CN115340653B - 一种亲水有机聚合物的制备方法 - Google Patents
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- 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
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- 239000003960 organic solvent Substances 0.000 claims description 4
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- 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
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- 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
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- 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
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- 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
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- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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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
本发明属于聚合物制备技术领域，针对芳香酰胺化合物芳香醛基难以发生亲核反应的技术问题，本发明提供一种氮原子低电子云密度的芳香酰胺与芳香醛基制备亲水化合物的方法，将含有多芳香醛基的功能单体和芳香族酰胺化合物溶于有机溶剂，然后加入醋酸溶液作为催化剂，充分混合，加热至50‑120℃，反应4‑24h，生成所述的亲水有机聚合物。本发明能够能够简单、快速的制备得到亲水有机聚合物。
Description
技术领域
本发明属于聚合物制备技术领域，具体涉及一种亲水有机聚合物的制备方法。
背景技术
席夫碱反应是醛类化合物与胺类化合物制备有机聚合物的一种重要方式。芳香醛类化合物与芳香胺类化合物的席夫碱缩合反应已经应用于制备共价有机骨架、有机多孔聚合物及自聚微孔聚合物等。芳香酰胺化合物是有甲酰基取代的芳香化合物，由于具有芳环和酰胺的共轭，以及酰胺本身结构特性，氮原子上电子云密度很低，比脂肪族氨基和芳香氨基更难与芳香醛基发生亲核反应。氮原子上电子云密度较多的脂肪族氨基和芳香氨基常与芳香醛基形成疏水的材料，我们希望发展一种氮原子低电子云密度的芳香酰胺与芳香醛基制备亲水化合物的新方法。
目前，基于芳香酰胺化合物与芳香醛基化合物的聚合反应制备有机聚合物尚未见报道。
发明内容
针对芳香酰胺化合物芳香醛基难以发生亲核反应的上述问题，本发明提供一种亲水有机聚合物的制备方法，以醋酸溶液作为催化剂，将含有多芳香醛基的功能单体、芳香族酰胺化合物以及反应溶剂混合，超声溶解，然后在加热条件下发生聚合反应即可一步制备出亲水有机聚合物。
本发明的技术方案如下：
一种亲水有机聚合物的制备方法，将含有多芳香醛基的功能单体和芳香族酰胺化合物溶于有机溶剂，然后加入醋酸溶液作为催化剂，充分混合，加热至50-120℃，反应4-24h，生成所述的亲水有机聚合物。
进步一的：所述的含有多芳香醛基的功能单体为均苯三甲醛和/或者三甲酰基均苯三酚，所述的芳香族酰胺化合物为对苯二甲酰胺和/或均苯三甲酰胺。
进步一的：所述有机溶剂为N,N-二甲基甲酰胺、1,4-二氧六环或者二甲基亚砜。
进步一的：所述含有芳香醛基的功能单体和芳香族酰胺化合物的质量比为：(3-7):(2-4)。
有益效果：所述的制备方法操作简便且反应速度快。所述制备的有机聚合物具有亲水性，有望用于糖肽富集、环境污染物的样品预处理或者极性药物分子的载药***评价。
附图说明
图1为实施例1制得的亲水有机聚合物的扫描电镜图。
图2为实施例2制得的亲水有机聚合物的扫描电镜图。
图3为实施例1制得的亲水有机聚合物的接触角。
具体实施方式
下面结合具体实施例对本发明做进一步详细说明。
实施例1
向圆底烧瓶中加入48mg均苯三甲醛、32mg对苯二甲酰胺、3mL的N,N-二甲基甲酰胺，超声15min使其中的各个组分混合均匀；将上述圆底烧瓶。置于60℃水浴锅中反应6小时；用甲醇清洗产物，将其中的反应溶剂及一些未参与反应的物质冲出即得到亲水有机聚合物。
如图1所示，制备的亲水有机聚合物形貌特点是不规则的堆积状聚合物。
实施例2
向圆底烧瓶中加入48mg均苯三甲醛、32mg对苯二甲酰胺、3mL的N,N-二甲基甲酰胺，超声15min使其中的各个组分混合均匀；将上述圆底烧瓶置于120℃气相炉中反应3天；用甲醇清洗产物，将其中的反应溶剂及一些未参与反应的物质冲出即得到亲水有机聚合物。
如图2所示，制备的亲水有机聚合物形貌特点是大小不均的长方体状材料。
实施例3
向圆底烧瓶中加入60mg三甲酰基均苯三酚、60mg均苯三甲酰胺、3mL二甲基亚砜，超声15min使其中的各个组分混合均匀；将上述圆底烧瓶置于120℃气相炉中反应3天；用甲醇清洗产物，将其中的反应溶剂及一些未参与反应的物质冲出即得到亲水有机聚合物。
性能及用途
采用基于液面形状分析的光学法，直接测量实施例1制备的亲水有机聚合物的接触角，如图3所示，接触角为64°左右，证明为亲水性材料。
由于具有亲水性质，所制备材料有望用于糖肽富集、环境污染物的样品预处理或者极性药物分子的载药***评价。
以上所述的实施例仅是对本发明的优选实施方式进行描述，并非对本发明的范围进行限定，在不脱离本发明设计精神的前提下，本领域普通技术人员对本发明的技术方案作出的各种变形和改进，均应落入本发明权利要求书确定的保护范围内。
Claims (3)
1.一种亲水有机聚合物的制备方法，其特征在于：将含有多芳香醛基的功能单体和芳香族酰胺化合物溶于有机溶剂，然后加入醋酸溶液作为催化剂，充分混合，加热至50-120℃，反应4-24h，生成所述的亲水有机聚合物；
所述的含有多芳香醛基的功能单体为均苯三甲醛和/或者三甲酰基均苯三酚，所述的芳香族酰胺化合物为对苯二甲酰胺和/或均苯三甲酰胺。
2.根据权利要求1所述的制备方法，其特征在于：所述有机溶剂为N,N-二甲基甲酰胺、1,4-二氧六环或者二甲基亚砜。
3.根据权利要求1所述的制备方法，其特征在于：所述含有芳香醛基的功能单体和芳香族酰胺化合物的质量比为：(3-7):(2-4)。
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| KR900009759A (ko) * | 1988-12-01 | 1990-07-05 | 한국과학기술원 | N,n'-비스-4,3'-디아미노디페닐에테르의 단량체 단위를 포함한 신규의 방향족 폴리아미드 |
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| CN113845665A (zh) * | 2021-09-28 | 2021-12-28 | 天津大学 | 一种全共轭有机三嗪骨架材料及其制备方法和应用 |
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| 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 |
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