CN103193824A - Functional monomer and preparation method thereof - Google Patents
Functional monomer and preparation method thereof Download PDFInfo
- Publication number
- CN103193824A CN103193824A CN2013101411073A CN201310141107A CN103193824A CN 103193824 A CN103193824 A CN 103193824A CN 2013101411073 A CN2013101411073 A CN 2013101411073A CN 201310141107 A CN201310141107 A CN 201310141107A CN 103193824 A CN103193824 A CN 103193824A
- Authority
- CN
- China
- Prior art keywords
- general formula
- function monomer
- chooses
- preparation
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 0 *C(C(OCN=C)=O)=[N+][I-] Chemical compound *C(C(OCN=C)=O)=[N+][I-] 0.000 description 1
Abstract
The invention provides a functional monomer. The molecular structure of the functional monomer comprises a quaternary ammonium salt structural unit and a salophen complex or a Salen complex unit; and the functional monomer can self polymerize as well as copolymerize with styrene, acrylic ester, acrylonitrile, vinyl acetate or acrylamide, and is used for preparing ion imprinted polymers having the functions of identifying, detecting and separating heavy metal ions. The functional monomer has high hydrophilicity, and moreover, the salophen complex or the Salen complex of the functional monomer also forms the core of the imprinting function and the identification function of the metal ion imprinted polymers.
Description
Technical field
The present invention relates to a kind of function monomer, particularly contain the function monomer of quaternary ammonium salt and salophen title complex or Salen title complex in the molecular structure, for the preparation of the metal ion imprinted polymer, belong to functional high polymer material field.
Technical background
Imprinted polymer refers to that with a certain specific target molecule be template, be combined with template molecule by interact (coordinate bond, hydrogen bond, Van der Waals force, electrostatic interaction, hydrophobic interaction etc.) having complementary function monomer on the structure, add linking agent and carry out polyreaction, after reaction is finished, the template molecule wash-out is come out, form the identical hole of a kind of size or shape and template molecule, can identify the rigid polymer material that adsorbs the template template molecule by highly selective.The metal ion imprinted polymer is to be template with the metal ion, interacts by effects such as static, coordination and the function monomer that has dentate, and is got off by " memory " by polymerization process.Ionic linkage between coordination function monomer and the metal ion and coordinate bond have stronger reactive force than hydrogen bond, Van der Waals force, electrostatic interaction, hydrophobic interaction etc., space structure is stable, directional property is strong, is conducive to prepare imprinted polymer highly selective, the trace function-stable; Recognition process by coordination has in conjunction with quick and reversible advantage; In addition, metallic ion coordination acts in the polar system can stable existence, and this just makes the preparation of water-soluble template and imprinted polymer and application become possibility; Usually be that the transition metal ion coordination has good thermodynamic stability, than being easier to reach kinetic balance, have wide range of applications.
Although the engram technology development rapidly, and obtain using more widely, but still have a lot of problems.One of them be present spendable function monomer kind very little, the function singleness of function monomer to such an extent as to can not satisfy the requirement of some templates identification, maybe can not satisfy the needs of practical application; Imprinted polymer can only carry out polymerization and application mostly in organic phase in addition, and natural template recognition system is carried out in the aqueous solution mostly, how can carry out template imprinting in the aqueous solution or in the polar solvent and identification is still a great problem.So synthetic more, the better function monomer of performance of kind, the trace of template and recognition process turn to water to have important and practical meanings from organic phase.
Summary of the invention
The invention provides a kind of function monomer, for the preparation of the transition metal ion imprinted polymer, described ion imprinted polymer has the function of identification, detection, separation and enrichment transition metal ion; The acryl that contains quaternary ammonium salt, salophen title complex or Salen title complex in the molecular structure of described function monomer and participate in polyreaction.Function monomer provided by the invention, its feature have chemical structure shown in the general formula (I):
R in its formula of (I) chooses H or methyl, R
1And R
2Choose C respectively
1～C
18A kind of in the alkyl, Y chooses O or NH, and n chooses a kind of in 2,3,4,5 or 6, and Z chooses C
2～C
6A kind of in alkyl, phenyl ring, naphthalene nucleus or the pyridine ring, X
-Be selected from F
-, Cl
-, Br
-, I
-, HSO
4 -, H
2PO
4 -Or CH
3COO
-In a kind of, M is selected from transition metal ion, L is selected from one or more in water, methyl alcohol, ethanol, acetone, acrylamide, 2-Methacrylamide, propylene hydrazides, 2-methacrylic hydrazides, vinylformic acid, 2-methacrylic acid, 1-vinyl imidazole, 1-allyl imidazole, 4-vinylpridine, 2-vinyl pyridine, N-(4-ethenylphenyl) imines diacetic acid, allyl sulphonic acid or the 5-vinyl salicylic aldehyde, and m is selected from a kind of in 0,1,2 or 3.
General formula provided by the invention (I) function monomer has following feature:
1. the quaternary ammonium salt structure unit in described general formula (I) the function monomer molecular structure, has strongly hydrophilic, by its metal ion imprinted polymer surface hydrophilicity height that makes, described metal ion imprinted polymer can carry out at aqueous phase the absorption of metal ion, and reaches adsorption equilibrium rapidly.
2. the salophen title complex of described general formula (I) function monomer or Salen title complex are the trace function that constitutes the metal ion imprinted polymer, " core " structural unit of recognition function, Hg
2+, pb
2+, Cr
3+, Cd
2+, Cu
2+, Fe
3+, Zn
2+, Ni
2+, Ag
+, Pt
2+, Pd
2+, Mn
2+, UO
2 2+Or RE
3+Etc. the color and luster of transition metal ion salophen title complex or Salen title complex different, fluorescence strengthens or the fluorescent quenching phenomenon changes various.
The invention has the beneficial effects as follows:
1. described general formula (I) function monomer can carry out self-polymeric reaction or copolyreaction, can be used for preparing water-soluble or hydrophilic ionic polymer or metal ion imprinted polymer material as function monomer.
2. described general formula (I) function monomer is solid matter, stores the transportation stability height, and is safe and convenient to use.
3. the method for preparing described general formula (I) function monomer is simple, and starting material are the commercial goods, and the source is abundant, and each step reaction product yield height does not have three-waste pollution.
4. the metal ion imprinted polymer that constitutes of described general formula (I) function monomer adsorbs colour-change behind a kind of transition metal ion and fluorescent characteristic and changes variously, changes to indicate kind, valence state and the absorption degree of saturation that ion imprinted polymer adsorbs described transition metal ion according to color and luster.
5. also has the anionresin function by the prepared metal ion imprinted polymer material of general formula provided by the invention (I) function monomer.
The method for preparing structure function monomer shown in the general formula (I) realizes through following synthetic route and preparation process:
Wherein in said synthesis route, described R chooses H or methyl, described R
1And R
2Choose C respectively
1～C
18A kind of in the alkyl, n choose a kind of in 2,3,4,5 or 6, and described Y chooses O or NH, and described Z chooses C
2～C
6A kind of in alkyl, phenyl ring, naphthalene nucleus or the pyridine ring, described MX
pIn M refer to metal ion, described MX
pIn X refer to F
-, Cl
-, Br
-, I
-, HSO
4 -, H
2PO
4 -Or CH
3COO
-In a kind of, described MX
pIn p refer to a kind of in 1,2,3 or 4, described L is selected from one or more in water, methyl alcohol, ethanol, acetone, acrylamide, 2-Methacrylamide, propylene hydrazides, 2-methacrylic hydrazides, vinylformic acid, 2-methacrylic acid, 1-vinyl imidazole, 1-allyl imidazole, 4-vinylpridine, 2-vinyl pyridine, N-(4-ethenylphenyl) imines diacetic acid, allyl sulphonic acid or the 5-vinyl salicylic aldehyde, and m is selected from a kind of in 0,1,2 or 3.
Concrete preparation process is as follows:
The preparation of step 1 general formula (III) function monomer
Take by weighing general formula (II) and 5-chloromethyl salicylic aldehyde is dissolved in the solvent, make described general formula (II) solution and 5-chloromethyl salicylic aldehyde solution respectively, under the room temperature, 5-chloromethyl salicylic aldehyde solution is added in general formula (II) solution, stirring reaction is after 2～6 hours, be warming up to 60～85 ℃ and continued stirring reaction 2～6 hours, the reaction mass temperature is down to room temperature, filters recrystallization, drying makes the function monomer that contains quaternary ammonium salt unit and salicylic aldehyde unit of structure shown in the general formula (III);
Wherein said solvent is selected from acetone, butanone, chloroform, 1, the 2-ethylene dichloride, tetracol phenixin, 1, one or more in 4-dioxane, glycol dimethyl ether, ethylene glycol diethyl ether, toluene, dimethylbenzene, methyl-phenoxide, chlorobenzene, ethyl acetate, methyl acetate, butylacetate or the methylcyclohexane;
The consumption mass ratio of described general formula (II)/5-chloromethyl salicylic aldehyde/solvent is 1: 0.2～2.5: 2～20;
The preparation of step 2 general formula (VI) function monomer
Take by weighing the function monomer and the H that contain quaternary ammonium salt unit and salicylic aldehyde unit of structure shown in the general formula (III) respectively
2NZNH
2Be dissolved in the dehydrated alcohol, Glacial acetic acid is as catalyzer and souring agent, 60～90 ℃ of temperature controls, behind the stirring reaction 6～20 hours, be cooled to-5～15 ℃, filter, drying makes the function monomer that contains quaternary ammonium salt unit, salophen dentate or Salen dentate of structure shown in the general formula (VI);
Wherein said described Z chooses C
2～C
6A kind of in alkyl, phenyl ring, naphthalene nucleus or the pyridine ring;
General formula (III) and H
2NZNH
2The consumption mol ratio be 2.05～2.5: 1, the consumption of dehydrated alcohol is general formula (III) and H
2NZNH
22～5 times of quality summation, the consumption of Glacial acetic acid is H
2NZNH
20.1～10% of quality;
The preparation of step 3 general formula (I) function monomer
Taking by weighing the function monomer that contains quaternary ammonium salt unit, salophen dentate or Salen dentate of structure shown in the general formula (VI) that step 2 makes and alkali reagent and L respectively is dissolved in the solvent, stirring reaction is 1～2 hour under the room temperature, filter and remove the insoluble solid thing, it is standby that gained filtrate is called filtrate (1); Take by weighing MX
pBe dissolved in the solvent, filter and remove the insoluble solid thing, make filtrate and be called filtrate (2), described filtrate (2) is added in the described filtrate (1), 20～80 ℃ of temperature controls, stir reaction down after 2～10 hours, distillation is concentrated, reaction system is cooled to-5～15 ℃, separate out crystallization, filter, drying makes the function monomer that contains quaternary ammonium salt and salophen title complex or Salen complex structure unit of structure shown in the general formula (I); 3. reaction formula has explained the process of preparation general formula (I) function monomer:
Wherein said alkali reagent refers to a kind of in yellow soda ash, salt of wormwood, sodium hydroxide, potassium hydroxide, pyridine, 4-Dimethylamino pyridine, triethylamine, Tributylamine or the soda-lime, described soda-lime be by yellow soda ash or salt of wormwood and calcium oxide (being also referred to as unslaked lime) according to 1: 3 composite making of mass ratio, the consumption of described alkali reagent is 0.5～5 times of general formula (VI) function monomer quality;
Described solvent is selected from one or more in water, methyl alcohol, ethanol, propyl alcohol, butanols or the acetone, and described solvent load is 3～8 times of general formula (VI) function monomer quality;
Described L is selected from one or more in water, methyl alcohol, ethanol, acetone, acrylamide, 2-Methacrylamide, propylene hydrazides, 2-methacrylic hydrazides, vinylformic acid, 2-methacrylic acid, 1-vinyl imidazole, 1-allyl imidazole, 4-vinylpridine, 2-vinyl pyridine, N-(4-ethenylphenyl) imines diacetic acid, allyl sulphonic acid or the 5-vinyl salicylic aldehyde, and the consumption of described L is 1～3 times of general formula (VI) function monomer molar weight.
Described MX
pIn M be selected from a kind of in the transition metal ion, X is selected from F
-, Cl
-, Br
-, I
-, HSO
4 -, H
2PO
4 -Or CH
3COO
-In a kind of, p is selected from a kind of in 1,2 or 3; MX
pMole dosage be 0.8～1.2 times of general formula (VI) function monomer molar weight.
Specific embodiment
By following embodiment function monomer and the preparation method of structure shown in the general formula provided by the invention (I) are further specified, its purpose is to understand better content of the present invention.Therefore, function monomer of structure and preparation method thereof shown in the unlisted general formula (I) should not be considered as limiting the scope of the invention among the embodiment.Anyly all belong to the intellecture property aggressive behavior at improvement of the present invention.
The preparation of embodiment 1DMA-CS-Salen-Zn type function monomer
The preparation of step 1, DMA-CS
Taking by weighing methacrylic acid-2-(dimethylamino) ethyl ester (DMA) 78 grams and 5-chloromethyl salicylic aldehyde (5-CS) 80 grams is dissolved in respectively in the 100 gram ethyl acetate, make the ethyl acetate solution of described methacrylic acid-2-(dimethylamino) ethyl ester and the ethyl acetate solution of 5-chloromethyl salicylic aldehyde, under the room temperature, the ethyl acetate solution of 5-chloromethyl salicylic aldehyde is added in the ethyl acetate solution of methacrylic acid-2-(dimethylamino) ethyl ester, behind the stirring reaction 4 hours, heat up 60～65 ℃ and continued stirring reaction 6 hours.Reaction system leaves standstill and naturally cools to room temperature, filters and obtains shallow white crystalline material, recrystallization, drying, makes 151 gram DMA-CS, yield 95.6%, 137～138 ℃ of fusing points.
The preparation of step 2, DMA-CS-Salen
Take by weighing respectively 65 the gram DMA-CS and 15 the gram quadrols be dissolved in 100 milliliters of dehydrated alcohols, add 2 gram Glacial acetic acid again, 80～85 ℃ of temperature controls, stirring and refluxing was reacted 6 hours, and constantly steamed azeotrope 38 grams of part second alcohol and water, after finishing reaction, the reaction product system is cooled to 0～5 ℃, separates out the light yellow crystal powder, filter, drying makes DMA-CS-Salen.
The preparation of step 3, DMA-CS-Salen-Zn type function monomer
Take by weighing 65 gram DMA-CS-Salen and be dissolved in 200 milliliters of anhydrous methanols, stir down slowly adding 6 gram sodium hydroxide, react after 2 hours, filter and remove solid matter, gained filtrate for later use; Get zinc chloride 20 grams and be dissolved in 100 milliliters of anhydrous methanols, the filtering insoluble impurities adds gained zinc chloride methanol solution in the filtrate, 60～65 ℃ of temperature controls, stirring reaction 6 hours, distillation is cooled to 0 ℃ with reaction system after concentrating, separate out crystallization, filter, drying makes faint yellow 60.3 gram DMA-CS-Salen-Zn type function monomers, yield 87.3%, 161～165 ℃ of fusing points.
Ultimate analysis (theoretical value) C
34H
46Cl
2N
4O
6Zn:C53.47 (54.96), H6.19 (6.24), N7.54 (7.23), Cl9.39 (9.54).
IR (KBr, compressing tablet, cm
-1): 3541,3013,2929,2832,1712,1685,1614,1546,1323,1131,889.
H
1-NMR(DMSO-d
6，δ)：1.92(s，6H)，3.32(s，12H)，3.52(t，4H)，3.90(t，4H)，4.53(m，4H)，4.61(t，4H)，5.53(t，2H)，6.17(m，2H)，6.58～7.37(m，6H)，8.31(s，2H)。
The preparation of embodiment 2DMA-CS-Salophen-Cu type function monomer
According to method and the operation steps of embodiment 1, it is O-Phenylene Diamine that the quadrol in embodiment 1 step 2 is changed, and the zinc chloride in the step 3 changes and is cupric chloride, makes yellowish green DMA-CS-Salophen-Cu type function monomer.
The preparation of embodiment 3DMAA-CS-Salen-Mn function monomer
Method and operation steps according to embodiment 1, methacrylic acid-2-(dimethylamino) ethyl ester (DMA) of embodiment 1 step 1 is changed methacryloyl (2-dimethylamino ethamine) (DMAA), quadrol in embodiment 1 step 2 changes and is O-Phenylene Diamine, the zinc chloride of step 3 changes to 4-vinylpridine and manganese acetate, makes bolarious DMAA-CS-Salen-Mn function monomer.
Function monomer characteristic among embodiment 4 embodiment 1～3
Table 1 has been listed embodiment 1DMA-CS-Salen-Zn type function monomer, embodiment 2DMA-CS-Salophen-Cu type function monomer and embodiment 3DMAA-CS-Salen-Mn type function monomer at water, ethanol, chloroform, ethyl acetate, N, the solvability in the dinethylformamide solvent:
Function monomer characteristic among table 1. embodiment 1～4
Claims (2)
1. function monomer, the chemical structure shown in (I) that it is characterized in that having general formula:
R in its formula of (I) chooses H or methyl, R
1And R
2Choose C respectively
1～C
18A kind of in the alkyl, Y chooses O or NH, and n chooses a kind of in 2,3,4,5 or 6, and Z chooses C
2～C
6A kind of in alkyl, phenyl ring, naphthalene nucleus or the pyridine ring, M is selected from transition metal ion, L is selected from one or more in water, methyl alcohol, ethanol, acetone, acrylamide, 2-Methacrylamide, propylene hydrazides, 2-methacrylic hydrazides, vinylformic acid, 2-methacrylic acid, 1-vinyl imidazole, 1-allyl imidazole, 4-vinylpridine, 2-vinyl pyridine, N-(4-ethenylphenyl) imines diacetic acid, allyl sulphonic acid or the 5-vinyl salicylic aldehyde, m is selected from a kind of in 0,1,2 or 3, X
-Be selected from F
-, Cl
-, Br
-, I
-, HSO
4 -, H
2PO
4 -Or CH
3COO
-In a kind of.
2. according to the preparation method of the described function monomer of claim 1, it is characterized in that being realizing according to following preparation process:
The preparation of step 1 general formula (III) function monomer
Take by weighing general formula (II) and 5-chloromethyl salicylic aldehyde is dissolved in the solvent, make described general formula (II) solution and 5-chloromethyl salicylic aldehyde solution respectively, under the room temperature, 5-chloromethyl salicylic aldehyde solution is added in general formula (II) solution, stirring reaction is after 2～6 hours, be warming up to 60～85 ℃ and continued stirring reaction 2～6 hours, the reaction mass temperature is down to room temperature, filters recrystallization, drying makes the function monomer that contains quaternary ammonium salt unit and salicylic aldehyde unit of structure shown in the general formula (III); 1. reaction formula has explained the preparation process of general formula (III) function monomer:
Wherein the R of reaction formula in 1. chooses H or methyl, R
1And R
2Choose C respectively
1～C
18A kind of in the alkyl, Y chooses O or NH, and n chooses a kind of in 2,3,4,5 or 6;
Described solvent is selected from acetone, butanone, chloroform, 1, the 2-ethylene dichloride, tetracol phenixin, 1, one or more in 4-dioxane, glycol dimethyl ether, ethylene glycol diethyl ether, toluene, dimethylbenzene, methyl-phenoxide, chlorobenzene, ethyl acetate, methyl acetate, butylacetate or the methylcyclohexane;
The consumption mass ratio of described general formula (II)/5-chloromethyl salicylic aldehyde/solvent is 1: 0.2～2.5: 2～20;
The preparation of step 2 general formula (VI) function monomer
Take by weighing the function monomer and the H that contain quaternary ammonium salt unit and salicylic aldehyde unit of structure shown in the general formula (III) respectively
2NZNH
2Be dissolved in the dehydrated alcohol, Glacial acetic acid is as catalyzer and souring agent, 60～90 ℃ of temperature controls, behind the stirring reaction 6～20 hours, be cooled to-5～15 ℃, filter, drying makes the function monomer that contains quaternary ammonium salt unit, salophen dentate or Salen dentate of structure shown in the general formula (VI); 2. reaction formula has explained the process of preparation general formula (VI) function monomer:
Wherein the R of reaction formula in 2. chooses H or methyl, R
1And R
2Choose C respectively
1～C
18A kind of in the alkyl, Y chooses O or NH, and n chooses a kind of in 2,3,4,5 or 6, and Z chooses C
2～C
6A kind of in alkyl, phenyl ring, naphthalene nucleus or the pyridine ring;
Described general formula (III) and H
2NZNH
2The consumption mol ratio be 2.05～2.5: 1, the consumption of dehydrated alcohol is general formula (III) and H
2NZNH
22～5 times of quality summation, the consumption of Glacial acetic acid is H
2NZNH
20.1～10% of quality;
The preparation of step 3 general formula (I) function monomer
Taking by weighing the function monomer that contains quaternary ammonium salt unit, salophen dentate or Salen dentate of structure shown in the general formula (VI) that step 2 makes and alkali reagent and L respectively is dissolved in the solvent, stirring reaction is 1～2 hour under the room temperature, filter and remove the insoluble solid thing, it is standby that gained filtrate is called filtrate (1); Take by weighing MX
pBe dissolved in the solvent, filter and remove the insoluble solid thing, make filtrate and be called filtrate (2), described filtrate (2) is added in the described filtrate (1), 20～80 ℃ of temperature controls, stir reaction down after 2～10 hours, distillation is concentrated, reaction system is cooled to-5～15 ℃, separate out crystallization, filter, drying makes the function monomer that contains quaternary ammonium salt and salophen title complex or Salen complex structure unit of structure shown in the general formula (I); 3. reaction formula has explained the process of preparation general formula (I) function monomer:
Wherein R chooses H or methyl, R
1And R
2Choose C respectively
1～C
18A kind of in the alkyl, n choose a kind of in 2,3,4,5 or 6, and Y chooses O or NH, and Z chooses C
2～C
6A kind of in alkyl, phenyl ring, naphthalene nucleus or the pyridine ring;
Described MX
pIn M refer to transition metal ion, MX
pIn X refer to F
-, Cl
-, Br
-, I
-, HSO
4 -, H
2PO
4 -Or CH
3COO
-In a kind of, MX
pIn p refer to a kind of in 1,2,3 or 4; MX
pMole dosage be 0.8～1.2 times of general formula (VI) function monomer mole dosage;
Described L is selected from one or more in water, methyl alcohol, ethanol, acetone, acrylamide, 2-Methacrylamide, propylene hydrazides, 2-methacrylic hydrazides, vinylformic acid, 2-methacrylic acid, 1-vinyl imidazole, 1-allyl imidazole, 4-vinylpridine, 2-vinyl pyridine, N-(4-ethenylphenyl) imines diacetic acid, allyl sulphonic acid or the 5-vinyl salicylic aldehyde, m is selected from a kind of in 0,1,2 or 3, and the consumption of described L is 1～2 times of general formula (VI) function monomer molar weight;
Described alkali reagent refers to a kind of in yellow soda ash, salt of wormwood, sodium hydroxide, potassium hydroxide, pyridine, 4-Dimethylamino pyridine, triethylamine, Tributylamine or the soda-lime, described soda-lime be by yellow soda ash or salt of wormwood and calcium oxide (being also referred to as unslaked lime) according to 1: 3 composite making of mass ratio, the consumption of described alkali reagent is 0.5～5 times of general formula (VI) function monomer quality;
Described solvent is selected from one or more in water, methyl alcohol, ethanol, propyl alcohol, butanols or the acetone, and described solvent load is 3～8 times of general formula (VI) function monomer quality.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013101411073A CN103193824A (en) | 2013-04-08 | 2013-04-08 | Functional monomer and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013101411073A CN103193824A (en) | 2013-04-08 | 2013-04-08 | Functional monomer and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103193824A true CN103193824A (en) | 2013-07-10 |
Family
ID=48716657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2013101411073A Pending CN103193824A (en) | 2013-04-08 | 2013-04-08 | Functional monomer and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103193824A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965076A (en) * | 2014-05-05 | 2014-08-06 | 淮海工学院 | Functional monomer containing quarternary ammonium ions and salicylaldehyde Schiff base |
| CN105503649A (en) * | 2016-01-08 | 2016-04-20 | 淮海工学院 | Polyols containing quaternary ammonium cations and Salen or Salophen functional groups and preparation method thereof |
| CN106008275A (en) * | 2016-06-24 | 2016-10-12 | 中国科学院新疆理化技术研究所 | Synthesis method of multi-ureido tripodal type functional monomer molecule with nitrogen as center |
| CN106750316A (en) * | 2017-01-16 | 2017-05-31 | 南华大学 | A kind of preparation method of magnetic core-shell nanoparticle surface uranyl molecularly imprinted polymer |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102504094A (en) * | 2011-09-07 | 2012-06-20 | 淮海工学院 | Acrylonitrile copolymer porous resin ball containing quaternary ammonium group and salicylaldehyde and preparation method thereof |
| CN102766150A (en) * | 2012-07-10 | 2012-11-07 | 淮海工学院 | Polymerizable salicylic aldehyde complex containing quaternary ammonium salt and preparation method thereof |
| CN102924656A (en) * | 2012-10-10 | 2013-02-13 | 淮海工学院 | Transition metal ion imprinted polymer and preparation method thereof |
-
2013
- 2013-04-08 CN CN2013101411073A patent/CN103193824A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102504094A (en) * | 2011-09-07 | 2012-06-20 | 淮海工学院 | Acrylonitrile copolymer porous resin ball containing quaternary ammonium group and salicylaldehyde and preparation method thereof |
| CN102766150A (en) * | 2012-07-10 | 2012-11-07 | 淮海工学院 | Polymerizable salicylic aldehyde complex containing quaternary ammonium salt and preparation method thereof |
| CN102924656A (en) * | 2012-10-10 | 2013-02-13 | 淮海工学院 | Transition metal ion imprinted polymer and preparation method thereof |
Non-Patent Citations (4)
| Title |
|---|
| D. DISALVO等,: "Catalytic epoxidations of styrene using a manganese functionalized polymer", 《REACTIVE & FUNCTIONAL POLYMERS》, 31 December 2002 (2002-12-31), pages 103 - 112, XP004395999, DOI: 10.1016/S1381-5148(02)00166-9 * |
| MARTA GAWIN等,: "Preparation of a new Cd(II)-imprinted polymer and its application to determination of cadmium(II) via flow-injection-flame atomic absorption spectrometry", 《TALANTA》, 19 September 2009 (2009-09-19), pages 1305 - 1310 * |
| STANISLAW WALAS等,: "Application of a metal ion-imprinted polymer based on salen–Cu complex to flow injection preconcentration and FAAS determination of copper", 《TALANTA》, 10 March 2008 (2008-03-10), pages 96 - 101 * |
| 何芳芳: "《南华大学硕士论文》", 15 January 2013, article "磁性Salophen Th(Ⅳ)识别材料的制备及性能" * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965076A (en) * | 2014-05-05 | 2014-08-06 | 淮海工学院 | Functional monomer containing quarternary ammonium ions and salicylaldehyde Schiff base |
| CN105503649A (en) * | 2016-01-08 | 2016-04-20 | 淮海工学院 | Polyols containing quaternary ammonium cations and Salen or Salophen functional groups and preparation method thereof |
| CN106008275A (en) * | 2016-06-24 | 2016-10-12 | 中国科学院新疆理化技术研究所 | Synthesis method of multi-ureido tripodal type functional monomer molecule with nitrogen as center |
| CN106750316A (en) * | 2017-01-16 | 2017-05-31 | 南华大学 | A kind of preparation method of magnetic core-shell nanoparticle surface uranyl molecularly imprinted polymer |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103214500A (en) | Functional monomer for preparing heavy metal ion imprinted polymer and preparation method | |
| CN103193807A (en) | Water-soluble functional monomer containing quaternary ammonium salt and Schiff base compound and preparation method | |
| CN103193824A (en) | Functional monomer and preparation method thereof | |
| CN104231141B (en) | A kind of amino nitrogen heterocyclic ring resin and preparation method thereof | |
| CN104370820A (en) | Preparation method and applications of porous metal organic skeleton material | |
| CN106008207B (en) | A kind of method that compound phosphotungstate catalyzes and synthesizes citrate | |
| CN106866497B (en) | A kind of norborneol vinyl compound and its preparation method and application | |
| CN103193928B (en) | Coordination imprinted polymer and preparation method thereof | |
| CN101967209A (en) | N-acetylethylenediamine chelate resin and preparation method thereof | |
| CN110042234A (en) | A kind of extractant and the preparation method and application thereof | |
| CN107629217B (en) | Cu-Nd dissimilar metal coordination polymer and preparation method thereof | |
| CN104447591B (en) | Energy-containing compound 3,3 '-diaminourea-2,2 '-bis-(2,2,2-Trinitroethyls)-5,5 '-Lian triazole-diamines and its preparation method and intermediate | |
| CN104387336B (en) | Isosorbide-5-Nitrae, the preparation method of 7,10-tetraazacyclododecanand and nanofiltration membrane thereof | |
| CN103122044A (en) | Sulphonic acid type macroporous ion exchange resin and preparation method thereof | |
| CN110105379A (en) | A kind of Zn-MOFs complex preparation method with fluorescence identifying | |
| CN101138741A (en) | Ionic liquid loaded ruthenium catalyst containing pyridine ligand and producing method thereof | |
| CN104861000A (en) | Ferrocene tetrazole high nitrogen energy containing ionic compound and preparation method thereof | |
| TWI658045B (en) | Multi-branched cationic phosphonium salt, forward osmosis extract employing the same and forward osmosis seawater desalination process | |
| CN105130851A (en) | Unsaturated sulfobetaine monomer, and preparation method and application thereof | |
| CN104356052A (en) | Cross-linkable copper (II) monomer containing quaternary ammonium cation and salicylic Schiff base and preparation method of cross-linkable copper (II) | |
| CN106916174B (en) | A kind of chiral amino acid derivative complex, preparation method and applications | |
| CN113004456A (en) | Styrene-based monomer-based hydrophilic heavy metal ion chelating copolymer resin and synthetic method thereof | |
| TWI738291B (en) | Extracted material for forward osmosis, preparation method thereof, and forward-osmosis water desalination system using the same | |
| CN104402745A (en) | Method for synthesizing isopropyl 3-aminocrotonate | |
| JP2010163561A (en) | Substituted polyacetylene, production method thereof, self-supporting substituted polyacetylene film, production method thereof, carbon dioxide separation membrane, and film which reversibly changes color thereof upon elongation or contraction |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20130710 |