CN112391072B - Hydrophobic long-chain modified L-histidine corrosion inhibitor and preparation method and application thereof - Google Patents

Hydrophobic long-chain modified L-histidine corrosion inhibitor and preparation method and application thereof Download PDF

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CN112391072B
CN112391072B CN202011264507.XA CN202011264507A CN112391072B CN 112391072 B CN112391072 B CN 112391072B CN 202011264507 A CN202011264507 A CN 202011264507A CN 112391072 B CN112391072 B CN 112391072B
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郭丽媛
王海花
李小瑞
孙立宇
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Shaanxi University of Science and Technology
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Abstract

The invention discloses a hydrophobic long-chain modified L-histidine corrosion inhibitor, a preparation method and application thereof, wherein the preparation method comprises the following steps: 1) weighing a certain amount of AKD in a three-neck flask, dissolving in dichloromethane, stirring at a medium temperature for 30min until the AKD is completely dissolved, and adding a small amount of water to continue stirring. 2) Slowly dropping SOCl by using constant-pressure dropping funnel2And reacting for 1h under low-speed stirring. 3) Weighing a certain amount of L-histidine, dispersing in DMSO (dimethyl sulfoxide), and slowly dropwise adding into a three-neck flask. The reaction was stirred for 1 h. 4) Removing redundant solvent through rotary evaporation, extracting with ethanol water solution with the mass fraction of 90%, washing, performing suction filtration, and finally drying in a drying oven at 50 ℃ to constant weight to obtain the white hydrophobic long-chain modified L-histidine corrosion inhibitor solid particles. The hydrophobic long-chain modified L-histidine corrosion inhibitor solves the application problem of L-histidine as a corrosion inhibitor in an environment-friendly aqueous self-repairing anticorrosive coating and a hydrophobic matrix coating, and expands the application range of the L-histidine as the corrosion inhibitor.

Description

Hydrophobic long-chain modified L-histidine corrosion inhibitor and preparation method and application thereof
Technical Field
The invention belongs to the field of anticorrosive coatings, and particularly relates to a hydrophobic long-chain modified L-histidine corrosion inhibitor, and a preparation method and application thereof.
Background
The problems of metal corrosion and corrosion resistance are closely related to the progress of modern science and technology and the development of national economy, corrosion resistance by applying the corrosion inhibitor is an important means for preventing steel from being corroded, and the corrosion inhibitor has the advantages of less investment, simple and convenient operation, good corrosion resistance effect and the like. At present, an amino acid corrosion inhibitor as a green organic corrosion inhibitor which is friendly to the environment and harmless to human bodies becomes an important direction in the field. The L-histidine is an amino acid corrosion inhibitor with excellent corrosion inhibition performance and has wide application prospect. The L-histidine structure contains active carboxyl and amino, so that the L-histidine has good compatibility with an aqueous medium, and can be directly applied to the aqueous medium. However, the medium of the anti-corrosion coating is negative, the high-efficiency anti-corrosion coating is mostly an oil-soluble medium, and the application of L-histidine as a corrosion inhibitor in the oil-soluble medium is limited. Under the large background of pursuing green, environmental protection and water-based in the coating field, the corrosion inhibitor of the anticorrosive coating is often required to be modified, such as microcapsule modification, in order to achieve efficient and long-acting corrosion prevention. The method is to add oil-in-water type corrosion inhibitor-coated microcapsules into a water-based matrix coating. When the coating is damaged by a corrosive medium or an external force, the self-repairing and corrosion-preventing purposes of the coating are achieved by releasing the corrosion inhibitor coated in the microcapsule, and the preparation of the self-repairing and corrosion-preventing coating is realized. The technology also requires that the water-based corrosion inhibitor is subjected to hydrophobic modification, and simultaneously, the corrosion inhibition performance of the corrosion inhibitor is kept.
Disclosure of Invention
The invention discloses a hydrophobic long-chain modified L-histidine corrosion inhibitor, and a preparation method and application thereof, aiming at solving the application problem of L-histidine as a corrosion inhibitor in an environment-friendly water-based self-repairing anticorrosive coating and a hydrophobic matrix coating and expanding the application range of the L-histidine as the corrosion inhibitor.
In order to achieve the purpose, the invention adopts the technical scheme that:
a hydrophobic long-chain modified L-histidine corrosion inhibitor is disclosed, wherein the structural formula of the corrosion inhibitor is as follows:
Figure BDA0002775681500000021
wherein R is a long alkyl chain of C14-22.
A preparation method of a hydrophobic long-chain modified L-histidine corrosion inhibitor comprises the following steps:
dissolving AKD in dichloromethane containing water, heating and stirring until the AKD is completely dissolved, and hydrolyzing to form a first solution;
adding dropwise SOCl to the first solution2Stirring to make it fully react to obtain a second solution;
dispersing L-histidine in DMSO to form an L-histidine solution, dropwise adding the L-histidine solution to the second solution, and stirring to react to obtain a third solution;
and removing the redundant solvent in the third solution, extracting with an ethanol aqueous solution, washing, performing suction filtration, and finally drying to constant weight to obtain solid particles of the white hydrophobic long-chain modified L-histidine corrosion inhibitor.
As a further improvement of the invention, the AKD reaction temperature is 40-55 ℃.
As a further improvement of the invention, the mass ratio of the AKD to the water is 1: 20.
as a further improvement of the invention, the AKD is in combination with SOCl2The ratio of the amounts of substances is 1: (0.8-1.2).
As a further improvement of the invention, the ratio of the amounts of substances of L-histidine to AKD is: 1: (1-3).
As a further improvement of the invention, the drying temperature is 45-60 ℃.
A hydrophobic long-chain modified L-histidine corrosion inhibitor is applied to a water-based self-repairing anticorrosive coating and a hydrophobic matrix coating.
The hydrophobic long-chain modified L-histidine corrosion inhibitor is added into matrix resin to form an anticorrosive coating;
the matrix resin is as follows: epoxy resin, alkyd resin, acrylic resin, polyurethane resin and phenolic resin.
The addition amount of the hydrophobic long-chain modified L-histidine corrosion inhibitor in the matrix resin is as follows: 1 to 5 percent.
Compared with the prior art, the invention has the following advantages:
in order to solve the application problem of the L-histidine serving as the corrosion inhibitor under the above conditions, the invention improves the application of the L-histidine serving as the corrosion inhibitor in the field of self-repairing anticorrosive functional coatings by a method of performing hydrophobic modification on terminal amino groups of the L-histidine by using Alkyl Ketene Dimer (AKD). The reaction conditions of the experimental scheme of the invention are easy to control, and the reaction activity of Alkyl Ketene Dimer (AKD) and the amino group of L-histidine are utilized to carry out amidation reaction, so that the amino acid with strong hydrophilicity is reacted into a product with a hydrophobic long chain. The hydrophobic performance is provided, simultaneously, carboxyl and imino which can complex iron ions in amino acid are reserved, the corrosion inhibition performance of the product is provided, and the reaction process is simple. By utilizing the property that dichloromethane is slightly soluble in water but can dissolve AKD, the water content in AKD hydrolysis reaction is controlled, the subsequent acyl chlorination reaction is not influenced, the reaction surface of AKD and thionyl chloride is enlarged, and the reaction efficiency is improved. L-histidine is modified by Alkyl Ketene Dimer (AKD), the mode is hydrophobic long-chain modification, and the synthesized product has strong hydrophobicity. And the length of the hydrophobic long-chain alkyl chain of the Alkyl Ketene Dimer (AKD) can be selected (C:14-20), and the hydrophobicity of the synthesized product is controllable. According to the invention, the L-histidine is modified by the Alkyl Ketene Dimer (AKD), so that the carbon number of an alkyl chain in the molecular structure of the L-histidine corrosion inhibitor meets the structural requirement of the optimal slow release rate, and the corrosion inhibition effect is improved.
Preferably, when the carbon number of an alkyl chain in the molecular structure of the corrosion inhibitor is 19-22, the corrosion inhibition rate is highest.
According to the invention, the hydrophobic long-chain modification is carried out on the L-histidine, so that the application problem of the L-histidine serving as a corrosion inhibitor in an environment-friendly water-based self-repairing anticorrosive coating and a hydrophobic matrix coating is solved, and the application range of the L-histidine serving as the corrosion inhibitor is expanded.
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FIG. 1 is a synthetic scheme of a hydrophobic long-chain modified L-histidine corrosion inhibitor obtained in example 5.
Detailed Description
The technical solution in the embodiments of the present invention will be clearly and completely described below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention relates to a hydrophobic long-chain modified L-histidine corrosion inhibitor, which has the following structural formula:
Figure BDA0002775681500000041
wherein R is a long alkyl chain of C14-22.
The preparation principle of the hydrophobic long-chain modified L-histidine corrosion inhibitor is as follows:
the reaction activity of Alkyl Ketene Dimer (AKD) is utilized to carry out amidation reaction with the amino group of L-histidine, and the amino acid with strong hydrophilicity is reacted into a product with a hydrophobic long chain. The hydrophobic performance is provided, and simultaneously, carboxyl and imino which can complex iron ions in amino acid are reserved, and the corrosion inhibition performance of the product is provided. The principle is realized by the following reaction:
Figure BDA0002775681500000051
specifically, the invention also provides a preparation method of the hydrophobic long-chain modified L-histidine corrosion inhibitor, which comprises the following steps:
1) weighing a certain amount of AKD in a three-neck flask, dissolving the AKD in dichloromethane containing a small amount of water, stirring for 30min at a medium temperature until the AKD is completely dissolved and hydrolyzing, wherein the medium temperature is 40-55 ℃. The mass ratio of materials was dichloromethane: AKD: h2O＝20：1：1。
2) Slowly dropping SOCl by using constant-pressure dropping funnel2Reacting for 1h under low-speed stirring, wherein AKD and SOCl are reacted2The ratio of the amounts of the substances is: 1: (0.8-1.2).
3) Weighing a certain amount of L-histidine, dispersing in DMSO (dimethyl sulfoxide), and slowly dropwise adding into a three-neck flask. Stirring and reacting for 1h, wherein the ratio of the L-histidine to the AKD substance is as follows: 1: (1-3).
4) Removing excessive solvent by rotary evaporation, extracting with 90% ethanol water solution, washing, vacuum filtering, and oven drying at 50 deg.C to constant weight to obtain white solid granule.
5) In order to verify the corrosion inhibition performance of the product, the prepared product is added into solvent-based matrix resin to prepare an anticorrosive coating, and a slow release rate test is carried out on a tin plate. This procedure was only used to test the corrosion inhibition performance of the product, and it is clear that the application of the product is not limited to solvent-based matrix resins, including: epoxy resins, alkyd resins, acrylic resins, polyurethane resins, phenolic resins; the addition amount of the product in the matrix resin is as follows: 1-5% (mass percentage).
The invention is further illustrated by the following specific examples and figures:
example 1
(1) A defined amount of AKD (5g) was weighed out in a three-necked flask and dissolved in dichloromethane (34g), stirred at 40 ℃ for 30min until the AKD was completely dissolved, and then 0.36g of water was added. Slowly dropping SOCl by using constant-pressure dropping funnel2(0.95g) and reacted for 1 hour with low-speed stirring. 1.55g of L-histidine was weighed out and dispersed in DMSO (dimethyl sulfoxide), and slowly added dropwise to a three-necked flask. The reaction was stirred for 1 h. Removing excessive solvent by rotary evaporation, extracting with 90% ethanol water solution, washing, vacuum filtering, and oven drying at 50 deg.C to constant weight to obtain white solid granule. In order to verify the corrosion inhibition performance of the product, the prepared product is added into solvent-based matrix resin to prepare an anticorrosive coating, and a slow release rate test is carried out on a tin plate. This procedure was only used to test the corrosion inhibition performance of the product, and it is clear that the application of the product is not limited to solvent-based matrix resins.
(2) 5g of the obtained product is added into 100g of epoxy resin to prepare the anticorrosive paint.
Example 2
(1) A defined amount of AKD (5g) was weighed out in a three-necked flask and dissolved in dichloromethane (34g)After stirring at 40 ℃ for 30min until AKD is completely dissolved, 0.36g of water is added. Slowly dropping SOCl by using constant-pressure dropping funnel2(1.19g), and the reaction was carried out for 1 hour with stirring at a low speed. 1.55g L-histidine was weighed out and dispersed in DMSO (dimethyl sulfoxide) and slowly added dropwise to a three-necked flask. The reaction was stirred for 1 h. Removing excessive solvent by rotary evaporation, extracting with 90% ethanol water solution by mass fraction, washing, vacuum filtering, and oven drying at 45 deg.C to constant weight to obtain white solid granule. In order to verify the corrosion inhibition performance of the product, the prepared product is added into solvent-based matrix resin to prepare an anticorrosive coating, and a slow release rate test is carried out on a tin plate. This procedure was only used to test the corrosion inhibition performance of the product, and it is clear that the application of the product is not limited to solvent-based matrix resins.
(2) 1g of the obtained product is added into 100g of acrylate resin to prepare the anticorrosive paint.
Example 3
(1) A defined amount of AKD (5g) was weighed out in a three-necked flask and dissolved in dichloromethane (34g), stirred at 40 ℃ for 30min until the AKD was completely dissolved, and then 0.36g of water was added. Slowly dropping SOCl by using constant-pressure dropping funnel2(1.43g), and the reaction was carried out for 1 hour with stirring at a low speed. 1.55g L-histidine was weighed out and dispersed in DMSO (dimethyl sulfoxide) and slowly added dropwise to a three-necked flask. The reaction was stirred for 1 h. Removing excessive solvent by rotary evaporation, extracting with 90% ethanol water solution, washing, vacuum filtering, and oven drying at 60 deg.C to constant weight to obtain white solid granule. In order to verify the corrosion inhibition performance of the product, the prepared product is added into solvent-based matrix resin to prepare an anticorrosive coating, and a slow release rate test is carried out on a tin plate. This procedure was only used to test the corrosion inhibition performance of the product, and it is clear that the application of the product is not limited to solvent-based matrix resins.
(2) 3g of the obtained product is added into 100g of alkyd resin to prepare the anticorrosive paint.
Example 4
(1) A defined amount of AKD (5g) was weighed out in a three-necked flask and dissolved in dichloromethane (34g), stirred at 40 ℃ for 30min until the AKD was completely dissolved, and then 0.36g of water was added. Slowly dropping SOCl by using constant-pressure dropping funnel2(1.19g), lowThe reaction was carried out for 1h with rapid stirring. 3.1g L-histidine was weighed out and dispersed in DMSO (dimethyl sulfoxide) and slowly added dropwise to a three-necked flask. The reaction was stirred for 1 h. Removing excessive solvent by rotary evaporation, extracting with 90% ethanol water solution, washing, vacuum filtering, and oven drying at 55 deg.C to constant weight to obtain white solid granule. In order to verify the corrosion inhibition performance of the product, the prepared product is added into solvent-based matrix resin to prepare an anticorrosive coating, and a slow release rate test is carried out on a tin plate. This procedure was only used to test the corrosion inhibition performance of the product, and it is clear that the application of the product is not limited to solvent-based matrix resins.
(2) 2g of the obtained product is added into 100g of phenolic resin to prepare the anticorrosive paint.
Example 5
(1) A defined amount of AKD (5g) was weighed out in a three-necked flask and dissolved in dichloromethane (34g), stirred at 40 ℃ for 30min until the AKD was completely dissolved, and then 0.36g of water was added. Slowly dropping SOCl by using constant-pressure dropping funnel2(1.19g), and the reaction was carried out for 1 hour with stirring at a low speed. 4.65g L-histidine was weighed out and dispersed in DMSO (dimethyl sulfoxide) and slowly added dropwise to a three-necked flask. The reaction was stirred for 1 h. Removing excessive solvent by rotary evaporation, extracting with 90% ethanol water solution, washing, vacuum filtering, and oven drying at 50 deg.C to constant weight to obtain white solid granule. In order to verify the corrosion inhibition performance of the product, the prepared product is added into solvent-based matrix resin to prepare an anticorrosive coating, and a slow release rate test is carried out on a tin plate. This procedure was only used to test the corrosion inhibition performance of the product, and it is clear that the application of the product is not limited to solvent-based matrix resins.
(2) 2g of the obtained product is added into 100g of epoxy resin to prepare the anticorrosive paint.
In order to characterize the structural characteristics of a hydrophobic long-chain modified L-histidine corrosion inhibitor, the hydrophobic long-chain modified L-histidine corrosion inhibitor synthesized in example 5 was subjected to nuclear magnetic hydrogen spectroscopy, and the test results are shown below.
1H NMR(300MHz，DMSO)：δ13.00(s，H)，12.89(s，H)，8.73(s，H)， 8.35(s，H)，7.66(s，H)，4.72(t，H)，3.17～2.92(m，2H)，1.53～1.26(t， 4(n-1)H)，0.88(q，3H)ppm。
According to nuclear magnetic data, the hydrophobic long-chain modified L-histidine corrosion inhibitor with a target structure is successfully prepared.
In order to characterize the corrosion inhibition performance of the hydrophobic long-chain modified L-histidine corrosion inhibitor, the synthesized hydrophobic long-chain modified L-histidine corrosion inhibitor is applied to an epoxy resin coating to perform corrosion inhibition comparison with the epoxy resin coating without the corrosion inhibitor, and the experimental results are shown in the following table.
TABLE 1
Figure BDA0002775681500000081
From the test result, the hydrophobic long-chain modified L-histidine corrosion inhibitor prepared by the scheme has high corrosion inhibition rate and good corrosion inhibition performance.
The foregoing is a more detailed description of the invention and it is not intended that the invention be limited to the specific embodiments described herein, but that various modifications, alterations, and substitutions may be made by those skilled in the art without departing from the spirit of the invention, which should be construed to fall within the scope of the invention as defined by the appended claims.

Claims (10)

1. A hydrophobic long-chain modified L-histidine corrosion inhibitor is characterized in that the corrosion inhibitor has a structural formula as follows:
Figure FDA0003256576870000011
wherein R is a long alkyl chain of C14-22.
2. A method for preparing the hydrophobic long-chain modified L-histidine corrosion inhibitor as claimed in claim 1, comprising the steps of:
dissolving AKD in dichloromethane containing water, heating and stirring until the AKD is completely dissolved, and hydrolyzing to form a first solution;
adding dropwise SOCl to the first solution2Stirring to make it fully react to obtain a second solution;
dispersing L-histidine in DMSO to form an L-histidine solution, dropwise adding the L-histidine solution to the second solution, and stirring to react to obtain a third solution;
and removing the redundant solvent in the third solution, extracting with an ethanol aqueous solution, washing, performing suction filtration, and finally drying to constant weight to obtain solid particles of the white hydrophobic long-chain modified L-histidine corrosion inhibitor.
3. The method for preparing the hydrophobic long-chain modified L-histidine corrosion inhibitor according to claim 2, wherein the AKD reaction temperature is 40-55 ℃.
4. The preparation method of the hydrophobic long-chain modified L-histidine corrosion inhibitor according to claim 2, wherein the mass ratio of AKD to water is 1: 20.
5. the method for preparing the hydrophobic long-chain modified L-histidine corrosion inhibitor according to claim 2, wherein the AKD and SOCl are adopted2The ratio of the amounts of substances is 1: (0.8-1.2).
6. The method for preparing the hydrophobic long-chain modified L-histidine corrosion inhibitor according to claim 2, wherein the ratio of the amounts of the L-histidine and the AKD is 1: (1-3).
7. The preparation method of the hydrophobic long-chain modified L-histidine corrosion inhibitor according to claim 2, wherein the drying temperature is 45-60 ℃.
8. The application of the hydrophobic long-chain modified L-histidine corrosion inhibitor disclosed in claim 1 in a waterborne self-repairing anticorrosive coating and a hydrophobic matrix coating.
9. The use according to claim 8, wherein the hydrophobic long-chain modified L-histidine corrosion inhibitor is added to a matrix resin to form an anticorrosive coating;
the matrix resin is as follows: epoxy resin, alkyd resin, acrylic resin, polyurethane resin and phenolic resin.
10. The use according to claim 9, wherein the hydrophobic long-chain modified L-histidine corrosion inhibitor is added in the matrix resin in an amount of: 1 to 5 percent.
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