CN115340653B - Preparation method of hydrophilic organic polymer - Google Patents
Preparation method of hydrophilic organic polymer Download PDFInfo
- Publication number
- CN115340653B CN115340653B CN202210975428.2A CN202210975428A CN115340653B CN 115340653 B CN115340653 B CN 115340653B CN 202210975428 A CN202210975428 A CN 202210975428A CN 115340653 B CN115340653 B CN 115340653B
- Authority
- CN
- China
- Prior art keywords
- aromatic
- organic polymer
- hydrophilic organic
- trimesic
- preparation
- 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.)
- Active
Links
- 229920000620 organic polymer Polymers 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title description 8
- -1 aromatic amide compounds Chemical class 0.000 claims abstract description 16
- 150000003934 aromatic aldehydes Chemical group 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 claims description 4
- QHVJZYJNUUACLR-UHFFFAOYSA-N 5-carbamoylbenzene-1,3-dicarboxylic acid Chemical compound NC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QHVJZYJNUUACLR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- 238000007344 nucleophilic reaction Methods 0.000 abstract description 3
- 150000008430 aromatic amides Chemical class 0.000 abstract description 2
- 150000002433 hydrophilic molecules Chemical class 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000009210 therapy by ultrasound Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 2
- 102000002068 Glycopeptides Human genes 0.000 description 2
- 108010015899 Glycopeptides Proteins 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003344 environmental pollutant Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000001000 micrograph Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000013310 covalent-organic framework Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/0212—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds
- C08G16/0218—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen
- C08G16/0231—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen containing nitrogen
Abstract
Aiming at the technical problem that nucleophilic reaction of aromatic aldehyde groups of aromatic amide compounds is difficult to occur, the invention provides a method for preparing hydrophilic compounds from aromatic amide and aromatic aldehyde groups with low electron cloud density of nitrogen atoms. The invention can simply and rapidly prepare the hydrophilic organic polymer.
Description
Technical Field
The invention belongs to the technical field of polymer preparation, and particularly relates to a preparation method of a hydrophilic organic polymer.
Background
Schiff base reaction is an important mode for preparing organic polymers from aldehyde compounds and amine compounds. Schiff base condensation reaction of aromatic aldehyde compounds and aromatic amine compounds has been applied to the preparation of covalent organic frameworks, organic porous polymers, self-polymerizing microporous polymers and the like. Aromatic amide compounds are formyl-substituted aromatic compounds, and due to the conjugation of the aromatic ring and the amide, and the structural characteristics of the amide itself, the electron cloud density on the nitrogen atom is very low, and nucleophilic reaction with aromatic aldehyde groups is more difficult than with aliphatic amino groups and aromatic amino groups. The aliphatic amino group and the aromatic amino group with more electron cloud density on the nitrogen atom often form a hydrophobic material with the aromatic aldehyde group, and a new method for preparing a hydrophilic compound by using the aromatic amide with low electron cloud density on the nitrogen atom and the aromatic aldehyde group is hoped to be developed.
At present, the preparation of organic polymers based on the polymerization of aromatic amide compounds and aromatic aldehyde compounds has not been reported.
Disclosure of Invention
Aiming at the problem that aromatic aldehyde groups of aromatic amide compounds are difficult to generate nucleophilic reaction, the invention provides a preparation method of a hydrophilic organic polymer, which comprises the steps of mixing functional monomers containing multiple aromatic aldehyde groups, aromatic amide compounds and a reaction solvent with acetic acid solution as a catalyst, ultrasonically dissolving, and then performing polymerization reaction under the heating condition to prepare the hydrophilic organic polymer in one step.
The technical scheme of the invention is as follows:
a process for preparing hydrophilic organic polymer includes such steps as dissolving the functional monomer containing multi-aromatic aldehyde groups and aromatic amide compound in organic solvent, adding acetic acid solution as catalyst, mixing, heating to 50-120 deg.C, and reacting for 4-24 hr.
Progress one: the functional monomer containing the polyaromatic aldehyde group is trimesic aldehyde and/or tricarboxyl trimesic phenol, and the aromatic amide compound is terephthalamide and/or trimesic amide.
Progress one: the organic solvent is N, N-dimethylformamide, 1, 4-dioxane or dimethyl sulfoxide.
Progress one: the mass ratio of the functional monomer containing aromatic aldehyde groups to the aromatic amide compound is as follows: (3-7): (2-4).
The beneficial effects are that: the preparation method is simple and convenient to operate and high in reaction speed. The prepared organic polymer has hydrophilicity and is expected to be used for glycopeptide enrichment, sample pretreatment of environmental pollutants or drug carrying system evaluation of polar drug molecules.
Drawings
FIG. 1 is a scanning electron microscope image of the hydrophilic organic polymer prepared in example 1.
FIG. 2 is a scanning electron microscope image of the hydrophilic organic polymer prepared in example 2.
FIG. 3 shows the contact angle of the hydrophilic organic polymer prepared in example 1.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
Example 1
48mg of trimellitic aldehyde, 32mg of terephthalamide and 3mL of N, N-dimethylformamide are added into a round-bottom flask, and the ultrasonic treatment is carried out for 15min to ensure that all components in the mixture are uniformly mixed; the round bottom flask described above was used. Placing the mixture in a water bath kettle at 60 ℃ for reaction for 6 hours; and (3) washing the product by using methanol, and flushing out the reaction solvent and some unreacted substances to obtain the hydrophilic organic polymer.
As shown in FIG. 1, the morphology of the prepared hydrophilic organic polymer is characterized by irregular piled polymers.
Example 2
48mg of trimellitic aldehyde, 32mg of terephthalamide and 3mL of N, N-dimethylformamide are added into a round-bottom flask, and the ultrasonic treatment is carried out for 15min to ensure that all components in the mixture are uniformly mixed; placing the round bottom flask in a gas phase furnace at 120 ℃ for reaction for 3 days; and (3) washing the product by using methanol, and flushing out the reaction solvent and some unreacted substances to obtain the hydrophilic organic polymer.
As shown in FIG. 2, the prepared hydrophilic organic polymer has the appearance characteristic of cuboid materials with uneven sizes.
Example 3
60mg of tricarboxyl phloroglucinol, 60mg of trimesic acid amide and 3mL of dimethyl sulfoxide are added into a round bottom flask, and the ultrasonic treatment is carried out for 15min to ensure that all components in the mixture are uniformly mixed; placing the round bottom flask in a gas phase furnace at 120 ℃ for reaction for 3 days; and (3) washing the product by using methanol, and flushing out the reaction solvent and some unreacted substances to obtain the hydrophilic organic polymer.
Performance and use
The contact angle of the hydrophilic organic polymer prepared in example 1 was directly measured by an optical method based on a liquid level shape analysis, and as shown in fig. 3, the contact angle was about 64 °, which proves to be a hydrophilic material.
Because of the hydrophilic property, the prepared material is expected to be used for glycopeptide enrichment, sample pretreatment of environmental pollutants or drug carrying system evaluation of polar drug molecules.
The above examples are only illustrative of the preferred embodiments of the present invention and are not intended to limit the scope of the present invention, and various modifications and improvements made by those skilled in the art to the technical solution of the present invention should fall within the scope of protection defined by the claims of the present invention without departing from the spirit of the present invention.
Claims (3)
1. A method for preparing a hydrophilic organic polymer, characterized by: dissolving a functional monomer containing multiple aromatic aldehyde groups and an aromatic amide compound in an organic solvent, adding an acetic acid solution as a catalyst, fully mixing, heating to 50-120 ℃, and reacting for 4-24 hours to generate the hydrophilic organic polymer;
the functional monomer containing the polyaromatic aldehyde group is trimesic aldehyde and/or tricarboxyl trimesic phenol, and the aromatic amide compound is terephthalamide and/or trimesic amide.
2. The method of manufacturing according to claim 1, characterized in that: the organic solvent is N, N-dimethylformamide, 1, 4-dioxane or dimethyl sulfoxide.
3. The method of manufacturing according to claim 1, characterized in that: the mass ratio of the functional monomer containing aromatic aldehyde groups to the aromatic amide compound is as follows: (3-7): (2-4).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210975428.2A CN115340653B (en) | 2022-08-15 | 2022-08-15 | Preparation method of hydrophilic organic polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210975428.2A CN115340653B (en) | 2022-08-15 | 2022-08-15 | Preparation method of hydrophilic organic polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115340653A CN115340653A (en) | 2022-11-15 |
| CN115340653B true CN115340653B (en) | 2023-10-20 |
Family
ID=83951768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210975428.2A Active CN115340653B (en) | 2022-08-15 | 2022-08-15 | Preparation method of hydrophilic organic polymer |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115340653B (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR900009759A (en) * | 1988-12-01 | 1990-07-05 | 한국과학기술원 | Novel aromatic polyamide containing monomeric units of N, N'-bis-4,3'-diaminodiphenyl ether |
| WO2005085180A1 (en) * | 2004-03-10 | 2005-09-15 | Japan Science And Technology Agency | Method of amidocarbonylation reaction |
| WO2009153275A1 (en) * | 2008-06-18 | 2009-12-23 | Basf Se | Glyoxal and methylglyoxal as additives for polymer blends |
| CN102985465A (en) * | 2010-04-16 | 2013-03-20 | 株式会社大赛璐 | Crosslinked composition |
| CN113845665A (en) * | 2021-09-28 | 2021-12-28 | 天津大学 | Full-conjugated organic triazine framework material and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10323126B2 (en) * | 2012-11-28 | 2019-06-18 | Hitachi Chemical Company, Ltd. | Siloxane compound, modified imide resin, thermosetting resin composition, prepreg, film with resin, laminated plate, multilayer printed wiring board, and semiconductor package |
-
2022
- 2022-08-15 CN CN202210975428.2A patent/CN115340653B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR900009759A (en) * | 1988-12-01 | 1990-07-05 | 한국과학기술원 | Novel aromatic polyamide containing monomeric units of N, N'-bis-4,3'-diaminodiphenyl ether |
| WO2005085180A1 (en) * | 2004-03-10 | 2005-09-15 | Japan Science And Technology Agency | Method of amidocarbonylation reaction |
| WO2009153275A1 (en) * | 2008-06-18 | 2009-12-23 | Basf Se | Glyoxal and methylglyoxal as additives for polymer blends |
| CN102985465A (en) * | 2010-04-16 | 2013-03-20 | 株式会社大赛璐 | Crosslinked composition |
| CN113845665A (en) * | 2021-09-28 | 2021-12-28 | 天津大学 | Full-conjugated organic triazine framework material and preparation method and application thereof |
Non-Patent Citations (5)
| Title |
|---|
| Reductive N-alkylation of amides, carbamates and ureas;Dube, D，等;TETRAHEDRON LETTERS;第40卷(第12期);2295-2298 * |
| Smith,M.B.,March,J..March高等有机化学——反应、机理与结构.化学工业出版社,2009,569. * |
| Synthesis of double hydrophilic graft copolymers with a polyacetal backbone;Basko, M, 等;MACROMOLECULES;第35卷(第24期);8948-8953 * |
| TEX的合成工艺及性能研究;田磊;中国优秀硕士学位论文全文数据库 (工程科技Ⅰ辑)(第02期);B017-117 * |
| 氮杂金属配合物的合成、表征及催化应用;郭晨晨;中国优秀硕士学位论文全文数据库工程科技Ⅰ辑(第01期);B014-1122 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115340653A (en) | 2022-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Danks et al. | Alkaline anion-exchange radiation-grafted membranes for possible electrochemical application in fuel cells | |
| Fenton et al. | β‐Aminoacrylate Synthetic Hydrogels: Easily Accessible and Operationally Simple Biomaterials Networks | |
| Yin et al. | Tuning the microstructure of crosslinked Poly (ionic liquid) membranes and gels via a multicomponent reaction for improved CO2 capture performance | |
| CN103059300B (en) | Polypyrron with sulfated side chain and preparation method of polypyrron | |
| US6399714B1 (en) | Crosslinked polyamide | |
| US20080221325A1 (en) | Exchange membrane containing modified maleimide oligomers | |
| US9840701B2 (en) | Porous membrane having immobilized enzyme, porous membrane composite including the same, and preparation method thereof | |
| CN106279672A (en) | From tool micro-porous copolymers, its preparation method and application | |
| CN115340653B (en) | Preparation method of hydrophilic organic polymer | |
| JP7405666B2 (en) | Polyethyleneimine and method for producing polyethyleneimine | |
| JP2020532617A (en) | Crosslinkable polyfluorine (arylene ether) | |
| CN112142935B (en) | Benzoxazine resin containing quaternary ammonium group and preparation method and application thereof | |
| CN110975649A (en) | Modified polyvinylidene fluoride ultrafiltration membrane and preparation method thereof | |
| CN103073702B (en) | Polyimide with sulfonated side chain and preparation method thereof | |
| CN112194767A (en) | Benzoxazine resin containing zwitter-ion group and preparation method and application thereof | |
| KR101899192B1 (en) | A Method for Synthesizing a Polydopamine Using Plasma Polymerization | |
| CN115991973A (en) | Catechol modified polyethyleneimine water-based adhesive and synthetic method thereof | |
| CN106496545A (en) | PAEK containing indolyl radical and preparation method thereof | |
| Nishikubo et al. | Synthesis of polymers bearing pendant norbornadiene moieties by addition reaction of poly (glycidyl methacrylate‐co‐methyl methacrylate) s with 2, 5‐norbornadiene‐2‐carboxylic acids | |
| CN114560964B (en) | Synthesis method and application of carboxyl functionalized polyionic liquid | |
| Chen et al. | Preparation of Auto-Photosensitive Hyperbranched Co-polyimide by the Condensation of 4, 4'-(Hexafluoroisopropy1idene) diphthalic Anhydride and 3, 3', 4, 4'-Benzophenonetetracarboxylic Dianhydride with 1, 3, 5-Tris (4-aminophenoxy) benzene through a Stage Addition Reaction Method | |
| CN108409927B (en) | Imidazole functionalized polymer and preparation method thereof | |
| JP2005272666A (en) | Polyimide resin and method for producing the same | |
| Yang et al. | Enzymatic synthesis of chiral polyamide via condensation of natural source amino acid diesters and diamine | |
| KR20170012974A (en) | Novel method for preparation of polybenzimidazole under mild condition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |