CN106700086B - A kind of preparation method for the polymer brush can be used for chemical-biological sensing - Google Patents
A kind of preparation method for the polymer brush can be used for chemical-biological sensing Download PDFInfo
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- CN106700086B CN106700086B CN201611024970.0A CN201611024970A CN106700086B CN 106700086 B CN106700086 B CN 106700086B CN 201611024970 A CN201611024970 A CN 201611024970A CN 106700086 B CN106700086 B CN 106700086B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/574—Immunoassay; Biospecific binding assay; Materials therefor for cancer
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Abstract
The invention discloses a kind of preparation methods of polymer brush that can be used for chemical-biological sensing, polyvinyl alcohol tetrazole is prepared it is characterized in that polyacrylonitrile is reacted with sodium azide by click chemistry, polyvinyl alcohol tetrazole is reacted with methacrylate based polymers, product is dialysed, is freeze-dried, and polymer brush is obtained.The amplification of carcinomebryonic antigen detection signal is successfully realized by the polymer brush that preparation method disclosed in this invention obtains, lowest detection is limited to 0.1 pg/ml.
Description
Technical field
The present invention relates to a kind of preparation method of polymer brush, specifically a kind of polymer that can be used for chemical-biological sensing
The preparation method of brush, belongs to functional polymer material field.
Background technique
In recent years, as the continuous of urbanization process is accelerated and the rapid raising of industrialized level, the problem of environmental pollution
It is further prominent.Adverse effect brought by environmental pollution makes tumor incidence cumulative year after year.The early detection and diagnosis of tumour
It is prevented and treated most important.
Polymer brush is a kind of polymer containing big molecule side chain, in recent years because of its unique structure feature and before applying
Scape causes the extensive research interest of scholars.The appearance of click chemistry and after successfully referring to the field of polymers, because it has
Have the advantages that reaction condition is mild, rate is fast, high-efficient, rapidly becomes a kind of important means for preparing polymer brush.
Detection antibody is connected in polymer brush main chain terminal, design can be used for signal amplification combination containing multiple on side chain
Monomer, and it is polymer brush is immobilized to compound is formed on the carriers such as nanogold, increase signal output exponentially.
Therefore, it quickly and efficiently prepares the compound that polymer brush is constructed and the signal amplification for being used for tumor-marker analyte detection has
Significance.
Summary of the invention
It is an object of the present invention to provide a kind of preparation methods of polymer brush that can be used for chemical-biological sensing.
The present invention provides a kind of preparation methods of polymer brush that can be used for chemical-biological sensing, include the following steps:
Using the chain transfer agents containing carboxyl, obtaining end group by reversible addion-fragmentation chain transfer free radical polymerization is
Then the polyacrylonitrile of carboxyl is added in n,N-Dimethylformamide with sodium azide, ammonium chloride, stirs evenly, is placed in 120
Click chemistry reaction is carried out under degrees celsius, reaction carries out at least 12 hours, wherein the quality of polyacrylonitrile and sodium azide
Than for 1:1 ~ 20:1, the mass ratio of ammonium chloride and sodium azide is 1:1, and product is through cooling, hydrochloric acid acidification, separation, vacuum drying
Polyvinyl alcohol tetrazole is obtained, the methacrylate then obtained by polyvinyl alcohol tetrazole and by atom transfer radical polymerization
Quasi polymer and triethylamine are added in n,N-Dimethylformamide, are stirred evenly, and are placed under 65 degrees celsius and are carried out instead
It answers, reaction at least carries out 3 hours, and wherein the mass ratio of polyacrylonitrile and methacrylic polymer is 1:1 ~ 1:5, triethylamine
Mass ratio with methacrylic polymer is 1:1, and product obtains polymer brush through cooling, dialysis, freeze-drying.
Compared with the prior art the present invention has the advantage that the preparation method of polymer brush provided by the invention is easy easily
Row, by the adjusting to polyacrylonitrile and sodium azide dosage, can control the grafting density of polymer brush, resulting polymer
Brush be applied to tumor markers detection, be successfully realized carcinomebryonic antigen survey signal amplification, lowest detection be limited to 0.1 pik/
Milliliter.
Specific embodiment:
The following detailed description of the present invention and provide several embodiments:
Embodiment one:
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acid dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added
Enter into the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stir evenly, it is small to be placed in reaction 4 under 75 degrees celsius
When, product obtains polyacrylonitrile through precipitating, suction filtration, vacuum drying, by 2.0 milliliters of glycidyl methacrylate, 0.0223
Milliliter 2- isobutyl ethyl bromide, 0.0338 gram of copper bromide, 0.0322 milliliter of pentamethyl-diethylenetriamine, 0.0266 gram of ascorbic acid
It is added in the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stirs evenly, be placed under 65 degrees celsius and react 6
Hour, product obtains poly (glycidyl methacrylate) through cooling, dialysis, freeze-drying, by 0.5 gram of polyacrylonitrile, 0.5 gram
Sodium azide, 0.5 gram of ammonium chloride will enter into the ampoule bottle equipped with 5.0 milliliters of n,N-Dimethylformamide, stir evenly, set
It is reacted 12 hours under 120 degrees celsius, product obtains polyvinyl four through cooling, hydrochloric acid acidification, separation, vacuum drying
Azoles, 0.5 gram of polyvinyl alcohol tetrazole, 0.5 gram of poly (glycidyl methacrylate), 0.68 milliliter of triethylamine are added to equipped with 3.0
In the ampoule bottle of milliliter n,N-Dimethylformamide, stirs evenly, be placed under 65 degrees celsius and react 3 hours, product object warp
Cooling, dialysis, freeze-drying obtain polymer brush.The compound that resulting polymers brush and nanogold are constructed is applied to carcinomebryonic antigen
Detection, lowest detection is limited to 0.16 pg/ml.
Embodiment two:
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acid dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added
Enter into the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stir evenly, it is small to be placed in reaction 4 under 75 degrees celsius
When, product obtains polyacrylonitrile through precipitating, suction filtration, vacuum drying, by 2.0 milliliters of glycidyl methacrylate, 0.0223
Milliliter 2- isobutyl ethyl bromide, 0.0338 gram of copper bromide, 0.0322 milliliter of pentamethyl-diethylenetriamine, 0.0266 gram of ascorbic acid
It is added in the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stirs evenly, be placed under 65 degrees celsius and react 6
Hour, product obtains poly (glycidyl methacrylate) through cooling, dialysis, freeze-drying, by 0.5 gram of polyacrylonitrile, 0.05
Gram sodium azide, 0.05 gram of ammonium chloride will enter into the ampoule bottle equipped with 5.0 milliliters of n,N-Dimethylformamide, stir evenly,
It is placed under 120 degrees celsius and reacts 12 hours, product obtains polyvinyl four through cooling, hydrochloric acid acidification, separation, vacuum drying
Azoles, 0.5 gram of polyvinyl alcohol tetrazole, 0.5 gram of poly (glycidyl methacrylate), 0.68 milliliter of triethylamine are added to equipped with 3.0
In the ampoule bottle of milliliter n,N-Dimethylformamide, stirs evenly, be placed under 65 degrees celsius and react 3 hours, product object warp
Cooling, dialysis, freeze-drying obtain polymer brush.The compound that resulting polymers brush and nanogold are constructed is applied to carcinomebryonic antigen
Detection, lowest detection is limited to 0.34 pg/ml.
Embodiment three:
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acid dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added
Enter into the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stir evenly, it is small to be placed in reaction 4 under 75 degrees celsius
When, product obtains polyacrylonitrile through precipitating, suction filtration, vacuum drying, by 2.0 milliliters of glycidyl methacrylate, 0.0223
Milliliter 2- isobutyl ethyl bromide, 0.0338 gram of copper bromide, 0.0322 milliliter of pentamethyl-diethylenetriamine, 0.0266 gram of ascorbic acid
It is added in the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stirs evenly, be placed under 65 degrees celsius and react 6
Hour, product obtains poly (glycidyl methacrylate) through cooling, dialysis, freeze-drying, by 0.5 gram of polyacrylonitrile, 0.5 gram
Sodium azide, 0.5 gram of ammonium chloride will enter into the ampoule bottle equipped with 5.0 milliliters of n,N-Dimethylformamide, stir evenly, set
It is reacted 12 hours under 120 degrees celsius, product obtains polyvinyl four through cooling, hydrochloric acid acidification, separation, vacuum drying
Azoles, 0.5 gram of polyvinyl alcohol tetrazole, 1.0 grams of poly (glycidyl methacrylate)s, 1.36 milliliters of triethylamines are added to equipped with 3.0
In the ampoule bottle of milliliter n,N-Dimethylformamide, stirs evenly, be placed under 65 degrees celsius and react 3 hours, product object warp
Cooling, dialysis, freeze-drying obtain polymer brush.The compound that resulting polymers brush and nanogold are constructed is applied to carcinomebryonic antigen
Detection, lowest detection is limited to 0.16 pg/ml.
Example IV:
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acid dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added
Enter into the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stir evenly, it is small to be placed in reaction 4 under 75 degrees celsius
When, product obtains polyacrylonitrile through precipitating, suction filtration, vacuum drying, by 2.0 milliliters of hydroxyethyl methacrylates, 0.0204 milliliter
2- isobutyl ethyl bromide, 0.0310 gram of copper bromide, 0.0294 milliliter of pentamethyl-diethylenetriamine, 0.0243 gram of ascorbic acid are added
Into the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stirs evenly, is placed under 65 degrees celsius and reacts 6 hours,
Product obtains poly hydroxy ethyl acrylate through cooling, dialysis, freeze-drying, by 0.5 gram of polyacrylonitrile, 0.5 gram of sodium azide,
0.5 gram of ammonium chloride will enter into the ampoule bottle equipped with 5.0 milliliters of n,N-Dimethylformamide, stirs evenly, it is Celsius to be placed in 120
It is reacted 12 hours under the conditions of degree, product obtains polyvinyl alcohol tetrazole through cooling, hydrochloric acid acidification, separation, vacuum drying, and 0.5 gram poly-
Vinyl tetrazolium, 0.5 gram of poly (glycidyl methacrylate), 0.68 milliliter of triethylamine are added to equipped with 3.0 milliliters of N, N- bis-
In the ampoule bottle of methylformamide, stir evenly, be placed under 65 degrees celsius and react 3 hours, product object through cooling, dialysis,
Freeze-drying obtains polymer brush.The compound that resulting polymers brush and graphene oxide are constructed is applied to the inspection of carcinomebryonic antigen
It surveys, lowest detection is limited to 1.4 pg/mls.
Embodiment five:
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acid dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added
Enter into the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stir evenly, it is small to be placed in reaction 4 under 75 degrees celsius
When, product obtains polyacrylonitrile through precipitating, suction filtration, vacuum drying, by 2.0 milliliters of hydroxyethyl methacrylates, 0.0204 milliliter
2- isobutyl ethyl bromide, 0.0310 gram of copper bromide, 0.0294 milliliter of pentamethyl-diethylenetriamine, 0.0243 gram of ascorbic acid are added
Into the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stirs evenly, is placed under 65 degrees celsius and reacts 6 hours,
Product obtains poly hydroxy ethyl acrylate through cooling, dialysis, freeze-drying, by 0.5 gram of polyacrylonitrile, 0.05 gram of Azide
Sodium, 0.05 gram of ammonium chloride will enter into the ampoule bottle equipped with 5.0 milliliters of n,N-Dimethylformamide, stir evenly, are placed in 120
It being reacted 12 hours under degrees celsius, product is acidified through cooling, hydrochloric acid, separates, vacuum drying obtains polyvinyl alcohol tetrazole, and 0.5
Gram polyvinyl alcohol tetrazole, 0.5 gram of poly (glycidyl methacrylate), 0.68 milliliter of triethylamine are added to equipped with 3.0 milliliters of N,
In the ampoule bottle of dinethylformamide, stir evenly, be placed under 65 degrees celsius and react 3 hours, product object through cooling, thoroughly
Analysis, freeze-drying obtain polymer brush.The compound that resulting polymers brush and graphene oxide are constructed is applied to carcinomebryonic antigen
Detection, lowest detection are limited to 2.3 pg/mls.
Embodiment six:
2.0 milliliters of acrylonitrile, 0.042 gram of 4- itrile group valeric acid dithiobenzoic acid, 0.0123 gram of azodiisobutyronitrile are added
Enter into the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stir evenly, it is small to be placed in reaction 4 under 75 degrees celsius
When, product obtains polyacrylonitrile through precipitating, suction filtration, vacuum drying, by 2.0 milliliters of hydroxyethyl methacrylates, 0.0204 milliliter
2- isobutyl ethyl bromide, 0.0310 gram of copper bromide, 0.0294 milliliter of pentamethyl-diethylenetriamine, 0.0243 gram of ascorbic acid are added
Into the ampoule bottle equipped with 2.0 milliliters of n,N-Dimethylformamide, stirs evenly, is placed under 65 degrees celsius and reacts 6 hours,
Product obtains poly hydroxy ethyl acrylate through cooling, dialysis, freeze-drying, by 0.5 gram of polyacrylonitrile, 0.5 gram of sodium azide,
0.5 gram of ammonium chloride will enter into the ampoule bottle equipped with 5.0 milliliters of n,N-Dimethylformamide, stirs evenly, it is Celsius to be placed in 120
It is reacted 12 hours under the conditions of degree, product obtains polyvinyl alcohol tetrazole through cooling, hydrochloric acid acidification, separation, vacuum drying, and 0.5 gram poly-
Vinyl tetrazolium, 1.0 grams of poly (glycidyl methacrylate)s, 1.36 milliliters of triethylamines are added to equipped with 3.0 milliliters of N, N- bis-
In the ampoule bottle of methylformamide, stir evenly, be placed under 65 degrees celsius and react 3 hours, product object through cooling, dialysis,
Freeze-drying obtains polymer brush.The compound that resulting polymers brush and graphene oxide are constructed is applied to the inspection of carcinomebryonic antigen
It surveys, lowest detection is limited to 0.6 pg/ml.
Claims (2)
1. a kind of preparation method for the polymer brush that can be used for chemical-biological sensing, contains carboxyl it is characterized in that: using first
Chain transfer agents obtain the polyacrylonitrile that end group is carboxyl by reversible addion-fragmentation chain transfer free radical polymerization, then with it is folded
Sodium nitride, ammonium chloride are added toN,NIt in dimethylformamide, stirs evenly, it is anti-that click chemistry is carried out under 120 degrees celsius
It answers, reaction carries out at least 12 hours, wherein the mass ratio of polyacrylonitrile and sodium azide is 1:1 ~ 20:1, ammonium chloride and nitrine
The mass ratio for changing sodium is 1:1, and product obtains polyvinyl alcohol tetrazole through cooling, hydrochloric acid acidification, separation, vacuum drying, then will gather
Vinyl tetrazolium is added to the methacrylate quasi polymer and triethylamine prepared by atom transfer radical polymerizationN,NIt in dimethylformamide, stirs evenly, is reacted under 65 degrees celsius, reaction at least carries out 3 hours, wherein described
Methacrylate based polymers are poly (glycidyl methacrylate) and poly hydroxy ethyl acrylate, wherein polyvinyl
Tetrazolium and the mass ratio of methacrylate based polymers are 1:1 ~ 1:5, the matter of triethylamine and methacrylate based polymers
Amount ratio is 1:1, and product obtains polymer brush through cooling, dialysis, freeze-drying.
2. it is described in accordance with the claim 1 it is a kind of can be used for chemical-biological sensing polymer brush preparation method it is characterized in that
The polymer brush of preparation is sensed applied to chemical-biological, can be realized the amplification of carcinomebryonic antigen detection signal, minimum detection limit
For 0.1 pg/ml.
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| CN109908982B (en) * | 2019-03-11 | 2021-04-13 | 黔南民族师范学院 | Preparation method and application of three-dimensional chip for screening traditional Chinese medicine components |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102952236A (en) * | 2011-08-29 | 2013-03-06 | 南开大学 | Molecularly imprinted polymeric microsphere resin applicable to aqueous solution system and preparing method thereof |
| CN103665387A (en) * | 2013-12-09 | 2014-03-26 | 东南大学 | Method for preparing accurate polymer network |
| CN104371131A (en) * | 2014-03-12 | 2015-02-25 | 南开大学 | Preparation method for molecularly imprinted polymer microballoon with hydrophilic high-molecular brush |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102952236A (en) * | 2011-08-29 | 2013-03-06 | 南开大学 | Molecularly imprinted polymeric microsphere resin applicable to aqueous solution system and preparing method thereof |
| CN103665387A (en) * | 2013-12-09 | 2014-03-26 | 东南大学 | Method for preparing accurate polymer network |
| CN104371131A (en) * | 2014-03-12 | 2015-02-25 | 南开大学 | Preparation method for molecularly imprinted polymer microballoon with hydrophilic high-molecular brush |
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