CN102174123B - Production method of water soluble flavone-chitosan derivative - Google Patents
Production method of water soluble flavone-chitosan derivative Download PDFInfo
- Publication number
- CN102174123B CN102174123B CN201110045503A CN201110045503A CN102174123B CN 102174123 B CN102174123 B CN 102174123B CN 201110045503 A CN201110045503 A CN 201110045503A CN 201110045503 A CN201110045503 A CN 201110045503A CN 102174123 B CN102174123 B CN 102174123B
- Authority
- CN
- China
- Prior art keywords
- chitosan
- ultrafiltration
- solution
- raw material
- volume
- 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
Abstract
The invention discloses a production method of a water soluble flavone-chitosan derivative, relating to a preparation method of a flavonoid uvioresistant active substance. The production method takes chitosan and a flavone compound as raw materials, and the product is prepared by the processes of preparing a small molecular chitosan solution, synthesizing a water soluble flavone-chitosan derivative, concentrating and the like. The invention has the advantages of simple method, simplicity of operation, simple equipment, mild reaction conditions, energy conservation, full utilization of material resources in the production process, no discharge of three wastes, benefit to environmental protection, low production cost and convenience of popularization and application; and the product is characterized by being freely soluble in water, having good moistening effect and the like. The product prepared by the invention can be extensively used in skin care cosmetics and medicaments for treating skin diseases.
Description
One, technical field
The invention belongs to the preparation daily use chemicals with function additive technology field, be specifically related to a kind of preparation method of flavonoid Ginkgo Biloba Leaf Extract actives.
Two, background technology
Ultraviolet ray can be divided into short-wave band (190～280nm), medium wave band (280～320nm) and long-wave band (320～400nm), what skin was damaged mainly is the ultraviolet ray of medium wave and long-wave band.The long-time direct projection skin of ultraviolet ray causes acute erythemal effect, causes flush, melanochrome to accumulate in a large number, and severe patient also can be with nauseating, oedema, decortication, fever etc.In addition, the skin of over-exposure under ultraviolet ray also possibly cause skin carcinoma.Thereby the skin that research and development alleviate uv damage has important use and is worth and vast market prospect with functional daily use chemicals raw material.
Many materials have the ultraviolet ability of opposing, and they absorb high-octane ultraviolet ray, and jumping through molecular entergy level makes it to low-yield conversion, become the short hertzian wave of low-energy heat energy or wavelength.Chromocor compound is the biomolecules of from plant, extracting, and kind reaches more than 2000 kinds, has the substruction of 2-phenyl chromone; The flavones molecular absorption ultraviolet ray of ground state; Become excited state, then, the energy of absorption is discharged gradually through intramolecular continuous conjugated double bond system; Again become ground state molecule, thus cancellation ultraviolet harm.Thereby many chromocor compounds that contain are used in the sun-proof cosmetics of everyday use.Because chromocor compound is water-soluble not high, in aqueous cosmetic, be prone to deposition, can only be used for the emulsion form makeup, still, the emulsion form makeup are opaque, stopped that again chromocor compound absorbs ultraviolet ray; In addition, chromocor compound is low to the avidity of skin, both has been unfavorable near skin surface, also runs off easily.So, develop good water solubility, can effectively improve its Ginkgo Biloba Leaf Extract effect with the affine chromocor compound verivate of skin.
The preparation method of existing flavonoid Ginkgo Biloba Leaf Extract actives; It like application number " the Herba Oxytropis falcatae total flavones is in the application of preparation in the sun-proof articles " patent of 200910117427.9; The preparation technology of disclosed Herba Oxytropis falcatae total flavones is to be raw material with the Herba Oxytropis falcatae, through dry, pulverize, distillation water boiling and extraction, macroporous resin adsorption, wash-out is dry and product.The main drawback of this technology is that product purity is low, contains impurity such as amino acid, carbohydrate; Raw material availability is low, and the product poorly water-soluble that makes joins and is prone to deposition in the makeup; The product moisture retention and the sterilizing ability that make are relatively poor, are prone to brown stain and receive microbial contamination; Distilled water extraction carries out under decocting condition, and temperature of reaction is higher, produces the power consumption height, is unfavorable for save energy; Production process produces waste liquid, and waste residue not only is unfavorable for the guard ring border but also has increased production cost.
Three, summary of the invention
The objective of the invention is deficiency to existing flavonoid Ginkgo Biloba Leaf Extract actives preparation method; A kind of working method of water-soluble flavone-chitosan derivatives is provided; This method have power consumption low, do not have " three wastes " discharging, no coupling product, product purity is high, production cost is low, is easy to characteristics such as popularization.
Principle of the present invention is: chitosan has antibiotic, anticancer, character such as preserve moisture.Molecular weight is less than the chitosan water soluble of 5000Da, because the chitosan free amine group is positively charged, can form electrostatic interaction with the negative charge carboxyl of skin collagen, effectively is attached to skin surface; This amino also can with the negative charge group effect of mikrobe, suppress its growth or sterilization; The free hydroxyl group of chitosan can be through forming hydrogen bond and the irreducible water molecule with water molecules, the performance moisture-keeping function; So small molecules chitosan and verivate thereof are widely used in the cosmetics of everyday use.
Chitosan and chromocor compound all have free hydroxyl group, under alkaline condition can with epoxide group generation etherification reaction, generate the water-soluble flavone-chitosan derivatives that connects with glycosidic link.
The present invention seeks to realize like this: a kind of working method of water-soluble flavone-chitosan derivatives; With chitosan and chromocor compound is raw material; Through preparation small molecules chitosan solution, synthesizing water-solubility flavones-chitosan derivatives, technology such as concentrate, just make water-soluble flavone-chitosan derivatives product.Its concrete grammar step is following:
(1) preparation small molecules chitosan solution
With commercially available molecular-weight average is that the chitosan of 45000Da～55000Da is a raw material; Quality (g) according to the chitosan raw material: mass concentration be the volume (mL) of 0.2%～0.5% hydrochloric acid soln than the ratio that is 1: 60～120, under agitation the chitosan raw material is added in the hydrochloric acid soln, after mixing; Using diluted sodium hydroxide solution to regulate its pH again is 5.5～6.0; Then add Remazol Brilliant Violet carboxymethyl chitin hydrolase again, under 50～60 ℃ temperature, reaction 1～2h.The Remazol Brilliant Violet carboxymethyl chitin hydrolase that adds: the mass ratio of chitosan raw material is 1: 50～100.Be warming up to 80～100 ℃ after reaction is accomplished, and keep pumping into whizzer after 10～20 minutes and carry out spinning, centrifuge speed is 6000 rev/mins～10000 rev/mins, and centrifugation time is 10～20 minutes, collects centrifugal clear liquid and deposition respectively.For deposition,, use X 1000 with being used to prepare daily use chemicals behind the protease hydrolysis because of containing the Remazol Brilliant Violet carboxymethyl chitin hydrolase of inactivation; For centrifugal clear liquid, use the sodium filter of molecular weight cut-off as 2000Da～4000Da, under 0.8～1.8Mpa pressure, carry out nanofiltration separation, collect nanofiltration filtered solution and trapped fluid respectively.For the nanofiltration trapped fluid, concentrate the back as wetting Agent for Printing Inks and antiseptic-germicide; For the nanofiltration filtered solution, be the small molecules chitosan solution of preparing, be used for synthesizing water-solubility flavones-chitosan derivatives.
(2) preparation flavones-chitosan derivative solution
After the completion of (1) step; Be that according to the quality (g) of chromocor compound: the volume of water (mL) adds chromocor compound in the entry than the ratio that is 1: 30～60 with chromocor compound (like Hesperidin or ginkgolic flavone glycoside or buckwheat flavonoids etc.) raw material; After mixing earlier; The pH that uses diluted sodium hydroxide solution to regulate it again is 9～11, and stir process 30～50 minutes, just prepares chromocor compound solution.Then according to chromocor compound solution: ethylene glycol diglycidylether: the mass ratio of the small molecules chitosan solution that (1) step prepared is 1: 1～3: 3～6 ratio; Chromocor compound solution is joined (1) to be gone on foot in the small molecules chitosan solution of preparing; It is 10～11.5 that the back use dilute sodium hydroxide that stirs is regulated pH; And when being warming up to 80～95 ℃, adding ethylene glycol diglycidylether again, afterreaction 1～3h stirs; Using Hydrogen chloride to regulate pH at last is 4～6, just prepares flavones-chitosan derivative solution.
(3) preparation flavones-chitosan derivatives liquid concentrator
After the completion of (2) step; Go on foot flavones-chitosan derivative solution of preparing with (2); Through molecular weight cut-off is the ultra-filtration membrane of 10000Da～30000Da, is to carry out ultrafiltration under 0.08～0.2Mpa at pressure, and until ultrafiltration trapped fluid volume is that 10% of original volume～30% o'clock ends.Collect ultrafiltration filtered solution and trapped fluid respectively.For the ultrafiltration trapped fluid; According to the ultrafiltration trapped fluid: USP Kosher: hundred mould volume ratios of killing sanitas are 1: 0.10～0.20: 0.01～0.05 ratio; In the ultrafiltration trapped fluid; Add USP Kosher and white mould and kill sanitas, mix, just prepare soluble solid concentration and be flavones-chitosan derivatives liquid concentrator of 35～40%; For the ultrafiltration filtered solution, be chromocor compound solution, contain the small molecules chitosan with next batch and the ethylene glycol diglycidylether mixing solutions mixes, be used to prepare flavones-chitosan derivative solution once more after concentrating.
After the present invention adopts technique scheme, mainly contain following effect:
(1) the present invention is a raw material with chromocor compound and chitosan, prepares a kind of water-soluble flavone-chitosan derivatives through ethylene glycol diglycidylether, and the product that makes is prone to be dissolved in the water, and humidity-holding effect is good.
(2) production technique adopts enzymic hydrolysis to prepare the technology of small molecules chitosan, and hydrolysising condition is gentle, and the hydrolyzate molecular weight is even; Adopt crosslinked chromocor compound of ethylene glycol diglycidylether and small molecules chitosan, reaction conditions is gentle, and cross-linking effect is good, save energy.
(3) utilization of resources is abundant.Material in production process of the present invention all adopts circular treatment, does not have " three wastes " discharging, makes the most of material resources, and has reduced cost, and has helped environment protection, is a kind of green production technology of lower production cost.
(4) the inventive method is simple, and is easy and simple to handle, and used production unit is simple, and production cost is low, and is easy to utilize.
The product that adopts the inventive method to prepare can be widely used in skin protection cosmetics and treats in the field such as dermopathic medicine.
Four, embodiment
Below in conjunction with embodiment, further specify the present invention.
Embodiment 1
A kind of working method of water-soluble flavone-chitosan derivatives, its concrete steps are following.
(1) preparation small molecules chitosan solution
With commercially available molecular-weight average is that the chitosan of 45000Da is a raw material; Raw materials quality (g) according to chitosan: mass concentration be the volume (mL) of 0.2% hydrochloric acid soln than the ratio that is 1: 60, under agitation the chitosan raw material is added in the hydrochloric acid soln, after mixing; Using diluted sodium hydroxide solution to regulate its pH again is 5.5; Then add Remazol Brilliant Violet carboxymethyl chitin hydrolase again, under 50 ℃ temperature, reaction 1h.The Remazol Brilliant Violet carboxymethyl chitin hydrolase that adds: the quality of chitosan raw material is 1: 50.Be warming up to 80 ℃ after reaction is accomplished, and keep pumping into whizzer after 10 minutes and carry out spinning, centrifuge speed is 6000 rev/mins, and centrifugation time is 10 minutes, collects centrifugal clear liquid and deposition respectively.For deposition,, use X 1000 with being used to prepare daily use chemicals behind the protease hydrolysis because of containing the Remazol Brilliant Violet carboxymethyl chitin hydrolase of inactivation; For centrifugal clear liquid, use the sodium filter of molecular weight cut-off as 2000Da, under 0.8Mpa pressure, carry out nanofiltration separation, collect nanofiltration trapped fluid and filtered solution respectively.For the nanofiltration trapped fluid, concentrate the back as wetting Agent for Printing Inks and antiseptic-germicide; For the nanofiltration filtered solution, be the small molecules chitosan solution of preparing, be used for synthesizing water-solubility flavones-chitosan derivatives.
(2) preparation flavones-chitosan derivative solution
After the completion of (1) step; With chromocor compound (being Hesperidin) is raw material, and according to the quality (g) of Hesperidin chromocor compound: the volume of water (mL) adds Hesperidin chromocor compound raw material in the entry than the ratio that is 1: 30; Earlier after mixing; Using diluted sodium hydroxide solution to regulate its pH again is 9, and stir process 30 minutes, just prepares chromocor compound solution.Then according to Hesperidin chromocor compound solution: ethylene glycol diglycidylether: the mass ratio of the small molecules chitosan solution that (1) step prepared is 1: 1: 3 a ratio; Hesperidin chromocor compound solution is joined (1) to be gone on foot in the small molecules chitosan solution of preparing; It is 10 that the back use dilute sodium hydroxide that stirs is regulated pH; And when being warming up to 80 ℃, adding ethylene glycol diglycidylether again, afterreaction 1h stirs; Using Hydrogen chloride to regulate pH at last is 4, just prepares Hesperidin flavones-chitosan derivative solution.
(3) preparation flavones-chitosan derivatives liquid concentrator
After (2) step accomplished, with flavones-chitosan derivative solution that (2) step prepared, it was the ultra-filtration membrane of 10000Da through molecular weight cut-off, is to carry out ultrafiltration under the 0.08Mpa at pressure, until ultrafiltration trapped fluid volume be 10% o'clock of original volume only.Collect ultrafiltration filtered solution and trapped fluid respectively.For the ultrafiltration trapped fluid; According to the ultrafiltration trapped fluid: USP Kosher: hundred mould volume ratios of killing sanitas are 1: 0.10: 0.01 ratio; In the ultrafiltration trapped fluid; Add USP Kosher and white mould and kill sanitas, mix, just prepare soluble solid concentration and be flavones-chitosan derivatives liquid concentrator of 35%; For the ultrafiltration filtered solution, be chromocor compound solution, contain the small molecules chitosan with next batch and the ethylene glycol diglycidylether mixing solutions mixes, be used for being used to once more prepare flavones-chitosan derivative solution after concentrating.
Embodiment 2
A kind of working method of water-soluble flavone-chitosan derivatives, with embodiment 1, wherein:
In (1) step, the molecular-weight average of chitosan raw material is 50000Da, and concentration of hydrochloric acid is 0.3%; The quality of chitosan raw material (g): hydrochloric acid soln volume (mL) is than being 1: 100, and pH is 5.8,55 ℃ of temperature of reaction; Reaction times 1.5h; Remazol Brilliant Violet carboxymethyl chitin hydrolase and chitosan mass were warming up to 90 ℃, 15 minutes hold-times than 1: 80.Centrifuge speed is 8000 rev/mins, and centrifugation time is 15 minutes, and sodium filter molecular weight cut-off is 3000Da, and pressure is 1.2Mpa.
In (2) step, chromocor compound (being ginkgolic flavone glycoside) is a raw material, the quality of ginkgetin compound (g): the volume of water (mL) is than being 1: 50; PH is 10, and 40 minutes stir process time, ginkgetin compound solution: ethylene glycol diglycidylether: the mass ratio of small molecules chitosan solution is 1: 2: 5; PH is 11; Be warming up to 90 ℃, reaction times 2h, reconciling pH is 5.
In (3) step; Ultrafiltration pressure is 0.14Mpa; The molecular weight cut-off of ultra-filtration membrane is 20000Da; Ultrafiltration to ultrafiltration trapped fluid volume be original volume 20% till, ultrafiltration trapped fluid: USP Kosher: hundred mould volume ratios of killing sanitas are 1: 0.15: 0.03, and the soluble solid concentration in flavones-chitosan derivatives liquid concentrator is 38%.
Embodiment 3
A kind of working method of water-soluble flavone-chitosan derivatives, with embodiment 1, wherein:
In (1) step, the molecular-weight average of chitosan raw material is 55000Da, and concentration of hydrochloric acid is 0.5%, the quality of chitosan raw material (g): hydrochloric acid soln volume (mL) is than being 1: 120; PH is 6.0,60 ℃ of temperature of reaction, reaction times 2h; Remazol Brilliant Violet carboxymethyl chitin hydrolase: chitosan mass was warming up to 100 ℃ than 1: 100,20 minutes hold-times; Centrifuge speed is 10000 rev/mins, and centrifugation time is 20 minutes, and sodium filter molecular weight cut-off is 4000Da.Pressure is 1.8Mpa.
In (2) step, chromocor compound (being buckwheat flavonoids) is a raw material, the quality of buckwheat flavonoids compound (g): the volume of water (mL) is than being 1: 60; PH is 11, and 50 minutes stir process time, buckwheat flavonoids compound solution: ethylene glycol diglycidylether: the mass ratio of the small molecules chitosan solution that (1) step prepared is 1: 3: 6; PH is 11.5; Be warming up to 95 ℃, reaction times 3h, reconciling pH is 6.
In (3) step; Ultrafiltration pressure is 0.2Mpa; The molecular weight cut-off of ultra-filtration membrane is 30000Da; Ultrafiltration to ultrafiltration trapped fluid volume be original volume 30% till, ultrafiltration trapped fluid: USP Kosher: hundred mould volume ratios of killing sanitas are 1: 0.20: 0.05, and the soluble solid concentration in flavones-chitosan derivatives is 40%.
Claims (4)
1. the working method of a water-soluble flavone-chitosan derivatives is characterized in that the concrete grammar step is following:
(1) preparation small molecules chitosan solution
With commercially available molecular-weight average is that the chitosan of 45000Da～55000Da is a raw material, and according to the quality of chitosan raw material: mass concentration is that the volume ratio of 0.2%～0.5% hydrochloric acid soln is the ratio of 1g: 60～120mL, under agitation the chitosan raw material is added in the hydrochloric acid soln; After mixing, using diluted sodium hydroxide solution to regulate its pH again is 5.5～6.0, then adds Remazol Brilliant Violet carboxymethyl chitin hydrolase again; Under 50～60 ℃ temperature, reaction 1～2h, the Remazol Brilliant Violet carboxymethyl chitin hydrolase of adding: the mass ratio of chitosan raw material is 1: 50～100; Be warming up to 80～100 ℃ after reaction is accomplished, and keep pumping into whizzer after 10～20 minutes and carry out spinning, centrifuge speed is 6000 rev/mins～10000 rev/mins; Centrifugation time is 10～20 minutes, collects centrifugal clear liquid and deposition respectively, for centrifugal clear liquid; Use the nanofiltration device of molecular weight cut-off as 2000Da～4000Da; Under 0.8～1.8Mpa pressure, carry out nanofiltration separation, collect nanofiltration trapped fluid and filtered solution respectively, be the small molecules chitosan solution of preparing;
(2) preparation flavones-chitosan derivative solution
After (1) step accomplished, be that Hesperidin or ginkgolic flavone glycoside or buckwheat flavonoids are raw material with chromocor compound, according to the quality of chromocor compound: the volume ratio of water is the ratio of 1g: 30～60mL; Chromocor compound is added in the entry, and after mixing earlier, using diluted sodium hydroxide solution to regulate its pH again is 9～11; And stir process 30～50 minutes; Then according to chromocor compound solution: ethylene glycol diglycidylether: the mass ratio of the small molecules chitosan solution that (1) step prepared is 1: 1～3: 3～6 ratio, chromocor compound solution is joined (1) go on foot in the small molecules chitosan solution of preparing, and it is 10～11.5 that the back that stirs uses dilute sodium hydroxide to regulate pH; And when being warming up to 80～95 ℃; Add ethylene glycol diglycidylether again, the afterreaction 1～3h that stirs, using Hydrogen chloride to regulate pH at last is 4～6;
(3) preparation flavones-chitosan derivatives liquid concentrator
After the completion of (2) step; With flavones-chitosan derivative solution that (2) step prepared, be the ultra-filtration membrane of 10000Da～30000Da through molecular weight cut-off, be to carry out ultrafiltration under 0.08～0.2Mpa at pressure; Until the volume of ultrafiltration trapped fluid is that 10% of original volume～30% o'clock ends; Collect ultrafiltration filtered solution and trapped fluid respectively, for the ultrafiltration trapped fluid, according to the ultrafiltration trapped fluid: USP Kosher: hundred mould volume ratios of killing sanitas are 1: 0.10～0.20: 0.01～0.05 ratio; In the ultrafiltration trapped fluid; Add USP Kosher and the hundred mould sanitass that kill, mix, just prepare soluble solid concentration and be flavones-chitosan derivatives liquid concentrator of 35～40%.
2. according to the working method of the described a kind of water-soluble flavone-chitosan derivatives of claim 1, it is characterized in that:
In (1) step, the molecular-weight average of chitosan raw material is 45000Da, and concentration of hydrochloric acid is 0.2%, the quality of chitosan raw material: the hydrochloric acid soln volume ratio is 1g: 60mL; PH is 5.5,50 ℃ of temperature of reaction, and reaction times 1h, Remazol Brilliant Violet carboxymethyl chitin hydrolase: chitosan mass was than 1: 50; Be warming up to 80 ℃, 10 minutes hold-times, centrifuge speed is 6000 rev/mins; Centrifugation time is 10 minutes, and nanofiltration device molecular weight cut-off is 2000Da, and pressure is 0.8Mpa;
In (2) step, the raw material of chromocor compound is a Hesperidin, the quality of Hesperidin chromocor compound: the volume ratio of water is 1g: 30mL; PH is 9, and 30 minutes stir process time, Hesperidin chromocor compound solution: ethylene glycol diglycidylether: the mass ratio of the small molecules chitosan solution that (1) step prepared is 1: 1: 3; PH is 10; Be warming up to 80 ℃, reaction times 1h, reconciling pH is 4;
In (3) step; The molecular weight cut-off of ultra-filtration membrane is 10000Da; Ultrafiltration pressure is 0.08Mpa; Ultrafiltration to ultrafiltration trapped fluid volume be original volume 10% till, ultrafiltration trapped fluid: USP Kosher: hundred mould volume ratios of killing sanitas are 1: 0.10: 0.01, and the soluble solid concentration in flavones-chitosan derivatives liquid concentrator is 35%.
3. according to the working method of the described a kind of water-soluble flavone-chitosan derivatives of claim 1, it is characterized in that:
In (1) step, the molecular-weight average of chitosan raw material is 50000Da, and concentration of hydrochloric acid is 0.3%, the quality of chitosan raw material: the hydrochloric acid soln volume ratio is 1g: 100mL; PH is 5.8,55 ℃ of temperature of reaction, and reaction times 1.5h, Remazol Brilliant Violet carboxymethyl chitin hydrolase and chitosan mass were than 1: 80; Be warming up to 90 ℃, 15 minutes hold-times, centrifuge speed is 8000 rev/mins; Centrifugation time is 15 minutes, and nanofiltration device molecular weight cut-off is 3000Da, and pressure is 1.2Mpa;
In (2) step, the raw material of chromocor compound is a ginkgolic flavone glycoside, the quality of ginkgetin compound: the volume ratio of water is 1g: 50mL; PH is 10, and 40 minutes stir process time, ginkgetin compound solution: ethylene glycol diglycidylether: the mass ratio of the small molecules chitosan solution that (1) step prepared is 1: 2: 5; PH is 11; Be warming up to 90 ℃, reaction times 2h, reconciling pH is 5;
In (3) step; Ultrafiltration pressure is 0.14Mpa; The molecular weight cut-off of ultra-filtration membrane is 20000Da; Ultrafiltration to ultrafiltration trapped fluid volume be original volume 20% till, ultrafiltration trapped fluid: USP Kosher: hundred mould volume ratios of killing sanitas are 1: 0.15: 0.03, and the soluble solid concentration in flavones-chitosan derivatives liquid concentrator is 38%.
4. according to the working method of the described a kind of water-soluble flavone-chitosan derivatives of claim 1, it is characterized in that:
In (1) step, the molecular-weight average of chitosan raw material is 55000Da, and concentration of hydrochloric acid is 0.5%, the quality of chitosan raw material: the hydrochloric acid soln volume ratio is 1g: 120mL; PH is 6.0,60 ℃ of temperature of reaction, and reaction times 2h, Remazol Brilliant Violet carboxymethyl chitin hydrolase: chitosan mass was than 1: 100; Be warming up to 100 ℃, 20 minutes hold-times, centrifuge speed is 10000 rev/mins; Centrifugation time is 20 minutes, and nanofiltration device molecular weight cut-off is 4000Da, and pressure is 1.8Mpa;
In (2) step, the raw material of chromocor compound is a buckwheat flavonoids, the quality of buckwheat flavonoids compound: the volume ratio of water is 1g: 60mL; PH is 11, and 50 minutes stir process time, buckwheat flavonoids compound solution: ethylene glycol diglycidylether: the mass ratio of the small molecules chitosan solution that (1) step prepared is 1: 3: 6; PH is 11.5; Be warming up to 95 ℃, reaction times 3h, reconciling pH is 6;
In (3) step; Ultrafiltration pressure is 0.2Mpa; The molecular weight cut-off of ultra-filtration membrane is 30000Da; Ultrafiltration to ultrafiltration trapped fluid volume be original volume 30% till, ultrafiltration trapped fluid: USP Kosher: hundred mould volume ratios of killing sanitas are 1: 0.20: 0.05, and the soluble solid concentration in flavones-chitosan derivatives liquid concentrator is 40%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110045503A CN102174123B (en) | 2011-02-25 | 2011-02-25 | Production method of water soluble flavone-chitosan derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110045503A CN102174123B (en) | 2011-02-25 | 2011-02-25 | Production method of water soluble flavone-chitosan derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102174123A CN102174123A (en) | 2011-09-07 |
| CN102174123B true CN102174123B (en) | 2012-09-26 |
Family
ID=44517402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110045503A Expired - Fee Related CN102174123B (en) | 2011-02-25 | 2011-02-25 | Production method of water soluble flavone-chitosan derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102174123B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103989746B (en) * | 2014-05-12 | 2016-09-14 | 武汉理工大学 | A kind of broussoflavone nanometer formulation and preparation method thereof |
| CN107568737A (en) * | 2017-08-07 | 2018-01-12 | 天津科技大学 | Improve the water-soluble method with inoxidizability of aurantiamarin using chitosan oligosaccharide |
| CN109430878B (en) * | 2018-10-19 | 2022-04-05 | 天津科技大学 | Rutin chitosan oligosaccharide compound and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1748717A (en) * | 2005-07-18 | 2006-03-22 | 北京联合大学生物化学工程学院 | Method for prparing bee glue-ethyl cellulose microcapsule |
| US7125967B2 (en) * | 2003-10-08 | 2006-10-24 | Adjuvant Pharmaceuticals, Llc | Water-soluble chitosan having low endotoxin concentration and methods for making and using the same |
| CN101596223A (en) * | 2009-07-03 | 2009-12-09 | 重庆大学 | A kind of method of enriching ginkgetin compound |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4542014A (en) * | 1982-12-03 | 1985-09-17 | The Gillette Company | Hair treating composition |
| WO2007142704A2 (en) * | 2006-06-02 | 2007-12-13 | Hawaii Chitopure, Inc. | Chitosan-derivative compounds and methods of controlling microbial populations |
-
2011
- 2011-02-25 CN CN201110045503A patent/CN102174123B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7125967B2 (en) * | 2003-10-08 | 2006-10-24 | Adjuvant Pharmaceuticals, Llc | Water-soluble chitosan having low endotoxin concentration and methods for making and using the same |
| CN1748717A (en) * | 2005-07-18 | 2006-03-22 | 北京联合大学生物化学工程学院 | Method for prparing bee glue-ethyl cellulose microcapsule |
| CN101596223A (en) * | 2009-07-03 | 2009-12-09 | 重庆大学 | A kind of method of enriching ginkgetin compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102174123A (en) | 2011-09-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101605068B1 (en) | Method for extracting polysaccharides from higher plants and fungi through microwave chemical treatment | |
| CN102488713B (en) | Method for preparing sheep placenta extract and sheep placenta hydrolyzed collagen concentrated solution | |
| CN100540568C (en) | A kind of method of extracting algal polysaccharide sulfate | |
| CN102040675B (en) | Method for preparing hydroxypropyl-beta-cyclodextrin | |
| CN101724677B (en) | Method for extracting collagen polypeptide and hydroxyapatite in fish scales by cooking hot extrusion | |
| CN103360514B (en) | A kind of fast degradation prepares the method for water soluble oligo-chitosan | |
| CN104031158B (en) | A kind of technique extracting polysaccharide sulfate from Thallus Laminariae (Thallus Eckloniae) | |
| CN102174123B (en) | Production method of water soluble flavone-chitosan derivative | |
| CN106806160A (en) | Ultrasonic microwave aids in Enzymatic Extraction green tea polyphenols and its application in shower cream | |
| CN102038793A (en) | Preparation method of soapberry saponin | |
| CN103467617A (en) | Method for continuous counter-current ultrasonic extraction of high-purity astragalus polysaccharide | |
| CN104498564A (en) | Low molecular weight chondroitin sulfate preparation method | |
| CN102093748B (en) | Method for preparing radish red pigment homopolymer and radish proanthocyanidin from red-core radishes | |
| CN101560267A (en) | Preparation method of polysaccharide selenite | |
| CN102258580B (en) | Macleaya cordata total alkaloid preparation method | |
| CN106755214A (en) | A kind of method that two-phase enzyme hydrolysis obtains precious leaves of pulse plants glycosides I | |
| CN101759731B (en) | Extraction method of linseed gum and secoisolariciresin-ol diglucoside | |
| CN106434796B (en) | A method of preparing glycosylation aurantiamarin | |
| CN110551167A (en) | Method for preparing astragaloside | |
| CN104844707A (en) | Method for extracting phycocyanobilin from spirulina | |
| CN101367883A (en) | Method for extracting glossy ganoderma polysaccharide from fermentation liquor | |
| CN101302505B (en) | Method for separating and extracting alfapsin | |
| CN104788515A (en) | Method for preparing high-purity water-soluble oleuropein through reduced-pressure ultrasound-assisted extraction | |
| CN101121118B (en) | Modified macroporous polyvinyl alcohol resin and method for separating and purifying Chinese medicinal herb polysaccharide | |
| CN105399852A (en) | Technology for producing radix astragali polysaccharide by utilization of alkaline process extraction technology |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20120926 Termination date: 20150225 |
|
| EXPY | Termination of patent right or utility model |