CN102352557A - Preparation method and application of cyclodextrin graft-immobilized cellulose acetate - Google Patents
Preparation method and application of cyclodextrin graft-immobilized cellulose acetate Download PDFInfo
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- CN102352557A CN102352557A CN2011102373205A CN201110237320A CN102352557A CN 102352557 A CN102352557 A CN 102352557A CN 2011102373205 A CN2011102373205 A CN 2011102373205A CN 201110237320 A CN201110237320 A CN 201110237320A CN 102352557 A CN102352557 A CN 102352557A
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Abstract
The invention relates to a preparation method of cyclodextrin graft-immobilized cellulose acetate. The preparation method comprises the following steps: a. preparation of cellulose acetate modification finishing liquid; b. leaching and rolling process; c. baking process; d. water washing for removing impurities; and e. drying. The cyclodextrin graft-immobilized cellulose acetate prepared by the method provided by the invention can be applied to cigarette filter tip materials and can be used for reducing harmful components such as benzene and benzene-series compounds, volatile phenol compounds, polycyclic arenes, heavy metals and the like in main smoke of the cigarette, or improving the dyeing stability and dyeability of cigarette cellulose acetate tows, or prolonging the fragrance of the cigarette filter tip and the sustained release of the fragrance. The preparation method has the advantages that: citric acid is used as a crosslinking agent, cyclodextrin is firstly grafted to cellulose acetate, and used citric acid is a food additive and has better safety; and for cigarette manufactures, by adoption of the modified cellulose acetate filter tip with a selective harm reducing effect, expensive composite shaping machine is not purchased, the cost is lowered and significant economic benefit is achieved.
Description
Technical field
The invention belongs to cellulose acetate material modification method for preparing and Application Areas; Relate to prepare the synthetic process of novel cyclodextrin graft modification acetate silk specifically, and use it for application technology at aspects such as cigarette mainstream flue gas harm reduction, tow dyeing and tow lastings.
Background technology
(Cyclodextrin is to act on one group of cyclic oligosaccharide that combines with α-1,4 glycosidic bond (Villiers found in 1891) that starch produces through biochemical action by cyclodextrin glycosyltransferase (CGT) CD) to cyclodextrin.Modal have α-CD, β-CD, a γ-CD, they be by 6,7 or 8 glucose units with α-1,4 glycosidic bond be combined into, void diameter is respectively 0.57,0.78 and 0.95nm.What cyclodextrin molecular was shaped as " in hydrophobic, outer hydrophilic " slightly is the nanoscale cavity structure of boring tubular.This just special construction; Make that cyclodextrin can different " object " compound of envelope as " host "; Form the supermolecule inclusion complex (Inclusion Complex) of special construction, obtained extensive use in fields such as Chemical Decomposition and analysis, environmental protection, edible cosmetic product processing and medicine control releases
[1 ~ 4]Simultaneously, the result of study of all toxicological evaluations shows, because cyclodextrin compounds can not be by gastrointestinal absorption, so in fact cyclodextrin compound does not exist toxicity to human body
[5]This makes cyclodextrin have wide prospect more in the application of food, cigarette, medicine.
Natural polymer is the ideal carrier of cyclodextrin, and cyclodextrin and natural polymer bonding prepare cyclodextrin, has given natural polymer new performance and function, has become the important branch of cyclodextrin producing high-molecular.
As far back as 1996, German Wacker company developed the cyclodextrine derivatives with reactivity---a chlorotriazine cyclodextrin (MCT-CD).This activity cyclodextrin can utilize the envelope effect of cyclodextrin through contaminating and knot dyeing technology be fixed to cellulose surface with cyclodextrin, thus can process have fragrance, drug effect, preserve moisture, the corrosion-resistant functional fibre material
[6 ~ 7]N.A. people such as Ibrahim
[8]Utilize MCT-β-CD to put cotton fiber in order, after this, people such as W. M. Raslan
[9]Success is immobilized on cellulose acetate with MCT-β-CD; And inquired into the research of aspects such as this modification acetate silk stainability ability; Two researchs are all found; Compare with undressed fiber, the immobilized fiber of cyclodextrin the colourity intensity of dyeing and painted after aspects such as stability all demonstrate extremely significant superior function.In addition, through chemical cross-linking agent (such as epoxy chloropropionate alcohol, citric acid, isocyanates etc.) that the immobilized application study on cellulose of cyclodextrin grafting is also a lot.Hunan University just discloses the preparation method of a kind of cellulose acetate and cyclodextrin graft copolymer and the patent that slowly-releasing is used thereof as far back as 2005
[10]This patent of invention utilizes isocyanate crosslinking that cyclodextrin is grafted on the cellulose acetate; Be used for the envelope perfume ingredient, thereby reach slow release fragrance, keep the purpose of lasting fragrance; But its used isocyanate crosslinking has certain toxicity, makes it receive certain limitation in the application aspect food, medicine and the cigarette.L. Ducoroy etc.
[11]The people utilizes citric acid to be crosslinking agent, and cyclodextrin is grafted on the removal that is used for the water heavy metal cation on the polyester fiber (PET), and result of study shows that every this kind of gram modified fibre can adsorb Pb
2+, Ni
2+And Cd
2+Amount be 0.3mmol.People such as Sabrine Alila
[12]Utilize N, N-N,N'-carbonyldiimidazole (CDI) is a crosslinking agent, ring is stuck with paste be grafted to the removal research that is applied to organic pollution in the water on the cellulose fibre, and the result shows that the cellulose after the modification is to organic pollution and the agricultural residual high absorption removal effect that has of herbicide.
The enhancing of public's health environment-friendly consciousness and to the raising of cigarette recognizing dangers; Cigarette harm reduction technology has been proposed new challenge; For production of cigarettes producer, adopt modification acetate fiber filter tip with selective harm reduction effect, do not need to purchase in addition expensive composite molding machine; Cost than composite tip stick is much lower, has remarkable economic efficiency; Aspect the dyeing of acetate tow, the at present external application of chromatic colour diacetate fiber cigarette filter tip, and the domestic product that does not still have this type of; In addition aspect the application study of fragrant cigarette filter tip; Domestic Changbai Mountain brand cigarette is through adding fragrant line in cigarette filter tip; Thereby improve the fragrance of cigarette, but this kind method need be added complicated composite tip stick production technology in the cigarette filter tip forming process, cost is higher relatively.In sum, the acetate silk after the cyclodextrin grafting is owing to have good functional characteristic, in the cigarette selective harm reduction and improve its stainability and can have the potential advantage developed with long lasting quality.
Summary of the invention
The object of the invention just is being based on above-mentioned prior art situation and the method and the application thereof of the immobilized cellulose acetate of a kind of cyclodextrin grafting developed.
The objective of the invention is to realize through following technical scheme: the preparation method of the immobilized cellulose acetate of cyclodextrin grafting of the present invention comprises following processing step:
The preparation of a, cellulose acetate modification dressing liquid;
B, pad technology: adopt impregnation technology that above-mentioned dressing liquid is evenly coated on the cellulose acetate, and utilize pressing and rolling process control liquid holdup;
C, bake and bank up with earth technology: adopt and bake and bank up with earth technology twice, at first, bake and bank up with earth reaction 1-5 minute at 150-180 ℃ of high temperature again 80-110 ℃ of low temperature preliminary drying 2-10 minute;
D, washing removal of impurities: will pass through and bake and bank up with earth back cellulose acetate water and embathe for several times, to remove unreacted matters and by-product impurities;
E, drying: can dry naturally or flash baking under 40-80 ℃ of condition;
In the present invention, cellulose acetate modification dressing liquid can be prepared from following two kinds of methods:
First method is soluble in water formulated by cyclodextrin, citric acid, catalyst, polyethylene glycol, and each component ratio is: cyclodextrin 50-200g, citric acid 50-200g; Catalyst 10-100g; Polyethylene glycol 10-100mL adds 1 liter in water, and stirring and dissolving is formulated.
Second method is formulated by cyclodextrin, citric acid, catalyst and water, and concrete grammar is: earlier with 50-200g, and citric acid 50-200g; Catalyst 10-100g adds 1 liter in water, under 100-150 ℃ of condition fully stirring reaction 0.5-3 hour; Be taken out to the solution cooling, then mixture placed ethanolic solution, backflow 5-10 hour; To remove remaining citric acid, catalyst and by-product impurities, white solid product is dissolved with low amounts of water the most at last, makes it deposition with acetone; Obtain cyclodextrin and citric acid polymer, this polymer 50-200g, catalyst 10-100g are dissolved in are cellulose acetate modification dressing liquid in 1 premium on currency again.
Catalyst according to the invention can be any one the perhaps several kinds of mixing in sodium dihydrogen phosphate, sodium hydrogen phosphate, inferior sodium phosphate, the sodium hypophosphite.
In padding technology, should control the dressing liquid pick-up between 70-110%.
Employed cyclodextrin is any one or several kinds of combinations in the derivative of alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin, HP-, methyl-beta-schardinger dextrin-or other cyclodextrin.
Employed cellulose acetate is a cellulose acetate or cellulose diacetate.
The immobilized cellulose acetate of cyclodextrin grafting that utilizes the inventive method to prepare can be applicable on the cigarette filter material, can reduce harmful components such as benzene and benzene series thing, Volatile Phenols compounds, polycyclic aromatic hydrocarbon and heavy metal in the cigarette mainstream flue gas; Or the dye stability and the stainability of raising cigarette acetate silk, or the slowly-releasing of prolongation cigarette filter lasting and fragrance.
The present invention compared with prior art has following characteristics and advantage:
(1) the present invention adopts citric acid as crosslinking agent, first cyclodextrin is grafted on the cellulose acetate;
(2) in the present invention, the citric acid of employing adopts the isocyanate crosslinking method to have better security for food additives commonly used, meets the food safety and sanitation requirement;
(3) for production of cigarettes producer, adopt modification acetate fiber filter tip with selective harm reduction effect, do not need to purchase expensive composite molding machine in addition, much lower than the cost of composite tip stick, have remarkable economic efficiency;
Description of drawings
The comparison of Fig. 1 cyclodextrin grafting cellulose acetate filter tip and common acetate fiber filter tip main volatile phenolic compound burst size in cigarette mainstream flue gas.
600 times of electron microscope pictures of the unprocessed acetate silk of Fig. 2
600 times of electron microscope pictures of Fig. 3 cyclodextrin grafting acetate silk
The specific embodiment
The present invention does below in conjunction with embodiment and further describes, but is not restriction the present invention.
Preparation method's instance 1:
Take by weighing beta-schardinger dextrin-100g, citric acid 100g, sodium dihydrogen phosphate 40g; Polyethylene glycol 20mL dissolves preparation grafted by beta cyclodextrin cellulose acetate dressing liquid in 1 premium on currency, get the 10g cellulose diacetate, adopts two to soak two roll process; The control pick-up is 80%, and preliminary drying 5 minutes under 90 ℃ of conditions is baked and banked up with earth reaction 2 minutes under 160 ℃ of conditions then; Water embathes 5 times, dries naturally.The grafted by beta cyclodextrin rate reaches 15% ~ 25% in the product.
Preparation method's instance 2:
Weighing beta-schardinger dextrin-100g, citric acid 100g, catalyst (sodium hydrogen phosphate) 40g; 1 liter in water is in large beaker, and abundant stirring reaction 2 hours under 120 ℃ of conditions is taken out to the solution cooling; Then mixture is placed ethanolic solution, refluxed 6 hours, to remove remaining citric acid, catalyst and by-product impurities; White solid product is dissolved with low amounts of water the most at last, makes it deposition with acetone, obtains cyclodextrin and citric acid polymer.This polymer of weighing 100g, sodium dihydrogen phosphate 40g are dissolved in 1 premium on currency and are mixed with dressing liquid, get the 10g cellulose diacetate, adopt two to soak two roll process; The control pick-up is 80%, and preliminary drying 5 minutes under 90 ℃ of conditions is baked and banked up with earth reaction 2 minutes under 160 ℃ of conditions then; Water embathes 5 times, dries naturally.The grafted by beta cyclodextrin rate reaches 20%-30% in the product.
Preparation method's instance 3:
Take by weighing HP-200g, citric acid 200g, inferior sodium phosphate 100g; Polyethylene glycol 40mL dissolves preparation HP-grafting cellulose acetate dressing liquid in 1 premium on currency, get the 10g cellulose diacetate, adopts two to soak two roll process; The control pick-up is 90%, and preliminary drying 7 minutes under 80 ℃ of conditions is baked and banked up with earth reaction 3 minutes under 170 ℃ of conditions then; Water embathes 5 times, dries naturally.The HP-percent grafting reaches 25%-40% in the product.
Application example 4:
The dressing liquid of resultant cyclodextrin in the instance 2 and citric acid polymer is added in the diacetate fiber cigarette filter rod; Addition 200 μ L; With filter stick preliminary drying 5 minutes under 90 ℃ of conditions, bake and bank up with earth reaction 2 minutes under 160 ℃ of conditions then, after the cooling cigarette filter rod was placed under the constant-temperature constant-humidity environment balance 24 hours; Cigarette filter rod after the balance is inserted in the cigarette filter; Carry out the detection of Volatile Phenols compounds in the cigarette mainstream flue gas, result of the test is as shown in Figure 1, and is visible from figure; Adopt cyclodextrin grafting acetate fiber filter tip to reduce main volatile phenolic compounds such as hydroquinones, resorcinol, catechol, phenol, M-and P-cresols, orthoresol in the cigarette mainstream flue gas by effective as selective, wherein the selectivity of phenol lowers efficiency and reaches 68%.
Application example 5:
Take by weighing beta-schardinger dextrin-120g, citric acid 120g, each 25g of sodium hypophosphite and sodium hydrogen phosphate; Polyethylene glycol 40mL dissolves preparation grafted by beta cyclodextrin cellulose acetate dressing liquid in 1 premium on currency, get 10g diacetate fiber fibroin, adopts two to soak two roll process; The control pick-up is 100%, and preliminary drying 5 minutes under 80 ℃ of conditions is baked and banked up with earth reaction 2 minutes under 160 ℃ of conditions then; Water embathes 5 times, dries naturally.The grafted by beta cyclodextrin rate reaches 21% in the product.Resulting grafted by beta cyclodextrin acetate fiber fibroin photo such as Fig. 3 under 600 power microscopes; Compare with undressed acetate fiber fibroin (like Fig. 2); The colloidal substance material is obviously adhered on grafted by beta cyclodextrin acetate fiber fibroin surface; Simultaneously a small amount of this modification cellulose acetate is immersed in the NaOH alkalescence aqueous solution of phenolphthalein, can finds that red material rapidly disappears, this be since cellulose acetate attend the cyclodextrin of institute's grafting can envelope phenolphthalein molecule; Thereby make phenolphthalein colour developing ability inactivation, explain that thus the colloid graft on the acetate silk really is cyclodextrin.
Application example 6:
The cyclodextrin grafting cellulose acetate material of preparation in the instance 5 is immersed in the ethanolic solution that contains bata-phenethyl alcohol; Sealing back vibration 10 hours; Impel cyclodextrin and bata-phenethyl alcohol on the cellulose acetate to form microcapsules envelope product, after fume hood dries, under the constant temperature and humidity condition, preserved 5 days; Carry out sensory evaluation to it every day, according to same operation undressed common cellulose acetate handled as control sample simultaneously.The result finds that cyclodextrin grafting cellulose acetate material kept fragrance good at 5 days, has the ability that the gentle slow release of good lasting is put fragrance with comparing with reference to sample.
List of references
[1] zjelti,?J.:?Introduction?and?general?overview?of?cyclodextrin?chemistry.?Chem.?Rev.?1998,?98:?1743。
[2] McCray,?J.E.,?Boving,?T.B.,?Brusseau,?M.L.:?Cyclodextrinenhanced?solubilization?of?organic?compounds?with?implications?for?aquifer?remediation.?Ground?Water?Monit.?R.?2000,?21:?58~66。
[3] Phan,?T.N.T.,?Bacquet,?M.,?Morcellet,?M.:?The?removal?of?organic?pollutants?from?water?using?new?silica-supported?bcyclodextrin?derivatives.?React.?Funct.?Polym.?2002,?52:?117~125.。
[4] Veignie,?E.,?Rafin,?C.,?Landy,?D.,?Fourmentin,?S.,?Surpateanu,?G.:Fenton?degradation?assisted?by?cyclodextrins?of?a?high?molecular?weight?polycyclic?aromatic?hydrocarbon?benzo[a]pyrene.?J.Hazard.?Mater.?2009,?168:?1296~1301。
[5] Irie?T,?Uekama?K.?Pharmaceutical?applications?of?cyclodextrins.?III.?Toxicological?issues?and?safety?evaluation.?J?Pharm?Sci?1997,?86:147~62。
[6] Reuscher?H．，Hirsenkorn?R．Inclusion?phenomena?and?molecular?recognition?in?chemistry[J]．?Chem．Res．，1996，25(1~3)：191。
[7] N.?KISTAMAH,?C.?M.?CARR.?Surface?chemical?analysis?of?tencel?and?cotton?treated?with?a?monochlorotriazinyl?(MCT)?β-cyclodextrin?derivative.?J?MATER?SCI.?2006,?41: 2195~2200。
[8] N.A.?Ibrahim?,?W.R.?E-Zairy?,?B.M.?Eid.?Novel?approach?for?improving?disperse?dyeing?and?UV-protective?function?of?cotton-containing?fabrics?using?MCT-β-CD.?Carbohydrate?Polymers,?2010,?79:?839~846。
[9] W.?M.?Raslan,?A.?T.?El-Aref,?A.?Bendak.?Modification?of?Cellulose?Acetate?Fabric?with?Cyclodextrin?to?Improve?Its?Dyeability.?Journal?ofAppliedPolymer?Science,?2009，112:?3192~3198。
[10] CN?200510032452.9。
[11] L.?Ducoroy,?B.?Martel,?B.?Bacquet.?Ion?exchange?textiles?from?the?finishing?of?PET?fabrics?with?cyclodextrins?and?citric?acid?for?the?sorption?of?metallic?cations?in?water.?J?Incl?Phenom?Macrocycl?Chem.?2007,?57:271~277。
[12] Sabrine?Alila,?Sami?Boufi.?Removal?of?organic?pollutants?from?water?by?modified?cellulose?fibres.?Industrial?Crops?and?Products.?2009,?30:?93~104。
Claims (9)
1. the preparation method of the immobilized cellulose acetate of cyclodextrin grafting is characterized in that: comprise following processing step:
The preparation of cellulose acetate modification dressing liquid;
Pad technology: adopt impregnation technology that above-mentioned dressing liquid is evenly coated on the cellulose acetate, and utilize pressing and rolling process control liquid holdup;
Bake and bank up with earth technology: adopt and bake and bank up with earth technology twice,, bake and bank up with earth reaction 1-5 minute at 150-180 ℃ of high temperature at first 80-110 ℃ of low temperature preliminary drying 2-10 minute;
Washing removal of impurities: will pass through and bake and bank up with earth back cellulose acetate water and embathe for several times, to remove unreacted matters and by-product impurities;
Dry: as can to dry naturally or flash baking under 40-80 ℃ of condition.
2. the preparation method of the immobilized cellulose acetate of cyclodextrin grafting according to claim 1; It is characterized in that: cellulose acetate modification dressing liquid is prepared from following two kinds of methods: first method is soluble in water formulated by cyclodextrin, citric acid, catalyst, polyethylene glycol, and second method is formulated by cyclodextrin, citric acid, catalyst and water.
3. the preparation method of the immobilized cellulose acetate of cyclodextrin grafting according to claim 2; It is characterized in that: first kind of cellulose acetate modification dressing liquid compound method is to take by weighing cyclodextrin 50-200g; Citric acid 50-200g, catalyst 10-100g, polyethylene glycol 10-100mL; Add 1 liter in water, stirring and dissolving is formulated.
4. the preparation method of the immobilized cellulose acetate of cyclodextrin grafting according to claim 2 is characterized in that: second kind of cellulose acetate modification dressing liquid compound method is: earlier with 50-200g, and citric acid 50-200g; Catalyst 10-100g adds 1 liter in water, under 100-150 ℃ of condition fully stirring reaction 0.5-3 hour; Be taken out to the solution cooling; Then mixture is placed ethanolic solution, backflow 5-10 hour, to remove remaining citric acid, catalyst and by-product impurities; White solid product is dissolved with low amounts of water the most at last; Make it deposition with acetone, obtain cyclodextrin and citric acid polymer, this polymer 50-200g, catalyst 10-100g are dissolved in are cellulose acetate modification dressing liquid in 1 premium on currency again.
5. according to the preparation method of claim 2 or the immobilized cellulose acetate of 3 or 4 described cyclodextrin grafting, it is characterized in that: said catalyst is any one the perhaps several kinds of mixing in sodium dihydrogen phosphate, sodium hydrogen phosphate, inferior sodium phosphate, the sodium hypophosphite.
6. the preparation method of the immobilized cellulose acetate of cyclodextrin grafting according to claim 1 is characterized in that: in padding technology, should control the dressing liquid pick-up between 70-110%.
7. the preparation method of the immobilized cellulose acetate of cyclodextrin grafting according to claim 1 is characterized in that: employed cyclodextrin is any one or several kinds of combinations in the derivative of alpha-cyclodextrin, beta-schardinger dextrin-, gamma-cyclodextrin, HP-, methyl-beta-schardinger dextrin-or other cyclodextrin.
8. the preparation method of the immobilized cellulose acetate of cyclodextrin grafting according to claim 1 is characterized in that: employed cellulose acetate is a cellulose acetate or cellulose diacetate.
9. the application of the immobilized cellulose acetate of cyclodextrin grafting on the cigarette filter material of the said method preparation of claim 1 can be used for reducing harmful components such as benzene and benzene series thing, Volatile Phenols compounds, polycyclic aromatic hydrocarbon and heavy metal in the cigarette mainstream flue gas; Or the dye stability and the stainability of raising cigarette acetate silk, or the slowly-releasing of prolongation cigarette filter lasting and fragrance.
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| CN102634992A (en) * | 2012-05-02 | 2012-08-15 | 江南大学 | Method for dyeing cyclodextrin cross-linked modified polyester, cotton and blended fabric by cationic dyes |
| CN102805425A (en) * | 2012-08-30 | 2012-12-05 | 江苏中烟工业有限责任公司 | Application of beta-carotene/beta-cyclodextrin inclusion compounds to release quantity reduction of phenolic compounds in cigarette smoke gas |
| CN103422339A (en) * | 2013-08-23 | 2013-12-04 | 华南理工大学 | Method for preparing antibacterial functional cellulosic fibers |
| CN104473324A (en) * | 2014-10-22 | 2015-04-01 | 浙江中烟工业有限责任公司 | Application of cyclodextrin polymer for selectively reducing phenol content in cigarette smoke |
| CN105088867A (en) * | 2015-08-04 | 2015-11-25 | 浙江中烟工业有限责任公司 | Nanofiber composite paper used for reducing phenol content in smoke and preparation method and application of nanofiber composite paper |
| CN105155027A (en) * | 2015-08-04 | 2015-12-16 | 浙江中烟工业有限责任公司 | Nanometer fiber composite filament bundle capable of reducing content of phenol in smoke, and preparation method and application of nanometer fiber composite filament bundle |
| CN105622962A (en) * | 2016-03-16 | 2016-06-01 | 江南大学 | Preparation method of composite cyclodextrin hydrogel |
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| CN102634992A (en) * | 2012-05-02 | 2012-08-15 | 江南大学 | Method for dyeing cyclodextrin cross-linked modified polyester, cotton and blended fabric by cationic dyes |
| CN102805425A (en) * | 2012-08-30 | 2012-12-05 | 江苏中烟工业有限责任公司 | Application of beta-carotene/beta-cyclodextrin inclusion compounds to release quantity reduction of phenolic compounds in cigarette smoke gas |
| CN103422339B (en) * | 2013-08-23 | 2015-09-02 | 华南理工大学 | A kind of preparation method of functional antibacterial fibre cellulose fiber |
| CN103422339A (en) * | 2013-08-23 | 2013-12-04 | 华南理工大学 | Method for preparing antibacterial functional cellulosic fibers |
| CN104473324B (en) * | 2014-10-22 | 2017-01-11 | 浙江中烟工业有限责任公司 | Application of cyclodextrin polymer for selectively reducing phenol content in cigarette smoke |
| CN104473324A (en) * | 2014-10-22 | 2015-04-01 | 浙江中烟工业有限责任公司 | Application of cyclodextrin polymer for selectively reducing phenol content in cigarette smoke |
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| CN107447517B (en) * | 2017-07-25 | 2020-05-26 | 西安工程大学 | Preparation method of polyester non-woven fabric capable of rapidly adsorbing heavy metal ions |
| CN108671773A (en) * | 2018-06-07 | 2018-10-19 | 中国药科大学 | A kind of modification cellulose acetate film, preparation method and application for chiral resolution |
| CN108671773B (en) * | 2018-06-07 | 2020-07-14 | 中国药科大学 | Modified cellulose acetate membrane for chiral resolution, preparation method and application |
| CN110564515A (en) * | 2019-08-20 | 2019-12-13 | 广东工业大学 | Essence microcapsule grafted with organic silicon quaternary ammonium salt and preparation method and application thereof |
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