CN104151179A - Dication asphalt emulsifier and preparation method thereof - Google Patents
Dication asphalt emulsifier and preparation method thereof Download PDFInfo
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- CN104151179A CN104151179A CN201410387152.1A CN201410387152A CN104151179A CN 104151179 A CN104151179 A CN 104151179A CN 201410387152 A CN201410387152 A CN 201410387152A CN 104151179 A CN104151179 A CN 104151179A
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Abstract
The invention discloses a dication asphalt emulsifier. The molecular structure of the dication asphalt emulsifier is shown in the description, wherein when x is equal to 1, y is equal to 1 and i is equal to 0; when x is equal to 2, y is equal to 0, z is equal to 1 or 0, and i plus z is equal to 1. The dication asphalt emulsifier is prepared from the following raw material in molar ratio: 1 mol of N-Hydrogenated tallow-1, 3-diaminopropane, 6.00-13.00 mol of alcohols solvent, 1.02-3.05 mol of methyl acrylate, and 2.02-2.10 mol of sodium chloroacetate. The alcohols solvent adopts ethyl alcohol, methyl alcohol or isopropyl alcohol. The synthetic raw material of the dication asphalt emulsifier is easy to get, the production cost is low, the technology is simple, and high-temperature reaction is not required. Different types of asphalt can be emulsified, the prepared asphalt emulsifier is exquisite and uniform, the storage stability is good, dication emulsified asphalt can be prepared, and the dication asphalt emulsifier is applied to spreading of road penetrated oil layers or bonding oil as well as slurry surfacing and micro-surfacing parts, and has the characteristics of a medium breaking asphalt emulsifier and a slow breaking asphalt emulsifier.
Description
Technical field
The present invention relates to a kind of dication type asphalt emulsifier and preparation method thereof, belong to fine chemical technology field.
Background technology
Emulsified bitumen especially cationic emulsified bitumen, owing to having energy-conserving and environment-protective, can improve execution conditions, and can effectively reduce many good application characteristics such as pitch overaging, and is widely used in Road construction and pavement preservation.
The most critical factor that affects emulsified bitumen pavement performance is exactly asphalt emulsifier, and domestic and international cationic asphalt emulsifier principal item has organic amine, quaternary ammonium salt, imidazolines, amides etc. at present, and wherein quaternary ammonium salt emulsifying agent is most widely used general.Along with the application of cationic emulsified bitumen, the kind of asphalt emulsifier is also abundant gradually.
US Patent No. P4338136 is with C
12-18long chain fatty acid reacts under certain condition and prepares asphalt emulsifier with diethylenetriamine.The shortcoming of the method is that the asphalt emulsifier of preparation is expensive, and while constructing for slurry seal, the breakdown of emulsion time is long, and molding time is slow, and the open to traffic time is long.Chinese patent CN1096714 utilizes refinery by-product naphthenic acid to react with alkenyl polyamine, prepares asphalt emulsifier.The shortcoming of the method is that the raw material supply of emulsifying agent is subject to severely restricts, is unfavorable for applying.Chinese patent CN1861721A relates to a kind of rosin cation asphalt emulgent.This emulsifying agent is to be reacted by rosin and alkenyl polyamine, obtains rosin intermediate, then, with dissimilar quaternary ammonium salt intermediate condensation, makes the rosin cation asphalt emulgent of excellent property.The shortcoming of this method is that reactions steps is loaded down with trivial details, needs pyroreaction.Chinese patent CN101712625A relates to a kind of method for synthesizing amphoteric slow-breaking quick-setting asphalt emulsifier, adopts oleic acid to react with polyamines and generates polyamide-polyamino, then adds Mono Chloro Acetic Acid generation halogenating reaction, makes asphalt emulsifier.The shortcoming of the method needs pyroreaction while being preparation.Chinese patent CN101745340A relates to a kind of cation asphalt emulgent preparation method, and host obtains intermediate by the reaction of mixed organic acid and organic amine, then carries out quaterisation and make, and assistant agent is nonionogenic tenside and modified additive.The shortcoming of the method is that preparation process is loaded down with trivial details, and cost is higher, needs pyroreaction.
The ubiquitous deficiency of above-mentioned cationic asphalt emulsifier and preparation method thereof is: the raw materials cost of preparing emulsifying agent is higher, and source is restricted, and needs pyroreaction during preparation, higher to productive experiment equipment requirements.
Summary of the invention
For the deficiencies in the prior art, the object of the present invention is to provide dication type asphalt emulsifier that a kind of production cost is low, technique simply, does not need pyroreaction and preparation method thereof.
For achieving the above object, the present invention adopts following technical scheme:
A dication type asphalt emulsifier, is prepared from by the raw material of following mole of proportioning:
N-hydrogenated-tallow group-1,3-trimethylene diamines: alcoholic solvent: methyl acrylate: sodium chloroacetate=1mol:(6.00-13.00) mol:(1.02-3.05) mol:(2.02-2.10) mol;
Described alcoholic solvent is ethanol, methyl alcohol or Virahol.
The molecular structure of described dication type asphalt emulsifier is:
Wherein, when x=1, y=1, z=1, i=0; When x=2, y=0, z=1 or 0, i+z=1.
The preparation method of this dication type asphalt emulsifier, comprises the following steps:
(1) by N-hydrogenated-tallow group-1,3-trimethylene diamines joins in reaction vessel, adds alcoholic solvent, and heated and stirred is dissolved, then adds methyl acrylate, at 60-80 ℃ of stirring reaction 2-6h, obtains reaction intermediate;
(2) to adding mass concentration in the reaction solution of step (1), be the 25-35% sodium chloroacetate aqueous solution, at 60-80 ℃ of stirring reaction 2-7h, obtain dication type asphalt emulsifier;
In step (1), (2), N-hydrogenated-tallow group-1, the mol ratio of 3-trimethylene diamines, alcoholic solvent, methyl acrylate, sodium chloroacetate is 1:(6.00-13.00): (1.02-3.05): (2.02-2.10);
In step (1), described alcoholic solvent is ethanol, methyl alcohol or Virahol;
In step (2), sodium chloroacetate is made by Mono Chloro Acetic Acid and sodium hydroxide reaction.
Preferably, in step (1), temperature of reaction is 65-75 ℃;
Preferably, in step (2), temperature of reaction is 65-75 ℃.
Dication type asphalt emulsifier prepared by the present invention application in preparing emulsified bitumen, application method is for to be mixed with by dication type asphalt emulsifier the aqueous solution that mass concentration is 1.0-3.0%, with salt acid for adjusting pH value, to 2-3, be heated to 65 ℃, make soap lye; Pitch and emulsifying agent soap lye are prepared to cationic emulsified bitumen by colloidal mill emulsification.
The present invention has following beneficial effect with respect to prior art:
(1) raw material N-hydrogenated-tallow group-1 of dication type asphalt emulsifier of the present invention, 3-trimethylene diamines is cheap with respect to current cationic asphalt emulsifier raw material used, wide material sources, and asphalt emulsifier production cost is low.
(2) preparation method's technique of dication type asphalt emulsifier of the present invention simply, does not need pyroreaction.
(3) the dication type asphalt emulsifier that prepared by the present invention can the multiple different model of emulsification pitch, the emulsified bitumen of preparation is evenly fine and smooth, stability in storage is good, be applicable to spread and slurry seal and micro-table place of highway priming oil or sticking layer oil, in having, split and split slowly the characteristic of asphalt emulsifier.The emulsified bitumen properties making all can meet the cationic emulsified bitumen standard (JTJ052-2000) that Chinese transportation portion works out.
(4) in raw material of the present invention by adding sodium chloroacetate, make preparation asphalt emulsification agent molecule there is dication type, strengthened the electric charge intensity of asphalt emulsification agent molecule.
Embodiment
The present invention is further illustrated in conjunction with the embodiments, should be noted that following explanation is only in order to explain the present invention, does not limit its content.
In the embodiment of the present invention, raw material used, reagent are conventional chemical product, all can be bought and be obtained by market.
Embodiment 1
(1) preparation of dication type asphalt emulsifier:
1) in reactor, add 326g N-hydrogenated-tallow group-1,3-trimethylene diamines, 400g Virahol, heated and stirred is dissolved.Then drip 90.3g methyl acrylate, 70 ℃ of stirring reaction 4h, obtain reaction intermediate.
The reaction intermediate obtaining is carried out after recrystallization separating-purifying to FTIR detection, result is as follows: 3275cm
-1for N-H stretching vibration absorption peak, 2917cm
-1and 2854cm
-1be respectively asymmetric stretching vibration and the symmetrical stretching vibration absorption peak of methylene radical, 1735cm
-1for ester group C=O stretching vibration absorption peak, 1569cm
-1for the flexural vibration absorption peak of N-H, 1470cm
-1for methylene radical scissoring vibration absorption peak, 1376cm
-1for methyl symmetric curvature vibration absorption peak, 1207cm
-1for C-N stretching vibration absorption peak, 1125cm
-1for C-O-C stretching vibration absorption peak, 724cm
-1for methylene radical rocking vibration absorption peak.
2) 83.2g sodium hydroxide is dissolved in 160.0g water and obtains aqueous sodium hydroxide solution, 196.6g Mono Chloro Acetic Acid is dissolved in and in 400.0g water, obtains the Mono Chloro Acetic Acid aqueous solution; Aqueous sodium hydroxide solution is added drop-wise to and in the Mono Chloro Acetic Acid aqueous solution, obtains the sodium chloroacetate aqueous solution.The sodium chloroacetate aqueous solution of preparation is added drop-wise to above-mentioned steps 1) in synthetic product, 65 ℃ of stirring reaction 5h.Obtain dication type asphalt emulsifier, give over to emulsified bitumen test.
Synthetic product after recrystallization separating-purifying, carry out FTIR and
1h NMR detects, and result is as follows: FTIR:3250-3500cm
-1for stretching vibration and the N-H stretching vibration absorption stack peak of O-H, 2918cm
-1and 2846cm
-1be respectively asymmetric stretching vibration and the symmetrical stretching vibration absorption peak of methylene radical, 1737cm
-1for C=O stretching vibration absorption peak in carboxylic acid, 1634cm
-1for C=O stretching vibration absorption peak in carboxylate salt, 1470cm
-1for methylene radical scissoring vibration absorption peak, 1395cm
-1for methyl symmetric curvature vibration absorption peak, 1207cm
-1for C-N stretching vibration absorption peak, 1068cm
-1for C-OH stretching vibration absorption peak, 926cm
-1for the wagging vibration absorption peak of O-H in carboxylic acid, 717cm
-1for methylene radical rocking vibration absorption peak.
1H NMR(300MHz,D
2O),δ:0.81(t,3H,-CH
3),1.22(s,30H,-CH
2-),1.66(s,2H,CH
3(CH
2)
15C
H 2-),2.16(s,2H,-NH
+CH
2C
H 2CH
2NH
+-),2.59(m,2H,-NH
+CH
2C
H 2COOH),3.12-3.67(m,8H,-C
H 2NH
+C
H 2CH
2C
H 2NH
+C
H 2CH
2COOH),3.73-4.24(m,4H,-C
H 2COONa)ppm。
Reaction equation is as follows:
C
18H
37NH(CH
2)
3NH
2+CH
2＝CHCOOCH
3→C
18H
37NH(CH
2)
3NH(CH
2)
2COOCH
3 (1)
(2) preparation of emulsified bitumen:
Get AH-90# pitch 300g, be heated to 125 ℃, asphalt emulsifier prepared by 12.5g the present embodiment joins in 200g water, with technical hydrochloric acid, regulates pH value to 2-3, is heated to 65 ℃, makes soap lye.Pitch and emulsifying agent soap lye are prepared to cationic emulsified bitumen by colloidal mill emulsification.
(3) emulsified bitumen Performance Detection:
The cationic emulsified bitumen standard (JTJ052-2000) that the emulsified bitumen making is worked out by Chinese transportation portion detects, result is as follows: emulsified bitumen prepared by the present embodiment is even, fine and smooth, asphalt content is 59%, on sieve, residual content is 0.02%, wrap area with mineral aggregate and be greater than 2/3, stability in storage (5d) is 3.5%; In de-emulsification speed test, adopt category-B material, can be 12 seconds the mixing time.Show that bitumen emulsion prepared by this emulsifying agent splits type cationic emulsified bitumen in being, properties all can meet the requirement of JTJ052-2000 standard.
Embodiment 2
(1) preparation of dication type asphalt emulsifier:
1) in reactor, add 326g N-hydrogenated-tallow group-1,3-trimethylene diamines, 400g Virahol, heated and stirred is dissolved.Then drip 175.5g methyl acrylate, 75 ℃ of stirring reaction 3h, obtain reaction intermediate.
2) 83.2g sodium hydroxide is dissolved in 160.0g water and obtains aqueous sodium hydroxide solution, 196.6g Mono Chloro Acetic Acid is dissolved in and in 400.0g water, obtains the Mono Chloro Acetic Acid aqueous solution; Aqueous sodium hydroxide solution is added drop-wise to and in the Mono Chloro Acetic Acid aqueous solution, obtains the sodium chloroacetate aqueous solution.The sodium chloroacetate aqueous solution of preparation is added drop-wise to above-mentioned steps 1) in synthetic product, 75 ℃ of stirring reaction 3h.Obtain dication type asphalt emulsifier, give over to emulsified bitumen test.
Synthetic product after recrystallization separating-purifying, carry out FTIR and
1h NMR detects, and result is as follows: FTIR:3250-3500cm
-1for stretching vibration and the N-H stretching vibration absorption stack peak of O-H, 2925cm
-1and 2850cm
-1be respectively asymmetric stretching vibration and the symmetrical stretching vibration absorption peak of methylene radical, 1735cm
-1for C=O stretching vibration absorption peak in carboxylic acid, 1605cm
-1for C=O stretching vibration absorption peak in carboxylate salt, 1470cm
-1for methylene radical scissoring vibration absorption peak, 1395cm
-1for methyl symmetric curvature vibration absorption peak, 1254cm
-1for C-N stretching vibration absorption peak, 1068cm
-1for C-OH stretching vibration absorption peak, 917cm
-1for the wagging vibration absorption peak of O-H in carboxylic acid, 701cm
-1for methylene radical rocking vibration absorption peak.
1H NMR(300MHz,D
2O),δ:0.85(t,3H,-CH
3),1.26(s,30H,-CH
2-),1.70(s,2H,CH
3(CH
2)
15C
H 2-),2.24(s,2H,-NH
+CH
2C
H 2CH
2N
+-),2.57-2.64(m,4H,-CH
2C
H 2COOH),3.01-3.58(m,10H,-C
H 2NH
+C
H 2CH
2C
H 2N
+(C
H 2CH
2COOH)
2),3.83-4.28(s,4H,-C
H 2COONa)ppm。
Reaction equation is as follows:
C
18H
37NH(CH
2)
3NH
2+2CH
2＝CHCOOCH
3→C
18H
37NH(CH
2)
3N(CH
2CH
2COOCH
3)
2 (3)
(2) preparation of emulsified bitumen:
Get AH-90# pitch 300g, be heated to 125 ℃, asphalt emulsifier prepared by 12.5g the present embodiment joins in 200g water, with technical hydrochloric acid, regulates pH value to 2-3, is heated to 65 ℃, makes soap lye.Pitch and emulsifying agent soap lye are prepared to cationic emulsified bitumen by colloidal mill emulsification.
(3) emulsified bitumen Performance Detection:
Detection method is with embodiment 1, and detected result is: emulsified bitumen is even, fine and smooth, and asphalt content is 60%, and on sieve, residual content is 0.03%, wraps area be greater than 2/3 with mineral aggregate, and stability in storage (5d) is 3.4%; In de-emulsification speed test, adopt category-B material, can be 47 seconds the mixing time.Show that bitumen emulsion prepared by this emulsifying agent is for splitting slowly type cationic emulsified bitumen, properties all can meet the requirement of JTJ052-2000 standard.
Embodiment 3
(1) preparation of dication type asphalt emulsifier:
1) in reactor, add 326g N-hydrogenated-tallow group-1,3-trimethylene diamines, 400g Virahol, heated and stirred is dissolved.Then drip 261.6g methyl acrylate, 70 ℃ of stirring reaction 4h, obtain reaction intermediate.
2) 83.2g sodium hydroxide is dissolved in 160.0g water and obtains aqueous sodium hydroxide solution, 196.6g Mono Chloro Acetic Acid is dissolved in and in 400.0g water, obtains the Mono Chloro Acetic Acid aqueous solution; Aqueous sodium hydroxide solution is added drop-wise to and in the Mono Chloro Acetic Acid aqueous solution, obtains the sodium chloroacetate aqueous solution.The sodium chloroacetate aqueous solution of preparation is added drop-wise to above-mentioned steps 1) in synthetic product, 60 ℃ of stirring reaction 7h.Obtain dication type asphalt emulsifier, give over to emulsified bitumen test.
Synthetic product after recrystallization separating-purifying, carry out FTIR and
1h NMR detects, and result is as follows: FTIR:3427cm
-1for the stretching vibration absorption peak of O-H, 2925cm
-1and 2854cm
-1be respectively asymmetric stretching vibration and the symmetrical stretching vibration absorption peak of methylene radical, 1733cm
-1for C=O stretching vibration absorption peak in carboxylic acid, 1606cm
-1for C=O stretching vibration absorption peak in carboxylate salt, 1463cm
-1for methylene radical scissoring vibration absorption peak, 1395cm
-1for methyl symmetric curvature vibration absorption peak, 1261cm
-1and 1197cm
-1for C-N stretching vibration absorption peak, 1072cm
-1for C-OH stretching vibration absorption peak, 930cm
-1for the wagging vibration absorption peak of O-H in carboxylic acid, 772cm
-1for methylene radical rocking vibration absorption peak.
1H NMR(300MHz,D
2O),δ:0.85(t,3H,-CH
3),1.25(s,30H,-CH
2-),1.70(s,2H,CH
3(CH
2)
15C
H 2-),2.24(s,2H,-N
+CH
2C
H 2CH
2N
+-),2.63-2.85(m,6H,-CH
2C
H 2COOH),2.93-3.51(m,12H,-C
H 2N
+(C
H 2CH
2COOH)-C
H 2CH
2C
H 2N
+(C
H 2CH
2COOH)
2),3.89-4.25(s,4H,-C
H 2COONa)ppm。
Reaction equation is as follows:
(2) preparation of emulsified bitumen:
Get AH-90# pitch 300g, be heated to 125 ℃, asphalt emulsifier prepared by 12.5g the present embodiment joins in 200g water, with technical hydrochloric acid, regulates pH value to 2-3, is heated to 65 ℃, makes soap lye.Pitch and emulsifying agent soap lye are prepared to cationic emulsified bitumen by colloidal mill emulsification.
(3) emulsified bitumen Performance Detection:
Detection method is with embodiment 1, and detected result is: emulsified bitumen is even, fine and smooth, and asphalt content is 59%, and on sieve, residual content is 0.03%, wraps area be greater than 2/3 with mineral aggregate, and stability in storage (5d) is 4.1%; In de-emulsification speed test, adopt category-B material, can be 14 seconds the mixing time.Show that bitumen emulsion prepared by this emulsifying agent splits type cationic emulsified bitumen in being, properties all can meet the requirement of JTJ052-2000 standard.
Above-described embodiment is preferably embodiment of the present invention; but embodiments of the present invention are not restricted to the described embodiments; one of ordinary skill in the art should be understood that; on the basis of technical scheme of the present invention, those skilled in the art do not need to pay various modifications that creative work can make or distortion still in protection scope of the present invention.
Claims (10)
1. a dication type asphalt emulsifier, is characterized in that, the molecular structure of described dication type asphalt emulsifier is:
Wherein, when x=1, y=1, z=1, i=0; When x=2, y=0, z=1 or 0, i+z=1.
2. a kind of dication type asphalt emulsifier as claimed in claim 1, is characterized in that, by the raw material of following mole of proportioning, is prepared from:
N-hydrogenated-tallow group-1,3-trimethylene diamines: alcoholic solvent: methyl acrylate: sodium chloroacetate=1mol:(6.00-13.00) mol:(1.02-3.05) mol:(2.02-2.10) mol;
Described alcoholic solvent is ethanol, methyl alcohol or Virahol.
3. the preparation method of the dication type asphalt emulsifier described in claim 1 or 2, is characterized in that, comprises the following steps:
(1) by N-hydrogenated-tallow group-1,3-trimethylene diamines joins in reaction vessel, adds alcoholic solvent, dissolves, then adds methyl acrylate, at 60-80 ℃ of reaction 2-6h, obtains reaction intermediate;
(2) to adding mass concentration in the reaction solution of step (1), be the 25-35% sodium chloroacetate aqueous solution, at 60-80 ℃ of reaction 2-7h, obtain dication type asphalt emulsifier;
In step (1), (2), N-hydrogenated-tallow group-1, the mol ratio of 3-trimethylene diamines, alcoholic solvent, methyl acrylate, sodium chloroacetate is 1:(6.00-13.00): (1.02-3.05): (2.02-2.10).
4. the preparation method of dication type asphalt emulsifier as claimed in claim 3, is characterized in that, in step (1), temperature of reaction is 65-75 ℃.
5. the preparation method of dication type asphalt emulsifier as claimed in claim 3, is characterized in that, in step (2), temperature of reaction is 65-75 ℃.
6. the preparation method of dication type asphalt emulsifier as claimed in claim 3, is characterized in that, in step (2), sodium chloroacetate is made by Mono Chloro Acetic Acid and sodium hydroxide reaction.
7. the preparation method of dication type asphalt emulsifier as claimed in claim 3, is characterized in that, concrete steps are as follows:
(1) by 326g N-hydrogenated-tallow group-1,3-trimethylene diamines, 400g Virahol, heated and stirred is dissolved, and then drips 90.3g methyl acrylate, and 70 ℃ of stirring reaction 4h, obtain reaction intermediate;
(2) 83.2g sodium hydroxide is dissolved in 160.0g water and obtains aqueous sodium hydroxide solution, 196.6g Mono Chloro Acetic Acid is dissolved in and in 400.0g water, obtains the Mono Chloro Acetic Acid aqueous solution; Aqueous sodium hydroxide solution is added drop-wise to and in the Mono Chloro Acetic Acid aqueous solution, obtains the sodium chloroacetate aqueous solution; The sodium chloroacetate aqueous solution of preparation is added drop-wise in above-mentioned steps (1) synthetic product, and 65 ℃ of stirring reaction 5h, obtain dication type asphalt emulsifier.
8. the preparation method of dication type asphalt emulsifier as claimed in claim 3, is characterized in that, concrete steps are as follows:
(1) by 326g N-hydrogenated-tallow group-1,3-trimethylene diamines, 400g Virahol, heated and stirred is dissolved, and then drips 175.5g methyl acrylate, and 75 ℃ of stirring reaction 3h, obtain reaction intermediate;
(2) 83.2g sodium hydroxide is dissolved in 160.0g water and obtains aqueous sodium hydroxide solution, 196.6g Mono Chloro Acetic Acid is dissolved in and in 400.0g water, obtains the Mono Chloro Acetic Acid aqueous solution; Aqueous sodium hydroxide solution is added drop-wise in the Mono Chloro Acetic Acid aqueous solution and obtains the sodium chloroacetate aqueous solution, the sodium chloroacetate aqueous solution of preparation is added drop-wise in above-mentioned steps (1) synthetic product, 75 ℃ of stirring reaction 3h, obtain dication type asphalt emulsifier.
9. the preparation method of dication type asphalt emulsifier as claimed in claim 3, is characterized in that, concrete steps are as follows:
(1) by 326g N-hydrogenated-tallow group-1,3-trimethylene diamines, 400g Virahol, heated and stirred is dissolved, and then drips 261.6g methyl acrylate, and 70 ℃ of stirring reaction 4h, obtain reaction intermediate;
(2) 83.2g sodium hydroxide is dissolved in 160.0g water and obtains aqueous sodium hydroxide solution, 196.6g Mono Chloro Acetic Acid is dissolved in and in 400.0g water, obtains the Mono Chloro Acetic Acid aqueous solution; Aqueous sodium hydroxide solution is added drop-wise in the Mono Chloro Acetic Acid aqueous solution and obtains the sodium chloroacetate aqueous solution, the sodium chloroacetate aqueous solution of preparation is added drop-wise in above-mentioned steps (1) synthetic product to 60 ℃ of stirring reaction 7h.Obtain dication type asphalt emulsifier.
10. the application of the dication type asphalt emulsifier described in claim 1 or 2 in preparing emulsified bitumen, it is characterized in that, application method is for to be mixed with by dication type asphalt emulsifier the aqueous solution that mass concentration is 1.0-3.0%, with salt acid for adjusting pH value to 2-3, be heated to 65 ℃, make soap lye; Pitch and emulsifying agent soap lye are prepared to cationic emulsified bitumen by colloidal mill emulsification.
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| CN105384948A (en) * | 2015-12-21 | 2016-03-09 | 山东大学 | Dication and dianion type asphalt emulsifier and preparation method thereof |
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| CN106995393A (en) * | 2017-04-13 | 2017-08-01 | 山东大学 | A kind of double quaternary ammonium salt type hydroxypropyl azochlorosulfonate acid sodium asphalt emulsifier and preparation method thereof |
| CN107383391A (en) * | 2017-04-13 | 2017-11-24 | 山东大学 | A kind of secondary amide double quaternary ammonium salt type hydroxypropyl azochlorosulfonate acid sodium asphalt emulsifier and preparation method thereof |
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