食品添加物、化粧品、或いは薬品素材として認
可されている木酢液とから成り、且つキトサンは天然に
多量に存在する物質であるキチンより得られるものであ
るので、食品、化粧品、或いは薬品素材として鑑がみれ
ば、安全性及び製造コストなどの面からもきわめて優れ
たものである。(Effect) The chitosan gel composition according to the present invention consists of chitosan and pyroligneous acid, especially pyroligneous vinegar, which is approved as a food additive, cosmetics, or drug material, and chitosan is a substance that exists in large amounts in nature. Since it is obtained from a certain chitin, it is extremely superior in terms of safety and manufacturing cost when used as a material for foods, cosmetics, or medicines.
さらに、本発明のキトサンゲル組成物は、上記食品、化
粧品、或いは薬品素材としてだけでなく、例えば微生物
などの培養培地などとしても利用が考えられるなど利用
分野の広い優れた組成物である。Furthermore, the chitosan gel composition of the present invention is an excellent composition that can be used not only as a food, cosmetic, or drug material, but also as a culture medium for microorganisms, etc., and has a wide range of applications.
また、本発明のキトサンゲル組成物の製造方法によれば
、天然に多量に存在する物質であるキチンより得られる
キトサンを木酢液、特に食品添加物、化粧品、或いは薬
品素材として認可されている木酢液に熔解し放置するだ
けで、キトサンと木酢液とから成るキトサンゲル組成物
が得られるので、簡単で且つ製造コストも低く工業的生
産に供し得る優れた製造方法である。In addition, according to the method for producing a chitosan gel composition of the present invention, chitosan obtained from chitin, a substance that exists in large amounts in nature, can be mixed with pyroligneous vinegar, especially pyroligneous vinegar, which is approved as a food additive, cosmetics, or drug material. Since a chitosan gel composition consisting of chitosan and pyroligneous vinegar can be obtained by simply dissolving it in a liquid and leaving it to stand, this is an excellent manufacturing method that is simple and has low manufacturing costs and can be used in industrial production.
Claims (2)
。(1) Chitosan gel composition consisting of chitosan and pyroligneous vinegar.
間、所定温度で放置することにより、溶解物をゲル化さ
せて、キトサンと木酢液とから成るキトサンゲル組成物
を得ることを特徴とするキトサンゲル組成物の製造方法
。(2) A chitosan gel composition consisting of chitosan and pyroligneous vinegar is obtained by adding chitosan to pyroligneous vinegar and dissolving it, and then leaving it at a predetermined temperature for a predetermined period of time to gel the dissolved material. A method for producing a chitosan gel composition.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63043068A JP2599415B2 (en) | 1988-02-24 | 1988-02-24 | Chitosan gel composition and method for producing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63043068A JP2599415B2 (en) | 1988-02-24 | 1988-02-24 | Chitosan gel composition and method for producing the same |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01215836A true JPH01215836A (en) | 1989-08-29 |
JP2599415B2 JP2599415B2 (en) | 1997-04-09 |
Family
ID=12653538
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP63043068A Expired - Lifetime JP2599415B2 (en) | 1988-02-24 | 1988-02-24 | Chitosan gel composition and method for producing the same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2599415B2 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5599916A (en) * | 1994-12-22 | 1997-02-04 | Kimberly-Clark Corporation | Chitosan salts having improved absorbent properties and process for the preparation thereof |
KR19990039747A (en) * | 1997-11-14 | 1999-06-05 | 한형수 | Manufacturing method of complex functional plant growth promoter |
WO2002011565A1 (en) * | 2000-07-27 | 2002-02-14 | Idebio, S.L. | Chitosan-based diet sauces |
JP2006045299A (en) * | 2004-08-03 | 2006-02-16 | Tottori Prefecture | Chitosan gel and method for producing chitosan gel |
-
1988
- 1988-02-24 JP JP63043068A patent/JP2599415B2/en not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5599916A (en) * | 1994-12-22 | 1997-02-04 | Kimberly-Clark Corporation | Chitosan salts having improved absorbent properties and process for the preparation thereof |
KR19990039747A (en) * | 1997-11-14 | 1999-06-05 | 한형수 | Manufacturing method of complex functional plant growth promoter |
WO2002011565A1 (en) * | 2000-07-27 | 2002-02-14 | Idebio, S.L. | Chitosan-based diet sauces |
ES2166724A1 (en) * | 2000-07-27 | 2002-04-16 | Idebio S L | Chitosan-based diet sauces |
JP2006045299A (en) * | 2004-08-03 | 2006-02-16 | Tottori Prefecture | Chitosan gel and method for producing chitosan gel |
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JP2599415B2 (en) | 1997-04-09 |
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