AU2021105284A4 - An amino nanocellulose and a preparation method thereof - Google Patents
An amino nanocellulose and a preparation method thereof Download PDFInfo
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- AU2021105284A4 AU2021105284A4 AU2021105284A AU2021105284A AU2021105284A4 AU 2021105284 A4 AU2021105284 A4 AU 2021105284A4 AU 2021105284 A AU2021105284 A AU 2021105284A AU 2021105284 A AU2021105284 A AU 2021105284A AU 2021105284 A4 AU2021105284 A4 AU 2021105284A4
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- AU
- Australia
- Prior art keywords
- cellulose
- substituted amino
- amino compound
- nanocellulose
- halogen
- 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.)
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- 229920001046 Nanocellulose Polymers 0.000 title claims abstract description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 229920002678 cellulose Polymers 0.000 claims abstract description 59
- 239000001913 cellulose Substances 0.000 claims abstract description 59
- -1 amino compound Chemical class 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 235000010980 cellulose Nutrition 0.000 claims description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 29
- 239000003513 alkali Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 7
- 229920002749 Bacterial cellulose Polymers 0.000 claims description 6
- 239000005016 bacterial cellulose Substances 0.000 claims description 6
- 238000000265 homogenisation Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000011033 desalting Methods 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 239000003929 acidic solution Substances 0.000 claims description 4
- 238000002791 soaking Methods 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 238000004061 bleaching Methods 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 2
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 7
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 abstract description 5
- IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002121 nanofiber Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000003607 modifier Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 description 8
- 238000005576 amination reaction Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005265 energy consumption Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000001115 scanning electrochemical microscopy Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
- C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
Abstract
The present invention provides an amino nanocellulose and a preparation method thereof. In
the present invention, a water-soluble halogen-substituted amino compound (such as
bromoethylamine, chloropropylamine, etc.) is used as a modifier, and cellulose is used as a raw
material for the synthesis of amino nanofiber. The reaction of the present invention is carried out
under normal temperature and pressure and an aqueous phase conditions, so that the cost can be
reduced and the preparation process can be simplified, furthermore, the halogen-substituted amino
compound in the present invention can be recycled and reused after the reaction is completed.
Description
The present invention relates to an amino nanocellulose and a preparation method thereof, in particular to a method for preparing amino nanocellulose in an aqueous phase at normal temperature and pressure, and belongs to the technical field of the preparation of amino nanocellulose.
Cellulose is a natural compound with the largest reserves. Amino nanocellulose synthesized from cellulose as raw material is a high-quality industrial raw material and has a wide range of applications in chemical and biomedicine fields, and the like. At present, in the preparation of amino nanocellulose, nanocellulose is mainly used as a raw material. The crosslinking of amino groups with cellulose molecules is achieved through multi-step reactions in organic solvents, part of the reaction needs to be carried out under high temperature and high pressure conditions. The use of organic solvents can easily cause environmental pollutions, and the high temperature and high pressure reaction conditions will increase the energy consumption and cost of the preparation of amino nanocellulose. The present invention provides a method for synthesizing amino nanocellulose in an aqueous phase at normal temperature and normal pressure. Due to the normal temperature and normal pressure reaction conditions, the energy consumption in the preparation process of amino nanocellulose can be reduced; and in the crosslinking process of the amino group, no organic solvent is used, so that the risk of environmental pollutions can be avoided, and the cost of environmental disposal can be saved; cellulose is directly used as a raw material for the preparation of amino nanocellulose, no nanocellulose is prepared in advance, and the technical process is more simple.
The present invention provides a method for synthesizing cellulose through amination reaction in an aqueous phase under normal temperature and normal pressure, the involved cross-linking reaction of amino group is realized through a one-step reaction, such that the process of cellulose amination is simplified; In the preparation method of cellulose involved in the present invention, during the amination reaction of the cellulose, the hydrogen bonds between the fiber molecules are broken, such that the dispersion of the fibers can be accelerated. The nanocellulose can be prepared simply through ultrasonic, homogenization or other mechanical grinding. The technical solution of the present invention is summarized as follows:
A preparation method of amino nanocellulose is provided, wherein through the method, the amino nanocellulose is prepared in an aqueous phase under normal temperature and normal pressure, and the specific steps are as follows:
(1) Soaking the cellulose in water overnight at normal temperature, wherein the cellulose is added in an amount of 0.5 to 15% (g/mL); after uniformly stirring, adding an alkali solution such that the final concentration of the alkali solution is 4 to 30% (g/mL); sequentially soaking the same at normal temperature and normal pressure for a period of no less than 15 minutes; the main function of the alkali solution is to accelerate the dissolution or swelling of cellulose so as to provide conditions for subsequent reactions. Preferably, the alkali solution is selected from sodium hydroxide or potassium hydroxide.
(2) Adding a halogen-substituted amino compound in batches, and stirring constantly during the addition so as to accelerate the dispersion of the cellulose and the proceeding of the reaction, wherein the amount of the halogen-substituted amino compound is added in an amount of 5 to 100% based on the mole of the alkali solution; adding dropwise the halogen-substituted amino compound and then stirring continuously; dropwise adding an acidic solution to adjust the pH to neutral, desalting after the reaction is finished; or directly removing the alkali solution and the halogen-substituted amino compound by suction filtration thereby finishing the reaction; and then desorbing the alkali solution and the halogen-substituted amino compound adsorbed on the surface of cellulose. The positively charged carbon atoms in the halogen-substituted amino compound of the present invention can selectively combine with the negatively charged oxygen atoms in the cellulose molecule to form an ether bond, thereby binding the amino group to the surface of the cellulose, meanwhile destroying the hydrogen-bond interaction among cellulose molecules and improving the degree of dispersion of cellulose. Preferably, the halogen-substituted amino compound is selected from any one of a bromine-substituted amino compound, a chlorine-substituted amino compound, or an iodine-substituted amino compound; and the acidic solution is selected from any one of hydrochloric acid, nitric acid or acetic acid.
(3) Finally, subjecting the same to ultrasonic, homogenization, or other mechanical grinding treatments so as to obtain the amino nanocellulose.
Further, the cellulose is natural cellulose or artificially processed cellulose; the preferred natural cellulose is selected from lignocellulose or bacterial cellulose; and the artificially processed cellulose is microcrystalline cellulose.
Further, when the cellulose is a regenerated fiber, it needs to be treated through bleaching, drying, dispersing and cleaning.
The present invention further includes an amino nanocellulose obtained from the above preparation method.
In the present invention, a water-soluble halogen-substituted amino compound (such as bromoethylamine, chloropropylamine, etc.) is used as a modifier, and cellulose is used as a raw material for the synthesis of amino nanofiber. Because the cellulose exhibits dissolution or swelling effect in high-concentration alkali solutions (such as sodium hydroxide, potassium hydroxide, etc.), the hydrogen bonding effect among cellulose molecules can be reduced. At the same time, the hydrogen atoms on the hydroxyl groups of the cellulose molecules can be bonded with the alkali solution, forming a negatively charged oxygen on the surface of the cellulose molecule. In an alkali solution, halogen in the halogen-substituted amino compound is dissociated due to carrying an electron, so that the carbon atom adjacent to the halogen becomes positively charged. According to the mechanism of nucleophilic substitution, when the natural cellulose and the halogen-substituted amino compound are mixed in a strong alkali solution, the combination of the halogen-substituted amino compound and the cellulose molecule can be promoted, so that the amination of cellulose is realized. At the same time, the amino group crosslinked to the cellulose molecule can also reduce the hydrogen bonding effect among the cellulose molecules, so that the cellulose can be dispersed in the form of nanocellulose under the action of ultrasound, homogenization, or other mechanical grinding.
Compared with the prior art, the present invention has the following advantages:
(1) The reaction of the present invention is carried out under normal temperature and normal pressure and an aqueous phase condition, so that the energy consumption for the preparation of amino nanocellulose and the cost of equipment construction investment in the industrialization process can be effectively reduced; organic solvents can be avoided to be used due to the aqueous phase reaction condition, and thus the cost of environmental disposal can be reduced;
(2) There is no need to use nanocellulose as a raw material in the preparation process, thus the procedure of preparing nanocellulose in advance is avoided and the preparation process can be simplified;
(3) The cellulose is dissolved or swelled in an alkali solution, and then the halogen-substituted amino compound is bound to the cellulose molecule through a one-step reaction, thereby realizing the amination of the cellulose. On the one hand, in this process, the binding of the amino group on the surface of the cellulose molecule is achieved, on the other hand, the hydrogen-bond effect among cellulose molecules is destructed, such that the fibers can be dispersed easily, and the amino nanocellulose can be obtained after simple mechanical treatment. (4) The halogen-substituted amino compound in the present invention can be recycled and reused after the reaction is completed.
Figure 1 is a characterization diagram showing the distribution of C, N and 0 elements on the surface of aminocellulose molecules in the preparation of the present invention;
Figure 2 is a scanning electrochemical microscopy diagram showing the bacterial cellulose dispersion before and after amino modification in the present invention.
The present invention will be further described below in conjunction with specific embodiments, and the advantages and features of the present invention will become more obvious with reference to the description. However, the embodiments are only exemplary and do not constitute any limitation to the scope of the present invention. Those skilled in the art should understand that the details and forms of the technical solution of the present invention can be modified or replaced without departing from the spirit and scope of the present invention, but these modifications and replacements fall within the protection scope of the present invention.
Example 1: An amino nanocellulose and a preparation method thereof
The steps are as follows:
5% (g/mL) of cellulose was soaked in water under normal temperature and normal pressure overnight then uniformly stirred. A sodium hydroxide solution was added, such that the final concentration of the sodium hydroxide solution was 10% (g/mL). Subsequently, the obtained mixture was soaked under normal temperature and normal pressure for 1 hour, and then bromoethylamine was added dropwise while stirred, the total amount added thereof was 40% based on the mole of potassium hydroxide. Then continuously stirring was performed for 2 hours. Hydrochloric acid solution was added dropwise to adjust the pH to neutral. After the reaction was completed, desalting was performed. After an ultrasonic treatment, the amino nanocellulose was obtained
Example 2: An amino nanocellulose and a preparation method thereof
The steps are as follows:
1% (g/mL) of cellulose was soaked in water under normal temperature and normal pressure overnight, then uniformly stirred. A sodium hydroxide was added, such that the final concentration of the sodium hydroxide solution was 5% (g/mL). Subsequently, the obtained mixture was soaked under normal temperature and normal pressure for 1.5 hours, and then chloropropylamine was added dropwise while stirred, the amount added thereof was 10% based on the mole of sodium hydroxide. Then, continuously stirring was performed for 1 hour after the addition was completed. Then a suction filtration in a Teflon funnel was performed so as to remove the unreacted sodium hydroxide and chlorpropylamine. Washing with water was performed for multiple times so as to remove the sodium hydroxide and chlorpropylamine remaining on the surface of the cellulose. The amino nanocellulose was obtained after a mechanical treatment.
Example 3: An amino nanocellulose and a preparation method thereof
The steps are as follows:
10% (g/mL) of cellulose was soaked in distilled water under normal temperature and normal pressure overnight, then uniformly stirred. A potassium hydroxide solution was added, such that the final concentration of the sodium hydroxide solution was 30% (g/mL). Subsequently, the obtained mixture was soaked under normal temperature and normal pressure for 2.5 hours, and then iodoacetamide was added dropwise, the amount added thereof was 70% based on the mole of sodium hydroxide. Then continuously stirring was performed for 2 hours. An acetic acid solution was added dropwise to adjust the pH to neutral. After the reaction was completed, desalting was performed. The amino nanocellulose was obtained after ultrasonic and homogenization treatments.
Example 4: An amino nanocellulose and a preparation method thereof
The steps are as follows:
4% (g/mL) of cellulose was soaked under normal temperature and normal pressure overnight, then uniformly stirred. A potassium hydroxide solution was added, such that the final concentration of the sodium hydroxide solution was 18% (g/mL). Subsequently, the obtained mixture was soaked under normal temperature and normal pressure for 1.5 hours, and then bromoethylamine was added dropwise, the amount added thereof was 60% based on the mole of potassium hydroxide. Then, continuously stirring was performed for 1.5 hours. A hydrochloric acid solution was added dropwise to adjust the pH to neutral. After the reaction was completed, desalting was performed. The amino nanocellulose was obtained after ultrasonic, homogenization, or other mechanical grinding treatments.
Test Example
According to the X-ray energy spectrum test, the characterization diagram showing the distribution of C, N and 0 elements on the surface of amino nanocellulose obtained by the present invention is shown in Figure 1. The distribution diagram of the nitrogen element indicates that the amino group is uniformly crosslinked to the surface of cellulose. The dispersibility of the amino bacterial cellulose prepared by the method described in the present invention is shown in Figure 2. Although the bacterial cellulose is homogenized before amination and crosslinking (Figure 2A), good dispersibility still cannot be achieved. After amino group was crosslinked to the surface of bacterial cellulose in the method described in the present invention, the dispersibility of cellulose can be significantly improved (Figure 2B). It can be proved from Figure 2 that in the amino modification process described in this patent, the hydrogen-bond effect among cellulose molecules can be destructed, and thus the dispersibility of cellulose can be improved, the difficulties of subsequent mechanical treatments can be reduced, as a result, the rapid preparation of aminated nanocellulose can be realized. In this preparation solution, the traditional preparation process of the amino nanocellulose is broken, wherein the nanofibers is prepared firstly and then amino modifying is performed. Therefore, the preparation process of the amino nanocellulose can be carried out easily and conveniently, and energy consumption is low.
Claims (9)
1. An amino nanocellulose, characterized in that, it is obtained through the method comprising the steps as follows
(1) Soaking the cellulose in water overnight at normal temperature, wherein the cellulose is added in an amount of 0.5 to 15% (g/mL); after uniformly stirring, adding an alkali solution such that the final concentration of the alkali solution is 4 to 30% (g/mL); sequentially soaking the same at normal temperature and normal pressure for a period of no less than 15 minutes;
(2) Adding a halogen-substituted amino compound in batches, and stirring constantly during the addition so as to accelerate the dispersion of the cellulose and the proceeding of the reaction, wherein the amount of the halogen-substituted amino compound is added in an amount of 5 to 100% based on the mole of the alkali solution; adding dropwise the halogen-substituted amino compound and then stirring continuously; dropwise adding an acidic solution so as to adjust the pH to neutral, desalting after the reaction is finished; or directly removing the alkali solution and the halogen-substituted amino compound by suction filtration thereby finishing the reaction; and then desorpting the alkali solution and the halogen-substituted amino compound adsorbed on the surface of cellulose;
(3) Finally, subjecting the same to ultrasonic, homogenization, or other mechanical grinding treatments so as to obtain the amino nanocellulose.
2. The method according to claim 1, characterized in that, the cellulose in the step (1) is natural cellulose or artificially processed cellulose.
3. The method according to claim 2, characterized in that, the natural cellulose in the step (1) is selected from lignocellulose or bacterial cellulose.
4. The method according to claim 2, characterized in that, the artificially processed cellulose in the step (1) is microcrystalline cellulose.
5. The method according to claim 1, characterized in that, in the step (1), when the cellulose is a regenerated fiber, it needs to be treated through bleaching, drying, dispersing and cleaning.
6. The preparation method according to claim 1, characterized in that, the alkali solution in the step (1) is selected from sodium hydroxide or potassium hydroxide.
7. The preparation method according to claim 1, characterized in that, the halogen-substituted amino compound in the step (2) is selected from any one of a bromine-substituted amino compound, a chlorine-substituted amino compound, or an iodine-substituted amino compound.
8. The preparation method according to claim 1, characterized in that, the acidic solution in the step (2) is selected from any one of hydrochloric acid, nitric acid or acetic acid.
9. An amino nanocellulose obtained from the preparation method according to any one of claims I to 8.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110569543.5A CN113307889A (en) | 2021-05-25 | 2021-05-25 | Amino nano-cellulose and preparation method thereof |
| CN2021105695435 | 2021-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2021105284A4 true AU2021105284A4 (en) | 2021-10-07 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2021105284A Ceased AU2021105284A4 (en) | 2021-05-25 | 2021-08-11 | An amino nanocellulose and a preparation method thereof |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN113307889A (en) |
| AU (1) | AU2021105284A4 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004035869A1 (en) * | 2004-07-23 | 2006-03-16 | Wolff Cellulosics Gmbh & Co. Kg | Process for the preparation of amino group-containing cellulose derivatives and their use in cosmetic preparations of water treatment and papermaking |
| CN103881117B (en) * | 2014-02-19 | 2016-02-24 | 浙江理工大学 | A kind of preparation method of surface-functionalized cellulose nanospheres |
-
2021
- 2021-05-25 CN CN202110569543.5A patent/CN113307889A/en active Pending
- 2021-08-11 AU AU2021105284A patent/AU2021105284A4/en not_active Ceased
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| Publication number | Publication date |
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| CN113307889A (en) | 2021-08-27 |
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| FGI | Letters patent sealed or granted (innovation patent) | ||
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