CN105013455A - Carboxyl terminated dendritic polymer adsorption material and preparation method thereof - Google Patents

Carboxyl terminated dendritic polymer adsorption material and preparation method thereof Download PDF

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Publication number
CN105013455A
CN105013455A CN201510379076.4A CN201510379076A CN105013455A CN 105013455 A CN105013455 A CN 105013455A CN 201510379076 A CN201510379076 A CN 201510379076A CN 105013455 A CN105013455 A CN 105013455A
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dendritic
hydroxy group
terminal hydroxy
crude product
dendritic polymer
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CN105013455B (en
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强涛涛
李小宁
赵静
任龙芳
王学川
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Shanghai Qiuqiuyun Environmental Protection Technology Co ltd
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Shaanxi University of Science and Technology
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Abstract

The invention relates to a carboxyl terminated dendritic polymer adsorption material and a preparation method thereof. The dendritic polymer has a network spherical three-dimensional structure, and can greatly improve the adsorption efficiency as an adsorption material. The preparation method includes: dissolving cyanuric chloride in acetone or tetrahydrofuran, adding the mixture into an acetone solution of diol to obtain a primary hydroxy terminated dendritic polymer crude product, conducting purification to obtain a primary hydroxy terminated dendritic polymer; taking cyanuric chloride as the core, adopting the primary hydroxy terminated dendritic polymer as the branching unit to prepare a secondary hydroxy terminated dendritic polymer crude product and a tertiary hydroxy terminated dendritic polymer crude product, and carrying out purification; and dispersing the hydroxy terminated dendritic polymer in water, adding maleic anhydride and p-toluenesulfonic acid to prepare a carboxyl terminated dendritic polymer crude product, and conducting purification to obtain the carboxyl terminated dendritic polymer adsorption material. The method provided by the invention has the characteristics of mild conditions, simple process and short production cycle. The product contains a lot of active carboxyl terminal groups, has strong adsorption performance, and is expected to be used in heavy metal ion and organic wastewater treatment and other fields.

Description

End carboxyl dendritic sorbing material and preparation method thereof
Technical field
the present invention relates to technical field of polymer materials, be specifically related to a kind of end carboxyl dendritic sorbing material and preparation method thereof.
Background technology
Compared with other method for treating water, absorption method has the advantages such as clearance is high, easy and simple to handle, adsorbent is renewable, is widely used in the process of low concentration wastewater, especially heavy metal ion and organic matter.Conventional adsorbent mainly contains active carbon, resin and natural mineral matter etc., high performance adsorbent mostly is the polymeric material of Prof. Du Yucang, if active carbon is a kind of porous carbon, bulk density is low, the adsorbent that specific area is large, but for some heavy metal ion and less, selective lower, the adsorbent material regeneration difficulty of Adsorption of Organic capacity relative, the application of distance actual industrialization also has certain distance.
Dendritic is that one is rich in various functional end-group, has the macromolecular structure polymer of the spherical 3-D solid structure of similar network.Compare linear polymer, highly branched structure polymer molecular structure is spherical in shape, and there is a large amount of cavity inside, and active reaction sites is many, its functioning efficiency can be made greatly to improve as sorbing material.
Summary of the invention
The object of this invention is to provide a kind of end carboxyl dendritic sorbing material and preparation method thereof, the obtained sorbing material containing more end carboxyl, improving its absorption property, providing more selection for adsorbing industry.
The technical solution adopted in the present invention is:
The preparation method of end carboxyl dendritic sorbing material, is characterized in that:
Comprise the following steps:
1) preparation of terminal hydroxy group dendritic:
The first step: take 5-10mmol dihydroxylic alcohols and be dissolved in 40-80mL acetone; Be (3-4) according to dihydroxylic alcohols and cyanuric trichloride mol ratio: the ratio of 1, is dissolved in cyanuric trichloride in 50-100mL acetone or oxolane, dropwise join in the acetone soln of dihydroxylic alcohols under the condition of nitrogen protection and ice-water bath; Stirring reaction 1-3h, is slowly warming up to 40-50 DEG C, and stirring reaction 2-6h, is finally warmed up to 85-95 DEG C, stirring reaction 3-9h, and constantly adding acid binding agent maintenance pH in reaction is 5-6, obtained generation terminal hydroxy group dendritic crude product;
Second step: by obtained generation terminal hydroxy group dendritic crude product through acetone extracting and washing repeatedly, and namely vacuum filtration obtains generation terminal hydroxy group dendritic;
3rd step: take cyanuric trichloride as core, generation terminal hydroxy group dendritic is branching unit, the first step prepared according to terminal hydroxy group dendritic repeats to implement, obtained two generations, three generations's terminal hydroxy group dendritic crude product, method of purification is prepared described in second step with terminal hydroxy group dendritic;
2) preparation of end carboxyl dendritic:
The first step: take 5-10mmol three generations terminal hydroxy group dendritic and be scattered in 40-80mL water; Be (1-1.5) according to maleic anhydride and hydroxyl mol ratio: the ratio of 1 adds maleic anhydride, then to add with reactant be Reference mass ratio be the p-methyl benzenesulfonic acid of 0.3 ~ 0.5%, be warming up to 70-90 DEG C of insulation reaction 3-5h; Obtained end carboxyl dendritic crude product;
Second step, by obtained end carboxyl dendritic crude product through distilled water cyclic washing, and namely vacuum filtration obtains end carboxyl dendritic sorbing material.
In the first step of step 1), dihydroxylic alcohols is ethylene glycol, 1,3-PD, BDO, 1,5-PD or 1,6-hexylene glycol.
In the first step of step 1), acid binding agent is NaOH, sodium carbonate or pyridine.
As described in the sorbing material that obtains of the preparation method of end carboxyl dendritic sorbing material.
The present invention has the following advantages:
1, advantages of good adsorption effect: because there is cavity structure dendritic inside, hang can roll into a ball containing multiple end, active reaction sites is many, its functioning efficiency can be made greatly to improve as sorbing material.
2, consumption is few, cost is low: end carboxyl dendritic relative molecular mass is comparatively large, and molecular structure is special, under the same conditions, only needs common adsorbents as 1/3rd of activated carbon dosage, and the easy wash-out of sorbing material, sorbing material reusable edible.
3, the scope of application is wide: this sorbing material can be used for different industries heavy metal ions in wastewater and the organic process such as dyestuff, surfactant.
Experimental result shows: this end carboxyl dendritic heavy metal cation, basic dyestuff, cationic surface active agent all have good removal effect.Under weak basic condition, 0.2g sorbing material is to the Cu of 100mg/L 2+clearance can reach more than 90.4%; Under comparatively strong alkaline condition, can more than 95.8% be reached to the clearance of the basic fuchsin of 500mg/L; For the DTAB (DTB) of 500mg/L, clearance is 93.2%.
Accompanying drawing explanation
Fig. 1 is the synthesis of generation terminal hydroxy group dendritic.
Fig. 2 is the synthesis of two generations and three generations's terminal hydroxy group dendritic.
Fig. 3 is that end carboxyl dendritic is prepared in modification.
Detailed description of the invention
Below in conjunction with detailed description of the invention, the present invention will be described in detail.
The present invention relates to the preparation method of end carboxyl dendritic sorbing material, comprise the following steps:
1) preparation of terminal hydroxy group dendritic:
The first step: take 5-10mmol dihydroxylic alcohols and be dissolved in 40-80mL acetone; Be (3-4) according to dihydroxylic alcohols and cyanuric trichloride mol ratio: the ratio of 1, is dissolved in cyanuric trichloride in 50-100mL acetone or oxolane, dropwise join in the acetone soln of dihydroxylic alcohols under the condition of nitrogen protection and ice-water bath; Stirring reaction 1-3h, is slowly warming up to 40-50 DEG C, and stirring reaction 2-6h, is finally warmed up to 85-95 DEG C, stirring reaction 3-9h, and constantly adding acid binding agent maintenance pH in reaction is 5-6, obtained generation terminal hydroxy group dendritic crude product;
Second step: by obtained generation terminal hydroxy group dendritic crude product through acetone extracting and washing repeatedly, and namely vacuum filtration obtains generation terminal hydroxy group dendritic;
3rd step: take cyanuric trichloride as core, generation terminal hydroxy group dendritic is branching unit, the first step prepared according to terminal hydroxy group dendritic repeats to implement, obtained two generations, three generations's terminal hydroxy group dendritic crude product, method of purification is prepared described in second step with terminal hydroxy group dendritic;
2) preparation of end carboxyl dendritic:
The first step: take 5-10mmol terminal hydroxy group dendritic and be scattered in 40-80mL water; Be (1-1.5) according to maleic anhydride and hydroxyl mol ratio: the ratio of 1 adds maleic anhydride, then to add with reactant be Reference mass ratio be the p-methyl benzenesulfonic acid of 0.3 ~ 0.5%, be warming up to 70-90 DEG C of insulation reaction 3-5h; Obtained end carboxyl dendritic crude product;
Second step, by obtained end carboxyl dendritic crude product through distilled water cyclic washing, and namely vacuum filtration obtains end carboxyl dendritic sorbing material.
In the first step of step 1), dihydroxylic alcohols is ethylene glycol, 1,3-PD, BDO, 1,5-PD or 1,6-hexylene glycol.
In the first step of step 1), acid binding agent is NaOH, sodium carbonate or pyridine.
The present invention is core with cyanuric trichloride, take aliphatic dihydroxy alcohol as branching unit, first synthesizes terminal hydroxy group dendritic, then is modifying agent with maleic anhydride, prepare end carboxyl dendritic, and existing for ethylene glycol, its reaction equation as Figure 1-3.
Embodiment 1:
1) preparation of terminal hydroxy group dendritic:
The first step: take 5mmol dihydroxylic alcohols and be dissolved in 80mL acetone; Be the ratio of 3:1 according to dihydroxylic alcohols and cyanuric trichloride mol ratio, cyanuric trichloride be dissolved in 100mL acetone, dropwise join in the acetone soln of dihydroxylic alcohols under the condition of nitrogen protection and ice-water bath; Stirring reaction 1h, is slowly warming up to 50 DEG C, and stirring reaction 2h is finally warmed up to 95 DEG C, stirring reaction 3h, and constantly adding acid binding agent maintenance pH in reaction is 6, obtained generation terminal hydroxy group dendritic crude product;
Second step: by obtained generation terminal hydroxy group dendritic crude product through acetone extracting and washing repeatedly, and namely vacuum filtration obtains generation terminal hydroxy group dendritic;
3rd step: take cyanuric trichloride as core, generation terminal hydroxy group dendritic is branching unit, the first step prepared according to terminal hydroxy group dendritic repeats to implement, obtained two generations, three generations's terminal hydroxy group dendritic crude product, method of purification is prepared described in second step with terminal hydroxy group dendritic;
2) preparation of end carboxyl dendritic:
The first step: take 5mmol terminal hydroxy group dendritic and be scattered in 80mL water; The ratio being 1:1 according to maleic anhydride and hydroxyl mol ratio adds maleic anhydride, then add add again with reactant be Reference mass than the p-methyl benzenesulfonic acid p-methyl benzenesulfonic acid being 0.3%, be warming up to 90 DEG C of insulation reaction 3h; Obtained end carboxyl dendritic crude product;
Second step, by obtained end carboxyl dendritic crude product through distilled water cyclic washing, and namely vacuum filtration obtains end carboxyl dendritic sorbing material.
In the first step of step 1), dihydroxylic alcohols is ethylene glycol or 1,3-PD.
In the first step of step 1), acid binding agent is NaOH.
Embodiment 2:
1) preparation of terminal hydroxy group dendritic:
The first step: take 7mmol dihydroxylic alcohols and be dissolved in 60mL acetone; Be the ratio of 3.5:1 according to dihydroxylic alcohols and cyanuric trichloride mol ratio, cyanuric trichloride be dissolved in 75mL acetone, dropwise join in the acetone soln of dihydroxylic alcohols under the condition of nitrogen protection and ice-water bath; Stirring reaction 2h, is slowly warming up to 45 DEG C, and stirring reaction 4h is finally warmed up to 90 DEG C, stirring reaction 6h, and constantly adding acid binding agent maintenance pH in reaction is 5, obtained generation terminal hydroxy group dendritic crude product;
Second step: by obtained generation terminal hydroxy group dendritic crude product through acetone extracting and washing repeatedly, and namely vacuum filtration obtains generation terminal hydroxy group dendritic;
3rd step: take cyanuric trichloride as core, generation terminal hydroxy group dendritic is branching unit, the first step prepared according to terminal hydroxy group dendritic repeats to implement, obtained two generations, three generations's terminal hydroxy group dendritic crude product, method of purification is prepared described in second step with terminal hydroxy group dendritic;
2) preparation of end carboxyl dendritic:
The first step: take 7mmol terminal hydroxy group dendritic and be scattered in 60mL water; The ratio being 1.2:1 according to maleic anhydride and hydroxyl mol ratio adds maleic anhydride, then add with reactant be Reference mass than the p-methyl benzenesulfonic acid being 0.4%, be warming up to 80 DEG C of insulation reaction 4h; Obtained end carboxyl dendritic crude product;
Second step, by obtained end carboxyl dendritic crude product through distilled water cyclic washing, and namely vacuum filtration obtains end carboxyl dendritic sorbing material.
In the first step of step 1), dihydroxylic alcohols is BDO or 1,5-PD.
In the first step of step 1), acid binding agent is sodium carbonate.
Embodiment 3:
1) preparation of terminal hydroxy group dendritic:
The first step: take 10mmol dihydroxylic alcohols and be dissolved in 40mL acetone; Be the ratio of 4:1 according to dihydroxylic alcohols and cyanuric trichloride mol ratio, cyanuric trichloride be dissolved in 50mL oxolane, dropwise join in the acetone soln of dihydroxylic alcohols under the condition of nitrogen protection and ice-water bath; Stirring reaction 3h, is slowly warming up to 40 DEG C, and stirring reaction 6h is finally warmed up to 85 DEG C, stirring reaction 9h, and constantly adding acid binding agent maintenance pH in reaction is 5, obtained generation terminal hydroxy group dendritic crude product;
Second step: by obtained generation terminal hydroxy group dendritic crude product through acetone extracting and washing repeatedly, and namely vacuum filtration obtains generation terminal hydroxy group dendritic;
3rd step: take cyanuric trichloride as core, generation terminal hydroxy group dendritic is branching unit, the first step prepared according to terminal hydroxy group dendritic repeats to implement, obtained two generations, three generations's terminal hydroxy group dendritic crude product, method of purification is prepared described in second step with terminal hydroxy group dendritic;
2) preparation of end carboxyl dendritic:
The first step: take 10mmol terminal hydroxy group dendritic and be scattered in 40mL water; The ratio being 1.5:1 according to maleic anhydride and hydroxyl mol ratio adds maleic anhydride, then add with reactant be Reference mass than the p-methyl benzenesulfonic acid being 0.5%, be warming up to 70 DEG C of insulation reaction 5h; Obtained end carboxyl dendritic crude product;
Second step, by obtained end carboxyl dendritic crude product through distilled water cyclic washing, and namely vacuum filtration obtains end carboxyl dendritic sorbing material.
In the first step of step 1), dihydroxylic alcohols is 1,6-hexylene glycol.
In the first step of step 1), acid binding agent is pyridine.
Content of the present invention is not limited to cited by embodiment, and the conversion of those of ordinary skill in the art by reading description of the present invention to any equivalence that technical solution of the present invention is taked, is claim of the present invention and contains.

Claims (4)

1. the preparation method of end carboxyl dendritic sorbing material, is characterized in that:
Comprise the following steps:
1) preparation of terminal hydroxy group dendritic:
The first step: take 5-10mmol dihydroxylic alcohols and be dissolved in 40-80mL acetone; Be (3-4) according to dihydroxylic alcohols and cyanuric trichloride mol ratio: the ratio of 1, is dissolved in cyanuric trichloride in 50-100mL acetone or oxolane, dropwise join in the acetone soln of dihydroxylic alcohols under the condition of nitrogen protection and ice-water bath; Stirring reaction 1-3h, is slowly warming up to 40-50 DEG C, and stirring reaction 2-6h, is finally warmed up to 85-95 DEG C, stirring reaction 3-9h, and constantly adding acid binding agent maintenance pH in reaction is 5-6, obtained generation terminal hydroxy group dendritic crude product;
Second step: by obtained generation terminal hydroxy group dendritic crude product through acetone extracting and washing repeatedly, and namely vacuum filtration obtains generation terminal hydroxy group dendritic;
3rd step: take cyanuric trichloride as core, generation terminal hydroxy group dendritic is branching unit, the first step prepared according to terminal hydroxy group dendritic repeats to implement, obtained two generations, three generations's terminal hydroxy group dendritic crude product, method of purification is prepared described in second step with terminal hydroxy group dendritic;
2) preparation of end carboxyl dendritic:
The first step: take 5-10mmol three generations terminal hydroxy group dendritic and be scattered in 40-80mL water; Be (1-1.5) according to maleic anhydride and hydroxyl mol ratio: the ratio of 1 adds maleic anhydride, then to add with reactant be Reference mass ratio be the p-methyl benzenesulfonic acid of 0.3 ~ 0.5%, be warming up to 70-90 DEG C of insulation reaction 3-5h; Obtained end carboxyl dendritic crude product;
Second step, by obtained end carboxyl dendritic crude product through distilled water cyclic washing, and namely vacuum filtration obtains end carboxyl dendritic sorbing material.
2. the preparation method of end carboxyl dendritic sorbing material according to claim 1, is characterized in that:
In the first step of step 1), dihydroxylic alcohols is ethylene glycol, 1,3-PD, BDO, 1,5-PD or 1,6-hexylene glycol.
3. the preparation method of end carboxyl dendritic sorbing material according to claim 2, is characterized in that:
In the first step of step 1), acid binding agent is NaOH, sodium carbonate or pyridine.
4. the sorbing material that obtains of the preparation method of end carboxyl dendritic sorbing material as claimed in claim 3.
CN201510379076.4A 2015-07-02 2015-07-02 Carboxyl terminated dendritic polymer adsorption material and preparation method thereof Active CN105013455B (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109071807A (en) * 2016-02-09 2018-12-21 日产化学株式会社 Polymer containing triazine ring and the composition comprising the polymer
CN111995714A (en) * 2020-03-25 2020-11-27 武汉纺织大学 Flexible hydrophilic polymer with anion and cation adsorption-desorption functions and preparation method and application thereof
CN115246935A (en) * 2022-02-10 2022-10-28 王芳 Light high-temperature-resistant plastic and preparation method thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101417984A (en) * 2008-12-15 2009-04-29 苏州大学 A kind of initiated core and application thereof that contains triazine ring
CN101643651A (en) * 2009-08-25 2010-02-10 四川大学 Macromolecular intumescent flame resistance carbonizing agent with branching and crosslinking structure and preparation method and application thereof
US20100093094A1 (en) * 2008-08-27 2010-04-15 Thomas Kissel Triazine dendrimers and methods of making and using the same for nucleic acid transport
CN102181073A (en) * 2011-02-14 2011-09-14 福建师范大学 Triazine compound coordination crosslinking synergistic agent for elastomer and preparation method thereof
CN102600809A (en) * 2012-03-16 2012-07-25 陕西科技大学 Amino end-group triazine ring tree-shaped macromolecular adsorbent and preparation method thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100093094A1 (en) * 2008-08-27 2010-04-15 Thomas Kissel Triazine dendrimers and methods of making and using the same for nucleic acid transport
CN101417984A (en) * 2008-12-15 2009-04-29 苏州大学 A kind of initiated core and application thereof that contains triazine ring
CN101643651A (en) * 2009-08-25 2010-02-10 四川大学 Macromolecular intumescent flame resistance carbonizing agent with branching and crosslinking structure and preparation method and application thereof
CN102181073A (en) * 2011-02-14 2011-09-14 福建师范大学 Triazine compound coordination crosslinking synergistic agent for elastomer and preparation method thereof
CN102600809A (en) * 2012-03-16 2012-07-25 陕西科技大学 Amino end-group triazine ring tree-shaped macromolecular adsorbent and preparation method thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109071807A (en) * 2016-02-09 2018-12-21 日产化学株式会社 Polymer containing triazine ring and the composition comprising the polymer
CN111995714A (en) * 2020-03-25 2020-11-27 武汉纺织大学 Flexible hydrophilic polymer with anion and cation adsorption-desorption functions and preparation method and application thereof
CN111995714B (en) * 2020-03-25 2022-05-13 武汉纺织大学 Flexible hydrophilic polymer with anion and cation adsorption-desorption function and preparation method and application thereof
CN115246935A (en) * 2022-02-10 2022-10-28 王芳 Light high-temperature-resistant plastic and preparation method thereof

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