CN108690206A - A kind of citral pickering emulsion and preparation method thereof that nano-cellulose is stablized - Google Patents
A kind of citral pickering emulsion and preparation method thereof that nano-cellulose is stablized Download PDFInfo
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- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 229940043350 citral Drugs 0.000 title claims abstract description 71
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 title claims abstract description 71
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 229920002678 cellulose Polymers 0.000 title abstract description 6
- 239000001913 cellulose Substances 0.000 title abstract description 6
- 238000001484 Pickering emulsion method Methods 0.000 title 1
- 229920001046 Nanocellulose Polymers 0.000 claims abstract description 84
- 239000000725 suspension Substances 0.000 claims abstract description 59
- 239000000839 emulsion Substances 0.000 claims abstract description 52
- 239000000843 powder Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000265 homogenisation Methods 0.000 claims abstract description 14
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims abstract description 12
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims abstract description 12
- 239000008108 microcrystalline cellulose Substances 0.000 claims abstract description 12
- 229940016286 microcrystalline cellulose Drugs 0.000 claims abstract description 12
- 239000007853 buffer solution Substances 0.000 claims abstract description 9
- XPFJYKARVSSRHE-UHFFFAOYSA-K trisodium;2-hydroxypropane-1,2,3-tricarboxylate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [Na+].[Na+].[Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O XPFJYKARVSSRHE-UHFFFAOYSA-K 0.000 claims abstract description 9
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 88
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 44
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 13
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000003760 magnetic stirring Methods 0.000 claims description 6
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 abstract description 9
- 229940057917 medium chain triglycerides Drugs 0.000 abstract description 7
- 238000006731 degradation reaction Methods 0.000 abstract description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract description 3
- 235000011130 ammonium sulphate Nutrition 0.000 abstract description 3
- 230000015556 catabolic process Effects 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000002245 particle Substances 0.000 description 11
- 230000014759 maintenance of location Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 235000005979 Citrus limon Nutrition 0.000 description 3
- 244000131522 Citrus pyriformis Species 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 241000208140 Acer Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000019499 Citrus oil Nutrition 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000010500 citrus oil Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 239000001289 litsea cubeba fruit oil Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- -1 monoterpene compound Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 239000007908 nanoemulsion Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 235000021578 orange juice drink Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
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- C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
- C08J3/095—Oxygen containing compounds
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- 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
- C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
- C08J2301/04—Oxycellulose; Hydrocellulose
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Abstract
本发明提供了一种利用纳米纤维素稳定的柠檬醛皮克林乳液的制备方法，是以微晶纤维素为原材料，经过硫酸铵氧化改性后，通过水洗得到纳米纤维素悬浮液；将此悬浮液冷冻干燥，得到纳米纤维素粉末；将纳米纤维素粉末分散于pH为3的柠檬酸‑柠檬酸钠酸性缓冲溶液中，形成纳米纤维素悬浮液，随后向上述悬浮液中加入柠檬醛和中链甘油三酯，通过高速均质，得到柠檬醛皮克林乳液。本发明制备的柠檬醛皮克林乳液具有纳米纤维素用量少、制备过程简单及应用成本低等特点，能有效提高酸性条件下柠檬醛的稳定性，延缓其降解。
The invention provides a method for preparing a citral Pickering emulsion stabilized by nanocellulose, which uses microcrystalline cellulose as a raw material, and after being oxidized and modified by ammonium sulfate, is washed with water to obtain a nanocellulose suspension; The suspension is freeze-dried to obtain nanocellulose powder; the nanocellulose powder is dispersed in a citric acid-sodium citrate acidic buffer solution with a pH of 3 to form a nanocellulose suspension, and then citral and medium-chain triglycerides, by high-speed homogenization, to obtain a citral Pickering emulsion. The citral Pickering emulsion prepared by the invention has the characteristics of less nano-cellulose consumption, simple preparation process and low application cost, can effectively improve the stability of citral under acidic conditions, and delay its degradation.
Description
技术领域technical field
本发明属于食品化工领域，涉及一种柠檬醛皮克林乳液，具体来说是一种纳米纤维素稳定的柠檬醛皮克林乳液及其制备方法。The invention belongs to the field of food chemical industry, and relates to a citral Pickering emulsion, in particular to a nanocellulose-stabilized citral Pickering emulsion and a preparation method thereof.
背景技术Background technique
柠檬醛是一种脂溶性、易挥发的开链单萜化合物，主要存在于山苍子油和枫茅油中，是一种具有广阔应用前景的天然香料，也是合成高级香料的重要原料之一，其特有的柠檬香气可以给人带来愉悦的清新感觉，因此，柠檬醛常用作饮料、糕点等食品的调味、增香，也可用于调制柑桔油、柠檬油和柠檬香精。同时，柠檬醛也是一种广谱的抗菌剂和天然防腐剂。Citral is a fat-soluble, volatile open-chain monoterpene compound, which mainly exists in litsea cubeba oil and maple grass oil. It is a natural fragrance with broad application prospects and one of the important raw materials for the synthesis of high-grade fragrances , Its unique lemon aroma can bring a pleasant and fresh feeling to people. Therefore, citral is often used as seasoning and flavoring of beverages, cakes and other foods, and can also be used to prepare citrus oil, lemon oil and lemon essence. At the same time, citral is also a broad-spectrum antibacterial agent and natural preservative.
但是柠檬醛结构中存在羰基和双键，极易发生缩合、加成、氧化和环化等化学反应。尤其在酸性环境下，会加快其降解反应速度，生成许多令人不愉快的异味化合物，导致新鲜柠檬气息的损失。而大多数的橙类果汁饮料为酸性，柠檬醛的这一性质严重制约了其在饮料和香料行业的应用。However, there are carbonyl groups and double bonds in the structure of citral, which are prone to chemical reactions such as condensation, addition, oxidation and cyclization. Especially in an acidic environment, its degradation reaction speed will be accelerated, and many unpleasant odor compounds will be generated, resulting in the loss of fresh lemon smell. However, most orange juice drinks are acidic, and this property of citral seriously restricts its application in the beverage and flavor industries.
在食品加工工艺中，以乳液为基础的运载体系应用广泛，通过乳液输送体系能够包裹、保护和释放食品中的功能性营养成分，从而使其在保存期间不易被氧化，提高产品的风味质量和营养品质，延长其货架期。目前多采用水包油乳液、纳米乳液和多层乳液对柠檬醛进行包埋。但是这些乳液只是动力学稳定系统，长期储存容易发生聚集和分层等现象。In food processing technology, the emulsion-based delivery system is widely used. The emulsion delivery system can wrap, protect and release the functional nutrients in food, so that it is not easy to be oxidized during storage, and the flavor quality and quality of the product can be improved. Nutritional qualities, prolonging its shelf life. At present, oil-in-water emulsion, nanoemulsion and multi-layer emulsion are mostly used to embed citral. However, these emulsions are only kinetically stable systems, and aggregation and delamination are prone to occur in long-term storage.
皮克林乳液是指由固体颗粒稳定乳液体系的新型乳液，其稳定机理是固体颗粒在油水界面形成不可逆吸附，从而形成空间位阻效应阻碍液滴之间的聚并，同时，固体颗粒之间相互缠结形成的网络结构在一定程度上增加了乳液的稳定性。与小分子表面活性剂稳定的乳液相比，该体系具有抗聚集、抗絮凝、抗奥氏化成熟和稳定性好等优势。近年来，一些食品级的固体颗粒如多糖、蛋白质等已被证明可以用来稳定皮克林乳液。这些固体颗粒由于其可再生性、可持续性，生物可降解性和生物相容性等优良特性可将其用作输送生物活性物质的载体，还可用于包覆不稳定化合物。以纳米纤维素为固体颗粒乳化剂，通过高速均质，制备柠檬醛皮克林乳液，纳米纤维素紧密排列在油水界面，提高了柠檬醛的稳定性，该方法具有制备工艺简单和成本低等优点，且乳液稳定性强，能有效缓解酸性条件下柠檬醛的降解速率。目前以纳米纤维素为固体颗粒乳化剂，制备柠檬醛皮克林乳液的相关研究尚未报道。Pickering emulsion refers to a new type of emulsion that stabilizes the emulsion system by solid particles. The stabilization mechanism is that solid particles form irreversible adsorption at the oil-water interface, thereby forming a steric hindrance effect that hinders the coalescence of droplets. At the same time, solid particles The network structure formed by mutual entanglement increases the stability of the emulsion to a certain extent. Compared with emulsions stabilized by small molecule surfactants, this system has the advantages of anti-aggregation, anti-flocculation, anti-austenification and good stability. In recent years, some food-grade solid particles such as polysaccharides and proteins have been proven to be used to stabilize Pickering emulsions. These solid particles can be used as carriers for delivering biologically active substances due to their excellent properties such as renewability, sustainability, biodegradability and biocompatibility, and can also be used to coat unstable compounds. Using nanocellulose as solid particle emulsifier, citral Pickering emulsion is prepared by high-speed homogenization. Nanocellulose is closely arranged at the oil-water interface, which improves the stability of citral. This method has the advantages of simple preparation process and low cost. Advantages, and the stability of the emulsion is strong, which can effectively alleviate the degradation rate of citral under acidic conditions. At present, there is no report on the preparation of citral Pickering emulsion using nanocellulose as solid particle emulsifier.
发明内容Contents of the invention
针对现有技术中的上述技术问题，本发明提供了一种纳米纤维素稳定的柠檬醛皮克林乳液及其制备方法，所述的这种纳米纤维素稳定的柠檬醛皮克林乳液及其制备方法要解决现有技术中的柠檬醛在酸性条件下易降解，稳定性差的技术问题。Aiming at the above-mentioned technical problems in the prior art, the invention provides a kind of citral Pickering emulsion that nanocellulose stabilizes and preparation method thereof, described this nanocellulose stabilizing citral Pickering emulsion and its The preparation method needs to solve the technical problems that the citral in the prior art is easy to degrade under acidic conditions and has poor stability.
本发明提供了一种纳米纤维素稳定的柠檬醛皮克林乳液的制备方法，包括以下步骤：The invention provides a kind of preparation method of the citral Pickering emulsion that nanocellulose stabilizes, comprises the following steps:
1）一个制备过硫酸铵水溶液的步骤；1) a step for preparing an aqueous solution of ammonium persulfate;
将过硫酸铵溶于去离子水中，搅拌直至充分溶解，形成过硫酸铵水溶液，在所述的过硫酸铵水溶液中，所述的过硫酸铵的浓度为0.5~2mol/L；Dissolving ammonium persulfate in deionized water, stirring until fully dissolved to form an aqueous ammonium persulfate solution, in the aqueous ammonium persulfate solution, the concentration of the ammonium persulfate is 0.5~2mol/L;
2）一个制备纳米纤维素悬浮液的步骤；2) a step of preparing nanocellulose suspension;
称取微晶纤维素加入到步骤1）得到的过硫酸铵水溶液中，在转速1000r/min磁力搅拌下，放入60℃水浴锅恒温搅拌4~16h，充分反应后，停止搅拌加热，得到纳米纤维素悬浮液；微晶纤维素和过硫酸铵水溶液的物料比为1~2.5克：1L；Weigh microcrystalline cellulose and add it to the ammonium persulfate aqueous solution obtained in step 1), and put it into a 60°C water bath for 4-16 hours under magnetic stirring at a speed of 1000r/min. After fully reacting, stop stirring and heating to obtain nano Cellulose suspension; the material ratio of microcrystalline cellulose and ammonium persulfate aqueous solution is 1-2.5 grams: 1L;
3）一个制备纳米纤维素粉末的步骤；3) A step of preparing nanocellulose powder;
将步骤2）得到的纳米纤维素悬浮液在10000rpm下离心，除去未反应完的过硫酸铵，离心至少两次，直至悬浮液的pH为7；将离心完后的悬浮液置于-70℃条件下预冷冻4h，然后在冷阱温度为-70℃、真空度为5Pa条件下冷冻干燥24h，得到纳米纤维素粉末；Centrifuge the nanocellulose suspension obtained in step 2) at 10,000 rpm to remove unreacted ammonium persulfate, and centrifuge at least twice until the pH of the suspension is 7; place the centrifuged suspension at -70°C Pre-freeze for 4 hours under the same conditions, and then freeze-dry for 24 hours under the condition of cold trap temperature of -70 ° C and vacuum degree of 5 Pa to obtain nanocellulose powder;
4）一个制备柠檬醛皮克林乳液的步骤；4) A step for preparing citral Pickering emulsion;
将步骤3）得到的纳米纤维素粉末溶于pH为3的柠檬酸-柠檬酸钠缓冲液中，充分搅拌后，得到纳米纤维素悬浮液，在所述的纳米纤维素悬浮液中，所述的纳米纤维素的浓度为4~10g/L，在10000~19000rpm高速均质下，在纳米纤维素悬浮液中按质量体积浓度逐滴加入柠檬醛和中链甘油三酯，所述的柠檬醛和纳米纤维素悬浮液的质量体积比为0.5~2g:100ml，所述的中链甘油三酯柠檬醛和和纳米纤维素悬浮液的质量体积比为0.5~2g:100ml，高速均质时间为2~5min，得到柠檬醛皮克林乳液。dissolving the nanocellulose powder obtained in step 3) in a citric acid-sodium citrate buffer solution with a pH of 3, and stirring thoroughly to obtain a nanocellulose suspension, in the nanocellulose suspension, the The concentration of nanocellulose is 4 ~ 10g/L, under 10000 ~ 19000rpm high-speed homogenization, citral and medium chain triglyceride are added dropwise in nanocellulose suspension according to mass volume concentration, described citral The mass volume ratio with nanocellulose suspension is 0.5 ~ 2g: 100ml, and the mass volume ratio of described medium chain triglyceride citral and nanocellulose suspension is 0.5 ~ 2g: 100ml, and the high-speed homogenization time is After 2-5 minutes, the citral Pickering emulsion was obtained.
本发明的一种柠檬醛皮克林乳液是以纳米纤维素为固体颗粒乳化剂，柠檬醛和中链甘油三酯为油相，所述乳液在40℃储藏14天后，乳液中柠檬醛的保留率可达40.48~55.31%。A kind of citral Pickering emulsion of the present invention is to use nanocellulose as solid particle emulsifier, citral and medium-chain triglyceride as oil phase, after described emulsion is stored at 40 ℃ for 14 days, the retention of citral in the emulsion The rate can reach 40.48~55.31%.
本发明是以市售微晶纤维素为原材料，经过硫酸铵氧化改性后，通过水洗得到纳米纤维素悬浮液；将此悬浮液冷冻干燥，得到纳米纤维素粉末；将纳米纤维素粉末分散于pH为3的柠檬酸-柠檬酸钠酸性缓冲溶液中，形成纳米纤维素悬浮液，随后向上述悬浮液中加入柠檬醛和中链甘油三酯，通过高速均质，得到柠檬醛皮克林乳液。The present invention uses commercially available microcrystalline cellulose as a raw material, and after being oxidized and modified by ammonium sulfate, obtains a nanocellulose suspension by washing with water; freeze-dries the suspension to obtain a nanocellulose powder; disperses the nanocellulose powder in In a citric acid-sodium citrate acidic buffer solution with a pH of 3, a nanocellulose suspension is formed, and then citral and medium-chain triglycerides are added to the suspension, and homogenized at a high speed to obtain a citral Pickering emulsion .
纤维素是自然界蕴藏丰富的可再生资源，价廉易得，对环境无污染，具有低密度、环境可持续性、可调性和低成本等性质，而且具有可再生的优势。微晶纤维素是纤维素的一种重要衍生物，是由天然纤维素经酸解或者机械处理得到，具有比表面积大、高吸水性和极好的流动性等优良特性，可作为乳化剂和抗凝结剂。但是微晶纤维素具有较强的分子间和分子内作用力，导致其难溶于水，这一性质大大限制了其乳化性能。经过硫酸铵改性得到的纳米纤维素具有较高的表面活性、较高的长宽比和高强度等优良性质，是稳定皮克林乳液理想的乳化材料。Cellulose is an abundant renewable resource in nature. It is cheap and easy to obtain, has no pollution to the environment, has the properties of low density, environmental sustainability, adjustability and low cost, and has the advantages of being renewable. Microcrystalline cellulose is an important derivative of cellulose. It is obtained from natural cellulose through acid hydrolysis or mechanical treatment. It has excellent characteristics such as large specific surface area, high water absorption and excellent fluidity. It can be used as an emulsifier and Anticoagulant. However, microcrystalline cellulose has strong intermolecular and intramolecular forces, making it difficult to dissolve in water, which greatly limits its emulsifying performance. Nanocellulose modified by ammonium sulfate has excellent properties such as high surface activity, high aspect ratio and high strength, and is an ideal emulsifying material for stabilizing Pickering emulsions.
本发明和已有技术相比，其技术进步是显著的。本发明制备的柠檬醛皮克林乳液，粒径小且粒径分布均匀，纳米纤维素紧密排列在油水界面，在油水界面发生不可逆吸附形成稳定的乳液，有效防止乳液聚合和奥氏熟化，将乳液在40℃储藏14天后，乳液中柠檬醛的保留率可达40.48~55.31%，在同样的储存条件下，空白对照组中柠檬醛保留率仅为0.95%。本发明制备的柠檬醛皮克林乳液具有纳米纤维素用量少、制备过程简单及应用成本低等特点，能有效提高酸性条件下柠檬醛的稳定性，延缓其降解。Compared with the prior art, the technical progress of the present invention is remarkable. The citral Pickering emulsion prepared by the invention has a small particle size and uniform particle size distribution, and the nanocellulose is closely arranged at the oil-water interface, and irreversible adsorption occurs at the oil-water interface to form a stable emulsion, which effectively prevents emulsion polymerization and Ostwald aging. After the emulsion was stored at 40°C for 14 days, the retention rate of citral in the emulsion could reach 40.48-55.31%. Under the same storage conditions, the retention rate of citral in the blank control group was only 0.95%. The citral Pickering emulsion prepared by the invention has the characteristics of less nano-cellulose consumption, simple preparation process and low application cost, can effectively improve the stability of citral under acidic conditions, and delay its degradation.
附图说明Description of drawings
图1是本发明实施例1所制备的柠檬醛皮克林乳液外观图。Fig. 1 is the exterior view of the citral Pickering emulsion prepared in Example 1 of the present invention.
具体实施方式Detailed ways
下面通过实施例并结合附图对本发明进一步详细描述，但并不限制本发明。The present invention will be further described in detail below by means of embodiments and in conjunction with the accompanying drawings, but the present invention is not limited.
实施例1Example 1
（1）过硫酸铵水溶液的制备(1) Preparation of ammonium persulfate aqueous solution
将过硫酸铵溶解在1L去离子水中，搅拌直至充分溶解，形成过硫酸铵水溶液，在所述的过硫酸铵水溶液中，所述的过硫酸铵的浓度为2mol/L；Dissolving ammonium persulfate in 1L deionized water, stirring until fully dissolved to form an aqueous ammonium persulfate solution, in the aqueous ammonium persulfate solution, the concentration of ammonium persulfate is 2mol/L;
（2）纳米纤维素悬浮液的制备(2) Preparation of nanocellulose suspension
将1.5克市售微晶纤维素加入到步骤（1）得到的1L过硫酸铵水溶液中，在转速1000r/min磁力搅拌下，放入60℃水浴锅恒温搅拌4h，充分反应后，停止搅拌加热，得到纳米纤维素悬浮液；Add 1.5 grams of commercially available microcrystalline cellulose to the 1L ammonium persulfate aqueous solution obtained in step (1), and put it in a 60°C water bath for 4 hours under magnetic stirring at a speed of 1000r/min. After fully reacting, stop stirring and heating , to obtain nanocellulose suspension;
（3）纳米纤维素粉末的制备(3) Preparation of nanocellulose powder
将步骤（2）得到的纳米纤维素悬浮液在10000rpm下离心，除去未反应完的过硫酸铵，离心数次，直至悬浮液的pH为7；将离心完后的悬浮液置于-70℃条件下预冷冻4h，然后在冷阱温度为-70℃、真空度为5Pa条件下冷冻干燥24h，得到纳米纤维素粉末；Centrifuge the nanocellulose suspension obtained in step (2) at 10,000 rpm to remove unreacted ammonium persulfate, and centrifuge several times until the pH of the suspension is 7; place the centrifuged suspension at -70°C Pre-freeze for 4 hours under the same conditions, and then freeze-dry for 24 hours under the condition of cold trap temperature of -70 ° C and vacuum degree of 5 Pa to obtain nanocellulose powder;
（4）柠檬醛皮克林乳液的制备(4) Preparation of Citral Pickering Emulsion
将0.6g步骤（3）得到的纳米纤维素粉末溶于100mLpH为3的柠檬酸-柠檬酸钠缓冲液中，充分搅拌后，得到纳米纤维素悬浮液。在所述的纳米纤维素悬浮液中，所述纳米纤维素浓度为6g/L。在10000rpm高速均质下，在纳米纤维素悬浮液中逐滴加入1g柠檬醛和0.5g中链甘油三酯，高速均质时间为4min，得到柠檬醛皮克林乳液。0.6 g of the nanocellulose powder obtained in step (3) was dissolved in 100 mL of citric acid-sodium citrate buffer solution with a pH of 3, and stirred thoroughly to obtain a nanocellulose suspension. In the nanocellulose suspension, the nanocellulose concentration is 6g/L. Under high-speed homogenization at 10,000 rpm, 1 g of citral and 0.5 g of medium-chain triglycerides were added dropwise to the nanocellulose suspension, and the high-speed homogenization time was 4 minutes to obtain a citral Pickering emulsion.
将上述所得的柠檬醛皮克林乳液在40 oC放置14天，通过气相色谱仪（6890GC，美国Agilent科技有限公司）对其柠檬醛保留率进行测定，为55.31%。The citral Pickering emulsion obtained above was placed at 40 o C for 14 days, and its citral retention rate was determined by gas chromatography (6890GC, Agilent Technology Co., Ltd., USA), which was 55.31%.
实施例2Example 2
（1）过硫酸铵水溶液的制备(1) Preparation of ammonium persulfate aqueous solution
将过硫酸铵溶解在1L去离子水中，搅拌直至充分溶解，形成过硫酸铵水溶液，在所述的过硫酸铵水溶液中，所述的过硫酸铵的浓度为0.5mol/L；Dissolving ammonium persulfate in 1L of deionized water, stirring until fully dissolved to form an aqueous ammonium persulfate solution, in the aqueous ammonium persulfate solution, the concentration of ammonium persulfate is 0.5mol/L;
（2）纳米纤维素悬浮液的制备(2) Preparation of nanocellulose suspension
将2克市售微晶纤维素加入到步骤（1）得到的1L过硫酸铵水溶液中，在转速1000r/min磁力搅拌下，放入60℃水浴锅恒温搅拌16h，充分反应后，停止搅拌加热，得到纳米纤维素悬浮液；Add 2 grams of commercially available microcrystalline cellulose to the 1L ammonium persulfate aqueous solution obtained in step (1), and put it in a water bath at 60°C for 16 hours under magnetic stirring at a speed of 1000 r/min. After fully reacting, stop stirring and heating , to obtain nanocellulose suspension;
（3）纳米纤维素粉末的制备(3) Preparation of nanocellulose powder
将步骤（2）得到的纳米纤维素悬浮液在10000rpm下离心，除去未反应完的过硫酸铵，离心数次，直至悬浮液的pH为7；将离心完后的悬浮液置于-70℃条件下预冷冻4h，然后在冷阱温度为-70℃、真空度为5Pa条件下冷冻干燥24h，得到纳米纤维素粉末；Centrifuge the nanocellulose suspension obtained in step (2) at 10,000 rpm to remove unreacted ammonium persulfate, and centrifuge several times until the pH of the suspension is 7; place the centrifuged suspension at -70°C Pre-freeze for 4 hours under the same conditions, and then freeze-dry for 24 hours under the condition of cold trap temperature of -70 ° C and vacuum degree of 5 Pa to obtain nanocellulose powder;
（4）柠檬醛皮克林乳液的制备(4) Preparation of Citral Pickering Emulsion
将1g步骤（3）得到的纳米纤维素粉末溶于100mLpH为3的柠檬酸-柠檬酸钠缓冲液中，充分搅拌后，得到纳米纤维素悬浮液。在所述的纳米纤维素悬浮液中，所述纳米纤维素浓度为10g/L。在16000rpm高速均质下，在纳米纤维素悬浮液中逐滴加入1.5g柠檬醛和2g中链甘油三酯，高速均质时间为3min，得到柠檬醛皮克林乳液。Dissolve 1 g of the nanocellulose powder obtained in step (3) in 100 mL of citric acid-sodium citrate buffer solution with a pH of 3, and stir thoroughly to obtain a nanocellulose suspension. In the nanocellulose suspension, the nanocellulose concentration is 10g/L. Under high-speed homogenization at 16000 rpm, 1.5 g of citral and 2 g of medium-chain triglycerides were added dropwise to the nanocellulose suspension, and the high-speed homogenization time was 3 minutes to obtain a citral Pickering emulsion.
将上述所得的柠檬醛皮克林乳液在40 oC放置14天，通过气相色谱仪（6890GC，美国Agilent科技有限公司）对其柠檬醛保留率进行测定，为40.48%。The citral Pickering emulsion obtained above was placed at 40 o C for 14 days, and the retention rate of citral was determined by gas chromatography (6890GC, Agilent Technology Co., Ltd., USA), which was 40.48%.
实施例3Example 3
（1）过硫酸铵水溶液的制备(1) Preparation of ammonium persulfate aqueous solution
将过硫酸铵溶解在1L去离子水中，搅拌直至充分溶解，形成过硫酸铵水溶液，在所述的过硫酸铵水溶液中，所述的过硫酸铵的浓度为1mol/L；Dissolving ammonium persulfate in 1L deionized water, stirring until fully dissolved to form an aqueous ammonium persulfate solution, in the aqueous ammonium persulfate solution, the concentration of ammonium persulfate is 1mol/L;
（2）纳米纤维素悬浮液的制备(2) Preparation of nanocellulose suspension
将2.5克市售微晶纤维素加入到步骤（1）得到的1L过硫酸铵水溶液中，在转速1000r/min磁力搅拌下，放入60℃水浴锅恒温搅拌8h，充分反应后，停止搅拌加热，得到纳米纤维素悬浮液；Add 2.5 grams of commercially available microcrystalline cellulose to the 1L ammonium persulfate aqueous solution obtained in step (1), and put it in a 60°C water bath for 8 hours under magnetic stirring at a speed of 1000r/min. After fully reacting, stop stirring and heating , to obtain nanocellulose suspension;
（3）纳米纤维素粉末的制备(3) Preparation of nanocellulose powder
将步骤（2）得到的纳米纤维素悬浮液在10000rpm下离心，除去未反应完的过硫酸铵，离心数次，直至悬浮液的pH为7；将离心完后的悬浮液置于-70℃条件下预冷冻4h，然后在冷阱温度为-70℃、真空度为5Pa条件下冷冻干燥24h，得到纳米纤维素粉末；Centrifuge the nanocellulose suspension obtained in step (2) at 10,000 rpm to remove unreacted ammonium persulfate, and centrifuge several times until the pH of the suspension is 7; place the centrifuged suspension at -70°C Pre-freeze for 4 hours under the same conditions, and then freeze-dry for 24 hours under the condition of cold trap temperature of -70 ° C and vacuum degree of 5 Pa to obtain nanocellulose powder;
（4）柠檬醛皮克林乳液的制备(4) Preparation of Citral Pickering Emulsion
将0.4g步骤（3）得到的纳米纤维素粉末溶于100mLpH为3的柠檬酸-柠檬酸钠缓冲液中，充分搅拌后，得到纳米纤维素悬浮液。在所述的纳米纤维素悬浮液中，所述纳米纤维素浓度为4g/L。在13000rpm高速均质下，在纳米纤维素悬浮液中逐滴加入0.5g柠檬醛和1.5g中链甘油三酯，高速均质时间为2min，得到柠檬醛皮克林乳液。0.4 g of the nanocellulose powder obtained in step (3) was dissolved in 100 mL of citric acid-sodium citrate buffer solution with a pH of 3, and stirred thoroughly to obtain a nanocellulose suspension. In the nanocellulose suspension, the nanocellulose concentration is 4g/L. Under high-speed homogenization at 13000 rpm, 0.5 g of citral and 1.5 g of medium-chain triglycerides were added dropwise to the nanocellulose suspension, and the high-speed homogenization time was 2 minutes to obtain a citral Pickering emulsion.
将上述所得的柠檬醛皮克林乳液在40 oC放置14天，通过气相色谱仪（6890GC，美国Agilent科技有限公司）对其柠檬醛保留率进行测定，为48.19%。The citral Pickering emulsion obtained above was placed at 40 o C for 14 days, and its citral retention rate was determined by gas chromatography (6890GC, Agilent Technology Co., Ltd., USA), which was 48.19%.
实施例4Example 4
（1）过硫酸铵水溶液的制备(1) Preparation of ammonium persulfate aqueous solution
将过硫酸铵溶解在1L去离子水中，搅拌直至充分溶解，形成过硫酸铵水溶液，在所述的过硫酸铵水溶液中，所述的过硫酸铵的浓度为1.5mol/L；Dissolving ammonium persulfate in 1L deionized water, stirring until fully dissolved to form an aqueous ammonium persulfate solution, in the aqueous ammonium persulfate solution, the concentration of ammonium persulfate is 1.5mol/L;
（2）纳米纤维素悬浮液的制备(2) Preparation of nanocellulose suspension
将1克市售微晶纤维素加入到步骤（1）得到的1L过硫酸铵水溶液中，在转速1000r/min磁力搅拌下，放入60℃水浴锅恒温搅拌12h，充分反应后，停止搅拌加热，得到纳米纤维素悬浮液；Add 1 gram of commercially available microcrystalline cellulose to the 1L ammonium persulfate aqueous solution obtained in step (1), and put it in a 60°C water bath for 12 hours under magnetic stirring at a speed of 1000r/min. After fully reacting, stop stirring and heating , to obtain nanocellulose suspension;
（3）纳米纤维素粉末的制备(3) Preparation of nanocellulose powder
将步骤（2）得到的纳米纤维素悬浮液在10000rpm下离心，除去未反应完的过硫酸铵，离心数次，直至悬浮液的pH为7；将离心完后的悬浮液置于-70℃条件下预冷冻4h，然后在冷阱温度为-70℃、真空度为5Pa条件下冷冻干燥24h，得到纳米纤维素粉末；Centrifuge the nanocellulose suspension obtained in step (2) at 10,000 rpm to remove unreacted ammonium persulfate, and centrifuge several times until the pH of the suspension is 7; place the centrifuged suspension at -70°C Pre-freeze for 4 hours under the same conditions, and then freeze-dry for 24 hours under the condition of cold trap temperature of -70 ° C and vacuum degree of 5 Pa to obtain nanocellulose powder;
（4）柠檬醛皮克林乳液的制备(4) Preparation of Citral Pickering Emulsion
将0.8g步骤（3）得到的纳米纤维素粉末溶于100mLpH为3的柠檬酸-柠檬酸钠缓冲液中，充分搅拌后，得到纳米纤维素悬浮液。在所述的纳米纤维素悬浮液中，所述纳米纤维素浓度为8g/L。在19000rpm高速均质下，在纳米纤维素悬浮液中逐滴加入2g柠檬醛和1g中链甘油三酯，高速均质时间为5min，得到柠檬醛皮克林乳液。0.8 g of the nanocellulose powder obtained in step (3) was dissolved in 100 mL of citric acid-sodium citrate buffer solution with a pH of 3, and stirred thoroughly to obtain a nanocellulose suspension. In the nanocellulose suspension, the nanocellulose concentration is 8g/L. Under high-speed homogenization at 19,000 rpm, 2 g of citral and 1 g of medium-chain triglycerides were added dropwise to the nanocellulose suspension, and the high-speed homogenization time was 5 minutes to obtain a citral Pickering emulsion.
将上述所得的柠檬醛皮克林乳液在40 oC放置14天，通过气相色谱仪（6890GC，美国Agilent科技有限公司）对其柠檬醛保留率进行测定，为53.10%。The citral Pickering emulsion obtained above was placed at 40 o C for 14 days, and the retention rate of citral was determined by gas chromatography (6890GC, Agilent Technology Co., Ltd., USA), which was 53.10%.
对比实施例1Comparative Example 1
将1g柠檬醛和0.5g中链甘油三酯加入到100mLpH为3的柠檬酸-柠檬酸钠缓冲液中，在10000rpm速度下剪切分散4min，即得柠檬醛水溶液（空白对照）。Add 1 g of citral and 0.5 g of medium-chain triglycerides to 100 mL of citric acid-sodium citrate buffer solution with a pH of 3, and shear and disperse at 10,000 rpm for 4 min to obtain an aqueous solution of citral (blank control).
将上述所得的空白对照在40 oC放置14天，通过气相色谱仪（6890GC，美国Agilent科技有限公司）对其柠檬醛保留率进行测定，为0.95%。The blank control obtained above was placed at 40 o C for 14 days, and its citral retention rate was determined by gas chromatography (6890GC, Agilent Technology Co., Ltd., USA), which was 0.95%.
本实施例是为了将柠檬醛皮克林乳液与空白对照进行对比，更有效的说明本发明的效果。本发明的乳液在40 oC储藏14天后，乳液中柠檬醛保留率为40.48~55.31%%，在同样的储存条件下，空白对照中柠檬醛保留率为0.95%。说明纳米纤维素颗粒大大提高了柠檬醛在酸性条件下的稳定性。This example is to compare the citral Pickering emulsion with the blank control, to more effectively illustrate the effect of the present invention. After the emulsion of the present invention is stored at 40 o C for 14 days, the retention rate of citral in the emulsion is 40.48-55.31%. Under the same storage conditions, the retention rate of citral in the blank control is 0.95%. It shows that nanocellulose particles greatly improve the stability of citral under acidic conditions.
以上所述内容仅为本发明构思下的基本说明，而依据本发明的技术方案所作的任何等效变换，均应属于本发明的保护范围。The above content is only a basic description of the concept of the present invention, and any equivalent transformation made according to the technical solution of the present invention shall fall within the scope of protection of the present invention.
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| CN113368049A (en) * | 2021-06-17 | 2021-09-10 | 江南大学 | Pickering emulsion based on fat crystal nanoparticle stability and preparation method thereof |
| CN115975229A (en) * | 2023-01-19 | 2023-04-18 | 吉林大学 | A preparation method of sodium alginate antibacterial film equipped with allicin Pickering emulsion |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113004559A (en) * | 2021-03-08 | 2021-06-22 | 四川大学 | Active gelatin-based edible film and preparation and application methods thereof |
| CN113004559B (en) * | 2021-03-08 | 2022-03-29 | 四川大学 | Active gelatin-based edible film and methods for its preparation and application |
| CN113368049A (en) * | 2021-06-17 | 2021-09-10 | 江南大学 | Pickering emulsion based on fat crystal nanoparticle stability and preparation method thereof |
| CN115975229A (en) * | 2023-01-19 | 2023-04-18 | 吉林大学 | A preparation method of sodium alginate antibacterial film equipped with allicin Pickering emulsion |
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