CN106892984A - A kind of Cellulose nanocrystal of surface modification and its preparation method and application - Google Patents
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- 239000002159 nanocrystal Substances 0.000 title claims abstract description 39
- 239000001913 cellulose Substances 0.000 title claims abstract description 38
- 229920002678 cellulose Polymers 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 230000004048 modification Effects 0.000 title claims abstract description 8
- 238000012986 modification Methods 0.000 title claims abstract description 8
- 239000000047 product Substances 0.000 claims abstract description 23
- 239000000243 solution Substances 0.000 claims abstract description 9
- 235000013305 food Nutrition 0.000 claims abstract description 7
- 239000012153 distilled water Substances 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 6
- 239000011259 mixed solution Substances 0.000 claims abstract description 6
- 239000000843 powder Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 230000036541 health Effects 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 238000012545 processing Methods 0.000 claims abstract description 4
- FLISWPFVWWWNNP-BQYQJAHWSA-N dihydro-3-(1-octenyl)-2,5-furandione Chemical compound CCCCCC\C=C\C1CC(=O)OC1=O FLISWPFVWWWNNP-BQYQJAHWSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000010008 shearing Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 abstract description 7
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000000839 emulsion Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000002715 modification method Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003473 lipid group Chemical group 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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Abstract
本发明属于纤维素纳米晶改性技术领域，公开了一种表面修饰的纤维素纳米晶及其制备方法和应用。所述制备方法为：将CNC用蒸馏水稀释，得到质量浓度为1～50g/L的CNC溶液，然后加入OSA均质混合均匀，将所得混合溶液冷冻干燥，然后在40～125℃加热反应5～240min，反应产物经洗涤、干燥、研磨，得到表面修饰的纤维素纳米晶粉末。本发明利用OSA改性CNC，可以大大提高CNC的疏水性，且不会破坏其晶体结构，可应用于保健产品、药品或食品加工领域。The invention belongs to the technical field of cellulose nanocrystal modification, and discloses a surface-modified cellulose nanocrystal, a preparation method and application thereof. The preparation method is as follows: Dilute CNC with distilled water to obtain a CNC solution with a mass concentration of 1 to 50 g/L, then add OSA and mix evenly, freeze-dry the obtained mixed solution, and then heat and react at 40 to 125°C for 5 to 5 ~ After 240 minutes, the reaction product was washed, dried and ground to obtain surface-modified cellulose nanocrystal powder. The invention uses OSA to modify the CNC, which can greatly improve the hydrophobicity of the CNC without destroying its crystal structure, and can be applied to the fields of health care products, medicines or food processing.
Description
技术领域technical field
本发明属于纤维素纳米晶改性技术领域，具体涉及一种表面修饰的纤维素纳米晶及其制备方法和应用。The invention belongs to the technical field of cellulose nanocrystal modification, and in particular relates to a surface-modified cellulose nanocrystal and its preparation method and application.
背景技术Background technique
纤维素纳米晶具有生物相容性、生物可降解性，且价廉易得，因此，其作为乳化剂、稳定剂、凝胶剂配方等来形成化工产品，如食品、药品、家庭清洁产品和个人护理产品等方面有极大前景。但由于纤维素纳米晶表面含有大量羟基，因而表现出极强的亲水性，这就限制了其在许多方面的应用，如作为稳定剂稳定皮克林乳液等。Cellulose nanocrystals are biocompatible, biodegradable, and cheap and easy to obtain. Therefore, they are used as emulsifiers, stabilizers, gel formulations, etc. to form chemical products, such as food, pharmaceuticals, household cleaning products and Personal care products have great prospects. However, because the surface of cellulose nanocrystals contains a large number of hydroxyl groups, it exhibits extremely strong hydrophilicity, which limits its application in many aspects, such as stabilizing Pickering emulsions as a stabilizer.
为了解决上诉问题，改善CNC的疏水性，提高其稳定乳液、吸油等能力，进而扩宽CNC的应用范围，可以对其进行修饰改性。但目前用于CNC修饰改性的方法要么会用到强酸、离子溶剂、催化剂等不符合食品安全的有毒试剂，要么就是需要在高温条件下进行，或是需要较长时间，或是会改变纤维素纳米晶的晶体结构，或是改性程度极低。因而寻找不会破坏纤维素纳米晶的晶体结构，且改性方法简单，改性条件容易，无毒、安全、高效且价格低廉的改性方法十分重要。In order to solve the appeal problem, improve the hydrophobicity of CNC, improve its ability to stabilize emulsion, oil absorption, etc., and then broaden the application range of CNC, it can be modified. However, the current methods for CNC modification either use strong acids, ionic solvents, catalysts and other toxic reagents that do not meet food safety, or need to be carried out under high temperature conditions, or take a long time, or will change the fiber The crystal structure of plain nanocrystals, or the degree of modification is extremely low. Therefore, it is very important to find a non-toxic, safe, efficient and low-cost modification method that will not destroy the crystal structure of cellulose nanocrystals, and has a simple modification method and easy modification conditions.
发明内容Contents of the invention
为了解决以上现有技术的缺点和不足之处，本发明的首要目的在于提供一种表面修饰的纤维素纳米晶的制备方法。In order to solve the above shortcomings and deficiencies of the prior art, the primary purpose of the present invention is to provide a method for preparing surface-modified cellulose nanocrystals.
本发明的另一目的在于提供一种通过上述方法制备得到的表面修饰的纤维素纳米晶。Another object of the present invention is to provide a surface-modified cellulose nanocrystal prepared by the above method.
本发明的再一目的在于提供上述表面修饰的纤维素纳米晶在保健产品、药品或食品加工领域中的应用。Another object of the present invention is to provide the application of the above-mentioned surface-modified cellulose nanocrystals in the fields of health care products, medicines or food processing.
本发明目的通过以下技术方案实现：The object of the invention is achieved through the following technical solutions:
一种表面修饰的纤维素纳米晶的制备方法，包括如下制备步骤：A method for preparing a surface-modified cellulose nanocrystal, comprising the following preparation steps:
将纤维素纳米晶(CNC)用蒸馏水稀释，得到质量浓度为1～50g/L的CNC溶液，然后加入辛烯基琥珀酸酐(OSA)均质混合均匀，将所得混合溶液冷冻干燥，然后在40～125℃加热反应5～240min，反应产物经洗涤、干燥、研磨，得到表面修饰的纤维素纳米晶(OSA-CNC)粉末。Dilute the cellulose nanocrystals (CNC) with distilled water to obtain a CNC solution with a mass concentration of 1 to 50 g/L, then add octenyl succinic anhydride (OSA) and mix homogeneously, freeze-dry the resulting mixed solution, and then dry it at 40 ~125°C heating reaction for 5~240min, the reaction product is washed, dried, and ground to obtain surface-modified cellulose nanocrystal (OSA-CNC) powder.
优选地，所述OSA的添加量为CNC净含量的0.25～20倍。Preferably, the amount of OSA added is 0.25-20 times the net content of CNC.
优选地，所述CNC溶液的质量浓度为20g/L，所述OSA的添加量为CNC的2倍。Preferably, the mass concentration of the CNC solution is 20g/L, and the amount of OSA added is twice that of CNC.
优选地，所述均质混合均匀是指在8000～30000rpm条件下剪切均质1～5min，更优选在剪切转速为25600rpm条件下均质1min。Preferably, the homogeneous mixing refers to shearing and homogenizing at 8000-30000 rpm for 1-5 minutes, more preferably at a shearing speed of 25600 rpm for 1 minute.
优选地，所述加热反应的温度为45～105℃，时间为5～60min。Preferably, the temperature of the heating reaction is 45-105° C., and the time is 5-60 minutes.
优选地，所述的洗涤是指用乙醇洗涤除去残余OSA，具体过程为：将反应产物分散于体积浓度为90％乙醇中，然后10000rpm离心15min，反复分散离心三次。Preferably, the washing refers to washing with ethanol to remove residual OSA, and the specific process is as follows: the reaction product is dispersed in ethanol with a volume concentration of 90%, and then centrifuged at 10000 rpm for 15 minutes, and the dispersion and centrifugation are repeated three times.
优选地，所述的干燥是指在37～45℃干燥15～24h，更优选在37℃干燥18h。Preferably, the drying refers to drying at 37-45°C for 15-24 hours, more preferably at 37°C for 18 hours.
一种表面修饰的纤维素纳米晶，通过上述方法制备得到。A surface-modified cellulose nanocrystal is prepared by the above method.
上述表面修饰的纤维素纳米晶在保健产品、药品或食品加工领域中的应用。Application of the above-mentioned surface-modified cellulose nanocrystals in the fields of health care products, medicines or food processing.
本发明的制备方法及所得到的产物具有如下优点及有益效果：The preparation method of the present invention and the resulting product have the following advantages and beneficial effects:
(1)本发明利用OSA改性CNC，可以大大提高CNC的疏水性；(1) The present invention utilizes OSA to modify CNC, which can greatly improve the hydrophobicity of CNC;
(2)本发明的改性方法条件温和，反应时间短；(2) The modified method of the present invention has mild conditions and short reaction times;
(3)本发明的改性方法涉及的工艺简单、安全，适合于食品工业的应用；(3) The process involved in the modification method of the present invention is simple and safe, and is suitable for application in the food industry;
(4)本发明的改性方法只对CNC的表面进行修饰，不会破坏其晶体结构；(4) The modification method of the present invention only modifies the surface of CNC, without destroying its crystal structure;
(5)本发明所得OSA-CNC不仅可以作为稳定剂稳定皮克林乳液，还可以作为载体包埋活性物质、抗癌物质等，进而广泛地应用于保健食品、药品的开发。(5) The OSA-CNC obtained in the present invention can not only be used as a stabilizer to stabilize Pickering emulsion, but also can be used as a carrier to embed active substances, anticancer substances, etc., and then be widely used in the development of health food and medicine.
具体实施方式detailed description
下面结合实施例对本发明作进一步详细的描述，但本发明的实施方式不限于此。The present invention will be further described in detail below in conjunction with examples, but the embodiments of the present invention are not limited thereto.
实施例1Example 1
(1)常温下，通过低速的搅拌手段，用蒸馏水将CNC稀释至20g/L；(1) Dilute the CNC to 20g/L with distilled water by low-speed stirring at room temperature;
(2)在匀速搅拌下，按照OSA:CNC＝2:1的质量比将OSA添加到CNC溶液中；(2) under constant stirring, add OSA to the CNC solution according to the mass ratio of OSA:CNC=2:1;
(3)将CNC和OSA的混合溶液在25600rpm条件下剪切均质1min，使其充分混合，得到混合充分的乳状液；(3) shear and homogenize the mixed solution of CNC and OSA at 25600rpm for 1min, make it fully mixed, and obtain a fully mixed emulsion;
(4)将乳状液置于冷冻干燥机中冻干，然后45℃加热反应60min；(4) Place the emulsion in a lyophilizer to lyophilize, then heat and react at 45°C for 60min;
(5)将反应后的产物分散在90％乙醇中，以10000rpm速度离心15分钟，反复分散离心3遍，除去残余的OSA；(5) Disperse the reacted product in 90% ethanol, centrifuge at a speed of 10000rpm for 15 minutes, repeat the dispersion and centrifugation for 3 times, and remove residual OSA;
(6)将乙醇洗过的样品置于烘箱中，37℃烘18h，然后研磨，得到干燥的OSA-CNC粉末。(6) Place the ethanol-washed sample in an oven, bake at 37°C for 18 hours, and then grind to obtain dry OSA-CNC powder.
在本实施例的条件下，得到的改性产物取代度为0.0361，产物的平均粒径为149.17±2.86nm；将该产物通过红外光谱仪测定纤维素纳米晶表面带有大量脂基和酰基；将该产物通过X射线衍射仪测定纤维素纳米晶的晶体结构没有被破坏；将该产物通过疏水性测试，发现其疏水性显著提高，可以分散在非极性溶剂中。Under the conditions of the present embodiment, the degree of substitution of the obtained modified product is 0.0361, and the average particle diameter of the product is 149.17 ± 2.86nm; the product is measured by an infrared spectrometer with a large number of lipid groups and acyl groups on the surface of the cellulose nanocrystal; The crystal structure of the cellulose nanocrystal is not destroyed as determined by the X-ray diffractometer; the hydrophobicity test of the product shows that its hydrophobicity is significantly improved and can be dispersed in a non-polar solvent.
实施例2Example 2
(1)常温下，通过低速的搅拌手段，用蒸馏水将CNC稀释至20g/L；(1) Dilute the CNC to 20g/L with distilled water by low-speed stirring at room temperature;
(2)在匀速搅拌下，按照OSA:CNC＝2:1的质量比将OSA添加到CNC溶液中；(2) under constant stirring, add OSA to the CNC solution according to the mass ratio of OSA:CNC=2:1;
(3)将CNC和OSA的混合溶液在25600rpm条件下剪切均质1min，使其充分混合，得到混合充分的乳状液；(3) shear and homogenize the mixed solution of CNC and OSA at 25600rpm for 1min, make it fully mixed, and obtain a fully mixed emulsion;
(4)将乳状液置于冷冻干燥机中冻干，然后65℃加热反应60min；(4) Place the emulsion in a lyophilizer to lyophilize, then heat and react at 65°C for 60min;
(5)将反应后的产物分散在90％乙醇中，以10000rpm速度离心15分钟，反复分散离心3遍，除去残余的OSA；(5) Disperse the reacted product in 90% ethanol, centrifuge at a speed of 10000rpm for 15 minutes, repeat the dispersion and centrifugation for 3 times, and remove residual OSA;
(6)将乙醇洗过的样品置于烘箱中，37°烘18h，然后研磨，得到干燥的OSA-CNC粉末。(6) Place the ethanol-washed sample in an oven, bake at 37° for 18 hours, and then grind to obtain dry OSA-CNC powder.
在本实施例的条件下，得到的改性产物取代度为0.0456，产物的平均粒径为169.07±4.84nm；将该产物通过红外光谱仪测定纤维素纳米晶表面带有大量脂基和酰基；将该产物通过X射线衍射仪测定纤维素纳米晶的晶体结构没有被破坏；将该产物通过疏水性测试，发现其疏水性显著提高，可以分散在非极性溶剂中。Under the conditions of the present embodiment, the degree of substitution of the obtained modified product is 0.0456, and the average particle diameter of the product is 169.07 ± 4.84nm; the product is measured by an infrared spectrometer with a large number of lipid groups and acyl groups on the surface of the cellulose nanocrystal; The crystal structure of the cellulose nanocrystal is not destroyed as determined by the X-ray diffractometer; the hydrophobicity test of the product shows that its hydrophobicity is significantly improved and can be dispersed in a non-polar solvent.
实施例3Example 3
(1)常温下，通过低速的搅拌手段，用蒸馏水将CNC稀释至20g/L；(1) Dilute the CNC to 20g/L with distilled water by low-speed stirring at room temperature;
(2)在匀速搅拌下，按照OSA:CNC＝2:1的质量比将OSA添加到CNC溶液中；(2) under constant stirring, add OSA to the CNC solution according to the mass ratio of OSA:CNC=2:1;
(3)将CNC和OSA的混合溶液在25600rpm条件下剪切均质1min，使其充分混合，得到混合充分的乳状液；(3) shear and homogenize the mixed solution of CNC and OSA at 25600rpm for 1min, make it fully mixed, and obtain a fully mixed emulsion;
(4)将乳状液置于冷冻干燥机中冻干，然后105℃加热反应5min；(4) Place the emulsion in a lyophilizer to lyophilize, then heat and react at 105°C for 5 minutes;
(5)将反应后的产物分散在90％乙醇中，以10000rpm速度离心15分钟，反复分散离心3遍，除去残余的OSA；(5) Disperse the reacted product in 90% ethanol, centrifuge at a speed of 10000rpm for 15 minutes, repeat the dispersion and centrifugation for 3 times, and remove residual OSA;
(6)将乙醇洗过的样品置于烘箱中，37℃烘18h，然后研磨，得到干燥的OSA-CNC粉末。(6) Place the ethanol-washed sample in an oven, bake at 37°C for 18 hours, and then grind to obtain dry OSA-CNC powder.
在本实施例的条件下，得到的改性产物取代度为0.0424，产物的平均粒径为155.06±1.04nm；将该产物通过红外光谱仪测定纤维素纳米晶表面带有大量脂基和酰基；将该产物通过X射线衍射仪测定纤维素纳米晶的晶体结构没有被破坏；将该产物通过疏水性测试，发现其疏水性显著提高，可以分散在非极性溶剂中。Under the conditions of the present embodiment, the degree of substitution of the obtained modified product is 0.0424, and the average particle diameter of the product is 155.06 ± 1.04nm; the product is measured by an infrared spectrometer with a large number of lipid groups and acyl groups on the surface of the cellulose nanocrystal; The crystal structure of the cellulose nanocrystal is not destroyed as determined by the X-ray diffractometer; the hydrophobicity test of the product shows that its hydrophobicity is significantly improved and can be dispersed in a non-polar solvent.
上述实施例为本发明较佳的实施方式，但本发明的实施方式并不受上述实施例的限制，其它的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化，均应为等效的置换方式，都包含在本发明的保护范围之内。The above-mentioned embodiment is a preferred embodiment of the present invention, but the embodiment of the present invention is not limited by the above-mentioned embodiment, and any other changes, modifications, substitutions, combinations, Simplifications should be equivalent replacement methods, and all are included in the protection scope of the present invention.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107938332A (en) * | 2017-11-08 | 2018-04-20 | 浙江理工大学 | A kind of Cellulose nanocrystal must hydrophobic modification method |
| CN110343260A (en) * | 2018-11-12 | 2019-10-18 | 中国林业科学研究院林产化学工业研究所 | A kind of modified cellulose Nanowire stablizes Pickering lotion and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107938332A (en) * | 2017-11-08 | 2018-04-20 | 浙江理工大学 | A kind of Cellulose nanocrystal must hydrophobic modification method |
| CN110343260A (en) * | 2018-11-12 | 2019-10-18 | 中国林业科学研究院林产化学工业研究所 | A kind of modified cellulose Nanowire stablizes Pickering lotion and preparation method thereof |
| WO2020148579A1 (en) * | 2019-01-17 | 2020-07-23 | Glasing Joe | Emulsions and methods of making the same |
| CN116120470A (en) * | 2023-02-08 | 2023-05-16 | 福建省农业科学院农业工程技术研究所 | A kind of preparation method of bamboo shoot OSNC, the product made and application thereof |
| CN116120470B (en) * | 2023-02-08 | 2025-03-28 | 福建省农业科学院农业工程技术研究所 | A method for preparing bamboo shoot OSNC, a product prepared therefrom and its application |
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