WO2013036095A1 - Amidoamine compounds, modified asphalts, warm mixtures, methods for the production thereof and the use thereof - Google Patents

Amidoamine compounds, modified asphalts, warm mixtures, methods for the production thereof and the use thereof Download PDF

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Publication number
WO2013036095A1
WO2013036095A1 PCT/MX2011/000133 MX2011000133W WO2013036095A1 WO 2013036095 A1 WO2013036095 A1 WO 2013036095A1 MX 2011000133 W MX2011000133 W MX 2011000133W WO 2013036095 A1 WO2013036095 A1 WO 2013036095A1
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Prior art keywords
asphalt
percentage
formula
amidoamine compound
modified
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PCT/MX2011/000133
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Spanish (es)
French (fr)
Inventor
Tetsuya OGURA FUJI
Ignacio CREMADES IBAÑEZ
Arlette Yavel MARTINEZ CHAVEZ
Pedro LIMON COVARRUBIAS
Israel SANDOVAL NAVARRO
Paula Cristina ARROYO MARTINEZ
Mario BARROSO FRAGOSO
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Surfax S.A. De C.V.
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Publication of WO2013036095A1 publication Critical patent/WO2013036095A1/en

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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
    • C08K5/20—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Definitions

  • the present invention relates to the technical field of the construction of land roads and modified asphalts.
  • Asphalt paving mixtures are composed of asphalt and stone aggregate.
  • the asphalt must be sufficiently fluid to coat the stone aggregate and that the asphalt mixture is easily applicable in paving. Therefore, it is necessary to reduce the viscosity of the asphalt and increase its workability through a heating process.
  • Conventional methods for producing mixtures for paving and paving require temperatures between 160 ° C and 1SHFC. Asphalt mixtures made at these temperatures are called hot asphalt mixes or HMA (Hot Max Asphaft).
  • Hot mixes offer, in general, good results in terms of the handling and operation of asphalt. However, they have adverse effects on the environment, workers' health, energy consumption and premature asphalt aging, due to high temperatures. FOT e
  • empto, heating asphalt requires large amounts of energy, which is commonly obtained from fossil fuels, which generate a large carotid! tie toxic gases and greenhouse gases such as CO 2 -
  • Adidonamentente there are cold mixtures that are based on emuEs ⁇ cwtes asf f [£ ficas that do not require high temperatures, but present other problems, poca the low adhesion between the stone aggregate and the asphalt due to the presence of water, hs sipas diffitnulta la compaction
  • This type of mixtures is ait ⁇ Gza peco and prim ainTBetratte rare trifinrasas 9mss.
  • a viable alternative to hot mixes is warm mixes or WEV Warm Mix Asphalt). In warm mixtures, asphalt heats at lower temperatures than in hot mixtures. The mixing and laying temperatures of the warm mixtures is between approximately 95 ° C and 140 ° C.
  • Warm mixes offer several advantages over hot mixes, such as; considerable energy savings during heating, the decrease of gaseous emissions into the atmosphere from the burning of fuel, such as greenhouse gases, volatile organic compounds (VOCs) and unpleasant odors.
  • VOCs volatile organic compounds
  • Warm mixtures allow cost savings for insulation in asphalt plants and extend the range of application and compaction ambient temperature of the asphalt mixture. Warm mixes are compatible with the most common folder designs on the market such as SUPE PAVE and Marshall.
  • Warm mixes offer many advantages over hot mixes or cold mixes, the only difficulty they present is related to the viscosity of asphalt.
  • the viscosity of the asphalt is higher at temperatures of warm mixtures, so that sometimes, the total coating of the stone aggregate is prevented and its application is difficult during mixing, laying and compaction.
  • Sasobit ® United States
  • Asphattan ® Rosobit ®
  • Asphaftan 18 is a low molecular weight steric resin that is presented in granular form. Both are used in a percentage between 2 and 4% on the weight of the mixture.
  • foaming such as Aspha-min (Eurovia Services of Bottrop, Germany), which is synthetic zeolite orna with sodium aiuminosilicate and that is hydrothermally crystallized, has a water content of approximately twenty%. With heat, water escapes from the structure of the zeolite and causes an expansion in volume of the asphalt by foaming.
  • Aspha-min Eurovia Services of Bottrop, Germany
  • the present invention solves the problem described here because its main functions are:
  • the present invention relates to amidoamine compounds, which have properties such as modifying the viscosity of the asphalt, promoting the adhesion of the asphalt with the stone aggregate, maintaining the mechanical properties of the asphalt mixture and preventing the aging of the asphalt in warm mixtures used for paving.
  • the present invention also provides modified asphalts, asphalt mixtures and their use.
  • the amidoamine compound of the present invention is obtained from the reaction between bis-hexamethylenetriamine and glyceryl triestearate, obtaining the corresponding amidoamine and comprising in its structure a free secondary amino group.
  • This amidoamine compound may or may not be purified for use in asphalt and asphalt paving mixtures.
  • modified asphalts those asphalts that are mixed with polymers to change their theological and mechanical properties, in this case, it should be understood as Modified Asphalt, the asphalt that has been added with the amidoamine compound of The present invention, whether purified or unpurified.
  • the reaction between bis-hexamethylenetriamine and glyceryl stearate is a sterically hindered reaction.
  • the primary amines of the polyamine ends react, first of all with the carboxyl group of the triglyceride, and an amidoamine product is formed with a free secondary amine inside the molecule. If the reaction is prolonged, the free secondary amines will continue to react.
  • reaction order mentioned in the present invention is contrary to that normally reported, because secondary amines are more reactive than primary amines and therefore react first.
  • the spherical impediment causes the primary amines and then the secondary amines to react first. This reaction order is preserved when the appropriate reaction conditions in time and temperature are propitiated.
  • the amidoamine compound is manufactured as follows:
  • BHMT bis-hexamethylenetriamine
  • glyceryl triestearate are mixed in a stoichiometric, sub-stoichiometric and over-stoichiometric ratio.
  • the mixture is heated for 2 to 6 hours at a temperature from 150 ° C to 220 ° C, to carry out the reaction between the reagents.
  • Heating is stopped until an ambient temperature is achieved, to stop the reaction.
  • the preferred stoichiometric ratio is 3 bis-hexamethylenetriamine: 2 glyceryl triestearate.
  • the reaction yield can be calculated by determining the total amine index, secondary amine index and primary amine index, at the beginning and at the end of the reaction. Of total Da amina, 66.6% corresponds to primary amine and 33.3% corresponds to secondary amine. Thus, according to the consumption of the primary amine, the reaction yield can be calculated. It may be the case where the secondary amine is consumed and if so, it is also taken into account to calculate the reaction yield.
  • the amine index is measured in milligrams (mg) of potassium hydroxide (KOH) per gram (g) of sample.
  • the reaction can be followed by FT-IR (Fourier transform infrared spectrometry) at different reaction times and observe the disappearance of the bands corresponding to the carbonyl groups of glyceryl triestearate and observe the appearance of the bands corresponding to the amide groups of the reaction product.
  • FT-IR Fastier transform infrared spectrometry
  • the present invention can be purified by methods known as a) Formation of amine salt, b) Chromatography, c) Column chromatography, etc.
  • the product resulting from the previous reaction may or may not be purified and in both forms the amidoamine compound retains its properties and is used to modify asphalts and in warm paving mixtures.
  • the presentation of the amidoamine compound of the present invention may be in known forms such as: a) Pellets, b) Flakes, c) Emulsions, d) Solutions , etc.
  • the amidoamine compound of the present invention solves the problem of difficult handling of asphalt at warm mixing temperatures. This product has a unique behavior, since it reduces the viscosity of the asphalt between 97 ° C and 140 ° C and increases the viscosity of the asphalt below 97 ° C, as observed in Sa Figure 3.
  • the amidoamine compound of the present invention promotes adhesion between stone aggregate and asphalt, maintains the mechanical properties of the asphalt mixture and prevents asphalt aging.
  • the present invention provides amidoamine compounds, the manufacturing process and its use, modified asphalts and asphalt paving mixtures.
  • the modified asphalt comprises a) Asphalt and b) The amidoamine compound of the present invention of the formula (I) from 1% and up to 6% with respect to asphalt weight.
  • the asphalt mixture comprises a) Modified asphalt with the amidoamine compound of the present invention of the chemical formula (I) from 3.5% to 8%, b) Stone aggregate from 92% and up to 96.5%.
  • the percentages of stone aggregate and modified asphalt in asphalt mixtures are standard percentages and may vary according to the needs of the mixture design.
  • the asphalts modified with the amidoamine compound of the present invention are manufactured as follows:
  • Asphalt mixtures with modified asphalt with the amidoamine compound of the present invention are manufactured as follows:
  • modified asphalt is heated to a temperature between 90 ° C and 140 ° C.
  • a mixture is made with stone aggregate where the final percentage of the components a) Modified asphalt is from 3.5% and up to 8% and b) Stone aggregate is from 92% and up to 96.5%.
  • the amidoamine compound of the present invention increases the viscosity of the asphalt at room temperature of the pavement. Asphalt remains solid and asphalt paving mix retains its mechanical properties (Figure 3).
  • the amidoamine compound of the present invention significantly increases the adhesion between the stone aggregate and the asphalt, due to its chemical structure, which, as is known, the amides increase the adhesion between the asphalt and two minerals (Table 2).
  • the amidoamine compound of the present invention maintains the resilience modulus of the asphalt mixture ( Figure 5).
  • the amidoamine compound of the present invention retains the PG grade (performance grade) of the asphalt after an aging period (Table 7).
  • Figure 1 is the electrospray ionization (ESI-MS) mass spectrum of the purified amidoamine compound obtained from the reaction of glyceryl triestearate and bis-hexamethylenetriamine.
  • Figure 2 is the FT-IR spectrum showing the progress of the reaction to obtain the amidoamine compound of the present invention. The formation of the amidoamine compound is observed.
  • Figure 3 is the graph showing how the viscosity of asphalt is modified when it is added with the unpurified amidoamine compound of Oa present invention.
  • the viscosity decreases by up to 30%, in a range between 97 ° C and 140 ° C, and increases up to 36% below 97 ° C with respect to the target.
  • Figure 4 is the graph showing the penetration of asphalt at 25 ° C, which decreases when the asphalt is modified with the unpurified amidoamine compound of the present invention.
  • Figure 5 is the graph showing that the resilience module is preserved at different compaction temperatures, when the asphalt binder is prepared with asphalt for warm mixtures modified with the amidoamine compound of the present invention.
  • Modified Asphalt the asphalt that has been added with the amidoamine compound of the present invention, whether the amidoamine compound is purified or unpurified.
  • Example 1 Preparation and evaluation of a Target, to note the properties of the amidoamine compound of the present invention and the characteristics of the modified asphalt and the asphalt mixture prepared with modified asphalt.
  • Virgin AC-20 Salamanca asphalt was used as a blank, to evaluate its characteristics. The viscosity, the penetration percentage, its Theological properties were evaluated; PG, Failure Temperature, Rheological Module and Phase Angle, the percentage of friction detachment and the conservation of the resilience module. As follows:
  • the penetration presented by the target is considered normal, for a virgin AC-20 Salamanca asphalt and can be seen graphically in Figure 4.
  • Theological parameters of asphalt describe its behavior under certain test conditions. Parameters such as G * / sen6 that offer a approximation of the resistance presented by the asphalt to be permanently deformed and ⁇ that describes the visco-elasticity of the asphalt.
  • the PG grade shows the behavior of the asphalt when subjected to an aging process, a significant increase in this parameter indicates that the asphalt hardened too much.
  • Rheological module G * / sen5; parameter by which the resistance to permanent asphalt deformation is measured.
  • Phase Angle expresses the visco-elasticity of asphalt.
  • the percentage of friction detachment is characteristic of a virgin asphalt, without additives that promote adhesion, since the asphalt has little affinity for the stone aggregate.
  • the amplitude is considered as the difference between the maximum value that the resilience module takes and the minimum value that it takes and shows the size of the range in which the values are found.
  • Table 5 shows that the white resilience module decreases as the compaction temperature decreases, having an amplitude between the results of 826 and can be seen graphically in Figure 5.
  • Example 2. Manufacture of amidoamine compound.
  • the amidoamine compound was prepared as follows:
  • BHMT bis-hexamethylenetriamine
  • glyceryl triestearate were mixed in a stoichiometry ratio of 3: 2, in a two-mouth ball flask.
  • the mixture was heated at reflux, for 4 hours at a temperature of 180 ° C, to carry out the reaction between the reagents.
  • the total amine index, before starting the reaction was 156 mg KOH per gram of sample.
  • the secondary amine index of the reaction product was 48 milligrams (mg) of potassium hydroxide (KOH) and has a primary amine index of two, which shows that the reaction is carried out by the primary amines of ios , leaving a free secondary amino group in the molecule.
  • the reaction yield was 90%.
  • the amine index was determined by volumetry with Metrohm automatic titrator model 888 Tritiando.
  • the reaction product was purified by forming its amine salt for characterization.
  • the amidoamine compound the result of this reaction has a melting temperature of 118 ° C, is soluble in iso-propanol and insoluble in water and was characterized by elecrospray mass spectrometry (ESl-MS).
  • ESl-MS elecrospray mass spectrometry
  • the reaction was monitored by FT-IR, at zero time and after two and three hours. During the progress of the FT-IR reaction, the disappearance of the representative peak of the triglyceride carbonyl groups was observed in 1737 cnrf and the appearance of the representative amide peak at 1634 cm 1 ( Figure 2).
  • Example 3 Asphalt modified with the amidoamine product.
  • Asphalt AC-20 Salamanca was heated to a temperature of 140 ° C, until it reached a homogeneous temperature.
  • the target has viscosities of 4118cp and 1962cp at 100 ° C and 110 ° C respectively, and in the modified asphalt the viscosities decrease to 2976cp and 1357cp respectively, which is equivalent to a reduction in viscosity of 38% and 44% at IOCTC and 110 ° C respectively.
  • Example 5 Evaluation of the rheological properties of modified asphalt.
  • the PG remains constant after the aging process, unlike the white, in which the PG changes from 64 to 70. This indicates that the modified asphalt hardens less than white, which makes it a younger asphalt and retains its rheological properties over time.
  • the results of rheological module and phase angle indicate that the modified asphalt hardens less than the target. This is reflected in the fault temperature, from which it is concluded that the modified asphalt has a lower tendency to aging.
  • Example 6 Preparation of an asphalt mixture prepared with modified asphalt with the amidoamine compound of the present invention.
  • the asphalt mix was prepared according to the high performance dense granulometry asphalt mix design of the AMAAC PA-A-001/2008 protocol.
  • Example 7 Evaluation of the percentage of friction detachment in asphalt mixture.
  • the percentage of friction detachment obtained with the modified asphalt is 0.1% for stone aggregate with regular adhesion and 3.1% for stone aggregate with poor adhesion, on the white the friction detachment percentages are 15.7% and 55.5% respectively as shown in Table 8. From the foregoing, it is concluded that the amidoamine compound of the present invention behaves as an adhesion promoter between the stone aggregate and the asphalt. Example 8. Evaluation of the conservation of the resilience module of Da asphalt mixture prepared with modified asphalt.
  • Table 9 shows that the amplitude between the resilience modules measured for the asphalt mixture prepared with modified asphalt is significantly less than the amplitude of the resilience modules measured for a white asphalt mixture. Therefore, it is said that the asphalt mixture prepared with modified asphalt preserves the modulus of resilience at different mixing and compaction temperatures, and therefore its mechanical properties are preserved.
  • Figure 5 graphically shows the conservation of the resilience module.

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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Abstract

An amidoamine compound that has properties such as modifying the viscosity of asphalt, promoting adhesion between asphalt and stone aggregate, maintaining the mechanical properties of the asphalt mixture and preventing ageing of the asphalt for warm mixtures used in paving. Method for obtaining the amidoamine compound, a modified asphalt and an asphalt mixture, and the use thereof in warm mixtures for paving.

Description

COMPUESTOS DE AMIDOAMINA, ASFALTOS  AMIDOAMINE COMPOUNDS, ASPHALTS
MODIFICADOS. MEZCLAS TIBIAS, SUS PROCESOS DE  MODIFIED TIBIAS BLENDS, ITS PROCESSES OF
FABRICACIÓN Y USO MANUFACTURE AND USE
CAMPO TÉCNICO DE LA INVENCION TECHNICAL FIELD OF THE INVENTION
La presente invención se relaciona con el campo técnico de la construcción de vías terrestres y asfaltos modificados. The present invention relates to the technical field of the construction of land roads and modified asphalts.
ANTECEDENTES DE LA INVENCIÓN  BACKGROUND OF THE INVENTION
Es bien sabido que el asfalto se utiliza en mezclas asfálticas para pavimentación. Las mezclas asfálticas para pavimentación están compuestas de asfalto y agregado pétreo. El asfalto debe estar lo suficientemente fluido para recubrir al agregado pétreo y que la mezcla asfáltica sea fácilmente aplicable en la pavimentación. Por Eo> que es necesario disminuir la viscosidad del asfalto y aumentar su manejabilidad medíante un proceso de calentamiento. Los métodos convencionales para producir mezclas para pavimentación y pavimentar requieren temperaturas de entre 160°C y 1SHFC. Las mezclas asfálticas realizadas a estas temperaturas reciben el nombre de mrtezclas asfálticas en caliente o HMA (Hot Míx Asphaft). It is well known that asphalt is used in asphalt paving mixtures. Asphalt paving mixtures are composed of asphalt and stone aggregate. The asphalt must be sufficiently fluid to coat the stone aggregate and that the asphalt mixture is easily applicable in paving. Therefore, it is necessary to reduce the viscosity of the asphalt and increase its workability through a heating process. Conventional methods for producing mixtures for paving and paving require temperatures between 160 ° C and 1SHFC. Asphalt mixtures made at these temperatures are called hot asphalt mixes or HMA (Hot Max Asphaft).
Las mezclas en caliente ofrecen, en general, buenos resultados en cuanto a la manejabilidad y funcionamiento del asfalto. Sin embargo, presentan efectos adversos con el medio ambiente, la salud de los trabajadores, el consumo de energía y el envejecimiento prematuro del asfalto, debido a las altas temperaturas. FOT e|empto, calentar el asfalto requiere grandes cantidades de energía, ue se obtiene comúnmente de combustibles fósiles, Sos cuales generan una gran carótidas! ate gases tóxicos y gases invernadero como CO2-Hot mixes offer, in general, good results in terms of the handling and operation of asphalt. However, they have adverse effects on the environment, workers' health, energy consumption and premature asphalt aging, due to high temperatures. FOT e | empto, heating asphalt requires large amounts of energy, which is commonly obtained from fossil fuels, which generate a large carotid! tie toxic gases and greenhouse gases such as CO 2 -
Adidonaimente, existen las mezclas en frío que se basan en emuEsñcwtes asf¾[£ficas que no requieren altas temperaturas, pero presentan otro tipo de problemas, ΟΒΠΙΠΚΟ la poca adhesión entre el agregado pétreo y el asfalto por la presencia de agua, hs sipas diffitnulta la compactacíón. Cuando se pavimenta con mezclas en frío se requiere de artas tiempo para poder abrir los caminos al tránsito vehicular. Este tipo de mezclas se aítíGza peco y prim ainTBetratte raro trifinrasas 9mss. Una alternativa viable a las mezclas en caliente son las mezclas tibias o WEV Warm Mix Asphalt). En las mezclas tibias el asfalto se calienta a menores temperaturas que en las mezclas en caliente. Las temperaturas de mezclado y de tendido de las mezclas tibias es de entre 95°C y 140°C aproximadamente. Adidonamentente, there are cold mixtures that are based on emuEsñcwtes asf f [£ ficas that do not require high temperatures, but present other problems, poca the low adhesion between the stone aggregate and the asphalt due to the presence of water, hs sipas diffitnulta la compaction When paving with cold mixtures, it takes time to open the roads to vehicular traffic. This type of mixtures is aitíGza peco and prim ainTBetratte rare trifinrasas 9mss. A viable alternative to hot mixes is warm mixes or WEV Warm Mix Asphalt). In warm mixtures, asphalt heats at lower temperatures than in hot mixtures. The mixing and laying temperatures of the warm mixtures is between approximately 95 ° C and 140 ° C.
Las mezclas tibias ofrecen diversas ventajas sobre las mezclas en caliente, como son; el considerable ahorro de energía durante el calentamiento, la disminución de emisiones gaseosas a la atmósfera provenientes de la quema de combustible, tales como gases invernadero, compuestos orgánicos volátiles (VOC) y olores desagradables. Warm mixes offer several advantages over hot mixes, such as; considerable energy savings during heating, the decrease of gaseous emissions into the atmosphere from the burning of fuel, such as greenhouse gases, volatile organic compounds (VOCs) and unpleasant odors.
Además, se ha demostrado que utilizar mezclas tibias disminuye el envejecimiento del asfalto en el proceso de producción de la mezcla asfáltica, lo que repercute positivamente en la vida útil y en las propiedades mecánicas del pavimento. Como la temperatura de manejo del asfalto es menor, se disminuye el tiempo de espera para abrir caminos recién pavimentados al tránsito vehicular, se incrementa la temporada estacional de aplicación del pavimento y permite que las distancias dell lugar de producción al lugar de aplicación del pavimento sean más largas. In addition, it has been shown that using warm mixtures decreases asphalt aging in the asphalt mix production process, which has a positive effect on the life and mechanical properties of the pavement. As the asphalt handling temperature is lower, the waiting time to open freshly paved roads to vehicular traffic is reduced, the seasonal season of pavement application is increased and allows distances from the place of production to the place of application of the pavement to be Longer
Las mezclas tibias permiten ahorrar en costos por aislamiento en las plantas de asfalto y ampliar el rango de temperatura ambiente de aplicación y compactadón de la mezcla asfáltica. Las mezclas tibias son compatibles con los diseños de carpetas más comunes en el mercado tales como SUPE PAVE y Marshall.  Warm mixtures allow cost savings for insulation in asphalt plants and extend the range of application and compaction ambient temperature of the asphalt mixture. Warm mixes are compatible with the most common folder designs on the market such as SUPE PAVE and Marshall.
Las mezclas tibias ofrecen muchas ventajas sobre las mezclas en caliente o las mezclas frías, la única dificultad que presentan se relaciona con la viscosidad deD asfalto. La viscosidad del asfalto es mayor a temperaturas de mezclas tibias,, por Do que en ocasiones, se impide el recubrimiento total del agregado pétreo y se dificulta su aplicación durante el mezclado, tendido y compactación. Warm mixes offer many advantages over hot mixes or cold mixes, the only difficulty they present is related to the viscosity of asphalt. The viscosity of the asphalt is higher at temperatures of warm mixtures, so that sometimes, the total coating of the stone aggregate is prevented and its application is difficult during mixing, laying and compaction.
Para tratar de solucionar el problema de viscosidad del asfalto y la difícil manejabilidad del asfalto en mezclas tibias han surgido diferentes tecnologías- Actualmente las tecnologías para producir mezclas tibias pueden clasificarse en tres categorías: las ceras que se producen con el método de Fisher-Tropsch, las tecnologías que introducen agua mediante algún mecanismo a la mezcla asfáltica y las tectrcoEogías que requieren hacer cambios en el diseño mecánico de la planta de asfalto em caliente para adaptarlas a producir las mezclas asfálticas a menores temperaturas. Estas tecnologías no son eficientes y a veces tienen efectos contraproducentes, por ejemplo, está reportado en el documento U.S. Pat. No. 2010/0319577 Al que la adición de ceras puede cambiar el tipo de asfalto y provocar tendencia a la fractura en los pavimentos. También se sabe que la aplicación deliberada de agua en la mezcla asfáltica resulta dañina en el desempeño del pavimento. Otras veces resulta costoso e incómodo hacer modificaciones en el proceso de producción y en el diseño de las plantas de asfalto. To try to solve the problem of asphalt viscosity and the difficult handling of asphalt in warm mixtures, different technologies have emerged- Currently, technologies to produce warm mixtures can be classified into three categories: the waxes that are produced with the Fisher-Tropsch method, the technologies that introduce water through some mechanism to the asphalt mixture and the technologies that require changes in the mechanical design of the hot asphalt plant to adapt them to produce asphalt mixtures at lower temperatures. These technologies are not efficient and sometimes have counterproductive effects, for example, it is reported in the US Pat document. No. 2010/0319577 To which the addition of waxes can change the type of asphalt and cause a tendency to break the pavement. It is also known that the deliberate application of water in the asphalt mixture is harmful in the performance of the pavement. Other times it is expensive and inconvenient to make changes in the production process and in the design of asphalt plants.
El documento U.S. Pat. No. 7, 935,749 menciona que estas tecnologías no reducen la viscosidad del asfalto, sino que forman planos de deslizamiento en el asfalto en forma de glóbulos microscópicos de sustancias que no son solventes líquidos a las temperaturas de mezcla del asfalto. Estos glóbulos aplican cierta fuerza sobre el asfalto y en respuesta éste se deforma y se vuelve más fluido y fácil de mezclar con el agregado a temperaturas más bajas que las temperaturas de mezclas en caliente.  The U.S. document Pat. No. 7, 935,749 mentions that these technologies do not reduce the viscosity of the asphalt, but instead form gliding planes on the asphalt in the form of microscopic globules of substances that are not liquid solvents at the asphalt mixing temperatures. These globules apply a certain force on the asphalt and in response it deforms and becomes more fluid and easy to mix with the aggregate at lower temperatures than hot mix temperatures.
Algunos aditivos conocidos para mezclas tibias de origen orgánico y producidos medíante Fischer-Tropsch (FT) son Sasobit® (Estados Unidos) y Asphattan® (Romonta GmbH, Alemania). Sasobit® es una resina hidrocarbonada formada por largas cadenas alifáticas y soluble en el ligante asfáltico y Asphaftan18 es una resina estérica de bajo peso molecular que se presenta en forma granular. Ambos se utilizan en un porcentaje entre 2 y 4% sobre el peso de la mezcla. Some known additives for warm mixtures of organic origin and produced through Fischer-Tropsch (FT) are Sasobit ® (United States) and Asphattan ® (Romonta GmbH, Germany). Sasobit ® is a hydrocarbon resin formed by long aliphatic chains and soluble in the asphalt binder and Asphaftan 18 is a low molecular weight steric resin that is presented in granular form. Both are used in a percentage between 2 and 4% on the weight of the mixture.
Entre las tecnologías que adicionan agua a la mezcla asfáltica se encuentran las de espumado como Aspha-min (Eurovia Services of Bottrop, Germany), que es orna zeolita sintética con aiuminosilicato de sodio y que es cristalizada hidrotérmicameote, tiene un contenido de agua de aproximadamente 20%. Con el calor el agua escapa de la estructura de la zeolita y ocasiona una expansión en volumen del asfalto mediante espumado.  Among the technologies that add water to the asphalt mixture are foaming such as Aspha-min (Eurovia Services of Bottrop, Germany), which is synthetic zeolite orna with sodium aiuminosilicate and that is hydrothermally crystallized, has a water content of approximately twenty%. With heat, water escapes from the structure of the zeolite and causes an expansion in volume of the asphalt by foaming.
Otra tecnología de espumado está descrita en el documento U.S. Pat. No. 7S 713,345 como un aditivo de polifosfatos modificados y zeolitas sintéticas las cuales se añaden como polvo fino al asfalto para crear un efecto espumante. El documento U.S. Pat. No.6, 414,071 describe un aditivo de aluminosilicatos de sodio para mejorar la manejabilidad del asfalto en mezdas tibias. Una tecnología más con adición de agua y espumado está descrita en el documento U.S. Pat. No. 6, 846,354. En donde el agregado se impregna con un ligante suave de asfalto y una vez pre-cubierto se mezcla con un ligante fuerte de asfalto mediante una inyección de agua. Other foaming technology is described in US Pat. No. 7 S 713,345 as an additive of modified polyphosphates and synthetic zeolites which are added as fine powder to the asphalt to create a foaming effect. The US Pat. No.6, 414,071 describes a sodium aluminosilicate additive to improve the handling of asphalt in warm mixtures. One more technology with addition of water and foaming is described in US Pat. No. 6, 846,354. Where the aggregate is impregnated with a soft asphalt binder and once precoated it is mixed with a strong asphalt binder by water injection.
Otras tecnologías como la descrita en el documento U.S. Pat. No. 7, 713, 345 propone el uso de un fosfato hidratado y el documento U.S. Pat. No. 7, 935,749 B2 describe la utilización de una dispersión de látex con polialcoholes para disminuir la temperatura de mezcla y compactación del pavimento. El documento US2010/0319577 propone una combinación de surfactantes y modificadores Teológicos. Other technologies such as that described in U.S. Pat. No. 7, 713, 345 proposes the use of a hydrated phosphate and U.S. Pat. No. 7, 935,749 B2 describes the use of a latex dispersion with polyalcohols to decrease the mixing and compaction temperature of the pavement. US2010 / 0319577 proposes a combination of surfactants and theological modifiers.
Sin embargo, la necesidad real es disminuir la viscosidad del asfalto a temperaturas de mezclas tibias y se requiere de un producto más accesible en todos los sentidos, que no implique modificaciones incómodas en las plantas de asfalto, que no introduzca deliberadamente agua en la mezcla asfáltica y que no modifique negativamente las características del asfalto o de la mezcla asfáltica y por lo tanto del pavimento. However, the real need is to reduce the viscosity of the asphalt at temperatures of warm mixtures and a more accessible product is required in all directions, which does not involve uncomfortable modifications in the asphalt plants, which does not deliberately introduce water into the asphalt mixture and that it does not negatively modify the characteristics of asphalt or asphalt mixture and therefore of the pavement.
La producción de mezclas tibias requiere de un producto que disminuya la viscosidad del asfalto en un rango específico de temperaturas, entre 97°C y 140°C„ que son las temperaturas de mezclado y compactación para mezclas tibias. Este producto debe conservar las propiedades mecánicas del asfalto, la mezcla asfáltica y por lo tanto conferir resistencia al pavimento. Además de proporcionar beneficios adicionales como incrementar la adherencia del asfalto con el agregado pétreo, prevenir el envejecimiento del asfalto y ser de fácil aplicación. The production of warm mixtures requires a product that decreases the viscosity of the asphalt in a specific temperature range, between 97 ° C and 140 ° C „which are the mixing and compaction temperatures for warm mixtures. This product must preserve the mechanical properties of asphalt, asphalt mixture and therefore confer resistance to the pavement. In addition to providing additional benefits such as increasing the adhesion of the asphalt with the stone aggregate, preventing the aging of the asphalt and being easy to apply.
La presente invención resuelve la problemática aquí descrita porque sus principales funciones son:  The present invention solves the problem described here because its main functions are:
1. Modificar la viscosidad del asfalto en un rango específico de temperaturas. 2. Prevenir el envejecimiento del asfalto.  1. Modify the viscosity of asphalt in a specific range of temperatures. 2. Prevent asphalt aging.
3. Mantener las propiedades mecánicas de la mezcla asfáltica.  3. Maintain the mechanical properties of the asphalt mixture.
4. Promover la adherencia entre el agregado pétreo y el asfalto.  4. Promote the adhesion between the stone aggregate and the asphalt.
Cabe mencionar que las reacciones entre ácidos carboxílicos y aminas, para obtener amidas son bien conocidas, el documento U.S. Pat. No. 6, 786,963 señada Da reacción entre poliácidos y poliaminas para obtener un compuesto multiamida a partir de los grupos ácidos de los poliácidos. En la presente invención se obtiene un producto de amidoamina a partir de los grupos amino de las poliaminas y un monoáctdo contenido en un triglicérido. En este tipo de reacciones no se requiere el uso de poliácidos, porque se pide tener una amina libre en el compuesto resultante de la reacción. Una ventaja adicional en este proceso es que ¡ndustrialmente, es más fácil conseguir monoácidos que poliácidos. It should be mentioned that the reactions between carboxylic acids and amines, to obtain amides are well known, US Pat. No. 6, 786,963 indicated Reacts between polyacids and polyamines to obtain a multiamide compound from the acidic groups of the polyacids. In the present invention a product of amidoamine from the amino groups of the polyamines and a monoctate contained in a triglyceride. In this type of reactions the use of polyacids is not required, because it is requested to have a free amine in the compound resulting from the reaction. An additional advantage in this process is that industrially, it is easier to obtain monoacids than polyacids.
OBJETO DE LA INVENCIÓN  OBJECT OF THE INVENTION
La presente invención se refiere a compuestos de amidoamina, que tienen propiedades tales como modificar la viscosidad del asfalto, promover la adherencia del asfalto con el agregado pétreo, mantener las propiedades mecánicas de la mezcla asfáltica y prevenir el envejecimiento del asfalto en mezclas tibias utilizadas para pavimentación. La presente invención también provee asfaltos modificados, mezclas asfálticas y su uso. The present invention relates to amidoamine compounds, which have properties such as modifying the viscosity of the asphalt, promoting the adhesion of the asphalt with the stone aggregate, maintaining the mechanical properties of the asphalt mixture and preventing the aging of the asphalt in warm mixtures used for paving. The present invention also provides modified asphalts, asphalt mixtures and their use.
DESCRIPCIÓN DETALLADA DE LA INVENCIÓN DETAILED DESCRIPTION OF THE INVENTION
El compuesto de amidoamina de la presente invención se obtiene de la reacción entre bis-hexametilentriamina y triestearato de glicerilo, obteniéndose la amidoamina correspondiente y que comprende en su estructura un grupo amino secundario libre. Este compuesto de amidoamina, puede ser o no ser purificado para uso en asfalto y mezclas asfálticas para pavimentación. The amidoamine compound of the present invention is obtained from the reaction between bis-hexamethylenetriamine and glyceryl triestearate, obtaining the corresponding amidoamine and comprising in its structure a free secondary amino group. This amidoamine compound may or may not be purified for use in asphalt and asphalt paving mixtures.
En el campo técnico de la invención se conoce como asfaltos modificados, aquellos asfaltos que son mezclados con polímeros para cambiar sus propiedades teológicas y mecánicas, en este caso, debe entenderse como Asfalto Modificado, el asfalto que ha sido adicionado con el compuesto de amidoamina de la presenta invención, ya sea purificado o sin purificar. In the technical field of the invention it is known as modified asphalts, those asphalts that are mixed with polymers to change their theological and mechanical properties, in this case, it should be understood as Modified Asphalt, the asphalt that has been added with the amidoamine compound of The present invention, whether purified or unpurified.
La reacción entre bis-hexametilentriamina y estearato de glicerilo es urna reacción estéricamente impedida. Las aminas primarias de los extremos de la poliamina reaccionan, en primer lugar con el grupo carboxilo del triglicérido, y se forma un producto amidoamina con una amina secundaria libre en el interior de la molécula. Si la reacción se prolonga, las aminas secundarias libres continuarán reaccionando. The reaction between bis-hexamethylenetriamine and glyceryl stearate is a sterically hindered reaction. The primary amines of the polyamine ends react, first of all with the carboxyl group of the triglyceride, and an amidoamine product is formed with a free secondary amine inside the molecule. If the reaction is prolonged, the free secondary amines will continue to react.
El orden de reacción que se menciona en la presente invención es contrario al reportado normalmente, porque las aminas secundarias son más reactivas que las aminas primarias y por tanto reaccionan primero. Sin embargo, gracias a Da reacción e transesterificación que se da entre el triglicérido y la amina, el impedimento esférico provoca que reaccionen, en primer lugar, las aminas primarias y posteriormente las aminas secundarias. Este orden de reacción se conserva cuando se propician las condiciones de reacción adecuadas en tiempo y temperatura. The reaction order mentioned in the present invention is contrary to that normally reported, because secondary amines are more reactive than primary amines and therefore react first. However, thanks to the reaction and transesterification that occurs between triglyceride and the amine, the spherical impediment causes the primary amines and then the secondary amines to react first. This reaction order is preserved when the appropriate reaction conditions in time and temperature are propitiated.
El compuesto de amidoamina se fabrica de la siguiente manera: The amidoamine compound is manufactured as follows:
i. Se mezcla BHMT (bis-hexametilentriamina) y triestearato de glicerilo en una relación estequiométrica, sub-estequiométrica y sobre-estequiométrica. ii. Se calienta la mezcla de 2 a 6 horas a una temperatura desde 150°C y hasta 220°C, para llevar a cabo la reacción entre los reactivos.  i. BHMT (bis-hexamethylenetriamine) and glyceryl triestearate are mixed in a stoichiometric, sub-stoichiometric and over-stoichiometric ratio. ii. The mixture is heated for 2 to 6 hours at a temperature from 150 ° C to 220 ° C, to carry out the reaction between the reagents.
iii. Se detiene el calentamiento hasta lograr una temperatura ambiente, para detener la reacción.  iii. Heating is stopped until an ambient temperature is achieved, to stop the reaction.
La relación estequiométrica que se prefiere es 3 bis-hexametilentriamina :2 triestearato de glicerilo.  The preferred stoichiometric ratio is 3 bis-hexamethylenetriamine: 2 glyceryl triestearate.
A manera de ejemplo enunciativo, pero no limitativo, el rendimiento de reacción puede calcularse mediante la determinación del índice de amina total, índice de amina secundaria e índice de amina primaria, al inicio y al final de la reacción. De Da amina total, el 66.6% corresponde a amina primaria y el 33.3% corresponde a amina secundaria. De tal manera, que de acuerdo al consumo de la amina primaria, puede calcularse el rendimiento de la reacción. Puede darse el caso en el que la amina secundaria se consuma y si es así, también se toma en cuenta para calcular el rendimiento de reacción. El índice de amina se mide en miligramos (mg) de hidróxido de potasio (KOH) por gramo (g) de muestra. By way of example, but not limitation, the reaction yield can be calculated by determining the total amine index, secondary amine index and primary amine index, at the beginning and at the end of the reaction. Of total Da amina, 66.6% corresponds to primary amine and 33.3% corresponds to secondary amine. Thus, according to the consumption of the primary amine, the reaction yield can be calculated. It may be the case where the secondary amine is consumed and if so, it is also taken into account to calculate the reaction yield. The amine index is measured in milligrams (mg) of potassium hydroxide (KOH) per gram (g) of sample.
A manera de ejemplo, enunciativo, pero no limitativo, la reacción puede ser seguida mediante FT-IR (Espectrometría infraroja por transformadas de Fourier) a diferentes tiempos de reacción y observar la desaparición de las bandas correspondientes a los grupos carbonilo del triestearato de glicerilo y observar la aparición de las bandas correspondientes a los grupos amida del producto de reacción.  By way of example, but not limited to, the reaction can be followed by FT-IR (Fourier transform infrared spectrometry) at different reaction times and observe the disappearance of the bands corresponding to the carbonyl groups of glyceryl triestearate and observe the appearance of the bands corresponding to the amide groups of the reaction product.
A manera de ejemplo, enunciativo pero no limitativo, la presente invención puede ser purificada por métodos conocidos como a) Formación de sal de amina, b) Cromatografía, c) Cromatografía en columna, etc. By way of example, but not limited to, the present invention can be purified by methods known as a) Formation of amine salt, b) Chromatography, c) Column chromatography, etc.
Figure imgf000008_0001
Figure imgf000008_0001
El producto resultado de la reacción anterior, puede ser o no ser purificado y en ambas formas el compuesto de amidoamina conserva sus propiedades y se utiliza para modificar asfaltos y en mezclas tibias para pavimentación. The product resulting from the previous reaction may or may not be purified and in both forms the amidoamine compound retains its properties and is used to modify asphalts and in warm paving mixtures.
A manera de ejemplo, enunciativo pero no limitativo, la presentación del compuesto de amidoamina de la presente invención, ya sea purificado o sin purificar, puede ser en formas conocidas como: a) Pellets, b) Hojuelas, c) Emulsiones, d) Disoluciones, etc. El compuesto de amidoamina de la presente invención, soluciona el problema de difícil manejo del asfalto a temperaturas de mezclas tibias. Dicho producto presenta un comportamiento único, ya que reduce la viscosidad del asfalto entre 97°C y 140°C y aumentan la viscosidad del asfalto por debajo de 97°C, como se observa en Sa Figura 3. Tal comportamiento favorece el proceso de pavimentación, ya que por un lado permite que el asfalto sea poco viscoso y fácil de trabajar a menores temperaturas y por otro lado contribuye a una mejor compactación y al mismo tiempo ayuda a que el asfalto solidifique más rápido y los caminos puedan abrirse en menor tiempo al tránsito vehicular. Adicionalmente, el compuesto de amidoamina, de la presente invención promueve la adherencia entre el agregado pétreo y el asfalto, mantienen las propiedades mecánicas de la mezcla asfáltica y previene el envejecimiento del asfalto. La presente invención proporciona compuestos de amidoamina, el proceso de su fabricación y su uso, asfaltos modificados y mezclas asfálticas para pavimentar. El asfalto modificado comprende a) Asfalto y b) El compuesto de amidoamina de la presente invención de la fórmula (I) desde 1% y hasta 6% con respecto aD peso del asfalto. La mezcla asfáltica comprende a) Asfalto Modificado con el compuesto de amidoamina de la presente invención de la fórmula química (I) desde 3.5% y hasta 8%, b) Agregado pétreo desde 92% y hasta 96.5%. By way of example, but not limited to, the presentation of the amidoamine compound of the present invention, whether purified or unpurified, may be in known forms such as: a) Pellets, b) Flakes, c) Emulsions, d) Solutions , etc. The amidoamine compound of the present invention solves the problem of difficult handling of asphalt at warm mixing temperatures. This product has a unique behavior, since it reduces the viscosity of the asphalt between 97 ° C and 140 ° C and increases the viscosity of the asphalt below 97 ° C, as observed in Sa Figure 3. Such behavior favors the paving process , since on the one hand it allows the asphalt to be less viscous and easy to work at lower temperatures and on the other hand it contributes to better compaction and at the same time it helps the asphalt to solidify faster and the roads can be opened in less time at vehicular traffic. Additionally, the amidoamine compound of the present invention promotes adhesion between stone aggregate and asphalt, maintains the mechanical properties of the asphalt mixture and prevents asphalt aging. The present invention provides amidoamine compounds, the manufacturing process and its use, modified asphalts and asphalt paving mixtures. The modified asphalt comprises a) Asphalt and b) The amidoamine compound of the present invention of the formula (I) from 1% and up to 6% with respect to asphalt weight. The asphalt mixture comprises a) Modified asphalt with the amidoamine compound of the present invention of the chemical formula (I) from 3.5% to 8%, b) Stone aggregate from 92% and up to 96.5%.
Los porcentajes de agregado pétreo y asfalto modificado en las mezclas asfálticas son porcentajes estándar y pueden variar de acuerdo a las necesidades del diseño de la mezcla.  The percentages of stone aggregate and modified asphalt in asphalt mixtures are standard percentages and may vary according to the needs of the mixture design.
Los asfaltos modificados con el compuesto de amidoamina de la presente invención, se fabrican de la siguiente manera:  The asphalts modified with the amidoamine compound of the present invention are manufactured as follows:
a) Se calienta el asfalto a una temperatura de entre 90°C y 140°C.  a) The asphalt is heated to a temperature between 90 ° C and 140 ° C.
b) Se adiciona el compuesto de amidoamina de la presente invención de la fórmula (I) desde 1% y hasta 6% con respecto al peso del asfalto.  b) The amidoamine compound of the present invention of the formula (I) from 1% and up to 6% with respect to the weight of the asphalt is added.
c) Se agita el asfalto hasta lograr una mezcla homogénea.  c) The asphalt is stirred until a homogeneous mixture is achieved.
Las características que presentan los asfaltos modificados con el compuesto de amidoamina de la presente invención son:  The characteristics of modified asphalts with the amidoamine compound of the present invention are:
i. Modificación en la viscosidad (Figura 3).  i. Modification in viscosity (Figure 3).
ii. Menor tendencia al envejecimiento (Tabla 7).  ii. Less aging tendency (Table 7).
iii. Incremento en la resistencia a la deformación del asfalto (Figura 5).  iii. Increase in resistance to asphalt deformation (Figure 5).
iv. Menor penetración (Figura 4).  iv. Less penetration (Figure 4).
Las mezclas asfálticas con asfalto modificado con el compuesto de amidoamina de la presente invención, se fabrican de la siguiente manera:  Asphalt mixtures with modified asphalt with the amidoamine compound of the present invention are manufactured as follows:
a) Se calienta el asfalto modificado a una temperatura de entre 90°C y 140°C. b) Se realiza una mezcla con agregado pétreo en donde el porcentaje final de los componentes a) Asfalto modificado es desde 3.5% y hasta 8% y b) Agregado pétreo es desde 92% y hasta 96.5%.  a) The modified asphalt is heated to a temperature between 90 ° C and 140 ° C. b) A mixture is made with stone aggregate where the final percentage of the components a) Modified asphalt is from 3.5% and up to 8% and b) Stone aggregate is from 92% and up to 96.5%.
c) Se agita la mezcla hasta recubrir completamente el agregado pétreo.  c) The mixture is stirred until the stone aggregate is completely covered.
El desempeño del compuesto de amidoamina de la presente invención tiene las siguientes características cuando se utiliza para modificar asfalto y en mezclas tibias para pavimentación:  The performance of the amidoamine compound of the present invention has the following characteristics when used to modify asphalt and in warm paving mixtures:
1. Modificar la viscosidad del asfalto. Disminuyen la viscosidad del asfalto desde un 5% y hasta un 40% con respecto a la viscosidad del asfalto virgen o blanco, en un rango de temperaturas desde 97°C y hasta 140°C (Figura 3). Por lo que confiere manejabilidad al asfalto en las temperaturas de trabajo de mezclas tibias para pavimentación y se consigue una mejor compactacion del asfalto durante la pavimentación. 1. Modify the viscosity of the asphalt. They reduce the viscosity of asphalt from 5% and up to 40% with respect to the viscosity of virgin or white asphalt, in a temperature range from 97 ° C to 140 ° C (Figure 3). As a result, it gives the asphalt workability in the working temperatures of warm paving mixtures and a better compaction of the asphalt during paving is achieved.
Por otra parte, el compuesto de amidoamina de la presente invención, incrementa la viscosidad del asfalto a temperatura ambiente del pavimento. Por lo que el asfalto se mantiene sólido y la mezcla asfáltica para pavimentación conserva sus propiedades mecánicas (Figura 3).  On the other hand, the amidoamine compound of the present invention increases the viscosity of the asphalt at room temperature of the pavement. Asphalt remains solid and asphalt paving mix retains its mechanical properties (Figure 3).
2. Promover la adherencia entre el agregado pétreo y el asfalto.  2. Promote the adhesion between the stone aggregate and the asphalt.
El compuesto de amidoamina de la presente invención, incrementa notablemente la adherencia entre el agregado pétreo y el asfalto, debido a su estructura química, que como es sabido, las amidas incrementan la adherencia entre el asfalto y Dos minerales (Tabla 2).  The amidoamine compound of the present invention significantly increases the adhesion between the stone aggregate and the asphalt, due to its chemical structure, which, as is known, the amides increase the adhesion between the asphalt and two minerals (Table 2).
3. Mantener las propiedades mecánicas de la mezcla asfáltica.  3. Maintain the mechanical properties of the asphalt mixture.
El compuesto de amidoamina de la presente invención mantiene el módulo de resiliencia de la mezcla asfáltica (Figura 5).  The amidoamine compound of the present invention maintains the resilience modulus of the asphalt mixture (Figure 5).
4. Prevenir el envejecimiento del asfalto  4. Prevent asphalt aging
El compuesto de amidoamina de la presente invención conserva el grado PG (grado de desempeño o performance grade) del asfalto después de un periodo de envejecimiento (Tabla 7).  The amidoamine compound of the present invention retains the PG grade (performance grade) of the asphalt after an aging period (Table 7).
Breve descripción de las figuras:  Brief description of the figures:
La Figura 1 es el espectro de masas de ionización por electrospray (ESI-MS) del compuesto de amidoamina purificado obtenido a partir de la reacción de triestearato de glicerilo y bis-hexametilentriamina.  Figure 1 is the electrospray ionization (ESI-MS) mass spectrum of the purified amidoamine compound obtained from the reaction of glyceryl triestearate and bis-hexamethylenetriamine.
La Figura 2 es el espectro de FT-IR que muestra el avance de la reacción de para obtener el compuesto de amidoamina de la presente invención. Se observa la formación del compuesto de amidoamina.  Figure 2 is the FT-IR spectrum showing the progress of the reaction to obtain the amidoamine compound of the present invention. The formation of the amidoamine compound is observed.
La Figura 3 es la gráfica que muestra cómo se modifica la viscosidad del asfalto cuando éste se adiciona con el compuesto de amidoamina sin purificar de Oa presente invención. La viscosidad disminuye hasta en un 30%, en un rango de entre 97°C y 140°C, y aumente hasta en un 36% por debajo de 97°C con respecto al blanco. Figure 3 is the graph showing how the viscosity of asphalt is modified when it is added with the unpurified amidoamine compound of Oa present invention. The viscosity decreases by up to 30%, in a range between 97 ° C and 140 ° C, and increases up to 36% below 97 ° C with respect to the target.
La Figura 4 es la gráfica que muestra la penetración del asfalto a 25°C, que disminuye cuando el asfalto es modificado con el compuesto de amidoamina sin purificar de la presente invención. Figure 4 is the graph showing the penetration of asphalt at 25 ° C, which decreases when the asphalt is modified with the unpurified amidoamine compound of the present invention.
La Figura 5 es la gráfica que muestra que el módulo de resiliencia se conserva a diferentes temperaturas de compactación, cuando la carpeta asfáltica se prepara con asfalto para mezclas tibias modificado con el compuesto de amidoamina de la presente invención.  Figure 5 is the graph showing that the resilience module is preserved at different compaction temperatures, when the asphalt binder is prepared with asphalt for warm mixtures modified with the amidoamine compound of the present invention.
EJEMPLOS  EXAMPLES
Los siguientes ejemplo tienen la finalidad de ilustrar la invención, no de limitarla, cualquier variación cae dentro del ámbito de la presente invención.  The following examples are intended to illustrate the invention, not to limit it, any variation falls within the scope of the present invention.
Debe entenderse que los datos presentados en los ejemplos, corresponden al compuesto de amidoamina sin purificar, a menos que se indique lo contarlo. It should be understood that the data presented in the examples correspond to the unpurified amidoamine compound, unless indicated.
Debe entenderse como Asfalto Modificado, el asfalto que ha sido adicionado con el compuesto amidoamina de la presente invención, ya sea que el compuesto de amidoamina sea purificado o sin purificar. It should be understood as Modified Asphalt, the asphalt that has been added with the amidoamine compound of the present invention, whether the amidoamine compound is purified or unpurified.
Ejemplo 1. Elaboración y evaluación de un Blanco, para hacer notar las propiedades del compuesto de amidoamina de la presente invención y las características del asfalto modificado y de la mezcla asfáltica preparada con asfalto modificado. Example 1. Preparation and evaluation of a Target, to note the properties of the amidoamine compound of the present invention and the characteristics of the modified asphalt and the asphalt mixture prepared with modified asphalt.
Se utilizó Asfalto virgen AC-20 Salamanca como blanco, para evaluar sus características. Se evaluaron la viscosidad, el porcentaje de penetración, sus propiedades Teológicas; PG, Temperatura de Falla, Módulo Reológico y Ángulo de Fase, el porcentaje de desprendimiento por fricción y la conservación del módulo de resiliencia. Como se indica a continuación: Virgin AC-20 Salamanca asphalt was used as a blank, to evaluate its characteristics. The viscosity, the penetration percentage, its Theological properties were evaluated; PG, Failure Temperature, Rheological Module and Phase Angle, the percentage of friction detachment and the conservation of the resilience module. As follows:
i. Evaluación de la viscosidad del asfalto  i. Asphalt viscosity assessment
a) Se calentó el asfalto hasta alcanzar una temperatura homogénea de 140°C. a) The asphalt was heated to a homogeneous temperature of 140 ° C.
b) Se agitó durante 15 minutos. Se evaluó la viscosidad del asfalto en un rango de temperaturas de ertttre 90°C y 140°C, con un viscosímetro Brookfield modelo LVDV-I+, con una aguja del número 27. b) It was stirred for 15 minutes. Asphalt viscosity was evaluated in a temperature range of ertttre 90 ° C and 140 ° C, with a Brookfield viscometer model LVDV-I +, with a number 27 needle.
Tabla 1. Viscosidad del Blanco a diferentes temperaturas.  Table 1. White viscosity at different temperatures.
Figure imgf000012_0001
Figure imgf000012_0001
Se observa un comportamiento normal en el asfalto; la viscosidad del asfalto disminuye conforme la temperatura aumenta, sin embargo se sabe que a estas temperaturas de mezclas tibias, el asfalto no es lo suficientemente fluido para proporcionar una adecuada manejabilidad. Este comportamiento se observa gráficamente en la Figura 3.  Normal behavior is observed on the asphalt; the viscosity of the asphalt decreases as the temperature increases, however it is known that at these temperatures of warm mixtures, the asphalt is not fluid enough to provide adequate handling. This behavior is seen graphically in Figure 3.
ii. Evaluación de la penetración del asfalto  ii. Asphalt Penetration Evaluation
a) Se evaluó la penetración del asfalto con un Penetrómetro Controls, de acuerdo al manual M-MMP-4-05-006/00 de la Secretaria de Comunicaciones y Transportes de México. a) Asphalt penetration was evaluated with a Controls Penetrometer, according to the M-MMP-4-05-006 / 00 manual of the Ministry of Communications and Transportation of Mexico.
Tabla 2. Penetración del Blanco
Figure imgf000012_0002
Table 2. Target Penetration
Figure imgf000012_0002
La penetración que presenta el blanco se considera normal, para un asfalto virgen AC- 20 Salamanca y se puede observar gráficamente en la Figura 4.  The penetration presented by the target is considered normal, for a virgin AC-20 Salamanca asphalt and can be seen graphically in Figure 4.
iii. Evaluación de las propiedades reológicas del asfalto; PG, Temperatura de Falla, Módulo Reológico y Ángulo de Fase,  iii. Evaluation of the rheological properties of asphalt; PG, Failure Temperature, Rheological Module and Phase Angle,
a) Las propiedades reológicas del asfalto se evaluaron de manera estándar bajo la metodología sugerida por SUPERPAVE, en un Reómetro de corte dinámico TA Instruments, modelo AR2000. a) The rheological properties of the asphalt were evaluated in a standard way under the methodology suggested by SUPERPAVE, in a TA Instruments dynamic cutting rheometer, model AR2000.
Los parámetros Teológicos del asfalto describen su comportamiento bajo condiciones determinadas de prueba. Se miden parámetros como G*/sen6 que ofrece una aproximación de la resistencia que presenta el asfalto a ser deformado permanentemente y δ que describe la visco-elasticidad del asfalto. El grado PG muestra el comportamiento del asfalto al ser sometido a un proceso de envejecimiento, un aumento significativo en este parámetro indica que el asfalto se endureció demasiado. The Theological parameters of asphalt describe its behavior under certain test conditions. Parameters such as G * / sen6 that offer a approximation of the resistance presented by the asphalt to be permanently deformed and δ that describes the visco-elasticity of the asphalt. The PG grade shows the behavior of the asphalt when subjected to an aging process, a significant increase in this parameter indicates that the asphalt hardened too much.
Tabla 3. Propiedades Reológicas del Blanco
Figure imgf000013_0001
Table 3. White Rheological Properties
Figure imgf000013_0001
Original; Asfalto que no ha pasado por ningún proceso de envejecimiemt ©. Original; Asphalt that has not gone through any aging process ©.
*RTFO; Proceso de envejecimiento en horno de película delgada rotatorio, a 163 durante 85 minutos.  * RTFO; Aging process in a thin film rotary kiln, at 163 for 85 minutes.
Módulo reológico, G*/sen5; parámetro mediante el cual se mide la resistencia ante la deformación permanente del asfalto.  Rheological module, G * / sen5; parameter by which the resistance to permanent asphalt deformation is measured.
Ángulo de Fase; expresa la visco-elasticidad del asfalto. Phase Angle; expresses the visco-elasticity of asphalt.
PG: Grado de Desempeño o Performance Grade, en este caso solo se presenta la parte de resistencia ante la deformación permanente.  PG: Performance Grade or Performance Grade, in this case only the part of resistance to permanent deformation is presented.
Temperatura de Falla, Temperatura a la cual G*/sen5 es igual a 2.2KPa. Los resultados muestran un comportamiento característico del asfalto virgen, en dónde el proceso de envejecimiento modifica las características reológicas del asfalto. El PG aumenta, lo que indica que el asfalto se endurece y cambia debido al proceso de envejecimiento. El endurecimiento del asfalto después de un proceso de envejecimiento también se observa en los resultados de Módulo Reológico, Temperatura de Falla y Ángulo de fase.  Failure Temperature, Temperature at which G * / sen5 is equal to 2.2KPa. The results show a characteristic behavior of the virgin asphalt, where the aging process modifies the rheological characteristics of the asphalt. The PG increases, indicating that the asphalt hardens and changes due to the aging process. Asphalt hardening after an aging process is also observed in the results of Rheological Module, Failure Temperature and Phase Angle.
iv. Preparación de mezcla asfáltica  iv. Preparation of asphalt mixture
a) Se calentó el asfalto a una temperatura de 140°C.  a) The asphalt was heated to a temperature of 140 ° C.
b) Se realizó una mezcla con agregado pétreo en donde el porcentaje fina! de los componentes fue a) Asfalto virgen 6% y b) Agregado pétreo de 94%.  b) A mixture was made with stone aggregate where the fine percentage! of the components was a) 6% virgin asphalt and b) 94% stone aggregate.
<c} Se agüitó 8a mraezdla ha ta recuabsinr cunsuplletainneirtte el agregad© péttir-KiD. La mezcla asfáltica se elaboró de acuerdo al diseño de mezcla asfáltica de granulometría densa de alto desempeño del protocolo AMAAC PA-MA-001/2008. <c} 8a mraezdla has been added to the cunsuplletainneirtte aggregate © péttir-KiD. The asphalt mix was developed according to the high performance dense granulometry asphalt mix design of the AMAAC PA-MA-001/2008 protocol.
v. Evaluación del porcentaje de desprendimiento por fricción en 8a mezcla asfáltica.  v. Evaluation of the percentage of friction detachment in 8th asphalt mixture.
a) La evaluación del porcentaje de desprendimiento por fricción se realizó de acuerdo a la Recomendación AMAAC 08/2008, con el equipo que allí se señala. a) The evaluation of the percentage of friction detachment was carried out in accordance with Recommendation AMAAC 08/2008, with the equipment indicated therein.
Tabla 4. Porcentaje de desprendimiento por fricción del Blanco.
Figure imgf000014_0001
Table 4. Percentage of friction release of the Target.
Figure imgf000014_0001
1* Agregado pétreo de regular adherencia 1 * Stone aggregate of regular adhesion
2** Agregado pétreo de mala adherencia  2 ** Stony aggregate of poor adhesion
El porcentaje de desprendimiento por fricción es característico de un asfalto virgen, sin aditivos que promuevan la adhesión, ya que el asfalto presenta poca afinidad por el agregado pétreo. The percentage of friction detachment is characteristic of a virgin asphalt, without additives that promote adhesion, since the asphalt has little affinity for the stone aggregate.
vi. Evaluación de la conservación del módulo de resiliencia en la mezcla asfáltica. Para evaluar la conservación del módulo de resiliencia se preparó una mezcla asfáltica de acuerdo al diseño de mezcla asfáltica de granulometría densa de alto desempeño del protocolo AMAAC PA-MA-001/2008 y como se indica en el punto iv.  saw. Evaluation of the conservation of the resilience module in the asphalt mix. To evaluate the conservation of the resilience module, an asphalt mixture was prepared according to the design of high performance dense granulometry asphalt mixture of the AMAAC PA-MA-001/2008 protocol and as indicated in point iv.
Se considera la amplitud como la diferencia entre el valor máximo que toma el módulo de resiliencia y el valor mínimo que éste toma y muestra el tamaño del rango en el que se encuentran los valores. The amplitude is considered as the difference between the maximum value that the resilience module takes and the minimum value that it takes and shows the size of the range in which the values are found.
a) Se determinó el módulo de resiliencia a diferentes temperaturas de compactación, de acuerdo a la metodología descrita por la norma española NTL-360/91.  a) The resilience module at different compaction temperatures was determined, according to the methodology described by the Spanish standard NTL-360/91.
Tabla 5. Módulo de Resiliencia del blanco Table 5. Target Resilience Module
T. compactación [" C) Módulo de Resiliencia  T. compaction ["C) Resilience Module
110 2780  110 2780
120 3162 Amplitud  120 3162 Amplitude
130 3293  130 3293
140 3606 826 La Tabla 5 muestra que el módulo de resiliencia del blanco disminuye conforme la temperatura de compactación disminuye, teniendo una amplitud entre los resultados de 826 y se puede apreciar gráficamente en la Figura 5. Ejemplo 2. Fabricación de compuesto de amidoamina. 140 3606 826 Table 5 shows that the white resilience module decreases as the compaction temperature decreases, having an amplitude between the results of 826 and can be seen graphically in Figure 5. Example 2. Manufacture of amidoamine compound.
El compuesto de amidoamina se preparó de la siguiente manera:  The amidoamine compound was prepared as follows:
i. Se mezcló BHMT (bis-hexametilentriamina) y triestearato de glicerilo en una relación de estequiometria de 3:2, en un matraz bola de dos bocas. ii. Se calentó la mezcla a reflujo, durante 4 horas a una temperatura de 180° C, para llevar a cabo la reacción entre los reactivos.  i. BHMT (bis-hexamethylenetriamine) and glyceryl triestearate were mixed in a stoichiometry ratio of 3: 2, in a two-mouth ball flask. ii. The mixture was heated at reflux, for 4 hours at a temperature of 180 ° C, to carry out the reaction between the reagents.
iii. Se detuvo el calentamiento hasta lograr una temperatura ambiente de 25°C, para detener la reacción.  iii. Heating was stopped until an ambient temperature of 25 ° C was achieved, to stop the reaction.
El índice de amina total, antes de iniciar la reacción fue de 156 mg KOH por gramo de muestra. El índice de amina secundaria del producto de reacción fue de 48 miligramos (mg) de hidróxido de potasio (KOH) y tiene un índice de amina primaria de dos, lo que muestra que la reacción se lleva a cabo mediante las aminas primarias de ios extremos, dejando un grupo amino secundario libre en la molécula. El rendimiento de reacción fue de 90%. El índice de amina se determinó mediante volumetría con titulador automático Metrohm modelo 888 Tritiando. The total amine index, before starting the reaction was 156 mg KOH per gram of sample. The secondary amine index of the reaction product was 48 milligrams (mg) of potassium hydroxide (KOH) and has a primary amine index of two, which shows that the reaction is carried out by the primary amines of ios , leaving a free secondary amino group in the molecule. The reaction yield was 90%. The amine index was determined by volumetry with Metrohm automatic titrator model 888 Tritiando.
El producto de reacción se purificó mediante la formación de su sal de amina para su caracterización. The reaction product was purified by forming its amine salt for characterization.
El compuesto de amidoamina, resultado de esta reacción tiene una temperatura de fusión de 118°C, es soluble en iso-propanol e insoluble en agua y se caracterizó mediante Espectrometría de masas por elecrospray (ESl-MS). El espectro se puede observar en la Figura 1. FÓRMULAS QUÍMI
Figure imgf000016_0001
The amidoamine compound, the result of this reaction has a melting temperature of 118 ° C, is soluble in iso-propanol and insoluble in water and was characterized by elecrospray mass spectrometry (ESl-MS). The spectrum can be seen in Figure 1. QUÍMI FORMULAS
Figure imgf000016_0001
+ 180°C, 4h
Figure imgf000016_0002
+ 180 ° C, 4h
Figure imgf000016_0002
Figure imgf000016_0003
Figure imgf000016_0003
La reacción, se monitoreó mediante FT-IR, al tiempo cero y transcurridas dos y tres horas. Durante el avance de la reacción en FT-IR se observó la desaparición del pico representativo de los grupos carbonilo del triglicérido en 1737 cnrf \ y la aparición del pico representativo de amida en 1634 cm 1 (Figura 2). The reaction was monitored by FT-IR, at zero time and after two and three hours. During the progress of the FT-IR reaction, the disappearance of the representative peak of the triglyceride carbonyl groups was observed in 1737 cnrf and the appearance of the representative amide peak at 1634 cm 1 (Figure 2).
Ejemplo 3. Asfalto modificado con el producto de amidoamina. Example 3. Asphalt modified with the amidoamine product.
a) Se calentó Asfalto AC-20 Salamanca a una temperatura de 140 °C, hasta alcanzar una temperatura homogénea.  a) Asphalt AC-20 Salamanca was heated to a temperature of 140 ° C, until it reached a homogeneous temperature.
b) Se adicionó 3% en peso con respecto al asfalto del compuesto de amidoamina de la presente invención.  b) 3% by weight with respect to the asphalt of the amidoamine compound of the present invention was added.
c) Se agitó la mezcla durante un periodo de 15 minutos, para incorporar completamente el compuesto de amidoamina en el asfalto.  c) The mixture was stirred for a period of 15 minutes, to fully incorporate the amidoamine compound into the asphalt.
Se realizó el mismo procedimiento para modificar asfalto variando los porcentajes con respecto al peso del asfalto del compuesto de amidoamina de la presente invención. En la Figura 3 se puede observar que el compuesto de amidoamina disminuye la viscosidad del asfalto en un rango de concentraciones entre 1% y 6% con respecto al peso del asfalto, en el asfalto modificado, siendo el porcentaje preferido el de 3%, por lo tanto los siguientes ejemplos se refieren a un asfalto modificado con 3% del compuesto de amidoamina de la presente invención, con respecto al peso del asfalto. Se determinó la viscosidad del asfalto modificado, tal como se indica en el ejemplo 1. 0.a Figura 3 ilustra que la viscosidad del asfalto modificado disminuye hasta en un 44%, en un rango de entre 97°C y 140°C, y por debajo de 97°C aumenta hasta 36% con respecto al blanco. Por ejemplo, el blanco presenta viscosidades de 4118cp y 1962cp a 100°C y 110°C respectivamente, y en el asfalto modificado las viscosidades disminuyen a 2976cp y 1357cp respectivamente, lo que equivale a una reducción en la viscosidad de 38% y 44% a ÍOCTC y 110°C respectivamente. The same procedure was performed to modify asphalt by varying the percentages with respect to the asphalt weight of the amidoamine compound of the present invention. In Figure 3 it can be seen that the amidoamine compound decreases the viscosity of the asphalt in a concentration range between 1% and 6% with respect to the weight of the asphalt, in the modified asphalt, the preferred percentage being 3%, by therefore the following examples refer to an asphalt modified with 3% of the amidoamine compound of the present invention, with respect to the weight of the asphalt. The viscosity of the modified asphalt was determined, as indicated in example 1. Figure 3 illustrates that the viscosity of the modified asphalt decreases by up to 44%, in a range between 97 ° C and 140 ° C, and below 97 ° C increases up to 36% with respect to the target. For example, the target has viscosities of 4118cp and 1962cp at 100 ° C and 110 ° C respectively, and in the modified asphalt the viscosities decrease to 2976cp and 1357cp respectively, which is equivalent to a reduction in viscosity of 38% and 44% at IOCTC and 110 ° C respectively.
Ejemplo 4. Evaluación de la penetración del asfalto modificado con el producto de amidoamina. Example 4. Evaluation of the penetration of the modified asphalt with the amidoamine product.
a) La penetración del asfalto modificado se evaluó tal como se indica en el ejemplo 1.  a) The penetration of the modified asphalt was evaluated as indicated in example 1.
Tabla 6. Penetración de Asfalto Modificado
Figure imgf000017_0001
Table 6. Modified Asphalt Penetration
Figure imgf000017_0001
Los resultados muestran, que el asfalto modificado tiene menor penetración que el blanco, y se pueden apreciar gráficamente en la Figura 4. The results show that the modified asphalt has less penetration than the target, and can be seen graphically in Figure 4.
Ejemplo 5. Evaluación de las propiedades reológicas del asfalto modificado. Example 5. Evaluation of the rheological properties of modified asphalt.
a) Se evaluaron las propiedades reológicas del asfalto modificado como se indica en el ejemplo 1.  a) The rheological properties of the modified asphalt were evaluated as indicated in example 1.
Tabla 7. Pro iedades Reoló icas de Asfalto Modificado Table 7. Rheological Properties of Modified Asphalt
Figure imgf000017_0002
Figure imgf000017_0002
En los resultados obtenidos, se puede observar que en el asfalto modificado, el PG se mantiene constante después del proceso de envejecimiento, a diferencia del blanco, en el cual, el PG cambia de 64 a 70. Esto indica que el asfalto modificado se endurece menos que el blanco, lo que lo hace ser un asfalto más joven y que conserva sus propiedades reológicas al paso del tiempo. Los resultados de módulo reológico y ángulo de fase indican que el asfalto modificado se endurece menos que el blanco. esto se ve reflejado en la temperatura de falla, de lo que se concluye que el asfalto modificado tiene menor tendencia al envejecimiento. In the results obtained, it can be seen that in the modified asphalt, the PG remains constant after the aging process, unlike the white, in which the PG changes from 64 to 70. This indicates that the modified asphalt hardens less than white, which makes it a younger asphalt and retains its rheological properties over time. The results of rheological module and phase angle indicate that the modified asphalt hardens less than the target. This is reflected in the fault temperature, from which it is concluded that the modified asphalt has a lower tendency to aging.
Ejemplo 6. Elaboración de una mezcla asfáltica preparada con asfalto modificado con el compuesto de amidoamina de la presente invención. Example 6. Preparation of an asphalt mixture prepared with modified asphalt with the amidoamine compound of the present invention.
La mezcla asfáltica se preparó de acuerdo al diseño de mezcla asfáltica de granulometría densa de alto desempeño del protocolo AMAAC PA- A-001/2008.  The asphalt mix was prepared according to the high performance dense granulometry asphalt mix design of the AMAAC PA-A-001/2008 protocol.
a) Se calentó el asfalto modificado a una temperatura de 140°C.  a) The modified asphalt was heated to a temperature of 140 ° C.
b) Se realizó una mezcla con agregado pétreo en donde el porcentaje final de los componentes a) Asfalto modificado fue de 6% y b) Agregado pétreo fue de 94%.  b) A mixture was made with stone aggregate where the final percentage of the components a) Modified asphalt was 6% and b) Stone aggregate was 94%.
c) Se agitó la mezcla hasta recubrir completamente el agregado pétreo.  c) The mixture was stirred until the stone aggregate was completely covered.
Ejemplo 7. Evaluación del porcentaje de desprendimiento por fricción en Da mezcla asfáltica. Example 7. Evaluation of the percentage of friction detachment in asphalt mixture.
a) La evaluación del porcentaje de desprendimiento se realizó tal como en el ejemplo 1.  a) The evaluation of the percentage of detachment was performed as in example 1.
Tabla 8. Desprendimiento por fricción de Asfalto Modificado
Figure imgf000018_0001
Table 8. Friction of Modified Asphalt
Figure imgf000018_0001
1* Agregado pétreo de regular adherencia 1 * Stone aggregate of regular adhesion
2** Agregado pétreo de mala adherencia  2 ** Stony aggregate of poor adhesion
El porcentaje de desprendimiento por fricción obtenido con el asfalto modificado, es de 0.1% para agregado pétreo con regular adherencia y de 3.1% para agregado pétreo con mala adherencia, en el blanco los porcentajes de desprendimiento por fricción son de 15.7% y 55.5% respectivamente como se muestra en la Tabla 8. De lo anterior, se concluye que el compuesto de amidoamina de la presente invención, se comporta como promotor de adherencia entre el agregado pétreo y el asfalto. Ejemplo 8. Evaluación de la conservación del módulo de resiliencia de Da mezcla asfáltica preparada con asfalto modificado. The percentage of friction detachment obtained with the modified asphalt is 0.1% for stone aggregate with regular adhesion and 3.1% for stone aggregate with poor adhesion, on the white the friction detachment percentages are 15.7% and 55.5% respectively as shown in Table 8. From the foregoing, it is concluded that the amidoamine compound of the present invention behaves as an adhesion promoter between the stone aggregate and the asphalt. Example 8. Evaluation of the conservation of the resilience module of Da asphalt mixture prepared with modified asphalt.
a) Se evalúo la conservación del módulo de resiliencia como se indica en el ejemplo 1, utilizando asfalto modificado con el compuesto de amidoamina de la presente invención, en lugar de asfalto virgen.  a) The conservation of the resilience module was evaluated as indicated in example 1, using modified asphalt with the amidoamine compound of the present invention, instead of virgin asphalt.
En la Tabla 9 se observa que la amplitud entre los módulos de resiliencia medidos para la mezcla asfáltica preparada con asfalto modificado es significativamente menor que la amplitud de los módulos de resiliencia medidos para una mezcla asfáltica blanco. Por lo que se dice que la mezcla asfáltica preparada con asfalto modificado conserva el módulo de resiliencia a diferentes temperaturas de mezclado y compactación, y por tanto se conservan sus propiedades mecánicas.  Table 9 shows that the amplitude between the resilience modules measured for the asphalt mixture prepared with modified asphalt is significantly less than the amplitude of the resilience modules measured for a white asphalt mixture. Therefore, it is said that the asphalt mixture prepared with modified asphalt preserves the modulus of resilience at different mixing and compaction temperatures, and therefore its mechanical properties are preserved.
Tabla 9. Conservación del módulo de resiliencia a diferentes temperaturas de compactación Table 9. Conservation of the resilience module at different compaction temperatures
Figure imgf000019_0001
Figure imgf000019_0001
La Figura 5 muestra gráficamente la conservación del módulo de resiliencia. Figure 5 graphically shows the conservation of the resilience module.

Claims

REIVINDICACIONES Habiendo descrito suficientemente la invención, la considero como una novedad y por lo tanto reclamo como de mi exclusiva propiedad, lo contenido en las siguientes reivindicaciones. CLAIMS Having sufficiently described the invention, I consider it as a novelty and therefore claim as my exclusive property, what is contained in the following claims.
1. Un compuesto de amidoamina para modificar la viscosidad del asfalto, promover la adherencia entre el agregado pétreo y el asfalto, prevenir el envejecimiento del asfalto y conservar el módulo de resiliencia de la mezcla asfáltica a diferentes temperaturas de compactación, caracterizado por la siguiente fórmula química:
Figure imgf000020_0001
1. An amidoamine compound to modify the viscosity of the asphalt, promote the adhesion between the stone aggregate and the asphalt, prevent the aging of the asphalt and preserve the resilience module of the asphalt mixture at different compaction temperatures, characterized by the following formula chemistry:
Figure imgf000020_0001
que es obtenido a partir de: a) Mezclar BHMT (bis-hexametilentriamina) y triestearato de glicenlo en una relación estequiometria, sub-estequiométrica y sobre-estequionmétrica. b) Calentar la mezcla de 2 a 6 horas a una temperatura desde 150°C hasta 220°C, para llevar a cabo la reacción entre los reactivos.  which is obtained from: a) Mix BHMT (bis-hexamethylenetriamine) and glycenyl triestearate in a stoichiometric, sub-stoichiometric and over-stoichiometric ratio. b) Heat the mixture for 2 to 6 hours at a temperature from 150 ° C to 220 ° C, to carry out the reaction between the reagents.
c) Detener el calentamiento hasta lograr una temperatura ambiente, para detener la reacción.  c) Stop heating until room temperature is achieved, to stop the reaction.
2. Un asfalto modificado que consiste en a) Asfalto y b) el compuesto de amidoamina de la fórmula (I):
Figure imgf000020_0002
2. A modified asphalt consisting of a) Asphalt and b) the amidoamine compound of the formula (I):
Figure imgf000020_0002
(I) El asfalto modificado de conformidad con la reivindicación 2 en donde el compuesto de amidoamina de la fórmula (I) se encuentra preferentemente en un porcentaje desde 1% y hasta 6% con respecto al peso del asfalto. (I) The modified asphalt according to claim 2 wherein the amidoamine compound of the formula (I) is preferably in a percentage from 1% to 6% with respect to the weight of the asphalt.
El asfalto modificado de conformidad con la reivindicación 2 o 3 en donde el compuesto de amidoamina de la fórmula (I) se encuentra más preferentemente en un porcentaje 3% con respecto el peso del asfalto. The modified asphalt according to claim 2 or 3 wherein the amidoamine compound of the formula (I) is more preferably in a percentage 3% with respect to the weight of the asphalt.
Una mezcla asfáltica que consiste en a) Agregado pétreo y b) Asfalto modificado con el compuesto de amidoamina de la fórmula (I). An asphalt mixture consisting of a) Stone aggregate and b) Modified asphalt with the amidoamine compound of the formula (I).
La mezcla asfáltica de la reivindicación 5 en donde el agregado pétreo se encuentra preferentemente en un porcentaje desde 92% y hasta 96.5% y el asfalto modificado con el compuesto de amidoamina de la fórmula (I) en un porcentaje desde 3.5% y hasta 8%. The asphalt mixture of claim 5 wherein the stone aggregate is preferably in a percentage from 92% to 96.5% and the modified asphalt with the amidoamine compound of the formula (I) in a percentage from 3.5% to 8% .
La mezcla asfáltica de conformidad con la reivindicaciones 5 o 6 en donde el agregado pétreo se encuentra más preferentemente en un porcentaje del 94% y el asfalto modificado con el compuesto de amidoamina de la fórmula (I) en un porcentaje del 6%. The asphalt mixture according to claims 5 or 6 wherein the stone aggregate is more preferably in a percentage of 94% and the modified asphalt with the amidoamine compound of the formula (I) in a percentage of 6%.
La mezcla asfáltica de conformidad con las reivindicaciones 5, 6 o 7 en donde el asfalto modificado comprende preferentemente el compuesto de amidoamina de la fórmula (I) en un porcentaje desde 1% y hasta 6% con respecto al peso del asfalto. The asphalt mixture according to claims 5, 6 or 7 wherein the modified asphalt preferably comprises the amidoamine compound of the formula (I) in a percentage from 1% and up to 6% with respect to the weight of the asphalt.
La mezcla asfáltica de conformidad con las reivindicaciones 5, 6, 7 u 8 en donde el asfalto modificado comprende más preferentemente el compuesto de amidoamina de la fórmula (I) en un porcentaje de 3% con respecto al peso del asfalto. The asphalt mixture according to claims 5, 6, 7 or 8 wherein the modified asphalt most preferably comprises the amidoamine compound of the formula (I) in a percentage of 3% with respect to the weight of the asphalt.
10. Un proceso para fabricar un asfalto modificado que consiste en a) Asfalto y b) el compuesto de amidoamina de la fórmula (I) que consiste en: a) Calentar el asfalto a una temperatura de entre 90°C y 140°C. 10. A process for manufacturing a modified asphalt consisting of a) Asphalt and b) the amidoamine compound of the formula (I) consisting of: a) Heating the asphalt at a temperature between 90 ° C and 140 ° C.
b) Adicionar el compuesto de amidoamina de la fórmula (I).  b) Add the amidoamine compound of the formula (I).
c) Agitar hasta lograr una mezcla homogénea.  c) Stir until a homogeneous mixture is achieved.
11. El proceso de conformidad con la reivindicación 10 en donde el compuesto de amidoamina se encuentra preferentemente en un porcentaje desde 1% y hasta 6% con respecto al peso del asfalto. 11. The process according to claim 10 wherein the amidoamine compound is preferably in a percentage from 1% to 6% with respect to the weight of the asphalt.
12. El proceso de conformidad con la reivindicación 11 en donde el coimpuesto de amidoamina se encuentre más preferentemente en un porcentaje ele 3% con respecto al peso del asfalto. 12. The process according to claim 11 wherein the amidoamine co-compound is more preferably in a percentage of 3% with respect to the weight of the asphalt.
13. Un proceso para fabricar una mezcla asfáltica que consiste en a) Agregado pétreo y b) Asfalto modificado con el compuesto de amidoamina de la formula (I), que consiste en: a) Calentar el asfalto modificado a una temperatura de entre 90°C y 140°C. 13. A process for manufacturing an asphalt mixture consisting of a) Stone aggregate and b) Modified asphalt with the amidoamine compound of formula (I), which consists of: a) Heating the modified asphalt at a temperature between 90 ° C and 140 ° C.
b) Realizar una mezcla con agregado pétreo en donde el porcentaje final de los componentes a) Asfalto modificado es desde 3.5% y hasta 8% y b) Agregado pétreo es desde 92% y hasta 96.5%. b) Make a mixture with stone aggregate where the final percentage of the components a) Modified asphalt is from 3.5% and up to 8% and b) Stone aggregate is from 92% and up to 96.5%.
c) Agitar la mezcla hasta recubrir completamente el agregado pétreo. c) Stir the mixture until the stone aggregate is completely covered.
14. El proceso de conformidad con la reivindicación 13 en donde el asfalto modificado se encuentra preferentemente en un porcentaje de 6% y el agregado pétreo se encuentra preferentemente en un porcentaje de 94%. 14. The process according to claim 13 wherein the modified asphalt is preferably in a percentage of 6% and the stone aggregate is preferably in a percentage of 94%.
15. El proceso de conformidad con la reivindicación 14 en donde el asfalto modificado tiene un porcentaje preferentemente desde 1% y hasta 6% del compuesto de amidoamina de la fórmula (I) con respecto al peso del asfalto. 15. The process according to claim 14 wherein the modified asphalt preferably has a percentage from 1% to 6% of the amidoamine compound of the formula (I) with respect to the weight of the asphalt.
16. El proceso de conformidad con la reivindicación 15 en donde el asfalto modificado tiene un porcentaje más preferentemente de 3% del compuesto de amidoamina de la fórmula (I) con respecto al peso del asfalto. 16. The process according to claim 15 wherein the modified asphalt has a more preferably 3% percentage of the amidoamine compound of the formula (I) with respect to the weight of the asphalt.
17. El uso del compuesto de amidoamina de la fórmula (I) en asfaltos para modificar la viscosidad, promover la adherencia entre el agregado pétreo y el asfalto, prevenir el envejecimiento del asfalto o conservar las propiedades mecánicas del asfalto en mezclas tibias para pavimentación. 17. The use of the amidoamine compound of the formula (I) on asphalts to modify viscosity, promote adhesion between stone aggregate and asphalt, prevent asphalt aging or preserve the mechanical properties of asphalt in warm paving mixtures.
. El uso del compuesto de amidoamina de la fórmula (I) en productos de pavimentación que presenten asfalto. . The use of the amidoamine compound of the formula (I) in asphalt paving products.
PCT/MX2011/000133 2011-09-09 2011-11-07 Amidoamine compounds, modified asphalts, warm mixtures, methods for the production thereof and the use thereof WO2013036095A1 (en)

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MX2011009504A MX2011009504A (en) 2011-09-09 2011-09-09 Amidoamine compounds, modified asphalts, warm mixtures and the manufacture and use thereof.

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Publication number Priority date Publication date Assignee Title
US9212159B1 (en) 2015-02-09 2015-12-15 King Fahd University Of Petroleum And Minerals Nitrated and amine-reacted asphaltenes

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FR2598630A1 (en) * 1986-05-14 1987-11-20 Elsamex Sa New emulsifier for asphalt emulsions based on modified bitumens and process for its manufature
WO2000068329A1 (en) * 1999-05-10 2000-11-16 Goldschmidt Chemical Company Road repair methods and fast breaking asphalt emulsion compositions useful therewith
EP1063263B1 (en) * 1999-06-24 2005-02-16 Toho Chemical Industry Co., Ltd. Method of preparing heating type paving material and composition used therefor
ES2251342T3 (en) * 1999-12-09 2006-05-01 Cognis Ip Management Gmbh USE OF EMULGENTS IN BITUMINOUS EMULSION.
DE102009059149A1 (en) * 2009-05-04 2010-11-18 Heinrichs, Annette, Dr. Composition, useful e.g. as solvent pastes, comprises e.g. diaminediamide long-chain carboxylic acids, diamine monoamide, basic reaction products of e.g. dialkyldiamines, polyamines and/or alkanolamines, and free long chain carboxylic acid

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2598630A1 (en) * 1986-05-14 1987-11-20 Elsamex Sa New emulsifier for asphalt emulsions based on modified bitumens and process for its manufature
WO2000068329A1 (en) * 1999-05-10 2000-11-16 Goldschmidt Chemical Company Road repair methods and fast breaking asphalt emulsion compositions useful therewith
EP1063263B1 (en) * 1999-06-24 2005-02-16 Toho Chemical Industry Co., Ltd. Method of preparing heating type paving material and composition used therefor
ES2251342T3 (en) * 1999-12-09 2006-05-01 Cognis Ip Management Gmbh USE OF EMULGENTS IN BITUMINOUS EMULSION.
DE102009059149A1 (en) * 2009-05-04 2010-11-18 Heinrichs, Annette, Dr. Composition, useful e.g. as solvent pastes, comprises e.g. diaminediamide long-chain carboxylic acids, diamine monoamide, basic reaction products of e.g. dialkyldiamines, polyamines and/or alkanolamines, and free long chain carboxylic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9212159B1 (en) 2015-02-09 2015-12-15 King Fahd University Of Petroleum And Minerals Nitrated and amine-reacted asphaltenes

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CO6710938A2 (en) 2013-07-15
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