CN106905450A - A kind of preparation method of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon adsorbent for heavy metal - Google Patents
A kind of preparation method of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon adsorbent for heavy metal Download PDFInfo
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- CN106905450A CN106905450A CN201710169853.1A CN201710169853A CN106905450A CN 106905450 A CN106905450 A CN 106905450A CN 201710169853 A CN201710169853 A CN 201710169853A CN 106905450 A CN106905450 A CN 106905450A
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- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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Abstract
The invention discloses a kind of preparation method of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon adsorbent for heavy metal, belong to water environment protection field.The present invention prepares chitosan microball by spray drying process first, then the surface that methyl acrylate is grafted to chitosan microball is prepared by methyl acrylate grafted chitosan microballoon by Michael's addition, diethylenetriamine is finally grafted to the surface of methyl acrylate grafted chitosan microballoon by substitution reaction, separation, washing, drying both obtain adsorbent for heavy metal.The present invention a large amount of acid amides and amino-functional group on adsorbent surface is grafted by the method for Hyperbranched Polymer with Terminal Amido grafting, the tactful of grafting functional group also causes that functional group, farthest exposed to adsorbent surface, enhances the adsorption effect of adsorbent for heavy metal again first to prepare microballoon simultaneously.
Description
Technical field
The invention belongs to a kind of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon heavy metal in water environment protection field
The preparation method of ion adsorbent.
Background technology
Because heavy metal ion has high toxicity, non-biodegradable and enriching in vivo, into natural environment
Constantly accumulation afterwards, and human body is further diverted into by food chain, serious harm is brought to natural environment and human health.
Therefore, it is a urgent task to research and develop environmentally safe and efficient heavy metal ion administering method.
Shitosan is the second largest natural polysaccharide that content is only second to cellulose in nature, is obtained by chitin deacetylase,
It is widely distributed, it is cheap.Shitosan has the advantages that good biocompatibility, biodegradability, nontoxicity.In addition,
Contain substantial amounts of-OH and-NH in chitosan molecule2Active group, can chelate contents of many kinds of heavy metal ion, therefore be widely studied
For heavy metal ion adsorbed field.Powder type or nano level shitosan are not easy to separate and recycle, therefore typically
Shitosan is prepared into after micron-sized particle is used for the absorption of heavy metal ion.Research finds that either Chitosan powder is also
It is chitosan particle, in acid medium during Adsorption of Heavy Metals ion, all can be because of-NH in molecule2It is protonated to form-NH3 +
And the loss that water causes adsorbent is dissolved in, so as to limit its range of application.Addition crosslinking agent can strengthen the machinery of shitosan
Intensity and its stability in acid medium, but crosslinking agent can influence it to a huge sum of money by occupying the functional group of shitosan
The adsorption capacity of category.For the purpose of overcoming drawbacks described above, many researchs are concentrated on and shitosan carried out after functional group grafting again
It is crosslinked, adds somewhat to the stability and absorption property of product, but still there is certain defect：（1）Grafting
Functional group still some take part in crosslinking；（2）Only partial function group is exposed plays absorption work in microsphere surface
With most of functional groups are embedded in the inside of microballoon；（3）Reason is not reaching to while increased adsorbent preparation cost
The adsorption effect thought.Therefore, the adsorbent for heavy metal that research and development have stability, low cost and high efficiency of additive capability concurrently is that pendulum exists
An important issue in face of numerous scientific workers.
The content of the invention
Inhaled it is an object of the invention to provide a kind of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon heavy metal ion
Attached dose of preparation method, makes up the deficiency of original technology.
Main raw material of chitosan used by the present invention is the natural polysaccharide that content is only second to cellulose in nature, and source is wide
It is general, it is cheap, effectively reduce production cost；Shitosan has good biocompatibility and nontoxicity, will not be to environment
Cause secondary pollution；Contain a large amount of-OH and-NH in shitosan macromolecule segment2Active group, can send out with many kinds of metal ions
Raw complexation reaction, itself has excellent heavy metal ion adsorbed performance.The present invention is prepared by spray drying process has line shape
The small particle microballoon of edge structure, effectively increases adsorption area, exposes more graft sites.Dissaving polymer is a class
With highly branched and 3-D solid structure polymer, substantial amounts of active group is contained in end.The present invention is super by Amino End Group
Branched polymer is grafted, a large amount of acid amides and amino-functional group in microsphere surface grafting；Meanwhile, first prepare microballoon and be grafted work(again
Can group strategy also cause functional group farthest be exposed to microsphere surface, further enhancing microballoon heavy metal from
The adsorption effect of son.
The present invention is adopted the technical scheme that：A kind of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon heavy metal ion
The preparation method of adsorbent is comprised the following steps that：（1）It is 3 ~ 6 × 10 by viscosity average molecular weigh5Da, deacetylation is 75% ~ 97%
It is 1% ~ 2% that shitosan is dissolved in concentration（v/v）Acetic acid or lactic acid aqueous solution in, obtain concentration for 1% ~ 3%（w/v）Shitosan
Solution, unit is g/mL；Inlet temperature be 160 ~ 220 DEG C, outlet temperature be 80 ~ 100 DEG C under conditions of to chitosan solution
It is spray-dried, is prepared chitosan microball；（2）With methyl alcohol as medium, in N2Protection, 40 ~ 60 DEG C of constant temperature, speeds of agitator
Under conditions of 400 ~ 1000 rpm, there is Michael addition reaction in chitosan microball with methyl acrylate, and the reaction time is 36 ~ 60
H, collects microballoon, and absolute ethanol washing 3 ~ 6 times is dried in 30 ~ 70 DEG C of baking ovens, obtains intermediate product methyl acrylate grafted chitosan
Microballoon.（3）With methyl alcohol as medium, in N2Protection, under conditions of 40 ~ 60 DEG C of constant temperature, the rpm of speed of agitator 400 ~ 1000, acrylic acid
Methyl esters grafted chitosan microballoon reacts 48 ~ 96 h with diethylenetriamine, collects microballoon, absolute ethanol washing 3 ~ 6 times, 30 ~ 70 DEG C
Dried in baking oven, obtain Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon.
Step（2）In, content of the chitosan microball in METHANOL MEDIUM is 1 ~ 6 g/100mL.
Step（2）In, chitosan microball is 1 with the mass volume ratio of methyl acrylate:2~1:6, unit is g:mL.
Step（3）In, content of the methyl acrylate grafted chitosan microballoon in METHANOL MEDIUM is 1 ~ 6 g/100 mL.
Step（3）In, methyl acrylate grafted chitosan microballoon is 1 with the mass volume ratio of diethylenetriamine:8~1:40,
Unit is g:mL.
The positive effect of the present invention is as follows：Main raw material of chitosan used by the present invention is that content is only second to fibre in nature
The natural polysaccharide of element is tieed up, wide material sources are cheap；With good biocompatibility and nontoxicity, environment will not be caused
Secondary pollution；Contain a large amount of-OH and-NH in shitosan macromolecule segment2Active group, can match somebody with somebody with many kinds of metal ions
Position reaction, itself has excellent heavy metal ion adsorbed performance；The microballoon obtained by spray drying process has striated border knot
Structure, particle diameter is less than 15 μm, effectively increases specific surface area, exposes more graft sites；The balling-up of sorbing material elder generation, is followed by
Branch, can make grafted moiety be fully exposed to microsphere surface, effectively increase the utilization rate of grafted moiety；Amine-terminated hyperbrancedization is polymerized
After thing grafting so that microsphere surface contains substantial amounts of acid amides and amino, the absorption effect of microballoon heavy metal ion is effectively increased
Really.The present invention is the Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon with efficient heavy ionic adsorption performance, is prepared
Method is simple, and process stabilizing is cheap, is easy to industrialized production, and using safety, accumulating is convenient, with good society's effect
Benefit and economic benefit.
Specific embodiment：
A kind of preparation method of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon adsorbent for heavy metal, it is characterised in that
Comprise the following steps：（1）It is 3 ~ 6 × 10 by viscosity average molecular weigh5Da, deacetylation is dissolved in concentration for 75% ~ 97% shitosan
It is 1% ~ 2%（v/v）Acetic acid or lactic acid aqueous solution in, obtain concentration for 1% ~ 3%（w/v）Chitosan solution, unit is g/mL；
It it is 160 ~ 220 DEG C in inlet temperature, outlet temperature is prepared to be spray-dried to chitosan solution under conditions of 80 ~ 100 DEG C
Obtain chitosan microball；（2）With methyl alcohol as medium, in N2Protection, 40 ~ 60 DEG C of constant temperature, bars of the rpm of speed of agitator 400 ~ 1000
Under part, there is Michael addition reaction in chitosan microball with methyl acrylate, and the reaction time is 36 ~ 60 h, collects microballoon, anhydrous
Ethanol is washed 3 ~ 6 times, is dried in 30 ~ 70 DEG C of baking ovens, obtains intermediate product methyl acrylate grafted chitosan microballoon.（3）With methyl alcohol
It is medium, in N2Protection, under conditions of 40 ~ 60 DEG C of constant temperature, the rpm of speed of agitator 400 ~ 1000, methyl acrylate grafted chitosan
Microballoon reacts 48 ~ 96 h with diethylenetriamine, collects microballoon, and absolute ethanol washing 3 ~ 6 times is dried in 30 ~ 70 DEG C of baking ovens, must held
Amino grafted by super branched polymer chitosan microball.
Step of the present invention（2）In, content of the chitosan microball in METHANOL MEDIUM is 1 ~ 6 g/100mL；Chitosan microball
It is 1 with the mass volume ratio of methyl acrylate:2~1:6, unit is g:mL.Step（3）In, methyl acrylate grafted chitosan is micro-
Content of the ball in METHANOL MEDIUM is 1 ~ 6 g/100 mL；The quality of methyl acrylate grafted chitosan microballoon and diethylenetriamine
Volume ratio is 1:8~1:40, unit is g:mL.
Following specific embodiment further provides preparation method of the invention.
Embodiment 1.
It is 3 × 10 by viscosity average molecular weigh5Da, deacetylation is 96% g of shitosan 10, and it is 1% to be dissolved in 1000 mL concentration
（v/v）Acetic acid aqueous solution in, obtain concentration for 1%（w/v）Chitosan solution；It is 220 DEG C, outlet temperature in inlet temperature
To be spray-dried to chitosan solution under conditions of 100 DEG C, collection obtains chitosan microball.5 g chitosan microballs are taken to add
Enter in 100 mL methyl alcohol, in N2Under conditions of protection, 40 DEG C of constant temperature, the rpm of speed of agitator 800,20 mL acrylic acid first are added
Ester, reacts 60 h, collects microballoon, and absolute ethanol washing 6 times is dried in 50 DEG C of baking ovens, obtains the grafting of intermediate product methyl acrylate
Chitosan microball.Take 1.5 g methyl acrylate grafted chitosan microballoons to be added in 100 mL methyl alcohol, in N2Protection, 40 DEG C of perseverances
Under conditions of temperature, the rpm of speed of agitator 800, add 20 mL diethylenetriamines to react 72 h, collect microballoon, absolute ethanol washing 6
It is secondary, dried in 70 DEG C of baking ovens, obtain Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon.The particle size range of the microballoon is 1 ~ 8 μ
M, 3.2 μm of average grain diameter, at being 5.8,25 DEG C in pH, in unitary system, to Pb2+Adsorption capacity be 233 ± 12.19 mg/
G, to Cu2+Adsorption capacity be 222 ± 14.33 mg/g, to Cd2+Adsorption capacity be 201 ± 11.19 mg/g.
Embodiment 2.
It is 6 × 10 by viscosity average molecular weigh5Da, deacetylation is 85% g of shitosan 10, and it is 2% to be dissolved in 500 mL concentration（v/
v）Acetic acid aqueous solution in, obtain concentration for 2%（w/v）Chitosan solution；It it is 180 DEG C in inlet temperature, outlet temperature is 90
Chitosan solution is spray-dried under conditions of DEG C, collection obtains chitosan microball.6 g chitosan microballs are taken to be added to
In 100 mL methyl alcohol, in N2Under conditions of protection, 60 DEG C of constant temperature, the rpm of speed of agitator 1000,18 mL methyl acrylates are added,
40 h are reacted, microballoon is collected, absolute ethanol washing 3 times is dried in 70 DEG C of baking ovens, is obtained intermediate product methyl acrylate graft shell and is gathered
Sugared microballoon.Take 3 g methyl acrylate grafted chitosan microballoons to be added in 100 mL methyl alcohol, in N2Protection, 60 DEG C of constant temperature, stirrings
Under conditions of the rpm of rotating speed 1000, add 30 mL diethylenetriamines to react 86 h, collect microballoon, absolute ethanol washing 6 times, 70
Dried in DEG C baking oven, obtain Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon.The particle size range of the microballoon is 2 ~ 11 μm, is put down
Equal 4.8 μm of particle diameter, at being 5.8,25 DEG C in pH, in unitary system, to Pb2+Adsorption capacity be 212 ± 15.37 mg/g, it is right
Cu2+Adsorption capacity be 201 ± 11.43 mg/g, to Cd2+Adsorption capacity be 189 ± 9.13 mg/g.
Embodiment 3.
It is 5 × 10 by viscosity average molecular weigh5Da, deacetylation is 93% g of shitosan 20, and it is 2% to be dissolved in 1000 mL concentration
（v/v）Lactic acid aqueous solution in, obtain concentration for 2%（w/v）Chitosan solution；It is 210 DEG C, outlet temperature in inlet temperature
To be spray-dried to chitosan solution under conditions of 100 DEG C, collection obtains chitosan microball.10 g chitosan microballs are taken to add
Enter in 1000 mL methyl alcohol, in N2Under conditions of protection, 60 DEG C of constant temperature, the rpm of speed of agitator 1000,60 mL acrylic acid are added
Methyl esters, reacts 60 h, collects microballoon, and absolute ethanol washing 3 times is dried in 60 DEG C of baking ovens, obtains intermediate product methyl acrylate and connect
Branch chitosan microball.Take 5 g methyl acrylate grafted chitosan microballoons to be added in 500 mL methyl alcohol, in N2Protection, 60 DEG C of perseverances
Under conditions of temperature, the rpm of speed of agitator 1000, add 200 mL diethylenetriamines to react 96 h, collect microballoon, absolute ethyl alcohol is washed
Wash 6 times, dried in 60 DEG C of baking ovens, obtain Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon.The particle size range of the microballoon be 2 ~
10 μm, 4.6 μm of average grain diameter, at being 5.8,25 DEG C in pH, in unitary system, to Pb2+Adsorption capacity be 255 ± 9.37
Mg/g, to Cu2+Adsorption capacity be 238 ± 9.86 mg/g, to Cd2+Adsorption capacity be 231 ± 16.53 mg/g.
Embodiment 4.
It is 3.5 × 10 by viscosity average molecular weigh5Da, deacetylation is 80% g of shitosan 4.5, and it is 1% to be dissolved in 300 mL concentration
（v/v）Acetic acid aqueous solution in, obtain concentration for 1.5%（w/v）Chitosan solution；It is 190 DEG C in inlet temperature, outlet temperature
Spend to be spray-dried to chitosan solution under conditions of 90 DEG C, collection obtains chitosan microball.3 g chitosan microballs are taken to add
Enter in 100 mL methyl alcohol, in N2Under conditions of protection, 50 DEG C of constant temperature, the rpm of speed of agitator 500,15 mL acrylic acid first are added
Ester, reacts 48 h, collects microballoon, and absolute ethanol washing 5 times is dried in 50 DEG C of baking ovens, obtains the grafting of intermediate product methyl acrylate
Chitosan microball.Take 2 g methyl acrylate grafted chitosan microballoons to be added in 100 mL methyl alcohol, in N2Protection, 60 DEG C of constant temperature,
Under conditions of the rpm of speed of agitator 500, addition 40 mL diethylenetriamines, 80 h of reaction, collection microballoon, absolute ethanol washing 5 times,
Dried in 50 DEG C of baking ovens, obtain Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon.The particle size range of the microballoon is 1 ~ 10 μm,
3.8 μm of average grain diameter, at being 5.8,25 DEG C in pH, in unitary system, to Pb2+Adsorption capacity be 241 ± 13.26 mg/g,
To Cu2+Adsorption capacity be 224 ± 12.85 mg/g, to Cd2+Adsorption capacity be 219 ± 7.31 mg/g.
Claims (5)
1. a kind of preparation method of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon adsorbent for heavy metal, its feature exists
In comprising the following steps：
（1）It is 3 ~ 6 × 10 by viscosity average molecular weigh5 Da, deacetylation is dissolved in concentration for 1% ~ 2% for 75% ~ 97% shitosan（v/
v）Acetic acid or lactic acid aqueous solution in, obtain concentration for 1% ~ 3%（w/v）Chitosan solution, unit is g/mL；In inlet temperature
It it is 160 ~ 220 DEG C, outlet temperature prepares shitosan to be spray-dried to chitosan solution under conditions of 80 ~ 100 DEG C
Microballoon；
（2）With methyl alcohol as medium, in N2Under conditions of protection, 40 ~ 60 DEG C of constant temperature, the rpm of speed of agitator 400 ~ 1000, shitosan is micro-
There is Michael addition reaction in ball, the reaction time is 36 ~ 60 h, collects microballoon, absolute ethanol washing 3 ~ 6 with methyl acrylate
It is secondary, dried in 30 ~ 70 DEG C of baking ovens, obtain intermediate product methyl acrylate grafted chitosan microballoon；
（3）With methyl alcohol as medium, in N2Protection, under conditions of 40 ~ 60 DEG C of constant temperature, the rpm of speed of agitator 400 ~ 1000, acrylic acid first
Ester grafted chitosan microballoon reacts 48 ~ 96 h with diethylenetriamine, collects microballoon, absolute ethanol washing 3 ~ 6 times, 30 ~ 70 DEG C of bakings
Dried in case, obtain Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon.
2. as claimed in claim 1 a kind of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon adsorbent for heavy metal
Preparation method, it is characterised in that step（2）In, content of the chitosan microball in METHANOL MEDIUM is 1 ~ 6 g/100 mL.
3. as claimed in claim 1 a kind of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon adsorbent for heavy metal
Preparation method, it is characterised in that step（2）In, chitosan microball is 1 with the mass volume ratio of methyl acrylate:2~1:6, unit
It is g:mL.
4. as claimed in claim 1 a kind of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon adsorbent for heavy metal
Preparation method, it is characterised in that step（3）In, content of the methyl acrylate grafted chitosan microballoon in METHANOL MEDIUM is 1 ~ 6
g/100 mL。
5. as claimed in claim 1 a kind of Hyperbranched Polymer with Terminal Amido grafted chitosan microballoon adsorbent for heavy metal
Preparation method, it is characterised in that step（3）In, the mass volume ratio of methyl acrylate grafted chitosan microballoon and diethylenetriamine
It is 1:8~1:40, unit is g:mL.
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| CN112586712A (en) * | 2020-12-07 | 2021-04-02 | 安徽省美极调味食品有限公司 | Wet diced meat seasoning capable of being stored at normal temperature and preparation method thereof |
| CN112961344A (en) * | 2021-02-07 | 2021-06-15 | 威海金泓集团有限公司 | Chitosan-based hyperbranched polyamide compound and application thereof |
| CN113754892A (en) * | 2020-06-05 | 2021-12-07 | 中国石油天然气集团有限公司 | Hyperbranched polymer grafted chitosan and preparation and application thereof |
| CN114957650A (en) * | 2022-06-11 | 2022-08-30 | 田钟 | Preparation method of polyaspartic acid potassium and application of polyaspartic acid potassium in plant growth promoter |
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| CN113754892A (en) * | 2020-06-05 | 2021-12-07 | 中国石油天然气集团有限公司 | Hyperbranched polymer grafted chitosan and preparation and application thereof |
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| CN114957650A (en) * | 2022-06-11 | 2022-08-30 | 田钟 | Preparation method of polyaspartic acid potassium and application of polyaspartic acid potassium in plant growth promoter |
| CN114957650B (en) * | 2022-06-11 | 2024-05-10 | 新疆腾域鸿源农业科技有限公司 | Preparation method of potassium polyaspartate and application of potassium polyaspartate in plant growth promoter |
| CN115159928A (en) * | 2022-07-25 | 2022-10-11 | 贵阳中建西部建设有限公司 | Low-carbon green lightweight concrete aggregate and preparation method thereof |
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