CN102807517A - Synthesis of garlicin derivatives and preparation method for medical ultrasonic couplant with efficient disinfection function using garlicin derivatives - Google Patents
Synthesis of garlicin derivatives and preparation method for medical ultrasonic couplant with efficient disinfection function using garlicin derivatives Download PDFInfo
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- CN102807517A CN102807517A CN 201110147815 CN201110147815A CN102807517A CN 102807517 A CN102807517 A CN 102807517A CN 201110147815 CN201110147815 CN 201110147815 CN 201110147815 A CN201110147815 A CN 201110147815A CN 102807517 A CN102807517 A CN 102807517A
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Abstract
The invention relates to a synthesis method of garlicin derivatives, and a preparation method of a medical ultrasonic couplant with disinfection and sterilization functions using the garlicin derivatives as efficient antimicrobial agent. Formula (I) is shown in the specification.
Description
Technical field:
The present invention relates to the compound method of one type of garlicin derivative (formula I or formula II), and be used to have the preparation method of the medical ultrasonic coupling agent of disinfecting and sterilizing functions as efficient germicide.
Formula (I) formula (II)
R wherein
1With R
2Can be identical, also can be different, be C
1-C
4Alkane or alkene; Be recommended as methyl, ethyl, propyl group, butyl, sec.-propyl or allyl group;
Background technology:
Current development along with modern ultrasonic technique, Ultrasonic Diagnosis and ultrasound treatment widespread use in medical treatment has also been come out with Ultrasonic Diagnosis and the closely-related medical ultrasonic coupling agent of ultrasound treatment effect simultaneously.UW is identical with sound wave, all need rely on medium to propagate, and produces reflection, phenomenons such as refraction on the interface that constitutes with different media.The acoustic resistance difference that how much relies on medium of ultrasonic reflections decides, and the acoustic resistance difference of both sides, interface material is bigger, reflects the more, and the UW that promptly gets into second medium is fewer.Therefore, at the interface that body soft tissue and water constitute, ultrasonic reflections seldom, but the interface that air and soft tissue constitute, then a large amount of ultrasonic energies are lost owing to reflecting.When diagnosis of using ultrasound ripple or ultrasonic therapy,, need to fill the space between skin and the sound head with medical ultrasonic coupling agent in order to eliminate the loss that UW causes because of reflection.The acoustic resistance of couplant should be close with the acoustic resistance of human body soft tissue.The acoustic resistance (10 of several kinds of materials
5G/cm
2S) as follows: human body soft tissue 1.59; Fatty tissue: 1.50; Muscle tissue: 1.49; Air: 0.000439; Water: 1.52. all has medical ultrasonic coupling agent production at present both at home and abroad.
The function of traditional medical ultrasonic coupling agent is the coupling of strengthening between ultrasound probe and the human body skin, and isolated ultrasound probe and be examined the air between the skin of position makes the sound wave conduction not receive air influence and decays, to reach good detection effect.
In sum; The sterilization of ultrasound probe is a great problem that always perplexs medical supersonic diagnostic detection and treatment; Major cause; The one, no suitable compound, because the singularity of ultrasound probe material, the sterilizing agent that has determined at present great majority on the market that this kind plastics and rubber are had corrodibility or a swelling property can not be used for the sterilization of ultrasound probe; The 2nd, no suitable medium because the singularity of structure of ultrasonic makes it can not use conventional infusion method to carry out disinfection, requires high to medium; The 3rd, disinfecting time; Because of operating frequency is high, the interval between the seized patient is very short, the interior sterilizing agent there be limited evidence currently of of kill bacteria, mould and fungi simultaneously of so short time; Effect is also often bad; And existing medical ultrasonic coupling agent ubiquity safe reliability is poor, it is inconvenient to use, and cost is higher, is inappropriate for large-scale popularization and application.
Simultaneously; In the state of the art; Preparation process with medical ultrasonic coupling agent of sterilization effect often exists and has corrodibility and irritating composition, possibly produce murder by poisoning to the related personnel who produces and use, and threatens also to cause environmental pollution healthy the time.
Therefore; Urgent need is sought a kind of have wide spectrum, the quick sterilizing ability efficiently that reaches; Do not influence the safety non-toxic of ultrasonic effect and Imidazolidinyl Urea not again; Can not corrode medical ultrasonic probe, the medical ultrasonic coupling agent that the preparation process is simple and safe and with low cost simultaneously being examined skin surface generation delay germicidal action.
For this reason, the invention provides the novel synthesis of one type of garlicin derivative, this method is mild condition not only, and is easy and simple to handle, and reaction yield is high, clean environment firendly.This compounds has the excellent antibiotic sterilizing ability simultaneously, and is all effective to various bacteria, fungi and mould, and the preparation method is simple, with low cost, can be used as the medical ultrasonic coupling agent that efficient germicide is used to have the preparation disinfecting and sterilizing functions.
Summary of the invention
The object of the present invention is to provide the simple and effective compound method of one type of garlicin derivative, it can be used as the medical ultrasonic coupling agent that efficient germicide is used to have the preparation disinfecting and sterilizing functions.Another object of the present invention is to provide a kind of above-mentioned preparation method with medical ultrasonic coupling agent of preparation disinfecting and sterilizing functions.
In order to solve the problems of the technologies described above, last technical scheme of the present invention is: utilize the substituted disulphide of various alkyl, under the proline(Pro) of catalytic amount promotes, obtain one type of garlicin derivative with hydroperoxidation.It is characterized in that obtaining through the method for following step (a) or step (b):
(a). with
(formula III) is raw material; In solvent; The proline(Pro) of catalytic amount promotes down, can obtain the compound of formula (I) or formula (II) with hydroperoxidation;
Said R
1With R
2Can be identical, also can be different, be C
1-C
4Alkane or alkene; Be recommended as methyl, ethyl, propyl group, butyl, sec.-propyl or allyl group;
Said formula (III) is 1 with the mol ratio of hydrogen peroxide: (1-5); Be recommended as 1: (1-3);
The temperature of said reaction is between 0-60 ℃; Be recommended as between 0-40 ℃;
The required solvent of said reaction is water, ETHYLE ACETATE, THF, methyltetrahydrofuran, t-butyl methyl ether, acetonitrile, methylene dichloride or 1, the 2-ethylene dichloride; Be recommended as water, t-butyl methyl ether, acetonitrile, methylene dichloride or 1, the 2-ethylene dichloride;
(b). with
(formula III) is raw material; In solvent; The proline(Pro) of catalytic amount promotes down; Add oxygenant A, formula (III) can obtain formula (I) or formula (II) compound with hydroperoxidation;
Said R
1With R
2Definition such as step (a) said;
Said formula (III) is 1 with the mol ratio of hydrogen peroxide: (1-5);
The temperature of said reaction is between 0-60 ℃;
The required solvent of said reaction is water, ETHYLE ACETATE, THF, methyltetrahydrofuran, t-butyl methyl ether, acetonitrile, methylene dichloride or 1, the 2-ethylene dichloride; Be recommended as water, ETHYLE ACETATE, methyltetrahydrofuran, t-butyl methyl ether, acetonitrile or 1, the 2-ethylene dichloride;
Said oxygenant A is the vitriol oil, concentrated nitric acid, chlorine, Youxiaolin, peroxy tert-butyl alcohol or metachloroperbenzoic acid; Be recommended as concentrated nitric acid, chlorine, peroxy tert-butyl alcohol or metachloroperbenzoic acid;
The mol ratio of said oxygenant and hydrogen peroxide is 1: (1-5); Be recommended as 1: (1-4);
Back of the present invention one technical scheme provides above-mentioned medical ultrasonic coupling agent and preparation method with preparation disinfecting and sterilizing functions; Specifically describe as follows: said medical ultrasonic coupling agent with disinfecting and sterilizing functions is characterized in that mainly being selected from viscosity modifier 0.1-1.5%, sterilant 0.01-0.15%, essence 0.01-0.05%, solvating agent 1-10%, neutralizing agent 0.1-1%, all the other are made up of deionized water;
Wherein, described medical ultrasonic coupling agent with disinfecting and sterilizing functions is characterized in that said sterilant is for having
(formula I) or
The compound of (formula II) structure, R
1With R
2Definition as previously mentioned; Said viscosity modifier is that one or more combine in Natvosol, carbomer, the hydroxypropylcellulose; Said essence is that one or more of geraniol, rose oil, orange flower oil, PH 6968 or Therapeutic Mineral Ice combine; Said solvating agent is a kind of composition in Ucar 35, USP Kosher or the polyoxyethylene glycol; Said neutralizing agent is trolamine or sodium hydroxide;
Medical ultrasonic coupling agent with disinfecting and sterilizing functions of the present invention; It is characterized in that comprising following component: Natvosol 0.1-0.2%, methyl thiosulfonates 0.01-0.15%, geraniol 0.01-0.03%, USP Kosher 1-10%, all the other are deionized water.
Medical ultrasonic coupling agent with disinfecting and sterilizing functions of the present invention; It is characterized in that composed of the following components: hydroxypropylcellulose 0.1-0.2%, ethylenebis dithiocarbamate sulphonate 0.01-0.15%, Therapeutic Mineral Ice 0.01-0.05%, Ucar 35 1-10%, all the other are deionized water.
Medical ultrasonic coupling agent with disinfecting and sterilizing functions of the present invention; It is characterized in that composed of the following components: carbomer 0.6-1.5%, ethylenebis dithiocarbamate-sulfinic acid ester 0.01-0.15%, orange flower oil 0.01-0.02%, PH 6968 0.01-0.03%, trolamine 0.1-0.5%, USP Kosher 1-10%, all the other are deionized water.
Preparation process with medical ultrasonic coupling agent of disinfecting and sterilizing functions of the present invention; It is characterized in that: take by weighing viscosity modifier and solvating agent by weight percentage, the two is mixed, the deionized water and stirring that adds capacity is disperseed; Be heated to 60-80 ℃; Be incubated 30-60 minute, be cooled to 30-50 ℃ of adding sterilant and essence, the back can stirs.
Beneficial effect with medical ultrasonic coupling agent of disinfecting and sterilizing functions of the present invention is through the tests such as relevant ultrasonic unit area impedance, sound attenuation, sterilizing power, skin and mucous membrane irritation property, toxicity and rubber corrosiveness to the efficient sterilizing type medical ultrasonic coupling agent that is used for skin and cavity mucous membrane, proves that product of the present invention meets relevant each item and requires and standard.
Embodiment
Following examples help to understand this patent but are not limited thereto scope.
The preparation of methyl sulfo--sulfinic acid methyl esters:
DMDS (20g) and L-proline(Pro) (2g) are dissolved in acetonitrile (10ml), under 0 ℃ to wherein drip ydrogen peroxide 50 (30%, 40g); Fully nature heats up 25 ℃ under the stirring, and the back system that reacts completely reduces pressure down except that acetonitrile at 20 ℃, adds the dichloromethane extraction layering; Add the saturated common salt water washing once, anhydrous sodium sulfate drying goes out to desolvate at 20 ℃ of following concentrating under reduced pressure; Get methyl sulfo--sulfinic acid methyl esters 18.7g, yield 80%.
The preparation of methyl thiosulfonic acid methyl esters:
DMDS (40g) and L-proline(Pro) (4g) are dissolved in methyltetrahydrofuran (10ml), under 10 ℃ to wherein drip ydrogen peroxide 50 (30%, 150g); Fully nature heats up 30 ℃ under the stirring, and the back system that reacts completely reduces pressure down except that THF at 20 ℃, adds the dichloromethane extraction layering; Add the saturated common salt water washing once, anhydrous sodium sulfate drying goes out to desolvate at 20 ℃ of following concentrating under reduced pressure; Get methyl thiosulfonic acid methyl esters 46.2g, yield 85%.
The preparation of ethylenebis dithiocarbamate-sulfinic acid ethyl ester:
Diethylammonium two sulphur (100g) and L-proline(Pro) (5g) are dissolved in 1,2-ethylene dichloride (40ml), under 10 ℃ to wherein dripping ydrogen peroxide 50 (30%; 160g), be warmed up to 40 ℃ under fully stirring, the back that reacts completely adds the dichloromethane extraction layering; Add the saturated common salt water washing once, anhydrous sodium sulfate drying goes out to desolvate at 20 ℃ of following concentrating under reduced pressure; Get ethylenebis dithiocarbamate-sulfinic acid ethyl ester 90.2g, yield 80%.
The preparation of O-Ethyl ethanesulfonothioate:
Diethylammonium two sulphur (10g) and L-proline(Pro) (1g) are dissolved in THF (10ml), under 10 ℃ to wherein drip ydrogen peroxide 50 (30%, 22g), fully stir down; Add acetic acid (5g) again, slowly be warmed up to 60 ℃, system reduces pressure down at 20 ℃ and removes methyltetrahydrofuran, adds the dichloromethane extraction layering; Add saturated sodium bicarbonate solution and wash once, add the saturated common salt water washing once, anhydrous sodium sulfate drying; Go out to desolvate at 20 ℃ of following concentrating under reduced pressure, get O-Ethyl ethanesulfonothioate 9.2g, yield 78%.
The preparation of allyl group thiosulfonic acid allyl ester:
Diallyl disulfide (10g) and L-proline(Pro) (1g) water-soluble (10ml), under 10 ℃ to wherein drip ydrogen peroxide 50 (30%, 22g); Be warmed up to 40 ℃ under fully stirring, the back that reacts completely adds the dichloromethane extraction layering, adds the saturated common salt water washing once; Anhydrous sodium sulfate drying; Go out to desolvate at 20 ℃ of following concentrating under reduced pressure, get allyl group thiosulfonic acid allyl ester 10.1g, yield 82%.
Embodiment 6
Match well by following component and weight percent and to get:
Natvosol 0.1-0.2%, methyl sulfo-methyl mesylate 0.01-0.15%, geraniol 0.01-0.03%, USP Kosher 1-10%, all the other are deionized water.
Method for making: Natvosol is distributed in the USP Kosher, and the deionized water and stirring that adds capacity is disperseed, and is heated to 60-80 ℃, is incubated 30 minutes, is being cooled to 45 ℃ of adding methyl sulfo-methyl mesylates and geraniol, and cooling back can stirs.
Be example with this medical ultrasonic coupling agent of configuration 1000Kg as follows, take by weighing by following weight:
Natvosol 2000g, methyl sulfo-methyl mesylate 100g, geraniol 100g, USP Kosher 100Kg, deionized water 897.8Kg.
Preparing method: Natvosol (2000g) is distributed in the USP Kosher (100Kg); Deionized water (897.8Kg) dispersed with stirring that adds capacity; Be heated to 60-80 ℃; Be incubated 30 minutes, be cooled to 45 ℃ of adding methyl sulfo-methyl mesylates (100g) and geraniol (100g), cooling back can stirs.
Embodiment 7
Match well by following component and weight percent and to get:
Hydroxypropylcellulose 0.1-0.2%, O-Ethyl ethanesulfonothioate 0.01-0.15%, Therapeutic Mineral Ice 0.01-0.05%, Ucar 35 1-10%, all the other are deionized water.
Method for making: hydroxypropylcellulose is distributed in the Ucar 35, and the deionized water and stirring that adds capacity is disperseed, and is heated to 60-80 ℃, is incubated 50 minutes, is being cooled to 40 ℃ of adding ethylenebis dithiocarbamate ethyl methane sulfonates and Therapeutic Mineral Ice, and cooling back can stirs.
Be example with this medical ultrasonic coupling agent of configuration 1000Kg as follows, take by weighing by following weight:
Hydroxypropylcellulose 2000g, O-Ethyl ethanesulfonothioate 120g, Therapeutic Mineral Ice 150g, Ucar 35 100Kg, deionized water 897.7Kg.
Preparing method: hydroxypropylcellulose (2000g) is distributed in the Ucar 35 (100Kg); Deionized water (897.7Kg) dispersed with stirring that adds capacity; Be heated to 60-80 ℃; Be incubated 50 minutes, be cooled to 40 ℃ of adding ethylenebis dithiocarbamate ethyl methane sulfonates (120g) and Therapeutic Mineral Ice (150g), cooling back can stirs.
Embodiment 8
Match well by following component and weight percent and to get:
Carbomer 0.6-1.5%, ethylenebis dithiocarbamate-sulfinic acid ethyl ester 0.01-0.15%, orange flower oil 0.01-0.02%, PH 6968 0.01-0.03%, trolamine 0.1-0.5%, USP Kosher 1-10%, all the other are deionized water.
Method for making: carbomer is distributed in the USP Kosher; The deionized water and stirring that adds capacity is disperseed, and is heated to 60-80 ℃, is incubated 60 minutes; Be cooled to 30 ℃ of adding ethylenebis dithiocarbamate-sulfinic acid ethyl esters, orange flower oil, PH 6968 and trolamines, cooling back can stirs.
Be example with this medical ultrasonic coupling agent of configuration 1000Kg as follows, take by weighing by following weight:
Carbomer 15Kg, ethylenebis dithiocarbamate-sulfinic acid ethyl ester 240g, orange flower oil 100g, PH 6968 100g, trolamine 1Kg, USP Kosher 100Kg, deionized water 883.6Kg.
Preparing method: carbomer (15Kg) is distributed in the USP Kosher (100Kg); Deionized water (883.6Kg) dispersed with stirring that adds capacity; Be heated to 60-80 ℃; Be incubated 60 minutes, be cooled to 30 ℃ of adding ethylenebis dithiocarbamate-sulfinic acid ethyl esters (240g), orange flower oil (100g), PH 6968 (100g) and trolamines (1Kg), cooling back can stirs.
To the medical ultrasonic coupling agent of the foregoing description, relevant ultrasonic unit area impedance, sound attenuation, sterilizing power, skin mucosa pungency, toxicity, rubber corrosiveness etc. are carried out a series of experiment, experimental result is following: under 25 ℃ of conditions, viscosity>=15Pa.s; The pH value is 5.5~8; Recording the velocity of sound under 35 ℃ is that 1510~1620m/s, specific acoustic impedance are 1.5 * 10
6~1.7 * 10
6Pa.s/m, sound attenuation≤0.05dB/ (cm.MHz); Its virus killing, bactericidal property; Total plate count≤1000/mL or 1000/g; That is to say in every gram or every milliliter of product and must not check out excrement colibacillus group, Pseudomonas aeruginosa and staphylococcus aureus, to sterilizing rate>=90% of streptococcus aureus, intestinal bacteria and Candida albicans.TP and test-results all meet corresponding national standards.
Claims (15)
1. the novel synthesis of a garlicin derivative, described structural general formula is as follows:
Formula (I) formula (II)
R in the formula
1With R
2Can be identical, also can be different, be C
1-C
4Alkane or alkene;
2. R according to claim 1,
1With R
2Can be identical, also can be different, be methyl, ethyl, propyl group, butyl, sec.-propyl or allyl group;
3. the novel synthesis of garlicin derivative as claimed in claim 1 is characterized in that obtaining through the method for following step (a) or step (b):
(a). with
(formula III) is raw material; In solvent; The proline(Pro) of catalytic amount promotes down, can obtain the compound of formula (I) or formula (II) with hydroperoxidation;
Said R
1With R
2Definition according to claim 1;
Said formula (III) is 1 with the mol ratio of hydrogen peroxide: (1-5);
The temperature of said reaction is between 0-60 ℃;
The required solvent of said reaction is water, ETHYLE ACETATE, THF, methyltetrahydrofuran, t-butyl methyl ether, acetonitrile, methylene dichloride or 1, the 2-ethylene dichloride;
(b). with
(formula III) is raw material; In solvent; The proline(Pro) of catalytic amount promotes down; Add oxygenant A, formula (III) can obtain formula (I) or formula (II) compound with hydroperoxidation;
Said R
1With R
2Definition according to claim 1;
Said formula (III) is 1 with the mol ratio of hydrogen peroxide: (1-5);
The temperature of said reaction is between 0-60 ℃;
The required solvent of said reaction is water, ETHYLE ACETATE, THF, methyltetrahydrofuran, t-butyl methyl ether, acetonitrile, methylene dichloride or 1, the 2-ethylene dichloride;
Said oxygenant A is the vitriol oil, concentrated nitric acid, chlorine, Youxiaolin, peroxy tert-butyl alcohol or metachloroperbenzoic acid;
The mol ratio of said oxygenant and hydrogen peroxide is 1: (1-5);
4. the novel synthesis of garlicin derivative as claimed in claim 3 is characterized in that in the step (a):
Said R
1With R
2Definition according to claim 1;
Said formula (III) is 1 with the mol ratio of hydrogen peroxide: (1-3);
The temperature of said reaction is between 0-40 ℃;
The required solvent of said reaction is water, t-butyl methyl ether, acetonitrile, methylene dichloride or 1, the 2-ethylene dichloride;
In the step (b):
The required solvent of said reaction is water, ETHYLE ACETATE, methyltetrahydrofuran, t-butyl methyl ether, acetonitrile or 1, the 2-ethylene dichloride;
Said oxygenant A is concentrated nitric acid, chlorine, peroxy tert-butyl alcohol or metachloroperbenzoic acid;
The mol ratio of said oxygenant A and hydrogen peroxide is 1: (1-4);
5. according to claim 1, it is characterized in that described garlicin derivative can be used as efficient germicide and is used to prepare the medical ultrasonic coupling agent with disinfecting and sterilizing functions;
6. the medical ultrasonic coupling agent with disinfecting and sterilizing functions as claimed in claim 5 is characterized in that mainly being selected from viscosity modifier 0.1-1.5%, sterilant 0.05-0.15%, essence 0.01-0.05%, solvating agent 1-10%, neutralizing agent 0.1-1%, all the other are made up of deionized water;
8. the medical ultrasonic coupling agent with disinfecting and sterilizing functions as claimed in claim 6 is characterized in that said viscosity modifier is that one or more combine in Natvosol, carbomer, the hydroxypropylcellulose;
9. the medical ultrasonic coupling agent with disinfecting and sterilizing functions as claimed in claim 6 is characterized in that said essence is that one or more of geraniol, rose oil, orange flower oil, PH 6968 or Therapeutic Mineral Ice combine;
10. the medical ultrasonic coupling agent with disinfecting and sterilizing functions as claimed in claim 6 is characterized in that said solvating agent is a kind of composition in Ucar 35, USP Kosher or the polyoxyethylene glycol;
11. the medical ultrasonic coupling agent with disinfecting and sterilizing functions as claimed in claim 6 is characterized in that said neutralizing agent is trolamine or sodium hydroxide;
12. the medical ultrasonic coupling agent with disinfecting and sterilizing functions as claimed in claim 6; It is characterized in that said medical ultrasonic coupling agent comprises following component: Natvosol 0.1-0.2%, methyl sulfo-methanesulfonates 0.01-0.15%, geraniol 0.01-0.03%, USP Kosher 1-10%, all the other are deionized water.
13. the medical ultrasonic coupling agent with disinfecting and sterilizing functions as claimed in claim 6; It is characterized in that composed of the following components: hydroxypropylcellulose 0.1-0.2%, ethylenebis dithiocarbamate methanesulfonates 0.01-0.15%, Therapeutic Mineral Ice 0.01-0.05%, Ucar 35 1-10%, all the other are deionized water.
14. the medical ultrasonic coupling agent with disinfecting and sterilizing functions as claimed in claim 6; It is characterized in that composed of the following components: carbomer 0.6-1.5%, ethylenebis dithiocarbamate methylene sulphonate 0.01-0.15%, orange flower oil 0.01-0.02%, PH 6968 0.01-0.03%, trolamine 0.1-0.5%, USP Kosher 1-10%, all the other are deionized water.
15. the preparation process with medical ultrasonic coupling agent of disinfecting and sterilizing functions as claimed in claim 5; It is characterized in that: take by weighing viscosity modifier and solvating agent by weight percentage, the two is mixed, the deionized water and stirring that adds capacity is disperseed; Be heated to 60-80 ℃; Be incubated 30-60 minute, be cooled to 30-50 ℃ of adding sterilant and essence, the back can stirs.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103058903A (en) * | 2011-10-21 | 2013-04-24 | 中国科学院上海有机化学研究所 | Synthesis method for allicin derivative |
CN104984368A (en) * | 2015-06-30 | 2015-10-21 | 苏州乔纳森新材料科技有限公司 | Medical ultrasonic coupling agent and preparation method thereof |
CN108084070A (en) * | 2017-12-14 | 2018-05-29 | 浙江海洋大学 | A kind of preparation of xanthate and its application in antifouling paint |
-
2011
- 2011-06-02 CN CN 201110147815 patent/CN102807517A/en active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103058903A (en) * | 2011-10-21 | 2013-04-24 | 中国科学院上海有机化学研究所 | Synthesis method for allicin derivative |
CN104984368A (en) * | 2015-06-30 | 2015-10-21 | 苏州乔纳森新材料科技有限公司 | Medical ultrasonic coupling agent and preparation method thereof |
CN108084070A (en) * | 2017-12-14 | 2018-05-29 | 浙江海洋大学 | A kind of preparation of xanthate and its application in antifouling paint |
CN108084070B (en) * | 2017-12-14 | 2020-04-14 | 浙江海洋大学 | Preparation of thiosulfinate compound and application of thiosulfinate compound in antifouling paint |
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