CN108276789B - Preparation method of self-repairing thermosetting polyurethane asphalt - Google Patents
Preparation method of self-repairing thermosetting polyurethane asphalt Download PDFInfo
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- CN108276789B CN108276789B CN201810131557.7A CN201810131557A CN108276789B CN 108276789 B CN108276789 B CN 108276789B CN 201810131557 A CN201810131557 A CN 201810131557A CN 108276789 B CN108276789 B CN 108276789B
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- Prior art keywords
- asphalt
- self
- repairing
- thermosetting
- thermosetting polyurethane
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- Expired - Fee Related
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- 239000010426 asphalt Substances 0.000 title claims abstract description 57
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 34
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 20
- 239000004814 polyurethane Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 3
- 239000003208 petroleum Substances 0.000 claims description 11
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 5
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 5
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 4
- 229920000053 polysorbate 80 Polymers 0.000 claims description 4
- 229940075579 propyl gallate Drugs 0.000 claims description 4
- 235000010388 propyl gallate Nutrition 0.000 claims description 4
- 239000000473 propyl gallate Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims 1
- 235000013824 polyphenols Nutrition 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 6
- -1 polyphenol compound Chemical class 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 4
- 238000012423 maintenance Methods 0.000 abstract description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000012958 reprocessing Methods 0.000 abstract description 2
- 150000005846 sugar alcohols Polymers 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229950011392 sorbitan stearate Drugs 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000011301 petroleum pitch Substances 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- RMTXUPIIESNLPW-UHFFFAOYSA-N 1,2-dihydroxy-3-(pentadeca-8,11-dienyl)benzene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1O RMTXUPIIESNLPW-UHFFFAOYSA-N 0.000 description 2
- QARRXYBJLBIVAK-UEMSJJPVSA-N 3-[(8e,11e)-pentadeca-8,11-dienyl]benzene-1,2-diol;3-[(8e,11e)-pentadeca-8,11,14-trienyl]benzene-1,2-diol;3-[(8e,11e,13e)-pentadeca-8,11,13-trienyl]benzene-1,2-diol;3-[(e)-pentadec-8-enyl]benzene-1,2-diol;3-pentadecylbenzene-1,2-diol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1O.CCCCCC\C=C\CCCCCCCC1=CC=CC(O)=C1O.CCC\C=C\C\C=C\CCCCCCCC1=CC=CC(O)=C1O.C\C=C\C=C\C\C=C\CCCCCCCC1=CC=CC(O)=C1O.OC1=CC=CC(CCCCCCC\C=C\C\C=C\CC=C)=C1O QARRXYBJLBIVAK-UEMSJJPVSA-N 0.000 description 2
- IYROWZYPEIMDDN-UHFFFAOYSA-N 3-n-pentadec-8,11,13-trienyl catechol Natural products CC=CC=CCC=CCCCCCCCC1=CC=CC(O)=C1O IYROWZYPEIMDDN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- DQTMTQZSOJMZSF-UHFFFAOYSA-N urushiol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1O DQTMTQZSOJMZSF-UHFFFAOYSA-N 0.000 description 2
- 206010039203 Road traffic accident Diseases 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Civil Engineering (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The preparation method of the self-repairing thermosetting polyurethane asphalt is characterized by comprising the following steps: the self-repairing thermosetting polyurethane asphalt is prepared by uniformly blending and stirring a polyphenol compound, a compound containing a plurality of isocyanic acid radicals, a compatilizer, a catalyst and asphalt at 25-120 ℃, and curing at 80-160 ℃ for 12-16 hours. The invention adopts the compound containing phenolic hydroxyl to replace polyhydric alcohol to synthesize the thermosetting polyurethane asphalt, and the novel thermosetting asphalt can recover the original shape under a certain temperature condition after being damaged, and has the self-repairing and reprocessing functions. The method is expected to solve the problem that the thermosetting asphalt material is not easy to recover and maintain, and can save a large amount of resources and maintenance cost.
Description
Technical Field
The invention relates to a preparation method of self-repairing polyurethane resin asphalt, in particular to a preparation method of self-repairing thermosetting polyurethane resin asphalt.
Background
The petroleum asphalt is a petrochemical byproduct, has low price and is mainly used in the field of road pavement. However, in both the asphalt with high penetration and the asphalt with low penetration, the asphalt has the problems that the asphalt melts at high temperature and is likely to crack due to low intermolecular cohesive energy because the molecular weight is not high enough. If the asphalt is not modified and is directly used for paving roads, the paved roads can be melted and flow at high temperature in summer and become brittle and crazed at low temperature in winter, so that the poor road quality needs to be maintained continuously, and the traffic convenience is seriously influenced. At present, in order to solve this problem, the research on modifying thermoplastic petroleum asphalt into thermosetting asphalt materials is very much, and most of the research is thermosetting epoxy asphalt. The thermosetting epoxy asphalt is prepared by mixing epoxy resin, a curing agent, a compatilizer and petroleum asphalt together, and a continuous phase formed by the epoxy resin/the curing agent wraps a dispersed phase formed by the petroleum asphalt under the action of the compatilizer, so that the petroleum asphalt is wrapped and fixed by a thermosetting network structure formed after the epoxy resin is cured, the performance of the thermosetting asphalt is apparent, and the defects of high-temperature melting and low-temperature brittle fracture of common asphalt are overcome. The thermosetting asphalt is not melted any more, the mechanical property is greatly improved, good elasticity and low-temperature performance are shown, and the quality of paved roads is greatly improved. Polyurethane asphalt is also widely used. The thermosetting polyurethane asphalt can be obtained by blending the polyol, the isocyanate and the asphalt under the action of the compatilizer, has excellent elasticity and good waterproofness, and can be used for building waterproof coatings. However, the better material may still be damaged. The road surface paved by the thermosetting epoxy asphalt material and the polyurethane asphalt material needs to be eradicated after being damaged due to traffic accidents, rolling of high-load vehicles, natural aging or extreme climate, and the like. Moreover, because the epoxy resin and the curing reaction are irreversible, and the urethane groups formed by isocyanate and polyol are relatively stable, the removed pavement paving waste is thermosetting and is greatly different from common petroleum asphalt materials, so that the pavement paving waste cannot be melted at high temperature for reshaping, and only can be discarded as construction waste, a large amount of solid waste which is extremely difficult to treat is generated, and a large amount of resources are wasted. This causes great difficulty in road surface maintenance.
Disclosure of Invention
The technical problem to be solved is as follows: the invention provides a preparation method of self-repairing thermosetting polyurethane asphalt aiming at the problem that thermosetting resin asphalt can not be repaired and recycled, the asphalt prepared by the method not only preserves the mechanical property of thermosetting asphalt, but also has the self-repairing characteristic of thermosetting asphalt, and a large amount of resources and cost are saved.
The technical scheme is as follows: the preparation method of the self-repairing thermosetting polyurethane asphalt comprises the steps of blending and stirring a polyphenol compound, a compound containing multiple isocyanate groups, a compatilizer, a catalyst and asphalt uniformly at 25-120 ℃, wherein the molar ratio of phenolic hydroxyl groups to the isocyanate groups is (0.8-1.5) to 1, the compatilizer accounts for 5% of the total mass of a mixture, the catalyst accounts for 0.5% of the total mass of the mixture, the total mass ratio of the polyphenol compound and the compound containing multiple isocyanate groups to the asphalt is 1:1, and curing is carried out at 80-160 ℃ for 12-16 hours to obtain the self-repairing thermosetting polyurethane asphalt.
The polyphenol compound is a compound with at least 2 phenolic hydroxyl groups on the same benzene ring, or has the following structure:
The polyphenol compound is propyl gallate, urushiol or benzenediol.
The molecular structural general formula of the compound containing multiple isocyanate groups is as follows:
The compound containing a plurality of isocyanic acid radicals is polytetrahydrofuran diol prepolymer or toluene diisocyanate.
The compatilizer is tween 80 or sorbitan stearate.
The catalyst was dibutyltin dilaurate.
The asphalt is petroleum asphalt or coal asphalt.
The self-repairing occurs based on the reversible reaction mechanism between phenolic hydroxyl and isocyanate to cause the covalent bond recombination of the thermosetting polyurethane, thereby realizing the self-repairing of the thermosetting polyurethane:
has the advantages that: the invention adopts the compound containing phenolic hydroxyl to replace polyhydric alcohol to synthesize the thermosetting polyurethane asphalt, and the novel thermosetting asphalt can recover the original shape under a certain temperature condition after being damaged, and has the self-repairing and reprocessing functions. The method is expected to solve the problem that the thermosetting asphalt material is not easy to recover and maintain, and can save a large amount of resources and maintenance cost.
Detailed Description
The following examples further illustrate the present invention but are not to be construed as limiting the invention. Modifications and substitutions to methods, procedures, or conditions of the invention may be made without departing from the spirit and substance of the invention.
Unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art.
Reagent: propyl gallate (alatin reagent, chemical purity), petroleum pitch # 90 (tombstone), petroleum pitch # 100 (tombstone), petroleum pitch # 110 (tombstone), polytetrahydrofuran diol polyurethane prepolymer (NCO content 6.2%), toluene diisocyanate (alatin reagent, chemical purity), tween 80 (alatin reagent, chemical purity), sorbitan stearate (alatin reagent, chemical purity), dibutyltin dilaurate (alatin reagent, chemical purity).
Example 1
15.7g of propyl gallate, 12.4g of Tween 80, 108g of polytetrahydrofuran diol polyurethane prepolymer (NCO content: 6.2%), 1.3g of dibutyltin dilaurate and 123g of petroleum asphalt No. 90 are heated to 100 ℃ and 120 ℃, mixed and stirred uniformly, and cured for 12-16 hours at 80-160 ℃. Obtaining the self-repairing thermosetting polyurethane asphalt material.
Example 2
182.6g of urushiol, 29.1g of sorbitan stearate, 108g of toluene diisocyanate, 3g of dibutyltin dilaurate and 290.6g of petroleum asphalt No. 100 are heated to 100 ℃ and 120 ℃, mixed and stirred uniformly, and cured for 12-16 hours at 80-160 ℃. Obtaining the self-repairing thermosetting polyurethane asphalt material.
Example 3
13.14g of hydroquinone, 12.1g of sorbitan stearate, 108g of polytetrahydrofuran diol polyurethane prepolymer (NCO content: 6.2%), 1.3g of dibutyltin dilaurate and 121.1g of petroleum asphalt 110# are heated to 100 ℃ and 120 ℃ to be uniformly mixed and stirred, and cured for 12-16 hours at 80-160 ℃. Obtaining the self-repairing thermosetting polyurethane asphalt material.
Example 4
The self-repairing thermosetting polyurethane asphalt materials prepared in examples 1-3 were subjected to tensile strength tests on a New Satsu CMT4303 universal tester according to GB/T528-. Stretching speed 500mm min-1The sample size was 20mm × 4mm × 2mm, and 5 replicates of each sample were tested and averaged. And (3) tightly butting the fracture surfaces of the sample strips subjected to the tensile test, putting the sample strips into an oven, baking the sample strips at 120 ℃ for 12 hours, and performing the tensile test by the same method again. The results of the two experiments are shown in the following table: example 2 works best.
Claims (1)
1. The preparation method of the self-repairing thermosetting polyurethane asphalt is characterized by comprising the following steps: heating 15.7g of propyl gallate, 12.4g of Tween 80, 108g of polytetrahydrofuran diol polyurethane prepolymer with NCO content of 6.2%, 1.3g of dibutyltin dilaurate and 123g of petroleum asphalt No. 90 to 100 ℃, blending and stirring uniformly, and curing at 80-160 ℃ for 12-16 hours to obtain the self-repairing thermosetting polyurethane asphalt material.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2018100019947 | 2018-01-02 | ||
| CN201810001994 | 2018-01-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108276789A CN108276789A (en) | 2018-07-13 |
| CN108276789B true CN108276789B (en) | 2021-03-23 |
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ID=62808159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810131557.7A Expired - Fee Related CN108276789B (en) | 2018-01-02 | 2018-02-09 | Preparation method of self-repairing thermosetting polyurethane asphalt |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108276789B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114316613A (en) * | 2021-12-16 | 2022-04-12 | 同济大学 | Bi-component thermosetting polyurethane modified asphalt with adjustable retention time and preparation thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5311953A (en) * | 1976-07-20 | 1978-02-02 | Asahi Denka Kogyo Kk | Method for filling joints |
| CN103232717A (en) * | 2013-05-15 | 2013-08-07 | 重庆市智翔铺道技术工程有限公司 | Composite modified asphalt and preparation method thereof |
| CN106632942A (en) * | 2016-09-30 | 2017-05-10 | 中国林业科学研究院林产化学工业研究所 | Self-repairing thermosetting polyurethane and preparation method thereof |
-
2018
- 2018-02-09 CN CN201810131557.7A patent/CN108276789B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5311953A (en) * | 1976-07-20 | 1978-02-02 | Asahi Denka Kogyo Kk | Method for filling joints |
| CN103232717A (en) * | 2013-05-15 | 2013-08-07 | 重庆市智翔铺道技术工程有限公司 | Composite modified asphalt and preparation method thereof |
| CN106632942A (en) * | 2016-09-30 | 2017-05-10 | 中国林业科学研究院林产化学工业研究所 | Self-repairing thermosetting polyurethane and preparation method thereof |
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| Publication number | Publication date |
|---|---|
| CN108276789A (en) | 2018-07-13 |
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Effective date of registration: 20221116 Address after: 210000 Gonglou District, Nanjing City, Jiangsu Province, No. 288, New Village for Workers and Peasants Patentee after: Nanjing Linke Zhongyue new material technology development Co.,Ltd. Address before: No. 16, No. five village, Xuanwu District, Nanjing, Jiangsu Province Patentee before: INSTITUTE OF CHEMICAL INDUSTRY OF FOREST PRODUCTS, CAF |
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