CN108409874A - A kind of preparation method of high substituted degree etherificate cornstarch - Google Patents
A kind of preparation method of high substituted degree etherificate cornstarch Download PDFInfo
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- CN108409874A CN108409874A CN201810331795.2A CN201810331795A CN108409874A CN 108409874 A CN108409874 A CN 108409874A CN 201810331795 A CN201810331795 A CN 201810331795A CN 108409874 A CN108409874 A CN 108409874A
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- cornstarch
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/08—Ethers
- C08B31/12—Ethers having alkyl or cycloalkyl radicals substituted by heteroatoms, e.g. hydroxyalkyl or carboxyalkyl starch
Abstract
The present invention provides a kind of preparation method of high substituted degree etherificate cornstarch, using cornstarch as raw material existing for nano micro crystal cellulose under the conditions of, high substituted degree etherification starch is prepared using solvent method；The high substituted degree refers to that degree of substitution is more than 0.2；The nano micro crystal cellulose is the nano micro crystal cellulose NCC of 100 500nm of fibre length.Using nano-cellulose as catalyst preparation etherification starch, it is easy to operate, with obvious effects, pollution it is small.Step is simple and convenient to operate, is highly practical.
Description
Technical field
The invention belongs to high substituted degree starch preparation field, more particularly to a kind of preparation of high substituted degree etherificate cornstarch
Method.
Background technology
Starch is the carbohydrate that plant is formed through photosynthesis, as a kind of important stored energy form of plant,
Yield is only second to cellulose, is a kind of pure natural and renewable resource of abundance.Starch is cheap, degradable, environment is friendly
The features such as good, makes it be widely used in each industrial circle.It is low with gelatinization point that etherification starch compares ative starch, hydrophily is strong,
How the advantages that good film-forming property, superior water retention property is reducing the use of chemicals, while improving etherificate degree of substitution, promotes
Its application performance and market value are a problems for needing to solve at present.
Cellulose is a kind of natural green high molecular material, is renewable resource.Nano-cellulose can be from multiple fiber
It is usually separated in source, including plant, animal, bacterium and algae etc., nano micro crystal cellulose refers to having certain space size
For the cellulose of Nano grade.The high intensity of nano-cellulose, lightweight, it is renewable, biodegradable the advantages that also changing it
The application study of work Material Field is more and more.
In recent years, with the gradual protrusion of environmental problem, for Green Chemistry modification technology and degradable product
Demand is higher and higher.Therefore, how more will replace traditional chemical medicament by environmentally friendly products, and be introduced into modernization industrial and commercial bank
It is the important directions of current chemical industry development in industry.
Bai Zhonglan etc. about《Potato starchy residue prepares the research of carboxymethyl cellulose and carboxymethyl starch mixture》With
Potato starchy residue is that raw material prepares carboxymethyl cellulose (CMC) and carboxymethyl starch (CMS) mixture.But it is utilized due to it
Waste and the conventional fibre element generated in potato starch production process, therefore, the etherificate of low degree of substitution is formed sediment in can only preparing
Powder.
Invention content
In order to overcome above-mentioned deficiency, the present invention to provide a kind of preparation method of high substituted degree etherificate cornstarch.With nanometer
Cellulose is catalyst modification starch, reduces the consumption of chemicals, and is influenced on starch small；Preparation method cost
It is low, it is degradable pollution-free.
To achieve the goals above, the present invention adopts the following technical scheme that：
A kind of preparation method of high substituted degree etherificate cornstarch, is deposited using cornstarch as raw material in nano micro crystal cellulose
Under the conditions, high substituted degree etherification starch is prepared using solvent method；
The high substituted degree refers to that degree of substitution is more than 0.2；
The nano micro crystal cellulose is the nano micro crystal cellulose NCC of fibre length 100-500nm.
Preferably, the mass ratio of the cornstarch and nano micro crystal cellulose is 100：0.5~5.
Preferably, the solvent method the specific steps are：In certain density sodium hydroxide-ethanol solution, by corn
Starch and nano micro crystal cellulose alkalize；It adds etherifying agent to be etherified, after the completion of etherification reaction, washing centrifugation is adjusted
It is neutrality to save pH value, it is dry to get.
Preferably, the cornstarch, ethyl alcohol mass volume ratio be 10-12g:25-30ml.
Preferably, the cornstarch, sodium hydroxide mass ratio be 100：16-20.
Preferably, the etherifying agent is chloroacetic acid and sodium chloroacetate.
Preferably, the cornstarch, etherifying agent mass ratio be 100：5-20, i.e.,：The amount ranges of etherifying agent are in 5-
20% relative to starch absolute dry mass.
The study found that when alkalization time is less than 0.5h, starch etherificate is ineffective, after alkalization time is more than 3h, after
The continuous alkalization time that increases influences less the degree of etherification falling of starch, and therefore, the condition of preferred quaternization is 40-50 in the application
DEG C reaction 0.5-3h.
Preferably, the time of the etherification reaction is 40-50 DEG C of reaction 3-10h.
The high substituted degree prepared the present invention also provides any above-mentioned method is etherified cornstarch.
Beneficial effects of the present invention
(1) starch conversion of the invention reduces the consumption of chemicals, and to starch using nano-cellulose as catalyst
Whiteness influences small；
(2) etherification starch of the present invention is at low cost using cornstarch, nano-cellulose NCC as primary raw material, degradable no dirt
Dye；
(3) preparation method of the present invention is simple, degree of substitution is high, highly practical, easy to spread.
Specific implementation mode
It is noted that following detailed description is all illustrative, it is intended to provide further instruction to the application.Unless another
It indicates, all technical and scientific terms used herein has usual with the application person of an ordinary skill in the technical field
The identical meanings of understanding.
It should be noted that term used herein above is merely to describe specific implementation mode, and be not intended to restricted root
According to the illustrative embodiments of the application.As used herein, unless the context clearly indicates otherwise, otherwise singulative
It is also intended to include plural form, additionally, it should be understood that, when in the present specification using term "comprising" and/or " packet
Include " when, indicate existing characteristics, step, operation, device, component and/or combination thereof.
With reference to specific embodiment, the present invention is described further.
One kind compared with high substituted degree etherification starch, be by cornstarch and nano-cellulose it is compound after carry out etherificate prepare institute
；The degree of substitution of existing converted starch is generally in 0.01-0.1, and the degree of substitution of carboxymethyl starch is higher, generally 0.2 or more；
Therefore, generally assert that 0.2 or more degree of substitution is high substituted degree.
The etherification starch is the etherification starch for catalyst preparation by nano-cellulose；
The catalyst is the nano micro crystal cellulose NCC that fibre length is 100-500nm；
The dosage that the nano-cellulose makees catalyst is 0.5%~5% (relative to starch dosage)；
The starch etherificate first mixes nano-cellulose with starch, and NaOH is added and carries out basification；
The starch etherifying agent is chloroacetic acid and sodium chloroacetate；
The present invention provides the catalyst of green non-pollution to carry out catalysis reaction, using chloroacetic acid and sodium chloroacetate as
Etherifying agent is modified.
In the present invention：Nano micro crystal cellulose or acquisition purchased in market are prepared using acid-hydrolysis method.Nano-cellulose plays catalysis
The effect of agent can improve the etherificate degree of starch, shorten etherification time.Nano-cellulose is added during starch etherificate,
The consumption of chemicals can be reduced, environmental pollution is reduced, additionally it is possible to improve starch etherificate degree.
The starch etherificate system is chloroacetic acid/nano-cellulose, sodium chloroacetate/nano-cellulose；
The application research is found：Since the length of nano-cellulose is nanoscale, it is easy to be inserted in starch
Layer expands the accessibility of starch and etherifying agent, and etherification starch is made to have compared with high substituted degree.For this purpose, the preferred Nanowire of the application
The length of dimension element is 100-500nm.The length of nano-cellulose it is smaller it is easier intercalation is carried out in starch, expand starch and ether
The accessibility of agent.
Nano-cellulose is 0.5%~5% (relative to starch dosage) as catalyst amount.
Etherification reaction is carried out again after nano-cellulose and starch mixing 0.5h.
Above-mentioned etherification starch preparation method：
It weighs 10-12g starch and is dissolved with 25-30ml absolute ethyl alcohols, 250ml three-necked flasks are poured into after being stirred with glass bar
In, 0.5-10wt% (relative to over dry starch quality) nano-cellulose is added, is stirred 0.5h, bath temperature is adjusted to 50
DEG C, a certain amount of NaOH alkalization 0.5-3h is added, a certain amount of etherifying agent is added to three-necked flask, after mechanical agitation 3-10h
Etherification reaction is terminated, centrifugation wash to sodium chloride-containing (uses silver nitrate not water-soluble in product with the methanol solution of volume fraction 80%
Liquid is examined), it is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains the etherificate of white powder
Starch.
The principle of the present invention：
Using nano-cellulose as catalyst, intercalation synthesis is carried out in starch, keeps etherification procedure more abundant；Nanowire
Dimension element has many advantages, such as big specific surface area, high intensity, can pass through nano-cellulose with the compound rear progress etherification reaction of starch
The etherification starch prepared after catalysis has higher degree of etherification falling.
It is noted that following detailed description is all illustrative, it is intended to provide further instruction to the application.Unless another
It indicates, all technical and scientific terms used herein has usual with the application person of an ordinary skill in the technical field
The identical meanings of understanding.
Embodiment 1
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 0.5wt% (relative to over dry starch quality) nano-cellulose, be stirred 0.5h, bath temperature is adjusted to 50 DEG C, is added
The NaOH alkalization 0.5h of 16wt%, the chloroacetic acid solution (a concentration of 70wt%) that 5wt% is added are added to three-necked flask, machinery
Etherification reaction is terminated after stirring 4h, wash and is centrifuged to sodium chloride-containing (does not use nitre in product with the methanol solution of volume fraction 80%
Sour silver aqueous solution is examined), it is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains white powder
The etherification starch of shape.
The degree of substitution that etherification product is measured with acidimetry, accurately weighs 0.5g samples, is placed in 50ml small beakers, is added
2mol/l HCl solution 40ml are filtered with magnetic stirrer 3h, then add the methanol solution washing acidification of volume fraction 80%
Sample afterwards, until not chloride ion-containing in cleaning solution.With the NaOH standard solution 40ml dissolvings of 0.1mol/L, make in a heated condition
Solution dissolves, and is taken off just with the anti-red for dropping to phenolphthalein indicator of the standard HCl solution of 0.1mol/L while hot, record is consumed
HCl standard solution volume, measure starch degree of substitution be 0.70, degree of substitution (DS) is calculated as follows：
MM number of the NaOH consumed with 1g acid carboxymethyl starch in A-；
VNaOHThe volume for the NaOH standard solution being added, ml；
CNaOHThe concentration of-NaOH standard solution, mol/L；
VHClThe volume of the HCl standard solution of the NaOH standard solution consumption of overtitration, ml；
CHClThe concentration of-HCl standard solution, mol/L；
Quality of the m- for the acid carboxymethyl starch of measurement, g；
MM number of the dehydration glucose unit of 0.162- starch；
After a hydroxyl is replaced by carboxymethyl in 0.058- dehydration glucose units, dehydration glucose unit mM quality
Net added value.
Embodiment 2
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 3wt% (relative to over dry starch quality) nano-cellulose, be stirred 0.5h, bath temperature is adjusted to 50 DEG C, is added
The NaOH alkalization 1h of 18wt%, the chloroacetic acid solution (a concentration of 70wt%) that 5wt% is added are added to three-necked flask, and machinery stirs
Etherification reaction is terminated after mixing 5h, centrifugation is washed to sodium chloride-containing (does not use nitric acid in product with the methanol solution of volume fraction 80%
Silver-colored aqueous solution is examined), it is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains white powder
Etherification starch.
The degree of substitution that etherification product is measured with acidimetry is 0.73.
Embodiment 3
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 5wt% (relative to over dry starch quality) nano-cellulose, be stirred 0.5h, bath temperature is adjusted to 50 DEG C, is added
The NaOH alkalization 2h of 20wt%, the chloroacetic acid solution (a concentration of 70wt%) that 5wt% is added are added to three-necked flask, and machinery stirs
Etherification reaction is terminated after mixing 6h, centrifugation is washed to sodium chloride-containing (does not use nitric acid in product with the methanol solution of volume fraction 80%
Silver-colored aqueous solution is examined), it is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains white powder
Etherification starch.
The degree of substitution that etherification product is measured with acidimetry is 0.81.
Embodiment 4
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 7wt% (relative to over dry starch quality) nano-cellulose, be stirred 0.5h, bath temperature is adjusted to 50 DEG C, is added
The NaOH alkalization 2h of 20wt%, the chloroacetic acid solution (a concentration of 70wt%) that 10wt% is added are added to three-necked flask, machinery
Etherification reaction is terminated after stirring 10h, wash and is centrifuged to sodium chloride-containing (does not use nitre in product with the methanol solution of volume fraction 80%
Sour silver aqueous solution is examined), it is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains white powder
The etherification starch of shape.
The degree of substitution that etherification product is measured with acidimetry is 0.85.
Embodiment 5
It weighs 12g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 9wt% (relative to over dry starch quality) nano-cellulose, be stirred 0.5h, bath temperature is adjusted to 50 DEG C, is added
The NaOH alkalization 3h of 20wt%, the chloroacetic acid solution (a concentration of 70wt%) that 20wt% is added are added to three-necked flask, machinery
Etherification reaction is terminated after stirring 10h, wash and is centrifuged to sodium chloride-containing (does not use nitre in product with the methanol solution of volume fraction 80%
Sour silver aqueous solution is examined), it is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains white powder
The etherification starch of shape.
The degree of substitution that etherification product is measured with acidimetry is 0.74.
Embodiment 6
It weighs 12g starch and is dissolved with 25ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 2wt% (relative to over dry starch quality) nano-cellulose, be stirred 0.5h, the NaOH alkalization 1h of 20wt% are added, it will
The sodium chloroacetate solution (a concentration of 50wt%) that 20wt% is added is added to three-necked flask, and it is anti-to terminate etherificate after mechanical agitation 3h
It answers, is washed with the methanol solution of volume fraction 80% and centrifuge into product not sodium chloride-containing (being examined with silver nitrate aqueous solution), and
PH is adjusted to neutrality with glacial acetic acid, and then the desciccate in 45 DEG C of baking ovens, obtains the etherification starch of white powder.
The degree of substitution that etherification product is measured with acidimetry is 0.47.
Embodiment 7
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 4wt% (relative to over dry starch quality) nano-cellulose, be stirred 0.5h, the NaOH of 20wt% is added in 40 DEG C of alkalization
1h, the sodium chloroacetate solution (a concentration of 50wt%) that 20wt% is added are added to three-necked flask, etherificate are terminated after mechanical agitation 4h
Reaction is washed with the methanol solution of volume fraction 80% and centrifuges into product not sodium chloride-containing (being examined with silver nitrate aqueous solution),
It is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains the etherification starch of white powder.
The degree of substitution that etherification product is measured with acidimetry is 0.55.
Embodiment 8
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 5wt% (relative to over dry starch quality) nano-cellulose, be stirred 0.5h, the NaOH of 20wt% is added in 50 DEG C of alkalization
1h, the sodium chloroacetate solution (a concentration of 50wt%) that 20wt% is added are added to three-necked flask, etherificate are terminated after mechanical agitation 6h
Reaction is washed with the methanol solution of volume fraction 80% and centrifuges into product not sodium chloride-containing (being examined with silver nitrate aqueous solution),
It is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains the etherification starch of white powder.
The degree of substitution that etherification product is measured with acidimetry is 0.57.
Embodiment 9
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 6wt% (relative to over dry starch quality) nano-cellulose, be stirred 0.5h, the NaOH of 20wt% is added in 40 DEG C of alkalization
1h, the sodium chloroacetate solution (a concentration of 50wt%) that 15wt% is added are added to three-necked flask, etherificate are terminated after mechanical agitation 4h
Reaction is washed with the methanol solution of volume fraction 80% and centrifuges into product not sodium chloride-containing (being examined with silver nitrate aqueous solution),
It is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains the etherification starch of white powder.
The degree of substitution that etherification product is measured with acidimetry is 0.52.
Embodiment 10
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 1wt% (relative to over dry starch quality) lignocellulosic, be stirred 0.5h, bath temperature is adjusted to 50 DEG C, is added
The NaOH alkalization 0.5h of 20wt%, the chloroacetic acid solution (a concentration of 50wt%) that 15wt% is added are added to three-necked flask, machine
Etherification reaction is terminated after tool stirring 5h, is washed with the methanol solution of volume fraction 80% and centrifuges into product sodium chloride-containing (use
Silver nitrate aqueous solution is examined), it is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains white powder
The etherification starch of last shape.
The degree of substitution that etherification product is measured with acidimetry, it is 0.18 to measure starch degree of substitution.
Embodiment 11
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 1wt% (relative to over dry starch quality) methylcellulose, be stirred 0.5h, bath temperature is adjusted to 50 DEG C, is added
The NaOH alkalization 0.5h of 20wt%, the chloroacetic acid solution (a concentration of 50wt%) that 20wt% is added are added to three-necked flask, machine
Etherification reaction is terminated after tool stirring 5h, is washed with the methanol solution of volume fraction 80% and centrifuges into product sodium chloride-containing (use
Silver nitrate aqueous solution is examined), it is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains white powder
The etherification starch of last shape.
The degree of substitution that etherification product is measured with acidimetry, it is 0.21 to measure starch degree of substitution.
Embodiment 12
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 1wt% (relative to over dry starch quality) hydroxypropyl methyl cellulose, be stirred 0.5h, bath temperature is adjusted to 50 DEG C,
The NaOH alkalization 3h of 18wt% are added, the sodium chloroacetate solution (a concentration of 50wt%) that 20wt% is added is added to three-necked flask,
Etherification reaction is terminated after mechanical agitation 5h, is washed with the methanol solution of volume fraction 80% and centrifuges into product not sodium chloride-containing
(being examined with silver nitrate aqueous solution) is used in combination glacial acetic acid to adjust pH to neutrality, and then the desciccate in 45 DEG C of baking ovens, obtains white
Powdered etherification starch.
The degree of substitution that etherification product is measured with acidimetry, it is 0.25 to measure starch degree of substitution.
Embodiment 13
It weighs 10g starch and is dissolved with 30ml absolute ethyl alcohols, pour into 250ml three-necked flasks, add after being stirred with glass bar
Enter 1wt% (relative to over dry starch quality) hydroxyethyl cellulose, be stirred 0.5h, bath temperature is adjusted to 50 DEG C, is added
The NaOH alkalization 1h of 20wt%, the sodium chloroacetate solution (a concentration of 50wt%) that 10wt% is added are added to three-necked flask, machinery
Etherification reaction is terminated after stirring 5h, wash and is centrifuged to sodium chloride-containing (does not use nitre in product with the methanol solution of volume fraction 80%
Sour silver aqueous solution is examined), it is used in combination glacial acetic acid to adjust pH to neutrality, then the desciccate in 45 DEG C of baking ovens, obtains white powder
The etherification starch of shape.
The degree of substitution that etherification product is measured with acidimetry, it is 0.19 to measure starch degree of substitution.
Finally it should be noted that the foregoing is only a preferred embodiment of the present invention, it is not limited to this hair
It is bright, although the present invention is described in detail referring to the foregoing embodiments, for those skilled in the art, still
It can modify to the technical solution recorded in previous embodiment, or equivalent replacement is carried out to which part.It is all in this hair
Within bright spirit and principle, any modification, equivalent replacement, improvement and so on should be included in protection scope of the present invention
Within.Although the above-mentioned specific implementation mode to the present invention is described, it is not intended to limit the protection scope of the present invention, institute
Belong to field technology personnel and should be understood that based on the technical solutions of the present invention those skilled in the art need not pay wound
The various modifications or changes that the property made labour can be made are still within protection scope of the present invention.
Claims (10)
1. a kind of preparation method of high substituted degree etherificate cornstarch, which is characterized in that micro- in nanometer by raw material of cornstarch
Under the conditions of crystalline cellulose is existing, high substituted degree etherification starch is prepared using solvent method；
The high substituted degree refers to that degree of substitution is more than 0.2；
The nano micro crystal cellulose is the nano micro crystal cellulose NCC of fibre length 100-500nm.
2. the method as described in claim 1, which is characterized in that the mass ratio of the cornstarch and nano micro crystal cellulose is
100：0.5~5.
3. the method as described in claim 1, which is characterized in that the solvent method the specific steps are：In certain density hydrogen
In sodium oxide molybdena-ethanol solution, cornstarch and nano micro crystal cellulose are alkalized；It adds etherifying agent to be etherified, ether
After the completion of changing reaction, washing centrifugation, to adjust pH value be neutrality, it is dry to get.
4. the method as described in claim 1, which is characterized in that the cornstarch, ethyl alcohol mass volume ratio be 10-12g:
25-30ml。
5. the method as described in claim 1, which is characterized in that the cornstarch, sodium hydroxide mass ratio be 100：16-
20。
6. the method as described in claim 1, which is characterized in that the etherifying agent is chloroacetic acid and sodium chloroacetate.
7. the method as described in claim 1, which is characterized in that the cornstarch, etherifying agent mass ratio be 100：5-20.
8. the method as described in claim 1, which is characterized in that the time of the quaternization is 40-50 DEG C of reaction 0.5-3h.
9. the method as described in claim 1, which is characterized in that the time of the etherification reaction is 40-50 DEG C of reaction 3-10h.
10. high substituted degree prepared by claim 1-9 any one of them methods is etherified cornstarch.
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| CN109369814A (en) * | 2018-11-29 | 2019-02-22 | 齐鲁工业大学 | A method of oxidation -ester composite modified starch |
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