CN116925258A - 一种在水相高度分散的甲壳素制备方法及所制备的甲壳素 - Google Patents
一种在水相高度分散的甲壳素制备方法及所制备的甲壳素 Download PDFInfo
- Publication number
- CN116925258A CN116925258A CN202210327510.4A CN202210327510A CN116925258A CN 116925258 A CN116925258 A CN 116925258A CN 202210327510 A CN202210327510 A CN 202210327510A CN 116925258 A CN116925258 A CN 116925258A
- Authority
- CN
- China
- Prior art keywords
- chitin
- epoxypropanol
- aqueous solution
- prepared
- preparation
- 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 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- GJOWSEBTWQNKPC-UHFFFAOYSA-N 3-methyloxiran-2-ol Chemical compound CC1OC1O GJOWSEBTWQNKPC-UHFFFAOYSA-N 0.000 claims abstract description 31
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000008213 purified water Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000004108 freeze drying Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 238000000502 dialysis Methods 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000002537 cosmetic Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 230000000694 effects Effects 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 238000004113 cell culture Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000000017 hydrogel Substances 0.000 description 2
- 239000001257 hydrogen Chemical group 0.000 description 2
- 229910052739 hydrogen Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 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
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 230000002439 hemostatic effect Effects 0.000 description 1
- -1 hydroxypropyl Chemical group 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
Abstract
本发明公开了一种在水相高度分散的甲壳素制备方法及所制备的甲壳素。经过甲壳素的粉碎、溶解、环氧丙醇修饰和纯化,得到终产物环氧丙醇甲壳素。该法制备的环氧丙醇甲壳素在纯化水中具有良好的溶解性,浓度可达100mg/mL,明显不同于常见的不溶或难溶的甲壳素衍生物。环氧丙醇甲壳素将在生物医药、化妆品、可吸收材料等领域等方面可能具有广泛的应用前景。
Description
技术领域
本发明涉及一种在水相高度分散的甲壳素及其制备方法。
背景技术
甲壳素是一类天然线性多糖,其化学名称是2-乙酰氨基-(1,4)-β-葡萄糖。甲壳素主要存在于鱼虾蟹等动物外壳及真菌生物的细胞壁中,来源广阔。甲壳素是自然界中含量最高的天然高分子之一,仅次于纤维素,是数量最多的含氮有机物。甲壳素具有许多优异的性质,例如良好的生物相容性、低免疫原性、较好的止血性,在生物医药、可吸收材料等领域起着重要的作用。
但甲壳素及其衍生物的溶解性较差,这与其分子结构和化学组成息息相关。对甲壳素而言,其分子为线性高分子,分子链容易紧密堆砌,甲壳素分子间的非共价作用能够充分发挥,形成难溶或致密的结构(如甲壳素晶须)。同时,甲壳素的基本单元是葡萄糖,葡萄糖是一种两亲性结构(Chinese Chemical Letters 30(2019)587–591)。葡萄糖吡喃糖环的两侧分布着亲水的羟基和疏水的碳氢键,羟基和碳氢键的特定顺序使得葡萄糖间的非共价作用十分复杂,一般溶剂难以破坏这种交替排列的亲疏水作用,分子溶剂化难、溶解性变差。另外,甲壳素中葡萄糖的2位羟基被乙酰氨基取代,相邻的乙酰氨基之间容易发生氢键作用。当发生氢键作用后,乙酰氨基会变得疏水,进一步降低甲壳素的溶解性。总之,由于甲壳素的线性结构和分子间复杂的亲疏水作用,使甲壳素的溶解性较差。
相比甲壳素,甲壳素衍生物的溶解性虽有一定提升,但仍然较差。采用环氧类、卤代烃等试剂对甲壳素进行修饰,可以降低其分子堆砌的紧密性;修饰引入的官能团也可以在一定程度上提高甲壳素的溶剂化能力。总体上,绝大多数甲壳素衍生物的溶解性较差,少数衍生物可作为1%-3%质量分数的水凝胶,难以达到在水相体系里较好的分散性。
发明内容
本发明的目的是提供一种在水相高度分散的甲壳素制备方法,该法制备的环氧丙醇甲壳素具有在水相良好的分散性,在组织工程、细胞培养、化妆品III类医疗器械等方面具有广泛的应用前景。
本发明采用以下技术方案:一种在水相高度分散的甲壳素制备方法,其特征在于:包括以下步骤:
(1)甲壳素在碱性溶液中低温静置溶解,形成均一稳定的甲壳素水相溶液;
(2)将环氧丙醇(缩水甘油)按比例加入至甲壳素水溶液,搅拌反应;
(3)把步骤(2)所得的反应体系进行简单处理,进行透析、冻干,得到环氧丙醇甲壳素。
作为优选的方案,步骤(1)是甲壳素加入至碱性水溶液后,在4℃至-80℃下静置放置1-60天。碱性水溶液为无机碱/有机碱混合水溶液体系,无机碱可采用氢氧化锂、氢氧化钠、氢氧化钾、氢氧化铯的一种或几种,其在碱性水溶液中的质量分数在1.5%至25.5%。有机碱采用尿素,其在碱性水溶液中质量分数在0.5%至9.5%。
作为优先的方案,步骤(2)是将环氧丙醇加入至甲壳素碱性水溶液中,在0℃-40℃下搅拌反应1-14天。投料比例为:1.00g甲壳素对应20-200μL环氧丙醇。
作为优先的方案,步骤(3)是将反应后体系用纯化水稀释1-20倍后透析;再将透析液取出,用硫酸、盐酸、磷酸或硝酸将pH值调制1-5,再进行透析、冻干。
本发明的另一个目的是提供在水相能高度分散的甲壳素。为此,本发明采用以下技术方案:
一种环氧丙醇甲壳素,其特征在于它为采用上述的制备方法制备的甲壳素。
本发明制备的环氧丙醇甲壳素产品为白色海绵状固体,易吸潮。根据本发明的实验,将10mg、25mg、50mg、100mg环氧丙醇甲壳素分散于1毫升纯化水,10mg、25mg、50mg样品经震荡后快速溶解。100mg样品虽然难以快速溶解,但经过6小时静置后,也能形成均一稳定的体系。
本发明的环氧丙醇甲壳素在纯化水中具有很高的分散能力。相比以往的改性甲壳素,环氧丙醇甲壳素在高浓度(100mg/mL)下,也能达到均匀稳定的分散状态。该特征明显区别于羟丙基甲壳素、羟乙基甲壳素等甲壳素衍生物。甲壳素为天然材料,生物相容性好。系体内的氢氧化钠、尿素、未反应的环氧丙醇等小分子均可通过透析除去,环氧丙醇甲壳素的水溶液pH值在7-8,符合人体pH范围,可应用于组织工程、细胞培养、化妆品、III类医疗器械等领域。
以下结合附图和实施例对本发明做出进一步说明。
附图说明
图1是本发明制备的环氧丙醇甲壳素的红外谱图。
图2是10mg、25mg、50mg、100mg本发明制备的环氧丙醇甲壳素在纯化水中的分散效果图。
图3是10mg、25mg、50mg、100mg本发明制备的环氧丙醇甲壳素在纯化水中的丁达尔现象效果图。
具体实施方式
为了进一步理解本发明,下面结合实施例对本发明提供的,一种在水相高度分散甲壳素的制备方法进行具体描述。但本发明并不限于这些实施例,该领域技术人员在本发明核心指导思想下做出的非本质改进和调整,仍然属于本发明的保护范围。
实施例1,甲壳素溶液的制备
(1)甲壳素粉末制备。称取20.00g甲壳素,置于中药粉碎机中,研磨2分钟。取出磨碎的甲壳素,依次过20目和50目的筛网,得甲壳素粉末。
(2)碱性水溶液制备。精确称取129.42gNaOH,缓慢、多次加入1L纯化水中。待NaOH完全溶解、体系温度降至常温后,向溶液中加入47.06g尿素,搅拌溶解、冷却至室温。在碱性水溶液中,氢氧化钠的质量分数为11.0%,尿素的质量分数为4.0%,纯化水的质量分数为85%。
(3)甲壳素粉末的溶解分散。取2.00g甲壳素粉末,加入至1L碱性水溶液中,搅拌分散。将整个体系浸于-20℃低温介质中,处理24小时。取出后恢复至室温,再次浸于-20℃低温介质,静置16天,恢复至室温。
实施例2,环氧丙醇甲壳素的制备
准确量取100μL环氧丙醇,加入至50mL实施例1制备的甲壳素溶液中,搅拌反应2天。
实施例3,环氧丙醇甲壳素的制备
准确量取300μL环氧丙醇,加入至50mL实施例1制备的甲壳素溶液中,搅拌反应5天。
实施例4,环氧丙醇甲壳素的制备
准确量取600μL环氧丙醇,加入至50mL实施例1制备的甲壳素溶液中,搅拌反应10天。
实施例5,环氧丙醇甲壳素的纯化
向实施例2中的反应体系中,加入150mL纯化水,搅拌均匀。将体系在纯化水中透析4次,1天/次。取出纯化后的体系,用硫酸酸化至pH 1,再向纯化水中透析4次,1天/次,最后冷冻干燥。
实施例2-4制备的甲壳素均具备良好的水溶性。但在反应体系中存在差别。当环氧丙醇刚刚加入时,环氧丙醇与水溶液是两相。随着反应时间延长,实施例2体系趋向于澄清,实施例3出现轻微浑浊,实施例4体系明显浑浊。综合考虑产物水溶性及投料等因素,实施例2的条件较优。
实施例2、实施例3、实施例4环氧丙醇甲壳素的红外谱图较为相似,实施例2的红外谱图如图1所示。实施例2、实施例3、实施例4所得产品3%wt水溶液的pH值分别为8.07,8.00,7.88。取实施例2制备的环氧丙醇甲壳素10mg、25mg、50mg、100mg,分别加入1mL纯化水。10mg、25mg、50mg样品经5分钟震荡,可分散于纯化水。100mg环氧丙醇甲壳素较难快速分散,最初会形成水凝胶;当在4℃静置过夜后,得到均一稳定透明的分散体系。10mg、25mg、50mg、100mg环氧丙醇甲壳素样品与纯化水空白样品的效果图如图2所示。样品的丁达尔效应如图3所示,随样品浓度升高,激光光路越来越明显。
由此可见,少量环氧丙醇的修饰可以显著提高甲壳素的水溶性,最高浓度可达100mg/mL。通过本发明制备的环氧丙醇甲壳素具备甲壳素原有的生物相容性及可降解性;其水溶液pH值在7-8,符合人体生理活动的pH范围。相比甲壳素以及现有的大多数甲壳素衍生物,环氧丙醇甲壳素具有优异的水溶性和良好的生物安全性,可应用于组织工程、细胞培养、化妆品、III类医疗器械等领域。
Claims (5)
1.一种在水相高度分散的甲壳素制备方法,其特征在于:包括以下步骤:
(1)甲壳素在碱性溶液中低温静置溶解,形成均一稳定的甲壳素水相溶液;
(2)将环氧丙醇按比例加入至甲壳素水溶液,搅拌反应;
(3)把步骤(2)所得的反应体系进行简单处理,进行透析、冻干,得到环氧丙醇甲壳素。
2.根据权利要求1所述的制备方法,其特征在于:步骤(1)是甲壳素加入至碱性水溶液后,在4℃至-80℃下静置放置1-60天。
3.根据权利要求1所述的制备方法,其特征在于:步骤(2)是将环氧丙醇加入至甲壳素碱性水溶液中,在0℃-40℃下搅拌反应1-14天。
4.根据权利要求1所述的制备方法,其特征在于:步骤(3)是将反应后体系用纯化水稀释1-20倍后透析;再将透析液取出,用硫酸、盐酸、磷酸或硝酸将pH值调制1-5,再进行透析、冻干。
5.环氧丙醇甲壳素,其特征在于它为采用权利要求1-4所述的制备方法制备的甲壳素。
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210327510.4A CN116925258A (zh) | 2022-03-30 | 2022-03-30 | 一种在水相高度分散的甲壳素制备方法及所制备的甲壳素 |
US17/828,152 US11834524B2 (en) | 2022-03-30 | 2022-05-31 | Method for preparing chitin highly dispersible in aqueous phase and chitin prepared thereby |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210327510.4A CN116925258A (zh) | 2022-03-30 | 2022-03-30 | 一种在水相高度分散的甲壳素制备方法及所制备的甲壳素 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN116925258A true CN116925258A (zh) | 2023-10-24 |
Family
ID=88194745
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202210327510.4A Pending CN116925258A (zh) | 2022-03-30 | 2022-03-30 | 一种在水相高度分散的甲壳素制备方法及所制备的甲壳素 |
Country Status (2)
Country | Link |
---|---|
US (1) | US11834524B2 (zh) |
CN (1) | CN116925258A (zh) |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3958536B2 (ja) * | 2000-07-12 | 2007-08-15 | 大日精化工業株式会社 | 水性溶液組成物および物品の表面改質方法 |
CN108310460B (zh) * | 2018-02-02 | 2021-08-03 | 武汉大学 | 可注射高强度温敏性改性甲壳素基水凝胶及其制备方法和应用 |
-
2022
- 2022-03-30 CN CN202210327510.4A patent/CN116925258A/zh active Pending
- 2022-05-31 US US17/828,152 patent/US11834524B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
US11834524B2 (en) | 2023-12-05 |
US20230312763A1 (en) | 2023-10-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TW458987B (en) | Poly-β-1→4-N-acetylglucosamine | |
US20050053576A1 (en) | Glycosaminoglycan-polycation complex crosslinked with polyfunctional crosslinking agent and process for producing the same | |
CN103975949A (zh) | 一种壳聚糖碘液及其制备方法 | |
EP3367820A1 (en) | Preparation of modified cellulose and its derivatives | |
US8445671B2 (en) | Method for preparing polyanhydroglucuronic acid and/or salts thereof | |
Ikhtiyarova et al. | Obtaination of carboxymethylchitosan from inanimate bees and study of its properties by conductometry, UV-Spectroscopy | |
Singh et al. | Recent progress on modified gum katira polysaccharides and their various potential applications | |
EP1280829A1 (en) | Process for preparing chitosan particles | |
CN116925258A (zh) | 一种在水相高度分散的甲壳素制备方法及所制备的甲壳素 | |
CN107915850A (zh) | 含硒壳聚糖水凝胶及其制备、降解方法和应用 | |
CN101418049A (zh) | 一种透明质酸的制备方法 | |
US20230383099A1 (en) | Hydroxybutyl chitin, hydroxybutyl chitin hydrogel and preparation methods thereof | |
JP5646164B2 (ja) | 分岐キトサン誘導体 | |
CN105624245B (zh) | 一种胶原蛋白的修饰改性方法 | |
Chatterjee et al. | Preparation and characterization of lobster shell chitosan: Modification of | |
Yuldoshov et al. | Impact of cellulose supramolecular structure on its carboxymethylation reaction activity | |
CN114931588B (zh) | 银纳米粒卡那霉素抗菌水凝胶的制备方法 | |
CN112694546B (zh) | 一种两亲性壳聚糖衍生物及其制备方法 | |
KR100302158B1 (ko) | 키틴/키토산계 계면활성제 및 그 제조방법 | |
JP2511676B2 (ja) | ポリオキシエチレン化キチンの酸化物の製造方法 | |
KR100328974B1 (ko) | 수용성 베타키틴의 제조방법 및 그 제조방법에 의해 제조된 수용성 베타키틴을 포함하는 화장료 | |
CN118045220A (zh) | 一种Cur-PF127/SA-CS/PVA水凝胶复合材料及其制备方法与应用 | |
SU710918A1 (ru) | Способ получени раствора коллоидной серы | |
EP3253200A1 (en) | Synthetic antimycotic molecule and method for synthesising an antimycotic molecule | |
KR980009287A (ko) | 고순도 결정성 nocc의 제조방법 및 효소를 이용한 수용성 키토산의 분자량 조절방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |