CN116041974A - Preparation process of high-performance modified asphalt containing active compatibilizer - Google Patents
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- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
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- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
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- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Abstract
The invention relates to the technical field of asphalt, and discloses a preparation process of high-performance modified asphalt containing an active compatibilizer, which utilizes 4, 4-diaminodiphenylmethane to react with epichlorohydrin to obtain tetraepoxypropylamine diphenylmethane; and then, as a precursor, performing epoxy esterification reaction with oleic acid, and finally, performing half oxidation with hydrogen peroxide in a formic acid-sulfuric acid system to oxidize a double bond part in an oleic acid structure into an epoxy group, thereby obtaining the four-functionality active compatibilizer, wherein the epoxy group and the epoxy resin are chemically crosslinked with a curing agent in thermocuring, and simultaneously, carbon-carbon double bonds in the active compatibilizer can be crosslinked with double bonds in asphalt, so that the epoxy resin and the asphalt are chemically bonded through the compatibilizer to form a stable chemical crosslinking network, and the obtained epoxy asphalt has better tensile strength, elongation at break and low water absorption.
Description
Technical Field
The invention relates to the technical field of asphalt, in particular to a preparation process of high-performance modified asphalt containing an active compatibilizer.
Background
The epoxy asphalt obtained by chemically modifying the asphalt by using the epoxy resin has better heat resistance, low-temperature cracking resistance, fatigue resistance and other performances, is widely applied to the aspects of road pavement, bridge deck pavement, waterproof materials and the like, and is mainly a black brown complex mixture composed of hydrocarbon compounds with different molecular weights and nonmetallic derivatives thereof, and has poor interfacial compatibility with the epoxy resin, so that the novel compatibilizer is developed in recent years, the interfacial performance of the epoxy resin and the asphalt is improved, and the thermosetting property, the ductility and the mechanical property of the epoxy asphalt are research hot spots.
The epoxy asphalt compatibilizer can be prepared by taking unsaturated fatty acid as a precursor, improving esterification reaction, epoxidation reaction and the like, for example, according to China patent 201310588802.4, namely an epoxy asphalt compatibilizer, a preparation method and a use method thereof, after esterification reaction of unsaturated aliphatic carboxylic acid and polyhydric alcohol, the unsaturated aliphatic carboxylic acid and polyhydric alcohol are subjected to epoxidation by hydrogen peroxide to obtain a novel epoxy asphalt compatibilizer, so that the mechanical strength and stability of an epoxy asphalt material are improved; the invention takes tetraglycinaminodiphenyl methane as a precursor, performs ring-opening esterification reaction with oleic acid, and prepares a novel active compatibilizer through semi-ring oxidation, thereby improving the comprehensive performance of the epoxy asphalt.
Disclosure of Invention
(one) solving the technical problems
The invention provides high-performance modified asphalt containing an active compatibilizer, which solves the problems of poor compatibility of epoxy resin and asphalt and low mechanical strength of epoxy asphalt.
(II) technical scheme
The high-performance modified asphalt containing the active compatibilizer comprises the following components in parts by weight: 100 parts of matrix asphalt, 20-35 parts of epoxy resin, 4-8 parts of tetrafunctional active compatibilizer, 12-22 parts of curing agent and 6-12 parts of compound curing agent.
Preferably, the high-performance modified asphalt is prepared by the following process: heating, stirring and melting matrix asphalt, adding a tetrafunctional active compatibilizer, a curing agent and a compound curing agent, uniformly mixing, adding epoxy resin, pouring the materials into a mold, and carrying out heat preservation and curing for 4-8h at 140-160 ℃ to obtain the high-performance modified asphalt containing the active compatibilizer.
Preferably, the tetrafunctional active compatibilizer is prepared by the following process:
s1: dissolving 4, 4-diaminodiphenyl methane and a catalyst benzyl triethyl ammonium chloride (TEBA) into an ethanol solution, then dropwise adding the ethanol solution containing epoxy chloropropane in a nitrogen atmosphere, heating to 60-80 ℃ for reaction for 4-10 hours, then cooling to 50-60 ℃, dropwise adding an aqueous solution of sodium hydroxide, controlling the pH of the reaction solution, reacting for 6-12 hours, concentrating under reduced pressure after the reaction, washing with deionized water, and adding the crude product into ethanol for recrystallization to obtain tetraepoxypropylamine diphenyl methane;
s2: dissolving tetraglycinaminodiphenyl methane, oleic acid and tetrabutylammonium bromide (TBAB) serving as a catalyst into a dimethylbenzene solvent, heating to 110-130 ℃ for reflux reaction for 6-12h, concentrating under reduced pressure after the reaction, and washing with deionized water and acetone in sequence to obtain a compatibilizer precursor.
S3: dropwise adding formic acid and concentrated sulfuric acid into a compatibilizer precursor in a nitrogen atmosphere at 60-80 ℃, uniformly stirring the mixture, sampling the mixture every 5min to determine an epoxy value, cooling the reaction solution to room temperature when the epoxy value is reduced, adding an aqueous solution of sodium carbonate to adjust the pH to be neutral, filtering the solvent, and washing the solvent with deionized water and acetone in sequence to obtain the four-functionality active compatibilizer.
Preferably, the molar ratio of the 4, 4-diaminodiphenyl methane, the benzyl triethyl ammonium chloride and the epichlorohydrin in the S1 is 1:0.01-0.015:4.2-5.
Preferably, in the step S1, the pH of the reaction solution is controlled to be 13-14.
Preferably, the reaction molar ratio of the S2 tetraglycidoxy-l-diphenyl methane, the oleic acid and the tetrabutylammonium bromide is 1:4-4.8:0.08-0.15.
(III) beneficial technical effects
Using 4, 4-diaminodiphenylmethane and epichlorohydrinAlkyl reaction to obtain tetraepoxypropylamine diphenyl methane; then, the precursor is used as a precursor to perform epoxy esterification reaction with oleic acid, and finally, hydrogen peroxide is subjected to half-oxidation in a formic acid-sulfuric acid system to partially oxidize double bonds in an oleic acid structure into epoxy groups, so that the four-functionality active compatibilizer is obtained, wherein 1473cm of the four-functionality active compatibilizer is obtained in an infrared spectrum -1 The vibration absorption peak of benzene ring skeleton is 1721cm -1 The shrinkage vibration peak of the ester carbonyl C=O is an epoxy group of tetraglycinaminodiphenyl methane, and an ester bond is generated by epoxy esterification reaction between the epoxy group and the carboxyl of oleic acid; 1595cm -1 A vibration absorption peak at double bond c=c; 954cm -1 The shrinkage vibration peak of the epoxy group is shown, and the active compatibilizer is proved to contain a carbon-carbon double bond and the epoxy group.
In the curing reaction process, the epoxy group of the tetrafunctional active compatibilizer and the epoxy resin are chemically crosslinked with the curing agent in the heat curing process, and simultaneously, the carbon-carbon double bond in the active compatibilizer can be crosslinked with the double bond in the asphalt, so that the epoxy resin and the asphalt are chemically bonded through the compatibilizer to form a stable chemical crosslinking network, the interfacial acting force between the epoxy resin and the asphalt is enhanced, the compatibility is improved, the epoxy asphalt maintains the ductility of the asphalt, and meanwhile, the asphalt is endowed with excellent thermosetting property and strength, and the obtained epoxy asphalt has better tensile strength, elongation at break, low water absorption rate and excellent comprehensive performance.
Drawings
FIG. 1 is an infrared spectrum of a tetrafunctional active compatibilizer.
FIG. 2 is a plot of tensile properties and water absorption test for epoxy asphalt.
Detailed Description
Example 1
(1) Dissolving 5mmol of 4, 4-diaminodiphenyl methane and 0.06mmol of catalyst benzyl triethyl ammonium chloride into ethanol solution, then dropwise adding ethanol solution containing 22mmol of epichlorohydrin in nitrogen atmosphere, heating to 80 ℃ for reaction for 4 hours, then cooling to 60 ℃, dropwise adding aqueous solution of sodium hydroxide, controlling the pH of the reaction solution to 14, reacting for 8 hours, concentrating under reduced pressure after the reaction, washing with deionized water, and adding the crude productRecrystallizing in ethanol to obtain tetraepoxypropylamine diphenylmethane; the structure is that
1 H NMR(CDCl 3 ,300MHz)δ:7.36-7.22(m,4H)，7.02-6.85(m,4H)，4.12-3.95(m,2H)，3.46-3.20(m,8H)，2.91-2.80(m,4H)，2.57-2.35(m,8H)。
(2) 2mmol of tetraglycinaminodiphenyl methane, 8mmol of oleic acid and 0.16mmol of catalyst tetrabutylammonium bromide are dissolved in a xylene solvent, the temperature is raised to 110 ℃ for reflux reaction for 12 hours, the reaction is carried out, the decompression concentration is carried out, deionized water and acetone are sequentially used for washing, and a compatibilizer precursor is obtained.
(3) 1.2mL of formic acid and 40uL of concentrated sulfuric acid are dropwise added into 2g of compatibilizer precursor under the nitrogen atmosphere at the temperature of 80 ℃, 8mL of 30% hydrogen peroxide aqueous solution is uniformly stirred, the sample is taken every 5min to determine the epoxy value, the reaction solution is cooled to room temperature when the epoxy value is reduced, then sodium carbonate aqueous solution is added to adjust the pH value to be neutral, the solvent is filtered, and deionized water and acetone are sequentially used for washing, so that the tetrafunctional active compatibilizer is obtained.
(4) Heating, stirring and melting 200g of matrix asphalt, then adding 8g of tetrafunctional active compatibilizer, 30g of curing agent sebacic acid and 15g of compound curing agent methyl tetrahydrophthalic anhydride, uniformly mixing, then adding 40g of epoxy resin, pouring the materials into a mold, and carrying out heat preservation and curing for 8 hours at 140 ℃ to obtain the high-performance modified asphalt containing the active compatibilizer.
Example 2
(1) Dissolving 5mmol of 4, 4-diaminodiphenyl methane and 0.05mmol of catalyst benzyltriethylammonium chloride into an ethanol solution, then dropwise adding an ethanol solution containing 21mmol of epichlorohydrin in a nitrogen atmosphere, heating to 70 ℃ for reaction for 8 hours, then cooling to 60 ℃, dropwise adding an aqueous solution of sodium hydroxide, controlling the pH of the reaction solution to 14, reacting for 8 hours, concentrating under reduced pressure after the reaction, washing with deionized water, and adding the crude product into ethanol for recrystallization to obtain tetraepoxypropylamine diphenyl methane.
(2) 2mmol of tetraglycinaminodiphenyl methane, 8mmol of oleic acid and 0.16mmol of catalyst tetrabutylammonium bromide are dissolved in a xylene solvent, the temperature is raised to 130 ℃ for reflux reaction for 6 hours, the reaction is carried out, the concentration is reduced after the reaction, deionized water and acetone are used for washing in sequence, and a compatibilizer precursor is obtained.
(3) 1.5mL of formic acid and 80uL of concentrated sulfuric acid are dropwise added into 2g of compatibilizer precursor under the nitrogen atmosphere at the temperature of 70 ℃, 10mL of 30% hydrogen peroxide aqueous solution is uniformly stirred, the epoxy value is measured by sampling every 5min, the reaction solution is cooled to room temperature when the epoxy value is reduced, then sodium carbonate aqueous solution is added to adjust the pH value to be neutral, the solvent is filtered, and deionized water and acetone are sequentially used for washing, so that the tetrafunctional active compatibilizer is obtained.
(4) 200g of matrix asphalt is heated, stirred and melted, then 10g of tetrafunctional active compatibilizer, 30g of curing agent sebacic acid and 18g of compound curing agent methyl tetrahydrophthalic anhydride are added, 50g of epoxy resin is added after uniform mixing, the materials are poured into a mold, and the high-performance modified asphalt containing the active compatibilizer is obtained after thermal insulation and curing for 4 hours at 160 ℃.
Example 3
(1) Dissolving 5mmol of 4, 4-diaminodiphenyl methane and 0.075mmol of catalyst benzyltriethylammonium chloride into an ethanol solution, then dropwise adding an ethanol solution containing 25mmol of epichlorohydrin in a nitrogen atmosphere, heating to 60 ℃ for reaction for 8 hours, then cooling to 50 ℃, dropwise adding an aqueous solution of sodium hydroxide, controlling the pH of the reaction solution to 14, reacting for 12 hours, concentrating under reduced pressure after the reaction, washing with deionized water, and adding the crude product into ethanol for recrystallization to obtain tetraepoxypropylamine diphenyl methane.
(2) 2mmol of tetraglycinaminodiphenyl methane, 9.6mmol of oleic acid and 0.3mmol of tetrabutylammonium bromide serving as a catalyst are dissolved in a xylene solvent, the temperature is raised to 130 ℃ for reflux reaction for 6 hours, the reaction is carried out, the concentration is reduced after the reaction, deionized water and acetone are sequentially used for washing, and a compatibilizer precursor is obtained.
(3) 2mL of formic acid and 100uL of concentrated sulfuric acid are dropwise added into 2g of compatibilizer precursor under the nitrogen atmosphere at the temperature of 70 ℃, 12mL of 30% hydrogen peroxide aqueous solution is uniformly stirred, the epoxy value is measured by sampling every 5min, when the epoxy value is reduced, the reaction solution is cooled to room temperature, then sodium carbonate aqueous solution is added to adjust the pH value to be neutral, the solvent is filtered, and deionized water and acetone are sequentially used for washing, so that the tetrafunctional active compatibilizer is obtained.
(4) 200g of matrix asphalt is heated, stirred and melted, then 16g of tetrafunctional active compatibilizer, 44g of curing agent sebacic acid and 24g of compound curing agent methyl tetrahydrophthalic anhydride are added, 70g of epoxy resin is added after uniform mixing, the materials are poured into a mold, and the high-performance modified asphalt containing the active compatibilizer is obtained after thermal insulation and curing for 8 hours at 160 ℃.
Example 4
(1) Dissolving 5mmol of 4, 4-diaminodiphenyl methane and 0.065mmol of catalyst benzyltriethylammonium chloride into an ethanol solution, then dropwise adding an ethanol solution containing 23mmol of epichlorohydrin in a nitrogen atmosphere, heating to 80 ℃ for reaction for 8 hours, then cooling to 60 ℃, dropwise adding an aqueous solution of sodium hydroxide, controlling the pH of the reaction solution to 13, reacting for 12 hours, concentrating under reduced pressure after the reaction, washing with deionized water, and adding the crude product into ethanol for recrystallization to obtain tetraepoxypropylamine diphenyl methane.
(2) 2mmol of tetraglycinaminodiphenyl methane, 9mmol of oleic acid and 0.25mmol of catalyst tetrabutylammonium bromide are dissolved in a xylene solvent, the temperature is raised to 120 ℃ for reflux reaction for 8 hours, the reaction is carried out, the concentration is reduced after the reaction, deionized water and acetone are used for washing in sequence, and a compatibilizer precursor is obtained.
(3) 1.5mL of formic acid and 80uL of concentrated sulfuric acid are dropwise added into 2g of compatibilizer precursor under the nitrogen atmosphere at the temperature of 80 ℃, 10mL of 30% hydrogen peroxide aqueous solution is uniformly stirred, the epoxy value is measured by sampling every 5min, the reaction solution is cooled to room temperature when the epoxy value is reduced, then sodium carbonate aqueous solution is added to adjust the pH value to be neutral, the solvent is filtered, and deionized water and acetone are sequentially used for washing, so that the tetrafunctional active compatibilizer is obtained.
(4) 200g of matrix asphalt is heated, stirred and melted, then 16g of tetrafunctional active compatibilizer, 40g of curing agent sebacic acid and 20g of compound curing agent methyl tetrahydrophthalic anhydride are added, 60g of epoxy resin is added after uniform mixing, the materials are poured into a mold, and the high-performance modified asphalt containing the active compatibilizer is obtained after thermal insulation and curing for 8 hours at 150 ℃.
Comparative example 1
Heating, stirring and melting 200g of matrix asphalt, adding 30g of curing agent sebacic acid and 15g of compound curing agent methyl tetrahydrophthalic anhydride, uniformly mixing, adding 40g of epoxy resin, pouring the materials into a mold, and carrying out heat preservation and curing for 6h at 150 ℃ to obtain the epoxy asphalt.
With reference to the method of ASTM D638-03 standard, the tensile strength and elongation at break of the epoxy asphalt tested by the tensile testing machine are improved, the tensile rate is 100mm/min, the testing temperature is 25 ℃, 5 groups of test samples are tested every other sample, and the average value is obtained.
The water absorption was measured by reference to the method of ASTM D570, test temperature 25℃and water absorption time of 7 days.
Claims (6)
1. A high-performance modified asphalt containing an active compatibilizer is characterized in that: the high-performance modified asphalt comprises the following components in parts by weight: 100 parts of matrix asphalt, 20-35 parts of epoxy resin, 4-8 parts of tetrafunctional active compatibilizer, 12-22 parts of curing agent and 6-12 parts of compound curing agent.
2. A process for preparing a high performance modified asphalt containing an active compatibilizer as defined in claim 1, wherein: the high-performance modified asphalt is prepared by the following process: heating, stirring and melting matrix asphalt, adding a tetrafunctional active compatibilizer, a curing agent and a compound curing agent, uniformly mixing, adding epoxy resin, pouring the materials into a mold, and carrying out heat preservation and curing for 4-8h at 140-160 ℃ to obtain the high-performance modified asphalt containing the active compatibilizer.
3. The process for preparing a high performance modified asphalt containing an active compatibilizer according to claim 2, wherein: the four-functionality active compatibilizer is prepared by the following process:
s1: dissolving 4, 4-diaminodiphenyl methane and a catalyst benzyl triethyl ammonium chloride into an ethanol solution, then dropwise adding the ethanol solution containing epoxy chloropropane in a nitrogen atmosphere, heating to 60-80 ℃ for reaction for 4-10 hours, then cooling to 50-60 ℃, dropwise adding an aqueous solution of sodium hydroxide, controlling the pH of the reaction solution, and reacting for 6-12 hours to obtain tetraepoxypropylamine diphenyl methane;
s2: dissolving tetraglycinaminodiphenyl methane, oleic acid and tetrabutylammonium bromide serving as a catalyst into a xylene solvent, and heating to 110-130 ℃ for reflux reaction for 6-12h to obtain a compatibilizer precursor;
s3: and (3) dropwise adding formic acid and concentrated sulfuric acid into the compatibilizer precursor in a nitrogen atmosphere at 60-80 ℃, uniformly stirring, sampling every 5min to determine an epoxy value, cooling the reaction solution to room temperature when the epoxy value is reduced, and then adding an aqueous solution of sodium carbonate to adjust the pH to be neutral to obtain the tetrafunctional active compatibilizer.
4. A process for the preparation of a high performance modified asphalt containing an active compatibilizer according to claim 3, characterized in that: the molar ratio of the 4, 4-diaminodiphenyl methane, the benzyl triethyl ammonium chloride and the epichlorohydrin in the S1 is 1:0.01-0.015:4.2-5.
5. A process for the preparation of a high performance modified asphalt containing an active compatibilizer according to claim 3, characterized in that: and in the step S1, controlling the pH of the reaction solution to be 13-14.
6. A process for the preparation of a high performance modified asphalt containing an active compatibilizer according to claim 3, characterized in that: the reaction molar ratio of the S2 tetraglycidoxy-l-diphenyl methane, the oleic acid and the tetrabutylammonium bromide is 1:4-4.8:0.08-0.15.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117050541A (en) * | 2023-07-27 | 2023-11-14 | 山东百成新材料科技股份有限公司 | High-temperature-resistant composite modified asphalt for highway and preparation method thereof |
| CN117050541B (en) * | 2023-07-27 | 2024-05-28 | 山东百成新材料科技股份有限公司 | High-temperature-resistant composite modified asphalt for highway and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117050541A (en) * | 2023-07-27 | 2023-11-14 | 山东百成新材料科技股份有限公司 | High-temperature-resistant composite modified asphalt for highway and preparation method thereof |
| CN117050541B (en) * | 2023-07-27 | 2024-05-28 | 山东百成新材料科技股份有限公司 | High-temperature-resistant composite modified asphalt for highway and preparation method thereof |
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