CN110003112A - Compound, warm-mixed asphalt, asphalt and its preparation method and application - Google Patents
Compound, warm-mixed asphalt, asphalt and its preparation method and application Download PDFInfo
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- CN110003112A CN110003112A CN201910410983.9A CN201910410983A CN110003112A CN 110003112 A CN110003112 A CN 110003112A CN 201910410983 A CN201910410983 A CN 201910410983A CN 110003112 A CN110003112 A CN 110003112A
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
- C04B26/02—Macromolecular compounds
- C04B26/26—Bituminous materials, e.g. tar, pitch
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D233/16—Radicals substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
- C04B2111/00474—Uses not provided for elsewhere in C04B2111/00
- C04B2111/0075—Uses not provided for elsewhere in C04B2111/00 for road construction
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A30/00—Adapting or protecting infrastructure or their operation
- Y02A30/30—Adapting or protecting infrastructure or their operation in transportation, e.g. on roads, waterways or railways
Abstract
The invention discloses a kind of compounds, warm-mixed asphalt, asphalt and its preparation method and application.The structural formula of the compound as shown in Formulas I-a, Formulas I-b, Formulas I-c or Formulas I-d,Wherein, the integer that n is 1~4；R1ForThe integer that y is 0~6；R5For saturated or unsaturated C10~30Fatty alkyl；The unsaturated C10~30Unsaturated group in fatty alkyl is alkenyl；R2ForThe integer that m is 0~6；R3Or R4It is each independently hydrogen ,-COOH or C1~C4Alkyl, but R3And R4It is not simultaneously hydrogen.Compound provided by the invention can not only reduce the risk that Moisture Damage and cold cracking occur for asphalt, guarantee that its properties is all satisfied the performance requirement of bitumen for road use, and preparation process is simple and cost is relatively low, can be used using existing equipment.
Description
The application be the applying date be on 03 07th, 2016 application No. is 201610128686.1 it is entitled " compound,
The divisional application of the application for a patent for invention of warm-mixed asphalt, asphalt and its preparation method and application ".
Technical field
The present invention relates to road asphalt technical fields, are specifically related to compound, warm-mixed asphalt, asphalt and its system
Preparation Method and application.
Background technique
Currently used for the asphalt of Bituminous Pavement Construction, maintenance, there are two main classes: hot-mix asphalt mixture and cold mixing
(room temperature) asphalt.Hot-mix asphalt mixture refers to what pitch and mineral aggregate mixed and stirred under high temperature (150 DEG C~185 DEG C) situation
Mixture；Cold mixing (room temperature) asphalt refers to emulsified asphalt or cut-back asphalt and mineral aggregate in room temperature (10 DEG C~40 DEG C) shape
It is mixed and stirred under state, the mixture of making.Hot-mix asphalt mixture using at most, but mix and stir, transport and paving process in occur
The problems such as noxious gas emission, excessive energy consumption and heat ageing, is than more prominent；And cold-mix asphalt mixture, although in environmental protection, energy
Consumption etc. has great advantage, but since there are also larger gaps compared with hot-mix asphalt mixture for its pavement performance, can only
For layer and base below the maintenance of bituminous pavement, low volume of traffic road surface, middle heavy traffic flow road surface.
Exactly in this context, Europe the 1990s has started the research of Warm-Mix Bitumen Mixture, it is one
Class mixes and stirs temperature between hot-mix asphalt mixture (150 DEG C~185 DEG C) and cold mixing (10 DEG C~40 DEG C) asphalt, property
The novel asphalt mixture that hot-mix asphalt mixture can be reached or approached mixes and stirs compacting temperature and is generally 110 DEG C~130 DEG C.
For opposite plain asphalt, the temperature of mixing and stirring of modified pitch also needs to improve, and the country such as America and Europe is less to use modified pitch.
It can be alleviated well using Warm-Mix Bitumen Mixture several caused by hot-mix asphalt mixture is mixed and stirred due to high temperature
Problem: 1) the noxious gas emission problem under high temperature.According to external examining report, asphalt is mixed from heat to be switched to warm mix and can make
Carbon dioxide CO2 discharge reduces about 1/2, and carbon monoxide CO discharge reduces about 2/3, and sulfur dioxide SO2 reduces 40%, nitrogen oxide
NOx class reduces nearly 60%, and the environmental benefit using warm mix asphalt technologies is obviously.2) energy consumption problem.According to state
Outer document report can reduce by 30% or more fuel consumption using Warm-Mix Bitumen Mixture.3) ageing of asphalt caused by construction at high temperature
Problem.
Pitch warm mix technology can be divided into three categories according to working mechanism: foamed asphalt technology；Foamed asphalt technology；
Sasobit wax technology and Evotherm technology based on surfactant platform.
1) foamed asphalt viscosity reduction technology: domestic and international product is with Aspha-Min, easily paving 130 and mixing plant
Based on DoubleBarrel Green, foamed using water to pitch, to reduce asphalt viscosity, improve asphalt and
Yi Xing.The Aspha-Min dosage that Eurovia company suggests is the 0.3% of mixture quality, than typical hot-mix asphalt mixture
Production temperature reduce 12 DEG C, construction temperature can reduce by 30 DEG C.It is reported that production temperature reduces by 12 DEG C, energy consumption will be reduced about
30%.By domestic and foreign scholars studies have shown that not adding antistripping agent in the case where, the mixture containing Aspha-Min zeolite
It is poorer than the water resistant damage capability of plain asphalt mixture.In addition this technology is to the more demanding of mixing equipment.
2) organic viscosity reduction warm mix technology: by using organic thinner, viscosity when heated bitumen mix is reduced, with wax or wax
Based on shape object；Wherein based on Sasobit synthetic wax, Sasobit is the product of Sasol Wax company, it is a kind of polyolefin
Modified pitch high temperature viscosity can be effectively reduced in class Fischer Tropsch waxes, reduces mix and forming temperature, Hurley et al. is systematically
Have rated the performance of the Warm-Mix Bitumen Mixture using Sasobit, it is believed that 2.5% Sasobit synthetic wax is added in pitch
Afterwards, 129 DEG C of minimum mix temperature of recommendation are minimum to roll 110 DEG C of temperature.However, too low mix and rolling temperature and will increase
A possibility that track disease occurs, and excessively high volume will increase the risk of cold cracking.
3) surface-active warm mix technology: this method is by virtue Wei Shiweike company, the U.S. (MeadWestvaco) in 2003
The technology for acting the simultaneously step by step input application that begins one's study year, is known as Evotherm warm mix technology in the U.S..This method can be in mixture
While performance reaches hot-mix asphalt mixture, temperature will be mixed and stirred and be down to 110 DEG C~130 DEG C.Evotherm warm mix technology is
Develop to third generation warm mix technology, and China it is familiar be the second generation surface-active warm mix technology, use water base
Based on the Evotherm of emulsion dispersion technology, action principle is that water-based emulsion agent forms structure moisture film in pitch, is increased mixed
The workability of material is closed, reduces mixture mix temperature to reach, but warm-mixing agent moisture largely volatilizees during mix, easily causes and sets
The frequent replacement of standby corrosion and filter cloth bag cannot directly prepare warm-mixed asphalt simultaneously because its warm mix mechanism of action, but
Mix pot is sprayed into simultaneously with pitch during mix, causes addition reforming equipment and operating expenses is caused to increase, it is comprehensive to use
Higher cost.And third generation product, it is anhydrous type surface-active class warm-mixing agent, is directly added into bituminous cements, in mixture
Before mix, warm-mixing agent is added into asphalt tank, is sufficiently stirred and guarantees that warm-mixing agent is dispersed in pitch.In the process of mixing and stirring
In, under the action of machinery mixes and stirs power, nonpolar head reversion occurs for warm-mixing agent, and a large amount of structural lubrications are formed inside pitch
Structure.The lubrication system will avoid the reuniting effect of bituminous cements during mixing and stirring, and can dramatically increase asphalt
Workability is mixed and stirred in lower temperature.In compacting process, in the vibroroller cmpacting of steel roller and rubbing for pneumatic-tired rollers
Stranding rolls under effect, and lubricating action is played to the greatest extent, and the adjustment of collection discharge position and skeleton structure formation are more easier, and promotees
It is compacted into asphalt.When compacting ends, under the action of mechanical mastication forces and environmental factor, micelle lubrication system is gradually
It scatters and disappears, interfacial migration occurs for surface-active class chemical substance therein, is transferred on asphalt and aggregate interface, forms chemical anchors
Fixing structure reinforces the adhesive property to gather materials with bituminous cements, improves the service life of road.So third generation anhydrous type table
The comprehensive performance of face activity class warm-mixing agent is more advantageous.
Research of the China in warm mix field is started late, and warm mix technology is based on external product at present, higher cost, therefore
Develop it is a kind of efficiently, the warm-mixed asphalt additive of advantage of lower cost is a problem to be solved.
Summary of the invention
The technical problem to be solved by the present invention is at high cost existing for existing warm mix technology in order to overcome, equipment when use
It is required that the defects of high, and provide a kind of compound, warm-mixed asphalt, asphalt and its preparation method and application.The present invention
The compound of offer can not only reduce the risk that Moisture Damage and cold cracking occur for asphalt, guarantee that its properties is full
The performance requirement of sufficient bitumen for road use, and preparation process is simple and cost is relatively low, can be used using existing equipment.
In order to achieve the above object, technical solution of the present invention first is that: provide a kind of compound, structural formula such as formula
Shown in I-a, Formulas I-b, Formulas I-c or Formulas I-d:
Wherein, the integer that n is 1~4；
R1ForThe integer that y is 0~6；R5For saturated or unsaturated C10~30Fatty alkane
Base；The unsaturated C10~30Unsaturated group in fatty alkyl is alkenyl；
R2ForThe integer that m is 0~6；
R3Or R4It is each independently hydrogen ,-COOH or C1~C4Alkyl, but R3And R4It is not simultaneously hydrogen.
In the present invention, the n preferably 1 or 2；The y preferably 1,2 or 3；The m preferably 0,1 or 2；.
In the present invention, the C1~C4The preferred methyl of alkyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group or uncle
Butyl.
In the present invention, the C of the saturation10~30Fatty alkyl refers to branch or straight chain including 10~30 carbon atoms
Radical of saturated aliphatic alkyl；The C of the saturation10~30Fatty alkyl is preferably 10~29 carbon atoms, is more preferably 17~28
The radical of saturated aliphatic alkyl of a carbon atom；The unsaturated C10~30In fatty alkyl, the position of the alkenyl and quantity do not have
Particular determination, the integer (such as 1,2,3,4 or 5) that the quantity of the alkenyl is 1~5；Further, the unsaturation
C10~30Fatty alkyl is preferably CH3(CH2)a(CH=CH) (CH2)c, the sum of a and c are 7~26；The unsaturated C10~30
Fatty alkyl is more preferably CH3(CH2)7(CH=CH) (CH2)7。
Technical solution of the present invention second is that: a kind of preparation method of compound is provided, when the compound
When for I-a or I-b, the preparation method comprises the following steps:
(1) amido amine or imidazolinyl amine V reacted using fatty acid with vinylamine is raw materials, with halogenated alkyl acid
Alkylated reaction occurs for IV-a；The ratio between described amount of substance of compound V and halogeno-group acid is 1:0.1~1:3；
(2) resulting alkyl acid III-a is reacted with vinylamine II to get the compound I-a or I-b；The alkyl
The ratio between amount of substance of sour III-a and vinylamine II is 1:0.1~1:3；When the temperature of the reaction is 180-190 DEG C, dehydration
Amount is 1 times of the amount of the substance of halogenated alkyl acid IV-a, and product is the compound I-a；The temperature of the reaction is 260-270
DEG C, dehydrating amount is that 2 times of products of the amount of the substance of halogenated alkyl acid IV-a are the compound I-b；
Wherein, one of X Cl, Br and I；
When the compound is I-c or I-d, the preparation method comprises the following steps:
(S1) amido amine or imidazolinyl amine V reacted using fatty acid with vinylamine is raw materials, with α, β-insatiable hunger
With sour IV-c carry out Michael addition reaction, the compound V and α, the ratio between amount of substance of beta-unsaturated acid be 1:0.1~
1:2；
(S2) resulting alkyl acid III-c is reacted with vinylamine II to get the compound I-c or I-d；The alkyl
The ratio between amount of substance of sour III-c and vinylamine II is 1:1~1:3；When the temperature of the reaction is 180-190 DEG C, dehydrating amount
For α, 1 times of the amount of the substance of beta-unsaturated acid IV-c, product is the compound I-c；When the temperature of the reaction is 260-
At 270 DEG C, dehydrating amount α, 2 times of the amount of the substance of beta-unsaturated acid IV-c, product is the compound I-d；
In step (1), the vinylamine is N- aminoethylpiperazine, diethylenetriamines, trien, four Asias
One of five amine of ethyl, penten and polyethylene polyamine are a variety of.
In step (1), the temperature of the alkylated reaction is 25 DEG C~80 DEG C；The time of the reaction is 1~10
Hour；The alkylated reaction can be reacted in the case where having solvent or solvent-free situation；When reacting in a solvent, the solvent
It can be solvent commonly used in the art.
In step (1), the carbon atom number of the halogenated alkyl acid is 2~5, and the halogenated alkyl acid is preferably chlorine
Acetic acid, bromoacetic acid, iodoacetic acid or 3- chloropropionic acid.
In step (S1), the carbon atom number of the fatty acid is 10~30, and the fatty acid is preferably tall oil
Fatty acid.
In step (S1), the vinylamine is N- aminoethylpiperazine, diethylenetriamines, trien, four
One of five amine of ethylidene, penten and polyethylene polyamine are a variety of.
In step (S1), the α, beta-unsaturated acid is acrylic acid, methacrylic acid or fumaric acid.
In step (S1), the temperature of the Michael addition reaction is preferably 25 DEG C~80 DEG C；The reaction
Time is preferably 1~10 hour；Step (S1) Michael addition reaction can be reacted in the case where having solvent or solvent-free situation；?
When reacting in solvent, the solvent can be solvent commonly used in the art.
Technical solution of the present invention third is that: provide the one or more as warm-mixed asphalt additive of the compound
Application.
The inventors of the present invention discovered through researches that the compound with above-mentioned molecular structure has two for the mechanism of action of warm mix
Aspect: during mixing and stirring, under the action of machinery mixes and stirs power, nonpolar head reversion occurs for warm-mixed asphalt additive, is dripping
The green a large amount of structural lubrication systems of internal formation；The polarity in polar group and resin and asphalt in surfactant molecule
Group forms stronger hydrogen bond, is piled up with destroying the plane of colloid, asphaltene molecules, and formation is random to pile up, and becomes structure
Loosely, ordering degree reduces, and becomes the aggregation for having surfactant to participate in, to play the role of viscosity reduction.
Technical solution of the present invention fourth is that: a kind of preparation method of warm-mixed asphalt is provided, in the compound
One or more and pitch be raw material, the preparation method the following steps are included: by one of described compound or
It is a variety of to be added in the pitch of melting, it heats, stirring, wherein the additive amount of the compound is the 3 ‰ of asphalt quality
~7 ‰.
Wherein, the pitch is preferably asphalt, oxidized asphalt, heavy traffic polymer modified asphalt, bitumen
With one of tar asphalt or a variety of.
Wherein, the temperature being heated to is preferably 135 DEG C~150 DEG C；The time of the stirring is preferably 20min
~60min.
Technical solution of the present invention fifth is that: provide a kind of temperature prepared by above-mentioned warm-mixed asphalt preparation method
Mix pitch.
Technical solution of the present invention sixth is that: provide a kind of preparation method of Warm-Mix Bitumen Mixture comprising following
Step, mix after the warm-mixed asphalt and aggregate are heated respectively；Wherein, the warm-mixed asphalt and the aggregate
Mass ratio is preferably (4%~6%): (94%~96%).
Wherein, the temperature that the aggregate is heated to is preferably 115 DEG C~155 DEG C；The temperature that the warm-mixed asphalt is heated to
Preferably 135 DEG C~150 DEG C of degree；The aggregate is preferably AC-13 graded aggregate.
Technical solution of the present invention seventh is that: provide a kind of prepare by above-mentioned Warm-Mix Bitumen Mixture preparation method and obtain
The Warm-Mix Bitumen Mixture obtained.
Technical solution of the present invention eighth is that: provide a kind of above-mentioned Warm-Mix Bitumen Mixture answering in highway engineering
With；Wherein, the mix temperature of the Warm-Mix Bitumen Mixture is preferably 125 DEG C~145 DEG C, and forming temperature is preferably 120
DEG C~140 DEG C.
On the basis of common knowledge of the art, above-mentioned each optimum condition, can any combination to get each preferable reality of the present invention
Example.
The reagents and materials used in the present invention are commercially available.
The positive effect of the present invention is that:
1) the compound of the present invention is based on surface active process, can not only reduce asphalt and Moisture Damage and low temperature occurs
The risk of cracking guarantees that its properties is all satisfied the performance requirement of bitumen for road use, and preparation process is simple and cost is relatively low；
2) the compound of the present invention can make the mix temperature of asphalt reduce by 20 DEG C~50 DEG C, significantly reduce warm mix
The degree of aging of pitch achievees the purpose that energy-saving and emission-reduction and reduces cost have simple process, energy conservation and environmental protection and cost is relatively low
Feature, without additional addition or reforming equipment；
3) Warm-Mix Bitumen Mixture preparation method provided by the present invention is suitable for various AC type asphalts, SMA is dripped
Green mixture, OGFC asphalt, ECA ultrathin overlay asphalt, warm mix modified pitch (especially SBS modified pitch)
Various types of asphalts such as mixture and rubber-asphalt mixture.
Specific embodiment
The present invention is further illustrated below by the mode of embodiment, but does not therefore limit the present invention to the reality
It applies among a range.In the following examples, the experimental methods for specific conditions are not specified, according to conventional methods and conditions, or according to quotient
The selection of product specification.
In an embodiment of the present invention, the softening point test of warm-mixed asphalt, ductility test and penetration test, warm-mixed asphalt
Mix and the moulding process test of mixture, voidage are tested, Marshall residual stability tests freeze-thaw split intensity ratio test,
The testing methods such as track dynamic stability test and low-temperature bending test are all made of " highway engineering pitch and pitch mixing
Expect testing regulations " (JTGE20-2011) defined standard.
Embodiment 1
Weigh compound V-1 that oleic acid prepares according to a conventional method with triethylene tetramine (prepare according to a conventional method, will be oily
Acid and triethylene tetramine are mixed by 1:1 molar ratio, are heated to 250-260 DEG C, and logical nitrogen dehydration can be prepared by) total 392g addition
It in the three-necked flask of 1000mL, is then slowly added into monoxone IV-a-1 (94g, 1mol), reaction temperature rises, control reaction temperature
Degree reacts 3h, obtains compound III-a-1 at 80 DEG C.Then triethylene tetramine II-1 (146g, 1mol) is added, reaction temperature
It is raised to 180-190 DEG C, steam is bloated using nitrogen, water segregator is collected into moisture 18g, stops reaction, cool down to obtain compound I-a-
1.Yield is 614g, yield 100%.1H NMR (400MHz, CDCl3) δ ppm 5.33 (dt, J=6.8,12Hz, 2H),
3.62-3.60 (m, 1H), 3.40-3.24 (m, 4H), 3.20-3.15 (m, 1H), 2.81-2.56 (m, 17H), 2.52-2.38 (m,
5H), 2.17-2.12 (m, 2H), 2.05-1.95 (m, 2H), 1.35-1.24 (m, 22H), 0.86 (t, J=6.8Hz, 3H).
The preparation of warm-mixed asphalt: take the warm-mixed asphalt additive I-a-1 of pitch weight 5 ‰ that the 70# petroleum drip of melting is added
In blueness, it is heated to 135 DEG C and stirs 20min to get warm-mixed asphalt.
Gained warm-mixed asphalt is heated to 135 DEG C, aggregate is heated to 135 DEG C；It is added again into mix pot and accounts for warm-mixed asphalt
The warm-mixed asphalt of mixture quality percentage 5% and 95% AC-13 graded aggregate, mix i.e. be prepared warm-mixed asphalt mixing
Material.Rotation is compacted into test specimen at 120 DEG C.
The particular technique index of gained warm-mixed asphalt and Warm-Mix Bitumen Mixture is as shown in table 1, table 2, table 3 and table 4.
Embodiment 2
Weigh compound V-2 that oleic acid prepares according to a conventional method with tetraethylenepentamine (prepare according to a conventional method, will be oily
Acid and tetraethylenepentamine are mixed by 1:1 molar ratio, are heated to 250-260 DEG C, and logical nitrogen dehydration can be prepared by) total 435g addition
It in the three-necked flask of 1000mL, is then slowly added into acrylic acid IV-a-2 (72g, 1mol), reaction temperature rises, control reaction temperature
Degree reacts 3h, obtains compound III-a-2 at 80 DEG C.Then tetraethylenepentamine II-2 (189g, 1mol) is added, reaction temperature
It is raised to 180-190 DEG C, steam is bloated using nitrogen, water segregator is collected into moisture 18g, stops reaction, cool down to obtain compound I-c-
2.Yield is 678g, yield 100%.1H NMR (400MHz, CDCl3) δ ppm 5.32 (dt, J=6.8,11.6Hz, 2H),
3.67-3.60 (m, 1H), 3.40-3.24 (m, 4H), 3.21-3.13 (m, 1H), 2.81-2.61 (m, 24H), 2.58-2.41 (m,
8H), 2.17-2.13 (m, 2H), 2.05-1.96 (m, 2H), 1.33-1.24 (m, 22H), 0.86 (t, J=6.8Hz, 3H).
The preparation of warm-mixed asphalt: take the warm-mixed asphalt additive I-c-2 of pitch weight 5 ‰ that the 70# petroleum drip of melting is added
In blueness, it is heated to 135 DEG C and stirs 20min to get warm-mixed asphalt.
Gained warm-mixed asphalt is heated to 135 DEG C, aggregate is heated to 135 DEG C；It is added again into mix pot and accounts for warm-mixed asphalt
The warm-mixed asphalt of mixture quality percentage 4% and 96% AC-13 graded aggregate, mix i.e. be prepared warm-mixed asphalt mixing
Material.Rotation is compacted into test specimen at 120 DEG C.
The particular technique index of gained warm-mixed asphalt and Warm-Mix Bitumen Mixture is as shown in table 1, table 2, table 3 and table 4.
Embodiment 3
Then tetraethylenepentamine II-2 (189g, 1mol) is added in the compound III-a-2 of 507g, reaction temperature is raised to
260-270 DEG C, steam is bloated using nitrogen, water segregator is collected into moisture 36g, stops reaction, cool down to obtain compound I-b-2.It produces
Amount is 660g, yield 100%.1H NMR (400MHz, CDCl3) δ ppm 5.32 (dt, J=6.8,11.6Hz, 2H), 3.67-
3.60 (m, 2H), 3.40-3.24 (m, 4H), 3.21-3.13 (m, 2H), 2.81-2.61 (m, 22H), 2.58-2.41 (m, 8H),
2.17-2.13 (m, 2H), 2.05-1.96 (m, 2H), 1.33-1.24 (m, 22H), 0.86 (t, J=6.8Hz, 3H).
The preparation of warm-mixed asphalt: take the warm-mixed asphalt additive I-b-2 of pitch weight 5 ‰ that the 70# petroleum drip of melting is added
In blueness, it is heated to 135 DEG C and stirs 20min to get warm-mixed asphalt.
Gained warm-mixed asphalt is heated to 135 DEG C, aggregate is heated to 135 DEG C；It is added again into mix pot and accounts for warm-mixed asphalt
The warm-mixed asphalt of mixture quality percentage 4% and 96% AC-13 graded aggregate, mix i.e. be prepared warm-mixed asphalt mixing
Material.Rotation is compacted into test specimen at 120 DEG C.
The particular technique index of gained warm-mixed asphalt and Warm-Mix Bitumen Mixture is as shown in table 1, table 2, table 3 and table 4.
Embodiment 4
Weigh compound V-3 that oleic acid prepares according to a conventional method with tetraethylenepentamine (prepare according to a conventional method, will be oily
Acid and tetraethylenepentamine are mixed by 1:1 molar ratio, are heated to 250-260 DEG C, and logical nitrogen dehydration can be prepared by) total 435g addition
It in the three-necked flask of 1000mL, is then slowly added into methacrylic acid IV-c-3 (86g, 1mol), reaction temperature rises, and control is anti-
It answers temperature at 80 DEG C, reacts 3h, obtain compound III-c-3.Then triethylene tetramine II-3 (146g, 1mol) is added, reaction
Temperature is raised to 260-270 DEG C, bloats steam using nitrogen, and water segregator is collected into moisture 36g, stops reaction, cool down to obtain compound
I-d-3.Yield is 631g, yield 100%.1H NMR (400MHz, CDCl3) δ ppm 5.33 (dt, J=6.8,11.6Hz,
2H), 3.66-3.60 (m, 2H), 3.39-3.24 (m, 4H), 3.19-3.13 (m, 2H), 2.81-2.60 (m, 18H), 2.57-
2.41 (m, 7H), 2.17-2.14 (m, 2H), 2.04-1.96 (m, 2H), 1.35-1.24 (m, 22H), 1.15 (d, J=7.2Hz,
3H), 0.86 (t, J=6.8Hz, 3H).
The preparation of warm-mixed asphalt: take the warm-mixed asphalt additive I-d-3 of pitch weight 4 ‰ that the 70# petroleum drip of melting is added
In blueness, it is heated to 135 DEG C and stirs 20min to get warm-mixed asphalt.
Gained warm-mixed asphalt is heated to 135 DEG C, aggregate is heated to 135 DEG C；It is added again into mix pot and accounts for warm-mixed asphalt
The warm-mixed asphalt of mixture quality percentage 4.5% and 95.5% AC-13 graded aggregate, warm-mixed asphalt is prepared in mix
Mixture.Rotation is compacted into test specimen at 120 DEG C.
The particular technique index of gained warm-mixed asphalt and Warm-Mix Bitumen Mixture is as shown in table 1, table 2, table 3 and table 4.
Embodiment 5
By 1 prepare compound I-a-1 of embodiment.
The preparation of warm mix modified pitch: the warm-mixed asphalt additive I-a-1 of pitch weight 5.5 ‰ is added to the SBS of melting
In modified pitch, it is heated to 150 DEG C and stirs 20min to get warm mix modified pitch.
The preparation of warm mix modified asphalt mixture: gained warm mix modified pitch is heated to 150 DEG C, aggregate is heated to 150
℃；It is added again into mix pot and accounts for 5% warm mix modified pitch of warm mix modified asphalt mixture mass percent and 95% AC-
Warm mix modified asphalt mixture is prepared in 13 graded aggregates, mix.Rotation is compacted into test specimen at 140 DEG C.
The particular technique index of gained warm mix modified pitch and warm mix modified asphalt mixture is as shown in table 5, table 6 and table 7.
Embodiment 6
By 2 prepare compound I-c-2 of embodiment.
The preparation of warm mix modified pitch: the warm-mixed asphalt additive I-b-2 of pitch weight 5 ‰ SBS that melting is added is changed
In property pitch, it is heated to 150 DEG C and stirs 20min to get warm mix modified pitch.
The preparation of warm mix modified asphalt mixture: gained warm mix modified pitch is heated to 150 DEG C, aggregate is heated to 150
℃；It is added again into mix pot and accounts for 5% warm mix modified pitch of warm mix modified asphalt mixture mass percent and 95% AC-
Warm mix modified asphalt mixture is prepared in 13 graded aggregates, mix.Rotation is compacted into test specimen at 135 DEG C.
The particular technique index of gained warm mix modified pitch and warm mix modified asphalt mixture is as shown in table 5, table 6 and table 7.
Embodiment 7
By 3 prepare compound I-b-2 of embodiment.
The preparation of warm mix modified pitch: the warm-mixed asphalt additive I-b-2 of pitch weight 5 ‰ SBS that melting is added is changed
In property pitch, it is heated to 150 DEG C and stirs 20min to get warm mix modified pitch.
The preparation of warm mix modified asphalt mixture: gained warm mix modified pitch is heated to 150 DEG C, aggregate is heated to 150
℃；It is added again into mix pot and accounts for 5% warm mix modified pitch of warm mix modified asphalt mixture mass percent and 95% AC-
Warm mix modified asphalt mixture is prepared in 13 graded aggregates, mix.Rotation is compacted into test specimen at 135 DEG C.
The particular technique index of gained warm mix modified pitch and warm mix modified asphalt mixture is as shown in table 5, table 6 and table 7.
Embodiment 8
By 4 prepare compound I-d-3 of embodiment.
The preparation of warm mix modified pitch: the warm-mixed asphalt additive I-d-3 of pitch weight 5 ‰ SBS that melting is added is changed
In property pitch, it is heated to 150 DEG C and stirs 20min to get warm mix modified pitch.
The preparation of warm mix modified asphalt mixture: gained warm mix modified pitch is heated to 150 DEG C, aggregate is heated to 150
℃；It is added again into mix pot and accounts for 5% warm mix modified pitch of warm mix modified asphalt mixture mass percent and 95% AC-
Warm mix modified asphalt mixture is prepared in 13 graded aggregates, mix.Rotation is compacted into test specimen at 135 DEG C.
The particular technique index of gained warm mix modified pitch and warm mix modified asphalt mixture is as shown in table 5, table 6 and table 7.
Comparative example 1
In this comparative example, asphalt is using 70# asphalt and aggregate mix, the ductility of 70# asphalt, needle
The technical indicators such as in-degree and softening point are shown in Table 1, the test of mix and moulding process, the voidage test, Marshall of asphalt
The technical indicators such as residual stability test, freeze-thaw split intensity ratio test, track dynamic stability test and the small beam deflection of low temperature are shown in
Table 2, table 3 and table 4.
Comparative example 2
In this comparative example, asphalt is using SBS modified pitch and aggregate mix, the ductility of SBS modified pitch, needle
The technical indicators such as in-degree and softening point are shown in Table 5, voidage, Marshall residual stability, the freeze-thaw split intensity of asphalt
The technical indicators such as beam deflection smaller than, track dynamic stability and low temperature are shown in Table 6 and table 7.
Table 1
| Project | Comparative example 1 | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 |
| Soft access point (DEG C) | 48.6 | 47.5 | 48.3 | 47.7 | 48.2 |
| Needle penetration (0.1mm) | 72 | 70 | 74 | 73 | 72 |
| 10 DEG C of ductilities (cm) | 92.5 | 96.2 | 96.4 | 97.1 | 95.6 |
From table 1 it follows that compared with comparative example 1, the needle penetration of Examples 1 to 4 warm-mixed asphalt, softening point and do not add
Add warm-mixing agent asphalt performance suitable, the performance of asphalt, illustrates warm mix in the slightly excellent comparative example 1 of 10 DEG C of ductilities of warm-mixed asphalt
The cryogenic property of pitch is improved to a certain extent.
Table 2
Table 3
| Project | Comparative example 1 | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 |
| Voidage (%) | 4.6 | 4.6 | 4.7 | 4.5 | 4.5 |
As can be seen that being compared with comparative example 1, the voidage of the Warm-Mix Bitumen Mixture of Examples 1 to 4 from table 2 and table 3
It is suitable with the voidage of blank example hot-mix asphalt mixture, therefore under the premise of reaching identical consolidation effect, warm mix of the invention
The asphalt of asphalt modifier can significantly reduce pitch and building stones mix temperature and forming temperature, cooling extent about 35~40
℃。
The test of Marshall residual stability, freeze-thaw split intensity ratio, dynamic stability and low temperature bend test the results are shown in Table 4.
Table 4
From table 4, it can be seen that compared with comparative example 1, Examples 1 to 4 Warm-Mix Bitumen Mixture water stabilizing and high temperature
Anti-rut behavior is suitable, and crack resistance at low-temperature makes moderate progress.Therefore the asphalt of warm-mixed asphalt additive of the invention is each
Item performance is able to satisfy " standard specification for construction and acceptance of highway asphalt pavement " (JTGF40-2004) associated specifications.
Table 5
| Project | Comparative example 2 | Embodiment 5 | Embodiment 6 | Embodiment 7 | Embodiment 8 |
| Soft access point (DEG C) | 60.2 | 58.8 | 59.4 | 60.1 | 59.8 |
| Needle penetration (0.1mm) | 65 | 67 | 65 | 66 | 65 |
| 5 DEG C of ductilities (cm) | 32.3 | 33.6 | 33.1 | 34.1 | 33.8 |
Table 6
| Project | Comparative example 2 | Embodiment 5 | Embodiment 6 | Embodiment 7 | Embodiment 8 |
| Aggregate heating temperature (DEG C) | 190 | 150 | 150 | 150 | 150 |
| Mix and stir temperature (DEG C) | 180 | 145 | 145 | 140 | 140 |
| Forming temperature (DEG C) | 170 | 140 | 135 | 135 | 135 |
Table 7
From table 5, table 6 and table 7 as can be seen that compared with comparative example 2,5~8 warm mix modified pitch indices of embodiment with
SBS hot-mix asphalt mixture is suitable, while when mix temperature reduces by 35~40 DEG C, warm mix modified asphalt mixture water is steady
Qualitative energy, high temperature anti-rut behavior and crack resistance at low-temperature make moderate progress.Therefore the SBS pitch of warm-mixed asphalt additive of the invention
The properties of mixture are able to satisfy " standard specification for construction and acceptance of highway asphalt pavement " (JTGF40-2004) associated specifications.
Claims (10)
1. a kind of compound, which is characterized in that its structural formula is as shown in Formulas I-a, Formulas I-b, Formulas I-c or Formulas I-d:
Wherein, the integer that n is 1~4；
R1ForThe integer that y is 0~6；R5For saturated or unsaturated C10~30Fatty alkyl；It is described
Unsaturated C10~30Unsaturated group in fatty alkyl is alkenyl；
R2ForThe integer that m is 0~6；
R3Or R4It is each independently hydrogen ,-COOH or C1~C4Alkyl, but R3And R4It is not simultaneously hydrogen.
2. compound as described in claim 1, which is characterized in that the n is 1 or 2；The y is 1,2 or 3；Described
M is 0,1 or 2；
And/or the C1~C4Alkyl is methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group or tert-butyl；
And/or the C of the saturation10~30Fatty alkyl is 10~29 carbon atoms, preferably 17~28 carbon atoms it is full
And aliphatic alkyl；The unsaturated C10~30The integer that the quantity of alkenyl described in fatty alkyl is 1~5；The unsaturation
C10~30Fatty alkyl is preferably CH3(CH2)a(CH=CH) (CH2)c, the sum of a and c are 7~26；The unsaturated C10~30
Fatty alkyl is more preferably CH3(CH2)7(CH=CH) (CH2)7。
3. a kind of preparation method of compound as claimed in claim 1 or 2, which is characterized in that when the compound is I-a or I-
When b, the preparation method comprises the following steps:
(1) amido amine or imidazolinyl amine V reacted using fatty acid with vinylamine is raw materials, with halogenated alkyl acid IV-a
Alkylated reaction occurs；The ratio between described amount of substance of compound V and halogeno-group acid is 1:0.1~1:3；
(2) resulting alkyl acid III-a is reacted with vinylamine II to get the compound I-a or I-b；The alkyl acid
The ratio between amount of substance of III-a and vinylamine II is 1:0.1~1:3；When the temperature of the reaction is 180-190 DEG C, dehydrating amount
It is 1 times of the amount of the substance of halogenated alkyl acid IV-a, product is the compound I-a；The temperature of the reaction is 260-270
DEG C, dehydrating amount is that 2 times of products of the amount of the substance of halogenated alkyl acid IV-a are the compound I-b；
Wherein, one of X Cl, Br and I；
When the compound is I-c or I-d, the preparation method comprises the following steps:
(S1) amido amine or imidazolinyl amine V reacted using fatty acid with vinylamine is raw materials, with α, beta-unsaturated acid
IV-c carries out Michael addition reaction, the compound V and α, and the ratio between amount of substance of beta-unsaturated acid is 1:0.1~1:2；
(S2) resulting alkyl acid III-c is reacted with vinylamine II to get the compound I-c or I-d；The alkyl acid
The ratio between amount of substance of III-c and vinylamine II is 1:1~1:3；When the temperature of the reaction is 180-190 DEG C, dehydrating amount is
α, 1 times of the amount of the substance of beta-unsaturated acid IV-c, product is the compound I-c；When the temperature of the reaction is 260-270
DEG C when, dehydrating amount α, 2 times of the amount of the substance of beta-unsaturated acid IV-c, product be the compound I-d；
4. preparation method as claimed in claim 3, which is characterized in that in step (1), the vinylamine is N- amino-ethyl
One in piperazine, diethylenetriamines, trien, tetren, penten and polyethylene polyamine
Kind is a variety of；
And/or in step (1), the temperature of the alkylated reaction is 25 DEG C~80 DEG C；The time of the reaction be 1~
10 hours；
And/or in step (1), the carbon atom number of the halogenated alkyl acid is 2~5, and the halogenated alkyl acid is preferably
Monoxone, bromoacetic acid, iodoacetic acid or 3- chloropropionic acid；
And/or in step (S1), the carbon atom number of the fatty acid is 10~30, and the fatty acid is preferably Carvedilol
Fatty acid oil；
And/or in step (S1), the vinylamine be N- aminoethylpiperazine, diethylenetriamines, trien,
One of tetren, penten and polyethylene polyamine are a variety of；
And/or in step (S1), the α, beta-unsaturated acid is acrylic acid, methacrylic acid or fumaric acid；
And/or in step (S1), the temperature of the Michael addition reaction is 25 DEG C~80 DEG C；The time of the reaction
It is 1~10 hour.
5. application of the one or more compounds of any of claims 1 or 2 as warm-mixed asphalt additive.
6. a kind of preparation method of warm-mixed asphalt, which is characterized in that the preparation method comprises the following steps: by claim 1
2 one of the compound or it is a variety of be added in the pitch of melting, heat, stirring；Wherein, the compound
Additive amount be asphalt quality 3 ‰~7 ‰；
Wherein, the pitch is preferably asphalt, oxidized asphalt, heavy traffic polymer modified asphalt, bitumen and coke
One of oil asphalt is a variety of；
The temperature of the heating is preferably 135 DEG C~150 DEG C；The time of the stirring is preferably 20min~60min.
7. a kind of warm-mixed asphalt, which is characterized in that it is prepared by preparation method as claimed in claim 6.
8. a kind of preparation method of Warm-Mix Bitumen Mixture, which is characterized in that it includes the following steps, will be described in claim 7
Warm-mixed asphalt and aggregate heat respectively after mix；Wherein, the mass ratio of the warm-mixed asphalt and the aggregate is
(4%~6%): (94%~96%)；
Wherein, the temperature of the aggregate heating is preferably 115 DEG C~155 DEG C；The temperature of the warm-mixed asphalt heating is preferably
It is 135 DEG C~150 DEG C；The aggregate is preferably AC-13 graded aggregate.
9. a kind of Warm-Mix Bitumen Mixture, which is characterized in that it is prepared by preparation method according to any one of claims 8
's.
10. a kind of application of Warm-Mix Bitumen Mixture as claimed in claim 9 in highway engineering；The Warm-Mix Bitumen Mixture
Mix temperature be preferably 125 DEG C~145 DEG C, forming temperature is preferably 120 DEG C~140 DEG C.
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| CN1180082A (en) * | 1997-11-04 | 1998-04-29 | 辽河石油勘探局公路工程公司 | Additive of asphalt and stone material and preparing method thereof |
| CN101848969A (en) * | 2007-09-07 | 2010-09-29 | Alm控股公司 | Warm mix asphalt binder compositions containing lubricating additives |
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