CN108467495A - A kind of lignin quaternary ammonium salt cation asphalt emulsifier and preparation method thereof - Google Patents
A kind of lignin quaternary ammonium salt cation asphalt emulsifier and preparation method thereof Download PDFInfo
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- CN108467495A CN108467495A CN201810458396.2A CN201810458396A CN108467495A CN 108467495 A CN108467495 A CN 108467495A CN 201810458396 A CN201810458396 A CN 201810458396A CN 108467495 A CN108467495 A CN 108467495A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2395/00—Bituminous materials, e.g. asphalt, tar or pitch
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Abstract
A kind of lignin quaternary ammonium salt cation asphalt emulsifier of present invention proposition and preparation method thereof.A kind of preparation method of lignin quaternary ammonium salt cation asphalt emulsifier, general formula of molecular structure are：
Description
Technical field
The invention belongs to field of fine chemical, and in particular to a kind of lignin quaternary ammonium salt cationic type asphalt emulsifier.
Background technology
With the continuous development of asphalt applications level, the deficiency of common heated bitumen also begins to show：Pitch rate of set is too
Soon, it needs to heat repeatedly when use, this causes great energy waste and environmental pollution in use.Cold pitch is added
Heat enables pitch with a kind of fine particle in the aqueous solution containing appropriate emulsifier to viscous pasty state is melted by stirring
State is spread in the solution, forms the lotion of (O/W) shape, here it is emulsified asphalts.This asphalt emulsion is at normal temperatures with liquid
Form exists, and is in dark-brown or black, has good mobility under high temperature.Influence emulsified asphalt pavement performance most critical because
Element is exactly asphalt emulsifier, and cationic asphalt emulsifier principal item has organic amine, quaternary ammonium salt, imidazoles both at home and abroad at present
Quinoline class, amides etc., with the application of cationic emulsified bitumen, the kind of asphalt emulsifier is also gradually enriched.
United States Patent (USP) USP4338136 is with C12-18Long carbon chain aliphatic acid reacts preparation with diethylenetriamine under certain condition
Asphalt emulsifier.The disadvantages of this method is that the asphalt emulsifier for preparing is expensive, when for slurry seal construction, is demulsified the time
Long, molding time is slow, and the open to traffic time is long.Chinese patent CN1096714 utilizes oil plant by-product aphthenic acids and alkenyl polyamine
Reaction, prepares asphalt emulsifier.The disadvantages of this method is the raw material supply of emulsifier by severely restricts, is unfavorable for promoting and answer
With.Chinese patent CN1861721A is related to a kind of rosin cation asphalt emulgent.The emulsifier is by rosin and alkenyl polyamine
Reaction, obtain rosin intermediate, then, with different types of quaternary ammonium salt intermediate be condensed, be made function admirable rosin sun from
Sub- asphalt emulsifier.The shortcomings that this method is that reaction step is cumbersome, needs pyroreaction.Chinese patent CN101712625A is related to
And a kind of method for synthesizing amphoteric slow-breaking quick-setting asphalt emulsifier, it is reacted with polyamines using oleic acid and generates polyamide-polyamino, be then added
Halogenating reaction occurs for monoxone, and asphalt emulsifier is made.The disadvantages of this method is to need pyroreaction when preparing.Chinese patent
CN101745340A is related to a kind of cation asphalt emulgent preparation method, and host agent is obtained by the reaction by mixed organic acid and organic amine
Intermediate, then carry out quaternization reaction and be made, adjuvant is nonionic surfactant and modified additive.The disadvantages of this method is system
Standby complex steps, cost is higher, needs pyroreaction.
Invention content
In order to solve the above technical problems, a kind of lignin quaternary ammonium salt cationic type asphalt emulsifier of the present invention and its
Preparation method, asphalt emulsifier raw material sources prepared by the present invention are extensive, and production cost is low, and preparation process is simple, emulsifiable more
The emulsified asphalt of the pitch of kind different model, preparation is fine and smooth uniformly, and storage stability is good.
The present invention provides a kind of lignin quaternary ammonium salt cation asphalt emulsifier, and general formula of molecular structure is：
Lignin represents lignin molecule chain.
The present invention further provides a kind of preparation methods of lignin quaternary ammonium salt cation asphalt emulsifier, according to following
Step carries out：
(1) by parahydroxyben-zaldehyde, lignin, thionyl chloride and triethylamine hybrid reaction, reaction intermediate I is obtained, in
Mesosome I：
(2) by intermediate I, 3- amino -1- propyl alcohol and hydrobromic acid hybrid reaction, intermediate II is obtained, intermediate II is：
(3) by intermediate II and sodium chloroacetate hybrid reaction, lignin cation asphalt emulgent is obtained；
As long as above step does not influence to prepare, replaceable.
Improved as of the invention further, the feed proportioning ratio used for：Parahydroxyben-zaldehyde, thionyl chloride, three second
Amine, lignin, 3- amino -1- propyl alcohol, hydrobromic acid, sodium chloroacetate molar ratio be 1:(1-2):(2-8):(1-1.5):(1-2):
(1-3):(1-3)。
Improved as of the invention further, the feed proportioning ratio used for：Parahydroxyben-zaldehyde, thionyl chloride, three second
Amine, lignin, 3- amino -1- propyl alcohol, hydrobromic acid, sodium chloroacetate molar ratio be 1:(1-1.5):(2-5):(1-1.3):(1-
1.5):(1-2):(1-2)。
Improved as of the invention further, the feed proportioning ratio used for：：Parahydroxyben-zaldehyde, thionyl chloride, three second
Amine, lignin, 3- amino -1- propyl alcohol, hydrobromic acid, sodium chloroacetate molar ratio be 1:1.2:3:1.2:1.3:1.5:1.5.
As further improvement of the invention, specifically comprise the following steps：
(1) parahydroxyben-zaldehyde is added in reaction bulb, sequentially adds thionyl chloride and triethylamine, after reacting at room temperature 2-3h
Lignin is added, reaction 2h is stirred at room temperature, obtains intermediate I；
(2) intermediate I is dissolved in glacial acetic acid, 30% hydrobromic acid is added dropwise, 40-45 DEG C of reaction 2h continuously adds 3- amino-
1- propyl alcohol reacts at room temperature 3h, intermediate II；
(3) intermediate II is dissolved in dichloromethane, 0 DEG C is slowly added dropwise sodium chloroacetate, reacts 2h, obtain lignin sun from
Sub- asphalt emulsifier.
The present invention further protect above-mentioned lignin cation asphalt emulgent prepare split soon type and in split type sun from
Application in sub- emulsified asphalt.
The present invention further protects a kind of preparation method of emulsified asphalt, which is characterized in that includes the following steps：Right is wanted
It is the 1-3% of the emulsified asphalt gross mass prepared to seek the dosage of the asphalt emulsifier described in 1, adds water to match above-mentioned asphalt emulsifier
Aqueous solution is made, is heated to 65-75 DEG C, soap lye is made；By after heating pitch and emulsifier soap lye emulsified by colloid mill, add
Enter a certain amount of auxiliary agent, prepares cationic emulsified bitumen.
As further improvement of the invention, auxiliary agent includes one or more of aluminum sulfate, ammonium chloride and calcium chloride.
The present invention further protects the emulsified asphalt prepared according to the preparation method of preceding claim.
Beneficial effects of the present invention：
1, raw material sources of the invention are extensive, and production cost is low, and preparation process is simple, does not need pyroreaction；
2, the asphalt emulsifier function admirable obtained, the pitch of emulsifiable a variety of different models, the emulsified asphalt of preparation are thin
Greasy uniform, storage stability is good；
3, asphalt emulsifier prepared by the present invention meets national standard, and emulsified asphalt obtained is fine and smooth uniformly, has and splits soon
Type splits the characteristic of type asphalt emulsifier in.
Specific implementation mode
Below in conjunction with the embodiment of the present invention, technical solution in the embodiment of the present invention carries out clear, complete description,
Obviously, the embodiment described is the embodiment of the part of representative of the present invention, rather than whole embodiments, this field are general
Other all embodiments that logical technical staff is obtained without making creative work belong to the protection of the present invention
Range.
Used raw material, reagent are conventional chemical products in the embodiment of the present invention, can be purchased by commercial channel
It can buy.
The preparation of 1 lignin quaternary ammonium salt cation asphalt emulsifier of embodiment
It follows the steps below：
(1) 1mol parahydroxyben-zaldehydes are added in reaction bulb, sequentially add 1mol thionyl chlorides and 2mol triethylamines, room
1mol lignin is added after temperature reaction 2-3h, reaction 2h is stirred at room temperature, obtains intermediate I；
(2) intermediate I is dissolved in glacial acetic acid, 30% hydrobromic acids of 1mol is added dropwise, 40-45 DEG C of reaction 2h continuously adds 1mol
3- amino -1- propyl alcohol reacts at room temperature 3h, intermediate II；
(3) intermediate II is dissolved in dichloromethane, 0 DEG C is slowly added dropwise 1mol sodium chloroacetates, reacts 2h, obtains lignin
Cation asphalt emulgent, yield 67%.
The lignin quaternary ammonium salt cation asphalt emulsifier of preparation is subjected to FTIR detections after separating-purifying, as a result such as
Under：3340-3510cm-1 is N-H stretching vibration peaks, and 3238-3540cm-1 is O-H stretching vibration absworption peaks, and 2949cm-1 is Asia
The asymmetric stretching vibration absworption peak of methyl, 2837cm-1 are methylene symmetrical stretching vibration absorption peak, 1650-1550cm-1 NH
Flexural vibrations peak, 1648cm-1 are C=O stretching vibration absworption peaks, and 1576cm-1 and the skeletal vibration that 1474cm-1 is phenyl ring are inhaled
Peak is received, 1400cm-1 and 1306cm-1 are O-H in-plane bending vibration absorption peaks, and 1320-1020cm-1 is C-N stretching vibration peaks,
1043cm-1 is Ar-O-C stretching vibration absworption peaks, and 965cm-1,920cm-1 and 864cm-1 are the hydrogen face excurvation isolated on phenyl ring
Bent vibration absorption peak, 616cm-1 are O-H out-of-plane bending vibration absorption peaks.
Reaction equation is as follows：
The preparation of 2 lignin quaternary ammonium salt cation asphalt emulsifier of embodiment
It follows the steps below：
(1) 1mol parahydroxyben-zaldehydes are added in reaction bulb, sequentially add 2mol thionyl chlorides and 8mol triethylamines, room
1.5mol lignin is added after temperature reaction 2-3h, reaction 2h is stirred at room temperature, obtains intermediate I；
(2) intermediate I is dissolved in glacial acetic acid, 30% hydrobromic acids of 2mol is added dropwise, 40-45 DEG C of reaction 2h continuously adds 3mol
3- amino -1- propyl alcohol reacts at room temperature 3h, intermediate II；
(3) intermediate II is dissolved in dichloromethane, 0 DEG C is slowly added dropwise 3mol sodium chloroacetates, reacts 2h, obtains lignin
Cation asphalt emulgent, yield 70%.
The lignin quaternary ammonium salt cation asphalt emulsifier of preparation is subjected to FTIR detections after separating-purifying, is as a result demonstrate,proved
Bright is lignin quaternary ammonium salt cation asphalt emulsifier.
The preparation of 3 lignin quaternary ammonium salt cation asphalt emulsifier of embodiment
It follows the steps below：
(1) 1mol parahydroxyben-zaldehydes are added in reaction bulb, sequentially add 1.5mol thionyl chlorides and 5mol triethylamines,
1.3mol lignin is added after reacting at room temperature 2-3h, reaction 2h is stirred at room temperature, obtains intermediate I；
(2) intermediate I is dissolved in glacial acetic acid, 30% hydrobromic acids of 1.5mol is added dropwise, 40-45 DEG C of reaction 2h is continuously added
2mol 3- amino -1- propyl alcohol reacts at room temperature 3h, intermediate II；
(3) intermediate II is dissolved in dichloromethane, 0 DEG C is slowly added dropwise 2mol sodium chloroacetates, reacts 2h, obtains lignin
Cation asphalt emulgent, yield 82%.
The lignin quaternary ammonium salt cation asphalt emulsifier of preparation is subjected to FTIR detections after separating-purifying, is as a result demonstrate,proved
Bright is lignin quaternary ammonium salt cation asphalt emulsifier.
The preparation of 4 lignin quaternary ammonium salt cation asphalt emulsifier of embodiment
It follows the steps below：
(1) 1mol parahydroxyben-zaldehydes are added in reaction bulb, sequentially add 1.2mol thionyl chlorides and 3mol triethylamines,
1.2mol lignin is added after reacting at room temperature 2-3h, reaction 2h is stirred at room temperature, obtains intermediate I；
(2) intermediate I is dissolved in glacial acetic acid, 30% hydrobromic acids of 1.3mol is added dropwise, 40-45 DEG C of reaction 2h is continuously added
1.5mol 3- amino -1- propyl alcohol reacts at room temperature 3h, intermediate II；
(3) intermediate II is dissolved in dichloromethane, 0 DEG C is slowly added dropwise 1.5mol sodium chloroacetates, reacts 2h, obtains lignin
Cationoid asphalt emulsifier, yield 91%.
The lignin quaternary ammonium salt cation asphalt emulsifier of preparation is subjected to FTIR detections after separating-purifying, is as a result demonstrate,proved
Bright is lignin quaternary ammonium salt cation asphalt emulsifier.
The preparation of 5 emulsified asphalt of embodiment
AH-90# pitch 300g are taken, are heated to 125 DEG C, 9g asphalt emulsifiers manufactured in the present embodiment are added to 200g water
In, it is configured to aqueous solution, is heated to 65-75 DEG C, soap lye is made；By after heating pitch and emulsifier soap lye pass through colloid mill breast
Change, a certain amount of auxiliary agent ammonium chloride is added, prepares cationic emulsified bitumen.
The preparation of 6 emulsified asphalt of embodiment
AH-90# pitch 300g are taken, are heated to 125 DEG C, 9g asphalt emulsifiers manufactured in the present embodiment are added to 200g water
In, it is configured to aqueous solution, is heated to 65-75 DEG C, soap lye is made；By after heating pitch and emulsifier soap lye pass through colloid mill breast
Change, a certain amount of auxiliary agent aluminum sulfate is added, prepares cationic emulsified bitumen.
The preparation of 7 emulsified asphalt of embodiment
AH-90# pitch 300g are taken, are heated to 125 DEG C, 9g asphalt emulsifiers manufactured in the present embodiment are added to 200g water
In, it is configured to aqueous solution, is heated to 65-75 DEG C, soap lye is made；By after heating pitch and emulsifier soap lye pass through colloid mill breast
Change, a certain amount of auxiliary agent calcium chloride is added, prepares cationic emulsified bitumen.
1 each emulsified asphalt of test example breaks performance
Emulsified asphalt made from embodiment 5-7 is pressed into the cationic emulsified bitumen standard (JTJ052- that Chinese transportation portion works out
2000) it is detected, the results are shown in Table 1-3.
1 normal temperature storage stability of table
The general technology performance of 2 each emulsified asphalt of table
| Emulsified asphalt | Viscosity (S) | Bitumen content (%) | Residue (%) on sieve | Attached property is wrapped up in coarse aggregate |
| Embodiment 5 | 38 | 65 | 0.02 | >2/3 |
| Embodiment 6 | 35 | 65 | 0.05 | >2/3 |
| Embodiment 7 | 46 | 61 | 0.03 | >2/3 |
The de-emulsification speed of 3 each emulsified asphalt of table
| Emulsified asphalt | Mix and stir stability |
| Embodiment 5 | It splits soon |
| Embodiment 6 | In split |
| Embodiment 7 | In split |
It can be seen from the above result that the lignin quaternary ammonium salt cation asphalt emulsifier for preparing of the present invention it is emulsifiable it is a variety of not
With the pitch of model, the emulsified asphalt of preparation is fine and smooth uniform, and storage stability is good, suitable for being used to spray, making top dressing
Road surface and penetration type road surface have and split the characteristic that type splits type asphalt emulsifier in soon.Emulsified asphalt properties obtained are equal
The cationic emulsified bitumen standard (JTJ052-2000) of Chinese transportation portion formulation can be met.
Although an embodiment of the present invention has been shown and described, it will be understood by those skilled in the art that：Not
In the case of being detached from the principle of the present invention and objective a variety of change, modification, replacement and modification can be carried out to these embodiments, this
The range of invention is limited by claim and its equivalent.
Claims (10)
1. a kind of lignin cation asphalt emulgent, which is characterized in that its general formula of molecular structure is：
Lignin represents lignin molecule chain.
2. a kind of preparation method of lignin cation asphalt emulgent, which is characterized in that follow the steps below：
(1) by parahydroxyben-zaldehyde, lignin, thionyl chloride and triethylamine hybrid reaction, reaction intermediate I, intermediate are obtained
Ⅰ：
(2) by intermediate I, 3- amino -1- propyl alcohol and hydrobromic acid hybrid reaction, intermediate II is obtained, intermediate II is：
(3) by intermediate II and sodium chloroacetate hybrid reaction, lignin cation asphalt emulgent is obtained；
As long as above step does not influence to prepare, replaceable.
3. preparation method according to claim 2, which is characterized in that the feed proportioning ratio used for：Parahydroxyben-zaldehyde, two
Chlorine sulfoxide, triethylamine, lignin, 3- amino -1- propyl alcohol, hydrobromic acid, sodium chloroacetate molar ratio be 1:(1-2):(2-8):(1-
1.5):(1-2):(1-3):(1-3)。
4. preparation method according to claim 2, which is characterized in that the feed proportioning ratio used for：Parahydroxyben-zaldehyde, two
Chlorine sulfoxide, triethylamine, lignin, 3- amino -1- propyl alcohol, hydrobromic acid, sodium chloroacetate molar ratio be 1:(1-1.5):(2-5):
(1-1.3):(1-1.5):(1-2):(1-2)。
5. preparation method according to claim 2, which is characterized in that the feed proportioning ratio used for：Parahydroxyben-zaldehyde, two
Chlorine sulfoxide, triethylamine, lignin, 3- amino -1- propyl alcohol, hydrobromic acid, sodium chloroacetate molar ratio be 1:1.2:3:1.2:1.3:
1.5:1.5。
6. preparation method according to claim 2, which is characterized in that specifically comprise the following steps：
(1) parahydroxyben-zaldehyde is added in reaction bulb, sequentially adds thionyl chloride and triethylamine, be added after reacting at room temperature 2-3h
Lignin is stirred at room temperature reaction 2h, obtains intermediate I；
(2) intermediate I is dissolved in glacial acetic acid, 30% hydrobromic acid is added dropwise, 40-45 DEG C of reaction 2h continuously adds 3- amino -1- third
Alcohol reacts at room temperature 3h, intermediate II；
(3) intermediate II is dissolved in dichloromethane, 0 DEG C is slowly added dropwise sodium chloroacetate, reacts 2h, obtains the drip of lignin cation
Green emulsifier.
7. according to claim 1 lignin cation asphalt emulgent prepare split soon type and in split type cation emulsified
Application in pitch.
8. a kind of preparation method of emulsified asphalt, which is characterized in that include the following steps：Asphalt emulsification described in claim 1
The dosage of agent is the 1-3% of the emulsified asphalt gross mass prepared, adds water to be configured to aqueous solution above-mentioned asphalt emulsifier, is heated to
65-75 DEG C, soap lye is made；By after heating pitch and emulsifier soap lye emulsified by colloid mill, a certain amount of auxiliary agent is added, make
It is standby go out cationic emulsified bitumen.
9. preparation method according to claim 8, which is characterized in that the auxiliary agent includes aluminum sulfate, ammonium chloride and calcium chloride
One or more of.
10. emulsified asphalt prepared by preparation method according to claim 8.
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| CN111013484A (en) * | 2019-11-25 | 2020-04-17 | 南京科技职业学院 | Alkyl glycoside carboxyl betaine type zwitterionic surfactant and preparation method thereof |
| CN111393673A (en) * | 2020-03-21 | 2020-07-10 | 卢立新 | Novel asphalt emulsifier and preparation method and application thereof |
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