CN114128914A - Clathrate compound, preparation method and application thereof - Google Patents
Clathrate compound, preparation method and application thereof Download PDFInfo
- Publication number
- CN114128914A CN114128914A CN202111456806.8A CN202111456806A CN114128914A CN 114128914 A CN114128914 A CN 114128914A CN 202111456806 A CN202111456806 A CN 202111456806A CN 114128914 A CN114128914 A CN 114128914A
- Authority
- CN
- China
- Prior art keywords
- beta
- menthol
- inclusion compound
- cyclodextrin
- propylene glycol
- 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.)
- Granted
Links
Images
Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B3/00—Preparing tobacco in the factory
- A24B3/12—Steaming, curing, or flavouring tobacco
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/281—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed
- A24B15/283—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by encapsulation of the chemical substances
- A24B15/284—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by encapsulation of the chemical substances the additive being bound to a host by chemical, electrical or like forces, e.g. use of precursors, inclusion complexes
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/301—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by aromatic compounds
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/305—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances of undetermined constitution characterised by their preparation
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
The invention discloses an inclusion compound, wherein the wall material is a mixture of dioscorea opposita polysaccharide and beta-cyclodextrin, and the core material is menthol or glycerol and propylene glycol; wherein the embedding rate of the menthol is more than 70 percent; the embedding rate of the glycerol and the propylene glycol is more than 80 percent. The invention also discloses a preparation method and application of the clathrate compound.
Description
Technical Field
The invention belongs to the technical field of preparation of an inclusion compound, and particularly relates to an inclusion compound, a preparation method and application thereof.
Background
The inclusion technique refers to a biological technique of forming an inclusion compound by one molecule being occluded in a cavity structure of another molecule, and is commonly used in the field of Chinese medicinal preparations for improving the stability, the solubility and the bioavailability of medicaments, and the like. Beta-cyclodextrin (beta-CD) is a cylindrical compound formed by connecting a plurality of glucose molecules with each other by alpha-1, 4 glycosidic bonds, is a nontoxic and tasteless powdery substance, and can form an inclusion compound with organic molecules, inorganic ions, complexes and even inert gases because the outer side of a cavity contains hydrophilic groups and the inner side of the cavity contains hydrophobic groups, so that the included substance is prevented from being influenced by light, heat and oxidation. Therefore, cyclodextrin is often used as a molecular microcapsule material, and is increasingly widely applied in the fields of food, medicine and the like.
Menthol is a colorless needle crystal, slightly soluble in water, and widely used in the fields of food, cosmetics and pharmaceuticals because of its cooling activity, but menthol is very easily sublimed and unstable to light and heat. Glycerol, also known as glycerol, is a simple polyol, a colorless, sweet, non-toxic viscous liquid with high solubility and moisture retention due to its three hydroxyl groups. Propylene glycol is a viscous colorless liquid, miscible with many solvents, glycerin and propylene glycol are the main components of the electronic cigarette, glycerin is used for heating the atomizer to generate aerosol, and propylene glycol is atomized to form smoke, so as to deliver nicotine to users. Beta-cyclodextrin (beta-CD) is an ideal inclusion material, and the stability of the inclusion material can be improved after the beta-CD is adopted to include menthol or glycerol and propylene glycol, so that the inclusion compound and the application are more reported.
However, the inclusion rate of the inclusion compound obtained by taking beta-cyclodextrin as a wall material and using menthol or glycerol and propylene glycol as a core material is still relatively low, for example, the inclusion rate of menthol is difficult to exceed 50%, and the inclusion rate of glycerol and propylene glycol is difficult to exceed 70%. The present invention has been made to solve the above problems.
Disclosure of Invention
The invention provides the inclusion compound of the two alcohols, the preparation method and the application thereof based on the problems.
The preparation method of the two alcohol inclusion compounds comprises the following steps:
the technical scheme of the invention is as follows:
the invention discloses an inclusion compound, wherein the wall material of the inclusion compound is a mixture of dioscorea opposita polysaccharide and beta-cyclodextrin, and the core material of the inclusion compound is menthol or glycerol and propylene glycol; wherein the embedding rate of the menthol is more than 70 percent; the embedding rate of the glycerol and the propylene glycol is more than 80 percent.
Preferably, the entrapment rate of menthol is 70.69%; the entrapment rate of glycerol and propylene glycol was 80.58%.
Preferably, the menthol clathrate has a moisture content of 4.7 wt% and a solubility of 44.67%; the water content of the glycerin and propylene glycol inclusion compound is 5.3 wt%; the solubility was 68.14%.
Preferably, the dioscorea opposita polysaccharide is 1-10 wt% of the weight of the wall material beta-cyclodextrin and the dioscorea opposita polysaccharide.
The second aspect of the invention discloses a preparation method of the beta-cyclodextrin inclusion compound, which comprises the following steps:
dissolving Chinese yam polysaccharide and beta-cyclodextrin in a certain proportion at a certain temperature to prepare a saturated solution of the Chinese yam polysaccharide and the beta-cyclodextrin;
dissolving menthol or glycerol and propylene glycol in absolute ethyl alcohol to form a solution, then slowly dripping the solution into the saturated solution of the dioscorea opposita polysaccharide and the beta-cyclodextrin in the step I, and mixing at constant temperature;
and thirdly, cooling the mixed liquid obtained in the step II to room temperature, standing in a low-temperature environment, and then separating and drying to obtain the clathrate compound.
Preferably, the temperature of step (i) is 50-80 ℃.
Preferably, the temperature of the second step is 40-60 ℃, and the mixing time is 1-4 h; the mixing is stirring, and the stirring speed is 400-700 r/min.
Preferably, the standing temperature in the third step is 0-8 ℃, and the drying temperature is 40-60 ℃.
Preferably, the preparation method of the dioscorea opposita polysaccharide comprises the following steps: pulverizing rhizoma Dioscoreae into powder, dissolving with water, filtering, and collecting clear liquid; adding ethanol to precipitate rhizoma Dioscoreae polysaccharide, centrifuging, filtering, and freeze drying the solid phase to obtain the rhizoma Dioscoreae polysaccharide.
In a third aspect of the invention, the application of the inclusion compound in tobacco is disclosed.
The invention has the beneficial effects that:
1. the embedding rate of two alcohols of the two-alcohol inclusion compound is obviously improved. Wherein the embedding rate of the menthol can reach 70.69%; the embedding rate of the glycerol and the propylene glycol can reach 80.58 percent. The embedding rate of menthol in the prior art is difficult to exceed 50 percent, and the embedding rate of glycerin and propylene glycol is difficult to exceed 70 percent.
2. According to the preparation method of the clathrate compound, a small amount of dioscorea opposita polysaccharide is added as a wall material, so that the embedding rate of the obtained two alcohol clathrate compounds is obviously improved, and the clathrate compound is high in solubility and low in moisture content. The application of the compound in food, medicine and tobacco is expanded.
3. The preparation method is simple, and the preparation method of the dioscorea opposita polysaccharide is simple.
Drawings
FIG. 1 is an infrared spectrum of a menthol clathrate (top) and a clathrate (bottom) of glycerin and propylene glycol obtained in example 1.
FIG. 2 is a scanning electron micrograph of the menthol clathrate and the glycerin-propylene glycol clathrate obtained in example 1. The upper is wall material beta-cyclodextrin powder; the middle is menthol inclusion compound; the following is a propylene glycol and glycerol inclusion compound.
Fig. 3 shows thermogravimetric curves of the menthol inclusion compound (upper) and the glycerin and propylene glycol inclusion compound (lower) obtained in example 1.
Fig. 4 is a graph showing the release in air of the menthol inclusion compound (upper) and the inclusion compound of glycerin and propylene glycol (lower) obtained in example 1.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail by examples and experimental data below. The specific embodiments described herein are merely illustrative of the invention and do not delimit the invention.
Example 1: the preparation of two kinds of inclusion compounds comprises the following steps:
1. fully dissolving 5 wt% of dioscorea opposita polysaccharide and beta-cyclodextrin in deionized water at 70 ℃ to prepare saturated solution;
2. dissolving menthol or glycerol-propylene glycol in a small amount of absolute ethyl alcohol, slowly dripping the menthol or glycerol-propylene glycol solution into a saturated solution of beta-cyclodextrin, and stirring for 2 hours at a constant temperature of 50 ℃ and 500 r/min;
3. cooling to room temperature, standing at 4 deg.C for 24 hr, vacuum filtering, and drying at 50 deg.C to obtain two white powdered clathrates.
Example 2: embedding rate analysis of two inclusion compounds
Two kinds of clathrates (W) were obtained by collecting 1g of each of the clathrates of example 11) Adding 20mL of hot water into a small dry beaker, stirring to fully dissolve the mixture, and then sequentially adding 10mL of absolute ethyl alcohol and 10mL of absolute ethyl etherAnd 10mL of petroleum ether extracted menthol, or glycerol-propylene glycol. The extraction was repeated twice, and the combined extracts were transferred to a constant weight beaker (W)2) Evaporating the solvent to constant weight to obtain purified clathrate (W)3). According to the formula
And calculating the embedding rate. The results were: the embedding rate of menthol is 70.69%, the embedding rate of glycerol-propylene glycol is 87.58%, the embedding effect is ideal, and the embedding rate is improved by about 20% compared with that of a beta-CD single-wall material inclusion compound.
Example 3: water content analysis of two clathrates
10g (m) of the two clathrates obtained in example 1 are weighed out separately and dried in an oven at 105 ℃ for 2h, then cooled to room temperature in a drier, and the weight is m1Repeating the above operation for 1h, and weighing to m2The difference between the two is not more than 0.05 g;
the results were: the water content of the menthol inclusion compound was 4.7%, and the water content of the glycerin-propylene glycol inclusion compound was 5.3%. The water content of the two inclusion compounds is about 5%. Therefore, the product is not easy to mildew, absorb moisture and agglomerate in the storage process, and has certain storage stability.
Example 4: solubility analysis of the two Inclusions
Respectively weighing 5.0g (w) of the two inclusion compounds obtained in the example 1 into a 50mL centrifuge tube, adding a proper amount of water with the temperature of 25-30 ℃, plugging, fully shaking for dissolving for 5min, placing the centrifuge tube into a centrifuge, centrifuging the centrifuge tube at the rotating speed of 1000rmp for 10min, pouring out supernatant, adding a proper amount of water with the temperature of 25-30 ℃ into the centrifuge tube, fully shaking for 5min, centrifuging the centrifuge tube for 10min, then pouring out supernatant, repeating the step until the precipitate is not dissolved again, and washing the precipitate into a scale with known mass by using a small amount of water (w is1) Drying in boiling water, transferring into 105 deg.C oven, and drying to constant weight (w)2). The calculation formula is as follows:
the results were: the solubility of the menthol inclusion compound was 44.67%, and the solubility of the glycerin-propylene glycol inclusion compound was 68.14%. Thus, the solubility of the encapsulated menthol is improved.
Example 5: infrared analysis of two clathrates
Respectively tabletting menthol, glycerol-propylene glycol, beta-cyclodextrin and two inclusion compounds by using potassium bromide at the concentration of 500-4500 cm-1And (4) performing infrared spectrum measurement. The results are shown in FIG. 1.
As can be seen from fig. 1, the infrared spectra of the menthol- β -CD clathrate and β -CD are very similar, and the peak positions are approximately the same. beta-CD at 3402.3cm-1An absorption peak appears, which corresponds to a stretching vibration peak of-OH on a glucose ring. The stretching vibration peak of-OH in menthol-beta-CD generates red shift, and the peak position is 3390.7cm-1. Menthol is in 2922.0cm-1The absorption peak appears corresponding to-CH3And in the beta-CD and menthol beta-CD inclusion compound, the intensity of the vibration peak is obviously weakened. The bending vibration of the O-H bond of the beta-CD is also 1651.0cm-1Red shift to 1639.4cm after inclusion-1. From this, it is presumed that menthol and β -CD have undergone an inclusion reaction. Generally speaking, the infrared characteristic absorption peaks of menthol-beta-CD and beta-CD have little change, which is determined mainly by the inclusion mechanism, generally speaking, the content of guest molecules in the inclusion compound is usually not more than 25%, and the guest molecules are included in the hydrophobic cavity, so that the characteristic peaks of the guest molecules are masked by the characteristic peaks of the host molecules beta-CD and are not easily recognized. Similarly, there are similar cases in glycerol-propylene glycol, β -CD and β -CD clathrates, and the relevant parameters are shown in FIG. 1.
Example 6: surface structures of two clathrates
The surface structure of the inclusion compound was observed by a Scanning Electron Microscope (SEM). Fixing the dried inclusion compound on a metal short rod with a double-sided adhesive tape to uniformly distribute sample powder, spraying gold, and observing under the magnification of 1000 times. The results are shown in FIG. 2.
The morphological structure difference between the wall material beta-CD and the inclusion compound is observed through a scanning electron microscope, as shown in figure 2, the shapes and the sizes of the wall material and the two inclusion compounds are obviously different, wherein the surface of the wall material beta-CD is rough, the edge of the wall material beta-CD is irregular, and the surfaces of the two inclusion compounds are smooth, and the edge of the two inclusion compounds is relatively flat. The shape and size difference between the beta-cyclodextrin and the inclusion compound shows that the core material and the wall material beta-CD form a new stable inclusion state and the embedding effect is ideal.
Example 7: thermal stability analysis of the two clathrates
And (3) carrying out thermal stability analysis on the menthol, the menthol inclusion compound, the glycerol-propylene glycol inclusion compound and the mixture of the dioscorea opposita polysaccharide and the beta-cyclodextrin by adopting a comprehensive thermal analyzer. Weighing a proper amount of the inclusion compound, placing the inclusion compound in a sample cell of an instrument, wherein the atmosphere is nitrogen, and the flow is as follows: 20cm3The temperature rise rate is 10 ℃/min, and thermogravimetric analysis is carried out in the temperature range from room temperature to 800 ℃. The results are shown in FIG. 3.
The thermogravimetric analysis curve of the inclusion compound is shown in fig. 3, and as can be seen from fig. 3, the thermal weight loss process of menthol is mainly 30-160 ℃, the mass loss is close to 100%, and the weight loss process of beta-CD is mainly caused by violent volatilization and is divided into several stages: the residual moisture is volatilized at the temperature of 30-110 ℃, the mass loss is 15%, the temperature is between 110-290 ℃, the mass loss is only 1.3% in a stable area, the decomposition weight loss is 80% when the temperature is 300 ℃. The thermal weight loss process of the menthol inclusion compound has the following stages: the volatilization weight loss of free moisture and a small amount of menthol is 8 percent at the temperature of 30-90 ℃; the mass of the material is slowly reduced at 90-290 ℃, the mass loss is 5.2 percent mainly caused by slow volatilization of menthol from a beta-CD cavity, the mass loss is mainly caused by decomposition weight loss of wall materials at 300-700 ℃, the maximum decomposition temperature is 350 ℃, and the mass loss is 83 percent. It can be seen that the thermal stability of the inclusion compound is significantly improved compared to that of core material menthol. Similarly, similar behavior is observed in the inclusion system of glycerol-propylene glycol.
Example 8: release rule of two inclusion compounds in air
Respectively weighing 1.1g of the dried menthol inclusion compound, the mixture of the menthol and the dioscorea opposita polysaccharide and the beta-cyclodextrin, and the mixture of the glycerol-propylene glycol inclusion compound, the glycerol-propylene glycol, the dioscorea opposita polysaccharide and the beta-cyclodextrin, respectively, placing the mixture in an oven at 30 ℃, 50 ℃ and 70 ℃, respectively, measuring the residual mass of the sample at intervals, and observing the release rule of the inclusion compound in the air, wherein the result is shown in figure 4.
As can be seen from fig. 4, the release rates of the inclusion compound in the air are different under different temperature conditions, the release rate of the menthol inclusion compound is increased with the increase of the temperature, the release rate is gradually gentle with the increase of the time, the release rule of the glycerin-propylene glycol inclusion compound is not greatly different at 30 ℃ and 50 ℃, the release rate is obviously increased at 70 ℃, and the quality of the inclusion compound is slightly increased at 30 ℃ due to the use of the glycerin-propylene glycol with higher proportion and high hygroscopicity as the core material, probably because the substitution of the object and the water molecule in the inclusion compound occurs. Because the embedding and releasing need the participation of moisture, the moisture content in the environment has certain influence on the release of the core material in the inclusion compound.
Example 8: application of two inclusion compounds in electronic cigarette
Preparation of two clathrate tobacco liquids: respectively preparing the two inclusion compounds into electronic cigarette liquid; the control smoke solution is menthol, glycerol and propylene glycol, and the proportion of the control smoke solution is the same as that of the clathrate smoke solution. The prepared clathrate compound tobacco juice and the prepared control liquid are respectively added into the cartridges of the electronic cigarettes in the same amount, and sensory evaluation is carried out by a panel for smoking.
The evaluation finds that the sensory quality of the two clathrate compound tobacco liquids is better than that of a control tobacco liquid, the aroma of the clathrate compound tobacco liquid is better, and the specific expression is that the aroma of the clathrate compound tobacco liquid is longer and the uniformity of single-mouth smoking is better.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (10)
1. An inclusion compound is characterized in that the wall material is a mixture of dioscorea opposita polysaccharide and beta-cyclodextrin, and the core material is menthol or glycerol and propylene glycol; wherein the embedding rate of the menthol is more than 70 percent; the embedding rate of the glycerol and the propylene glycol is more than 80 percent.
2. The beta-cyclodextrin inclusion compound of claim 1, wherein the dioscorea opposita thunb polysaccharides account for 1-10 wt% of the weight of the wall materials, namely the beta-cyclodextrin and the dioscorea opposita thunb polysaccharides.
3. The beta-cyclodextrin inclusion compound according to claim 1, wherein an entrapment rate of menthol is 70.69%; the entrapment rate of glycerol and propylene glycol was 80.58%.
4. The beta-cyclodextrin inclusion compound according to claim 1, wherein the menthol inclusion compound has a moisture content of 4.7 wt% and a solubility of 44.67%; the water content of the glycerin and propylene glycol inclusion compound is 5.3 wt%; the solubility was 68.14%.
5. The method for preparing a β -cyclodextrin inclusion compound according to any one of claims 1 to 4, comprising the steps of:
dissolving Chinese yam polysaccharide and beta-cyclodextrin in a certain proportion at a certain temperature to prepare a saturated solution of the Chinese yam polysaccharide and the beta-cyclodextrin;
dissolving menthol or glycerol and propylene glycol in absolute ethyl alcohol to form a solution, then slowly dripping the solution into the saturated solution of the dioscorea opposita polysaccharide and the beta-cyclodextrin in the step I, and mixing at constant temperature;
and thirdly, cooling the mixed liquid obtained in the step II to room temperature, standing in a low-temperature environment, and then separating and drying to obtain the clathrate compound.
6. The process according to claim 5, wherein the temperature in step (i) is 50 to 80 ℃.
7. The preparation method according to claim 5, wherein the temperature of step (II) is 40-60 ℃, and the mixing time is 1-4 h; the mixing is stirring, and the stirring speed is 400-700 r/min.
8. The preparation method according to claim 5, wherein the standing temperature in the third step is 0-8 ℃ and the drying temperature is 40-60 ℃.
9. The preparation method of claim 5, wherein the dioscorea opposita polysaccharide is prepared by the following steps: pulverizing rhizoma Dioscoreae into powder, dissolving with water, filtering, and collecting clear liquid; adding ethanol to precipitate rhizoma Dioscoreae polysaccharide, centrifuging, filtering, and freeze drying the solid phase to obtain the rhizoma Dioscoreae polysaccharide.
10. Use of a clathrate according to any one of claims 1-4 in tobacco.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111456806.8A CN114128914B (en) | 2021-12-02 | 2021-12-02 | Clathrate compound, preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111456806.8A CN114128914B (en) | 2021-12-02 | 2021-12-02 | Clathrate compound, preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114128914A true CN114128914A (en) | 2022-03-04 |
| CN114128914B CN114128914B (en) | 2023-02-10 |
Family
ID=80386890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111456806.8A Active CN114128914B (en) | 2021-12-02 | 2021-12-02 | Clathrate compound, preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114128914B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115363246A (en) * | 2022-09-13 | 2022-11-22 | 吉林烟草工业有限责任公司 | Atomizer in heat-not-burn cigarettes and its preparation method and application |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5874418A (en) * | 1997-05-05 | 1999-02-23 | Cydex, Inc. | Sulfoalkyl ether cyclodextrin based solid pharmaceutical formulations and their use |
| CN102140387A (en) * | 2011-01-20 | 2011-08-03 | 深圳市如烟生物科技有限公司 | Method for preparing microcapsule essence for cigarette |
| CN107365628A (en) * | 2017-06-29 | 2017-11-21 | 云南中烟新材料科技有限公司 | A kind of cigarette fragrance sustained release agent and its preparation method and application |
| CN108618190A (en) * | 2018-08-15 | 2018-10-09 | 云南中烟工业有限责任公司 | A kind of tobacco juice for electronic smoke |
| CN108925999A (en) * | 2018-08-08 | 2018-12-04 | 河南城建学院 | The preparation method of RHIIZOMA DIOSCOREAE from Henan of China active peptide dry powder, RHIIZOMA DIOSCOREAE from Henan of China activity peptide health product and its microcapsules |
| CN112705131A (en) * | 2020-12-29 | 2021-04-27 | 广西中烟工业有限责任公司 | Preparation method of eutectic solvent/hydroxypropyl-beta-cyclodextrin menthol microcapsule |
-
2021
- 2021-12-02 CN CN202111456806.8A patent/CN114128914B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5874418A (en) * | 1997-05-05 | 1999-02-23 | Cydex, Inc. | Sulfoalkyl ether cyclodextrin based solid pharmaceutical formulations and their use |
| CN102140387A (en) * | 2011-01-20 | 2011-08-03 | 深圳市如烟生物科技有限公司 | Method for preparing microcapsule essence for cigarette |
| CN107365628A (en) * | 2017-06-29 | 2017-11-21 | 云南中烟新材料科技有限公司 | A kind of cigarette fragrance sustained release agent and its preparation method and application |
| CN108925999A (en) * | 2018-08-08 | 2018-12-04 | 河南城建学院 | The preparation method of RHIIZOMA DIOSCOREAE from Henan of China active peptide dry powder, RHIIZOMA DIOSCOREAE from Henan of China activity peptide health product and its microcapsules |
| CN108618190A (en) * | 2018-08-15 | 2018-10-09 | 云南中烟工业有限责任公司 | A kind of tobacco juice for electronic smoke |
| CN112705131A (en) * | 2020-12-29 | 2021-04-27 | 广西中烟工业有限责任公司 | Preparation method of eutectic solvent/hydroxypropyl-beta-cyclodextrin menthol microcapsule |
Non-Patent Citations (1)
| Title |
|---|
| 王金鹏等: "制备及干燥工艺对环糊精薄荷醇包合物的影响", 《食品工业科技》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115363246A (en) * | 2022-09-13 | 2022-11-22 | 吉林烟草工业有限责任公司 | Atomizer in heat-not-burn cigarettes and its preparation method and application |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114128914B (en) | 2023-02-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wadhwa et al. | Essential oil–cyclodextrin complexes: An updated review | |
| El Achkar et al. | Cyclodextrins: from solute to solvent | |
| Hadian et al. | Preparation and characterization of nanoparticle β-cyclodextrin: Geraniol inclusion complexes | |
| Haiyee et al. | Characterization of cyclodextrin complexes with turmeric oleoresin | |
| WO2006137959A1 (en) | Cyclodextrin inclusion complexes and methods of preparing same | |
| Wang et al. | Complexation and molecular microcapsules of Litsea cubeba essential oil with β-cyclodextrin and its derivatives | |
| CN114128914B (en) | Clathrate compound, preparation method and application thereof | |
| EP4144231A1 (en) | Nicotine supply oral pouch product and production method therefor | |
| US3047431A (en) | Smoking composition | |
| CN104194931A (en) | Menthol-loaded porous polymer microsphere tobacco spice slow-release material and preparation method thereof | |
| CN103320229A (en) | Preparation method of rose essence nanocapsules | |
| CN112705131B (en) | Preparation method of eutectic solvent/hydroxypropyl-beta-cyclodextrin menthol microcapsule | |
| CN108085352A (en) | A kind of method of two enzymes method control cyclodextrin inclusion compound sustained release | |
| CN113018457B (en) | Cyclodextrin inclusion compound and preparation method thereof | |
| CN102578702A (en) | Hydroxypropyl-beta-cyclodextrin clathrate preparation method of cream for cigarette | |
| CN113040419A (en) | Electronic cigarette liquid capable of stably releasing nicotine | |
| CN105194686A (en) | Inclusion compound containing camphor oil and preparation method thereof | |
| CN105267978A (en) | Preparation method and application of cyclodextrin inclusion compound containing Blumea balsamifera extract | |
| CN106177988B (en) | A kind of preparation method of isoquercitin inclusion compound | |
| CN113907409A (en) | A kind of moisture-proof moisturizing agent for preventing tobacco sheet from absorbing moisture and preparation method thereof | |
| CN115363246A (en) | Atomizer in heat-not-burn cigarettes and its preparation method and application | |
| Pérez-Martínez et al. | 2, 4-D-α-Cyclodextrin Complexes: Preparation and characterization by thermal analysis | |
| Oliveira et al. | Encapsulation of volatile oils with antimicrobial activity in chitosan-βCD molecular inclusion complexes by spray drying | |
| Pérez-Martínez et al. | 2, 4-dichlorophenoxyacetic acid/partially methylated-β-cyclodextrin inclusion complexes | |
| Cho et al. | Encapsulation of flavors by molecular inclusion using $\beta $-Cyclodextrin: comparison with spray-drying process using carbohydrate-based wall materials |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |