CN104151475A - Preparation method of sugary gel adsorbing material sensitive to pH value - Google Patents
Preparation method of sugary gel adsorbing material sensitive to pH value Download PDFInfo
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Abstract
The invention discloses a preparation method of a sugary gel adsorbing material sensitive to a pH value. The method comprises the following steps: dissolving carbohydrate compounds into an organic solvent, adding a catalytic amount of catalyst and glycidyl methacrylate, and reacting to obtain first reaction liquid; adding acrylic acid, acrylamide and a cross-linking agent to the first reaction liquid after the first reaction liquid is cooled, and adding water to completely dissolve acrylic acid, acrylamide and the cross-linking agent, so as to obtain second reaction liquid; heating the second reaction liquid, adding an initiator, and carrying out reaction under stirring in a thermostat water bath; taking out gel after reaction is ended; firstly cleaning the gel by using deionized water, cutting the gel into small pieces, soaking the gel by using deionized water and then drying the product in a freezer dryer, so as to obtain the sugary gel adsorbing material sensitive to pH. The method disclosed by the invention is low in raw material price, low in cost, simple in synthetic route, short in technological process, mild in reaction condition, low in toxicity, and easy to industrialize.
Description
Technical field
The present invention relates to environment sensitive Polymer materialspreparation method field, be specifically related to a kind of preparation method of the sugary gel sorbing material to pH sensitivity.
Background technology
Macromolecule hydrogel is the cross-linked polymer with tridimensional network that contains hydrophilic radical in a kind of main chain or side chain and can adsorb large quantity of moisture, is studied widely and applies in fields such as biologic medical, food product pack, environment, lives.By changing the high molecular moiety of this three-dimensional network, can prepare the intelligent aqueous gel capable to environment sensitive.This gelatinous material is being subject to after the small physics of external environment, chemical stimulation, and himself character, as considerable change can occur for physical aspect or chemical structure, stimulates to external world and produces response characteristic.Be exactly a kind of typical environmental response hydrogel to the hydrogel of pH sensitivity.
In general, have in the hydrogel network of pH responsiveness and contain acidity, basic group, as carboxyl or amino.Often in tradition adopt acrylic or methacrylic acid to prepare high molecular polymer as functional monomer, but this base polymer is difficult for being degraded by microorganisms, can causes environmental pollution.Meanwhile, along with petrochemical industry resource is day by day deficient, acrylic monomer price will improve, and makes the lifting of the cost value of such macromolecular material.Therefore, natural compounds good biological degradability and vinylformic acid being carried out compound, is the ordinary method of developing at present the responsive gel sorbing material of pH of biodegradation type.
Glucose (chemical formula C
6h
12o
6) claim again corn sugar, be the widest and of paramount importance a kind of monose of distributed in nature.Glucose has the advantages such as source is abundant, cheap, biodegradation type is good; And in its molecule, contain great amount of hydroxy group, strong with water avidity.Therefore, glucose is a kind of potential raw material of preparing gel sorbing material.Sucrose, dextran, Mierocrystalline cellulose etc. meanwhile, there is the saccharide compound of analog structure with glucose, as all can be used as the raw material of gel sorbing material.Zhang Hui etc. are by carrying out the structurally-modified dextran with reactive double bond that purity is higher that obtains to dextran; again under nitrogen protection; prepared the nanogel with acid-sensitive characteristic by initiator and acrylic acid copolymer; this gel can be realized active adsorption and the release (Zhang Hui etc. of different pH values to erythromycin; the preparation of acid sensitivity dextran nanogel and Release Properties are investigated [J]; medicine Leader, 2008,27 (8): 967-970).For obtain there is higher degree need to carry out the purification procedures such as recrystallization or column chromatography containing two key saccharide compounds, in polyreaction, nitrogen protection needs air tight condition simultaneously, the two is and can increases the requirement of plant and instrument and cost drops into.Therefore, directly adopt unpurified polymerization single polymerization monomer, under the condition of nitrogen-less protection, prepare gel sorbing material and seem quite important.
In current Research Literature and patent, the preparation process relative complex of stimuli responsive type hydrogel, experiment condition is too high, and there is certain difficulty in industrialization.
Summary of the invention
the technical problem solving:the invention provides a kind of preparation method of the sugary gel sorbing material to potential of hydrogen sensitivity.The inventive method Raw is cheap, and cost is lower, and synthetic route is succinct, and technical process is short, reaction conditions gentleness, and toxicity is low, is easy to industrialization.
technical scheme: the preparation method of the sugary gel sorbing material to potential of hydrogen sensitivity, formed by following steps: (1) is dissolved in saccharide compound in organic solvent, add catalyzer and the glycidyl methacrylate of catalytic amount, obtain the saccharide compound of methacrylic acidylate in 40 ~ 60 DEG C of reaction 20 ~ 30h, i.e. the first reaction solution; Wherein the molar ratio of saccharide compound and glycidyl methacrylate is 1:0.8 ~ 7; (2) after the first reaction solution is cooling, add wherein vinylformic acid, acrylamide and linking agent, and add water that it is dissolved completely, obtain the second reaction solution; Wherein saccharide compound: vinylformic acid: the mass ratio of acrylamide is 1:(1 ~ 10): (1 ~ 10); It is 0.2% ~ 10% that linking agent accounts for polymerization single polymerization monomer mass percent; (3) by the second reaction solution heating 5min, add initiator, stirring reaction in 60 ~ 80 DEG C of thermostat water baths, the reaction times is at 0.5 ~ 3h; Wherein to account for polymerization single polymerization monomer mass percent be 0.2% ~ 10% to initiator; (4) after reaction finishes, gel is taken out, first by washed with de-ionized water and be cut into small pieces, then after soaking with deionized water, product is dry in freeze drier, obtain the sugar-containing hydrogel sorbing material to pH sensitivity.
In above-mentioned steps (1), saccharide compound is the one in glucose, sucrose, cellobiose, dextran, Mierocrystalline cellulose.
In above-mentioned steps (1), organic solvent is the one in dimethyl sulfoxide (DMSO), DMF, DMF, acetone, dioxane.
In above-mentioned steps (1), catalyzer is the one in pyridine, DMAP, Tetramethyl Ethylene Diamine, triethylamine, dimethylcyclohexylamine.
In above-mentioned steps (2), linking agent is N,N methylene bis acrylamide, N, the one in two (methylol) urea of N-, polyoxyethylene glycol, polyvinyl alcohol.
In above-mentioned steps (3), initiator is the one in ammonium persulphate, Potassium Persulphate, Diisopropyl azodicarboxylate, benzoyl peroxide.
beneficial effect:it is raw material that the present invention adopts saccharide compound; with glycidyl methacrylate, its modification is obtained having the saccharide compound solution of reactive double bond; under the condition of nitrogen-less protection, prepare the sugary gel sorbing material to pH sensitivity with vinylformic acid, acrylamide copolymerization; there is the features such as raw material cheapness, reaction conditions gentleness, conversion unit be simple, and the gel obtaining has good water absorbing properties.
Brief description of the drawings
Fig. 1 be in embodiment 3 to the sugary gel sorbing material of pH sensitivity the swelling figure in each pH medium solution; By finding out in figure that, in different pH medium solution, the swelling ratio of gelatinous material all increases along with the prolongation of time, tends towards stability afterwards to a certain extent; And gel swelling ratio in alkaline medium increases faster.Find, along with the increase of pH, the swelling ratio of gel increases simultaneously.This is because vinylformic acid is weak acid, is difficult to ionization under acidic conditions, and macromolecular chain is crimped onto together, and the swelling ratio of gel is less; And under higher pH value solution, vinylformic acid salify and produce electrostatic repulsion, thereby the swelling ratio of gel increases.
Fig. 2 be in embodiment 4 to the sugary gel sorbing material of pH sensitivity the swelling figure in each pH medium solution.By finding out in figure that, in different pH medium solution, the swelling ratio of gelatinous material all increases along with the prolongation of time, tends towards stability afterwards to a certain extent; And gel swelling ratio in alkaline medium increases faster.Find, along with the increase of pH, the swelling ratio of gel increases simultaneously.This is because vinylformic acid is weak acid, is difficult to ionization under acidic conditions, and macromolecular chain is crimped onto together, and the swelling ratio of gel is less; And under higher pH value solution, vinylformic acid salify and produce electrostatic repulsion, thereby the swelling ratio of gel increases.
Embodiment
Further set forth the present invention below in conjunction with specific embodiment.It should be noted, each embodiment is below exemplary, and does not expect to limit the scope of the invention.Reading after content of the present invention, those skilled in the art can make various changes or modifications the present invention, and these equivalent form of values fall within equally the application and pay claims limited range.
embodiment 1
0.2g glucose is dissolved in 1mL DMSO, adds successively 0.04g pyridine and 0.13g glycidyl methacrylate, after dissolving completely, in 50 DEG C of oil baths, stirring reaction 20h obtains the glucose solution of methacrylic acidylate, i.e. the first reaction solution.After the first reaction solution is cooling, add wherein 0.2g vinylformic acid, 0.2g acrylamide, 0.01gN, N-methylene-bisacrylamide, and add 5mL deionized water, in 70 DEG C of water-baths, heating is dissolved each component completely.Add 0.01g ammonium persulphate, stop at need stirring to stirring when reactant becomes thickness, make the reaction times at 3h thereafter.After reaction finishes, gel is taken out, first by washed with de-ionized water and be cut into small pieces, then soak 7 days with deionized water, every 6h changes once, finally product is dried in freeze drier, obtains the sugary gel sorbing material to pH sensitivity.
Get 0.067g xerogel and put into 400mL deionized water, leave standstill water suction, reach after swelling equilibrium until complete gel, take out hydrogel material, wipe after surface-moisture with moistening test paper, claim that its weight is 2.783g.Calculated equilibrium swelling capacity as follows:
Dry weight before equilibrium swelling degree=(the front dry weight of weight-water suction after water suction)/water suction;
Equilibrium swelling degree=(the 2.783-0.067)/0.067=40.54 g/g of gel;
In this embodiment, the equilibrium swelling degree of the prepared sugary gel sorbing material to pH sensitivity is 40.54 g/g.
embodiment 2
0.2g glucose is dissolved in 1mL DMSO, adds successively 0.04g pyridine and 0.26g glycidyl methacrylate, after dissolving completely, in 50 DEG C of oil baths, stirring reaction 20h obtains the glucose solution of methacrylic acidylate, i.e. the first reaction solution.After the first reaction solution is cooling, add wherein 0.4g vinylformic acid, 0.4g acrylamide, 0.01gN, N-methylene-bisacrylamide, and add 5mL deionized water, in 70 DEG C of water-baths, heating is dissolved each component completely.Add 0.01g ammonium persulphate, stop at need stirring to stirring when reactant becomes thickness, make the reaction times at 3h thereafter.After reaction finishes, gel is taken out, first by washed with de-ionized water and be cut into small pieces, then soak 7 days with deionized water, every 6h changes once, finally product is dried in freeze drier, obtains the sugary gel sorbing material to pH sensitivity.
Get 0.050g xerogel and put into 400mL deionized water, leave standstill water suction, reach after swelling equilibrium until complete gel, take out hydrogel material, wipe after surface-moisture with moistening test paper, claim that its weight is 2.86g.Calculated equilibrium swelling capacity as follows:
Dry weight before equilibrium swelling degree=(the front dry weight of weight-water suction after water suction)/water suction;
Equilibrium swelling degree=(the 2.86-0.050)/0.050=56.20 g/g of gel;
In this embodiment, the equilibrium swelling degree of the prepared sugary gel sorbing material to pH sensitivity is 56.20 g/g.
embodiment 3
0.2g glucose is dissolved in 1mL DMSO, adds successively 0.04g pyridine and 0.19g glycidyl methacrylate, after dissolving completely, in 50 DEG C of oil baths, stirring reaction 20h obtains the glucose solution of methacrylic acidylate, i.e. the first reaction solution.After the first reaction solution is cooling, add wherein 0.6g vinylformic acid, 0.6g acrylamide, 0.02gN, N-methylene-bisacrylamide, and add 10mL deionized water, in 70 DEG C of water-baths, heating is dissolved each component completely.Add 0.02g ammonium persulphate, stop at need stirring to stirring when reactant becomes thickness, make the reaction times at 3h thereafter.After reaction finishes, gel is taken out, first by washed with de-ionized water and be cut into small pieces, then soak 7 days with deionized water, every 6h changes once, finally product is dried in freeze drier, obtains the sugary gel sorbing material to pH sensitivity.
Get 0.069g xerogel and put into 400mL deionized water, leave standstill water suction, reach after swelling equilibrium until complete gel, take out hydrogel material, wipe after surface-moisture with moistening test paper, claim that its weight is 5.165g.Calculated equilibrium swelling capacity as follows:
Dry weight before equilibrium swelling degree=(the front dry weight of weight-water suction after water suction)/water suction;
Equilibrium swelling degree=(the 5.165-0.069)/0.069=73.86 g/g of gel;
In this embodiment, the equilibrium swelling degree of the prepared sugary gel sorbing material to pH sensitivity is 73.86 g/g.
embodiment 4
0.2g glucose is dissolved in 1mL DMSO, adds successively 0.04g pyridine and 0.19g glycidyl methacrylate, after dissolving completely, in 50 DEG C of oil baths, stirring reaction 20h obtains the glucose solution of methacrylic acidylate, i.e. the first reaction solution.After the first reaction solution is cooling, add wherein 0.8g vinylformic acid, 0.8g acrylamide, 0.02gN, N-methylene-bisacrylamide, and add 10mL deionized water, in 70 DEG C of water-baths, heating is dissolved each component completely.Add 0.02g ammonium persulphate, stop at need stirring to stirring when reactant becomes thickness, make the reaction times at 3h thereafter.After reaction finishes, gel is taken out, first by washed with de-ionized water and be cut into small pieces, then soak 7 days with deionized water, every 6h changes once, finally product is dried in freeze drier, obtains the sugary gel sorbing material to pH sensitivity.
Get 0.087g xerogel and put into 400mL deionized water, leave standstill water suction, reach after swelling equilibrium until complete gel, take out hydrogel material, wipe after surface-moisture with moistening test paper, claim that its weight is 4.984g.Calculated equilibrium swelling capacity as follows:
Dry weight before equilibrium swelling degree=(the front dry weight of weight-water suction after water suction)/water suction;
Equilibrium swelling degree=(the 4.984-0.087)/0.087=56.29 g/g of gel;
In this embodiment, the equilibrium swelling degree of the prepared sugary gel sorbing material to pH sensitivity is 56.29 g/g.
embodiment 5
0.2g glucose is dissolved in 1mL DMSO, adds successively 0.04g pyridine and 0.65g glycidyl methacrylate, after dissolving completely, in 50 DEG C of oil baths, stirring reaction 20h obtains the glucose solution of methacrylic acidylate, i.e. the first reaction solution.After the first reaction solution is cooling, add wherein 1.0g vinylformic acid, 1.0g acrylamide, 0.02gN, N-methylene-bisacrylamide, and add 10mL deionized water, in 70 DEG C of water-baths, heating is dissolved each component completely.Add 0.02g ammonium persulphate, stop at need stirring to stirring when reactant becomes thickness, make the reaction times at 3h thereafter.After reaction finishes, gel is taken out, first by washed with de-ionized water and be cut into small pieces, then soak 7 days with deionized water, every 6h changes once, finally product is dried in freeze drier, obtains the sugary gel sorbing material to pH sensitivity.
Get 0.060g xerogel and put into 400mL deionized water, leave standstill water suction, reach after swelling equilibrium until complete gel, take out hydrogel material, wipe after surface-moisture with moistening test paper, claim that its weight is 2.853g.Calculated equilibrium swelling capacity as follows:
Dry weight before equilibrium swelling degree=(the front dry weight of weight-water suction after water suction)/water suction;
Equilibrium swelling degree=(the 2.853-0.060)/0.060=46.55 g/g of gel;
In this embodiment, the equilibrium swelling degree of the prepared sugary gel sorbing material to pH sensitivity is 46.55 g/g.
Claims (6)
1. the preparation method of the sugary gel sorbing material of pair potential of hydrogen sensitivity, is characterized in that being made up of following steps:
(1) saccharide compound is dissolved in organic solvent, adds catalyzer and the glycidyl methacrylate of catalytic amount, obtain the saccharide compound of methacrylic acidylate in 40 ~ 60 DEG C of reaction 20 ~ 30h, i.e. the first reaction solution; Wherein the molar ratio of saccharide compound and glycidyl methacrylate is 1:0.8 ~ 7;
(2) after the first reaction solution is cooling, add wherein vinylformic acid, acrylamide and linking agent, and add water that it is dissolved completely, obtain the second reaction solution; Wherein saccharide compound: vinylformic acid: the mass ratio of acrylamide is 1:(1 ~ 10): (1 ~ 10); It is 0.2% ~ 10% that linking agent accounts for polymerization single polymerization monomer mass percent;
(3) by the second reaction solution heating 5min, add initiator, stirring reaction in 60 ~ 80 DEG C of thermostat water baths, the reaction times is at 0.5 ~ 3h; Wherein to account for polymerization single polymerization monomer mass percent be 0.2% ~ 10% to initiator;
(4) after reaction finishes, gel is taken out, first by washed with de-ionized water and be cut into small pieces, then after soaking with deionized water, product is dry in freeze drier, obtain the sugar-containing hydrogel sorbing material to pH sensitivity.
2. the preparation method of the sugary gel sorbing material to potential of hydrogen sensitivity according to claim 1, is characterized in that: in described step (1), saccharide compound is the one in glucose, sucrose, cellobiose, dextran, Mierocrystalline cellulose.
3. the preparation method of the sugary gel sorbing material to potential of hydrogen sensitivity according to claim 1, it is characterized in that: in described step (1), organic solvent is dimethyl sulfoxide (DMSO), N, one in dinethylformamide, DMF, acetone, dioxane.
4. the preparation method of the sugary gel sorbing material to potential of hydrogen sensitivity according to claim 1, is characterized in that: in described step (1), catalyzer is the one in pyridine, DMAP, Tetramethyl Ethylene Diamine, triethylamine, dimethylcyclohexylamine.
5. the preparation method of the sugary gel sorbing material to potential of hydrogen sensitivity according to claim 1, it is characterized in that: in described step (2), linking agent is N, N-methylene-bisacrylamide, N, the one in two (methylol) urea of N-, polyoxyethylene glycol, polyvinyl alcohol.
6. the preparation method of the sugary gel sorbing material to potential of hydrogen sensitivity according to claim 1, is characterized in that: in described step (3), initiator is the one in ammonium persulphate, Potassium Persulphate, Diisopropyl azodicarboxylate, benzoyl peroxide.
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| CN106821963A (en) * | 2016-12-28 | 2017-06-13 | 浙江理工大学 | A kind of method of utilization cellulose base temperature and the load of pH sensitive hydrogels and slow releasing pharmaceutical |
| CN107602766A (en) * | 2017-09-06 | 2018-01-19 | 中国林业科学研究院林产化学工业研究所 | Cellulose base water imbibition gel and preparation method thereof |
| CN113209913A (en) * | 2021-04-26 | 2021-08-06 | 上海爱普食品工业有限公司 | Preparation method of caramel-colored hydrogel |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104961855A (en) * | 2015-06-15 | 2015-10-07 | 中国林业科学研究院林产化学工业研究所 | Preparation method of compound water gel material |
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| CN113209913A (en) * | 2021-04-26 | 2021-08-06 | 上海爱普食品工业有限公司 | Preparation method of caramel-colored hydrogel |
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