WO2016121580A1

WO2016121580A1 - Asphalt additive

Info

Publication number: WO2016121580A1
Application number: PCT/JP2016/051467
Authority: WO
Inventors: 板橋　太門; 悠太菊地
Original assignee: 住友化学株式会社
Priority date: 2015-01-30
Filing date: 2016-01-19
Publication date: 2016-08-04
Also published as: TW201634552A; JPWO2016121580A1

Abstract

The invention pertains to an additive for asphalt to be used for laying down the roadway of an asphalt pavement. The invention provides an asphalt mixture for a roadway pavement, an asphalt composition, and an asphalt additive with which it is possible to reduce the viscosity of the asphalt and the temperature when the asphalt and an aggregate are mixed and when the asphalt mixture is laid, and with which an asphalt pavement having exceptional stability in the laid-down roadway can be obtained.

Description

Additive for asphalt

This patent application claims priority with respect to Japanese Patent Application No. 2015-016954 (filing date: January 30, 2015), which is hereby incorporated by reference in its entirety. Shall be incorporated.
The present invention relates to an additive for asphalt used for road construction of asphalt pavement. Here, asphalt relates to asphalt used for asphalt pavement.

When implementing road construction of asphalt pavement, asphalt is heated and mixed with aggregates at the asphalt mixing station to form an asphalt mixture, and then transported to the construction site for use. In general, asphalt has a property that the viscosity changes depending on the temperature, and the viscosity decreases as the temperature increases, but the viscosity increases and the fluidity decreases as the temperature decreases. Asphalt needs to have a sufficiently low viscosity when it is heated and mixed at an asphalt mixing station or when it is applied to roads, so the temperature during mixing and construction is set appropriately depending on the type of asphalt. There is a need.

When mixing straight asphalt and aggregate, heating mixing at the asphalt mixing station is performed at around 160 ° C., and the operation temperature at the installation site is 110 ° C. to 150 ° C. Therefore, although the asphalt mixture is shipped from the asphalt mixing place at a temperature of around 160 ° C., the viscosity is lowered by being cooled while being transported to the construction place. In addition, it is known that asphalt is likely to be deteriorated by heating, and deteriorated asphalt is deteriorated in performance after construction, especially stability and aggregate grasping power, and its viscosity is increased. It is preferable to heat mix at a temperature as low as possible or to perform construction so as not to cause excessive deterioration.

In heavy traffic routes, asphalt paved roads with improved stability against asphalt paved roads, straight asphalt modified with polymers such as SBS (styrene / butadiene / styrene block copolymer) (modified asphalt H type, etc.) Is used. Modified asphalt has a higher viscosity than straight asphalt and needs to be heat mixed with the aggregate at a higher temperature than straight asphalt. When using the modified asphalt H type, the heating and mixing temperature is usually about 170 ° C. to 180 ° C., and the construction temperature is 140 ° C. to 170 ° C.

Also, in recent years, asphalt has been highly modified by increasing the amount of SBS added to the modified asphalt H type for the purpose of reducing road noise and improving drainage performance and further improving the durability of asphalt pavement. Has also been developed. However, such asphalt is liable to deteriorate because it needs to be heated and mixed at a higher temperature. Therefore, in order to avoid such deterioration, it is required to reduce the viscosity of asphalt without increasing the heating mixing and construction temperature.

Asphalt mixture used for asphalt pavement is repaired because it deteriorates with age, but the asphalt mixture peeled off from the road at that time is recycled. However, asphalt in the asphalt mixture has deteriorated considerably due to repeated recycling of the asphalt mixture, and thus has a much higher viscosity than new asphalt. In addition, reclaimed asphalt mixture was mainly used for straight asphalt, but as a result of repair of pavement using modified asphalt, recycled asphalt was mixed with recycled straight asphalt. In addition, the viscosity of asphalt to be recycled is further increased. Therefore, it is required to reduce the viscosity of asphalt during heating mixing and construction work of asphalt.

Conventionally, as a technique for reducing the viscosity of asphalt, a method of adding an oil component such as mineral oil to the asphalt to reduce the viscosity of the asphalt at a high temperature is known. However, in the method of adding the oil component, the asphalt after the oil component is added becomes soft, so the aggregate grasping power in the asphalt mixture after cooling is reduced, and the road stability after construction is not sufficient. May end up.

Moreover, a method of adding a specific organic foaming agent and a foaming aid as a warming agent has been proposed as a warming technique for lowering the mixing temperature of asphalt mixture materials and the temperature during paving (Patent Document 1). . However, although this method of adding a warming agent can reduce the temperature during mixing, it can only be applied to a method of adding a warming agent in an asphalt mixing station (plant mix method). In the method of adding the warming agent to the asphalt in advance (premix method), foaming occurs when the warming agent is added to the asphalt, and the asphalt cannot be stored, and the subsequent mixing with the aggregate is also possible. It becomes impossible to do. For this reason, the aggregate grasping power in the asphalt mixture is reduced, and the stability of the road after construction is not sufficient.

Furthermore, a method of adding a wax (fatty acid) has also been implemented, but the asphalt pavement obtained by this method is not sufficient in stability and dynamic stability.
JP 2001-131321 A

As described above, techniques for reducing the viscosity of asphalt have been studied in the past, but since all of them deteriorate the workability and various characteristics of the asphalt mixture when added, the mixing temperature of asphalt and aggregate and the asphalt There is a demand for an asphalt additive that can simultaneously achieve the workability at the time of manufacturing the asphalt mixture and the excellent aggregate grasping power after the construction while lowering the temperature during the construction of the mixture.

The present invention reduces the viscosity of asphalt, can reduce the temperature when mixing asphalt and aggregate and when constructing an asphalt mixture, and is excellent in road stability after construction. Asphalt additives, asphalt compositions and road pavement asphalt mixtures are provided.

As a result of intensive investigation on additives for asphalt having an asphalt viscosity reducing effect and excellent aggregate grasping power during construction of asphalt and aggregate by heating and asphalt mixture, the inventors have identified The present inventors have found that the above problem can be solved by the compound represented by the formula:

That is, the present invention includes the following.
[1] An asphalt additive containing a compound represented by the formula (1) or a salt thereof.

[Where,
n and m are each independently an integer of 1 to 20,
l is an integer from 1 to 4,
p and q are each independently 0 or 1,
A ¹ and A ² each independently represent —CO—, —CH ₂ —, —O—, —CO ₂ —, or —OCO—,
R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom or an optionally substituted hydrocarbon group, and R ² and R ³ are bonded to form a cyclic structure. It may be. ]
[2] The asphalt additive according to the above [1], wherein the compound represented by the formula (1) or a salt thereof is the compound represented by the formula (3) or a salt thereof.

[Where,
n and m are each independently an integer of 1 to 20,
p and q are each independently 0 or 1,
A ¹ and A ² each independently represent —CO—, —CH ₂ —, —O—, —CO ₂ —, or —OCO—,
R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom or an optionally substituted hydrocarbon group, and R ² and R ³ are bonded to form a cyclic structure. It may be. ]
[3] The above-mentioned [1], wherein the compound represented by the formula (1) or a salt thereof is a compound represented by the formula (4) or a salt thereof, or a compound represented by the formula (5) or a salt thereof. ] The asphalt additive as described in any one of.

[Where,
t and u are each independently an integer of 2 to 6;
R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom or an optionally substituted hydrocarbon group, and R ² and R ³ are bonded to form a cyclic structure. It may be. ]
[4] The asphalt additive according to the above [1], wherein the compound represented by the formula (1) or a salt thereof is the compound represented by the formula (6) or a salt thereof.

[Where,
t and u are each independently an integer of 2 to 6. ]
[5] The asphalt additive according to any one of [1] to [4], wherein the salt is a carboxylate.
[6] The asphalt additive according to any one of [1] to [5], further including at least one oil selected from the group consisting of petroleum-based blended oils and lubricating oils.
[7] The asphalt additive according to [6], wherein the content of the compound represented by the formula (1) or a salt thereof is 0.01 to 200 parts by weight with respect to 100 parts by weight of the oil.
[8] The asphalt additive according to [6] or [7], further including a surfactant.
[9] The asphalt additive according to [8], wherein the surfactant content is 0.01 to 100 parts by weight with respect to 100 parts by weight of the compound represented by the formula (1) or a salt thereof. .
[10] An asphalt composition containing the asphalt additive according to any one of [1] to [9] above and asphalt.
[11] The asphalt composition according to the above [10], which contains 0.005 to 20 parts by weight of the compound represented by the formula (1) or a salt thereof with respect to 100 parts by weight of asphalt.
[12] An asphalt mixture for road pavement containing the asphalt composition according to [10] or [11] above and an aggregate.
[13] The asphalt mixture according to [12] above, which is produced and applied at a temperature of 100 to 300 ° C.
[14] A pavement comprising the asphalt mixture for road pavement described in [12] or [13].

According to the present invention, the viscosity of the asphalt mixture during mixing of asphalt and aggregate and during asphalt construction can be reduced, and the temperature during mixing of asphalt and aggregate and during asphalt construction is reduced. Can be made. Moreover, since the aggregate grasping power can be improved, an asphalt pavement excellent in road stability after construction can be obtained.

Hereinafter, the present invention will be described in detail.

The asphalt additive of the present invention has the following formula (1):

[Where,
n and m are each independently an integer of 1 to 20, preferably an integer of 2 to 6, more preferably an integer of 2 to 3,
l is an integer of 1 to 4, preferably an integer of 2 to 4, more preferably 2.
p and q are each independently 0 or 1,
A ¹ and ^{A 2} are each _{independently, -CO -, - CH 2 -} , - O -, - CO 2 -, or an -OCO-, preferably -CO-, or -CH ₂ - represents,
R ¹ , R ² , R ³ and R ⁴ each independently represents a hydrogen atom or a hydrocarbon group which may have a substituent, and R ² and R ³ are bonded to form a cyclic structure. May be. ]
Or a salt thereof.

The compound represented by the formula (1) or a salt thereof is preferably the following formula (3):

[Where,
n and m are each independently an integer of 1 to 20, preferably an integer of 2 to 6, more preferably an integer of 2 to 3,
p and q are each independently 0 or 1,
A ¹ and ^{A 2} are each _{independently, -CO -, - CH 2 -} , - O -, - CO 2 -, or an -OCO-, preferably -CO -, - CH ₂ - represents,
R ¹ , R ² , R ³ and R ⁴ each independently represents a hydrogen atom or a hydrocarbon group which may have a substituent, and R ² and R ³ are bonded to form a cyclic structure. May be. ]
Or a salt thereof.

The compound represented by the formula (1) or a salt thereof is more preferably the following formula (4):

And / or formula (5):

[In Formula (4) and Formula (5),
t and u are each independently an integer of 1 to 20, preferably an integer of 2 to 6, more preferably an integer of 2 to 3,
p and q are each independently 0 or 1, preferably 0;
R ¹ , R ² , R ³ and R ⁴ each independently represents a hydrogen atom or a hydrocarbon group which may have a substituent, and R ² and R ³ are bonded to form a cyclic structure. May be. ]
Or a salt thereof.

The compound represented by the formula (1) or a salt thereof is more preferably the following formula (6):

[Where,
t and u are each independently an integer of 1 to 20, preferably an integer of 2 to 6, and more preferably an integer of 2 to 3. ]
Or a salt thereof.

Examples of the hydrocarbon group which may have a substituent in R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ include carbon atoms having 1 to 30 carbon atoms which may have a substituent. A hydrogen group is preferable, a saturated hydrocarbon group or an unsaturated hydrocarbon group may be used, and a linear or branched hydrocarbon group may be used. You may have. Examples of the substituent include a group containing a hetero atom and a halogen atom. The group containing a heteroatom may contain one heteroatom, or may contain the same or different heteroatoms, and examples thereof include a hydroxy group and an alkoxy group having 1 to 20 carbon atoms. Among the above hydrocarbon groups, examples of hydrocarbon groups having 3 to 20 carbon atoms include, for example, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group. Group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, stearyl group, lauryl group, myristyl group, 2-ethylhexyl group, 9-hexadecenyl group, cis-9-octadecyl group Group, 11-octadecenyl group, cis, cis-9,12-octadecadienyl group, 9,12,15-octadecatrienyl group, 6,9,12-octadecatrienyl group, 9,11,13 -Octadecatrienyl group, Octadecatetraenyl group, Eicosenyl group, 11,14-Ai Sadienyl group, 13,16-docosadienyl group, 5,8,11,14-icosatetraenyl group, cis-15-tetradocosaenyl group, eicosapentaenyl group, docosapentaenyl group, docosahexaenyl group, 11 Alkyl or alkenyl groups such as -hydroxy-8-cis-heptadecenyl group, hexylphenyl group, heptylphenyl group, octylphenyl group, nonylphenyl group, decylphenyl group, undecylphenyl group, dodecylphenyl group, tridecylphenyl group An alkylphenyl group such as a tetradecylphenyl group, a pentadecylphenyl group, a hexadecylphenyl group, a heptadecylphenyl group, an octadecylphenyl group, and a phenyl group. Among these, an alkyl group having 3 to 20 carbon atoms, a phenyl group, and an alkylphenyl group having 7 to 18 carbon atoms are preferable, and a linear alkyl group having 6 to 18 carbon atoms is more preferable. Among them, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, and 11-hydroxy-8-cis -Heptadecenyl group is more preferred. In the present specification, the alkenyl group includes not only those having only one double bond but also those having two or more double bonds, for example, alkadienyl group, alkatrienyl group and the like. To do.

In Formula (1), R ¹ and R ⁴ are preferably the same, R ² and R ³ are preferably the same, A ¹ and A ² are preferably the same, and n and m is preferably the same, and p and q are preferably the same.

In formula (3), R ¹ and R ⁴ are preferably the same, R ² and R ³ are preferably the same, A ¹ and A ² are preferably the same, and n and m is preferably the same, and p and q are preferably the same.

In the formula (4), R ¹ and R ⁴ are preferably the same, R ² and R ³ are preferably the same, and t and u are preferably the same.

In the formula (5), R ¹ and R ⁴ are preferably the same, R ² and R ³ are preferably the same, and t and u are preferably the same.

In Formula (6), it is preferable that t and u are the same.

As the compound represented by the formula (1),
l is an integer of 2 to 4, n and m are each independently an integer of 2 to 6, p and q are each independently 0 or 1, and A ¹ and A ² are Each independently is —CO— or —CH ₂ —, R ² and R ³ are each a hydrogen atom, and R ¹ and R ⁴ are each independently a hydrogen atom or an alkyl group having 3 to 20 carbon atoms. A compound represented by formula (1),
l is an integer of 2 to 4, n and m are each independently an integer of 2 to 6, p and q are each independently 0 or 1, and A ¹ and A ² are Each independently is —CO— or —CH ₂ —, R ² and R ³ are each a hydrogen atom, and R ¹ and R ⁴ are each independently a hydrogen atom, a phenyl group or a carbon number of 7 to 18 A compound represented by the formula (1) which is an alkylphenyl group;
l is an integer of 2 to 4, n and m are each independently an integer of 2 to 6, p and q are each independently 0 or 1, and A ¹ and A ² are Each independently —CO—, or one CH ₂ —, R ² and R ³ are each a hydrogen atom, and R ¹ and R ⁴ are each independently a hydrogen atom or a straight chain having 6 to 18 carbon atoms. A compound represented by the formula (1) which is an alkyl group;
l is an integer of 2 to 4, n and m are the same and are integers of 2 to 6, p and q are 1, and A ¹ and A ² are the same -CO-, R ² and R ³ are hydrogen atoms, R ¹ and R ⁴ are the same and are an alkyl group having 3 to 20 carbon atoms. Compound,
l is an integer of 2 to 4, n and m are the same, and are integers of 2 to 6, p and q are 1, and A ¹ and A ² are the same -CO-, R ² and R ³ are hydrogen atoms, R ¹ and R ⁴ are the same, and are a linear alkyl group having 6 to 18 carbon atoms (1) A compound represented by
l is an integer of 2 to 4, n and m are the same and an integer of 2 to 6, p and q are 0, and R ² and R ³ are hydroponic atoms A compound represented by formula (1) wherein R ¹ and R ⁴ are a hydrogen atom or the same, and an alkyl group having 3 to 20 carbon atoms, and l is an integer of 2 to 4 N and m are the same and are integers of 2 to 6, p and q are 0, R ² and R ³ are hydrogen atoms, and R ¹ and R ⁴ are water A compound represented by the formula (1) which is a cord atom or is the same and is a linear alkyl group having 6 to 18 carbon atoms is preferred.

As the compound represented by the formula (3),
n and m are each independently an integer of 2 to 6, p and q are each independently 0 or 1, and A ¹ and A ² are each independently —CO— or —CH ₂ Embedded image represented by the formula (3), wherein R ² and R ³ are hydrogen atoms, and R ¹ and R ⁴ are each independently a hydrogen atom or an alkyl group having 3 to 20 carbon atoms,
n and m are each independently an integer of 2 to 6, p and q are each independently 0 or 1, and A ¹ and A ² are each independently —CO— or —CH ₂ In formula (3), R ² and R ³ are hydrogen atoms, and R ¹ and R ⁴ are each independently a hydrogen atom, a phenyl group, or an alkylphenyl group having 7 to 18 carbon atoms. Chemical inclusions,
n and m are each independently an integer of 2 to 6, p and q are each independently 0 or 1, and A ¹ and A ² are each independently —CO— or —CH _2- R, R ¹ and R ³ are each a hydrogen atom, and R ¹ and R ⁴ are each independently a hydrogen atom or a linear alkyl group having 6 to 18 carbon atoms. Compound,
n and m are the same and are an integer of 2 to 6, p and q are 1, A ¹ and A ² are the same and are —CO—, R ² and A compound represented by formula (3), wherein R ³ is a hydrogen atom, R ¹ and R ⁴ are the same and are an alkyl group having 3 to 20 carbon atoms,
n and m are the same and are an integer of 2 to 6, p and q are 1, A ¹ and A ² are the same and are —CO—, R ² and A compound represented by the formula (3), wherein R ³ is a hydrogen atom, R ¹ and R ⁴ are the same, and is a linear alkyl group having 6 to 18 carbon atoms;
n and m are the same and are an integer of 2 to 6, p and q are 0, R ² and R ³ are aquatic atoms, and R ¹ and R ⁴ are aquatic atoms Or the same and the compound represented by the formula (3), which is an alkyl group having 3 to 20 carbon cords, and n and m are the same and are an integer of 2 to 6 P and q are 0, R ² and R ³ are hydrogen atoms, R ¹ and R ⁴ are hydrogen atoms, or the same, and having 6 to 18 carbon cords A compound represented by the formula (3) which is a linear alkyl group is preferred.

As the compound represented by the formula (4),
a compound in which t and u are each independently an integer of 2 to 6, R ² and R ³ are hydrogen atoms, and R ¹ and R ⁴ are each independently an alkyl group having 3 to 20 carbon atoms A compound represented by (4),
t and u are each independently an integer of 2 to 6, R ² and R ³ are hydrogen atoms, and R ¹ and R ⁴ are each independently a linear alkyl group having 6 to 18 carbon atoms. A compound represented by the formula (4):
t and u are the same and are an integer of 2 to 6, R ² and R ³ are a hydrogen atom, R ¹ and R ⁴ are the same and have 3 to 20 carbon atoms The compound represented by the formula (4) which is an alkyl group, and t and u are the same, each of which is an integer of 2 to 6, R ² and R ³ are hydrogen atoms, R ¹ and R A compound represented by the formula (4) in which ⁴ is the same and is a linear alkyl group having 6 to 18 carbon atoms is preferred.

As the compound represented by the formula (5),
t and u are each independently an integer of 2 to 6, R ² and R ³ are a hydrogen atom, and R ¹ and R ⁴ are each independently a hydrogen atom or an alkyl group having 3 to 20 carbon atoms. A compound represented by the formula (5):
t and u are each independently an integer of 2 to 6, R ² and R ³ are a hydrogen atom, and R ¹ and R ⁴ are each independently a hydrogen atom or a straight chain having 6 to 18 carbon atoms A compound represented by formula (5), which is an alkyl group;
t and u are the same and are an integer of 2 to 6, R ² and R ³ are hydrogen atoms, R ¹ and R ⁴ are hydrogen atoms, or are the same, and , A compound represented by the formula (5) which is an alkyl group having 3 to 20 carbon atoms, and t and u are the same and are an integer of 2 to 6, and R ² and R ³ are hydrogen atoms And a compound represented by the formula (5) wherein R ¹ and R ⁴ are a hydrogen atom or the same and is a linear alkyl group having 6 to 18 carbon atoms is preferred.

The additive for asphalt of the present invention contains a salt of the above compound, for example, a salt of an organic acid such as carboxylic acid or sulfonic acid of the above compound, or a salt of a mineral acid such as hydrochloric acid, hydrobromic acid, sulfuric acid or phosphoric acid. It's okay. In the present invention, as the carboxylate of the above compound, hexanoate, heptanoate, octanoate, nonanoate, decanoate, undecanoate, laurate, tridecanoate, myristate, pentadecane Acid salt, palmitate, heptadecanoate, stearate, α-linolenate, linoleate, oleate, ricinoleate, citrate, succinate, tartrate, malate, myristolein Acid salt, palmitate, sabiate, elaidate, vacsenate, gadoleate, eicosenate, erucate, nervonate, eicosadienoate, docosadienoate, pinolenate, eleostearin Acid salt, mede acid salt, eicosatrienoate, stearidonate, arachidonic acid salt, eicosatetraenoate, adren Salt, boseopentaenoate, eicosapentaenoate, ozbondate, sardine, tetracosapentaenoate, docosahexaenoate, nicinate, abietic acid, dehydroabietic acid, neoabietic acid, pimaric acid Examples thereof include saturated or unsaturated carboxylates having 2 to 30 carbon atoms such as salts, isopimarates, and parastrinates. Among these, a saturated or unsaturated carboxylate having 8 to 24 carbon atoms is preferable, a saturated or unsaturated carboxylate having 10 to 20 carbon atoms is more preferable, and decanoate, laurate, myristate, pentadecane. Further preferred are acid salts, palmitates, heptadecanoates, stearates, oleates, linoleates, linolenates and ricinoleates.

The compound represented by the formula (1) is, for example, “Journal of Organic Chemistry” by Jaesung Choi et al., 1995, Vol. 60, p. It can be produced by a known method such as the method described in 3266-3267.

The asphalt additive of the present invention can contain at least one oil selected from the group consisting of petroleum-based blended oils and lubricating oils. Petroleum-based blended oils include aromatics having an aromatic carbon number of 35% by weight or more of the total number of carbons, naphthenes having a naphthenic ring carbon number of 30 to 45% by weight of the total number of carbons, and paraffin side chain carbons. Examples thereof include paraffinic compounds whose number is 50% by weight or more of the total number of carbons. In this invention, 1 type, or 2 or more types of these can be used suitably. Examples of the lubricating oil include petroleum-based lubricating oil, synthetic lubricating oil, fatty oil, and the like, and one or more of them can be used as appropriate. Petroleum-based lubricating oil is a heavy oil with a boiling point of about 30 ° C or higher obtained as a distillation residue of crude oil at atmospheric pressure, and is divided into various spilled oils by vacuum distillation. For example, dewaxing, sulfuric acid treatment, solvent extraction The final product is finished by appropriate refining treatment such as deasphalting and clay treatment. Synthetic lubricating oils are lubricating oils that are manufactured by organic synthesis and are generally classified according to their application. For example, spindle oil, compressor oil, dynamo oil, turbine oil, machine oil, engine oil, jet engine oil, operation Examples include oil. The fatty oil is mainly mixed with petroleum-based lubricating oil and used as a hybrid oil in applications that require oiliness or emulsification. In the present invention, it is preferable to use a synthetic lubricating oil. When using a petroleum-based blended oil and a lubricating oil in combination, the total amount may be a predetermined amount.

When the asphalt additive of the present invention contains oil, the content of the compound represented by formula (1) or a salt thereof is usually 0.01 to 200 parts by weight, preferably 100 parts by weight of oil. The amount is 0.1 to 150 parts by weight, more preferably 1 to 100 parts by weight.

The asphalt additive of the present invention can contain a surfactant in addition to the oil. As the surfactant, any of an ionic surfactant and a nonionic surfactant can be used.

Examples of ionic surfactants include: anionic surfactants such as polyoxyethylene alkyl ether phosphates (salts), polyoxyethylene alkyl sulfosuccinates, alkyl sulfates, fatty acid salts, etc .; cationic interfaces Activators such as quaternary ammonium salts and fatty acid amidoamines; amphoteric surfactants such as alkylbetaines and alkylamine oxides.

Nonionic surfactants include the following: ester surfactants having an ester structure, such as sorbitan fatty acid esters, etc .; ether surfactants having an ether structure, such as polyoxyalkylene alkyl ether, poly Examples thereof include oxyethylene derivatives and polyoxyethylene polyoxypropylene glycol.

The asphalt additive of the present invention can contain two or more surfactants. When the asphalt additive of the present invention contains a surfactant, the content of the surfactant is usually 0.01 to 100 parts by weight with respect to 100 parts by weight of the compound represented by the formula (1) or a salt thereof. Parts by weight, preferably 0.05 to 80 parts by weight, more preferably 0.1 to 50 parts by weight.

The present invention also provides an asphalt composition containing the above asphalt additive. The asphalt used in the present invention is not particularly limited, and natural asphalt such as lake asphalt, cutback asphalt, petroleum tar, pitch, straight asphalt, blown asphalt, semi-blown asphalt, solvent deasphalted asphalt (for example, propane desulfurized). Petroleum asphalt such as asphalt). Examples of natural asphalt include gilsonite, grahamalite, and trinidad lake asphalt. These asphalts may be used alone or in combination of two or more. Moreover, what blended artificial asphalt with the said asphalt in arbitrary ratios can also be used as raw material asphalt. As an example of the artificial asphalt that can be used in the present invention, petroleum-based blended oil and tackifier resin in a percentage by weight of petroleum-based blended oil: tackifier resin = (0 to 100% by weight): ( 100% to 0% by weight).

In the asphalt composition of the present invention, asphalt, modified asphalt, for example, modified asphalt type I, modified asphalt type II, modified asphalt H type, high viscosity modified asphalt, and a higher viscosity than the high viscosity modified asphalt. Asphalt called regenerated asphalt, such as high modified asphalt, can be used.

As the modified asphalt, straight asphalt modified with rubber and / or thermoplastic elastomer can be used. Examples of the rubber include natural rubber and chloroprene rubber. Examples of the thermoplastic elastomer include styrene-butadiene block copolymer, styrene-isoprene block copolymer, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, acrylic ester, methacrylic ester, styrene alone Examples thereof include a polymer and a copolymer obtained by combining these, and a styrene-butadiene block copolymer and a styrene-isoprene block copolymer are particularly preferable. The total amount of rubber and thermoplastic elastomer is preferably 0.1 to 25 parts by weight, more preferably 1 to 20 parts by weight, and still more preferably 3 to 15 parts by weight with respect to 100 parts by weight of asphalt.

Recycled asphalt is not particularly limited, and examples include asphalt including asphalt pavement waste material used for road construction. In the present invention, various types of asphalt pavement waste can be mentioned, but asphalt pavement waste generated during various constructions, for example, asphalt pavement waste generated during subway construction, underground piping work, road paving work, etc. Can be mentioned. According to the present invention, in any of these asphalts, it is possible to lower the viscosity of the asphalt during heating and mixing and construction, and the effect of improving the aggregate grasping power is exhibited.

In the asphalt composition of the present invention, a petroleum-based blended oil called process oil can be blended as long as the effects of the present invention are not hindered. Petroleum-based blended oils include aromatics having an aromatic carbon number of 35% by weight or more of the total number of carbons, naphthenes having a naphthenic ring carbon number of 30 to 45% by weight of the total number of carbons, and paraffin side chain carbons. Examples thereof include paraffinic compounds whose number is 50% by weight or more of the total number of carbons. In this invention, 1 type, or 2 or more types of these can be used suitably. Further, a lubricating oil may be used instead of the petroleum-based blended oil, or both may be used in combination. When both are used together, the total amount may be a predetermined amount. Examples of the lubricating oil include petroleum-based lubricating oil, synthetic lubricating oil, fatty oil, and the like, and one or more of them can be used as appropriate. Petroleum-based lubricating oil is a heavy oil with a boiling point of about 30 ° C or higher obtained as a distillation residue of crude oil at atmospheric pressure, and is divided into various spilled oils by vacuum distillation. For example, dewaxing, sulfuric acid treatment, solvent extraction The final product is finished by appropriate refining treatment such as deasphalting and clay treatment. Synthetic lubricating oils are lubricating oils that are manufactured by organic synthesis and are generally classified according to their application. For example, spindle oil, compressor oil, dynamo oil, turbine oil, machine oil, engine oil, jet engine oil, operation Examples include oil. The fatty oil is mainly mixed with petroleum-based lubricating oil and used as a hybrid oil in applications that require oiliness or emulsification. In the present invention, it is preferable to use a synthetic lubricating oil.

In the asphalt additive and the asphalt composition of the present invention, various additives can be further blended as long as the effects of the present invention are not hindered. The additive is not particularly limited, and fillers such as stone powder, talc and calcium carbonate, fiber reinforcing agents such as cement, activated carbon, slaked lime, methylcellulose, and polyvinyl alcohol, 2,6-di-t-butyl-4- Examples thereof include antioxidants such as methylphenol, ultraviolet absorbers, and light stabilizers.

In the asphalt additive and the asphalt composition of the present invention, tackifier resins can be blended as long as the effects of the present invention are not hindered. As the tackifier resins, both natural resins and synthetic resins can be used. A terpene resin can be used as the natural resin. Further, as the synthetic resin, a polymer resin such as petroleum resin, coumarone / indene resin, styrene resin can be used. Petroleum resins include aliphatic (C5) petroleum resins mainly composed of a fraction having a boiling point of 20 to 60 ° C. (C5 fraction) separated by distillation of the naphtha decomposition product, and also naphtha decomposition products. Aromatic (C9) petroleum resins mainly composed of a fraction having a boiling point of 160 to 260 ° C. (C9 fraction) separated by distillation, an aliphatic / copolymerized copolymer of these C5 and C9 petroleum resins Aromatic copolymer (C5 / C9) petroleum resins and alicyclic (DCPD) petroleum resin terpenes mainly composed of high-purity dicyclopentadiene separated by distillation of naphtha decomposition products; Examples thereof include terpene phenol resins obtained by copolymerizing phenols. In addition to these, various petroleum-based, coal-based, and polymer-based waxes such as natural wax, synthetic wax, and compounded wax can be used in the same manner. These include paraffin wax, microcrystalline wax, slack wax, Fischer Tropus wax, caster wax, hydrogenated wax, montan wax, polyethylene wax, polypropylene wax, etc., and in the present invention, one or more of these Can be mixed and used.

The asphalt additive and asphalt composition of the present invention may further contain sulfur or an organic peroxide as long as the effects of the present invention are not hindered. Examples of sulfur include fine powder sulfur, colloidal sulfur, precipitated sulfur, and dispersible sulfur, but are not limited thereto. Examples of the organic peroxide include dicumyl peroxide, 2,5 dimethyl 2,5 di (t-butylperoxy) hexane, 1,3 di (2-t-butylperoxyisopropyl) benzene, di-t- Examples include butyl peroxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) -3-hexyne, and the like.

Further, the asphalt additive of the present invention and the asphalt composition containing the same may contain water in an amount that does not impair the effects of the present invention.

In the asphalt composition of the present invention, the compound represented by the formula (1) or a salt thereof is preferably 0.005 to 20 parts by weight, more preferably 0.01 to 15 parts by weight with respect to 100 parts by weight of asphalt. Part, more preferably 0.1 to 10 parts by weight.

The asphalt composition of the present invention is a premix method in which the asphalt additive of the present invention is added to and mixed with the asphalt prior to the addition of the aggregate, and when the asphalt and the aggregate are mixed in the asphalt mixing station. It can be applied to any plant mix method in which an additive is added. In the case of the premix method, there is an advantage that it is possible to save the labor of inputting materials in the asphalt mixing station. In the premix method, each component can be mixed using a homomixer, a dissolver, a paddle mixer, a ribbon mixer, a screw mixer, a planetary mixer, a vacuum backflow mixer, or the like. In the case of the plant mix method, each component can be stirred and mixed using a pug mill mixer, a spiral flow mixer, a screw mixer or the like.

Further, the method for adding the asphalt additive of the present invention to the asphalt is not particularly limited, and the asphalt melted by heating to 100 to 300 ° C, preferably 120 to 280 ° C, more preferably 150 to 250 ° C, or What is necessary is just to add predetermined amount to the mixture of asphalt and an aggregate, stirring. In addition, the additive of the present invention has good solubility and affinity in asphalt, and it is not necessary to stir because it is mixed even by thermal convection or vibration during transportation, but when immediate effect is required Therefore, it is preferable to stir and mix. Further, when rubber and / or thermoplastic elastomer is added to asphalt, the asphalt additive of the present invention and rubber and / or thermoplastic elastomer may be added to heated asphalt simultaneously or separately. . When added separately, the order of addition is not particularly limited.

The asphalt composition containing the asphalt additive of the present invention is reduced in viscosity by setting measurement conditions according to the composition, heating and mixing temperature, construction temperature, etc. using, for example, a Brookfield B-type viscometer. You can be sure that In the case of the modified asphalt H type, the viscosity can be measured at a temperature of 150 ° C., for example. In the case of recycled asphalt, the viscosity can be measured at a temperature of 170 ° C., for example.

The asphalt composition containing the asphalt additive of the present invention can be used for road pavement materials, roofing materials, waterproof materials and the like. The asphalt composition of the present invention is preferably used in an asphalt mixture because of its excellent aggregate grasping power. Pavement using an asphalt mixture for road pavement, particularly drainage pavement and permeable pavement with high porosity, Suitable for road pavement.

The asphalt mixture of the present invention can be produced by mixing the asphalt composition of the present invention and an aggregate such as crushed stone. The aggregate is not particularly limited as long as it conforms to the asphalt pavement outline, pavement design and construction guidelines, and the pavement construction manual (all published by the Japan Road Association), but crushed stone, gravel, sand , Slag, filler and the like. In addition to these, various low-grade aggregates and recycled aggregates can be used regardless of the material. Aggregates can be used alone or as a mixture of two or more. When used as a mixture of two or more, the type and blending ratio of each aggregate can be appropriately selected according to the required strength of the pavement, the site of the pavement, the water permeability, and the like. The asphalt mixture of the present invention is preferably composed of an asphalt composition and an aggregate made of crushed stone, sand and filler. In the present invention, the blending ratio of the asphalt composition and the aggregate is preferably 1 to 15% by weight of the asphalt composition and 99 to 85% by weight of the aggregate based on the total weight of the asphalt mixture, and 1 to 10% by weight. More preferred is an asphalt composition of 99-90% by weight aggregate.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.

Degraded asphalt Using new straight asphalt 60-80 (manufactured by JX Nippon Mining & Energy Corporation), in accordance with JISK 2207 thin film thermal degradation test, after conducting thermal degradation over 5 hours at 163 ° C, pavement survey and test method Degraded asphalt was prepared for 21 hours under 105 ° C. and air pressure of 2.10 MPa according to the pressure degradation test described in the Handbook (edited by the Japan Road Association). Degraded asphalt created by this method is said to almost reproduce the degradation state after about 5 years of outdoor use of asphalt, and it is effective in creating degraded materials. did.

Viscosity measurement (Example 1)
Using a Brookfield type B viscometer, an asphalt composition obtained by adding 5 parts by weight of bis (3-aminopropyl) disulfide to 100 parts by weight of deteriorated asphalt was stirred at 160 ° C. for 3 minutes, and then the viscosity was measured. Subsequently, the viscosity at 110 ° C. was measured. The results are shown in Table 1. The unit of viscosity in the table is centipoise (cP).

(Examples 2 to 3)
An asphalt composition was obtained in the same manner as in Example 1 except that bis (3-aminopropyl) disulfide was changed to the compounds shown in Table 1, and the viscosity was measured.

(Comparative Example 1)
An asphalt composition was obtained in the same manner as in Example 1 except that bis (3-aminopropyl) disulfide was not used, and the viscosity was measured.

(Comparative Example 2)
Bis (3-aminopropyl) disulfide changed to Showa Shell Sekiyu KK mineral oil (kinematic viscosity at 40 ° C. (JIS K 2283) = 257 mm ² / s, pour point (JIS K 2269) = − 22.5 ° C.) Except for this, an asphalt composition was obtained in the same manner as in Example 1, and the viscosity was measured.

(Examples 4 to 10)
Example 1 except that the deteriorated asphalt was changed to modified asphalt H type, bis (3-aminopropyl) disulfide was changed to the compounds shown in Table 2, and the viscosity measurement temperatures were changed to 170 ° C. and 150 ° C. In the same manner as above, an asphalt composition was obtained, and the viscosity was measured.

(Comparative Example 3)
An asphalt composition was obtained in the same manner as in Example 4 except that bis (3-aminopropyl) disulfide was not used, and the viscosity was measured.

(Comparative Example 4)
Bis (3-aminopropyl) disulfide changed to Showa Shell Sekiyu KK mineral oil (kinematic viscosity at 40 ° C. (JIS K 2283) = 257 mm ² / s, pour point (JIS K 2269) = − 22.5 ° C.) An asphalt composition was obtained in the same manner as in Example 4 except that the viscosity was measured.

(Comparative Example 5)
An asphalt composition was obtained in the same manner as in Example 4 except that bis (3-aminopropyl) disulfide was changed to stearic acid, and the viscosity was measured.

(Example 11)
After mixing 100 parts by weight of aggregate (a mixture in which the weight ratio of crushed stone: sand: filler is about 80: about 15: about 5) and 5 parts by weight of the asphalt composition prepared in Example 4 at 170 ° C. A drainage asphalt mixture (aggregate maximum particle size 13 mm) having a porosity of 20% was obtained by tamping. The properties of the obtained asphalt mixture are shown in Table 3. The stability of the asphalt mixture was evaluated by a Marshall stability test. The higher the numerical value, the better the Marshall stability. The aggregate grasping power of the asphalt mixture was evaluated by a cantabro test. In the cantabro test, the lower the value, the lower the loss rate due to aggregate scattering.

(Comparative Examples 6 to 8)
A drainage asphalt mixture was obtained in the same manner as in Example 11 except that the asphalt composition prepared in Comparative Examples 3 to 5 was used instead of the asphalt composition prepared in Example 4, and the viscosity was measured. Carried out. The results are shown in Table 3.

Example 12
A drainage asphalt mixture was obtained in the same manner as in Example 11 except that the asphalt composition prepared in Example 4 was changed to the asphalt composition prepared in Example 5 and the mixed temperature was changed to 150 ° C. The stability of the drainage asphalt mixture and the evaluation of aggregate grasping power were evaluated.

(Comparative Examples 9 to 10)
A drainage asphalt mixture was obtained in the same manner as in Example 12 except that the asphalt composition prepared in Comparative Examples 3 to 4 was used instead of the asphalt composition prepared in Example 5, and a drainage asphalt was obtained. The stability of the mixture and the evaluation of the aggregate grasping power were evaluated.

(Example 13)
Showa Shell Sekiyu KK mineral oil (kinematic viscosity at 40 ° C. (JIS K 2283) = 257 mm ² / s, pour point (JIS K 2269) = − 22.5 ° C.) per 100 parts by weight 25 parts by weight of aminopropyl) disulfide and 7.5 parts by weight of sorbitan fatty acid ester were sufficiently mixed at room temperature to obtain additive A.
An asphalt composition was obtained in the same manner as in Example 1 except that 5 parts by weight of the obtained additive A was used instead of 5 parts by weight of bis (3-aminopropyl) disulfide. Viscosity measurement was implemented about the obtained asphalt composition. The results are shown in Table 1.

(Example 14)
A drainage asphalt mixture was obtained in the same manner as in Example 11 except that the asphalt composition prepared in Example 13 was used instead of the asphalt composition prepared in Example 4. Viscosity measurement was carried out on the obtained drainable asphalt mixture. The results are shown in Table 3.

In Examples and Comparative Examples, the physical properties of asphalt compositions and asphalt mixtures were measured or defined as follows.

<Measurement of asphalt composition>
(viscosity)
Using a Brookfield B-type viscometer, measurements were made at the temperatures listed in each table.

<Measurement of asphalt mixture>
(Marshall stability test and cantable test)
The test was conducted in accordance with the test method described in the Pavement Test Method Handbook (issued by the Japan Road Association). The tamping was performed on the asphalt mixture prepared in each Example and Comparative Example at a temperature 15 ° C. lower than the mixing temperature so that the porosity was 20%. The degree of compaction was expressed in% as the porosity which is the ratio of the density before tamping to the density of the asphalt mixture after tamping.

As is clear from Table 1 or Table 2, mixing the asphalt additive of the present invention (Examples 1 to 10 and Example 13) resulted in an asphalt mixture rather than Comparative Examples 1 and 3 where no additive was added. The viscosity of can be greatly reduced. Further, as is apparent from Comparative Examples 2, 4 and 5, the asphalt additive of the present invention was far superior in reducing the viscosity of the asphalt mixture than oil and wax.

Further, as is clear from Table 3 or Table 4, the asphalt mixture containing the asphalt additive of the present invention is excellent in both the Marshall stability indicating the stability of the asphalt mixture and the loss rate indicating the aggregate grasping power. It was.

Claims

An additive for asphalt containing a compound represented by the formula (1) or a salt thereof.

[Where,
n and m are each independently an integer of 1 to 20,
l is an integer from 1 to 4,
p and q are each independently 0 or 1,
A 1 and A 2 each independently represent —CO—, —CH 2 —, —O—, —CO 2 —, or —OCO—,
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group, and R 2 and R 3 are bonded to form a cyclic structure. It may be. ]
The additive for asphalt according to claim 1, wherein the compound represented by the formula (1) or a salt thereof is the compound represented by the formula (3) or a salt thereof.

[Where,
n and m are each independently an integer of 1 to 20,
p and q are each independently 0 or 1,
A 1 and A 2 each independently represent —CO—, —CH 2 —, —O—, —CO 2 —, or —OCO—,
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group, and R 2 and R 3 are bonded to form a cyclic structure. It may be. ]
The compound represented by the formula (1) or a salt thereof is the compound represented by the formula (4) or a salt thereof, or the compound represented by the formula (5) or a salt thereof. Additive for asphalt.

[Where,
t and u are each independently an integer of 2 to 6;
p and q are each independently 0 or 1,
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group, and R 2 and R 3 are bonded to form a cyclic structure. It may be. ]
The additive for asphalt according to claim 1, wherein the compound represented by the formula (1) or a salt thereof is the compound represented by the formula (6) or a salt thereof.

[Where,
t and u are each independently an integer of 2 to 6. ]
The asphalt additive according to any one of claims 1 to 4, wherein the salt is a carboxylate.
The asphalt additive according to any one of claims 1 to 5, further comprising at least one oil selected from the group consisting of petroleum-based blended oils and lubricating oils.
The additive for asphalt according to claim 6, wherein the content of the compound represented by the formula (1) or a salt thereof is 0.01 to 200 parts by weight with respect to 100 parts by weight of the oil.
The additive for asphalt according to claim 6 or 7, further comprising a surfactant.
The asphalt additive according to claim 8, wherein the content of the surfactant is 0.01 to 100 parts by weight with respect to 100 parts by weight of the compound represented by the formula (1) or a salt thereof.
An asphalt composition comprising the asphalt additive according to any one of claims 1 to 9 and asphalt.
The asphalt composition according to claim 10, comprising 0.005 to 20 parts by weight of the compound represented by the formula (1) or a salt thereof with respect to 100 parts by weight of asphalt.
An asphalt mixture for road pavement containing the asphalt composition according to claim 10 or 11 and an aggregate.
The asphalt mixture according to claim 12, for production and construction at a temperature of 100 to 300 ° C.
A pavement comprising the asphalt mixture for road pavement according to claim 12 or 13.