CN109575153B - Polysaccharide derivative polymer and preparation method thereof - Google Patents
Polysaccharide derivative polymer and preparation method thereof Download PDFInfo
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- CN109575153B CN109575153B CN201811398306.1A CN201811398306A CN109575153B CN 109575153 B CN109575153 B CN 109575153B CN 201811398306 A CN201811398306 A CN 201811398306A CN 109575153 B CN109575153 B CN 109575153B
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- dimethylacetamide
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
Abstract
The invention discloses a polysaccharide derivative polymer, which is characterized in that: the material is prepared by performing polycondensation reaction on 1 mol part of polysaccharide, 3-7 mol parts of pyromellitic anhydride, 0-0.4 mol part of octahydroxyl polyhedral oligomeric silsesquioxane, 0.02-0.4 mol part of octaamino polyhedral oligomeric silsesquioxane, 0.2-1.0 mol part of diamine, 0.5 mol part of triethylamine, 0-0.003 mol part of tween and 0.001-0.003 mol part of span; the polysaccharide derivative polymer is an organic-inorganic complex, has good thermal stability and medium swelling resistance, can reversibly adsorb and desorb formaldehyde, and has bright application prospect in the field of environmental pollution control engineering materials.
Description
Technical Field
The invention relates to the field of engineering materials for controlling environmental pollution, in particular to a polysaccharide derivative polymer and a preparation method thereof.
Background art:
the polysaccharide comprises cyclodextrin, xylan, chitosan, glucan, mannan, starch, cellulose and the like, has the advantages of wide natural source, low price, good biocompatibility, biodegradability and the like, and is an ideal environment-friendly biomass raw material. In recent years, polysaccharide-derived polymers have shown important and bright application prospects in the fields of environmental science, chemical analysis, biomedicine, organic synthesis, industrial catalysis and the like.
Polysaccharide molecules contain a large number of free hydroxyl groups, amino groups and/or aldehyde groups, have strong chemical reaction activity, and are easy to solidify by a polycondensation method to become polymer derivative materials with different properties. The chain structure of the materials contains oxygen and nitrogen heteroatoms, and has residual hydroxyl and/or amino, and under different chemical environments such as pH and the like, the materials can be complexed with various molecules through coordination; and the original special structure of polysaccharide molecules can be retained to a certain extent after polycondensation, so that the final derivative is endowed with a special three-dimensional structure, and excellent performances are obtained for molecular adsorption and desorption, molecular recognition and screening.
The existing polysaccharide derivative polymer mainly relates to several cross-linked polymers such as cyclodextrin, chitosan, starch, cellulose and the like. The processes for their preparation are almost exclusively based on condensation reactions of amino and/or hydroxyl groups, including aldehyde condensation, epoxy etherification, acyl halide crosslinking, anhydride derivatization, isocyanate bridging and the like. Although the development of polysaccharide-derived polymers has been remarkably achieved by human beings, the engineering application of the polysaccharide-derived polymers is still insufficient, which is mainly caused by the defects of poor thermal stability, poor medium swelling resistance, short recycling life and the like of the existing polysaccharide-derived polymers which are mostly purely organic cured polymers.
Disclosure of Invention
The invention aims to provide a polysaccharide derivative polymer and a preparation method thereof, wherein the polysaccharide derivative polymer is an organic-inorganic complex and can effectively avoid the defects of a pure organic polysaccharide derivative polymer.
The technical scheme adopted for realizing the purpose of the invention is as follows:
the polysaccharide derivative polymer is characterized by being obtained by performing polycondensation on the following components in parts by mole:
polysaccharide 1
3-7 parts of pyromellitic anhydride
0-0.4 octahydroxy polyhedral oligomeric silsesquioxane
0.02-0.4% of octamino polyhedral oligomeric silsesquioxane
Diamine 0.2-1.0
Triethylamine 0.5
Tween 0-0.003
Span is 0.001-0.003.
A process for preparing such polysaccharide derived polymers comprising the steps of:
(1) respectively preparing saturated solutions of 3-7 parts by mole of pyromellitic anhydride, 0-0.4 part by mole of octahydroxyl polyhedral oligomeric silsesquioxane, 0.02-0.4 part by mole of octaamino polyhedral oligomeric silsesquioxane and 0.2-1.0 part by mole of diamine by using N, N-dimethylacetamide at room temperature;
(2) preparing 1 mole part of N, N-dimethylacetamide saturated solution of polysaccharide at 120-130 ℃, mechanically stirring, adding 0-0.003 mole part of tween, 0.001-0.003 mole part of span and 0.5 mole part of triethylamine, supplementing N, N-dimethylacetamide with the mass of 30-60% of the mass of the polysaccharide N, N-dimethylacetamide, continuously stirring until no visible solid particles exist in the mixing system, and sequentially and rapidly adding the three N, N-dimethylacetamide saturated solutions of the octahydroxy polyhedral oligomeric silsesquioxane, the octaamino polyhedral oligomeric silsesquioxane and pyromellitic dianhydride obtained in the step (1); continuously mechanically stirring to ensure uniform mixing and stable reaction, and cooling the mixed reaction system to room temperature after 1-2 hours to obtain a prepolymerization solution;
(3) mechanically stirring and quickly injecting the diamine N, N-dimethylacetamide saturated solution obtained in the step (1) into the prepolymerization solution obtained in the step (2), continuously stirring until no obvious precipitate is generated in a mixing system, cooling the system to room temperature, filtering, cleaning and drying to obtain a crude polysaccharide derivative polymer;
(4) and (4) aging the crude polysaccharide derivative polymer obtained in the step (3) for 3 hours in a vacuum environment at 250 ℃, discharging, and cooling to room temperature to obtain the polysaccharide derivative polymer.
The polysaccharide of the invention refers to cyclodextrin, xylan, chitosan, glucan, mannan, starch or fiberA vitamin; the weight average molecular weight (M) is preferablyw) Less than 10000 polysaccharide.
The diamine refers to p-phenylenediamine, o-phenylenediamine, m-phenylenediamine, 2-chloro-p-phenylenediamine, 2, 4-toluenediamine, 2, 5-toluenediamine, ethylenediamine, hexamethylenediamine or decamethylenediamine.
The Tween in the invention is preferably Tween 20, Tween 40, Tween 60, Tween 80 or Tween 85.
The span of the invention is preferably span 20, span 40, span 60, span 80 or span 85.
The polysaccharide derivative polymer has the following advantages: (1) the polymer is a poly-condensation cross-linked body of polysaccharide, octahydroxy and/or amino polyhedral oligomeric silsesquioxane and pyromellitic dianhydride, so that the polymer has inorganic structural units similar to silicon dioxide and organic structural units similar to polyamide, and belongs to an inorganic-organic complex; (2) a large number of carboxyl groups are arranged on the structure, so that the hydrophilic property is good; (3) the non-aqueous medium has good anti-medium swelling performance, and the swelling rate of the non-aqueous medium at normal temperature is not more than 5.5%; (4) the thermal stability is good, and the initial decomposition temperature is higher than 350 ℃; (5) has reversible adsorption-desorption function, can circularly adsorb and desorb formaldehyde at room temperature, and the three-time circulating desorption rate can reach more than 91 percent. These characteristics cannot be found simultaneously in the existing similar polymer products.
Detailed Description
The invention is illustrated or described in more detail by the following specific examples, which are not intended to be limiting of the invention.
Example 1
(1) Respectively preparing 0.3 mol of pyromellitic dianhydride, 0.04 mol of octamino polyhedral oligomeric silsesquioxane and 0.1 mol of N, N-dimethylacetamide saturated solution of hexamethylene diamine at the room temperature of 20 ℃;
(2) 0.1 mol of dextran (M) was prepared at 130 ℃w5000) of N, N-dimethylacetamide saturated solution, and 0.0003 mol of Tween 40, 0.0001 mol of span 85 and 0.05 mol of triethylamine are added thereto with mechanical stirring, and then dextran N, N-dimethylacetamide saturated solution is addedAnd N, N-dimethylacetamide with the solution mass of 60%, continuously stirring until no visible solid particles exist in the mixing system, and then sequentially and rapidly adding the N, N-dimethylacetamide saturated solution of the octamino polyhedral oligomeric silsesquioxane and the pyromellitic dianhydride obtained in the step (1); continuously mechanically stirring to ensure uniform mixing and stable reaction, and cooling the mixed reaction system to room temperature after 1 hour to obtain a prepolymerization solution 1;
(3) mechanically stirring, quickly injecting the hexamethylenediamine N, N-dimethylacetamide saturated solution obtained in the step (1) into the prepolymerization solution 1, continuously stirring until no obvious precipitate is generated in a mixing system, cooling the system to room temperature, filtering, cleaning and drying to obtain a crude glucan derivative polymer 1;
(4) and aging the crude glucan derivative polymer 1 for 3 hours at 250 ℃ in a vacuum environment, discharging, and cooling to room temperature to obtain the glucan derivative polymer 1. A small amount was taken for thermogravimetric analysis and the initial decomposition temperature was found to be 356 ℃.
Example 2
(1) Respectively preparing 0.5 mole of pyromellitic dianhydride, 0.02 mole of octahydroxyl polyhedral oligomeric silsesquioxane, 0.018 mole of octaamino polyhedral oligomeric silsesquioxane and 0.05 mole of N, N-dimethylacetamide saturated solution of p-phenylenediamine at the room temperature of 20 ℃;
(2) preparing N, N-dimethylacetamide saturated solution of 0.1 mole of chitosan (the deacetylation degree is more than or equal to 95 percent, and the viscosity is 100-200 mpa.s), mechanically stirring, adding 0.0002 mole of Tween 60, 0.0002 mole of span 40 and 0.05 mole of triethylamine into the N, N-dimethylacetamide solution, supplementing N, N-dimethylacetamide solution with the mass of 45 percent of the mass of the chitosan N, N-dimethylacetamide saturated solution, continuously stirring until no visible solid particles exist in the mixing system, and sequentially and rapidly adding the three N, N-dimethylacetamide saturated solutions of the octahydroxy polyhedral oligomeric silsesquioxane, the octaamino polyhedral oligomeric silsesquioxane and the pyromellitic dianhydride obtained in the step (1) in sequence; continuously mechanically stirring to ensure uniform mixing and stable reaction, and cooling the mixed reaction system to room temperature after 1.5 hours to obtain a prepolymerization solution 2;
(3) mechanically stirring, quickly injecting the p-phenylenediamine N, N-dimethylacetamide saturated solution obtained in the step (1) into the prepolymerization solution 2, continuously stirring until no obvious precipitate is generated in a mixing system, cooling the system to room temperature, filtering, cleaning and drying to obtain a crude chitosan derivative polymer;
(4) aging the coarse chitosan derivative polymer for 3 hours in a vacuum environment at 250 ℃, discharging, and cooling to room temperature to obtain a chitosan derivative polymer; a small amount was taken for thermogravimetric analysis and the initial decomposition temperature was found to be 384 ℃.
Example 3
(1) Respectively preparing 0.7 mole of pyromellitic dianhydride, 0.04 mole of octahydroxyl polyhedral oligomeric silsesquioxane, 0.002 mole of octaamino polyhedral oligomeric silsesquioxane and 0.02 mole of N, N-dimethylacetamide saturated solution of 2, 4-toluenediamine at the room temperature of 20 ℃;
(2) at 120 ℃, 0.1 mol of the compound is preparedαMechanically stirring an N, N-dimethylacetamide saturated solution of cyclodextrin, adding 0.0003 mol of span 40 and 0.05 mol of triethylamine, supplementing 30% by mass of N, N-dimethylacetamide of the alpha-cyclodextrin N, N-dimethylacetamide saturated solution, continuously stirring until no visible solid particles exist in a mixing system, and sequentially and rapidly adding three N, N-dimethylacetamide saturated solutions of the octahydroxy polyhedral oligomeric silsesquioxane, the octaamino polyhedral oligomeric silsesquioxane and the pyromellitic dianhydride obtained in the step (1); continuously mechanically stirring to ensure uniform mixing and stable reaction, and cooling the mixed reaction system to room temperature after 2 hours to obtain a prepolymerization solution 3;
(3) mechanically stirring and quickly injecting the 2, 4-toluenediamine N, N-dimethylacetamide saturated solution obtained in the step (1) into the prepolymerization solution 3, continuously stirring until no obvious precipitate is generated in the mixing system, cooling the system to room temperature, filtering, cleaning and drying to obtain a coarse-grade productα-a cyclodextrin derivatised polymer;
(4) will be coarsely gradedαAging cyclodextrin derivative polymer at 250 deg.C for 3 hr, discharging, and cooling to room temperature to obtain final productα-a cyclodextrin derivatised polymer; a small amount of the extract was subjected to thermogravimetric analysis, and found to beThe initial decomposition temperature was 371 ℃.
Example 4
(1) Respectively preparing 0.5 mole of pyromellitic dianhydride, 0.02 mole of octahydroxyl polyhedral oligomeric silsesquioxane, 0.018 mole of octaamino polyhedral oligomeric silsesquioxane and 0.05 mole of N, N-dimethylacetamide saturated solution of p-phenylenediamine at the room temperature of 20 ℃;
(2) at 125 ℃, 0.1 mol of the compound is preparedβA saturated solution of cyclodextrin in N, N-dimethylacetamide, to which 0.0002 mol of Tween 60, 0.0002 mol of span 40 and 0.05 mol of triethylamine are added with mechanical stirring, and the added amount isβN, N-dimethylacetamide with the mass of 45% of cyclodextrin N, N-dimethylacetamide saturated solution is continuously stirred until no visible solid particles exist in the mixing system, and then three N, N-dimethylacetamide saturated solutions of the octahydroxyl polyhedral oligomeric silsesquioxane, the octaamino polyhedral oligomeric silsesquioxane and the pyromellitic dianhydride obtained in the step (1) are sequentially and rapidly added; continuously mechanically stirring to ensure uniform mixing and stable reaction, and cooling the mixed reaction system to room temperature after 1.5 hours to obtain a prepolymerization solution 4;
(3) mechanically stirring and quickly injecting the p-phenylenediamine N, N-dimethylacetamide saturated solution obtained in the step (1) into the prepolymerization solution 4, continuously stirring until no obvious precipitate is generated in a mixing system, cooling the system to room temperature, filtering, cleaning and drying to obtain a coarse-grade productβ-a cyclodextrin derivatised polymer;
(4) will be coarsely gradedβAging cyclodextrin derivative polymer at 250 deg.C for 3 hr, discharging, and cooling to room temperature to obtain final productβ-a cyclodextrin derivatised polymer; a small amount was taken for thermogravimetric analysis and the initial decomposition temperature was found to be 389 ℃.
The samples obtained in the above examples are subjected to a swelling experiment at the normal temperature of 28 ℃, namely Mg (0.5 g) is respectively taken and immersed in different solvents, and after 7 days, the samples are taken out, the solvents on the surfaces of the samples are quickly wiped off by using filter paper, and the samples are weighed to obtain Mg; is composed ofηThe swelling ratio η of the sample was calculated as =100% × Δ M/M =100% × (M-M)/M, and the results are shown in the following table:
as can be seen from the above table, the swelling rates of the polysaccharide-derived polymer obtained by implementing the method of the invention in water and non-aqueous media at the normal temperature of 28 ℃ are respectively not more than 25.5% and not more than 5.5%, which shows that the polymer has good anti-media swelling performance.
The samples obtained in the above examples were subjected to a formaldehyde dynamic adsorption-desorption test at 25 ℃ at room temperature: grinding polysaccharide derivative polymer sample uniformly, taking 0.3g as adsorbent, filling into a quartz tube with inner diameter of 10mm, and using as adsorption column; taking nitrogen as carrier gas, and keeping the space velocity at 500 h-1Introducing formaldehyde into the adsorption column bed by a bubbling method; the concentration of the formaldehyde in the inlet air is 45mg/m3Performing 24-hour dynamic equilibrium adsorption, quantitatively analyzing and calculating the reduction amount of formaldehyde before and after dynamic adsorptionQ e(mg formaldehyde/adsorbent g). After adsorption saturation, the carrier gas is heated to 80 ℃, the carrier gas is blown and desorbed at the speed of 100mL/min, all desorbed formaldehyde is collected, quantitative analysis is carried out, and the formaldehyde desorption amount is calculatedQ d(mg formaldehyde/adsorbent g), and desorption rate N (%). The same procedure was followed for two more adsorption and desorption experiments, with the results shown in the following table:
according to a formaldehyde dynamic adsorption-desorption test, the polysaccharide derivative polymer has the function of reversibly adsorbing and desorbing formaldehyde, can be recycled, and has desorption rates of more than 91% in three cycles.
Claims (6)
1. The polysaccharide derivative polymer is characterized by being obtained by performing polycondensation on the following components in parts by mole:
polysaccharide 1
3-7 parts of pyromellitic anhydride
0-0.4 octahydroxy polyhedral oligomeric silsesquioxane
0.02-0.4% of octamino polyhedral oligomeric silsesquioxane
Diamine 0.2-1.0
Triethylamine 0.5
Tween 0-0.003
Span 0.001-0.003;
the polysaccharide is one or more of cyclodextrin, xylan, chitosan, glucan, mannan, starch or cellulose.
2. The polysaccharide derivative polymer of claim 1, wherein the diamine is one or more selected from the group consisting of p-phenylenediamine, o-phenylenediamine, m-phenylenediamine, 2-chloro-p-phenylenediamine, 2, 4-toluenediamine, 2, 5-toluenediamine, ethylenediamine, hexamethylenediamine, and decamethylenediamine.
3. The polysaccharide derived polymer of claim 1, wherein the polysaccharide has a weight average molecular weight of less than 10000.
4. A method of preparing a polysaccharide derived polymer comprising the steps of:
(1) preparing saturated solution by using 3-7 molar parts of pyromellitic dianhydride, 0-0.4 molar part of octahydroxy polyhedral oligomeric silsesquioxane, 0.02-0.4 molar part of octaamino polyhedral oligomeric silsesquioxane and 0.2-1.0 molar part of diamine at room temperature by using N, N-dimethylacetamide as a solvent;
(2) preparing N, N-dimethylacetamide saturated solution by using 1 mole part of polysaccharide at 120-130 ℃, mechanically stirring, adding 0-0.003 mole part of tween, 0.001-0.003 mole part of span and 0.5 mole part of triethylamine, supplementing N, N-dimethylacetamide with the mass of 30-60% of polysaccharide N, N-dimethylacetamide, continuously stirring until solid particles are not visible in a mixing system, and rapidly adding the three N, N-dimethylacetamide saturated solutions of the octahydroxyl polyhedral oligomeric silsesquioxane, the octaamino polyhedral oligomeric silsesquioxane and the pyromellitic dianhydride obtained in the step (1); continuously mechanically stirring to ensure uniform mixing and stable reaction, and cooling the mixed reaction system to room temperature after 1-2 hours to obtain a prepolymerization solution; the polysaccharide is one or a mixture of more of cyclodextrin, xylan, chitosan, glucan, mannan, starch or cellulose;
(3) quickly injecting the saturated solution of the diamine obtained in the step (1) into the prepolymerization solution, continuously stirring until no obvious precipitate is generated in a mixing system, cooling the mixing system to room temperature, filtering, cleaning and drying to obtain a crude polysaccharide derivative polymer;
(4) and aging the crude polysaccharide derivative polymer for 3 hours at 250 ℃ in a vacuum environment, discharging, and cooling to room temperature to obtain the polysaccharide derivative polymer.
5. The method of claim 4, wherein the diamine is one or more selected from the group consisting of p-phenylenediamine, o-phenylenediamine, m-phenylenediamine, 2-chloro-p-phenylenediamine, 2, 4-toluenediamine, 2, 5-toluenediamine, ethylenediamine, hexamethylenediamine, and decamethylenediamine.
6. The method of claim 4, wherein the polysaccharide has a weight average molecular weight of less than 10000.
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| US7790803B2 (en) * | 2008-06-02 | 2010-09-07 | Uop Llc | Crosslinked organic-inorganic hybrid membranes and their use in gas separation |
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