JPS62151430A - Production of porous beads of chitin - Google Patents
Production of porous beads of chitinInfo
- Publication number
- JPS62151430A JPS62151430A JP29707485A JP29707485A JPS62151430A JP S62151430 A JPS62151430 A JP S62151430A JP 29707485 A JP29707485 A JP 29707485A JP 29707485 A JP29707485 A JP 29707485A JP S62151430 A JPS62151430 A JP S62151430A
- Authority
- JP
- Japan
- Prior art keywords
- chitin
- solution
- emulsion
- emulsifier
- oil
- 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
- 229920002101 Chitin Polymers 0.000 title claims abstract description 48
- 239000011324 bead Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000839 emulsion Substances 0.000 claims abstract description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 11
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 11
- 239000000194 fatty acid Substances 0.000 claims abstract description 11
- 229930195729 fatty acid Natural products 0.000 claims abstract description 11
- -1 fatty acid esters Chemical class 0.000 claims abstract description 11
- 230000015271 coagulation Effects 0.000 claims abstract description 9
- 238000005345 coagulation Methods 0.000 claims abstract description 9
- 239000008187 granular material Substances 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- 239000003925 fat Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 235000019197 fats Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 230000001112 coagulating effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000001587 sorbitan monostearate Substances 0.000 description 2
- 229940035048 sorbitan monostearate Drugs 0.000 description 2
- 235000011076 sorbitan monostearate Nutrition 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000009777 vacuum freeze-drying Methods 0.000 description 2
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 229920000869 Homopolysaccharide Polymers 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Colloid Chemistry (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、キチンポーラスビーズの製造法に関するもの
である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing chitin porous beads.
キチンは、周知の様に無を推動物の甲殻類をはじめ、昆
虫類の外皮成分、菌類の細胞壁等に多く存在し、それら
より組織を構成している蛋白質、炭酸カルシウム等を除
いたものである。As is well known, chitin is present in abundance in crustaceans, insects, and cell walls of fungi. be.
キチンは、Ｎ−アセチル−Ｄ−グルコサミンを構成糖と
し、（１峠４）−β−グリコシド結合の直鎖ホモ多糖類
で、セルロース分子構造のＤ−グルコビラノース残基の
Ｃ−２位の水酸基が、アセトアミド基で置換された構造
を有するものである。Chitin is a linear homopolysaccharide with N-acetyl-D-glucosamine as a constituent sugar and a (1)-β-glycosidic bond, and is located at the C-2 position of the D-glucobylanose residue in the cellulose molecular structure. It has a structure in which the hydroxyl group is substituted with an acetamido group.
さらに、このキチンはアセトアミド基によって分子間に
強い水素結合を有しており、希酸、希アルカリ、一般有
機溶剤等に溶けず、熱にも安定である。Furthermore, this chitin has strong intermolecular hydrogen bonds due to acetamide groups, and is not soluble in dilute acids, dilute alkalis, general organic solvents, etc., and is stable under heat.
本発明者等は、キチンに対する種々の研究を重ねた結果
、ある凝固液によって容易に固体化し、キチンの粒状化
が可能であることを見出し、本発明を提供するに至った
ものである。すなわち。As a result of various studies on chitin, the present inventors discovered that chitin can be easily solidified and granulated by a certain coagulating liquid, and have now provided the present invention. Namely.
キチン溶液を、乳化剤を含む油脂又は脂肪酸エステル中
に加えて、エマルジョンを形成させ、次にこのエマルジ
ョンを凝固液中へ添加してキチンを粒状固体化させるこ
とを特徴とするキチンポーラスビーズの製造法である。A method for producing chitin porous beads, which comprises adding a chitin solution to oil or fat or fatty acid ester containing an emulsifier to form an emulsion, and then adding this emulsion to a coagulation solution to solidify chitin into granules. It is.
本発明に使用するキチン溶液としては、アセチル化度７
０％以−ヒ、好ましくは９０％前後のキチン、より好ま
しくは９０％以上に再アセチル化されたキチンを特定の
溶媒へ溶解したものが挙げられる。The chitin solution used in the present invention has a degree of acetylation of 7
Examples include chitin that has been reacetylated to 0% or more, preferably around 90%, and more preferably 90% or more, dissolved in a specific solvent.
キチンは、溶媒への溶解性を良くするため、蛋白質、炭
酸カルシウム等をよく除いたもので、通常精製されたキ
チンを使用するのが好ましい。In order to improve the solubility of chitin in solvents, proteins, calcium carbonate, etc. have been thoroughly removed from chitin, and it is usually preferable to use purified chitin.
キチンを溶解する溶媒としては、Ｎ、Ｎ−ジメチルアセ
トアミド又はＮ−メチルピロリドンと塩化リチウムとの
混合溶媒が挙げられる。Examples of the solvent for dissolving chitin include N,N-dimethylacetamide or a mixed solvent of N-methylpyrrolidone and lithium chloride.
Ｎ、Ｎ−ジメチルアセトアミド又はＮ−メチルピロリド
ンと塩化リチウムとを混合する場合、その割合は、塩化
リチウムが混合溶媒中に５〜１０％、好ましくは８〜１
０％存在するよう混合する。When N,N-dimethylacetamide or N-methylpyrrolidone and lithium chloride are mixed, the proportion of lithium chloride in the mixed solvent is 5 to 10%, preferably 8 to 1%.
Mix so that it is present at 0%.
さらにキチンをかかる混合溶媒に溶解する場合、その濃
度は、キチンが溶解しうる限り、特に限定するものでは
ないが、高濃度である方が好ましいヶ
本発明に使用する乳化剤を含む油脂又は脂肪酸エステル
としては、乳化剤として例えば非イオン界面活性剤を油
脂又は脂肪酸エステルに溶解したものが挙げられる。Furthermore, when chitin is dissolved in such a mixed solvent, the concentration is not particularly limited as long as chitin can be dissolved, but a high concentration is preferable. Examples of emulsifiers include those obtained by dissolving a nonionic surfactant in oil or fat or fatty acid ester.
非イオン界面活性剤としては、ソルビタンモノステアリ
ン酸エステル、ソルビタンモアオレイン酸エステル、
ソルビタンモノラウリン酸エステル等が挙げられる。Nonionic surfactants include sorbitan monostearate, sorbitan moreoleate,
Examples include sorbitan monolaurate.
非イオン界面活性剤を溶解する油脂としては菜種油、サ
フラワー油、大豆油、牛脂等が、脂肪酸エステルとして
はステアリン酸メチルエステル、オレイン酸メチルエス
テル等が、それぞれ挙げられ、これらの油脂又は脂肪酸
エステルは、単独又は２種以上混合してもかもわない。Examples of oils and fats that dissolve nonionic surfactants include rapeseed oil, safflower oil, soybean oil, beef tallow, etc., and examples of fatty acid esters include stearic acid methyl ester and oleic acid methyl ester. may be used alone or in combination of two or more.
乳化剤を油脂又は脂肪酸エステルに溶解する場合、その
割合は任意であるが、乳化剤が油脂又は脂肪酸エステル
中に０．５〜２．０％存在するよう溶解するのが好まし
い。When the emulsifier is dissolved in the oil or fat or fatty acid ester, the ratio is arbitrary, but it is preferable that the emulsifier is dissolved in the oil or fat or fatty acid ester in an amount of 0.5 to 2.0%.
本発明に使用する凝固液としては、キチンを溶解しえな
いケトン類例えばアセトン、メチルエチルケトン、又は
アルコール類例えばメタノール、エタノール等が挙げら
れる。Examples of the coagulating liquid used in the present invention include ketones that cannot dissolve chitin, such as acetone and methyl ethyl ketone, and alcohols, such as methanol and ethanol.
本発明にかかるキチンポーラスビーズの製造法は、前記
キチン溶液を、攪拌しながら前記乳化剤を含む油脂又は
脂肪酸エステル中に加えて、エマルジョンを形成させ、
次にこのエマルジョンを、攪拌しながら前記凝固液中へ
添加してキチンを粒状固体化させる方法である。The method for producing chitin porous beads according to the present invention includes adding the chitin solution to the oil or fat or fatty acid ester containing the emulsifier while stirring to form an emulsion.
Next, this emulsion is added to the coagulation solution while stirring to solidify the chitin into particles.
キチン溶液よりキチンを粒状固体化させる場合、キチン
溶液と乳化剤を含む油脂又は脂肪酸エステルとの混合割
合は、任意であるが、重量比でキチン溶液：乳化剤を含
む油脂又は脂肪酸エステル＝１：９〜５：５が好ましく
、さらにキチン溶液と凝固液との混合割合も任意である
が、重量比でキチン溶液：凝固液＝１＝９〜５：５が好
ましい。When solidifying chitin into granules from a chitin solution, the mixing ratio of the chitin solution and the fat or oil containing an emulsifier or fatty acid ester is arbitrary, but the weight ratio of chitin solution: fat or oil or fatty acid ester containing an emulsifier = 1:9 ~ The ratio of chitin solution to coagulation liquid is preferably 5:5, and the mixing ratio of chitin solution to coagulation liquid is arbitrary, but it is preferable that the weight ratio of chitin solution to coagulation liquid is 1=9 to 5:5.
このようにして得られたキチンポーラスビーズは、遠心
分ｇＩ等によって分離・捕集する。The chitin porous beads thus obtained are separated and collected by centrifugation gI or the like.
次にアルコール等の親木性溶媒で洗浄し、さらに水で洗
浄して、乾燥する。Next, it is washed with a wood-friendly solvent such as alcohol, further washed with water, and dried.
乾燥方法としては、そのまま真空乾燥又は凍結乾燥する
か、又はアルコール置換後クロロホルムもしくはベンゼ
ン置換を行ない真空乾燥又は凍結乾燥する方法等が挙げ
られる。Examples of the drying method include vacuum drying or freeze drying as is, or vacuum drying or freeze drying after alcohol substitution followed by chloroform or benzene substitution.
本発明の製造法に従って得られるキチンポーラスビーズ
は、天然キチンそのままであるから、各種化合物を反応
させて種々の反応基を導入することが可能であり、
従って、各種用途への応用が可能である。Since the chitin porous beads obtained according to the production method of the present invention are natural chitin as they are, it is possible to introduce various reactive groups by reacting with various compounds, and therefore, it is possible to apply them to various uses. .
次に、実施例により本発明の詳細な説明する。Next, the present invention will be explained in detail with reference to Examples.
実施例１゜
精ｔＡｍ粉末キチン（アセチル化度９２％；新日本化学
■製）２ｇを、塩化リチウム８％含有Ｎ 、 Ｎ−ジメ
チルアセトアミド２００ｇ中へ加え、約１０時間攪拌し
て完全に溶解させた。Example 1 2 g of refined tAm powder chitin (degree of acetylation 92%; manufactured by Shin Nippon Kagaku ■) was added to 200 g of N,N-dimethylacetamide containing 8% lithium chloride and stirred for about 10 hours to completely dissolve it. Ta.
このキチン溶Ｍ２０ｇを、ソルビタンモノヌテアリン酸
エステル１％含有大豆油６０ｍ１中へ、よく攪拌しなが
ら加えエマルジョンを形成させた。20 g of this chitin-soluble M was added to 60 ml of soybean oil containing 1% sorbitan mononutearate with thorough stirring to form an emulsion.
このエマルジョンをメタノール６００ｍ ｌ中へ、攪拌
しながら加えた。This emulsion was added to 600 ml of methanol with stirring.
析出した粒状固体化キチンを、分離・捕集してメタノー
ル中に約１日間浸漬、続いて蒸留水中に約１日間浸漬し
て、白色のポーラスキチン粒状物を得た。The precipitated granular solidified chitin was separated and collected, immersed in methanol for about 1 day, and then immersed in distilled water for about 1 day to obtain white porous chitin granules.
実施例２゜
実施例１のキチン溶液１０ｇを、ソルビタンモノステア
リン酸エステル１％含有オレイン酸メチルエステル８０
ｍ ｌ中へ、よく攪拌しながら加えエマルジョンを形
成させた。Example 2゜10 g of the chitin solution of Example 1 was mixed with 80 g of methyl oleate containing 1% sorbitan monostearate.
ml with thorough stirring to form an emulsion.
このエマルジョンをア七ドア３００ｍ１中へ、攪拌しな
がら加えた。This emulsion was added to 300 ml of A7 Door while stirring.
析出した粒状固体化キチンを１分離・捕集してエタノー
ル中に約１日間浸漬、続いて蒸留水中に約１日間浸漬し
て、白色のポーラスキチン粒状物を得た。The precipitated granular solidified chitin was separated and collected, immersed in ethanol for about 1 day, and then immersed in distilled water for about 1 day to obtain white porous chitin particles.
Claims (1)
に加えて、エマルジョンを形成させ、次にこのエマルジ
ョンを凝固液中へ添加してキチンを粒状固体化させるこ
とを特徴とするキチンポーラスビーズの製造法。A method for producing chitin porous beads, which comprises adding a chitin solution to oil or fat or fatty acid ester containing an emulsifier to form an emulsion, and then adding this emulsion to a coagulation solution to solidify chitin into granules. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29707485A JPS62151430A (en) | 1985-12-25 | 1985-12-25 | Production of porous beads of chitin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29707485A JPS62151430A (en) | 1985-12-25 | 1985-12-25 | Production of porous beads of chitin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62151430A true JPS62151430A (en) | 1987-07-06 |
Family
ID=17841867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29707485A Pending JPS62151430A (en) | 1985-12-25 | 1985-12-25 | Production of porous beads of chitin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62151430A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998051712A1 (en) * | 1997-05-14 | 1998-11-19 | Japan As Represented By Director General Of National Institute Of Sericultural And Entomological Science Ministry Of Agriculture, Forestry And Fisherries | Chitin beads, chitosan beads, processes for producing these beads, carriers made of these beads and processes for producing microsprodidian spores |
| US7517671B2 (en) | 2002-02-28 | 2009-04-14 | New England Biolabs, Inc. | Methods and compositions for concentrating secreted recombinant protein |
| US8408801B2 (en) | 2009-02-25 | 2013-04-02 | Mitsubishi Heavy Industries, Ltd. | Oiling nozzle for thrust bearing |
-
1985
- 1985-12-25 JP JP29707485A patent/JPS62151430A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998051712A1 (en) * | 1997-05-14 | 1998-11-19 | Japan As Represented By Director General Of National Institute Of Sericultural And Entomological Science Ministry Of Agriculture, Forestry And Fisherries | Chitin beads, chitosan beads, processes for producing these beads, carriers made of these beads and processes for producing microsprodidian spores |
| US7517671B2 (en) | 2002-02-28 | 2009-04-14 | New England Biolabs, Inc. | Methods and compositions for concentrating secreted recombinant protein |
| US8119390B2 (en) | 2002-02-28 | 2012-02-21 | New England Biolabs, Inc. | Methods and compositions for concentrating secreted recombinant proteins |
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