Asphalt regeneration agent, recycled asphalt composition containing the same, method for producing the same, and uses thereof

Abstract

We provide a deteriorated asphalt regeneration agent consisting of compounds derived from renewable resources. [Solution] The regenerating agent is a compound represented by formula (1). TIFF2026166728000021.tif36154 [In the formula, group R is independently a hydrogen atom, an alkyl group, an alkylcarbonyl group, formula (2): TIFF2026166728000022.tif28154 Selected from the group consisting of acyl groups represented by [the formula shown].

Description

[Technical Field]

[0001] This invention relates to a deteriorated asphalt regenerating agent (deteriorated asphalt regenerating additive) added to regenerate (or restore) deteriorated asphalt, a regenerated asphalt composition containing the same, a method for producing the same, and their uses. Furthermore, this invention relates to an asphalt deterioration inhibitor for suppressing the deterioration of asphalt, an asphalt composition containing the same, and their uses. [Background technology]

[0002] Over time, asphalt deteriorates, losing its viscoelasticity, becoming hard and brittle, and leading to problems such as cracking. Asphalt in this deteriorated, hard, and brittle state (hereinafter referred to as "deteriorated asphalt") is recycled and reused as recycled asphalt.

[0003] The recycling process for deteriorated asphalt generally involves adding a deteriorated asphalt recycling additive (deteriorated asphalt recycling agent) to the recovered and finely crushed asphalt waste material before (or after) heat softening treatment. The deteriorated asphalt recycling agent works to restore the viscoelasticity (penetration and elongation) of the deteriorated asphalt contained in the asphalt waste material.

[0004] Conventionally, petroleum-derived asphalt regenerators such as naphthenic crude oil, polymerized oil, and wax have been used as asphalt regenerators due to their compatibility with asphalt and ease of manufacture.

[0005] For example, Japanese Patent Publication No. 7195083 (Patent Document 1) describes a predetermined kinematic viscosity at 100°C, aniline point, and %C obtained by ring analysis (ndM method). A It has a pour point and is derived from naphthenic crude oil, and has a predetermined aniline point and %C by ring analysis (ndM method). A An additive for regenerating deteriorated asphalt derived from H-type modified asphalt is described, comprising a low-aniline point aromatic oil having [specific properties].

[0006] However, the petroleum-derived additive for recycling deteriorated asphalt described in Patent Document 1 tends to have limited use due to its reliance on finite resources and the limited areas from which it can be extracted. Therefore, in order to realize a decarbonized society, there is a need for a deteriorated asphalt recycling agent derived from renewable resources that can be used sustainably without resource depletion, but such an agent is not yet known.

[0007] Japanese Patent Publication No. 2023-41636 (Patent Document 2) describes a starch-derived asphalt modifier as an asphalt modifier derived from renewable resources.

[0008] Specifically, Patent Document 2 describes an asphalt modifier containing a compound of the following formula.

[0009] [ka]

[0010] (A represents hydrogen or OR, Each R is independently either an acyl group derived from a straight-chain saturated fatty acid with 10 to 22 carbon atoms, or Each R independently consists of hydrogen, a linear alkyl group having 10 to 22 carbon atoms, an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, and the following formula:

[0011] [ka]

[0012] (Selected from the group consisting of acyl groups derived from γ-aminobutyric acid derivatives shown, where n is 8 to 18, and at least one of R is an acyl group derived from the γ-aminobutyric acid derivative.)

[0013] It is described that the asphalt modifier of Patent Document 2 can improve the water resistance and / or non-flowability of asphalt by being added to asphalt. However, Patent Document 2 does not conduct specific verification of using the asphalt modifier as a deteriorated asphalt regenerant.

Prior Art Documents

Patent Documents

[0014]

Patent Document 1

Patent Document 2

Summary of the Invention

Problem to be Solved by the Invention

[0015] Accordingly, an object of the present invention is to provide a deteriorated asphalt regenerant composed of a predetermined compound derived from a renewable resource, a recycled asphalt composition containing the deteriorated asphalt regenerant, a method for producing the recycled asphalt composition, and uses thereof.

[0016] Another object of the present invention is to provide a deteriorated asphalt regenerant which has excellent compatibility with deteriorated asphalt and can regenerate deteriorated asphalt even in a small amount, a recycled asphalt composition containing the deteriorated asphalt regenerant, a method for producing the recycled asphalt composition, and uses thereof.

[0017] Still another object of the present invention is to provide a deteriorated asphalt regenerant which, when added to deteriorated asphalt, suppresses bleed-out over a long period of time and is less likely to change with time, a recycled asphalt composition containing the deteriorated asphalt regenerant, a method for producing the recycled asphalt composition, and uses thereof.

[0018] Another object of the present invention is to provide a method for easily regenerating deteriorated asphalt.

[0019] A further object of the present invention is to provide an asphalt deterioration inhibitor comprising a predetermined compound derived from renewable resources that suppresses the deterioration of asphalt, an asphalt composition containing the asphalt deterioration inhibitor, and uses thereof. [Means for solving the problem]

[0020] As a result of diligent research to achieve the above objectives, the inventors discovered that by combining a predetermined deteriorated asphalt regenerating agent derived from renewable resources with deteriorated asphalt, the deteriorated asphalt can be regenerated, and thus completed the present invention.

[0021] In other words, the present invention includes the following embodiments.

[0022] Embodiment [1]: A deteriorated asphalt regenerating agent derived from renewable resources, which is added to deteriorated asphalt to regenerate the deteriorated asphalt, and comprises a compound represented by the following formula (1).

[0023] [ka]

[0024] [In the formula, group R is independently a hydrogen atom, an alkyl group having 10 or more carbon atoms, an alkylcarbonyl group having 10 or more carbon atoms (or an acyl group derived from a saturated fatty acid with 10 or more carbon atoms (including the carbon atoms of the carboxyl group)), and the following formula (2):

[0025] [ka]

[0026] (In the formula, n represents an integer between 8 and 18.) Selected from the group consisting of acyl groups represented by (or acyl groups derived from γ-aminobutyric acid derivatives), Of the aforementioned groups R, at least one group R is either an alkylcarbonyl group having 10 or more carbon atoms, or an acyl group represented by formula (2). m represents either 0 or 1.

[0027] Embodiment [2]: The deteriorated asphalt regenerator according to Embodiment [1], wherein in formula (1), the alkyl group having 10 or more carbon atoms of group R is a linear alkyl group having 10 to 22 carbon atoms, and the alkylcarbonyl group having 10 or more carbon atoms of group R is a linear alkylcarbonyl group having 10 to 22 carbon atoms.

[0028] Embodiment [3]: In formula (1), group R is (i) independently a linear alkylcarbonyl group having 10 to 22 carbon atoms; or, (ii) The deteriorated asphalt regenerator according to embodiment [1] or [2], wherein at least one of the groups R is an acyl group represented by formula (2).

[0029] Embodiment [4]: ​​A deteriorated asphalt regenerating agent according to any of Embodiments [1] to [3], wherein the formula (1) has one or fewer hydrogen atom groups R.

[0030] Embodiment [5]: In formula (1), the group R is (i) independently a linear alkylcarbonyl group having 12 to 20 carbon atoms; or, (ii) A deteriorated asphalt regenerator according to any of the embodiments [1] to [4], wherein the acyl group is independently represented by formula (2).

[0031] Embodiment [6]: A deteriorated asphalt regenerating agent according to any of Embodiments [1] to [5], wherein n in formula (2) is an integer from 10 to 16.

[0032] Embodiment [7]: A deteriorated asphalt regenerator according to any one of Embodiments [1] to [6], wherein the compound represented by formula (1) is a compound represented by the following formula (3) or (4).

[0033] [ka]

[0034] (In the formula, base R is the same as in formula (1) above)

[0035] [ka]

[0036] (In the formula, base R is the same as in formula (1) above)

[0037] Embodiment [8]: A recycled asphalt composition comprising at least deteriorated asphalt and a deteriorated asphalt regenerating agent according to any of Embodiments [1] to [7].

[0038] Embodiment [9]: The recycled asphalt composition according to Embodiment [8], wherein the ratio of the deteriorated asphalt regenerator to 100 parts by mass of deteriorated asphalt is 0.05 to 50 parts by mass.

[0039] Embodiment

[10] : The recycled asphalt composition according to Embodiment [8] or [9], wherein the compound represented by formula (1) forms a fibrous phase (or fibrous phase).

[0040] Embodiment

[11] : A method for producing the recycled asphalt composition described in Embodiment

[10] by heating and mixing at least deteriorated asphalt with a deteriorated asphalt regenerating agent described in any of Embodiments [1] to [7].

[0041] Embodiment

[12] : A method for regenerating deteriorated asphalt by adding a deteriorated asphalt regenerating agent described in any of Embodiments [1] to [7] to deteriorated asphalt.

[0042] In this method, at least the deteriorated asphalt and the deteriorated asphalt regenerating agent may be heated and mixed together.

[0043] Embodiment

[13] : An asphalt deterioration inhibitor derived from renewable resources, which is added to asphalt to suppress or prevent the deterioration of the asphalt, and comprises a compound represented by the following formula (1).

[0044] [ka]

[0045] [In the formula, group R is independently a hydrogen atom, an alkyl group having 10 or more carbon atoms, an alkylcarbonyl group having 10 or more carbon atoms, and the following formula (2):

[0046] [ka]

[0047] (In the formula, n represents an integer between 8 and 18.) Selected from the group consisting of acyl groups represented by, Of the aforementioned groups R, at least one group R is either an alkylcarbonyl group having 10 or more carbon atoms, or an acyl group represented by formula (2). m represents either 0 or 1.

[0048] In formula (1) above, the alkyl group having 10 or more carbon atoms in group R may be a linear alkyl group having 10 to 22 carbon atoms, and the alkylcarbonyl group having 10 or more carbon atoms in group R may be a linear alkylcarbonyl group having 10 to 22 carbon atoms.

[0049] Embodiment

[14] : An asphalt composition comprising at least asphalt and the asphalt deterioration inhibitor described in Embodiment

[13] .

[0050] Embodiment

[15] : The asphalt composition according to Embodiment

[14] , wherein the ratio of the asphalt deterioration inhibitor to 100 parts by mass of asphalt is 0.05 to 50 parts by mass.

[0051] In the asphalt composition, the compound represented by formula (1) may form a fibrous phase.

[0052] Furthermore, the asphalt composition may be manufactured by heating and mixing at least asphalt and the asphalt deterioration inhibitor.

[0053] Embodiment

[16] : A method for suppressing the deterioration of asphalt by adding the asphalt deterioration inhibitor described in Embodiment

[13] to asphalt.

[0054] In this method, the asphalt deterioration inhibitor may be added to the asphalt and heated and stirred to suppress the deterioration of the asphalt.

[0055] In this specification and in the claims, the term “asphalt” may include both “new, undegraded asphalt” (virgin asphalt or new material) and “degraded asphalt,” but it more often means “new, undegraded asphalt” (virgin asphalt or new material).

[0056] In this specification and in the claims, the term "degraded asphalt" is used synonymously with "degraded asphalt," "degraded asphalt," etc.

[0057] In this specification and in the claims, the term “renewable resources” means resources that are regenerated in natural cycles and can be sustainably utilized. Typical renewable resources are organic resources (biological resources) derived from living organisms (animals and plants) that can be regenerated (reused or replenished), and unlike fossil fuels (oil, coal, natural gas, etc.), which are depletable resources, they can be used indefinitely.

[0058] In this specification and in the claims, the "number of carbon atoms" in "linear saturated fatty acid having X to Y carbon atoms" means the number of carbon atoms including the carbon atoms of the carboxyl group of the fatty acid. [Effects of the Invention]

[0059] In this invention, a predetermined deteriorated asphalt regenerating agent derived from renewable resources is added to deteriorated asphalt, thereby enabling the regeneration of deteriorated asphalt (or restoring the penetration and elongation, which have decreased due to deterioration, to a level that makes it recyclable).

[0060] Furthermore, because the deteriorated asphalt regenerating agent of the present invention has excellent compatibility with deteriorated asphalt, it can efficiently regenerate deteriorated asphalt even with a small amount of additive. Therefore, in a regenerated asphalt composition containing deteriorated asphalt and the deteriorated asphalt regenerating agent, the bleed-out of the deteriorated asphalt regenerating agent is suppressed over a long period of time, and it is less susceptible to changes over time.

[0061] In this invention, a recycled asphalt composition can be easily manufactured simply by heating and mixing deteriorated asphalt with the deteriorated asphalt regenerating agent, and the deteriorated asphalt can be effectively recycled.

[0062] Furthermore, the deteriorated asphalt regenerating agent of the present invention can also be used as an asphalt deterioration inhibitor to suppress (or slow down) the deterioration of asphalt (especially virgin asphalt), and the deterioration of asphalt can be effectively suppressed or prevented simply by adding it to asphalt (especially virgin asphalt) and heating and mixing it. [Brief explanation of the drawing]

[0063] [Figure 1] Figure 1 is a graph showing the relationship between the accelerated heating period and the proportion of asphaltene in Examples 1-4 and Comparative Example 1. [Figure 2] Figure 2 shows the AFM image of virgin asphalt in Comparative Example 1-1. [Figure 3] Figure 3 shows AFM images of deteriorated asphalt in Comparative Examples 1-6. [Figure 4] Figure 4 shows AFM images of the recycled asphalt compositions (first asphalt composition) prepared in Examples 1-6. [Figure 5]Figure 5 shows AFM images of the recycled asphalt compositions (first asphalt compositions) prepared in Examples 2-6. [Figure 6] Figure 6 shows AFM images of the recycled asphalt compositions (first asphalt compositions) prepared in Examples 3-6. [Figure 7] Figure 7 shows AFM images of the recycled asphalt compositions (first asphalt compositions) prepared in Examples 4-6. [Modes for carrying out the invention]

[0064] Asphalt can be divided into four components according to its molecular weight: saturated material, aromatic material, resinous material, and asphaltene material. When asphalt deteriorates, the proportion of asphaltene material increases, and the asphaltene material aggregates or crosslinks, causing deteriorated asphalt to become hard and brittle.

[0065] The mechanism by which the deteriorated asphalt regenerating agent of the present invention can regenerate deteriorated asphalt is unknown, but it can be presumed as follows.

[0066] In other words, when the deteriorated asphalt regenerating agent of the present invention (hereinafter sometimes simply referred to as "regenerating agent") is added to deteriorated asphalt in a state where asphalten has aggregated, and heated and mixed, the regenerating agent, due to its excellent compatibility with asphalt, is uniformly dispersed in the deteriorated asphalt. Subsequently, as the temperature decreases, the uniformly dispersed regenerating agent spontaneously self-assembles and grows into fibrous structures in a specific direction (or having orientation), forming a structure in which the fibers intertwine, and forming a structure [fibrous phase (fibrous phase, dispersed phase, or regenerating agent phase)] that is phase-separated from the deteriorated asphalt (or matrix) phase formed by the deteriorated asphalt [forming a complexly intertwined fibrous phase (fibrous structure or fibrous aggregate (three-dimensional network structure)) throughout the deteriorated asphalt]. It is presumed that the fibers of this fibrous phase penetrate the aggregated asphalten (lumps) and peel off (separate or dissociate) the lumps, thereby softening the hardened asphalt.

[0067] Normally, when fibrous materials (such as conventional regenerating agents) are added to asphalt and dispersed, the fibers interfere with (contact with) each other and become entangled, making uniform dispersion or distribution difficult and resulting in variations in the degree of regeneration. However, the deteriorated asphalt regenerating agent of the present invention can spontaneously form fibers as the temperature decreases after heating at a predetermined temperature (self-assembling to form a fibrous phase in the asphalt phase formed by deteriorated asphalt), thus enabling the formation of uniformly distributed fibers (fibrous structures or fiber aggregates) in the asphalt and homogeneously softening the asphaltene agglutinations.

[0068] [Asphalt Regeneration Agent] The deteriorated asphalt regenerating agent of the present invention is a deteriorated asphalt regenerating agent derived from renewable resources that is added to deteriorated asphalt to regenerate it, and is of the following formula (1):

[0069] [ka]

[0070] [In the formula, group R is independently a hydrogen atom, an alkyl group having 10 or more carbon atoms, an alkylcarbonyl group having 10 or more carbon atoms, and the following formula (2):

[0071] [ka]

[0072] (In the formula, n represents an integer between 8 and 18.) Selected from the group consisting of acyl groups represented by, Of the aforementioned groups R, at least one group R is either an alkylcarbonyl group having 10 or more carbon atoms, or an acyl group represented by formula (2). m represents either 0 or 1. It is a compound represented by [formula].

[0073] Examples of the alkyl group (linear or branched alkyl group) having 10 or more carbon atoms for group R include linear or branched C such as decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, icosyl group (eicosyl group), heneicosyl group (henicosyl group), and docosyl group 10-22 alkyl group, preferably linear or branched C 12-20 alkyl group, more preferably linear or branched C 14-20 alkyl group, still more preferably linear or branched C 16-18 alkyl group (in particular, linear C such as hexadecyl group and octadecyl group 16-18 alkyl group) and the like.

[0074] The alkylcarbonyl group having 10 or more carbon atoms (the number of carbon atoms including the carbon atom of the carbonyl group) for group R (acyl group derived from a saturated fatty acid (linear or branched saturated fatty acid) having 10 or more carbon atoms (the number of carbon atoms including the carbon atom of the carboxyl group) (R 1 COOH)) (R 1 CO-) is, for example, decanoic acid (capric acid), undecanoic acid (undecylic acid, undecanoic acid), dodecanoic acid (lauric acid), tridecanoic acid (tridecylic acid, tridecanoic acid), tetradecanoic acid (myristic acid), pentadecanoic acid (pentadecylic acid), hexadecanoic acid (palmitic acid), heptadecanoic acid (margaric acid), octadecanoic acid (stearic acid), nonadecanoic acid (nonadecylic acid), icosanoic acid (arachidic acid, eicosanoic acid), linear or branched C such as heneicosanoic acid (heneicosylic acid, heneicosanoic acid) and docosanoic acid (behenic acid) 10-22 saturated fatty acid, preferably linear or branched C 12-20 saturated fatty acid, more preferably linear or branched C 14-20 saturated fatty acid, still more preferably linear or branched C 16-18 saturated fatty acid (in particular, linear C such as hexadecanoic acid (palmitic acid) and octadecanoic acid (stearic acid) 16-18 saturated fatty acid)-derived acyl group and the like.

[0075] In equation (2) above, n is an integer between 8 and 18, preferably between 10 and 16, and more preferably between 12 and 16.

[0076] That is, the acyl group represented by formula (2) (γ-aminobutyric acid (GABA) derivative represented by formula (2) (R 2 (R) Acyl group derived from C(=O)NH(CH2)3COOH 2 Examples of C(=O)NH(CH2)3CO- include 4-[(1-oxononyl)amino]butanoic acid, 4-[(1-oxodecyl)amino]butanoic acid, 4-[(1-oxoundecyl)amino]butanoic acid, 4-[(1-oxododecyl)amino]butanoic acid, 4-[(1-oxotridecyl)amino]butanoic acid, 4-[(1-oxotetradecyl)amino]butanoic acid, 4-[(1-oxopentadecyl)amino]butanoic acid, 4-[(1-oxohexadecyl)amino]butanoic acid, 4-[(1-oxoheptadecyl)amino]butanoic acid, 4-[(1-oxooctadecyl)amino]butanoic acid, and 4-[(1-oxononadecyl)amino]butanoic acid. 14-24 Examples include acyl groups derived from GABA derivatives (where n in formula (2) is an integer from 8 to 18), and preferably C 16-22 An acyl group derived from a GABA derivative (where n is an integer from 10 to 16), more preferably a C such as 4-[(1-oxotetradecyl)amino]butanoic acid. 18-22 This is an acyl group derived from a GABA derivative (where n is an integer between 12 and 16).

[0077] Typical R groups include linear C groups such as hexadecanoic acid (palmitic acid) and octadecanoic acid (stearic acid). 16-18 Acyl groups corresponding to saturated fatty acids, such as 4-[(1-oxotetradecyl)amino]butanoic acid, etc. 18-22 Examples include acyl groups derived from GABA derivatives.

[0078] The four bases R (five bases R if m is 1) in formula (1) may be the same or different from each other, but it is preferable that they are all the same.

[0079] The compound represented by formula (1) (hereinafter sometimes simply referred to as "compound (1)") may be any compound in which at least one group R is either an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, or an acyl group derived from a γ-aminobutyric acid derivative represented by formula (2). For example, the group R may be (i) independently an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, or (ii) at least one of the groups R is an acyl group derived from the γ-aminobutyric acid derivative.

[0080] Furthermore, in compound (1), the number of hydrogen atom-representing groups R among the four groups R (five groups R if m is 1) is, for example, two or less, preferably one or less (i.e., 0 or 1), and especially 0. A small number of hydrogen atom-representing groups R increases hydrophobicity, improves compatibility with asphalt, and facilitates crystallization, making separation and purification easier, which is advantageous.

[0081] In other words, in compound (1), group R is (i) independently an acyl group (linear alkylcarbonyl group) derived from a linear saturated fatty acid having 10 to 22 carbon atoms, or (ii) independently selected from the group consisting of a linear alkyl group having 10 to 22 carbon atoms, an acyl group derived from a linear saturated fatty acid having 10 to 22 carbon atoms, and an acyl group derived from a γ-aminobutyric acid derivative represented by formula (2) (n is an integer from 8 to 18), and preferably at least one group R is an acyl group derived from the γ-aminobutyric acid derivative (n is an integer from 8 to 18);

[0082] More preferably, group R is (i) independently an acyl group (linear alkylcarbonyl group) derived from a linear saturated fatty acid having 10 to 22 carbon atoms (e.g., 12 to 20 carbon atoms), or (ii) independently an acyl group derived from a γ-aminobutyric acid derivative represented by formula (2) (where n is an integer from 8 to 18);

[0083] More preferably, group R is (i) an acyl group derived from the same linear saturated fatty acid having 10 to 22 carbon atoms (for example, 12 to 20, preferably 14 to 20), or (ii) an acyl group derived from the same γ-aminobutyric acid derivative represented by formula (2) (where n is an integer from 8 to 18, preferably an integer from 10 to 16).

[0084] In formula (1) above, m represents 0 or 1. When m is 0 (i.e., unsubstituted or with a hydrogen atom bonded), compound (1) is 1,5-anhydroglucitol or its derivatives, or stereoisomers (enantiomers, diastereomers) thereof. When m is 1, compound (1) is glucopyranose or its derivatives, or stereoisomers (enantiomers, diastereomers) thereof.

[0085] Of these compounds (1), it is preferable that they are 1,5-anhydro-D-glucitol (1,5-AG) represented by the following formula (3) or its derivatives, or D-glucopyranose (Glc) represented by the following formula (4) or its derivatives, or stereoisomers thereof, due to their naturally occurring nature, lack of reducing properties, and stability.

[0086] [ka]

[0087] (In the formula, base R is the same as in formula (1) above)

[0088] [ka]

[0089] (In the formula, base R is the same as in formula (1) above)

[0090] Representative compounds (1) include 1,5-anhydro-D-glucitol-2,3,4,6-O-tetrapalmitate, in which the group R in formula (3) is an acyl group derived from the same C16 linear saturated fatty acid [hexadecanoic acid (palmitic acid)]; 1,5-anhydro-D-glucitol-2,3,4,6-O-tetrastearate, in which the group R in formula (3) is an acyl group derived from the same C18 linear saturated fatty acid [octadecanoic acid (stearic acid)]; and 1,5-anhydro-2,3,4,6-tetra-O-{4-[(1-oxotetradecyl)amino]butanoyl}-D-glucitol, in which the group R in formula (3) is an acyl group derived from the same γ-aminobutyric acid derivative (n is 14) [4-[(1-oxotetradecyl)amino]butanoic acid].

[0091] The compound (1) may be synthesized by a general method, for example, by a method described in Japanese Patent Publication No. 6952305.

[0092] [asphalt] The type of asphalt is not particularly limited and includes common asphalts such as natural asphalt (e.g., lake asphalt, rock asphalt, oil sand, asphaltite, etc.) and petroleum asphalt (e.g., straight asphalt, blown asphalt, etc.). These asphalts can be used alone or in combination of two or more types. Of these asphalts, straight asphalt is preferred.

[0093] The aforementioned asphalt may be used as modified asphalt by combining it with a modifier. The modifier includes organic modifiers and inorganic modifiers.

[0094] Examples of organic modifiers include polyolefins, vinyl polymers (e.g., polyvinyl chloride, acrylic resin, polyvinyl acetate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, ethylene-acrylic acid copolymer, ethylene-methyl acrylate copolymer, ethylene-ethyl acrylate copolymer, etc.), polyamides, polyesters, synthetic rubber or elastomers (e.g., polybutadiene, polyisoprene, styrene-butadiene copolymers such as styrene-butadiene-styrene block copolymer, etc.), natural rubber, tackifiers (e.g., terpene resins, rosin resins such as natural rosin and modified rosin, petroleum resins, modified olefin polymers, etc.), and oils and fats (e.g., naphthenic raw material oils, etc.). These organic modifiers can be used individually or in combination of two or more.

[0095] Examples of inorganic modifiers include metal particles (powder) such as iron, copper, tin, zinc, nickel, and stainless steel; metal oxide particles such as iron oxide, iron(III) oxide, iron(III) oxide, ferrite, tin oxide, zinc oxide, zinc oxide, copper oxide, and aluminum oxide; metal salt particles such as barium sulfate, calcium sulfate, aluminum sulfate, calcium sulfite, calcium carbonate, calcium bicarbonate, barium carbonate, and magnesium hydroxide; mineral particles such as steelmaking slag, slate chips, mica, clay, talc, wollastonite, diatomaceous earth, silica sand, pumice powder, silica balloons, glass balloons, and shirasu balloons; and inorganic fibers such as glass fibers and carbon fibers. These inorganic modifiers can be used individually or in combination of two or more.

[0096] Among these modifiers, organic modifiers such as elastomers (thermoplastic elastomers), tackifiers, and oils and fats are preferred, and styrene-diene copolymers such as styrene-butadiene-styrene block copolymers are particularly preferred.

[0097] The proportion of asphaltene in asphalt (virgin asphalt) can be selected from a range of approximately 5 to 35% by mass, according to the Japan Petroleum Institute standard: JPI-5S-70-2010 (Asphalt composition analysis test method by TLC / FID method), for example, 10 to 30% by mass, preferably 12 to 25% by mass.

[0098] The penetration (1 / 10 mm) of asphalt (initial asphalt) can be selected from a range of approximately 0 to 300 according to the method in accordance with JIS K 2207-1996, for example, 20 to 200, preferably 40 to 120, and more preferably 60 to 80.

[0099] The softening point of asphalt (virgin asphalt) can be selected from a range of approximately 20 to 200°C according to the method in accordance with JIS K 2207-1996, for example, 25 to 150°C, preferably 30 to 100°C, and more preferably 40 to 60°C.

[0100] [Deteriorated asphalt] As mentioned above, when asphalt deteriorates, the proportion of asphaltene, one of the four components of asphalt, increases, and the asphaltene aggregates or crosslinks. As a result, deteriorated asphalt becomes hard and brittle, and its penetration decreases.

[0101] The proportion of asphaltene in deteriorated asphalt is about 5% by mass more than that of virgin asphalt or initial asphalt, according to the method conforming to the standards of the Japan Petroleum Institute, for example, about 15% by mass or more, preferably 22% by mass or more, and more preferably 30% by mass or more (for example, about 30 to 50% by mass).

[0102] Furthermore, the penetration of deteriorated asphalt (1 / 10 mm) is approximately 10 or less, for example, 7 or less, preferably 5 or less, according to a method compliant with JIS K 2207-1996.

[0103] In this specification and in the claims, deteriorated asphalt may be asphalt with an asphaltene content of 25% by mass or more and a penetration (1 / 10 mm) of 7 or less.

[0104] [Recycled asphalt composition (first asphalt composition)] The present invention includes compositions (recycled asphalt compositions, first asphalt compositions) that include at least deteriorated asphalt and a deteriorated asphalt regenerating agent.

[0105] Normally, if the compatibility between asphalt and the additive added to the asphalt is poor, a large amount of the additive will be required, which raises concerns about the additive bleeding out. However, the deteriorated asphalt regenerating agent of the present invention (particularly compound (1)) has excellent compatibility with deteriorated asphalt, so even a small amount of additive can effectively act on the deteriorated asphalt and regenerate it without bleeding out.

[0106] The proportion of the deteriorated asphalt regenerating agent (particularly compound (1)) may be, for example, about 0.05 to 50 parts by mass per 100 parts by mass of deteriorated asphalt, preferably 0.1 to 40 parts by mass, more preferably 0.5 to 30 parts by mass, more preferably 1 to 20 parts by mass, and most preferably 5 to 15 parts by mass. Furthermore, the proportion of the deteriorated asphalt regenerating agent (particularly compound (1)) in the recycled asphalt composition may be, for example, 0.01 to 50% by mass, preferably 0.05 to 40% by mass, more preferably 0.1 to 30% by mass, more preferably 0.5 to 20% by mass, and most preferably 1 to 15% by mass. If the proportion of the deteriorated asphalt regenerating agent is too small, it may not be able to exert its effect as a regenerating agent, and if it is too large, the regenerating agent may not be able to be sufficiently dispersed and dissolved.

[0107] The recycled asphalt composition may, in addition to deteriorated asphalt and the regenerating agent, contain other components, such as other regenerating agents (second regenerating agents) that have the function of regenerating deteriorated asphalt (second regenerating agent), or conventional additives, as long as the effects of the present invention are not impaired.

[0108] Other regenerating agents (secondary regenerating agents) include, for example, petroleum-derived regenerating agents such as naphthenic crude oil, polymerized oil, and wax. These other regenerating agents can be used individually or in combination of two or more.

[0109] The proportion of other regenerating agents (second regenerating agents) is, for example, 20% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less (for example, 0.1 to 3% by mass) in the deteriorated asphalt composition.

[0110] Conventional additives can be used, such as stabilizers (heat stabilizers, UV absorbers, light stabilizers, antioxidants, etc.), thickeners, flame retardants, plasticizers, antistatic agents, colorants, surfactants, dispersants, lubricants, crystallization rate retarders, lubricants, antimicrobial agents, insecticides (anticides, mite repellents, etc.), preservatives (fungicides, etc.), matting agents, heat storage agents, fragrances, fluorescent whitening agents, wetting agents, and fillers. These additives can be used individually or in combination of two or more.

[0111] The total proportion of additives may be less than 50 parts by mass per 100 parts by mass of the deteriorated asphalt composition, preferably 40 parts by mass or less, more preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and most preferably 10 parts by mass or less (for example, 0.1 to 5 parts by mass).

[0112] As described above, the deteriorated asphalt regenerating agent of the present invention (particularly compound (1)) has excellent compatibility with deteriorated asphalt, and is therefore easily and uniformly dispersed in deteriorated asphalt, yielding a homogeneous composition (regenerated asphalt composition, first asphalt composition).

[0113] When such a recycled asphalt composition is heated to a predetermined temperature, as the temperature subsequently decreases, the deteriorated asphalt regenerating agent (particularly compound (1)) in the composition self-assembles to form a complexly intertwined fibrous phase (fibrous structure, fibrous aggregate) (or is distributed in a fibrous manner), resulting in a composition in which fibers are uniformly distributed without uneven distribution within the deteriorated asphalt (a composition in which compound (1) is fibrous). In other words, in a composition in which the deteriorated asphalt regenerating agent (particularly compound (1)) forms a fibrous phase, the asphaltene agglutinations (aggregates) are decomposed or dissociated, making the composition more flexible.

[0114] Normally, when fibrous materials are added to asphalt and dispersed or distributed within the asphalt, the fibers become entangled, making uniform dispersion difficult. However, the homogeneous recycled asphalt composition of the present invention (first asphalt composition) can be recycled for various applications and has high practicality.

[0115] In the recycled asphalt composition of the present invention, the degraded asphalt regenerating agent (particularly compound (1)) spontaneously self-assembles and grows fibrously in a specific direction, forming a structure in which the fibers are intertwined, and forming a structure [fibrous phase (fibrous phase, dispersed phase, or regenerating agent phase)] that is phase-separated from the degraded asphalt (or matrix) phase formed by the degraded asphalt. That is, the fibers are formed with orientation and, in the composition, form a fibrous aggregate (fibrous phase) that maintains uniform (approximately uniform) spacing without clumping. Such fibers are long fibers with an average fiber length based on atomic force microscopy (AFM) images of, for example, 50 μm or more, preferably 70 μm or more, and more preferably 100 μm or more. The average fiber diameter is, for example, 10 to 500 nm, preferably 30 to 400 nm, and more preferably 50 to 300 nm.

[0116] The average fiber length and average fiber diameter can be calculated as the average value of 10 points based on atomic force microscope (AFM) images of the composition.

[0117] The ratio of the average fiber length to the average fiber diameter (average fiber length / average fiber diameter) of the aforementioned fibers may be, for example, 10 or more, preferably 15 or more, and more preferably 20 or more (for example, 100 or more). In the present invention, the regenerating agent may self-assemble to form long fibers and create a three-dimensional network structure.

[0118] [Method for producing recycled asphalt composition] Such recycled asphalt compositions (first asphalt compositions) can be produced by adding the deteriorated asphalt regenerating agent to deteriorated asphalt, and in particular, recycled asphalt compositions in which the compound (1) is distributed in a fibrous manner (forming a fibrous phase) can be produced by heating and mixing (kneading) at least the deteriorated asphalt and the deteriorated asphalt regenerating agent. That is, the method for producing the recycled asphalt composition (recycled asphalt composition in which the compound (1) is distributed in a fibrous manner) only needs to include at least a mixing step of mixing the regenerating agent and deteriorated asphalt, and a heating step of heating the deteriorated asphalt.

[0119] In the mixing step, a desired amount of the regenerating agent can be added to the deteriorated asphalt and mixed using a general method, for example, by using a mixing device such as a mixer.

[0120] In the heating step, the heating temperature may be, for example, around 70 to 250°C, preferably 80 to 170°C, and more preferably 90 to 160°C (for example, 100 to 150°C). The heating time may be, for example, around 10 minutes to 2 hours, preferably 15 minutes to 1.5 hours, and more preferably 20 minutes to 1 hour.

[0121] The deteriorated asphalt regenerating agent of the present invention (compound (1)) is heated to a predetermined temperature, and then self-assembles to form fibers (or a fibrous phase) as the temperature decreases (or cools). The heated deteriorated asphalt regenerating agent (compound (1)) may be cooled by air cooling, and the cooling rate may be controlled. The cooling rate is, for example, 1 to 8°C / min, preferably 1.5 to 7.5°C / min (for example, 2 to 7°C / min), and more preferably about 3 to 6°C / min. The cooling rate may be the average cooling rate during the cooling operation, or for example, the rate obtained by dividing the change in temperature from the end of heating to the end of cooling (usually room temperature) by the total cooling time. Air cooling (natural cooling) is preferred.

[0122] The recycled asphalt composition of the present invention may be manufactured in the order of the mixing step followed by the heating step, or in the order of the heating step followed by the mixing step. When the recycled asphalt composition is manufactured in the order of the heating step followed by the mixing step, it is preferable that the mixing step be performed simultaneously (or nearly simultaneously) with the heating step in order to effectively utilize the spontaneous fiber-forming ability of the regenerating agent (particularly compound (1)).

[0123] Specifically, the recycled asphalt composition of the present invention (first asphalt composition) may be manufactured by adding (pre-adding) the regenerating agent to non-degraded asphalt (virgin asphalt, new material, or non-degraded asphalt), mixing it, and then heating it when the asphalt has deteriorated, thereby changing the regenerating agent into a fibrous form; or it may be manufactured by heating deteriorated asphalt, adding and mixing the regenerating agent, particularly adding (post-adding) it almost simultaneously with the heating operation in the heating step, and mixing it, thereby changing the regenerating agent into a fibrous form.

[0124] The recycled asphalt composition of the present invention can be manufactured by a simple operation of heating and mixing (or kneading) by utilizing the spontaneous fiber-forming ability of the regenerating agent (particularly compound (1)), and offers excellent productivity.

[0125] [Asphalt deterioration inhibitor] Thus, the deteriorated asphalt regenerating agent of the present invention is applied to deteriorated asphalt and exhibits the effect of regenerating deteriorated asphalt, but is not limited to deteriorated asphalt and may be applied to non-deteriorated (or any) asphalt (especially virgin asphalt, new material, or non-deteriorated asphalt). When the deteriorated asphalt regenerating agent of the present invention is applied to asphalt or non-deteriorated asphalt (especially virgin asphalt), the deterioration of the asphalt can be suppressed (the rate of deterioration can be reduced).

[0126] The mechanism by which the deteriorated asphalt regenerating agent of the present invention (particularly compound (1)) can suppress the deterioration of asphalt is unknown, but it can be presumed as follows.

[0127] In other words, when the regenerating agent of the present invention (particularly compound (1)) is added to early-stage asphalt that has not deteriorated significantly (non-deteriorated asphalt) and heated and mixed, compound (1) is uniformly dispersed (or dissolved) in the asphalt. Subsequently, as the temperature decreases, the dispersed compound (1) spontaneously self-assembles in the asphalt to form fibers (fibrous structure) in a specific direction (or having orientation) throughout the asphalt. That is, the self-assembly of compound (1) in the asphalt phase forms a phase separation structure and forms a fibrous phase (fibrous phase, dispersed phase, or deterioration inhibitor phase) [forming intricately intertwined fibers (fibrous structure or fibrous aggregate (three-dimensional network structure)) throughout the asphalt]. Therefore, it can be estimated that the aggregation of asphaltene, which occurs with the deterioration of asphalt, is inhibited, making it difficult for agglomerates to form.

[0128] Therefore, it can be said that the deteriorated asphalt regeneration agent of the present invention also acts as an asphalt deterioration inhibitor (hereinafter sometimes simply referred to as "deterioration inhibitor").

[0129] In other words, the present invention includes an asphalt deterioration inhibitor comprising a compound represented by formula (1).

[0130] The compound represented by formula (1) contained in the asphalt deterioration inhibitor is the same as compound (1) which is the deteriorated asphalt regenerator, including in preferred embodiments.

[0131] [Asphalt composition (second asphalt composition)] The present invention encompasses compositions (asphalt composition, second asphalt composition) comprising at least asphalt (particularly virgin asphalt, new material, or non-degraded asphalt) and the asphalt degradation inhibitor.

[0132] In this specification and in the claims, "non-degraded asphalt" means asphalt that has not deteriorated, and is not limited to asphalt that has never been recycled (also called virgin asphalt, neat asphalt, initial asphalt, or new material asphalt), but also includes asphalt that has properties substantially equivalent to those of asphalt that has never been recycled.

[0133] In this specification and in the claims, non-degraded asphalt may be asphalt having an asphaltene content of less than 25% by mass and a penetration (1 / 10 mm) of 60 to 80.

[0134] As described above, the asphalt deterioration inhibitor of the present invention (particularly compound (1)) has excellent compatibility with asphalt, so the amount added may be small, and the proportion of the deterioration inhibitor (particularly compound (1)) may be, for example, about 0.05 to 50 parts by mass per 100 parts by mass of asphalt, preferably 0.1 to 40 parts by mass, more preferably 0.5 to 30 parts by mass, more preferably 1 to 20 parts by mass, and most preferably 5 to 15 parts by mass. Furthermore, the proportion of the asphalt deterioration inhibitor (particularly compound (1)) in the asphalt composition is, for example, 0.01 to 50% by mass, preferably 0.05 to 40% by mass, more preferably 0.1 to 30% by mass, more preferably 0.5 to 20% by mass, and most preferably 1 to 15% by mass. If the proportion of the deterioration inhibitor is too small, there is a risk that deterioration will not be sufficiently suppressed, and if it is too large, there is a risk that the deterioration inhibitor will not dissolve sufficiently.

[0135] The (second) asphalt composition may, in addition to asphalt and the deterioration inhibitor, contain other components, such as other deterioration inhibitors (second deterioration inhibitors) that have the function of suppressing the deterioration of asphalt (second deterioration inhibitors), or conventional additives, as long as they do not impair the effects of the present invention.

[0136] Other degradation inhibitors (second degradation inhibitors) include, for example, the degradation inhibitors exemplified as other regenerating agents (second regenerating agents). These other degradation inhibitors can be used individually or in combination of two or more.

[0137] The proportion of other deterioration inhibitors (second deterioration inhibitors) in the asphalt composition is, for example, 20% by mass or less, preferably 10% by mass or less, preferably 5% by mass or less (for example, 0.1 to 3% by mass).

[0138] Conventional additives can be used, such as those exemplified in the section on [Recycled Asphalt Composition (First Asphalt Composition)]. These additives can be used individually or in combination of two or more.

[0139] The total proportion of additives may be less than 50 parts by mass per 100 parts by mass of asphalt composition, preferably 40 parts by mass or less, more preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and most preferably 10 parts by mass or less (for example, 0.1 to 5 parts by mass).

[0140] Similar to the regenerating agent, the deterioration inhibitor of the present invention (particularly compound (1)) exhibits excellent compatibility with asphalt, is easily and uniformly dispersed in asphalt, and yields a homogeneous composition (asphalt composition, second asphalt composition).

[0141] When such a (second) asphalt composition is heated to a predetermined temperature, as the temperature subsequently decreases, the deterioration inhibitor in the composition (particularly compound (1)) self-assembles and grows in a fibrous manner in a specific direction, forming a structure in which the fibers are intertwined, and a structure [fibrous phase (fibrous phase, dispersed phase, or deterioration-inhibiting phase)] is formed that is phase-separated from the asphalt (or matrix) phase, resulting in a composition in which the fibers are uniformly distributed without uneven distribution in the asphalt phase (the fibers maintain even spacing) (a composition in which a fibrous phase has been formed). In such a composition in which a fibrous phase of compound (1) has been formed, the aggregation of asphaltene is inhibited, and the deterioration of asphalt is suppressed.

[0142] The average fiber length, average fiber diameter, and ratio of average fiber length to average fiber diameter (average fiber length / average fiber diameter) of the aforementioned fibers are the same as, including preferred embodiments, the average fiber length, average fiber diameter, and ratio of average fiber length to average fiber diameter (average fiber length / average fiber diameter) of the fibers contained in the recycled asphalt composition.

[0143] [(Second) method for producing asphalt composition] The asphalt composition (second asphalt composition) can also be produced by adding the asphalt deterioration inhibitor to at least asphalt, and in particular, the asphalt composition in which compound (1) is fibrous can be produced by heating and mixing (kneading) at least the asphalt and the asphalt deterioration inhibitor. That is, the method for producing the asphalt composition (asphalt composition in which compound (1) is fibrous) only needs to include at least a mixing step of mixing the deterioration inhibitor and asphalt, and a heating step of heating the asphalt.

[0144] The mixing method in the mixing step, the heating temperature and heating time in the heating step are the same as those for the method of producing the recycled asphalt composition, including preferred embodiments. The (second) asphalt composition of the present invention may be produced in the order of the mixing step followed by the heating step, or in the order of the heating step followed by the mixing step.

[0145] In other words, the asphalt composition of the present invention (the second asphalt composition) may be manufactured by adding the deterioration inhibitor to non-degraded asphalt (virgin asphalt, initial asphalt, new material, or non-degraded asphalt) (first-addition), mixing, and heating to form a fibrous phase of the deterioration inhibitor; or by adding the deterioration inhibitor to virgin asphalt when heating (last-addition), mixing, and forming a fibrous phase of the deterioration inhibitor.

[0146] [Methods for restoring deteriorated asphalt and methods for suppressing asphalt deterioration] The present invention also includes a method for regenerating deteriorated asphalt by adding the deteriorated asphalt regenerating agent to deteriorated asphalt, and a method for suppressing the deterioration of asphalt by adding the asphalt deterioration inhibitor to asphalt.

[0147] In the above-mentioned regeneration method, the deteriorated asphalt regeneration agent and the deteriorated asphalt may be heated and mixed, and in the above-mentioned deterioration suppression method, the asphalt deterioration suppressor and the asphalt may be heated and mixed.

[0148] These methods utilize the property that compound (1) self-assembles to form fibers as the temperature decreases after heating, thereby enabling the simple regeneration of deteriorated asphalt or the suppression of asphalt deterioration.

[0149] Furthermore, the criteria for determining whether deteriorated asphalt has been regenerated (or restored) may be, for example, by measuring parameters that change with the deterioration of asphalt (e.g., the proportion of asphaltene in the asphalt and the degree of penetration) and comparing them with the parameters of virgin asphalt that has not deteriorated, in order to determine whether the deteriorated asphalt has been regenerated (or restored).

[0150] For example, if the proportion of asphaltene in deteriorated asphalt is set to 100, and the proportion of asphaltene after adding the regenerating agent to the deteriorated asphalt and heating and mixing at 130°C for 30 minutes is, for example, 100 or less, preferably 90 or less, and more preferably 80 or less, then it may be determined that the deteriorated asphalt has been regenerated (or recovered).

[0151] Furthermore, if the penetration degree (1 / 10 mm) of deteriorated asphalt is set to 100, and the penetration degree (1 / 10 mm) after adding the regenerating agent to the deteriorated asphalt and heating and mixing at 130°C for 30 minutes is, for example, 100 or more, preferably 150 or more, and even more preferably 200 or more, then it may be determined that the deteriorated asphalt has been regenerated (or recovered).

[0152] Furthermore, the degree of regeneration (or recovery) in deteriorated asphalt can also be confirmed by observing the asphalt with an AFM (atomic force microscope). When asphalt is observed with an AFM, structures derived from asphaltene (Bee structures, rod-shaped structures with white and black stripes) can be observed, and it is known that these Bee structures elongate and increase in number as the asphalt deteriorates. Therefore, the degree of regeneration (or recovery) can be judged by the degree of elongation and number of Bee structures observed with an AFM.

[0153] In this specification and in the claims, the asphaltene content, penetration, and AFM (atomic force microscope) observations can be measured or evaluated by the methods described in the examples below. [Examples]

[0154] The present invention will be described in more detail below based on examples, but the present invention is not limited to these examples. Details of the materials of the recycled asphalt composition (first asphalt composition) used in the examples, the method for preparing the deteriorated asphalt, and the method for evaluating the degree of asphalt deterioration are shown below.

[0155] [Materials for recycled asphalt composition] Straight Asphalt: Idemitsu Kosan Co., Ltd. "Straight Asphalt 60-80", Penetration (25℃) 71 (1 / 10 mm), Softening Point 46.0℃, Elongation (15℃) 100+ cm (100 cm or more), Toluene Soluble Content 99.82% Degraded asphalt regenerating agent A: C16AG (1,5-anhydro-D-glucitol-2,3,4,6-O-tetrapalmitate) synthesized in accordance with the method described in Japanese Patent Publication No. 6952305. Degraded asphalt regeneration agent B: C18AG (1,5-anhydro-D-glucitol-2,3,4,6-O-tetrastearate) synthesized in accordance with the method described in Japanese Patent Publication No. 6952305.

[0156] [Preparation of deteriorated asphalt] Degraded asphalt was prepared by heating straight asphalt to 80°C to accelerate its deterioration. The heating period to accelerate deterioration (accelerated heating time) was set to 0 (virgin asphalt), 30, 60, 90, 120, and 180 days, and deteriorated asphalt with different degrees of deterioration was prepared.

[0157] [Method for evaluating the degree of asphalt deterioration] <Percentage of asphaltene content> In accordance with the Petroleum Institute Standard: JPI-5S-70-2010 (Test Method for Asphalt Composition Analysis by TLC / FID Method), the respective contents of 4 components (saturates, aromatics, resins and asphaltenes) contained in asphalt were measured, and the degree of deterioration was evaluated by the degree of increase in the proportion of asphaltenes.

[0158] <Penetration> Penetration was measured in accordance with JIS K 2207:1996, and the degree of deterioration was evaluated by the degree of decrease in penetration.

[0159] <AFM Observation> AFM observation was performed using AFM (MFP-3D-BIO tapping mode, manufactured by Oxford Instruments) and a cantilever (OMCL-AC24OTS-W2, manufactured by Olympus Corporation), and the degree of deterioration was evaluated by the degree of elongation of the Bee structure and the increase in its number.

[0160] [Example 1 (Example 1-1 to Example 1-6)] A mixture obtained by adding deteriorated asphalt regenerant A to about 30 g of each of 6 types of deteriorated asphalt with different accelerated heating periods so as to be 5% by mass in the regenerated asphalt composition was heated and mixed at 130°C for 30 minutes, and allowed to cool to prepare a regenerated asphalt composition, and the proportion of asphaltenes and the penetration [penetration of Example 1-6 (accelerated heating period 180 days)] were measured.

[0161] [Example 2 (Example 2-1 to Example 2-6)] A regenerated asphalt composition was prepared in the same manner as in Example 1, except that the proportion of the deteriorated asphalt regenerant A was changed to 10% by mass, and the proportion of asphaltenes and the penetration [penetration of Example 2-6 (accelerated heating period 180 days)] were measured.

[0162] [Example 3 (Example 3-1 to Example 3-6)] A recycled asphalt composition was prepared in the same manner as in Example 1, except that deteriorated asphalt regenerator B was added to the recycled asphalt composition in a manner that made up 5% by mass, instead of deteriorated asphalt regenerator A. The proportion of asphaltene and the degree of penetration [degree of penetration in Examples 3-6 (accelerated heating period of 180 days)] were measured.

[0163] [Example 4 (Examples 4-1 to 4-6)] A recycled asphalt composition was prepared in the same manner as in Example 3, except that the proportion of deteriorated asphalt regenerating agent B was changed to 10% by mass, and the proportion of asphaltene and the penetration rate [penetration rate for Examples 4-6 (accelerated heating period of 180 days)] were measured.

[0164] [Comparative Example 1 (Comparative Example 1-1 to Comparative Example 1-6)] Without adding a deteriorated asphalt regeneration agent, approximately 30g each of six deteriorated asphalts with different accelerated heating periods was heated and mixed at 130°C for 30 minutes, as in Example 1, then allowed to cool, and the proportion of asphaltene and the degree of penetration [penetration degree for Comparative Examples 1-6 (accelerated heating period of 180 days)] were measured.

[0165] Table 1 summarizes the details of the recycled asphalt compositions prepared in Comparative Example 1 and Examples 1-4, and their correspondence to the numbers of the Comparative Examples and Examples.

[0166] [Table 1]

[0167] Figure 1 shows a graph illustrating the relationship between the accelerated heating period and the proportion of asphaltene in Examples 1-4 and Comparative Example 1, and Table 2 shows the penetration rates for Examples 1-6, 2-6, 3-6, 4-6, and Comparative Example 1-6.

[0168] Furthermore, AFM observation was performed to observe the condition of the virgin asphalt of Comparative Example 1-1, the deteriorated asphalt of Comparative Example 1-6, and the recycled asphalt compositions prepared in Examples 1-6, 2-6, 3-6, and 4-6, and to evaluate the degree of deterioration.

[0169] Since it is difficult to directly observe the prepared recycled asphalt composition using AFM, a sample for AFM observation was prepared as follows and considered equivalent to the prepared asphalt composition.

[0170] Small amounts of virgin asphalt from Comparative Example 1-1 (accelerated heating period 0 days), deteriorated asphalt from Comparative Example 1-6 (accelerated heating period 180 days), and the pre-heating mixtures from Examples 1-6, 2-6, 3-6, and 4-6 were placed on a glass slide as samples and heated on a hot plate at 130°C for several minutes. The heated samples were spread thinly with a spatula and left at room temperature for 24 hours or more, after which AFM observation was performed. The results are shown in Figures 2-7.

[0171] [Table 2]

[0172] As is clear from Figure 1, in Comparative Example 1, the asphaltene content increased in proportion to the accelerated heating period, and in particular, the asphaltene content increased sharply during the accelerated heating period of 180 days.

[0173] In Examples 1-4, the proportion of asphaltene in each recycled asphalt composition sample using deteriorated asphalt with different accelerated heating periods (30, 60, 90, 120, and 180 days) was approximately the same as that of virgin asphalt (accelerated heating period of 0 days), suggesting that it had recovered to a level equivalent to virgin asphalt. Furthermore, in Examples 1-4, even the deteriorated asphalt with an accelerated heating period of 180 days, which showed a rapid increase in the proportion of asphaltene in Comparative Example 1, exhibited a proportion of asphaltene equivalent to that of virgin asphalt. Moreover, the results of Examples 1-4 showed similar behavior, and no significant differences were observed depending on the type and addition ratio of the deteriorated asphalt regenerator. From the above, it can be said that deteriorated asphalt regenerators A and B function as regenerators for deteriorated asphalt.

[0174] Furthermore, as is clear from Table 2, the penetration depth recovered more significantly in the examples than in the comparative examples, indicating that the deteriorated asphalt was regenerated. No significant differences were observed depending on the type of regenerating agent, suggesting that regenerating agents A and B function as regenerating agents for deteriorated asphalt. While the penetration depth decreased slightly with higher additive ratios even when using the same regenerating agent, this is likely due to an increase in fibrous structures as the additive ratio of the regenerating agent increased, and the degree of deteriorated asphalt regeneration is considered to be roughly the same.

[0175] Furthermore, as is clear from Figures 2-7, when comparing Comparative Example 1-1 and Comparative Example 1-6, the Bee structure (a rod-shaped structure with white and black stripes in the figure, derived from asphaltene) is elongated and its number increases, indicating deterioration of the asphalt. However, no clear Bee structure was observed in Examples 1-6, 2-6, 3-6, and 4-6.

[0176] Furthermore, in Examples 1-6, 2-6, 3-6, and 4-6, a three-dimensionally intertwined fibrous phase was observed in regenerators A and B, with an average fiber diameter of 100-200 nm. This was more pronounced in Examples 1-6 and 2-6, which used regenerator A. This suggests that regenerator A had superior compatibility with deteriorated asphalt compared to regenerator B, resulting in more uniform and higher-concentration fiber formation. No significant differences were observed in the degree of asphalt deterioration depending on the type and proportion of regenerator. Therefore, it can be concluded that deteriorated asphalt regenerators A and B function as regenerators for deteriorated asphalt.

[0177] Therefore, based on the proportion of asphaltene, the degree of penetration, and all the results of AFM observation, it can be said that deteriorated asphalt regenerators A and B function as regenerators for deteriorated asphalt. [Industrial applicability]

[0178] The deteriorated asphalt regenerating agent of the present invention can regenerate deteriorated asphalt and can be used as a regenerating agent applicable to various types of asphalt. The deteriorated asphalt regenerating agent of the present invention can also be applied to virgin asphalt that has not deteriorated, and is useful as an asphalt deterioration inhibitor that suppresses or prevents asphalt deterioration. Therefore, deteriorated asphalt can be effectively recycled, reducing the consumption of limited resources and mitigating the burden on the environment.

Claims

1. A deteriorated asphalt regenerating agent derived from renewable resources, which is added to deteriorated asphalt to regenerate the deteriorated asphalt, and comprises a compound represented by the following formula (1). 【Chemistry 1】 [In the formula, group R is independently a hydrogen atom, an alkyl group having 10 or more carbon atoms, an alkylcarbonyl group having 10 or more carbon atoms, and the following formula (2): 【Chemistry 2】 (In the formula, n represents an integer between 8 and 18.) Selected from the group consisting of acyl groups represented by, Of the aforementioned groups R, at least one group R is either an alkylcarbonyl group having 10 or more carbon atoms, or an acyl group represented by formula (2). [m represents 0 or 1]

2. The deteriorated asphalt regenerator according to claim 1, wherein in formula (1), the alkyl group having 10 or more carbon atoms of group R is a linear alkyl group having 10 to 22 carbon atoms, and the alkylcarbonyl group having 10 or more carbon atoms of group R is a linear alkylcarbonyl group having 10 to 22 carbon atoms.

3. In formula (1) above, group R is (i) independently a linear alkylcarbonyl group having 10 to 22 carbon atoms; or, (ii) The deteriorated asphalt regenerator according to claim 1 or 2, wherein at least one of the groups R is an acyl group represented by formula (2).

4. The deteriorated asphalt regenerating agent according to claim 1 or 2, wherein the group R representing a hydrogen atom in formula (1) is one or less.

5. In formula (1) above, group R is (i) independently a linear alkylcarbonyl group having 12 to 20 carbon atoms; or, (ii) The deteriorated asphalt regenerator according to claim 1 or 2, which independently comprises an acyl group represented by formula (2).

6. The deteriorated asphalt regenerating agent according to claim 1 or 2, wherein in formula (2), n is an integer from 10 to 16.

7. The deteriorated asphalt regenerator according to claim 1 or 2, wherein the compound represented by formula (1) is a compound represented by the following formula (3) or (4). 【Transformation 3】 (In the formula, base R is the same as in formula (1) above.) 【Chemistry 4】 (In the formula, base R is the same as in formula (1) above.)

8. A recycled asphalt composition comprising at least deteriorated asphalt and the deteriorated asphalt regenerating agent according to claim 1 or 2.

9. The recycled asphalt composition according to claim 8, wherein the ratio of the deteriorated asphalt regenerator to 100 parts by mass of deteriorated asphalt is 0.05 to 50 parts by mass.

10. The recycled asphalt composition according to claim 8, wherein the compound represented by formula (1) forms a fibrous phase.

11. A method for producing the recycled asphalt composition according to claim 10, comprising heating and mixing at least deteriorated asphalt with the deteriorated asphalt regenerating agent according to claim 1 or 2.

12. A method for regenerating deteriorated asphalt by adding the deteriorated asphalt regenerating agent described in claim 1 or 2 to deteriorated asphalt.

13. An asphalt deterioration inhibitor derived from renewable resources, which is added to asphalt to suppress or prevent the deterioration of said asphalt, and comprises a compound represented by the following formula (1). 【Transformation 5】 [In the formula, group R is independently a hydrogen atom, an alkyl group having 10 or more carbon atoms, an alkylcarbonyl group having 10 or more carbon atoms, and the following formula (2): 【Transformation 6】 (In the formula, n represents an integer between 8 and 18.) Selected from the group consisting of acyl groups represented by, Of the aforementioned groups R, at least one group R is either an alkylcarbonyl group having 10 or more carbon atoms, or an acyl group represented by formula (2). [m represents 0 or 1]

14. An asphalt composition comprising at least asphalt and the asphalt deterioration inhibitor described in claim 13.

15. The asphalt composition according to claim 14, wherein the ratio of the asphalt deterioration inhibitor to 100 parts by mass of the asphalt is 0.05 to 50 parts by mass.

16. A method for suppressing the deterioration of asphalt by adding the asphalt deterioration inhibitor described in claim 13 to asphalt.

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