CN106188574A - A kind of carboxymethyl curdlan aqueous solution or hydrogel and its preparation method and application - Google Patents
A kind of carboxymethyl curdlan aqueous solution or hydrogel and its preparation method and application Download PDFInfo
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- CN106188574A CN106188574A CN201610566340.XA CN201610566340A CN106188574A CN 106188574 A CN106188574 A CN 106188574A CN 201610566340 A CN201610566340 A CN 201610566340A CN 106188574 A CN106188574 A CN 106188574A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/07—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media from polymer solutions
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/02—Dextran; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/02—Dextran; Derivatives thereof
Abstract
The invention provides a kind of low concentration low degree of substitution carboxymethyl curdlan aqueous solution or hydrogel and its preparation method and application.The preparation method of the present invention is simple, can form full-bodied aqueous solution or hydrogel, and the preparation of hydrogel is without adding other organic solvent any or chemical cross-linking agent under normal temperature condition, it is not necessary to regulate pH value, without introducing other metal ions.It has the thickening under the low concentration of excellence and gelatinization results as thickening agent when applying, be particularly well-suited to dispersion system, be provided that desired rheological behavior, clarity and aesthetic property.This thickening agent has highly-water-soluble, high thickening power and the thinning characteristic of high shear, there is the ability of gelation under low concentration, the solution and the hydrogel that are formed have high transparent, and therefore obtained hydrogel has broad application prospects at aspects such as thickening agent, immunization cosmetic and slow releasing carrier of medication.
Description
Technical field
The invention belongs to polymeric material field, water-soluble particularly to a kind of low concentration low degree of substitution carboxymethyl curdlan
Liquid or physical hydrogel and its preparation method and application.
Background technology
Curdlan (Curdlan has another name called Curdlan) is to be produced by Bacillus foecalis alkaligenes (Alcaliges faecalis) fermentation
Raw a kind of D-glucosan being all formed by connecting by β-1,3 glycosidic bond.Natural curdlan molecular weight is tens thousand of to up to a million
Between, solid is white powder, nonpoisonous and tasteless, water insoluble, but dissolves in aqueous slkali and DMSO solvent.Curdlan is in 1996
Nian Huo food and drug administration (FDA) certification, can be used as additive in food.In May, 2006, approval can in China
Right glue is used as food additive (Zhang Hongbin, polysaccharide and material modified, pp90-116, Chemical Industry Press, 2014).My god
So macromolecular polysaccharide has the good characteristics such as hydrophilic, biocompatibility and biodegradable, is more satisfactory being formed
The macromolecule of hydrophilic colloid.The gel characteristic that curdlan has, its water slurry, according to the height of heating-up temperature, can be formed
Low intensity heat reversible gel, also can form high-strength hot irreversible gel (Zhang, H.B. et al., International
Journal Biological Macromolecules,2002,30:7-16)。
But curdlan is water insoluble, it is impossible to form aqueous solution, can be only formed the water slurry of instability.This water hangs
Supernatant liquid does not have the thickening effect that polysaccharide solution is generally of, and the curdlan hydrogel formed by heating water slurry
The opaquest.These problems greatly limit the extensive application of curdlan.Owing to there is great amount of hydroxy group in curdlan molecule,
Different groups can be introduced on repetitive by chemical modification, on the one hand can improve its dissolubility, the most different replacements
The introducing of base also can give the biological activity that curdlan is higher.As carboxymethylated curdlan swells owing to having good resisting
Tumor activity and stronger immunity improve activity more already paid close attention to (Sasaki T. et al., Cancer Research, 1978,
38(2):379-383；Sasaki T. et al., European Journal of Cancer, 1979,15 (2): 211-215；
Saito, H. et al., Carbohydrate Research, 1991,217:181-190), it is used as exempting from immunization cosmetic
Epidemic disease additive and slow releasing carrier of medication (Na K. et al., Journal of Controlled Release, 2000,69 (2):
225-236；Rafigh S.M. et al., International Journal of Biological Macromolecules,
2016,87:603-610；Li L. et al., Nanotechnology, 2010,21 (26): 265601).
Polysaccharide hydrogel is divided into chemical gel and physical gel two class by the unusual of crosslinking method.United States Patent (USP)
US20130196944A1 describe chemical crosslinking callose as the application of novel tissue packing material, which use
The cross-linking agent such as 1,4-butanediol diglycidyl ether, dimethyl sulfoxide；United States Patent (USP) US005574023A describes 1,3-β-D-
The intramolecular crosslinking method of glucosan, wherein also using and includes the chemical cross-linking agent such as diamidogen, two hydrazides.These chemical gels are
Being formed by covalently cross-linked method, the chemical cross-linking agent or the organic solvent that use in preparation process are difficult to remove completely,
If there being residual in gel, potential cytotoxicity can be caused.Some researchs so far show, the peace of chemical crosslinking product
Quan Xing, side effect and application risk still have the biggest uncertainty (Reichenbach S. et al., Arthritis Care&
Research,2007,57(8):1410-1418)。
Physical hydrogel is that the ionomer by such as electrostatic interaction, hydrogen bond action, crystallization or hydrophobic interaction are caused
The mode such as molecule crosslinking formed, therefore can overcome the drawback of above-mentioned chemical gel, it is to avoid cytotoxic chemical cross-linking agent and having
The use of machine solvent.Curdlan is after carboxymethyl modified, although water solublity significantly improves, but then can lose if instead of spending height
Lose original form gel in a heated condition characteristic (Jin Y. et al., Carbohydrate Research, 2006,341
(1):90-99).Patent CN200910054602.4 describes and a kind of form high substituted degree by freeze-thaw (substitution value is
0.50～1.0) preparation method of carboxymethyl curdlan physical hydrogel, has expanded its range of application to a certain extent.But
Higher substitution value makes curdlan be typically only possible by freeze-thaw method and forms hydrogel.
Through the retrieval of prior art literature and patent is found the most not yet have low degree of substitution carboxymethyl curdlan
Thickening power and gelling properties carry out the open report probed into.
Summary of the invention
Because the drawbacks described above of prior art, it is an object of the invention to provide a kind of low concentration low degree of substitution carboxymethyl
Curdlan aqueous solution or physical hydrogel and its preparation method and application.Curdlan is through the carboxy methylation of lower degree
After, both can improve water solublity, its gel characteristic can have been retained again, only can be prepared by the method for controlled concentration and temperature can
Obtain right glue physical hydrogel.The preparation method of the present invention is simple, can form hydrogel under normal temperature condition, and any without adding
Other chemical reagent, therefore obtained hydrogel has more extensively in terms of thickening agent, immunization cosmetic and slow releasing carrier of medication
Wealthy application prospect.
The preparation method of the low concentration low degree of substitution carboxymethyl curdlan physical hydrogel of the present invention is replaced by regulation
Degree and concentration prepare carboxymethyl curdlan aqueous solution, and form gel by nature standing.The viscosity of solution and gel strong
Degree can be adjusted by the concentration of regulation carboxymethyl curdlan and substitution value.Compared with prior art, the present invention passes through
Controlling substitution value and concentration prepares carboxymethyl curdlan physical hydrogel, method is the most simple and convenient, and forms gel process
In, do not introduce any organic solvent to organism toxic side effect or chemical cross-linking agent, it is not necessary to regulate pH value, without introducing
Other metal ions.
Substitution value (DS) scope of the low concentration low degree of substitution carboxymethyl curdlan that the present invention uses is 0.01～0.5,
Its molecular formula is:
Wherein, R is CH2COONa or H, CH2The substitution value of COONa is 0.01～0.5, and the span of polymerization degree n is 300
～6000.
The preparation method of the low concentration low degree of substitution carboxymethyl curdlan physical hydrogel of the present invention, including following step
Rapid:
(1) by soluble in water for low degree of substitution carboxymethyl curdlan, at room temperature～90 DEG C, stirring makes it be completely dissolved, and joins
Becoming carboxymethyl curdlan aqueous solution, the mass percent concentration of wherein said carboxymethyl curdlan is 0.01%～2%；
(2) the low degree of substitution carboxymethyl curdlan aqueous solution obtained in step (1) is controlled in room temperature, by the most quiet
Put formation low concentration low degree of substitution carboxymethyl curdlan physical hydrogel.
Described water is preferably ultra-pure water or deionized water, and described room temperature refers to general indoor temperature, such as 5～40 DEG C,
It is preferably 20～25 DEG C, it is not necessary to accurately control.
In the hydrogel that the present invention obtains, the content of carboxymethyl curdlan gum is low, and mass percent is only 0.01%～2%, remaining
Amount is water.The feature of this thickening agent is the thickening under the low consistency conditions of excellence and gelatinization results, is particularly well-suited to aqueous and divides
Prose style free from parallelism system, is provided that desired rheological behavior, clarity and character attractive in appearance.Have high water-soluble accordingly, as thickening agent use
Property, high thickening power and the thinning characteristic of high shear, have the ability of gelation under low concentration, the aqueous solution formed and hydrogel
There is high transparent.This New stablization is at food, cosmetics, biological medicine material, detergent, cleaning agent, oil recovery, coating etc.
Numerous areas has a wide range of applications.Owing to carboxymethyl curdlan also has certain immunocompetence and anti-tumor activity,
This thickening agent has potential using value at aspects such as immunization cosmetic, slow releasing carrier of medication especially, its excellent biological activity
Compared with other hydrophilic colloid, there is bigger advantage.
Accompanying drawing explanation
Fig. 1 is in a preferred embodiment of the present invention, variable concentrations carboxymethyl curdlan water under the conditions of identical substitution value
Gel elastic modulus G ' at 25 DEG C and viscous modulus G " with the dependence graph of frequencies omega；
Fig. 2 is in a preferred embodiment of the present invention, variable concentrations carboxymethyl curdlan water under the conditions of identical substitution value
Gel complex viscosity η * at 25 DEG C and the dependence graph of frequencies omega；
Fig. 3 is in one comparative example of the present invention, variable concentrations different degree of substitution carboxymethyl curdlan aqueous solution or water-setting
Glue complex viscosity η * at 25 DEG C and the dependence graph of frequencies omega.
Detailed description of the invention
The specific embodiment that the present invention is given below elaborates.The present embodiment is premised on technical solution of the present invention
Under implement, give detailed embodiment and concrete operating process, but protection scope of the present invention be not limited to following
Embodiment.
Embodiment 1:
The preparation method of the carboxymethyl curdlan physical hydrogel of embodiment 1 is as follows:
(1) the carboxymethyl curdlan 0.10g accurately weighing DS=0.1, n=3000 is dissolved in ultra-pure water, prepares quality
Concentration is the carboxymethyl curdlan aqueous solution of 1%；
(2) the carboxymethyl curdlan aqueous temperature of preparation in step (1) is controlled in room temperature, by naturally standing shape
Become carboxymethyl curdlan hydrogel.
Utilize the springform of the carboxymethyl curdlan hydrogel that TA AR G2 type rotational rheometer testing example 1 obtains
Amount G ', viscous modulus G " and complex viscosity η * with the change of frequencies omega, result is shown in Fig. 1 and Fig. 2.From figure 1 it will be seen that
System G of embodiment 1 ' > G " and change little with frequency；It can be observed from fig. 2 that its complex viscosity with frequency linearity quickly under
Fall, shows high thickening power and the thinning characteristic of high shear.
Embodiment 2:
The preparation method of the carboxymethyl curdlan physical hydrogel of embodiment 2 is substantially the same manner as Example 1, and difference only exists
In step (1), the mass concentration of the carboxymethyl curdlan aqueous solution of configuration is 0.5%.
From figure 1 it will be seen that system G of embodiment 2 ' > G " and slightly increase with frequency increase；It can be observed from fig. 2 that its
Complex viscosity declines with frequency linearity, shows high thickening power and the thinning characteristic of high shear.
Embodiment 3:
The preparation method of the carboxymethyl curdlan physical hydrogel of embodiment 3 is substantially the same manner as Example 1, and difference only exists
In step (1), the mass concentration of the carboxymethyl curdlan aqueous solution of configuration is 0.4%.
From figure 1 it will be seen that G '<G during the system low frequency of embodiment 3 " and G '>G during high frequency " and all display frequencies rely on
Property；It can be observed from fig. 2 that its complex viscosity declines with frequency linearity, show high thickening power and shear shinning characteristic.
Embodiment 4:
The preparation method of the carboxymethyl curdlan physical hydrogel of embodiment 4 is substantially the same manner as Example 1, and difference only exists
In step (1), the mass concentration of the carboxymethyl curdlan aqueous solution of configuration is 0.3%.
From figure 1 it will be seen that in whole test frequency range, system G of embodiment 4 ' it is respectively less than G " and have higher
Frequency dependence；It can be observed from fig. 2 that its complex viscosity declines with frequency linearity, show high thickening power and shear shinning
Characteristic.
Embodiment 5:
The preparation method of the carboxymethyl curdlan physical hydrogel of embodiment 5 is substantially the same manner as Example 1, and difference only exists
The substitution value DS=0.02 of the carboxymethyl curdlan used in step (1).The intensity of embodiment 5 gained gel is more than implementing
The intensity of example 1 gained gel.
Embodiment 6:
The preparation method of the carboxymethyl curdlan physical hydrogel of embodiment 6 is substantially the same manner as Example 1, and difference only exists
The substitution value DS=0.45 of the carboxymethyl curdlan used in step (1).The intensity of embodiment 6 gained gel is less than implementing
The intensity of example 1 gained gel.
Comparative example 1:
(1) the most accurately weigh the curdlan 0.001g of the non-carboxymethyl-modification of DS=0, n=3000,0.01g,
0.10g and 0.20g is dissolved in ultra-pure water, and preparation mass concentration is respectively the non-carboxy methylation of 0.01%, 0.1%, 1% and 2%
Modified curdlan aqueous suspension；
(2) the curdlan water slurry temperature of the non-carboxymethyl-modification of preparation in step (1) is controlled in room temperature, from
Aqueous solution can not be formed after so standing, hydrogel can not be formed.
Comparative example 2:
(1) n=3000 is accurately weighed and carboxymethyl curdlan that substitution value is respectively DS=0.6,0.7,0.8,0.9 is each
0.20g is dissolved in ultra-pure water respectively, is configured to the carboxymethyl curdlan aqueous solution that mass concentration is 2% respectively；
(2) the high substituted carboxymethyl curdlan aqueous temperature of preparation in step (1) is controlled in room temperature, naturally stand
After be still aqueous solution, it is impossible to formed hydrogel.
Comparative example 3:
(1) accurately weigh n=3000 and substitution value be respectively DS=0.1, the carboxymethyl curdlan 0.05g of 0.8,
0.10g is dissolved in ultra-pure water, is configured to the carboxymethyl curdlan aqueous solution that mass concentration is 0.5%, 1% respectively；
(2) the carboxymethyl curdlan aqueous temperature of preparation in step (1) is controlled in room temperature, by naturally standing shape
Become carboxymethyl curdlan aqueous solution or hydrogel.
Utilize carboxymethyl curdlan aqueous solution or hydrogel that TA AR G2 type rotational rheometer test comparison example 3 obtains
Complex viscosity η * with the change of frequencies omega, result is shown in Fig. 3.As seen from Figure 3, under same concentrations, low degree of substitution carboxylic
Complex viscosity η * all answering much larger than high-substitution carboxymethyl curdlan (DS=0.8) of methyl curdlan (DS=0.1)
Number viscosities il *.As a example by frequencies omega=1rad/s, when concentration is 0.5%, the η * value of low degree of substitution carboxymethyl curdlan is about
70 times of high-substitution carboxymethyl curdlan η * value；And concentration is when being 1%, the η * value of low degree of substitution carboxymethyl curdlan is about
For high-substitution carboxymethyl curdlan η * value 500 times, it is seen that low degree of substitution carboxymethyl curdlan shows the most aobvious
The thickening power write.
The preferred embodiment of the present invention described in detail above.Should be appreciated that the ordinary skill of this area is without wound
The property made work just can make many modifications and variations according to the design of the present invention.Therefore, all technical staff in the art
The most on the basis of existing technology by logical analysis, reasoning or the available technology of limited test
Scheme, all should be in the protection domain being defined in the patent claims.
Claims (10)
1. a carboxymethyl curdlan aqueous solution or hydrogel, it is characterised in that the molecular formula of described carboxymethyl curdlan
For:
Wherein, R is CH2COONa or H, CH2The substitution value of COONa is 0.01～0.5, and n is 300～6000, and described aqueous solution can
Form described hydrogel.
2. carboxymethyl curdlan aqueous solution as claimed in claim 1 or hydrogel, it is characterised in that institute in described aqueous solution
The mass percent concentration stating carboxymethyl curdlan is 0.01%～2%.
3. carboxymethyl curdlan aqueous solution as claimed in claim 2 or hydrogel, it is characterised in that the system of described aqueous solution
Preparation Method comprises the following steps:
(1) by soluble in water for described carboxymethyl curdlan, at room temperature～90 DEG C, stirring makes it be completely dissolved, and forms described water
Solution.
4. carboxymethyl curdlan aqueous solution as claimed in claim 2 or hydrogel, it is characterised in that the system of described hydrogel
Preparation Method comprises the following steps:
(1) by soluble in water for described carboxymethyl curdlan, at room temperature～90 DEG C, stirring makes it be completely dissolved, and forms described water
Solution；
(2) the described aqueous solution obtained in step (1) is controlled in room temperature, form described hydrogel by naturally standing.
5. the carboxymethyl curdlan aqueous solution as described in claim 3 or 4 or hydrogel, it is characterised in that described water is super
Pure water or deionized water.
6. the carboxymethyl curdlan aqueous solution as described in claim 3 or 4 or hydrogel, it is characterised in that described room temperature is 5
～40 DEG C.
7. the carboxymethyl curdlan aqueous solution as according to any one of claim 1-4 or hydrogel answering as thickening agent
With.
8. carboxymethyl curdlan aqueous solution as claimed in claim 7 or hydrogel are as the application of thickening agent, and its feature exists
In, described thickening agent is added in food, cosmetics, biological medicine material, detergent, cleaning agent, oil recovery, coating.
9. carboxymethyl curdlan aqueous solution as claimed in claim 8 or hydrogel are as the application of thickening agent, and its feature exists
In, described cosmetics are immunization cosmetic.
10. carboxymethyl curdlan aqueous solution as claimed in claim 8 or hydrogel are as the application of thickening agent, and its feature exists
In, described biological medicine material is slow releasing carrier of medication.
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| CN201610566340.XA CN106188574B (en) | 2016-07-18 | 2016-07-18 | A kind of carboxymethyl curdlan aqueous solution or hydrogel and its preparation method and application |
| PCT/CN2016/093011 WO2018014373A1 (en) | 2016-07-18 | 2016-08-03 | Aqueous solution or hydrogel of carboxymethyl-curdlan |
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| CN201610566340.XA CN106188574B (en) | 2016-07-18 | 2016-07-18 | A kind of carboxymethyl curdlan aqueous solution or hydrogel and its preparation method and application |
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| CN107495334A (en) * | 2017-07-17 | 2017-12-22 | 上海交通大学 | A kind of thickening nutritional preparation for dysphagia patients and preparation method thereof |
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| CN107495334A (en) * | 2017-07-17 | 2017-12-22 | 上海交通大学 | A kind of thickening nutritional preparation for dysphagia patients and preparation method thereof |
| WO2019015165A1 (en) * | 2017-07-17 | 2019-01-24 | 上海交通大学 | Thickening nutritional preparation for patients with dysphagia and preparation method therefor |
| CN107495334B (en) * | 2017-07-17 | 2021-03-30 | 上海交通大学 | Thickened nutritional preparation for dysphagia patients and preparation method thereof |
| CN110041537A (en) * | 2019-04-24 | 2019-07-23 | 上海交通大学 | A kind of ionomer carboxymethyl curdlan gum physical hydrogel and preparation method thereof |
| CN110305232A (en) * | 2019-06-26 | 2019-10-08 | 内蒙古大学 | Water-absorbing material based on modified gel polysaccharide and preparation method thereof |
| CN110305232B (en) * | 2019-06-26 | 2022-05-13 | 内蒙古大学 | Water-absorbing material based on modified gel polysaccharide and preparation method thereof |
| CN110511401A (en) * | 2019-08-23 | 2019-11-29 | 广州暨南生物医药研究开发基地有限公司 | A kind of preparation method and application of high tenacity curdlan hydrogel |
| CN112048028A (en) * | 2020-09-24 | 2020-12-08 | 江南大学 | Light-stable modified curdlan antioxidant and preparation method and application thereof |
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| Publication number | Publication date |
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| CN106188574B (en) | 2018-11-20 |
| WO2018014373A1 (en) | 2018-01-25 |
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