CN101270281A - Method for preparing hydrophobic dyes doping silicon dioxide nano-particle - Google Patents
Method for preparing hydrophobic dyes doping silicon dioxide nano-particle Download PDFInfo
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- CN101270281A CN101270281A CNA200810050703XA CN200810050703A CN101270281A CN 101270281 A CN101270281 A CN 101270281A CN A200810050703X A CNA200810050703X A CN A200810050703XA CN 200810050703 A CN200810050703 A CN 200810050703A CN 101270281 A CN101270281 A CN 101270281A
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Abstract
The invention provides a preparation method of silicon dioxide nano particles mixed with a hydrophobic dye, and belongs to the field of luminescent nano material. A surfactant is used to form micelles which are used for dispersing the hydrophobic dye in reaction solution uniformly; silicon dioxide nano particles are formed through the hydrolization and the condensation of organosilicon; the micelles, in with the hydrophobic dye is dissolved, is involved in the formation of silicon dioxide nano particles, thus preparing the silicon dioxide nano particles mixed with the hydrophobic dye. The process of the preparation method is simple; the cost is low; the mixing efficiency is high; the pollution resulting from organic solvents in the microemulsion method is avoided; the dye is effectively prevented from leaking during postprocessing and depositing because of strong interaction; the resultant luminescent nano particles are monodisperse and are uniform in size; the dye is mixed uniformly among different particles with high chemical stability and colloid stability; the particles can be applied in the fields of biological detectors, markers, biological sensors and so on after the surfaces of the particles are further functionalized.
Description
Technical field
The invention belongs to Illuminant nanometer material technology field, particularly a kind of preparation method of hydrophobic dyes doping silicon dioxide nano-particle.
Background technology
Recently, dyes doping silicon dioxide nano-particle has replaced organic dye to be widely used in every field such as optical research, environmental sensor and bioprobe owing to have better light stability and the advantages such as surface of easy functionalization.But organic light emission dyestuff great majority are hydrophobic dyes, can't be compound with hydrophilic silicon-dioxide, and therefore, the dyestuff kind that can be widely used at present is less, and price is very expensive, has limited the development of dyes doping silicon dioxide nano-particle greatly.So inventing a kind of simple effective method is the matter of utmost importance that faces solution in the practical application with hydrophobic dyes doping in Nano particles of silicon dioxide, also be the needs of expanding the dyes doping silicon dioxide nano-particle kind.
In the past few years, people have adopted phospholipid molecule, multipolymer polymer and various tensio-active agent to form the oil phase template, construct the silicon dioxide granule with hydrophobic inner structure, to help the doping (J.Am.Chem.Soc. of hydrophobic dye, 2002,124,6037; Science, 2002,297,967; Science, 1999,285,1049; J.Am.Chem.Soc., 2002,124,8307; Anal.Chim.Acta, 2003,481,181).Wherein the most extensive and sophisticated method is oil-in-water (O/W) microemulsion method, utilize tensio-active agent in pure water or profit mixing solutions, can form microemulsion, these microemulsion structures can provide stabile microenvironment for guest molecule, help guest molecule and be doped to (Anal.Chem. in the host matrix, 2001,73,4988; Chem.Commum., 2004,2801; Anal.Biochem., 2004,334,135).Yet microemulsion method must be used a large amount of organic solvents in building-up process, and the aftertreatment of particle is more loaded down with trivial details and be difficult for eliminating.Simultaneously, they find because hydrophobic dye and silicon-dioxide lack strong interaction force, thereby are easy to leak from the duct of silicon-dioxide.Simultaneously, resulting in this way particle is because the serious gathering of dye inside makes the luminous intensity of particle weaken greatly.
Summary of the invention
The technical problem to be solved in the present invention is, at the easy shortcoming such as leakage of complex steps in the existing preparation hydrophobic dyes doping silicon dioxide nano-particle method, seriously polluted, dyestuff, invented a kind of simple and effective preparation method, isolation owing to micellar structure in the resulting particle makes dyestuff to disperse equably, thereby obtain very high luminous intensity, greatly satisfy requirement of actual application.
Technical scheme of the present invention is:
A kind of preparation method of hydrophobic dyes doping silicon dioxide nano-particle has tensio-active agent to induce micelle formation, dissolving, the hydrolysis in organosilicon source and the technological process that condensation form Nano particles of silicon dioxide of hydrophobic dye in micella; Said tensio-active agent is induced micelle formation, is to be that 1～29 mixing solutions is a solvent by volume with the second alcohol and water, cats product or the organo silane coupling agent that has a hydrophobic long-chain is dissolved in solvent by 0.13～3.74g/L concentration forms micella; The dissolving of said hydrophobic dye in micella is that hydrophobic dye is dissolved in the solvent by 0.01～0.07g/L concentration; It is tetraethoxy to be joined in the solvent that source hydrolysis of said organosilicon and condensation form Nano particles of silicon dioxide again, is undertaken by hydrolysis and condensation reaction under the ammonification water condition.
Among the preparation method of above-mentioned hydrophobic dyes doping silicon dioxide nano-particle, said hydrophobic dye, be meant non-polar dyes molecule that has long alkyl chain or substituted benzene or organic dye with last conversion character, dyestuff is luminous to be that its emission peak position of phosphorescence or fluorescence is between 460～730nm, between 0.01～0.07g/L, the hydrophobic dye molecule enters micella inside by the affinity with the micella hydrophobic inner core to its add-on by solvent.
Induce in the micelle formation process at tensio-active agent, said cats product can be the derivative of organic amine, comprise cetyl trimethylammonium bromide, the inferior methoxyl group ammonia bromide of dodecyl dimethoxy benzene, distearyl dimethyl ammonium chloride, or easily protonated benzene homologue, comprise the hexadecyl pyridine bromide.The micella that cats product forms has positive charge, can with electronegative silica monomer generation electrostatic adsorption.The said organo silane coupling agent that has hydrophobic long-chain comprises octadecyl Trimethoxy silane, hexadecyl Trimethoxy silane, three silyloxy carbon tridecyl polyethylene oxide or dodecyl Trimethoxy silanes.Organo silane coupling agent one end that has a hydrophobic long-chain have the hydrophobicity carbochain the other end have can hydrolysis siloxanes, the silica that forms after the hydrolysis is born the group possess hydrophilic property, can play with the same effect of tensio-active agent and the negative group of silica can with the condensation reaction of teos hydrolysis monomer generation covalency.Tensio-active agent of selecting for use or the organo silane coupling agent that has hydrophobic long-chain are dissolved in by solvent 0.13～3.74g/L in the mixing solutions of second alcohol and water, can form the spherical micelle that is of a size of 2～6nm.
Form in the technological process of Nano particles of silicon dioxide in hydrolysis of organosilicon source and condensation, source hydrolysis of said organosilicon and condensation form Nano particles of silicon dioxide, be meant that the volumetric molar concentration of ammoniacal liquor is counted 0.98～3.92mol/L by solvent in the reaction soln, temperature of reaction is between 20～40 ℃, add tetraethoxy under the stirring velocity of 200～600rpm, add total amount and count 20～67ml/L, reacted 9～18 hours by solvent.
Tetraethoxy also can be 2～4 batches of addings of branch.The add-on that tetraethoxy is every batch is counted 10～33.7ml/L by solvent, and the timed interval of adjacent twice adding is 3～6 hours, after tetraethoxy all adds, continues reaction 6～12 hours again.
The content of dyestuff reaches 0.05～0.01% in the hydrophobic dyes doping silicon dioxide nano-particle that obtains, and particle is monodisperse sphere, and particle diameter is between 50～600nm.
The micella that the inventive method is utilized positively charged ion or had the organo silane coupling agent that has hydrophobic long-chain to form in solution, the hydrophobic dye molecule is fixed in the micellar hydrophobic inner core, not only hydrophobic dye had solubilising, and can with the hydrolysis monomer of tetraethoxy or the silicon matrix generation electrostatic adhesion or the covalent effect of generation, thereby be doped in the Nano particles of silicon dioxide.This strong interaction guarantees that dyestuff can not leak from silicon-dioxide, have higher chemistry and optical stability.Owing to effective isolation of micellar structure, high density is dye adulterated fluorescent quenching can not to take place, and keeps high luminous intensity simultaneously.
The preparation method of hydrophobic dyes doping silicon dioxide particle of the present invention utilizes micella solubilising principle to hydrophobic dye in polar solvent dexterously, need not a large amount of organic cosolvents, makes that pollution is little and doping efficiency is high, the simple cost of technology is low.The incandescnet particle that finally obtains is monodispersity, and particle diameter is even, dye adulterated amount homogeneous between the different particles, and chemistry and colloidal stability are good, and the surface is easy to further functionalization simultaneously, can be widely used in the every field of industry.
Specific embodiments
Embodiment 1
In the 100ml there-necked flask, add 24 milliliters of ethanol, volume ratio according to ethanol and water is 4: 1 adding 6 ml waters, add tensio-active agent cetyl trimethylammonium bromide 0.0039 gram, add hydrophobic dye benzothiazolyl octadecane oxygen basic note legumin 0.0008 gram, ammoniacal liquor 2ml, 40 ℃ of stirring in water bath, stirring velocity 200rpm, add tetraethoxy 0.4ml, react and add tetraethoxy 0.4ml again after 3 hours, continue to react 6 hours.
Embodiment 2
In the 100ml there-necked flask, add 15 milliliters of ethanol, volume ratio according to ethanol and water is 1: 1 adding 15 ml water, add organo silane coupling agent octadecyl Trimethoxy silane 0.008 gram that has hydrophobic long-chain, add hydrophobic dye benzothiazolyl octadecane oxygen basic note legumin 0.0008 gram, ammoniacal liquor 1ml, 25 ℃ of stirring in water bath, stirring velocity 400rpm, add 0.5 milliliter of tetraethoxy again, react and add 0.5 milliliter of tetraethoxy after 6 hours again, continue reaction 10 hours.
Embodiment 3
In the 100ml there-necked flask, add 15 milliliters of ethanol, volume ratio according to ethanol and water is 1: 1 adding 15 ml water, add tensio-active agent cetyl trimethylammonium bromide gram 0.012 gram, add hydrophobic dye benzothiazolyl octadecane oxygen basic note legumin 0.0008 gram, 0.5 milliliter of ammoniacal liquor, 20 ℃ of stirring in water bath, stirring velocity 400rpm, add 1.01 milliliters of tetraethoxys again, react and add 1 milliliter of tetraethoxy after 6 hours again, continue reaction 6 hours.
Embodiment 4
In the 100ml there-necked flask, add 29 milliliters of ethanol, volume ratio according to ethanol and water is 29: 1 adding 1 ml waters, add organo silane coupling agent hexadecyl Trimethoxy silane 0.112 gram that has hydrophobic long-chain, add two pyridine derivate 0.002 grams of hydrophobic dye, 1.0 milliliters of ammoniacal liquor, 25 ℃ of stirring in water bath, stirring velocity 200rpm, add 0.3 milliliter of tetraethoxy again, react and add 0.3 milliliter of tetraethoxy after 6 hours again, continue reaction 6 hours.
Embodiment 5
In the 100ml there-necked flask, add 29 milliliters of ethanol, volume ratio according to ethanol and water is 29: 1 adding 1 ml waters, add organo silane coupling agent three silyloxy carbon tridecyl polyethylene oxides 0.1122 gram that has hydrophobic long-chain, add hydrophobic dye rhodamine B 0.0021 gram, 1.6 milliliters of ammoniacal liquor, 30 ℃ of stirring in water bath, stirring velocity 200rpm, add 0.3 milliliter of tetraethoxy again, reacted 6 hours, add 0.1 milliliter of tetraethoxy again, reacted 3 hours, add 0.1 milliliter of tetraethoxy again, react and add 0.1 milliliter of tetraethoxy after 3 hours again, continue reaction 6 hours.
Embodiment 6
In the 100ml there-necked flask, add 29 milliliters of ethanol, volume ratio according to ethanol and water is 29: 1 adding 1 ml waters, add organo silane coupling agent octadecyl Trimethoxy silane 0.112 gram that has hydrophobic long-chain, add hydrophobic dye rhodamine B 0.002 gram, 1.6 milliliters of ammoniacal liquor, 30 ℃ of stirring in water bath, stirring velocity 200rpm, add 0.3 milliliter of tetraethoxy again, react and add 0.3 milliliter of tetraethoxy after 6 hours again, continue reaction 12 hours.
Embodiment 7
In the 100ml there-necked flask, add 15 milliliters of ethanol, volume ratio according to ethanol and water is 1: 1 adding 15 ml water, add organo silane coupling agent octadecyl Trimethoxy silane alkane 0.057 gram that has hydrophobic long-chain, add hydrophobic dye benzothiazolyl octadecane oxygen basic note legumin 0.0003 gram, 0.8 milliliter of ammoniacal liquor, 40 ℃ of stirring in water bath, stirring velocity 600rpm, add 0.3 milliliter of tetraethoxy again, react and add 0.3 milliliter of tetraethoxy after 6 hours again, continue reaction 12 hours.
Embodiment 8
Use the inferior methoxyl group ammonia bromide of dodecyl dimethoxy benzene, distearyl dimethyl ammonium chloride, hexadecyl pyridine bromide, carbon dodecyl Trimethoxy silane etc. instead and make tensio-active agent, remaining is identical with embodiment 1～7, also can prepare hydrophobic dyes doping silicon dioxide nano-particle.
Use 2 instead, 7-dichloro-dihydro fluorescein diacetate, 5-MOP, umbelliferone, 3,4-dimethyl tonka bean camphor, 4-phenmethyl-7-cumarone, dansyl diamine, 1-methyl pyrene, dactinomycin etc. are made dyestuff, remaining is identical with embodiment 1～7, also can prepare various dyes doping silicon dioxide nano-particles.
Claims (5)
1, a kind of preparation method of hydrophobic dyes doping silicon dioxide nano-particle has tensio-active agent to induce micelle formation, dissolving, the hydrolysis in organosilicon source and the technological process that condensation form Nano particles of silicon dioxide of hydrophobic dye in micella; Said tensio-active agent is induced micelle formation, is to be that 1～29 mixing solutions is a solvent by volume with the second alcohol and water, cats product or the organo silane coupling agent that has a hydrophobic long-chain is dissolved in solvent by 0.13～3.74g/L concentration forms micella; The dissolving of said hydrophobic dye in micella is that hydrophobic dye is dissolved in the solvent by 0.01～0.07g/L concentration; It is that tetraethoxy is joined in the solvent that source hydrolysis of said organosilicon and condensation form Nano particles of silicon dioxide, is undertaken by hydrolysis and condensation reaction under the ammonification water condition.
2, according to the preparation method of the described a kind of hydrophobic dyes doping silicon dioxide nano-particle of claim 1, it is characterized in that, said hydrophobic dye, be the organic dye that has the non-polar dyes molecule of long alkyl chain or substituted benzene or have last conversion character, dyestuff is luminous to be that its emission peak position of phosphorescence or fluorescence is between 460-730nm; Said cats product, it is the derivative of organic amine, comprise cetyl trimethylammonium bromide, the inferior methoxyl group ammonia bromide of dodecyl dimethoxy benzene, distearyl dimethyl ammonium chloride, or easily protonated benzene homologue, comprise the hexadecyl pyridine bromide; The said organo silane coupling agent that has hydrophobic long-chain is octadecyl Trimethoxy silane, hexadecyl Trimethoxy silane, three silyloxy carbon tridecyl polyethylene oxide or dodecyl Trimethoxy silanes.
3, according to the preparation method of claim 1 or 2 described a kind of hydrophobic dyes doping silicon dioxide nano-particles, it is characterized in that, source hydrolysis of said organosilicon and condensation form Nano particles of silicon dioxide, be in the reaction soln, the volumetric molar concentration of ammoniacal liquor is counted 0.98～3.92mol/L by solvent, and temperature of reaction adds tetraethoxy under the stirring velocity of 200～600rpm between 20～40 ℃, add total amount and count 20～67ml/L, reacted 9～18 hours by solvent.
According to the preparation method of the described a kind of hydrophobic dyes doping silicon dioxide nano-particle of claim 3, it is characterized in that 4, said adding tetraethoxy is 2～4 batches of addings of branch; Every batch add-on is counted 10～33.7ml/L by solvent, and the timed interval of adjacent twice adding is 3～6 hours, after tetraethoxy all adds, continues reaction 6～12 hours again.
5, according to the preparation method of claim 1,2 or 4 described a kind of hydrophobic dyes doping silicon dioxide nano-particles, it is characterized in that, the content of dyestuff reaches 0.05～0.01% in the hydrophobic dyes doping silicon dioxide nano-particle, particle is monodisperse sphere, and particle diameter is between 50～600nm.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101768437B (en) * | 2010-01-19 | 2012-12-26 | 无锡中德伯尔生物技术有限公司 | SiO2 nano-particle taking positive electrical polyelectrolyte as template and doped with negative electricity dye and preparation method thereof |
| CN105419784A (en) * | 2015-12-11 | 2016-03-23 | 吉林大学 | Preparation method of ethyl-alcohol-sensitive 9,10-(diphenyl)-acetenyl-anthracene-doped silicon dioxide nanoparticles |
| CN107098353A (en) * | 2017-04-10 | 2017-08-29 | 温州大学 | A kind of colored thorn-like silica spheres and preparation method thereof |
| CN109439723A (en) * | 2018-11-30 | 2019-03-08 | 王瑞明 | A kind of toxotest method of multi-layer nano compound particle |
| CN109591133A (en) * | 2019-02-21 | 2019-04-09 | 浙江农林大学 | A kind of wood bamboo material hydrophobic modifier and its application |
| CN110455758A (en) * | 2019-08-13 | 2019-11-15 | 北京邮电大学 | A kind of fluorescence nano sensor and preparation method thereof of pH sensitivity |
| CN111484842A (en) * | 2020-03-13 | 2020-08-04 | 大连理工大学 | Fluorescent silica nanoparticles with nano hydrophobic cage structure and preparation method and application thereof |
| CN112076729A (en) * | 2020-09-15 | 2020-12-15 | 西南石油大学 | Preparation method of long-chain saturated alkane silane-loaded silicon dioxide adsorbent |
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2008
- 2008-05-12 CN CNA200810050703XA patent/CN101270281A/en active Pending
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| CN101768437B (en) * | 2010-01-19 | 2012-12-26 | 无锡中德伯尔生物技术有限公司 | SiO2 nano-particle taking positive electrical polyelectrolyte as template and doped with negative electricity dye and preparation method thereof |
| CN105419784A (en) * | 2015-12-11 | 2016-03-23 | 吉林大学 | Preparation method of ethyl-alcohol-sensitive 9,10-(diphenyl)-acetenyl-anthracene-doped silicon dioxide nanoparticles |
| CN105419784B (en) * | 2015-12-11 | 2017-06-23 | 吉林大学 | The preparation method of alcohol sensible 9,10 (diphenyl) acetenyl anthracene doped Nano particles of silicon dioxide |
| CN107098353B (en) * | 2017-04-10 | 2020-01-31 | 温州大学 | flower-shaped silicon dioxide balls and preparation method thereof |
| CN107098353A (en) * | 2017-04-10 | 2017-08-29 | 温州大学 | A kind of colored thorn-like silica spheres and preparation method thereof |
| CN109439723A (en) * | 2018-11-30 | 2019-03-08 | 王瑞明 | A kind of toxotest method of multi-layer nano compound particle |
| CN109591133A (en) * | 2019-02-21 | 2019-04-09 | 浙江农林大学 | A kind of wood bamboo material hydrophobic modifier and its application |
| CN110455758A (en) * | 2019-08-13 | 2019-11-15 | 北京邮电大学 | A kind of fluorescence nano sensor and preparation method thereof of pH sensitivity |
| CN110455758B (en) * | 2019-08-13 | 2023-12-26 | 北京邮电大学 | PH-sensitive fluorescent nano sensor and preparation method thereof |
| CN111484842A (en) * | 2020-03-13 | 2020-08-04 | 大连理工大学 | Fluorescent silica nanoparticles with nano hydrophobic cage structure and preparation method and application thereof |
| CN112076729A (en) * | 2020-09-15 | 2020-12-15 | 西南石油大学 | Preparation method of long-chain saturated alkane silane-loaded silicon dioxide adsorbent |
| CN115595810A (en) * | 2022-11-10 | 2023-01-13 | 东莞市伊时针织印花有限公司（Cn） | Cationic dye for artificial fiber and preparation method thereof |
| CN115595810B (en) * | 2022-11-10 | 2024-01-02 | 东莞市伊时针织印花有限公司 | Cationic dye for artificial fiber and preparation method thereof |
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