CN106188574B - 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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Abstract
The present invention provides a kind of low concentration low degree of substitution carboxymethyl curdlan aqueous solution or hydrogels and its preparation method and application.Preparation method of the invention is simple, highly viscous aqueous solution or hydrogel can be formed under normal temperature condition, and the preparation of hydrogel is not necessarily to that any other organic solvent or chemical cross-linking agent is added, without adjusting pH value, without other metal ions of introducing.When it is applied as thickener under excellent low concentration thickening and gelatinization results especially suitable for dispersion system can provide desired rheological behavior, clarity and aesthetics.The thickener has highly-water-soluble, high thickening power and the thinning characteristic of high shear, ability with gelation under low concentration, being formed by solution and hydrogel has a high transparency, thus obtained hydrogel thickener, immune cosmetics and in terms of have broad application prospects.
Description
Technical field
The invention belongs to polymeric material field, in particular to a kind of low concentration low degree of substitution carboxymethyl curdlan is water-soluble
Liquid or physical hydrogel and its preparation method and application.
Background technique
Curdlan (Curdlan also known as Curdlan) is to be fermented to produce by Bacillus foecalis alkaligenes (Alcaliges faecalis)
A kind of raw all D- glucans as made of β -1,3 glucosides key connection.Natural curdlan molecular weight is tens of thousands of to up to a million
Between, solid is white powder, it is non-toxic and tasteless, it is not soluble in water, but dissolve 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.It China can in May, 2006 approval
It obtains right glue and is used as food additives (Zhang Hongbin, polysaccharide and its modified material, pp90-116, Chemical Industry Press, 2014).It
Right macromolecular polysaccharide has the good characteristics such as hydrophily, biocompatibility and biodegradable, is that more satisfactory can be formed
The macromolecule of hydrophilic colloid.The gel characteristic that curdlan has, water slurry can be formed according to the height of heating temperature
Low intensity heat reversible gel can also form high-strength hot irreversible gel (Zhang, H.B. et al., International
Journal Biological Macromolecules,2002,30:7-16)。
However curdlan is not soluble in water, cannot form aqueous solution, can be only formed unstable water slurry.This water is outstanding
Supernatant liquid does not have the thickening effect that polysaccharide solution usually has, and the curdlan hydrogel formed by heating water slurry
Also opaque.These problems greatly limit the extensive use of curdlan.Due in curdlan molecule there are great amount of hydroxy group,
Different groups can be introduced on repetitive unit by chemical modification, on the one hand can improve its dissolubility, while different substitutions
The introducing of base can also assign curdlan stronger bioactivity.If carboxymethylated curdlan is due to good anti-swollen
Tumor activity and stronger immune raising 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 immune cosmetics
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 two class of chemical gel and physical gel by the unusual of crosslinking method.United States Patent (USP)
US20130196944A1 describes application of the chemical crosslinking callose as novel tissue packing material, which use
The crosslinking agents such as 1,4- butanediol diglycidyl ether, dimethyl sulfoxide；United States Patent (USP) US005574023A describes 1,3- β-D-
The intramolecular crosslinking method of glucan, wherein also using including chemical cross-linking agents such as diamines, two hydrazides.These chemical gels are
It being formed by covalently cross-linked method, chemical cross-linking agent or organic solvent used in preparation process are difficult to completely remove,
If having residual in gel, it will cause potential cytotoxicities.So far some studies have shown that chemical crosslinking product peace
Quan Xing, side effect and application risk still have very big uncertainty (Reichenbach S. et al., Arthritis Care&
Research,2007,57(8):1410-1418)。
Physical hydrogel is by caused by the ionomer of such as electrostatic interaction, hydrogen bond action, crystallization or hydrophobic effect
The modes such as molecule cross-link formed, therefore the drawbacks of above-mentioned chemical gel can be overcome, avoid cytotoxic chemical crosslinking agent and have
The use of solvent.Curdlan is after carboxymethyl modified, although water solubility significantly improves, but if degree of substitution is excessively high, can lose
Lose it is original form gel in a heated condition characteristic (Jin Y. et al., Carbohydrate Research, 2006,341
(1):90-99).Patent CN200910054602.4, which is described, a kind of to be formed high substituted degree by freeze-thaw (degree of substitution is
0.50~1.0) preparation method of carboxymethyl curdlan physical hydrogel, has expanded its application range to a certain extent.But
Higher degree of substitution makes curdlan form hydrogel typically only by freeze-thaw method.
Through the retrieval discovery to existing technical literature and patent, there has been no to low degree of substitution carboxymethyl curdlan at present
The open report that thickening power and gelling properties are probed into.
Summary of the invention
In view of the above drawbacks of the prior art, the purpose of the present invention is to provide a kind of low concentration low degree of substitution carboxymethyls
Curdlan aqueous solution or physical hydrogel and its preparation method and application.Carboxy methylation of the curdlan Jing Guo lower degree
Afterwards, water solubility not only can be improved, but also its gel characteristic can be retained, can be only prepared by the method for controlled concentration and temperature can
Obtain right glue physical hydrogel.Preparation method of the invention is simple, hydrogel can be formed under normal temperature condition, and any without being added
Other chemical reagent, therefore obtained hydrogel has more extensively in terms of thickener, immune cosmetics and slow releasing carrier of medication
Wealthy application prospect.
The preparation method of low concentration low degree of substitution carboxymethyl curdlan physical hydrogel of the invention is replaced by adjusting
Degree and concentration prepare carboxymethyl curdlan aqueous solution, and to form gel by standing naturally.The viscosity of solution and gel it is strong
Degree can be adjusted by the concentration and degree of substitution for adjusting carboxymethyl curdlan.Compared with prior art, the present invention passes through
Control degree of substitution and concentration prepare carboxymethyl curdlan physical hydrogel, and method is more simple and convenient, and form gel process
In, the organic solvent or chemical cross-linking agent of any pair of organism toxic side effect are not introduced, without adjusting pH value, without introducing
Other metal ions.
Degree of substitution (DS) range for the low concentration low degree of substitution carboxymethyl curdlan that the present invention uses for 0.01~0.5,
Its molecular formula is：
Wherein, R CH2COONa or H, CH2The degree of substitution of COONa is 0.01~0.5, and the value range of polymerization degree n is 300
~6000.
The preparation method of low concentration low degree of substitution carboxymethyl curdlan physical hydrogel of the invention, including following step
Suddenly：
(1) low degree of substitution carboxymethyl curdlan is soluble in water, it stirs and makes it completely dissolved at room temperature~90 DEG C, match
At carboxymethyl curdlan aqueous solution, wherein the mass percent concentration of the 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 naturally quiet
It sets to form low concentration low degree of substitution carboxymethyl curdlan physical hydrogel.
The water is preferably ultrapure water or deionized water, and the room temperature refers to general room temperature, such as 5~40 DEG C,
Preferably 20~25 DEG C, without accurate control.
The content of carboxymethyl curdlan gum is low in the hydrogel that the present invention obtains, and mass percent is only 0.01%~2%, remaining
Amount is water.The characteristics of thickener, is thickening and gelatinization results under excellent low consistency conditions, especially suitable for aqueous point
Granular media system can provide desired rheological behavior, clarity and attractive in appearance.Therefore, using as thickener has height water-soluble
Property, high thickening power and the thinning characteristic of high shear, the ability with gelation under low concentration is formed by aqueous solution and hydrogel
With high transparency.The New stablization is in food, cosmetics, biological medicine material, detergent, detergent, oil recovery, coating etc.
Numerous areas has a wide range of applications.Since carboxymethyl curdlan also has certain immunocompetence and anti-tumor activity,
The thickener especially immune cosmetics, in terms of have potential using value, excellent bioactivity
More other hydrophilic colloids are with greater advantage.
Detailed description of the invention
Fig. 1 is various concentration carboxymethyl curdlan water under the conditions of identical degree of substitution in a preferred embodiment of the present invention
The dependence graph of elastic modulus G ' and viscous modulus G " and frequencies omega of the gel at 25 DEG C；
Fig. 2 is various concentration carboxymethyl curdlan water under the conditions of identical degree of substitution in a preferred embodiment of the present invention
The dependence graph of gel the complex viscosity η * at 25 DEG C and frequencies omega；
Fig. 3 is various concentration different degree of substitution carboxymethyl curdlan aqueous solution or water-setting in a comparative example of the invention
The dependence graph of glue the complex viscosity η * at 25 DEG C and frequencies omega.
Specific embodiment
Specific embodiments of the present invention are given below to elaborate.The present embodiment is based on the technical solution of the present invention
Under implemented, the detailed implementation method and specific operation process are given, but protection scope of the present invention be not limited to it is 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 for accurately weighing DS=0.1, n=3000 is dissolved in ultrapure water, prepares quality
The carboxymethyl curdlan aqueous solution that concentration is 1%；
(2) by the carboxymethyl curdlan aqueous temperature control prepared in step (1) in room temperature, by standing shape naturally
At carboxymethyl curdlan hydrogel.
Utilize the springform for the carboxymethyl curdlan hydrogel that TA AR G2 type rotational rheometer testing example 1 obtains
G ', viscous modulus G " and complex viscosity η * are measured with the variation of frequencies omega, is as a result shown in Fig. 1 and Fig. 2.From figure 1 it will be seen that
The system G ' of embodiment 1>G " and hardly follow frequency variation；It can be observed from fig. 2 that its complex viscosity with frequency linearity it is quick under
Drop, 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
The mass concentration of the carboxymethyl curdlan aqueous solution configured in step (1) is 0.5%.
From figure 1 it will be seen that the system G ' of embodiment 2>G " and with frequency increase slightly 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
The mass concentration of the carboxymethyl curdlan aqueous solution configured in step (1) is 0.4%.
From figure 1 it will be seen that G ' when the system low frequency of embodiment 3<G " and G ' when high frequency>G " and display frequency dependence
Property；It can be observed from fig. 2 that its complex viscosity declines with frequency linearity, high thickening power and shear shinning characteristic are shown.
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
The mass concentration of the carboxymethyl curdlan aqueous solution configured in step (1) is 0.3%.
From figure 1 it will be seen that the system G ' of embodiment 4 is respectively less than G " and has higher within the scope of entire test frequency
Frequency dependence；It can be observed from fig. 2 that its complex viscosity declines with frequency linearity, high thickening power and shear shinning are shown
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 degree of substitution DS=0.02 of the carboxymethyl curdlan used in step (1).The intensity of 5 gained gel of embodiment, which is greater than, to be implemented
The intensity of 1 gained gel of example.
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 degree of substitution DS=0.45 of the carboxymethyl curdlan used in step (1).The intensity of 6 gained gel of embodiment, which is less than, to be implemented
The intensity of 1 gained gel of example.
Comparative example 1：
(1) accurately weigh respectively the non-carboxymethyl-modification of DS=0, n=3000 curdlan 0.001g, 0.01g,
0.10g and 0.20g are dissolved in ultrapure water, prepare the non-carboxy methylation that mass concentration is respectively 0.01%, 0.1%, 1% and 2%
Modified curdlan aqueous suspension；
(2) by the curdlan water slurry temperature control for the non-carboxymethyl-modification prepared in step (1) in room temperature, certainly
Aqueous solution can neither be formed after so standing, hydrogel can not be formed.
Comparative example 2：
(1) accurately weigh n=3000 and degree of substitution be respectively DS=0.6,0.7,0.8,0.9 carboxymethyl curdlan it is each
0.20g is dissolved in ultrapure water respectively, is configured to the carboxymethyl curdlan aqueous solution that mass concentration is 2% respectively；
(2) the high substituted carboxymethyl curdlan aqueous temperature control prepared in step (1) is stood naturally in room temperature
It is still afterwards aqueous solution, hydrogel cannot be formed.
Comparative example 3：
(1) accurately weigh n=3000 and degree of substitution be respectively DS=0.1,0.8 carboxymethyl curdlan 0.05g,
0.10g is dissolved in ultrapure water, is configured to the carboxymethyl curdlan aqueous solution that mass concentration is 0.5%, 1% respectively；
(2) by the carboxymethyl curdlan aqueous temperature control prepared in step (1) in room temperature, by standing shape naturally
At carboxymethyl curdlan aqueous solution or hydrogel.
The carboxymethyl curdlan aqueous solution or hydrogel obtained using TA AR G2 type rotational rheometer test comparison example 3
Complex viscosity η * with the variation of frequencies omega, be as a result shown in Fig. 3.As seen from Figure 3, under same concentrations, low degree of substitution carboxylic
The complex viscosity η * of methyl curdlan (DS=0.1) is much larger than answering for high-substitution carboxymethyl curdlan (DS=0.8)
Number viscosities il *.By taking frequencies omega=1rad/s as an example, 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 be 1% when, the η * value of low degree of substitution carboxymethyl curdlan is about
It is 500 times of high-substitution carboxymethyl curdlan η * value, it is seen that low degree of substitution carboxymethyl curdlan shows extremely aobvious
The thickening power of work.
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that the ordinary skill of this field is without wound
The property made labour, which according to the present invention can conceive, makes many modifications and variations.Therefore, all technician in the art
Pass through logic analysis, reasoning or the limited available technology of test on the basis of existing technology under this invention's idea
Scheme, all should be within the scope of protection determined by the claims.
Claims (5)
1. a kind of preparation method of carboxymethyl curdlan hydrogel, which is characterized in that the molecule of the carboxymethyl curdlan
Formula is：
Wherein, R CH2COONa or H, CH2The degree of substitution of COONa is that 0.01~0.45, n is 300~6000, the hydrogel
Preparation method includes the following steps：
(1) the carboxymethyl curdlan is soluble in water, it stirs and makes it completely dissolved at room temperature~90 DEG C, formed water-soluble
Liquid；
(2) aqueous solution control obtained in step (1) is formed into the hydrogel by standing naturally in room temperature；
The mass percent concentration of carboxymethyl curdlan described in the aqueous solution be 0.01%~2%, the room temperature be 5~
40℃。
2. the preparation method of carboxymethyl curdlan hydrogel as described in claim 1, which is characterized in that the water is ultrapure
Water or deionized water.
3. a kind of application of carboxymethyl curdlan as thickener in dispersion system, which is characterized in that the carboxylic first
The molecular formula of base curdlan is：
Wherein, R CH2COONa or H, CH2The degree of substitution of COONa is that 0.01~0.45, n is 300~6000, and the carboxymethyl can
Obtaining mass percent concentration of the right glue in the dispersion system is 0.01%~2%.
4. application of the carboxymethyl curdlan as claimed in claim 3 as thickener in dispersion system, feature
It is, the thickener addition is in food, cosmetics, biological medicine material, detergent, detergent, oil recovery, coating.
5. application of the carboxymethyl curdlan as claimed in claim 4 as thickener in dispersion system, feature
It is, the biological medicine material is slow releasing carrier of medication.
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| PCT/CN2016/093011 WO2018014373A1 (en) | 2016-07-18 | 2016-08-03 | Aqueous solution or hydrogel of carboxymethyl-curdlan |
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| 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 |
| 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 |
| CN112048028B (en) * | 2020-09-24 | 2021-11-12 | 江南大学 | Light-stable modified curdlan antioxidant and preparation method and application thereof |
| CN113845668B (en) * | 2021-08-06 | 2023-08-08 | 广东省科学院健康医学研究所 | Polysaccharide composite hydrogel and preparation method and application thereof |
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| CN101602814A (en) * | 2009-07-09 | 2009-12-16 | 上海交通大学 | Carboxymethyl curdlan gum physical hydrogel and preparation method thereof |
| CN102198511A (en) * | 2011-04-28 | 2011-09-28 | 上海交通大学 | Preparation method of carboxymethyl curdlan polysaccharide-based colloidal aqueous solution containing nano silver particles |
| WO2012162840A1 (en) * | 2011-06-03 | 2012-12-06 | Frank Gu | Polysaccharide-based hydrogel polymer and uses thereof |
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| CN102702537A (en) * | 2012-05-16 | 2012-10-03 | 吉武科 | Method capable of improving gel strength of curdlan |
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| CN101602814A (en) * | 2009-07-09 | 2009-12-16 | 上海交通大学 | Carboxymethyl curdlan gum physical hydrogel and preparation method thereof |
| CN102198511A (en) * | 2011-04-28 | 2011-09-28 | 上海交通大学 | Preparation method of carboxymethyl curdlan polysaccharide-based colloidal aqueous solution containing nano silver particles |
| WO2012162840A1 (en) * | 2011-06-03 | 2012-12-06 | Frank Gu | Polysaccharide-based hydrogel polymer and uses thereof |
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