CN113831424A - Preparation method of cydiodine - Google Patents
Preparation method of cydiodine Download PDFInfo
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- CN113831424A CN113831424A CN202111285826.3A CN202111285826A CN113831424A CN 113831424 A CN113831424 A CN 113831424A CN 202111285826 A CN202111285826 A CN 202111285826A CN 113831424 A CN113831424 A CN 113831424A
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- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
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Abstract
The invention discloses a preparation method of cydiodine, which comprises povidone iodine with mass m and beta-cyclodextrin with mass n, wherein iodine molecules in the povidone iodine have the mass
Said
=
Description
Technical Field
The invention relates to the technical field of cydiodine preparation, in particular to a preparation method of cydiodine, which has high economic benefit and safer preparation and does not contain potassium ions.
Background
Cydiodine is a common disinfectant, and is commonly used in clinical practice for disinfecting buccal tablets, mucous membranes and the like. Wherein, the most typical product in China is 'Huasu tablets' for treating oral infectious inflammation; in addition, the ministry of agriculture in 2019 of China approves three new veterinary drugs of 'cydiodine powder' disinfectant. The novel veterinary drug can be used for disinfecting clinical chicken houses, pigsties and various breeding environments, and has large market demand. The history of cydiodine development, which first appeared in japan, in 1976, 3 cydiodine production processes were approved in japan. The first patent right of the preparation process of cydiodine is not obtained until 1991 in the republic of Chinese people, and China starts late in the research, development and production of cydiodine.
Although the cydiodine preparation process has been developed for a long time, there are still many problems in the development and production of the existing cydiodine preparation process. For example, cydiodine is a β -cyclodextrin coated preparation of iodine molecules, and the product is obtained by coating iodine in a monomolecular state with β -cyclodextrin, and thus the product is also called "iodine molecule capsule". Although the existing preparation methods of cydiodine at home and abroad have many processes, the existing preparation methods use potassium iodide as a cosolvent, iodine is dissolved in an ethanol solution, and then the dissolved iodine is mixed with a beta-cyclodextrin solution to obtain the cydiodine. The above method for preparing cydiodine has the following technical problems.
Firstly, potassium iodide is used as a cosolvent, so that the obtained cydiodine product contains a large amount of potassium ions and iodide ions, and the potassium ions and the iodide ions cannot be used for sterilization and disinfection, which is equivalent to increase of impurities. Secondly, the potassium iodide is high in price, and the potassium iodide is used as a cosolvent, so that the manufacturing cost of the cydiodine is obviously increased; a large amount of potassium ions are introduced into the finally obtained cydiodine, and the potassium ions influence the heart rate of animals and have potential hazard to human beings or animals. Secondly, in the existing preparation process of cydiodine, iodine molecules are dissolved by ethanol or ethanol solution, and then coating is carried out, wherein ethanol is volatile, flammable and explosive, and fire or explosion is very easy to occur in the operation process; after the iodine is dissolved in the ethanol, the iodine has stronger corrosion effect, has stronger harmfulness to facilities, equipment, personnel and the like for preparing the cydiodine, and has higher requirements on the production process. Thirdly, the existing preparation process is to mix beta-cyclodextrin in the easily soluble solvent of iodine for coating, which can form a dynamic equilibrium state of coating and dissolving iodine molecules, so that part of iodine molecules are not tightly combined with the coating, part of iodine volatilizes when cydiodine is dried, the yield of iodine is low, and the manufacturing cost of cydiodine is increased.
The three problems have plagued the world's workers who research cydiodine. So that the cydiodine powder disinfectant has higher production cost and is difficult to realize large-scale production.
Disclosure of Invention
Aiming at overcoming the defects of the traditional technology, the beta-cyclodextrin can competitively coat iodine molecules complexed by povidone when the beta-cyclodextrin is mixed with a povidone iodine solution, the cydiodine prepared by the process has higher stability than the existing preparation process of the cydiodine, the recovery rate of iodine is higher, the coating process is safe and harmless, and no cosolvent is needed. .
In order to solve the problems, the technical scheme adopted by the invention is as follows: the preparation method of cydiodine comprises povidone iodine with mass m and beta-cyclodextrin with mass n, wherein iodine molecules in the povidone iodine have mass m
Said
=
。
As an improvement of the technical scheme: the povidone iodine is povidone iodine solid powder, and the beta-cyclodextrin is beta-cyclodextrin solid powder.
As an improvement of the technical scheme: uniformly mixing the povidone-iodine solid powder and the beta-cyclodextrin solid powder to form solid mixed powder, and pouring water into the solid mixed powder to form a mixed solution, wherein the mass of the mixed solution is
The ratio of 6 x (m + n) is less than or equal to
Heating the mixed solution to 50X (m + n) or less at a temperature of not more than 100 ℃.
As an improvement of the technical scheme: the povidone iodine is povidone iodine solution, and the beta-cyclodextrin is beta-cyclodextrin solid powder.
As an improvement of the technical scheme: pouring the beta-cyclodextrin solid powder into povidone iodine solution to form first solid-liquid mixed slurry, and pouring water into the first solid-liquid mixed slurry to form mixed solution, wherein the mass of the mixed solution is
The ratio of 6 x (m + n) is less than or equal to
Heating the mixed solution to 50X (m + n) or less at a temperature of not more than 100 ℃.
As an improvement of the technical scheme: the povidone iodine is povidone iodine solid powder, and the beta-cyclodextrin is beta-cyclodextrin solution.
As an improvement of the technical scheme: the povidone iodine solid powder is poured into the beta-cyclodextrin solution to form second solid-liquid mixed slurry, water is poured into the second solid-liquid mixed slurry to form mixed solution, and the mass of the mixed solution is
The ratio of 6 x (m + n) is less than or equal to
Heating the mixed solution to 50X (m + n) or less at a temperature of not more than 100 ℃.
As an improvement of the technical scheme: the povidone iodine is povidone iodine solution, and the beta-cyclodextrin is beta-cyclodextrin solution.
As an improvement of the technical scheme: mixing the povidone iodine solution and the beta-cyclodextrin solution to form a concentrated solution, and pouring water into the concentrated solution to form a mixed solution, wherein the mass of the mixed solution is
The ratio of 6 x (m + n) is less than or equal to
Heating the mixed solution to 50X (m + n) or less at a temperature of not more than 100 ℃.
As an improvement of the technical scheme: stirring the mixed solution, cooling, standing for 0.5-12 h until the color of the mixed solution is changed from a dark brown solution into a brownish yellow suspension until a precipitate is generated at the bottom, and clarifying a supernatant; cooling to room temperature, and naturally drying the precipitate at the bottom or oven drying at 0-70 deg.C to obtain cydiodine powder.
Due to the adoption of the technical scheme, compared with the prior art, the technical scheme has the following advantages: 1. the iodine source of the invention uses povidone iodine, and does not use solvent to dissolve iodine, because the povidone iodine does not contain potassium iodide, the cost of the cydiodine is reduced, the raw material is saved, and the impurities in the cydiodine are reduced.
2. The invention does not use dangerous solvents such as ethanol and the like, and does not generate dangerous solution in the preparation process. The invention can complete coating in the state of solution of povidone iodine and beta-cyclodextrin, so the safety is effectively guaranteed.
3. The iodine molecules in the povidone iodine are obtained by utilizing the beta-cyclodextrin in a competitive manner, the beta-cyclodextrin coating competitive force is strong, the iodine ions in the povidone iodine are completely coated to form more stable cydiodine, and the yield of the iodine obtained by utilizing the process reaches more than 99 percent.
4. The cost is lower. The method can obtain the cydiodine by directly mixing the beta-cyclodextrin and the povidone iodine or solution, so the process is simple. In addition, the reacted supernatant is povidone solution, povidone can be recovered for recycling after concentration and spray drying, and the pollution to the environment is less.
Detailed Description
Example 1:
the technical scheme is that beta-cyclodextrin is used for coating iodine molecules to prepare cydiodine, and because the iodine molecules are difficult to dissolve in ethanol, potassium iodide is generally used as a cosolvent in the prior art, although the problem that iodine is dissolved in ethanol is solved, a large amount of free iodide ions and potassium ions are introduced into finally formed cydiodine, the purity of the prepared cydiodine is reduced, and secondly, the potassium ions influence the heart rate of animals and cause harm to the life safety of the animals. In order to solve the problems, the applicant finds that when the beta-cyclodextrin is mixed with the povidone iodine solution, the beta-cyclodextrin can competitively coat iodine molecules complexed by the povidone when the beta-cyclodextrin is mixed with the povidone iodine solution, the stability and the purity of the formed cydiodine are far higher than those of the existing preparation process, the recovery rate of iodine is higher, the coating process is safe and harmless, no cosolvent is used, and the production cost is obviously reduced.
The povidone iodine is a loose compound formed by combining element iodine and a polymer carrier, and is an unstable complex formed by complexing a surfactant and iodine, wherein 80-90% of the combined iodine can be depolymerized into free iodine, so that the mass of iodine molecules in povidone iodine with a certain mass is not determined and unchanged, and the mass of the iodine molecules in the povidone iodine in the technical scheme cannot be determined. The quality of iodine molecules in povidone iodine also needs to be measured through experiments, in this embodiment, povidone iodine is usually dissolved in ethanol to form a povidone iodine solution, and the content of iodine in the povidone iodine solution is measured by using an ultraviolet spectrophotometry. The measurement is based on that the content of iodine is measured at the wavelength of 357.5nm of the absorption peak of the iodine in the povidone-iodine solution, the linear relation of the iodine in the concentration range of 8-18 mug/mL in the povidone-iodine solution is good (r = 0.9996), and the recovery rate of the iodine is (99.62 +/-1.18)%. The method has the advantages of simple measurement, high accuracy and good reproducibility, and the iodine content in the povidone iodine can be obtained by only randomly extracting the iodine from the sample.
The true bookIn the examples, 53.66g of beta-cyclodextrin was taken and 300ml of water was added and dissolved by heating to 85 ℃ to form beta-cyclodextrin. And weighing 200g of povidone iodine solid powder with the iodine molecular content of 6 percent, dissolving the povidone iodine solid powder in 1700ml to form povidone iodine solution, then mixing the two solutions, continuously stirring, naturally cooling until the solution is changed from a black-brown solution into a brownish yellow suspension, standing, precipitating, and obtaining clear supernatant. According to experiments, in an aqueous solution formed by 200g of povidone iodine solid powder with the concentration of 6% and 53.66g of beta-cyclodextrin, the molar ratio of iodine molecules to beta-cyclodextrin is 1: 1, and the two substances are coated in an aqueous solution state to prepare the cydiodine. According to the coating condition of the beta-cyclodextrin and the iodine molecules, a certain proportional relationship exists between the mass of the iodine molecules in the povidone iodine and the beta-cyclodextrin. The applicant obtains the mass of iodine-containing molecules in povidone iodine by repeated experiments
When the iodine molecules in the povidone-iodine can be completely coated by the beta-cyclodextrin with the mass of n, wherein
=
Only if the proportion relation is satisfied, the iodine molecules in the povidone iodine can be completely coated, and impurities cannot be introduced. Therefore, the mass of the beta-cyclodextrin is deduced according to the mass of iodine molecules in the povidone iodine.
Because the iodine molecules in the povidone iodine solid powder can be coated by the beta-cyclodextrin in the solution, the mixed povidone iodine solid powder and the beta-cyclodextrin solid powder need to be completely dissolved in water, and according to the dissolution rate of the povidone iodine and the beta-cyclodextrin, the povidone iodine solid powder and the beta-cyclodextrin solid powder can be completely dissolved only when the mass of the finally formed mixed solution is not less than six times of the sum of the mass of the povidone iodine and the mass of the beta-cyclodextrin, so that the minimum dose of the povidone iodine and the beta-cyclodextrin can be known. According to the proportional relationship, when 1700ml of water and 300ml of water are respectively added into the povidone-iodine solution and the beta-cyclodextrin solution, the relationship that the mass of the mixed solution is not less than six times of the sum of the mass of the povidone-iodine and the mass of the beta-cyclodextrin is satisfied, so that the povidone-iodine solution and the beta-cyclodextrin solution in the embodiment do not need to be added with water again after being mixed.
Mixing the povidone iodine solution and the beta-cyclodextrin solution, continuously stirring, naturally cooling until the solution is changed into brown yellow suspension from a black-brown solution, standing for 0.5h to precipitate, and clarifying the supernatant. After all the precipitate is precipitated, the precipitate is taken out and naturally dried to loose powder, and the cydiodine solid powder is obtained.
And (3) effect comparison:
according to the 51 st publication of Xidi iodine powder veterinary drug product quality standard in 2018 of Ministry of agriculture, the yields of iodide ions, available iodine and iodine of products obtained by three preparation processes of example 1 (No. A), ZL200810014514.7 (No. B) and 1991 (publication No. CN 1049099A) (No. C) of the patent are compared.
The test results are as follows:
| numbering | Content of iodide ion | Effective iodine content | Yield of iodine |
| A | 0.07% | 17.68% | 99.11% |
| B | 1.32% | 17.75% | 92.62% |
| C | 5.41% | 18.15% | 90.55% |
The experimental results show that: the product obtained by the method of example 1 has the lowest content of iodide ions, and trace iodide ions may be caused by impure iodine raw materials; the iodine yield is also highest, which should be associated with competitive binding of beta-cyclodextrin to povidone. The highest iodine content in code C of the three methods may be related to the excess iodine used in the process, but the iodide ion is high and the yield is lowest. In summary, the iodine ion content and the effective iodine content in the number a are the lowest, and the iodine yield is the highest, which fully indicates that the cydiodine preparation process in the embodiment has the advantages of less impurities, better effect and higher safety.
Example 2:
the preparation method in example 1 is to mix the povidone-iodine solution and the β -cyclodextrin solution to obtain a mixed solution, and the preparation method is a mixing method commonly used in biochemistry, and has the advantages of uniform mixing and short reaction time. However, this method requires pouring one solution into the other solution, and when the solution volume is large, the difficulty of mixing the solutions increases, and thus the difficulty of mass production is large. In order to overcome the above problems, the present embodiment adopts a method of uniformly mixing povidone-iodine solid powder and beta-cyclodextrin powder, and then injecting water into the mixed solid powder.
In this example, 253.8g of povidone-iodine solid powder with 10% iodine molecule content was weighed, and according to the experiment, molecular iodine was uniformly mixed with 113.5g of beta-cyclodextrin solid powder, and according to the coating condition of beta-cyclodextrin and iodine molecule, the molecular iodine mass in povidone-iodine was found to beA certain proportional relation exists between the beta-cyclodextrin and the beta-cyclodextrin. The applicant obtains the mass of iodine-containing molecules in povidone iodine by repeated experiments
When the iodine molecules in the povidone-iodine can be completely coated by the beta-cyclodextrin with the mass of n, wherein
=
Only if the proportion relation is satisfied, the iodine molecules in the povidone iodine can be completely coated, and impurities cannot be introduced. Therefore, when 253.8g of povidone iodine solid powder is taken, the mass of the beta-cyclodextrin solid powder is 113.5 g.
Because the iodine molecules in the povidone iodine solid powder can be coated by the beta-cyclodextrin in the solution, the mixed povidone iodine solid powder and the beta-cyclodextrin solid powder need to be completely dissolved in water, and according to the dissolution rate of the povidone iodine and the beta-cyclodextrin, the finally formed mixed solution can be completely dissolved when the mass of the finally formed mixed solution is not less than six times of the sum of the mass of the povidone iodine and the mass of the beta-cyclodextrin, so that the mass of the mixed solution poured into the water can be known. In this example, 5000ml of water was added to the solid mixed powder according to the ratio, and the mixture was slowly heated at 100 ℃ until all the water was dissolved. The povidone iodine and the beta-cyclodextrin are both solid powder, and the difficulty of completely dissolving the solid mixed powder in water is high, so that the solid mixed powder is assisted to be dissolved at 100 ℃, and the chemical properties of the povidone iodine and the beta-cyclodextrin can be known that the higher the temperature is, the higher the dissolution rate is, but the higher the temperature is, the higher the volatility of iodine molecules is, and the overlarge volatilization of the iodine molecules causes influence on the yield of cydiodine, so that the applicant selects the temperature not to exceed 100 ℃ after repeated experiments, not only is the dissolving time of the povidone iodine solid powder and the beta-cyclodextrin solid powder shortened, but also the volatilization of the iodine molecules is avoided.
Stopping heating, stirring continuously until the solution is naturally cooled, and standing for 12h until the brown suspension is precipitated and the supernatant is clear after the solution is changed from black brown to brown yellow suspension. And cooling to room temperature, and naturally drying to obtain the cydiodine powder.
Example 3
Even though the povidone-iodine solid powder and the beta-cyclodextrin solid powder are uniformly mixed, when water is injected into the solid mixed powder, once the water is not uniformly stirred in the water injection process, the beta-cyclodextrin coats iodine molecules, and partial solid mixed powder is coated inside and is difficult to dissolve in water, so that the forming of the cydiodine is influenced.
In this example, 253.8g of povidone-iodine solid powder containing 5% of iodine molecules is weighed, povidone-iodine is dissolved in 3000ml of water to form a povidone-iodine solution, then 56.75g of beta-cyclodextrin solid powder is added to the povidone-iodine solution, the mixed solution is heated at 80 ℃, stirring is continuously performed, after the beta-cyclodextrin solid powder is completely dissolved, the solution is converted from a dark brown solution into a brownish yellow suspension, and the mixed solution is allowed to stand for 8 hours, precipitated, and the supernatant is clear. After all the precipitate is precipitated, taking the precipitate and drying the precipitate at 60 ℃ until the precipitate is loose powder.
Example 4
Example 3 is to add solid beta-cyclodextrin powder to povidone-iodine solution to avoid incomplete dissolution of the povidone-iodine solid powder and the solid beta-cyclodextrin powder caused by water injection into the povidone-iodine solid powder and the solid beta-cyclodextrin powder. It is therefore known that povidone-iodine solid powder can be added to the β -cyclodextrin solution as well.
A novel preparation technology of cydiodine is prepared from povidone iodine and beta-cyclodextrin. Weighing 125g of beta-cyclodextrin solid powder, and slowly heating to 40 ℃ by using 2800ml of water for dissolving; and 279.51g of povidone iodine solid powder containing 10% of iodine molecules is weighed, then the povidone iodine solid powder is slowly added into the beta-cyclodextrin solution and is continuously stirred and dissolved until the solution is changed from black brown to brown yellow suspension, and precipitation can occur after standing, and the supernatant is clear. Cooling to room temperature, and drying the precipitate at 50 deg.C to obtain loose powder.
As the cydiodine is required to be finally dried during the forming process, the volatilization of iodine is also accompanied in the drying process, and the yield of the cydiodine is influenced, the water consumption is controlled as much as possible in the preparation process, the subsequent drying time is saved, and the energy is saved. After mixing the povidone-iodine solution with the beta-cyclodextrin solution in example 1, no water was injected into the concentrate, since the total mass of water in the two solutions had met the minimum requirements. The quality of the first solid-liquid mixed slurry and the second solid-liquid mixed slurry formed in the examples 3 and 4 also meets the minimum quality requirement, and therefore, water is not injected into the inner part.
The above detailed description of the specific embodiments of the present invention is the best mode for carrying out the present invention and should not be taken as limiting the scope of the present invention. It will be appreciated by those skilled in the art that any equivalent modifications or alterations to the present invention are also within the scope of the present invention.
Claims (10)
1. A preparation method of cydiodine is characterized in that: comprises povidone iodine with mass m and beta-cyclodextrin with mass n, wherein iodine molecules in the povidone iodine have mass m
Said
=
。
2. The method of claim 1, wherein the step of preparing cydiodine comprises: the povidone iodine is povidone iodine solid powder, and the beta-cyclodextrin is beta-cyclodextrin solid powder.
3. The method of claim 2, wherein the step of preparing cydiodine comprises: the povidone iodine solid powderUniformly mixing the beta-cyclodextrin solid powder with the beta-cyclodextrin solid powder to form solid mixed powder, and pouring water into the solid mixed powder to form mixed solution, wherein the mass of the mixed solution is
The ratio of 6 x (m + n) is less than or equal to
Heating the mixed solution to 50X (m + n) or less at a temperature of not more than 100 ℃.
4. The method of claim 1, wherein the step of preparing cydiodine comprises: the povidone iodine is povidone iodine solution, and the beta-cyclodextrin is beta-cyclodextrin solid powder.
5. The method of claim 4, wherein the step of preparing cydiodine comprises: pouring the beta-cyclodextrin solid powder into povidone iodine solution to form first solid-liquid mixed slurry, and pouring water into the first solid-liquid mixed slurry to form mixed solution, wherein the mass of the mixed solution is
The ratio of 6 x (m + n) is less than or equal to
Heating the mixed solution to 50X (m + n) or less at a temperature of not more than 100 ℃.
6. The method of claim 1, wherein the step of preparing cydiodine comprises: the povidone iodine is povidone iodine solid powder, and the beta-cyclodextrin is beta-cyclodextrin solution.
7. The method of claim 6, wherein the step of preparing cydiodine comprises: the povidone iodine solid powder is poured into the beta-cyclodextrin solution, and a second solid-liquid mixed slurry is formed, andwater is poured into the second solid-liquid mixed slurry to form a mixed solution, and the mass of the mixed solution is
The ratio of 6 x (m + n) is less than or equal to
Heating the mixed solution to 50X (m + n) or less at a temperature of not more than 100 ℃.
8. The method of claim 1, wherein the step of preparing cydiodine comprises: the povidone iodine is povidone iodine solution, and the beta-cyclodextrin is beta-cyclodextrin solution.
9. The method of claim 8, wherein the step of preparing cydiodine comprises: mixing the povidone iodine solution and the beta-cyclodextrin solution to form a concentrated solution, and pouring water into the concentrated solution to form a mixed solution, wherein the mass of the mixed solution is
The ratio of 6 x (m + n) is less than or equal to
Heating the mixed solution to 50X (m + n) or less at a temperature of not more than 100 ℃.
10. The method of claim 2, 4, 6 or 8, wherein the step of preparing cydiodine comprises: continuously stirring the mixed solution until the mixed solution is cooled, standing for 0.5-12 h until the color of the mixed solution is changed from a dark brown solution into a brownish yellow suspension until a precipitate is generated at the bottom, and clarifying a supernatant; cooling to room temperature, and naturally drying the precipitate at the bottom or oven drying at 0-70 deg.C to obtain cydiodine powder.
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| CN102349541A (en) * | 2011-08-10 | 2012-02-15 | 寇志民 | New application of iodine cyclodextrin inclusion compound |
| CN103393717A (en) * | 2013-07-23 | 2013-11-20 | 何元龙 | Method for preparing high-water-solubility cydiodine with low cost |
| WO2014023718A1 (en) * | 2012-08-07 | 2014-02-13 | Dräger Safety AG & Co. KGaA | Disinfectant containing a complex of iodine and cyclodextrin |
| CN107517963A (en) * | 2017-08-31 | 2017-12-29 | 山东省农业科学院家禽研究所 | A kind of high stability BETA Cyclodextrin Inclusion Compound of Iodine powder and its preparation, application method |
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2021
- 2021-11-02 CN CN202111285826.3A patent/CN113831424A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4844898A (en) * | 1986-09-02 | 1989-07-04 | Kowa Co., Ltd. | Wound-healing preparations |
| JPH1045609A (en) * | 1996-08-05 | 1998-02-17 | Nippo Kagaku Kk | New inclusion compound, its use and resin composition |
| JP2006335751A (en) * | 2005-06-06 | 2006-12-14 | Nippo Kagaku Kk | METHOD FOR PRODUCING INCLUSION COMPOUND OF SOLID METHYLATED beta-CYCLODEXTRIN WITH IODINE |
| CN102078611A (en) * | 2009-11-26 | 2011-06-01 | 天津金耀集团有限公司 | Partial external use composition containing povidone Iodine and cyclodextrin inclusion glucocorticoid |
| CN102349541A (en) * | 2011-08-10 | 2012-02-15 | 寇志民 | New application of iodine cyclodextrin inclusion compound |
| WO2014023718A1 (en) * | 2012-08-07 | 2014-02-13 | Dräger Safety AG & Co. KGaA | Disinfectant containing a complex of iodine and cyclodextrin |
| CN103393717A (en) * | 2013-07-23 | 2013-11-20 | 何元龙 | Method for preparing high-water-solubility cydiodine with low cost |
| CN107517963A (en) * | 2017-08-31 | 2017-12-29 | 山东省农业科学院家禽研究所 | A kind of high stability BETA Cyclodextrin Inclusion Compound of Iodine powder and its preparation, application method |
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