CN102924496B - Method for preparing anti-bacterial compound - Google Patents
Method for preparing anti-bacterial compound Download PDFInfo
- Publication number
- CN102924496B CN102924496B CN201210377540.2A CN201210377540A CN102924496B CN 102924496 B CN102924496 B CN 102924496B CN 201210377540 A CN201210377540 A CN 201210377540A CN 102924496 B CN102924496 B CN 102924496B
- Authority
- CN
- China
- Prior art keywords
- antiseptic
- germicide
- preparation
- reaction
- antimicrobial compounds
- 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.)
- Active
Links
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention is suitable for the technical field of organic synthesis, and provides a preparation method of an anti-bacterial compound. The method comprises the following steps of: preparing organo-silicone containing tertiary amine; and preparing an anti-bacterial compound. The preparation method of the compound has the advantages of simple process, easiness in controlling conditions and industrializing, and convenience in using in a wide range.
Description
The application is applicant is the divisional application of the application for a patent for invention of 201010116533.8 in the application number that on January 26th, 2010 submits to, by reference its full content is attached to the application.
Technical field
The invention belongs to technical field of organic synthesis, particularly relate to a kind of antimicrobial compounds preparation method
Background technology
Bacterium or fungi infestation have become threat human health and the worldwide major issue enjoying global medical health protection to pay close attention to.Giving material or product surface anti-microbial property, to stop bacterium or fungi in its surface growth or breeding, even kill bacterium or the fungi on surface, is one of important means solving bacterium or fungi infestation.Current international anti-biotic material can be divided into four large classes: (1) inorganic antiseptic, such as nano titanium oxide, nanometer silver, Nanometer Copper, and their ion etc.(2) antiseptic-germicide is had, such as quaternary ammonium salt, thiazoles etc.; (3) polymer antibacterial agent, such as high molecular quaternary; (4) natural and modification antiseptic-germicide: as chitosan, Sorbic Acid.
Give material or product surface anti-microbial property the most frequently used be containing the coating of antiseptic-germicide (as nanometer silver, Nanometer Copper and their ion thereof or other antiseptic-germicides) at its surface-coated one deck, nanometer silver, Nanometer Copper and other heavy metals and heavy metal ion, rely in its slow releasing metal ion to surrounding environment and reach antibacterial or sterilization object, but along with the prolongation of duration of service, its anti-microbial activity reduces gradually, until finally completely lose its anti-microbial activity, also may make a variation by inducing microbial simultaneously, increase the probability producing resistance.In addition, the hazardness of nano material also gradually be familiar with by the mankind and pay close attention to.Organic antibacterial agent and its poor heat resistance of natural antibacterial agent, usually limit its use range.High molecular quaternary antiseptic-germicide can overcome the shortcomings such as volatile, difficult processing, the poor chemical stability of small molecules antiseptic-germicide, and anti-microbial activity is excellent, not easily infiltrates through human body skin, thus receives the concern of people.Such as a series of methyl acrylic ester high molecular quaternary antiseptic-germicide has been prepared by Fu Ruowen seminar [Reactive & functional polymers, 2007,67:355-366], and MIC is 1.56-20mg/mL.Polymkeric substance antiseptic-germicide main still Polymeric quaternary ammonium salts and polymkeric substance halogen amine antiseptic-germicide, its thermostability is also undesirable, and, in order to obtain good antiseptic-germicide, general requirement antiseptic-germicide is water miscible, also there is leachability and cause anti-microbial activity to lack persistence in these not immobilized polymer antibacterial agents, equally also can cause certain pressure to surrounding environment.As the people such as Lowe [J. Appl.Polym. Sci., 2006,101:1036-1041] prepare a series of polymkeric substance trimethyl-glycine antiseptic-germicide, its minimum inhibitory concentration (MIC) is 1125-2000ug/mL, exploitation for antiseptic-germicide proposes a kind of new thinking, can immobilized reactive functional groups but it does not have, keep away the shortcoming that its release property unavoidable runs off.
The antiseptic-germicide of this release property has the unfavorable factor of two aspects at least: the antiseptic-germicide that (1) implants has the ageing of release, lacks sustainable antimicrobial activity; (2) antiseptic-germicide discharged brings pressure to environment.These factors can not be ignored, and the antiseptic-germicide of the non-releasing micro of exploitation and preparation green is trend of the times.Material or product surface will be fixed on anti-microbial activity group with chemical bond form, material or goods sustainable antimicrobial activity can be given, nor cause in environment.Madkour [Langmuir, 2009,25:1060-1067] is with the surface reaction containing halosilanes and hydroxyl, the method of further employing atom transfer radical polymerization has prepared the layer of quick antibacterial, but complex process, condition is harsh, is difficult to industrialization.Saif [Langmuir, 2009,25:377-379] prepare the silicone Quaternary Ammonium Salt Antimicrobial Agent with sustainable antimicrobial activity, and the DC-5700 out of early stage DOW Corning company research and development belongs to this class, but the thermotolerance of the antiseptic-germicide of quaternary ammonium salt is bad, thus limit its use range.
How to overcome the shortcoming that current antiseptic-germicide field exists as previously discussed, research and develop a class new immobilizedly can have the new demand that long-lasting antiseptic-germicide is human social development.
Summary of the invention
The object of the present invention is to provide a kind of antimicrobial compounds preparation method, prepared compound can pass through response type functional group (silicon alkoxyl group) with chemical bonding mode securely with multiple material or Product Interface bonding, obtain lasting anti-microbial activity and wetting ability.
Silicone betaines type antimicrobial compounds prepared by the present invention, has general formula I:
Wherein, R
0=H, R
3x
R
1be selected from-CH
3, or-CH
2cH
3;
R
2be selected from-OR
1,-CH
3, or-CH
2cH
3;
R
3be selected from-(CH
2)
p, wherein p=1 ~ 10;
R
4-(CH
2)
qcH
3, wherein q=0 ~ 17, or R
4=H;
R
5-(CH
2)
qcH
3, wherein q=0 ~ 17, or R
5=H;
R
6be selected from-(CH
2)
rnH (CH
2)
t, wherein r, t=1 ~ 10, or-(CH
2)
u, wherein u=1 ~ 6;
Y is selected from-COO ,-SO
3.
In above-mentioned general formula I, substituent R
4with R
5identical group or different groups.
The invention provides the preparation method of above-mentioned antimicrobial compounds, its synthesis technique is simple, and condition is easy to control, and productive rate is high, is easy to suitability for industrialized production.
This object is achieved in that a kind of preparation method of antimicrobial compounds, the steps include:
Produce the organo-siloxane containing tertiary amine, and by this containing organo-siloxane of tertiary amine and reactant B under agitation, in the environment of temperature 10 ~ 80 DEG C sustained reaction 1 ~ 48h, obtain white sedimentable matter;
Above-mentioned white precipitate material is filtered or centrifugation, obtains silicone betaines type antimicrobial compounds, be i.e. obtained target product;
Above-mentioned reactant B is selected from propane sultone, butyl sultone, vinylformic acid, β-propiolactone, X (CH
2)
vsO
3 -, or X (CH
2)
vcO
2 -in one, wherein X is Br, Cl or I, v be more than or equal to 1 positive integer.
The typical synthetic route figure of above-mentioned preparation method is:
In above-mentioned preparation process, the preparation method wherein containing the organo-siloxane of tertiary amine is: get (R
1o)
2r
2siH and reactant A, at temperature 10 ~ 80 DEG C, under the effect of platinum group catalyst, carry out addition reaction of silicon with hydrogen, stirs, and reaction duration 1 ~ 48h, to obtain final product; Wherein R
1be selected from-CH
3or-CH
2cH
3, R
2be selected from-OR
1,-CH
3or-CH
2cH
3; Reactant A is the alkene containing tertiary amine, preferred DMAA or Diethyl Allylnime.
In above-mentioned preparation process, wherein said platinum group catalyst is selected from chloroplatinic acid catalyst, SiO
2loaded platinum catalyst, activated carbon supported type platinum catalyst or Karstedt type platinum catalyst.
In above-mentioned preparation process, the preparation method wherein containing the organo-siloxane of tertiary amine also can be: get (R
1o)
2r
2siR
3x and R
4r
5nH, at temperature 20 ~ 80 DEG C, adds NaOH/ aqueous isopropanol as catalyzer, and under agitation reacts duration 2 ~ 48h, to obtain final product; Wherein, R
1-CH
3or-CH
2cH
3; R
2-OR
1,-CH
3or-CH
2cH
3; R
3be selected from-(CH
2)
p, wherein p=1 ~ 10; R
4-(CH
2)
qcH
3, wherein q=0 ~ 17; R
5-(CH
2)
qcH
3, wherein q=0 ~ 17; X is Br, Cl or I.
Present invention also offers the another kind of preparation method of above-mentioned antimicrobial compounds, the steps include:
By containing aminosiloxane and reactant B under agitation, in the environment of temperature 10 ~ 80 DEG C sustained reaction 1 ~ 48h and silicone betaines type antimicrobial compounds, namely obtain target product
Similarly, above-mentioned reactant B is selected from propane sultone, butyl sultone, vinylformic acid, β-propiolactone, X (CH
2)
vsO
3 -, or X (CH
2)
vcO
2 -in one, wherein X is Br, Cl or I, v be more than or equal to 1 positive integer.
The advantage of technique scheme is: this antimicrobial compounds, there is reactive functional groups---siloxanes, can there is chemical bonding effect with multiple material interface in it, thus give by the material of antimicrobial compounds process or the lasting anti-microbial activity of goods and very strong wetting ability.Meanwhile, the synthesis technique of preparation method is simple, and condition easily controls, and is easy to industrialization, provides conveniently for it uses in broad range.In addition, this antimicrobial compounds also has the particular advantages such as acid-and base-resisting, salt, especially low, the chemical stability of toxicity and Heat stability is good, and the product surface through this antimicrobial compounds process can stand the various disinfection technology process commonly used.
Embodiment
In order to make object of the present invention, technical scheme and advantage clearly understand, below in conjunction with embodiment, the present invention is further elaborated.Should be appreciated that specific embodiment described herein only in order to explain the present invention, be not intended to limit the present invention.
Embodiment 1
Take 98.6g triethoxyl silane [(CH
3cH
2o)
3siH] join with mechanical stirring and reflux round-bottomed flask in, after adding the Platinic chloride/Isopropanol catalysis agent of 0.2ml, under stirring and 60 DEG C of temperature, slowly drip 51.2g DMAA [CH with dropping funnel
2=CHCH
2n (CH
3)
2], dropwise rear continuation reaction 1h, cool to 50 DEG C, then drip propane sultone [
, hereinafter referred to as 1,3-PS] and 73.2g(is dissolved in 400mL dehydrated alcohol), dropwise rear continuation reaction 1h, obtain white precipitation, centrifugation is purifying for several times, and obtain organosilicon sulfonate betaine antiseptic-germicide, its structural formula is: (CH
3cH
2o)
3si (CH
2)
3 +n (CH
3)
2(CH
2)
3sO
3 -, the minimum inhibitory concentration (MIC) of this antiseptic-germicide to intestinal bacteria (8099) and streptococcus aureus (ATCC6538) is 15mg/mL, and minimum bactericidal concentration (MBC) is 20mg/mL.
Embodiment 2
Take 107.8g methyldiethoxysilane [(CH
3cH
2o)
2cH
3siH] join with magnetic agitation and reflux Florence flask in, add 0.25g SiO
2after load type platinum Au catalyst, under magnetic agitation and 30 DEG C of temperature, slowly drip 88.9g Diethyl Allylnime [CH with dropping funnel
2=CHCH
2n (CH
2cH
3)
2], and start calculating reacting time, after reaction 8h, filtration under diminished pressure reclaims catalyzer, then collect filtrate, and in filtrate, drip 1,3-PS(of 97.6g be dissolved in 400mL dehydrated alcohol), reaction 10h is continued at 30 DEG C of temperature, obtain white precipitation, filter also with washing with alcohol purifying for several times, obtain organosilicon sulfonate betaine antiseptic-germicide.Its structural formula is: (CH
3cH
2o)
2siCH
3(CH
2cH
2)
3 +n (CH
3)
2(CH
2)
3sO
3 -, the MIC of this antiseptic-germicide to intestinal bacteria (8099) and streptococcus aureus (ATCC6538) is 25mg/mL, and MBC is 30mg/mL.
Embodiment 3
Take 107.6g methyldiethoxysilane [(CH
3cH
2o)
2cH
3siH] join with magnetic agitation and reflux Florence flask in, after adding the Karstedt type platinum catalyst of 0.20g, under magnetic stirring with 20 DEG C of temperature, slowly drip 68.2g DMAA [CH with dropping funnel
2=CHCH
2n (CH
3)
2], and starting calculating reacting time, after reaction 24h, filtration under diminished pressure reclaims catalyzer, then collects filtrate, and in filtrate, drips 93.2 sodium chloroacetate [ClCH
2cO
2na] (being dissolved in 400mL dehydrated alcohol), react 24h at 20 DEG C of temperature, obtain white precipitation, centrifugation is purifying for several times, obtains organosilicon carboxylic acid type trimethyl-glycine antiseptic-germicide.Its structural formula is: (CH
3cH
2o)
2siCH
3(CH
2)
3 +n (CH
3)
2cH
2cO
2 -, the MIC of this antiseptic-germicide to intestinal bacteria (8099) and streptococcus aureus (ATCC6538) is 20mg/mL, and MBC is 25mg/mL.
Embodiment 4
Take 107.6g methyldiethoxysilane [(CH
3cH
2o)
2cH
3siH] join with mechanical stirring and reflux round-bottomed flask in, after adding the activated carbon supported type platinum catalyst of 0.20g, under agitation with 50 DEG C of temperature, slowly drip 68.2g DMAA [CH with dropping funnel
2=CHCH
2n (CH
3)
2], dropwise rear continuation reaction 2h after filtration under diminished pressure reclaim catalyzer, then collect filtrate, and drip in filtrate 57.7g beta-propiolactone [
] (being dissolved in 400mL butanone), continue reaction 6h at 40 DEG C of temperature, obtain white precipitation, centrifugation is purifying for several times, obtains organosilicon carboxylic acid type trimethyl-glycine antiseptic-germicide.Its structural formula is: (CH
3cH
2o)
2siCH
3(CH
2)
3 +n (CH
3)
2(CH
2)
2cO
2 -, the MIC of this antiseptic-germicide to intestinal bacteria (8099) and streptococcus aureus (ATCC6538) is 10mg/mL, and MBC is 20mg/mL.
Embodiment 5
Take 142.5g N.N-diethyl-3-aminopropyl trimethoxysilane [(CH
3cH
2)
2n (CH
2)
3si (OCH
3)
3] join with magnetic agitation and reflux Florence flask in, slowly drip 1,3-PS(of 73.2g under magnetic stirring and be dissolved in 400mL acetone), after 10 DEG C of reaction 48h, obtain white precipitation, centrifugation is purifying for several times, obtains organosilicon sulfonate betaine antiseptic-germicide.Its structural formula is: (CH
3o)
3si (CH
2)
3 +n (CH
2cH
3)
2(CH
2)
3sO
3 -, the MIC of this antiseptic-germicide to intestinal bacteria (8099) and streptococcus aureus (ATCC6538) is 15mg/mL, and MBC is 20mg/mL.
Embodiment 6
Get 97.8g Trimethoxy silane [HSi (OCH
3)
3] join with mechanical stirring and reflux Florence flask in, after adding the activated carbon supported type platinum catalyst of 0.20g, under magnetic agitation and 50 DEG C of temperature, slowly drip 88.9g Diethyl Allylnime [CH with dropping funnel
2=CHCH
2n (CH
2cH
3)
2], stop heating after dropwising rear continuation reaction 2h, filtration under diminished pressure reclaims catalyzer, then collects filtrate, and drip the ClCH of 93.2g in filtrate
2cH
2sO
3na(is dissolved in 400mL dehydrated alcohol), be heated to 50 DEG C, continue reaction 10h, obtain white precipitation, filter and with absolute ethanol washing purifying for several times, obtain organosilicon sulfonate betaine antiseptic-germicide.Its structural formula is: (CH
3o)
3si (CH
2)
3 +n (CH
2cH
3)
2(CH
2)
2sO
3 -, the MIC of this antiseptic-germicide to intestinal bacteria (8099) and streptococcus aureus (ATCC6538) is 20mg/mL, and MBC is 25mg/mL.
Embodiment 7
Take 124.0g N-(β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane [NH
2(CH
2)
2nH (CH
2)
3siCH
3(OCH
3)
2] join with magnetic stirring apparatus and reflux Florence flask in, slowly drip 1 of 73.2g under magnetic stirring, 3-PS(is dissolved in 400mL dehydrated alcohol), after being heated to 40 DEG C of reaction 2h, obtain pale yellow oil organosilicon sulfonate betaine antiseptic-germicide.Its structural formula is: (CH
3o)
3si (CH
2)
3nH (CH
2)
2 +nH
2(CH
2)
3sO
3 -, the MIC of this antiseptic-germicide to intestinal bacteria (8099) and streptococcus aureus (ATCC6538) is 25mg/mL, and MBC is 30mg/mL.
Embodiment 8
Take 119.2g r-chloropropyl trimethoxyl silane [(CH
3o)
3siCH
2cH
2cH
2cl] join with mechanical stirrer and reflux round flask in, slowly drip 60.7g di-n-propylamine [(CH with dropping funnel under agitation with 80 DEG C of temperature
3cH
2cH
2)
2nH] (being dissolved in 200ml dehydrated alcohol), 30 DEG C are cooled to after dropwising rear continuation reaction 10h, drip 1 of 73.2g, 3-PS(is dissolved in 200mL dehydrated alcohol), continue reaction 10h, obtain white precipitation, centrifugation is purifying for several times, obtain organosilicon sulfonate betaine antiseptic-germicide, its structural formula is: (CH
3o)
3si (CH
2)
3 +n (CH
2cH
2cH
3)
2(CH
2)
3sO
3 -, the minimum inhibitory concentration (MIC) of this antiseptic-germicide to intestinal bacteria (8099) and streptococcus aureus (ATCC6538) is 15mg/mL, and minimum bactericidal concentration (MBC) is 20mg/mL.
By above-mentioned example products therefrom process glass surface, all obtain contact angle all lower than the ultra-hydrophilic surface of 10 degree, and adopt colony counting method to test its anti-microbial activity and sustainable antimicrobial activity, result is as shown in table 1.
The sustainable antimicrobial activity analysis (colony counting method) of the antiseptic-germicide of table 1 embodiment 1-8
In other preferred embodiment of the present invention, can select with the CH of suitable amount of substance
3cH
2(CH
3o)
2siH, CH
3cH
2(CH
3cH
2o)
2siH, CH
3(CH
3o)
2siH replaces (CH
3cH
2o)
3siH or (CH
3o)
3siH or (CH
3cH
2o)
2cH
3siH; Also can select with the butyl sultone of suitable amount of substance, vinylformic acid, X (CH
2)
vsO
3na or X (CH
2)
vcO
2na(wherein X is Br, Cl or I; V be more than or equal to 1 positive integer) replace propane sultone, beta-propiolactone, ClCH
2cO
2na or ClCH
2cH
2sO
3na.
Above-described is only several embodiment of the present invention; it describes comparatively concrete and detailed; therefore the restriction to the scope of the claims of the present invention can not be interpreted as; should be understood that; for the person of ordinary skill of the art; without departing from the inventive concept of the premise, can also make some other distortion and improvement, these all belong to protection scope of the present invention.
Claims (1)
1. a preparation method for antimicrobial compounds, the steps include:
By NH
2(CH
2)
2nH (CH
2)
3siCH
3(OCH
3)
2under agitation, temperature 40 DEG C react 2h with 1,3-PS, obtain pale yellow oil organosilicon sulfonate betaine antiseptic-germicide, the structural formula of described organosilicon sulfonate betaine antiseptic-germicide is: (CH
3o)
3si (CH
2)
3nH (CH
2)
2 +nH
2(CH
2)
3sO
3 -.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210377540.2A CN102924496B (en) | 2009-11-28 | 2010-01-26 | Method for preparing anti-bacterial compound |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910188570 | 2009-11-28 | ||
| CN2009101885707 | 2009-11-28 | ||
| CN200910188570.7 | 2009-11-28 | ||
| CN201210377540.2A CN102924496B (en) | 2009-11-28 | 2010-01-26 | Method for preparing anti-bacterial compound |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010101165338A Division CN101812086B (en) | 2009-11-28 | 2010-01-26 | Anti-bacterial compound and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102924496A CN102924496A (en) | 2013-02-13 |
| CN102924496B true CN102924496B (en) | 2015-04-22 |
Family
ID=47639449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210377540.2A Active CN102924496B (en) | 2009-11-28 | 2010-01-26 | Method for preparing anti-bacterial compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102924496B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103396550B (en) * | 2013-07-08 | 2015-11-18 | 上海师范大学 | A kind of preparation method of the order mesoporous organosilicon material of amphiphilic of imidazoles functionalization |
| CN107447524A (en) * | 2017-08-11 | 2017-12-08 | 深圳市尼森实业有限公司 | A kind of synthetic method of environmental type textile antibacterial finish agent |
| CN112210341B (en) * | 2020-09-18 | 2022-07-26 | 山东东岳有机硅材料股份有限公司 | Double-vulcanization system building sealant and preparation method thereof |
| CN113529209B (en) * | 2021-07-15 | 2023-01-03 | 杭州逸腾新材料有限公司 | Superfine denier porous polyester yarn and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5936703A (en) * | 1993-10-13 | 1999-08-10 | Nof Corporation | Alkoxysilane compound, surface processing solution and contact lens |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007146680A1 (en) * | 2006-06-06 | 2007-12-21 | Florida State University Research Foundation , Inc. | Stabilized silica colloid |
-
2010
- 2010-01-26 CN CN201210377540.2A patent/CN102924496B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5936703A (en) * | 1993-10-13 | 1999-08-10 | Nof Corporation | Alkoxysilane compound, surface processing solution and contact lens |
Non-Patent Citations (2)
| Title |
|---|
| Platinum Oxide (PtO2): A Potent Hydrosilylation Catalyst;Nicolas Sabourault et al.;《ORGANIC LETTERS》;20020604;第4卷(第13期);第2117页摘要，第2118页表1-2、左栏第1段 * |
| Proton-Conducting Solid Electrolyte via Ozonolysis of Cationic Ammonium Organoalkoxysilane Surfactant-Templated MCM-41;Christopher A. Alabi et al.;《Chem. Mater.》;20061031;第18卷(第24期);第5635页表1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102924496A (en) | 2013-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101812086B (en) | Anti-bacterial compound and preparation method thereof | |
| CN102924496B (en) | Method for preparing anti-bacterial compound | |
| CN104177573B (en) | A kind of quaternary ammonium salt-fluorine silica acrylic acid ester block copolymer and preparation method and application are in antimicrobial coating material | |
| US6482912B2 (en) | Method of preparing aminofunctional alkoxy polysiloxanes | |
| AU2004243046B2 (en) | Antimicrobial quaternary ammonium organosilane coatings | |
| KR101015932B1 (en) | Antibiotic composition and preparation method thereof | |
| CN107880206A (en) | A kind of long-lasting antibacterial water-based acrylic resin and preparation method thereof | |
| JP2008074917A5 (en) | ||
| CN102020672B (en) | Alkoxy silicane functionalized betaine zwitterionic compound and preparation method and application thereof | |
| CN104817847A (en) | Antibacterial organic silicone elastomer emulsion, preparation method and application thereof | |
| CN101812153B (en) | Waterborne antibacterial styrene-acrylate emulsion and preparation method thereof | |
| CN106831850A (en) | A kind of hydrosilylation | |
| CN104788487A (en) | Hydrolysis resistant Si-C-Si type cation organosilicon surfactant | |
| CN105733268A (en) | Mouldproof antibacterial polyorganosiloxane sealing material and preparation method thereof | |
| CN114592348A (en) | Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric | |
| CN110776528A (en) | Ammonium sulfonate zwitterionic silane coupling agent, siloxane ring body and preparation method thereof | |
| KR100297953B1 (en) | Silane Coupling Reagent and Preparation Method Thereof | |
| CN111072707B (en) | Multifunctional bactericidal compound and preparation method and application thereof | |
| CN114592352B (en) | Hydrophilic antibacterial finishing agent and preparation method and application thereof | |
| CN101885707A (en) | Triazine derivative and preparation method thereof as well as new application as insecticide | |
| JP2008031337A5 (en) | ||
| KR101249352B1 (en) | Alkylalkoxysilane compounds containing ether group and dialkylamino group and process for preparing the compounds | |
| CN110157294A (en) | A kind of antibacterial powder paint | |
| CN102690481B (en) | A kind of Composite antimicrobial of nanometer silver bromide polymer and preparation method thereof | |
| CN113234017A (en) | Imidazole salt compound with antibacterial effect and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20210623 Address after: 518000 18-c, unit 2, building 5, Haojing City, No.8, democracy Avenue, Ho Township Community, Shajing street, Bao'an District, Shenzhen City, Guangdong Province Patentee after: Haisi Meiyu (Shenzhen) Technology Co.,Ltd. Address before: 518000 No. 3688 Nanhai Road, Shenzhen, Guangdong, Nanshan District Patentee before: SHENZHEN University |
|
| TR01 | Transfer of patent right |