CN112501617B - Double-hydrophobic-chain modified L-histidine corrosion inhibitor and preparation method and application thereof - Google Patents
Double-hydrophobic-chain modified L-histidine corrosion inhibitor and preparation method and application thereof Download PDFInfo
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Abstract
本发明公开了一种双疏水链改性L‑组氨酸缓蚀剂及其制备方法和应用，制备方法包括：1)称取一定量L‑组氨酸分散于蒸馏水中，搅拌1h并升温至35～40℃后加入Na2CO3调节体系pH为弱碱性；2)将质量分数为50％的ASA无水乙醇溶液每隔30min加入1次，共分4次加入到上述体系中，同时缓慢加入Na2CO3溶液以保持反应体系pH为弱碱性；3)在第4次加完ASA无水乙醇溶液后调节pH至弱碱性后停止加入Na2CO3溶液，将pH调至中性，用质量分数90％乙醇水溶液萃取、洗涤并抽滤，于50℃烘箱内烘干至恒重，得白色固体颗粒。该双疏水链改性L‑组氨酸缓蚀剂，解决了L‑组氨酸作为缓蚀剂在环保型水性自修复防腐涂层及在疏水基体涂层中的应用问题，扩大了L‑组氨酸作为缓蚀剂的应用范围。The invention discloses a double-hydrophobic chain modified L-histidine corrosion inhibitor and a preparation method and application thereof. The preparation method includes: 1) weighing a certain amount of L-histidine and dispersing it in distilled water, stirring for 1 hour and then heating up After reaching 35～40 ℃, add Na 2 CO 3 to adjust the pH of the system to be weakly alkaline; 2) Add ASA absolute ethanol solution with a mass fraction of 50% every 30 minutes, and add it to the above system in 4 times in total, At the same time, slowly add Na 2 CO 3 solution to keep the pH of the reaction system as weakly alkaline; 3) After the fourth addition of ASA anhydrous ethanol solution, adjust the pH to weakly alkaline, stop adding Na 2 CO 3 solution, and adjust the pH to to neutrality, extracted with a mass fraction of 90% ethanol aqueous solution, washed and suction filtered, and dried in a 50°C oven to constant weight to obtain white solid particles. The double hydrophobic chain modified L-histidine corrosion inhibitor solves the application problem of L-histidine as a corrosion inhibitor in environmentally friendly water-based self-healing anti-corrosion coatings and in hydrophobic substrate coatings, and expands L-histidine The scope of application of histidine as a corrosion inhibitor.
Description
Technical Field
The invention belongs to the field of anticorrosive coatings, and particularly relates to a double-hydrophobic-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 provides a double-hydrophobic chain modified L-histidine corrosion inhibitor, 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 double hydrophobic chain modified L-histidine corrosion inhibitor is disclosed, wherein the structural formula of the corrosion inhibitor is as follows:
a preparation method of a double-hydrophobic-chain modified L-histidine corrosion inhibitor comprises the following steps:
dispersing L-histidine in water, stirring, heating to 35-40 ℃, and adding Na2CO3Adjusting the pH value of the system to be alkalescent;
adding ASA absolute ethyl alcohol solution into the systemWhile slowly adding Na2CO3The solution is used for keeping the pH value of the reaction system to be alkalescent;
after adding the ASA absolute ethyl alcohol solution, adjusting the pH value to be alkalescent, and stopping adding Na2CO3Adjusting the pH of the solution to be neutral, extracting with an ethanol water solution, washing, performing suction filtration, and finally drying to constant weight to obtain white solid particles.
As a further improvement of the invention, the mass ratio of the L-histidine to the water is 1-5%.
As a further improvement of the invention, the weakly basic pH is in the range of 7.5 to 9.
As a further development of the invention, the ratio of the amounts of substance of L-histidine to ASA is: 1: (1-3).
As a further improvement of the invention, the drying temperature is 45-60 ℃.
A double-hydrophobic-chain modified L-histidine corrosion inhibitor is applied to a water-based self-repairing anticorrosive coating and a hydrophobic matrix coating.
The double-hydrophobic-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 double-hydrophobic-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 carrying out hydrophobic modification on terminal amino groups of Alkenyl Succinic Anhydride (ASA). The experimental scheme of the invention is a one-step reaction, and the reaction activity of alkenyl succinic anhydride is utilized to perform amidation reaction with amino of L-histidine, so that amino acid with strong hydrophilicity is reacted into a product with double hydrophobic chains. 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 reaction condition is easy to control, and the reaction process is simple. L-histidine is modified by Alkenyl Succinic Anhydride (ASA), the mode is double hydrophobic chain modification, and the synthesized product has strong hydrophobicity. And the chain length of the double hydrophobic chain alkyl of the Alkenyl Succinic Anhydride (ASA) can be selected (C:14-22), and the hydrophobicity of the synthesized product can be controlled. According to the invention, Alkenyl Succinic Anhydride (ASA) is used for modifying L-histidine, 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.
The invention carries out double-hydrophobic chain modification on the L-histidine, solves the application problem of the 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.
Drawings
FIG. 1 is a synthetic scheme of a bis-hydrophobic chain modified L-histidine corrosion inhibitor obtained in example 7;
FIG. 2 nuclear magnetic hydrogen spectrum of a double hydrophobic chain modified L-histidine corrosion inhibitor obtained in example 7.
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 double-hydrophobic-chain modified L-histidine corrosion inhibitor, which has the following structural formula:
the principle for preparing the hydrophobic modified L-histidine corrosion inhibitor is as follows:
by utilizing the reactivity of alkenyl succinic anhydride, amidation reaction is carried out with amino of L-histidine, and amino acid with strong hydrophilicity is reacted into product with double hydrophobic chains. 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:
specifically, the preparation method of the modified L-histidine corrosion inhibitor for the coating with the self-repairing function comprises the following steps:
(1) weighing a certain amount of L-histidine, dispersing in distilled water, wherein the mass ratio of the L-histidine to the water is 1% -5%, stirring for 1h, heating to 35-40 ℃, and adding Na2CO3Adjusting the pH value of the system to be alkalescent;
(2) adding ASA absolute ethanol solution with mass fraction of 50% into the system every 30min for 1 time, adding into the system for 4 times, and slowly adding Na2CO3The solution is used for keeping the pH of the reaction system to be alkalescent, wherein the mass ratio of the L-histidine to the ASA substance is as follows: 1: (1-3);
(3) after the 4 th addition of the ASA absolute ethyl alcohol solution is finished, the pH is adjusted to be alkalescent, and the Na addition is stopped2CO3Adjusting the pH of the solution until the solution is neutral, extracting the solution by using an ethanol water solution with the mass fraction of 90%, washing and filtering the solution, and finally drying the solution in an oven at the temperature of 45-60 ℃ until the weight of the solution is constant, thus obtaining white solid particles.
(4) Adding the obtained product into solvent-based matrix resin to prepare the anticorrosive paint, wherein the matrix resin comprises: epoxy resins, alkyd resins, acrylic resins, polyurethane resins, phenolic resins; the addition amount of the product in the matrix resin is as follows: 1 to 5 percent.
The invention is further illustrated by the following specific examples and figures:
example 1
(1) Weighing a certain amount of L-histidine (1g) and dispersing in distilled water (100ml), stirring for 1h, heating to 35 deg.C, and adding Na2CO3Adjusting the pH value of the system to 8.5; adding ASA absolute ethanol solution with mass fraction of 50% into the system every 30min for 1 time, adding into the system for 4 times, and slowly adding Na2CO3The solution is used for keeping the pH value of the reaction system at 8.5; after the 4 th addition of the ASA absolute ethanol solution is finished, the pH is adjusted to 8.5, and the Na addition is stopped2CO3Adjusting the pH of the solution until the solution is neutral, extracting the solution by using an ethanol water solution with the mass fraction of 90%, washing and filtering the solution, and finally drying the solution in an oven at the temperature of 45 ℃ until the weight of the solution is constant, thus obtaining white solid particles.
(2) 2g of the obtained product is added into 100g of epoxy resin to prepare the anticorrosive paint.
Example 2
(1) Weighing a certain amount of L-histidine (3g) and dispersing in distilled water (100ml), stirring for 1h, heating to 40 ℃, and adding Na2CO3Adjusting the pH value of the system to 8.5; adding ASA absolute ethanol solution with mass fraction of 50% into the system every 30min for 1 time, adding into the system for 4 times, and slowly adding Na2CO3The solution is used for keeping the pH value of the reaction system at 8.5; after the 4 th addition of the ASA absolute ethanol solution is finished, the pH is adjusted to 8.5, and the Na addition is stopped2CO3Adjusting the pH of the solution until the solution is neutral, extracting the solution by using an ethanol water solution with the mass fraction of 90%, washing and filtering the solution, and finally drying the solution in a drying oven at the temperature of 50 ℃ until the weight of the solution is constant, thus obtaining white solid particles.
(2) 2g of the obtained product is added into 100g of alkyd resin to prepare the anticorrosive paint.
Example 3
(1) Weighing a certain amount of L-histidine (5g) and dispersing in distilled water (100ml), stirring for 1h, heating to 38 deg.C, and adding Na2CO3Adjusting the pH value of the system to 8.5; adding ASA absolute ethanol solution with mass fraction of 50% into the system every 30min for 1 time, adding into the system for 4 times, and slowly adding Na2CO3The solution is used for keeping the pH value of the reaction system at 8.5; after the 4 th addition of the ASA absolute ethanol solution is finished, the pH is adjusted to 8.5, and the Na addition is stopped2CO3Adjusting the pH of the solution to be neutral, extracting the solution by using an ethanol water solution with the mass fraction of 90%, washing and filtering the solution, and finally drying the solution in a drying oven at the temperature of 60 ℃ until the solution is neutralConstant weight to obtain white solid particles.
(2) 2g of the obtained product is added into 100g of acrylic resin to prepare the anticorrosive paint.
Example 4
(1) Weighing a certain amount of L-histidine (2g) and dispersing in distilled water (100ml), stirring for 1h, heating to 40 ℃, and adding Na2CO3Adjusting the pH value of the system to 7.5; adding ASA absolute ethanol solution with mass fraction of 50% into the system every 30min for 1 time, adding into the system for 4 times, and slowly adding Na2CO3The solution is used for keeping the pH value of the reaction system to be 7.5; after the 4 th addition of the ASA absolute ethanol solution is finished, the pH is adjusted to 7.5, and the Na addition is stopped2CO3Adjusting the pH of the solution until the solution is neutral, extracting the solution by using an ethanol water solution with the mass fraction of 90%, washing and filtering the solution, and finally drying the solution in a drying oven at the temperature of 50 ℃ until the weight of the solution is constant, thus obtaining white solid particles.
(2) 2g of the obtained product is added into 100g of polyurethane resin to prepare the anticorrosive paint.
Example 5
(1) Weighing a certain amount of L-histidine (2g) and dispersing in distilled water (100ml), stirring for 1h, heating to 35 deg.C, and adding Na2CO3Adjusting the pH value of the system to 8.5; adding ASA absolute ethanol solution with mass fraction of 50% into the system every 30min for 1 time, adding into the system for 4 times, and slowly adding Na2CO3The solution is used for keeping the pH value of the reaction system at 8.5; after the 4 th addition of the ASA absolute ethanol solution is finished, the pH is adjusted to 8.5, and the Na addition is stopped2CO3Adjusting the pH of the solution until the solution is neutral, extracting the solution by using an ethanol water solution with the mass fraction of 90%, washing and filtering the solution, and finally drying the solution in a drying oven at the temperature of 50 ℃ until the weight of the solution is constant, thus obtaining white solid particles.
(2) 2g of the obtained product is added into 100g of phenolic resin to prepare the anticorrosive paint.
Example 6
(1) Weighing a certain amount of L-histidine (2g) to be dispersed in distilled water (100ml), stirring for 1h, heating to 36 ℃, and adding Na2CO3Adjusting the pH value of the system to 9; adding 50% ASA absolute ethanol solution into the mixture every 30minAdding the mixture into the system for 4 times, and slowly adding Na2CO3The solution is used for keeping the pH value of the reaction system to be 9; after the 4 th addition of the ASA absolute ethanol solution is finished, the pH is adjusted to 9, and the Na addition is stopped2CO3Adjusting the pH of the solution until the solution is neutral, extracting the solution by using an ethanol water solution with the mass fraction of 90%, washing and filtering the solution, and finally drying the solution in a drying oven at the temperature of 50 ℃ until the weight of the solution is constant, thus obtaining white solid particles.
(2) 2g of the obtained product is added into 100g of epoxy resin to prepare the anticorrosive paint.
Example 7
(1) Weighing a certain amount of L-histidine (2g) and dispersing in distilled water (100ml), stirring for 1h, heating to 39 ℃, and adding Na2CO3Adjusting the pH value of the system to 8.5; adding 50% ASA (4.52g) anhydrous ethanol solution into the system every 30min for 1 time, adding into the system for 4 times, and slowly adding Na2CO3The solution is used for keeping the pH value of the reaction system at 8.5; after the 4 th addition of the ASA absolute ethanol solution is finished, the pH is adjusted to 8.5, and the Na addition is stopped2CO3Adjusting the pH of the solution until the solution is neutral, extracting the solution by using an ethanol water solution with the mass fraction of 90%, washing and filtering the solution, and finally drying the solution in a drying oven at the temperature of 50 ℃ until the weight of the solution is constant, thus obtaining white solid particles.
(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 hydrophobically modified L-histidine corrosion inhibitor, the ASA-modified L-histidine corrosion inhibitor synthesized in example 7 was subjected to nuclear magnetic hydrogen spectroscopy, and the results are shown in fig. 2.
As can be seen from FIG. 2, the present invention successfully prepares a hydrophobically modified L-histidine corrosion inhibitor with a target structure.
TABLE 1
Table 1 shows the results of the slow release rate test of the ASA-modified L-histidine corrosion inhibitor synthesized in example 7 applied to an epoxy resin coating and an epoxy resin coating without the corrosion inhibitor. From the test results: the modified L-histidine corrosion inhibitor prepared by the scheme has high corrosion inhibition rate.
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 (9)
1. A double-hydrophobic-chain modified L-histidine corrosion inhibitor is characterized in that the structural formula of the corrosion inhibitor is as follows:
2. a preparation method of a double-hydrophobic-chain modified L-histidine corrosion inhibitor is characterized by comprising the following steps:
dispersing L-histidine in water, stirring, heating to 35-40 ℃, and adding Na2CO3Adjusting the pH value of the system to be alkalescent;
adding ASA absolute ethyl alcohol solution into the system, and slowly adding Na2CO3The solution is used for keeping the pH value of the reaction system to be alkalescent;
after adding the ASA absolute ethyl alcohol solution, adjusting the pH value to be alkalescent, and stopping adding Na2CO3Adjusting the pH of the solution to be neutral, extracting with an ethanol water solution, washing, performing suction filtration, and finally drying to constant weight to obtain white solid particles.
3. The preparation method of the double hydrophobic chain modified L-histidine corrosion inhibitor according to claim 2, wherein the mass ratio of the L-histidine to the water is 1-5%.
4. The method of claim 2, wherein the weakly basic pH is 7.5 to 9.
5. The method for preparing the double hydrophobic chain modified L-histidine corrosion inhibitor according to claim 2, wherein the ratio of the amount of L-histidine to ASA material is 1: (1-3).
6. The preparation method of the double hydrophobic chain modified L-histidine corrosion inhibitor according to claim 2, wherein the drying temperature is 45-60 ℃.
7. The application of the double-hydrophobic-chain modified L-histidine corrosion inhibitor disclosed in claim 1 in a waterborne self-repairing anticorrosive coating and a hydrophobic matrix coating.
8. The use according to claim 7, wherein the double hydrophobic chain modified L-histidine corrosion inhibitor is added to a matrix resin to form an anticorrosive coating;
the matrix resin is as follows: epoxy resins, alkyd resins, acrylic resins, polyurethane resins or phenolic resins.
9. The use according to claim 8, wherein the double hydrophobic chain modified L-histidine corrosion inhibitor is added in the matrix resin in an amount of: 1 to 5 percent.
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| CN102026931A (en) * | 2009-02-26 | 2011-04-20 | Ppt研究公司 | Corrosion inhibiting compositions |
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| US5531934A (en) * | 1994-09-12 | 1996-07-02 | Rohm & Haas Company | Method of inhibiting corrosion in aqueous systems using poly(amino acids) |
| AU701456B2 (en) * | 1994-09-12 | 1999-01-28 | Rohm And Haas Company | Method of inhibiting sulfate scale in aqueous systems |
| US6559265B2 (en) * | 2000-09-22 | 2003-05-06 | Ppg Industries Ohio, Inc. | Curable polyurethanes, coatings prepared therefrom, and method of making the same |
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