CN114478916B - N-vinyl pyrrolidone-methacrylate random copolymer and preparation method thereof - Google Patents
N-vinyl pyrrolidone-methacrylate random copolymer and preparation method thereof Download PDFInfo
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- CN114478916B CN114478916B CN202210145741.3A CN202210145741A CN114478916B CN 114478916 B CN114478916 B CN 114478916B CN 202210145741 A CN202210145741 A CN 202210145741A CN 114478916 B CN114478916 B CN 114478916B
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- vinyl pyrrolidone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
Abstract
The invention relates to the field of polymer preparation, in particular to an N-vinyl pyrrolidone-methacrylate random copolymer, the structural formula of which is shown as (I), wherein R is a saturated alkyl carbon chain, and R' is a hydrogen atom or a saturated alkyl carbon chain with a functional group. The preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer comprises the following steps: preparing a catalyst solution; the catalyst comprises a free radical initiator and a reversible addition-fragmentation chain transfer agent; the N-vinyl pyrrolidone-methacrylate binary random copolymer is obtained by taking N-vinyl pyrrolidone-based monomer and methacrylate monomer as raw materials and carrying out catalytic polymerization reaction at 50-80 ℃ by using the catalyst solution. The binary random copolymer prepared by the invention is an amphiphilic polymer with adjustable structural composition and performance, and has wide application prospect in the fields of intelligent materials, adhesives, coatings, medicine and the like.
Description
Technical Field
The invention relates to the technical field of polymer preparation, in particular to an N-vinyl pyrrolidone-methacrylate random copolymer and a preparation method thereof.
Background
The N-vinyl pyrrolidone structurally contains a nonpolar group methylene and a strong polar group lactam, so that the N-vinyl pyrrolidone has both hydrophilic and oleophilic effects. Because of the higher electron density on the pyrrolidone ring, polyvinylpyrrolidone exhibits excellent surface activity properties and has a strong ability to form hydrogen bonds and complexes, especially with polar groups (hydroxyl groups, carbonyl groups, amine groups, etc.), and with compounds having active hydrogen atoms. Polyvinylpyrrolidone has many extremely excellent properties, is especially free from participating in metabolism of human bodies, has good biocompatibility and biodegradability, is widely used in the fields of medical and health, daily chemical industry, sewage treatment, batteries, paint and the like, and is one of the most attractive professional technical polymers in the chemical field.
Methacrylic esters are readily polymerizable, commercially important hydrophobic monomers, which provide polymers with excellent film forming and hydrophobicity properties, and which are soluble in common organic solvents but insoluble in water. Good chemical resistance and stability, compact structure, low glass transition temperature, and great significance in material science. The methacrylate has wide application prospect in oil absorption materials, lubricating oil additives, antifouling coatings, water repellents and the like.
How to realize the copolymerization of N-vinyl pyrrolidone-based monomer and methacrylate-based monomer, thereby realizing the excellent amphiphilic property of the copolymer is the main content to be studied.
Disclosure of Invention
In order to solve the problems, the invention aims to provide a preparation method of an N-vinyl pyrrolidone-methacrylate random copolymer, which is an amphiphilic polymer with polyvinylpyrrolidone and polymethacrylate polymers, and adds new content to a high-molecular polymer.
In order to achieve the above purpose, the invention adopts the following technical scheme: an N-vinyl pyrrolidone-methyl acrylic ester random copolymer with a structural formula shown as (I),
wherein R is a saturated alkyl carbon chain, and R' is a hydrogen atom or a saturated alkyl carbon chain with a functional group.
The preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer comprises the following steps:
a) Dispersing a catalyst in an organic solvent to obtain a catalyst solution; the catalyst is a free radical initiator;
b) The N-vinyl pyrrolidone-methacrylate binary random copolymer is obtained by taking N-vinyl pyrrolidone-based monomer and methacrylate monomer as raw materials, catalyzing polymerization reaction at 50-80 ℃ by using the catalyst solution, and adding a terminator.
The preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer comprises the following steps:
a) Dispersing a catalyst in an organic solvent to obtain a catalyst system; the catalyst comprises: a free radical initiator and a RAFT chain transfer agent;
b) The N-vinyl pyrrolidone-methacrylate binary random copolymer is obtained by taking N-vinyl pyrrolidone-based monomer and methacrylate monomer as raw materials, catalyzing polymerization reaction at 50-80 ℃ by using the catalyst solution, and adding a terminator.
The preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer comprises the step of preparing the free radical initiator, wherein the free radical initiator comprises azodiisobutyronitrile, diacyl peroxide and persulfate.
The preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer comprises the step of adding a RAFT chain transfer agent, wherein the RAFT chain transfer agent comprises trithiocarbonate or dithiocarboxylate.
The preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer comprises the following step b):
firstly, mixing N-vinyl pyrrolidone monomer with lauryl methacrylate, placing the mixture in an ampoule bottle, then mixing the mixture with the catalyst solution prepared in the step a), catalyzing polymerization reaction at 50-80 ℃, stopping the reaction after a certain time, settling the product, and drying to obtain the N-vinyl pyrrolidone-lauryl methacrylate binary random copolymer;
or the step b) is specifically as follows: firstly, mixing a functionalized N-vinyl pyrrolidone monomer with a lauryl methacrylate monomer, placing the mixture into an ampoule bottle, then mixing the mixture with the catalyst solution prepared in the step a), catalyzing the polymerization reaction at 50-80 ℃, stopping the reaction after a certain time, settling the product, and drying to obtain the functionalized N-vinyl pyrrolidone-lauryl methacrylate binary random copolymer.
In the preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer, in the step b), the structural formula of the N-vinyl pyrrolidone monomer is shown as the specification, the structural formula of the functionalized N-vinyl pyrrolidone monomer is shown as the specification (III) or the formula (IV),
the preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer comprises the step of mixing the N-vinyl pyrrolidone-based monomer and the methacrylate monomer in a molar ratio of 0-1000:1000-250.
In the preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer, the terminating agent for terminating the reaction is ethanol solution acidified by hydrochloric acid.
In the preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer, the solvent used for dissolving the polymer in the sedimentation process is dichloromethane and chloroform, and the solvent used for sedimentation of the polymer is cold ethanol.
The preparation method of the N-vinyl pyrrolidone-methacrylate random copolymer provided by the invention comprises free radical copolymerization and RAFT copolymerization, and in the preparation process, the random copolymer with different compositions and structures can be obtained simply by changing the structure and the feeding ratio of the monomers, so that the random copolymer with different performances can be obtained. The one-pot method provides a simple way for customizing the amphiphilic polymer, and has potential application prospect in the fields of preparing high-performance materials and self-assembly thereof.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of copolymer P (TBSE-NVP) -co-PLMA synthesized in example 1.
FIG. 2 is an infrared spectrum of the copolymer P (TBSE-NVP) -co-PLMA synthesized in example 1.
FIG. 3 is a GPC chart of copolymer P (TBSE-NVP) -co-PLMA synthesized in example 1.
FIG. 4 is a thermogram of copolymer P (TBSE-NVP) -co-PLMA synthesized in example 1.
Detailed Description
EXAMPLE 1 functionalized random copolymer of N-vinylpyrrolidone and lauryl methacrylate P (TBSE-NVP) -co-PLMA
The structural formula (I) is as follows:
the preparation method of the second component is as follows:
synthesis of monofunctional N-vinylpyrrolidone monomer and methacrylate monomer copolymer (P (TBSE-NVP) -co-PLMA):
a quantity of toluene solution (10 mL) of Azobisisobutyronitrile (AIBN) (10. Mu. Mol) and different molar ratios (2.5 mmol:7.5mmol, 5.0mmol:5.0mmol, 7.5mmol:2.5 mmol) of monofunctional N-vinylpyrrolidone monomer and dodecyl methacrylate (LMA) monomer were placed in an ampoule under an anhydrous oxygen-free nitrogen atmosphere and reacted at 70℃for 24 hours before the reaction was terminated by rapid addition of ethanol acidified with 10% hydrochloric acid. The polymer solution was poured into 50mL of cold ethanol, the polymer was allowed to settle out, and after suction filtration, a white solid was obtained. It was dissolved again in dichloromethane and allowed to settle with cold ethanol, and the process was repeated three times to remove unreacted monomer. The polymer was dried to constant weight in a vacuum oven at 40℃to give the product P (TBSE-NVP) -co-PLMA.
(III) characterization
The product undergoes nuclear magnetic resonance hydrogen spectrum 1 H-NMR), fourier transform infrared (FT-IR), gel Permeation Chromatography (GPC), thermogravimetric (TGA) and the like, as shown in FIGS. 1-4.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a synthetic copolymer P (TBSE-NVP) -co-PLMA 1 H-NMR(300MHz,CDCl 3 298K), it can be seen that the chemical shift of the P (TBSE-NVP) homopolymer occurs during the TBSE-NVP/LMA monomer ratio from 250:750 to 750:250, we first found the chemical shift of the PLMA segment, 3.19ppm being the O-CH of PLMA 2 Chemical shift, secondly, we found that chemical shift of P (TBSE-NVP) occurred near 3.67ppm and 3.05ppm, respectivelyP (TBSE-NVP) homopolymer-CH 2 O-, -N-CH and-CH 2 Chemical shift of N-.
FIG. 2 is an infrared spectrum (FT-IR) of the synthesized copolymer P (TBSE-NVP) -co-PLMA, as can be seen: in the process of the monomer ratio of TBSE-NVP/LMA from 250:750 to 750:250, the copolymer has the characteristic absorption peaks of PLMA and P (TBSE-NVP), and the characteristic peak intensity of P (TBSE-NVP) is sequentially enhanced along with the increase of the monomer feeding ratio, which shows that the two monomers are subjected to free radical polymerization in the copolymerization, and is consistent with the result obtained in a nuclear magnetic hydrogen spectrum.
FIG. 3 is a GPC chart of the synthetic copolymer P (TBSE-NVP) -co-PLMA, as can be seen in the figure: GPC was unimodal, indicating that the TBSE-NVP monomer copolymerized into the PLMA macromolecular chain to form copolymer P (TBSE-NVP) -co-PLMA.
The above characterization confirmed the successful synthesis of the functionalized N-vinylpyrrolidone monomer and lauryl methacrylate copolymer (P (TBSE-NVP) -co-PLMA).
FIG. 4 is a Thermogravimetric (TGA) curve of copolymer P (TBSE-NVP) -co-PLMA, as can be seen: the thermal weight loss of the copolymer P (TBSE-NVP) -co-PLMA under nitrogen atmosphere mainly occurs at 300-500 ℃. Random copolymer P (TBSE-NVP) 250 -co-PLMA 750 The initial decomposition temperature of the polymer is about 312.34 ℃, the polymer degradation rate is 369.45 ℃ at the highest speed, and when the temperature reaches 424.96 ℃, the polymer is completely pyrolyzed, and the carbon residue tends to 0; random copolymer P (TBSE-NVP) 500 -co-PLMA 500 The initial decomposition temperature of the polymer is about 354.41 ℃, the polymer degradation rate is 394.97 ℃ at the highest speed, and when the temperature reaches 450.70 ℃, the polymer is completely pyrolyzed, and the carbon residue tends to 0; random copolymer P (TBSE-NVP) 750 -co-PLMA 250 The initial decomposition temperature of (2) was around 359.46 ℃and the polymer degradation rate occurred at 428.72 ℃at maximum. At a temperature of 468.53 ℃, the polymer was completely pyrolyzed and the carbon residue was about 0.89%. Random copolymer P (TBSE-NVP) -co-PLMA vs P (TBSE-NVP) polymer with reduced thermal stability; compared with PLMA, the thermal stability of the PLMA is improved. As the ratio of TBSE-NVP/LMA increases, the content of P (TBSE-NVP) segments increasesThe thermal stability is improved.
Claims (7)
1. An N-vinyl pyrrolidone-methyl acrylate random copolymer is characterized in that the structural formula is shown as (I),
，
（Ⅰ）
wherein R is a saturated alkyl carbon chain, and R' is a saturated alkyl carbon chain with a functional group;
the structural formula of the functionalized N-vinyl pyrrolidone monomer is shown as a formula (III) or a formula (IV),
；
（Ⅲ）、 （Ⅳ）；
the molar ratio of the N-vinyl pyrrolidone-based monomer to the methacrylate monomer is 0-1000:1000-250, wherein the dosage of the N-vinyl pyrrolidone-based monomer is not 0.
2. The method for preparing the N-vinyl pyrrolidone-methyl acrylate random copolymer according to claim 1, which is characterized by comprising the following steps:
a) Dispersing a catalyst in an organic solvent to obtain a catalyst solution; the catalyst is a free radical initiator;
b) The N-vinyl pyrrolidone-methacrylate binary random copolymer is obtained by taking an N-vinyl pyrrolidone-based monomer and a methacrylate monomer as raw materials, carrying out catalytic polymerization reaction at 50-80 ℃ by using the catalyst solution, and adding a terminator.
3. The method for preparing the N-vinyl pyrrolidone-methyl acrylate random copolymer according to claim 1, comprising the following steps:
a) Dispersing a catalyst in an organic solvent to obtain a catalyst system; the catalyst comprises: a free radical initiator and a RAFT chain transfer agent;
b) The N-vinyl pyrrolidone-methacrylate binary random copolymer is obtained by taking an N-vinyl pyrrolidone-based monomer and a methacrylate monomer as raw materials, carrying out catalytic polymerization reaction at 50-80 ℃ by using the catalyst solution, and adding a terminator.
4. A process for the preparation of an N-vinylpyrrolidone-methacrylate random copolymer according to claim 2 or 3, wherein the free radical initiator comprises azobisisobutyronitrile, persulphate.
5. A method of preparing an N-vinylpyrrolidone-methacrylate random copolymer according to claim 3, wherein the RAFT chain transfer agent comprises a trithiocarbonate or dithiocarboxylate.
6. A process for the preparation of an N-vinylpyrrolidone-methacrylate random copolymer according to claim 2 or 3, characterized in that step b) is specifically: firstly, mixing a functionalized N-vinyl pyrrolidone monomer with a lauryl methacrylate monomer, placing the mixture in an ampoule bottle, then mixing the mixture with the catalyst solution prepared in the step a), carrying out catalytic polymerization reaction at 50-80 ℃, stopping the reaction after a certain time, settling the product, and drying to obtain the functionalized N-vinyl pyrrolidone-lauryl methacrylate binary random copolymer.
7. A process for the preparation of an N-vinylpyrrolidone-methacrylic acid ester random copolymer according to claim 2 or 3, characterized in that the termination agent for the termination reaction is an ethanol solution acidified with hydrochloric acid.
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