CN108948303A - One kind is based on porous polyamides base amino ureas material and preparation method and application - Google Patents

One kind is based on porous polyamides base amino ureas material and preparation method and application Download PDF

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CN108948303A
CN108948303A CN201710355969.4A CN201710355969A CN108948303A CN 108948303 A CN108948303 A CN 108948303A CN 201710355969 A CN201710355969 A CN 201710355969A CN 108948303 A CN108948303 A CN 108948303A
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preparation
base amino
reaction
added
polyamides base
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CN108948303B (en
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欧俊杰
王红卫
叶明亮
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Dalian Institute of Chemical Physics of CAS
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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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
    • C08G18/3834—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing hydrazide or semi-carbazide groups
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/14—Manufacture of cellular products
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
    • C08J9/286—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum the liquid phase being a solvent for the monomers but not for the resulting macromolecular composition, i.e. macroporous or macroreticular polymers
    • 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
    • C08G2101/00—Manufacture of cellular products
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Abstract

The present invention relates to a kind of preparation methods based on porous polyamides base amino ureas material; specifically the function monomer containing hydrazides group, isocyanate crosslinking and reaction dissolvent are mixed; ultrasonic dissolution is simultaneously added in reaction kettle, then in a heated condition occur polymerization reaction can a step prepare porous polyamides base amino ureas material.A series of porous polyamides base amino ureas materials with different physics and chemical property can be prepared by the function monomer and crosslinking agent of selecting various concentration.

Description

One kind is based on porous polyamides base amino ureas material and preparation method and application
Technical field
The present invention relates to a kind of preparation methods based on porous polyamides base amino ureas material, will specifically contain hydrazide group Function monomer, isocyanate crosslinking and the reaction dissolvent of group mix, and ultrasonic dissolution is simultaneously added in reaction kettle, is then adding Under heat condition occur polymerization reaction can a step prepare porous polyamides base amino ureas material.
Background technique
Protein glycosylation is one of most important posttranslational modification, it rises emphatically in the biological process of many keys The adjustment effect wanted.Glycosylation is abnormal closely related with a variety of diseases of the mankind, therefore the detection and identification of glycoprotein is to disease Diagnosing and treating has great importance.Currently, mass-spectrometric technique is because of its higher point in the analysis of glycoprotein or glycopeptide Resolution and sensitivity and be widely applied.However, the abundance of glycopeptide is usually lower in actual sample, these glycopeptide pickup electrodes Interference vulnerable to non-glycopeptide.Therefore, before mass spectral analysis, glycopeptide enrichment is very necessary.
Currently, a variety of methods such as agglutinin affinity chromatography, hydrazide chemistry, boric acid chemistry and hydrophilic Interaction Chromatography are widely applied The enrichment of glycopeptide in complex biological sample.In these methods, hydrophilic Interaction Chromatography is because its enrichment process is simple, enrichment condition temperature With and reproducibility preferably and by common concern.Recently, researchers have developed a plurality of types of hydrophilic chromatographic stationary phases, such as Both sexes silica gel or polymer, maltose, agarose, cellulose and MOFs material, and they are applied in glycopeptide enrichment.If Meter and exploration novel hydrophilic stationary phase remain one of the hot spot of glycopeptide enrichment research.
In recent years, porous organic material (POPs) have that preparation is simple, specific surface area is larger and chemical and thermal stability compared with The advantages that good and receive and pay close attention to relatively broadly.Such as inherent microporous polymer (PIMs) of such material, conjugation microporous polymer Object (CMPs), porous aromatic skeleton (PAFs) and covalent organic framework (COFs) usually by polymerization/concentration, solvent thermal reaction or Person's metal mediates coupling/addition reaction preparation.Currently, they have been successfully applied to gas storage, catalysis and specimen preprocessing The fields such as reason.
Farago etc. reports polyamides base amino ureas material for the first time.Up to the present, only a small amount of article and this material Expect related, and the polyamides base amino ureas material being had been reported that is linear polymer.Porous polyamides base amino ureas material So far it does not have been reported that.In recent years, Bhunia etc. reports the preparation of polyureas porous organic polymer and its as pharmaceutical carrier Diagnosing and treating applied to liver cancer.This quasi polymer passes through 2,4,6- triamido pyridine and paraphenylene diisocyanate (PDI) Organosol-gel reaction preparation, the material have random mesoporous, specific surface area 142m2/g.It is similar, herein It is reacted by equal three formylhydrazine of benzene with PDI generation one-step polymerization and is prepared for a kind of polyamides base amino ureas porous organic polymer (Fig. 1).Since the material has hydrophily, therefore attempted to be used in the glycopeptide enrichment of immunoglobulin G (IgG) enzymolysis liquid.
Summary of the invention
The present invention provides a kind of preparation methods based on porous polyamides base amino ureas material, will specifically contain hydrazides Function monomer, isocyanate crosslinking and the reaction dissolvent of group mix and ultrasonic dissolution, then occurs in a heated condition Porous polyamides base amino ureas material can be prepared in polymerization reaction.
The technical solution adopted by the present invention are as follows:
Preparation method based on porous polyamides base amino ureas material: by the function monomer containing hydrazides group, isocyanic acid Ester crosslinking agent and reaction dissolvent mixing, ultrasonic dissolution are simultaneously added in reaction kettle, and it is anti-that polymerization then occurs in a heated condition Should can a step prepare porous polyamides base amino ureas material.
Detailed process is as follows for it:
1) function monomer that 168-252mg contains hydrazides group is added into centrifuge tube；
2) 160-240mg isocyanate crosslinking is added into the centrifuge tube of step 1)；
3) 3.3mL dimethyl sulfoxide is added into above-mentioned centrifuge tube.
4) by above-mentioned mixed system ultrasound 10-15min at normal temperature, homogeneous solution is formed；
5) mixed solution obtained in step 4) is added in reaction kettle；
6) reaction kettle for filling mixed solution obtained in step 5) is placed in 90-110 degrees Celsius of reacting furnace instead Answer 48-72h；
7) white solid product in aforesaid reaction vessel is respectively washed using dimethyl sulfoxide and ethyl alcohol, it is molten with removal reaction Agent and small molecule oligomer.
The present invention is based on the preparation process of porous polyamides base amino ureas material signal formula is as follows:
Function monomer containing hydrazides group used in the step 1) is equal three formylhydrazine of benzene；It is adopted in the step 2) Isocyanate crosslinking is paraphenylene diisocyanate；And 7) step 5), 6) reaction kettle specification used in is 50mL。
The preparation method is easy to operate.It can be with by the function monomer and isocyanate crosslinking of selecting various concentration Prepare a series of porous polyamides base amino ureas materials with different physics and chemical property.
Detailed description of the invention
Fig. 1 is (I) three formylhydrazine of benzene, (II) paraphenylene diisocyanate and (III) polyamides base amino ureas in embodiment 1 The FT-IR map of material.
Fig. 2 is (A and B) the TEM figure and (C and D) SEM figure of polyamides base amino ureas material made from embodiment 1.
Fig. 3 is the MALDI- that polyamides base amino ureas material made from embodiment 1 is applied to glycopeptide enrichment in IgG enzymolysis liquid TOF/MS figure: (A) enzymolysis liquid direct injected, (B) is after material enrichment and the enrichment of (C) material again through glycosidase deglycosylation.
Fig. 4 (I) is the MALDI- that polyamides base amino ureas material made from embodiment 2 is enriched with glycopeptide from IgG enzymolysis liquid TOF/MS figure.
Fig. 4 (II) is the MALDI- that polyamides base amino ureas material made from embodiment 3 is enriched with glycopeptide from IgG enzymolysis liquid TOF/MS figure.
Specific embodiment
Embodiment 1
1, equal three formylhydrazine of benzene of 168mg is added into centrifuge tube.
2, the paraphenylene diisocyanate of 160mg is added into above-mentioned centrifuge tube.
3,3.3mL dimethyl sulfoxide is added into above-mentioned centrifuge tube.
4, it is uniformly mixed each component therein above-mentioned centrifuge tube ultrasound 15min.
5, mixed solution obtained in step 4 is added in reaction kettle.
6, the reaction kettle in step 5 is placed in 100 degrees Celsius of gas phase furnaces and reacts 72h.
7, with dimethyl sulfoxide and ethyl alcohol cleaning material, to remove reaction dissolvent and small molecule oligomer.
Embodiment 2
1, equal three formylhydrazine of benzene of 168mg is added into centrifuge tube.
2, the paraphenylene diisocyanate of 240mg is added into above-mentioned centrifuge tube.
3,3.3mL dimethyl sulfoxide is added into above-mentioned centrifuge tube.
4, it is uniformly mixed each component therein above-mentioned centrifuge tube ultrasound 15min.
5, mixed solution obtained in step 4 is added in reaction kettle.
6, the reaction kettle in step 5 is placed in 100 degrees Celsius of gas phase furnaces and reacts 72h.
7, with dimethyl sulfoxide and ethyl alcohol cleaning material, to remove reaction dissolvent and small molecule oligomer.
Embodiment 3
1, equal three formylhydrazine of benzene of 252mg is added into centrifuge tube.
2, the paraphenylene diisocyanate of 160mg is added into above-mentioned centrifuge tube.
3,3.3mL dimethyl sulfoxide is added into above-mentioned centrifuge tube.
4, it is uniformly mixed each component therein above-mentioned centrifuge tube ultrasound 15min.
5, mixed solution obtained in step 4 is added in reaction kettle.
6, the reaction kettle in step 5 is placed in 100 degrees Celsius of gas phase furnaces and reacts 72h.
7, with dimethyl sulfoxide and ethyl alcohol cleaning material, to remove reaction dissolvent and small molecule oligomer.
Fig. 1 is the FT-IR spectrum of (I) PDI, (II) BTZ and 1 material prepared of (III) embodiment.Wherein, 2274cm-1(A) The peak-to-peak signal at place is attributed to the isocyanate groups in PDI, 3298 cm-1The broad peak at place is the level-one amine signal in BTZ, 1647cm-1(B) peak-to-peak signal at is the mixed signal of level-one amine and carbonyl.In the FT-IR map (C) of material, since reaction disappears Level-one amine, 3298cm are consumed-1Bands of a spectrum (B) in the bands of a spectrum ratio BTZ at place narrow.And 1562cm-1(C) peak-to-peak signal at can belong to For the bending vibration of N-H in urea unit.Reduction, the disappearance of isocyanates signal and the showing for urea unit of level-one amino PDI and BTZ have successfully carried out polymerization reaction.
Fig. 2 is that the TEM and SEM of 1 material prepared of embodiment scheme.From TEM figure (Fig. 2A and Fig. 2 B) as can be seen that the polymerization Object has hair-like nanometer bundle pattern, and this pattern is similar with the pattern of porous polyureas material.SEM schemes (Fig. 2 C and Fig. 2 D) table Bright material has spongy pattern, and macropore is cross-linked with each other in structure, and hole size is differed from several hundred nanometers to several microns.
Fig. 3 is enrichment figure of 1 material prepared of embodiment for low abundance glycopeptide in IgG sample under hydrophilic chromatographic mode. Firstly, the effect being enriched with using IgG enzymolysis liquid evaluation material to glycopeptide.Before enrichment, the higher signal of middle peak of spectrogram intensity is Non- glycopeptide, glycopeptide can not almost detect (Fig. 3 A).After enrichment, non-glycopeptide is significantly reduced, while can detecte to 19 typical cases N- connection glycopeptide (Fig. 3 B).It is glycopeptide to verify the peptide fragment of enrichment, peptide fragment carries out deglycosylation processing using glycosidase. As a result, it has been found that glycopeptide signal all disappears in Fig. 3 B, and it is only capable of detecting two peptide segment signals (EEQFNSTFR, m/z in Fig. 3 C =1158.54；EEQYNSTYR, m/z=1158.52), this illustrates that material selects abundance glycopeptide low in IgG enrichment with higher Selecting property.
Fig. 4 is embodiment 2 (I) under hydrophilic chromatographic mode and (II) material prepared of embodiment 3 for low in IgG sample The enrichment figure of abundance glycopeptide.Two kinds of materials all have preferable enrichment performance to the glycopeptide in IgG enzymolysis liquid.
Remarks: glycopeptide enrichment process is as follows: the glycopeptide in 1mg material enrichment IgG enzymolysis liquid is respectively adopted.Detailed process is such as Under, first by 200 μ L sample solution (ACN/H of IgG (9 μ g)2O/TFA, 88/11.9/0.1, v/v/v) dilution, after material is added, Room temperature shakes 10min.Centrifugation removes supernatant.Then it is cleaned using sample solution (400 L × 3 μ), to remove non-glycopeptide and other Impurity.It is subsequently added into 60 μ L eluent (ACN/H2O/TFA, 30/69.9/0.1, v/v/v) and room temperature concussion 10min after, mixing Object centrifugation, takes supernatant to be analyzed using MALDI-TOF/MS.In addition, 60 μ L are added and contain after supernatant is freeze-dried The 10mM NH of 1000U PNGase F4HCO3Solution (pH=8.0) is incubated for 12h at 37 DEG C, to remove glycosyl segment.Finally adopt Deglycosylation peptide fragment is analyzed with MALDI-TOF/MS.

Claims (8)

1. the preparation method based on porous polyamides base amino ureas material, it is characterised in that:
Function monomer and isocyanate crosslinking containing hydrazides group are being heated for reaction dissolvent using dimethyl sulfoxide Under the conditions of in polymerization reaction occurs in reaction kettle, can a step prepare porous polyamides base amino ureas material.
2. preparation method according to claim 1, it is characterised in that: the function monomer containing hydrazides group is equal Three formylhydrazine of benzene, the isocyanate crosslinking are paraphenylene diisocyanate.
3. preparation method according to claim 1 or 2, it is characterised in that: its process is as follows,
1) function monomer that 168-252mg contains hydrazides group is added into centrifuge tube；
2) 160-240mg isocyanate crosslinking is added into the centrifuge tube of step 1)；
3) reaction dissolvent of 3.3mL dimethyl sulfoxide is added into the centrifuge tube of step 2)；
4) by above-mentioned mixed system ultrasound 10-15min at normal temperature, homogeneous solution is formed；
5) mixed solution obtained in step 4) is added in reaction kettle；
6) reaction kettle for filling mixed solution obtained in step 5) is placed in 90-110 degrees Celsius of gas phase furnace and reacts 48- 72h；
7) white solid product in aforesaid reaction vessel is respectively washed using dimethyl sulfoxide and ethyl alcohol, with remove reaction dissolvent and Small molecule oligomer.
The step 5), 6) and 7) 4. preparation method according to claim 3, it is characterised in that: reaction kettle used in Specification is 50mL.
5. preparation method according to claim 1,2 or 3, it is characterised in that: the function monomer containing hydrazides group with it is different The mass ratio of isocyanate cross-linking agent are as follows: 42-63:40-60.
6. according to claim 1, preparation method described in 3 or 5, it is characterised in that: the function monomer containing hydrazides group is in anti- Answering the mass concentration in solvent is 4.4%-6.9%.
7. the porous polyamides base amino ureas material that a kind of any preparation method of claim 1-6 prepares.
8. porous polyamides base amino ureas material is in glycopeptide richness pooled applications described in a kind of claim 7.
CN201710355969.4A 2017-05-19 2017-05-19 Material based on porous polyacylsemicarbazide, preparation method and application Active CN108948303B (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113698598A (en) * 2020-05-22 2021-11-26 中国科学院大连化学物理研究所 Nitrogen-rich porous organic polymer material, preparation and application
CN114957591A (en) * 2022-03-24 2022-08-30 万华化学集团股份有限公司 Preparation method of COF-based polyurethane porous membrane for drug sustained release

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113698598A (en) * 2020-05-22 2021-11-26 中国科学院大连化学物理研究所 Nitrogen-rich porous organic polymer material, preparation and application
CN113698598B (en) * 2020-05-22 2022-08-30 中国科学院大连化学物理研究所 Nitrogen-rich porous organic polymer material, preparation and application
CN114957591A (en) * 2022-03-24 2022-08-30 万华化学集团股份有限公司 Preparation method of COF-based polyurethane porous membrane for drug sustained release
CN114957591B (en) * 2022-03-24 2024-04-09 万华化学集团股份有限公司 Preparation method of COF-based polyurethane porous membrane for drug slow release

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