CN112759697A - Methacrylic resin and preparation method thereof - Google Patents
Methacrylic resin and preparation method thereof Download PDFInfo
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- CN112759697A CN112759697A CN202011591160.XA CN202011591160A CN112759697A CN 112759697 A CN112759697 A CN 112759697A CN 202011591160 A CN202011591160 A CN 202011591160A CN 112759697 A CN112759697 A CN 112759697A
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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
- C08F220/14—Methyl esters, e.g. methyl (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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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Abstract
The invention provides a preparation method of methacrylic resin, which comprises the following steps: dissolving methyl methacrylate, butyl acrylate and 2-methyl-2-adamantyl methacrylate in ethyl acetate, and adding an initiator to form a mixed solution; introducing protective gas at a preset temperature; placing the mixed solution under the microwave condition for polymerization reaction; wherein the microwave power under the microwave condition is 100-480W, and the addition amount of the initiator is 1-10% of the sum of the mass of the methyl methacrylate, the butyl acrylate and the 2-methyl-2-adamantyl methacrylate. The invention also provides a methacrylic resin. According to the scheme, the microwave heating technology is combined with different adding proportions of the initiator, so that the monomers are decomposed to generate free radicals with different concentrations, the mutual polymerization degree of the free radicals is different, the methacrylic resins with different molecular weights are polymerized, the molecular weight of the product is controlled, the reaction speed is increased, and the synthesis efficiency is greatly improved.
Description
Technical Field
The invention belongs to the technical field of chemistry, and particularly relates to methacrylic resin and a preparation method thereof.
Background
Photoresist is a photosensitive material and is a key processing material in the fine processing technology of integrated circuits. The methacrylic resin is used as a part of photoresist composition, determines the quality of the photoresist performance, and is a hotspot of current photoresist material research.
In order to meet the performance requirements of the photoresist, methacrylic resins with different molecular weights are prepared, and the molecular weight of the methacrylic resin is controlled by adding an initiator into an emulsion or a solution, heating and refluxing through a water bath or an oil bath, and performing free radical polymerization. However, this method has a disadvantage that the polymerization time is long and the efficiency is low because the final product can be obtained after a long period of polymerization reaction in a solution or emulsion, and sometimes the polymerization time is 20 hours or more to achieve a good polymerization degree.
Disclosure of Invention
The embodiment of the invention provides a preparation method of methacrylic resin, aiming at solving the defects of overlong reaction time, low efficiency and the like of the traditional preparation method.
The embodiment of the invention is realized in such a way that the preparation method of the methacrylic resin comprises the following steps:
dissolving methyl methacrylate, butyl acrylate and 2-methyl-2-adamantyl methacrylate in ethyl acetate, and adding an initiator to form a mixed solution;
introducing protective gas at a preset temperature;
placing the mixed solution under the microwave condition for polymerization reaction;
wherein the microwave power under the microwave condition is 100-480W, and the preset temperature is 25-50 ℃.
In addition, the invention also provides methacrylic resin, which is prepared by the preparation method.
In addition, the invention also provides a photoresist which comprises the methacrylic resin prepared by the preparation method.
The preparation method of the methacrylic resin comprises the steps of introducing protective gas into a mixed solution obtained by mixing monomers (methyl methacrylate, butyl acrylate and 2-methyl-2-adamantyl methacrylate) and an initiator, and then carrying out polymerization reaction under the microwave condition. The microwave heating device has the advantages that the microwave heating device can generate deep heating effect on irradiated substances through strong penetrating power of microwaves, and therefore, the microwave heating device has the characteristics of high speed, good uniformity, no hysteresis and the like. In the scheme, the microwave heating technology is combined with different addition proportions of the initiator, so that the monomers are decomposed to generate free radicals with different concentrations, and the mutual polymerization degrees of the free radicals are different, thereby polymerizing the methacrylic resins with different molecular weights, accelerating the reaction speed and greatly improving the synthesis efficiency while controlling the molecular weight of the product.
Drawings
FIG. 1 is a flow chart of a method for preparing a methacrylic resin according to an embodiment of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
As shown in fig. 1, an embodiment of the present invention provides a method for preparing a methacrylic resin. The preparation method of the methacrylic resin comprises the following steps:
step S10, dissolving methyl methacrylate, butyl acrylate and 2-methyl-2-adamantyl methacrylate in ethyl acetate, and adding an initiator to form a mixed solution;
step S20, introducing protective gas at a preset temperature;
step S30, placing the mixed solution under microwave condition for polymerization reaction;
wherein the microwave power under the microwave condition is 100-480W, and the addition amount of the initiator is 1-10% of the sum of the mass of the methyl methacrylate, the butyl acrylate and the 2-methyl-2-adamantyl methacrylate.
The mixed solution is placed in a microwave environment for polymerization reaction, and the mixed solution is heated deeply by the strong penetrating power of microwaves. By utilizing the high-quality characteristics of high heating speed, good uniformity, no hysteresis and the like of microwave radiation, the microwave technology is introduced into the preparation process of the methacrylic resin, so that the resin synthesis efficiency can be greatly improved.
In addition, initiators with different proportions can be introduced, heating is carried out by introducing different microwave powers, free radicals with different concentrations are generated by decomposition, and free radicals are generated by combining monomers to carry out free radical polymerization so as to control the polymerization degree of the monomers and control the molecular weight. For example, the amount of the initiator added may be 1 to 10% of the sum of the mass of the methyl methacrylate, butyl acrylate and 2-methyl-2-adamantyl methacrylate.
In another embodiment, the microwave power under microwave conditions is 100-250W, and the addition amount of the initiator is 1-5% of the sum of the mass of the methyl methacrylate, the butyl acrylate and the 2-methyl-2-adamantyl methacrylate. In another embodiment, the microwave power under microwave conditions is 250W, and the initiator is added in an amount of 3% of the sum of the mass of the methyl methacrylate, butyl acrylate and 2-methyl-2-adamantyl methacrylate.
In step S10, methyl methacrylate, butyl acrylate, and 2-methyl-2-adamantyl methacrylate are added to a reaction vessel containing ethyl acetate, and after mixing uniformly, an initiator is added, and stirring is performed, and the initiator and the monomers are mixed uniformly to form a mixed solution. Wherein the proportion of the methyl methacrylate, the butyl acrylate and the 2-methyl-2-adamantyl methacrylate is as follows: (1-10) methyl methacrylate, (1-10) butyl acrylate and (1-10) 2-methyl-2-adamantyl methacrylate. The mixing unit is other measurement units such as mass or molar mass. The usage amount of the ethyl acetate is 2-10 times of the total mass of the monomers, and the usage amount of the initiator is 1-10% of the total mass of the monomers.
In step S20, the method of introducing the protective gas specifically includes placing the reaction vessel with the mixed solution in a constant temperature water bath at 30 ℃, slowly introducing nitrogen gas into the reaction vessel for 30min, and removing oxygen in the reaction vessel, thereby performing nitrogen protection on the reaction system.
Since the methacrylic resin is viscous and colloidal in the solution, the determination conditions for determining whether or not the polymerization reaction is completed in step S30 are as follows: viscous colloids are generated in the mixed solution, and the amount of the viscous colloids is not increased any more. If the current reaction solution meets the judgment condition, finishing the polymerization reaction; and if the current reaction solution does not meet the judgment condition, continuing the reaction.
In another embodiment, after the polymerization reaction is finished, the reaction solution of the polymerization reaction is subjected to purification treatment of the target product. Specifically, the reaction solution is dried overnight at 50-85 ℃, and excessive solvent in the reaction solution is removed; grinding the dried solid, completely dissolving in tetrahydrofuran, adding precipitant, and purifying; and after precipitation and purification, centrifuging the formed suspension, carrying out solid-liquid separation, taking the solid, placing the solid in a vacuum oven, and drying at 50-85 ℃ overnight. Because the molecular weight distribution of the polymer obtained by microwave-assisted polymerization is narrow, the small-chain polymer in the reaction system is less, and a large amount of solvent is not needed for washing when the precipitant is purified.
In one embodiment, the precipitant is n-hexane, and the amount of the precipitant is 4 times of the mass of the reaction solution. The temperature for overnight drying in the vacuum oven is preferably 80 ℃. The centrifugation speed is 5000rpm, and the centrifugation time is 5-10 min.
The following examples illustrate the preparation of methacrylic resins according to embodiments of the present invention.
Example one
The invention provides a method for regulating and controlling the molecular weight of methacrylic resin by a microwave method, which comprises the following steps:
(1) 50g of methyl methacrylate, 30g of butyl acrylate and 20g of 2-methyl-2-adamantyl methacrylate were put in a four-necked flask containing 300g of ethyl acetate, and stirred until the monomers were dissolved;
(2) after the monomers are dissolved, adding a main initiator (dimethyl azodiisobutyrate), and stirring until the main initiator is dissolved, wherein the use amount of the main initiator is 1 g;
(3) placing the single-neck flask in a constant-temperature water bath kettle at 30 ℃, slowly introducing nitrogen for 30min, and discharging oxygen in the flask;
(4) placing the four-mouth flask in a microwave oven, wherein the power is 250W, and carrying out microwave heating for polymerization reaction;
(5) stopping the reaction after the product in the flask polymerizes into a viscous colloid;
(6) putting the product in a vacuum oven, and drying at 80 ℃ overnight;
(7) crushing the dried product, dissolving the crushed product in a certain amount of tetrahydrofuran, and stirring until the tetrahydrofuran is dissolved to be clear, wherein the using amount of the tetrahydrofuran is 3 times that of the product;
(8) pouring the solution into a certain amount of n-hexane for precipitation and purification treatment, wherein the usage amount of the n-hexane is 3 times of that of the solution;
(9) centrifuging for solid-liquid separation, placing the solid in a vacuum oven, and drying at 80 deg.C overnight;
(10) the dried product was weighed to calculate the yield, the molecular weight and the molecular weight distribution, and the results are shown in Table I.
Example two
The invention provides a method for regulating and controlling the molecular weight of methacrylic resin by a microwave method, which comprises the following steps:
(1) 50g of methyl methacrylate, 30g of butyl acrylate and 20g of 2-methyl-2-adamantyl methacrylate were put in a four-necked flask containing 300g of ethyl acetate, and stirred until the monomers were dissolved;
(2) after the monomers are dissolved, adding a main initiator (dimethyl azodiisobutyrate), and stirring until the main initiator is dissolved, wherein the use amount of the main initiator is 1 g;
(3) placing the single-neck flask in a constant-temperature water bath kettle at 30 ℃, slowly introducing nitrogen for 30min, and discharging oxygen in the flask;
(4) placing the four-mouth flask in a microwave oven with the power of 100W, and carrying out microwave heating for polymerization reaction;
(5) stopping the reaction after the product in the flask polymerizes into a viscous colloid;
(6) putting the product in a vacuum oven, and drying at 80 ℃ overnight;
(7) crushing the dried product, dissolving the crushed product in a certain amount of tetrahydrofuran, and stirring until the tetrahydrofuran is dissolved to be clear, wherein the using amount of the tetrahydrofuran is 3 times that of the product;
(8) pouring the solution into a certain amount of n-hexane for precipitation and purification treatment, wherein the usage amount of the n-hexane is 3 times of that of the solution;
(9) centrifuging for solid-liquid separation, placing the solid in a vacuum oven, and drying at 80 deg.C overnight;
(10) the dried product was weighed to calculate the yield, the molecular weight and the molecular weight distribution, and the results are shown in Table I.
EXAMPLE III
The invention provides a method for regulating and controlling the molecular weight of methacrylic resin by a microwave method, which comprises the following steps:
(1) 50g of methyl methacrylate, 30g of butyl acrylate and 20g of 2-methyl-2-adamantyl methacrylate were put in a four-necked flask containing 300g of ethyl acetate, and stirred until the monomers were dissolved;
(2) after the monomers are dissolved, adding a main initiator (dimethyl azodiisobutyrate), and stirring until the main initiator is dissolved, wherein the use amount of the main initiator is 1 g;
(3) placing the single-neck flask in a constant-temperature water bath kettle at 30 ℃, slowly introducing nitrogen for 30min, and discharging oxygen in the flask;
(4) placing the four-mouth flask in a microwave oven with the power of 480W, and carrying out microwave heating for polymerization reaction;
(5) stopping the reaction after the product in the flask polymerizes into a viscous colloid;
(6) putting the product in a vacuum oven, and drying at 80 ℃ overnight;
(7) crushing the dried product, dissolving the crushed product in a certain amount of tetrahydrofuran, and stirring until the tetrahydrofuran is dissolved to be clear, wherein the using amount of the tetrahydrofuran is 3 times that of the product;
(8) pouring the solution into a certain amount of n-hexane for precipitation and purification treatment, wherein the usage amount of the n-hexane is 3 times of that of the solution;
(9) centrifuging for solid-liquid separation, placing the solid in a vacuum oven, and drying at 80 deg.C overnight;
(10) the dried product was weighed to calculate the yield, the molecular weight and the molecular weight distribution, and the results are shown in Table I.
Example four
The invention provides a method for regulating and controlling the molecular weight of methacrylic resin by a microwave method, which comprises the following steps:
(1) 50g of methyl methacrylate, 30g of butyl acrylate and 20g of 2-methyl-2-adamantyl methacrylate were put in a four-necked flask containing 300g of ethyl acetate, and stirred until the monomers were dissolved;
(2) after the monomers are dissolved, adding a main initiator (dimethyl azodiisobutyrate), and stirring until the main initiator is dissolved, wherein the use amount of the main initiator is 3 g;
(3) placing the single-neck flask in a constant-temperature water bath kettle at 30 ℃, slowly introducing nitrogen for 30min, and discharging oxygen in the flask;
(4) placing the four-mouth flask in a microwave oven, wherein the power is 250W, and carrying out microwave heating for polymerization reaction;
(5) stopping the reaction after the product in the flask polymerizes into a viscous colloid;
(6) putting the product in a vacuum oven, and drying at 80 ℃ overnight;
(7) crushing the dried product, dissolving the crushed product in a certain amount of tetrahydrofuran, and stirring until the tetrahydrofuran is dissolved to be clear, wherein the using amount of the tetrahydrofuran is 3 times that of the product;
(8) pouring the solution into a certain amount of n-hexane for precipitation and purification treatment, wherein the usage amount of the n-hexane is 3 times of that of the solution;
(9) centrifuging for solid-liquid separation, placing the solid in a vacuum oven, and drying at 80 deg.C overnight;
(10) the dried product was weighed to calculate the yield, the molecular weight and the molecular weight distribution, and the results are shown in Table I.
EXAMPLE five
The invention provides a method for regulating and controlling the molecular weight of methacrylic resin by a microwave method, which comprises the following steps:
(1) 50g of methyl methacrylate, 30g of butyl acrylate and 20g of 2-methyl-2-adamantyl methacrylate were put in a four-necked flask containing 300g of ethyl acetate, and stirred until the monomers were dissolved;
(2) after the monomers are dissolved, adding a main initiator (dimethyl azodiisobutyrate), and stirring until the main initiator is dissolved, wherein the use amount of the main initiator is 5 g;
(3) placing the single-neck flask in a constant-temperature water bath kettle at 30 ℃, slowly introducing nitrogen for 30min, and discharging oxygen in the flask;
(4) placing the four-mouth flask in a microwave oven, wherein the power is 250W, and carrying out microwave heating for polymerization reaction;
(5) stopping the reaction after the product in the flask polymerizes into a viscous colloid;
(6) putting the product in a vacuum oven, and drying at 80 ℃ overnight;
(7) crushing the dried product, dissolving the crushed product in a certain amount of tetrahydrofuran, and stirring until the tetrahydrofuran is dissolved to be clear, wherein the using amount of the tetrahydrofuran is 3 times that of the product;
(8) pouring the solution into a certain amount of n-hexane for precipitation and purification treatment, wherein the usage amount of the n-hexane is 3 times of that of the solution;
(9) centrifuging for solid-liquid separation, placing the solid in a vacuum oven, and drying at 80 deg.C overnight;
(10) the dried product was weighed to calculate the yield, the molecular weight and the molecular weight distribution, and the results are shown in Table I.
Table one:
from the results, it can be seen that the use of the microwave method to promote the polymerization of the methacrylic resin has certain feasibility, and different microwave intensities and initiator concentrations can obtain polymers with different molecular weights and have certain regularity. For example, the initiator is used in a large amount, the polymerization time is short, the molecular weight of the polymer is low, and the molecular weight distribution is wide because the high concentration of the initiator generates high concentration of free radicals, which results in the enhancement of the chain termination rate and the short chain. The reaction with high microwave intensity, short polymerization time, low molecular weight and wide molecular weight distribution because the microwave with high intensity provides more heat energy to accelerate the decomposition of the initiator, so that the concentration of free radicals is high and the chain termination rate is enhanced. Of course, more importantly, the microwave method is used for the polymerization of the photoresist main body resin, and the polymerization time can be greatly reduced due to high efficiency. Therefore, the microwave method has certain research prospect in the introduction of photoresist resin polymerization.
The invention has the beneficial effect that the free radical polymerization reaction is carried out under microwave irradiation in the free radical reaction process. Firstly, the characteristics of strong penetrating power of microwave, high speed, good uniformity, no hysteresis and the like are considered as a cleaning technology, and secondly, the polymerization degree of the monomers can be controlled by changing different microwave intensities and initiation introduction amounts, so that the aim of controlling the molecular weight of the polymer is fulfilled.
Further, the invention also provides a methacrylic resin, and the methacrylic resin is prepared by the preparation method of the embodiment. The methacrylic resin with different molecular weights is obtained by controlling polymerization conditions such as different ultrasonic powers, polymerization temperatures, polymerization durations and the like.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (9)
1. A method for preparing a methacrylic resin, comprising the steps of:
dissolving methyl methacrylate, butyl acrylate and 2-methyl-2-adamantyl methacrylate in ethyl acetate, and adding an initiator to form a mixed solution;
introducing protective gas at a preset temperature;
placing the mixed solution under the microwave condition for polymerization reaction;
wherein the microwave power under the microwave condition is 100-480W, and the addition amount of the initiator is 1-10% of the sum of the mass of the methyl methacrylate, the butyl acrylate and the 2-methyl-2-adamantyl methacrylate.
2. The method as claimed in claim 1, wherein the microwave power under microwave condition is 100-250W, and the amount of the initiator is 1-5% of the sum of the mass of the methyl methacrylate, butyl acrylate and 2-methyl-2-adamantyl methacrylate.
3. The method of claim 1, wherein the microwave power under the microwave condition is 250W, and the amount of the initiator is 3% of the total mass of the methyl methacrylate, butyl acrylate and 2-methyl-2-adamantyl methacrylate.
4. The method of any of claims 1 to 5, wherein the initiator is dimethyl azobisisobutyrate.
5. The method of producing a methacrylic resin according to any of claims 1 to 3, wherein the ratio of the methyl methacrylate, butyl acrylate and 2-methyl-2-adamantyl methacrylate is (1 to 10): (1-10): (1-10).
6. The method for producing the acryl resin as claimed in any of claims 1 to 3, wherein the polymerization is terminated after a viscous colloid is generated in the mixed solution.
7. The method of claim 6, wherein after the polymerization reaction is completed, the method further comprises:
and (3) purifying the reaction liquid after the polymerization reaction by using a target product.
8. The method of claim 6, wherein the step of purifying the reaction solution after the polymerization reaction to obtain the target product comprises:
drying the reaction solution at 50-85 ℃ overnight;
grinding the dried solid and completely dissolving the solid in tetrahydrofuran;
adding n-hexane, and performing precipitation purification treatment;
centrifuging the suspension after precipitation and purification, separating solid from liquid, placing the solid in a vacuum oven, and drying at 50-85 ℃ overnight.
9. A methacrylic resin obtained by the production method according to any one of claims 1 to 8.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113861332A (en) * | 2021-09-30 | 2021-12-31 | 宁波南大光电材料有限公司 | Photoresist resin and polymerization method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105199044A (en) * | 2015-11-11 | 2015-12-30 | 重庆城市管理职业学院 | Method for preparing cationic polyacrylamide employing microwave-induced template polymerization |
| CN109942845A (en) * | 2019-02-22 | 2019-06-28 | 江苏南大光电材料股份有限公司 | A kind of preparation method of photoetching gum resin |
| CN111718439A (en) * | 2020-06-19 | 2020-09-29 | 宁波南大光电材料有限公司 | Methacrylic resin and preparation method and application thereof |
-
2020
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105199044A (en) * | 2015-11-11 | 2015-12-30 | 重庆城市管理职业学院 | Method for preparing cationic polyacrylamide employing microwave-induced template polymerization |
| CN109942845A (en) * | 2019-02-22 | 2019-06-28 | 江苏南大光电材料股份有限公司 | A kind of preparation method of photoetching gum resin |
| CN111718439A (en) * | 2020-06-19 | 2020-09-29 | 宁波南大光电材料有限公司 | Methacrylic resin and preparation method and application thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113861332A (en) * | 2021-09-30 | 2021-12-31 | 宁波南大光电材料有限公司 | Photoresist resin and polymerization method thereof |
| CN113861332B (en) * | 2021-09-30 | 2023-02-24 | 宁波南大光电材料有限公司 | Photoresist resin and polymerization method thereof |
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