CN115340653A - Preparation method of hydrophilic organic polymer - Google Patents
Preparation method of hydrophilic organic polymer Download PDFInfo
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- CN115340653A CN115340653A CN202210975428.2A CN202210975428A CN115340653A CN 115340653 A CN115340653 A CN 115340653A CN 202210975428 A CN202210975428 A CN 202210975428A CN 115340653 A CN115340653 A CN 115340653A
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- Prior art keywords
- organic polymer
- aromatic
- hydrophilic organic
- hydrophilic
- aromatic amide
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- 229920000620 organic polymer Polymers 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 10
- -1 aromatic amide compound Chemical class 0.000 claims abstract description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000003934 aromatic aldehydes Chemical class 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003172 aldehyde group Chemical group 0.000 claims description 5
- 150000001299 aldehydes Chemical class 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- 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
- 238000005406 washing Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000009210 therapy by ultrasound 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
- 150000001408 amides Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 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
- 238000007344 nucleophilic reaction Methods 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 150000001491 aromatic compounds Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000013310 covalent-organic framework Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 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
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
The invention belongs to the technical field of polymer preparation, and provides a method for preparing a hydrophilic compound from aromatic amide and aromatic aldehyde with low electron cloud density of nitrogen atoms, wherein the method comprises the steps of dissolving a functional monomer containing multiple aromatic aldehyde groups and the 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 invention can prepare the hydrophilic organic polymer simply and quickly.
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
The Schiff base reaction is an important way 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-polymerization microporous polymers and the like. The aromatic amide compound is an aromatic compound substituted by formyl, and has the conjugated aromatic ring and amide and the structural characteristics of the amide, so that the electron cloud density on a nitrogen atom is low, and the aromatic amide compound is more difficult to perform nucleophilic reaction with aromatic aldehyde groups than aliphatic amino and aromatic amino. Aliphatic amino and aromatic amino with more electron cloud density on nitrogen atoms often form hydrophobic materials with aromatic aldehyde groups, and a new method for preparing hydrophilic compounds from aromatic amide and aromatic aldehyde groups with low electron cloud density on nitrogen atoms is hoped to be developed.
At present, the preparation of organic polymers based on the polymerization of aromatic amide compounds with aromatic aldehyde compounds has not been reported.
Disclosure of Invention
Aiming at the problem that the aromatic aldehyde group of the aromatic amide compound is difficult to generate nucleophilic reaction, the invention provides a preparation method of a hydrophilic organic polymer, which takes an acetic acid solution as a catalyst, mixes a functional monomer containing polyaromatic aldehyde group, an aromatic amide compound and a reaction solvent, ultrasonically dissolves the mixture, and then generates 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 preparation method of a hydrophilic organic polymer comprises the steps of dissolving a functional monomer containing polyaromatic aldehyde groups and an aromatic amide compound in an organic solvent, then adding an acetic acid solution as a catalyst, fully mixing, heating to 50-120 ℃, and reacting for 4-24h to generate the hydrophilic organic polymer.
The first improvement is that: the functional monomer containing the polyaromatic aldehyde group is trimesic aldehyde and/or triacyl trimesic phenol, and the aromatic amide compound is terephthalamide and/or trimesamide.
The first improvement is that: the organic solvent is N, N-dimethylformamide, 1, 4-dioxane or dimethyl sulfoxide.
The first improvement is that: the mass ratio of the functional monomer containing aromatic aldehyde groups to the aromatic amide compound is as follows: (3-7): (2-4).
Has the beneficial effects 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-loading system evaluation of polar drug molecules.
Drawings
FIG. 1 is a scanning electron micrograph of a hydrophilic organic polymer prepared in example 1.
FIG. 2 is a scanning electron micrograph of a hydrophilic organic polymer prepared in example 2.
FIG. 3 is a contact angle of a 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
Adding 48mg of trimesic aldehyde, 32mg of terephthalamide and 3mL of N, N-dimethylformamide into a round-bottom flask, and carrying out ultrasonic treatment for 15min to uniformly mix the components; the above round bottom flask was charged. Placing the mixture in a water bath kettle at 60 ℃ for reaction for 6 hours; washing the product with methanol, and washing out the reaction solvent and some unreacted substances to obtain the hydrophilic organic polymer.
As shown in FIG. 1, the prepared hydrophilic organic polymer is characterized by irregular piled polymer.
Example 2
Adding 48mg of trimesic aldehyde, 32mg of terephthalamide and 3mL of N, N-dimethylformamide into a round-bottom flask, and carrying out ultrasonic treatment for 15min to uniformly mix the components; putting the round-bottom flask into a 120 ℃ gas phase furnace for reaction for 3 days; washing the product with methanol, and washing out the reaction solvent and some unreacted substances to obtain the hydrophilic organic polymer.
As shown in FIG. 2, the prepared hydrophilic organic polymer is characterized by a cuboid material with uneven size.
Example 3
Adding 60mg of triacyl trimesic phenol, 60mg of trimesoyl triamide and 3mL of dimethyl sulfoxide into a round-bottom flask, and carrying out ultrasonic treatment for 15min to uniformly mix the components; putting the round-bottom flask into a 120 ℃ gas phase furnace for reaction for 3 days; washing the product with methanol, and washing 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 using an optical method based on a liquid surface shape analysis, and as shown in fig. 3, the contact angle was about 64 °, which proved to be a hydrophilic material.
Due to the hydrophilic property, the prepared material is expected to be used for glycopeptide enrichment, sample pretreatment of environmental pollutants or drug-loading system evaluation of polar drug molecules.
The above-mentioned embodiments are merely illustrative of the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various modifications and improvements of the technical solution of the present invention by those skilled in the art should fall within the protection scope defined by the claims of the present invention without departing from the spirit of the present invention.
Claims (4)
1. A method for preparing a hydrophilic organic polymer, characterized by: dissolving functional monomers containing polyaromatic aldehyde groups and aromatic amide compounds in an organic solvent, then adding an acetic acid solution as a catalyst, fully mixing, heating to 50-120 ℃, and reacting for 4-24h to generate the hydrophilic organic polymer.
2. The method of claim 1, wherein: the functional monomer containing the polyaromatic aldehyde group is trimesic aldehyde and/or triacyl trimesic phenol, and the aromatic amide compound is terephthalamide and/or trimesamide.
3. The method of claim 1, wherein: the organic solvent is N, N-dimethylformamide, 1, 4-dioxane or dimethyl sulfoxide.
4. The production method according to claim 1, characterized in that: the mass ratio of the functional monomer containing aromatic aldehyde group to the aromatic amide compound is as follows: (3-7): (2-4).
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| CN202210975428.2A CN115340653B (en) | 2022-08-15 | 2022-08-15 | Preparation method of hydrophilic organic polymer |
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|---|---|---|---|
| CN202210975428.2A CN115340653B (en) | 2022-08-15 | 2022-08-15 | Preparation method of hydrophilic organic polymer |
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| Publication Number | Publication Date |
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| CN115340653A true CN115340653A (en) | 2022-11-15 |
| CN115340653B CN115340653B (en) | 2023-10-20 |
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Citations (6)
| 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 |
| US20140192501A1 (en) * | 2012-11-28 | 2014-07-10 | Hitachi Chemical Company, Ltd. | Modified siloxane compound having aromatic azomethine, thermosetting resin composition including thereof, prepreg, film having resin, laminate, multi-layer printed wiring board, and semiconductor package |
| CN113845665A (en) * | 2021-09-28 | 2021-12-28 | 天津大学 | Full-conjugated organic triazine framework material and preparation method and application thereof |
-
2022
- 2022-08-15 CN CN202210975428.2A patent/CN115340653B/en active Active
Patent Citations (6)
| 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 |
| US20140192501A1 (en) * | 2012-11-28 | 2014-07-10 | Hitachi Chemical Company, Ltd. | Modified siloxane compound having aromatic azomethine, thermosetting resin composition including thereof, prepreg, film having resin, laminate, multi-layer printed wiring board, and semiconductor package |
| 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 (4)
| Title |
|---|
| BASKO, M, 等: "Synthesis of double hydrophilic graft copolymers with a polyacetal backbone", MACROMOLECULES, vol. 35, no. 24, pages 8948 - 8953 * |
| DUBE, D，等: "Reductive N-alkylation of amides, carbamates and ureas", TETRAHEDRON LETTERS, vol. 40, no. 12, pages 2295 - 2298, XP004157456, DOI: 10.1016/S0040-4039(99)00211-7 * |
| 田磊: "TEX的合成工艺及性能研究", 中国优秀硕士学位论文全文数据库 (工程科技Ⅰ辑), no. 02, pages 017 - 117 * |
| 郭晨晨: "氮杂金属配合物的合成、表征及催化应用", 中国优秀硕士学位论文全文数据库工程科技Ⅰ辑, no. 01, pages 014 - 1122 * |
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| CN115340653B (en) | 2023-10-20 |
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