TW201634552A - Asphalt additive - Google Patents

Asphalt additive Download PDF

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TW201634552A
TW201634552A TW105102940A TW105102940A TW201634552A TW 201634552 A TW201634552 A TW 201634552A TW 105102940 A TW105102940 A TW 105102940A TW 105102940 A TW105102940 A TW 105102940A TW 201634552 A TW201634552 A TW 201634552A
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asphalt
compound represented
additive
formula
salt
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TW105102940A
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Chinese (zh)
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Tamon Itahashi
Yuta Kikuchi
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Sumitomo Chemical Co
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/36Sulfur-, selenium-, or tellurium-containing compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L95/00Compositions of bituminous materials, e.g. asphalt, tar, pitch
    • EFIXED CONSTRUCTIONS
    • E01CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
    • E01CCONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
    • E01C7/00Coherent pavings made in situ
    • E01C7/08Coherent pavings made in situ made of road-metal and binders
    • E01C7/18Coherent pavings made in situ made of road-metal and binders of road-metal and bituminous binders
    • EFIXED CONSTRUCTIONS
    • E01CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
    • E01CCONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
    • E01C7/00Coherent pavings made in situ
    • E01C7/08Coherent pavings made in situ made of road-metal and binders
    • E01C7/30Coherent pavings made in situ made of road-metal and binders of road-metal and other binders, e.g. synthetic material, i.e. resin
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated

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  • Chemical & Material Sciences (AREA)
  • Structural Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Civil Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Architecture (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Road Paving Structures (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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

瀝青用添加劑 Asphalt additive

本專利申請案係對日本專利申請第2015-016954號(申請日2015年1月30日)而主張優先權者,藉由在本文中對其進行參照,而將其全部內容併入本說明書中。 The present patent application claims priority to Japanese Patent Application No. 2015-016954 (filed Jan. 30, 2015), the entire disclosure of which is incorporated herein by reference. .

本發明係關於一種瀝青舖面之道路施工所使用之瀝青用之添加劑。此處,瀝青係關於瀝青舖面所使用之瀝青。 The present invention relates to an additive for asphalt used in road construction for asphalt pavement. Here, the asphalt is a bitumen used for asphalt paving.

於實施瀝青舖面之道路施工之情形時,瀝青係於在瀝青混合場所與骨材進行加熱混合而製成瀝青混合物後,向施工場所搬運而使用。一般而言,瀝青因溫度導致其黏度發生變化,溫度越高黏度越低,具有溫度越低黏度越高而流動性下降之性質。由於瀝青在瀝青混合場所進行加熱混合時或對道路實施施工時需要黏度足夠低,故而需要根據瀝青之種類適當設定混合時或施工時之溫度。 In the case of road construction where asphalt pavement is carried out, the asphalt is heated and mixed with the aggregate in an asphalt mixing place to form an asphalt mixture, and then transported to a construction site for use. In general, the viscosity of the asphalt changes due to temperature, and the higher the temperature, the lower the viscosity, and the lower the temperature, the higher the viscosity and the lower the fluidity. Since the viscosity of the asphalt is required to be sufficiently low when it is heated and mixed in the asphalt mixing place or when the road is applied, it is necessary to appropriately set the temperature at the time of mixing or construction depending on the type of the asphalt.

於直餾瀝青與骨材進行混合之情形時,瀝青混合場所中之加熱混合為於160℃左右進行,於施工場所之施工溫度為110℃~150℃。因此,瀝青混合物係於160℃左右之溫度下自瀝青混合場所出貨,但因搬運至施工場所之期間冷卻,導致黏度下降。又,已知瀝青容易因加熱而引起劣化,劣化之瀝青於施工後之性能、尤其是穩定性或骨材握持力等下降,黏度上升,因此為了不引起此種劣化,較佳為儘量於低溫下進行加熱混合、或施工。 When the straight-run asphalt and the aggregate are mixed, the heating and mixing in the asphalt mixing place is performed at about 160 ° C, and the construction temperature in the construction site is 110 ° C to 150 ° C. Therefore, the asphalt mixture is shipped from the asphalt mixing place at a temperature of about 160 ° C, but the viscosity is lowered due to cooling during transportation to the construction site. Further, it is known that the asphalt is liable to be deteriorated by heating, and the performance of the deteriorated asphalt after the construction, particularly the stability or the grip strength of the aggregate, is lowered, and the viscosity is increased. Therefore, in order not to cause such deterioration, it is preferred to Heat mixing or construction at low temperatures.

於高負荷交通路線中,作為針對提高交通負荷之瀝青舖面道路 之穩定性的對策,業界一直使用利用SBS(苯乙烯、丁二烯、苯乙烯嵌段共聚物)等聚合物對直餾瀝青進行改質之瀝青(改質瀝青H型等)。改質瀝青必須黏度高於直餾瀝青,且在高於直餾瀝青之情況之溫度下與骨材進行加熱混合。於使用改質瀝青H型之情形時,通常,加熱混合溫度為170℃~180℃左右,施工溫度為140℃~170℃。 As a pavement road for increasing traffic load in high-load traffic routes In the industry, a pitch (modified pitch H type, etc.) which is modified with a polymer such as SBS (styrene, butadiene or styrene block copolymer) to reform straight asphalt is used. The modified bitumen must have a higher viscosity than the straight-run bitumen and be heated and mixed with the aggregate at a temperature higher than that of the straight-run bitumen. When using the modified asphalt H type, the heating and mixing temperature is usually about 170 ° C ~ 180 ° C, and the construction temperature is 140 ° C ~ 170 ° C.

又,近年來,以減少道路噪音或提高排水性能為目的,又,為了進一步提高瀝青舖面之耐久性,亦開發出較改質瀝青H型進一步增加SBS添加量而進行高度改質之瀝青。然而,由於此種瀝青必須於更高溫度下進行加熱混合,故而容易引起劣化。因此,為了避免此種劣化,要求不提高加熱混合或施工溫度而降低瀝青之黏度。 In addition, in order to further improve the durability of the asphalt pavement, in order to further improve the durability of the asphalt pavement, in recent years, an asphalt which is more highly modified than the modified asphalt H-type to further increase the amount of SBS is developed. However, since such an asphalt must be heated and mixed at a higher temperature, it is liable to cause deterioration. Therefore, in order to avoid such deterioration, it is required to lower the viscosity of the asphalt without increasing the heating mixing or the application temperature.

瀝青舖面所使用之瀝青混合物因隨著年數增加發生劣化而被修繕,此時再生使用自道路剝下之瀝青混合物。但是,瀝青混合物之反覆之再生使用會使瀝青混合物中之瀝青劣化相當地進行,故而與新瀝青相比黏度變得非常高。又,瀝青混合物之再生使用係主要對直餾瀝青進行,但因使用改質瀝青之舖面物之修繕,會於直餾瀝青之再生品中混入改質瀝青之再生品,其結果為,再生使用之瀝青之黏度變得更高。因此,要求降低進行瀝青之加熱混合及施工作業時之瀝青之黏度。 The bituminous mixture used in the asphalt pavement is repaired as it deteriorates with the increase in the number of years, at which time the asphalt mixture peeled off from the road is recycled. However, the repeated use of the asphalt mixture for regeneration causes the asphalt in the asphalt mixture to deteriorate considerably, so that the viscosity becomes very high as compared with the new asphalt. In addition, the recycling of the asphalt mixture is mainly carried out on the straight-run asphalt, but the repair of the paving material using the modified asphalt will be mixed with the recycled asphalt in the recycled product of the straight-run asphalt, and as a result, the recycled product is used. The viscosity of the asphalt becomes higher. Therefore, it is required to reduce the viscosity of the asphalt during the heating and mixing of the asphalt and the construction work.

先前,作為降低瀝青黏度之技術,已知有向瀝青中添加礦物油等油成分,使高溫下之瀝青之黏度下降的方法。然而,於添加油成分之方法中,存在因添加油成分後之瀝青變軟,故而冷卻後之瀝青混合物之骨材握持力下降,施工後之道路之穩定性變得不充分之情況。 Conventionally, as a technique for lowering the viscosity of the asphalt, a method of adding an oil component such as mineral oil to the pitch to lower the viscosity of the asphalt at a high temperature has been known. However, in the method of adding an oil component, since the pitch after the addition of the oil component becomes soft, the grip strength of the asphalt mixture after cooling is lowered, and the stability of the road after the construction is insufficient.

又,作為降低瀝青混合物之材料之混合溫度、舖面施工時之溫度的中等溫度化技術,提出添加特定之有機發泡劑及發泡助劑作為中等溫度化劑之方法(專利文獻1)。然而,添加該中等溫度化劑之方法 雖可降低混合時之溫度,但僅可應用於在瀝青混合場所添加中等溫度化劑之方法(廠拌法)。於預先向瀝青中添加中等溫度化劑之方法(預混法)中,於向瀝青中添加中等溫度化劑之時間點產生發泡,瀝青變得無法儲藏,並且亦無法進行其後之與骨材之混合。因此,瀝青混合物之骨材握持力下降,施工後之道路之穩定性不充分。 In addition, as a medium temperature technique for reducing the mixing temperature of the material of the asphalt mixture and the temperature at the time of paving construction, a method of adding a specific organic foaming agent and a foaming aid as a medium temperature agent has been proposed (Patent Document 1). However, the method of adding the medium temperature agent Although the temperature during mixing can be lowered, it can only be applied to a method of adding a medium temperature agent in an asphalt mixing place (factory mixing method). In the method of adding a medium temperature agent to the asphalt in advance (premixing method), foaming occurs at the time point when the medium temperature agent is added to the pitch, the asphalt becomes unstorable, and the bone cannot be subsequently formed. Mix of materials. Therefore, the grip strength of the asphalt mixture is lowered, and the stability of the road after construction is insufficient.

進而,亦實施添加蠟(脂肪酸)之方法,但藉由該方法所獲得之瀝青舖面體亦於穩定性或動態穩定性方面不充分。 Further, a method of adding a wax (fatty acid) is also carried out, but the asphalt pavement obtained by the method is also insufficient in terms of stability or dynamic stability.

[專利文獻1]日本專利特開2001-131321號公報 [Patent Document 1] Japanese Patent Laid-Open Publication No. 2001-131321

如此,業界先前一直研究使瀝青之黏度降低之技術,但由於該等技術均會損害作業性或添加時之瀝青混合物之各特性,故而期待一種可使瀝青與骨材之混合溫度及瀝青混合物之施工時之溫度下降,並且可同時達成製造瀝青混合物時之作業性及施工後之優異之骨材握持力的瀝青用添加劑。 As such, the industry has previously studied techniques for reducing the viscosity of asphalt, but since these techniques all impair the workability or the characteristics of the asphalt mixture at the time of addition, it is expected that a mixture temperature of the asphalt and the aggregate and the asphalt mixture are expected. The temperature at the time of construction is lowered, and the asphalt additive for the workability in the production of the asphalt mixture and the excellent grip strength of the aggregate after the construction can be achieved at the same time.

本發明提供一種可降低瀝青之黏度,使將瀝青與骨材混合時及對瀝青混合物進行施工時之溫度下降,且獲得施工後之道路之穩定性優異之瀝青舖面體的瀝青用添加劑、瀝青組合物及道路舖面用瀝青混合物。 The invention provides an asphalt additive and asphalt combination for asphalt pavement which can reduce the viscosity of the asphalt, mix the asphalt and the aggregate, and reduce the temperature when the asphalt mixture is applied, and obtain the stability of the road after the construction. Asphalt mixture for objects and road paving.

本發明者等人針對具有瀝青與骨材之加熱混合及瀝青混合物之施工時之瀝青之黏度降低效果及優異之骨材握持力的瀝青用添加劑進行努力研究,結果發現可利用特定式所表示之化合物消除上述問題,從而完成本發明。 The inventors of the present invention have conducted an effort to study an asphalt additive having a viscosity-reducing effect of asphalt and a mixture of asphalt and a bituminous mixture during construction and an excellent grip of the aggregate, and as a result, it has been found that it can be expressed by a specific formula. The compound eliminates the above problems, thereby completing the present invention.

即,本發明包括以下者。 That is, the present invention includes the following.

[1]一種瀝青用添加劑,其含有式(1)所表示之化合物或其鹽。 [1] An additive for asphalt comprising a compound represented by formula (1) or a salt thereof.

[式中,n及m分別獨立為1~20之整數,l為1~4之整數,p及q分別獨立為0或1,A1及A2分別獨立表示-CO-、-CH2-、-O-、-CO2-、或-OCO-,R1、R2、R3及R4分別獨立表示氫原子、或可具有取代基之烴基,R2及R3亦可鍵結而形成環狀結構] [wherein, n and m are each independently an integer from 1 to 20, l is an integer from 1 to 4, and p and q are each independently 0 or 1, and A 1 and A 2 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 a hydrocarbon group which may have a substituent, and R 2 and R 3 may also be bonded. Forming a ring structure]

[2]如上述[1]所記載之瀝青用添加劑,其中上述式(1)所表示之化合物或其鹽為式(3)所表示之化合物或其鹽。 [2] The additive for the asphalt according to the above [1], wherein the compound represented by the above formula (1) or a salt thereof is a compound represented by the formula (3) or a salt thereof.

[式中,n及m分別獨立為1~20之整數,p及q分別獨立為0或1, A1及A2分別獨立表示-CO-、-CH2-、-O-、-CO2-、或-OCO-,R1、R2、R3及R4分別獨立表示氫原子、或可具有取代基之烴基,R2及R3亦可鍵結而形成環狀結構] [wherein, n and m are each independently an integer from 1 to 20, and p and q are each independently 0 or 1, and A 1 and A 2 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 a hydrocarbon group which may have a substituent, and R 2 and R 3 may be bonded to form a cyclic structure]

[3]如上述[1]所記載之瀝青用添加劑,其中上述式(1)所表示之化合物或其鹽為式(4)所表示之化合物或其鹽、或式(5)所表示之化合物或其鹽。 [3] The additive for the asphalt according to the above [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 its salt.

[式中,t及u分別獨立為2~6之整數,R1、R2、R3及R4分別獨立表示氫原子、或可具有取代基之烴基,R2及R3亦可鍵結而形成環狀結構] [wherein, t and u are each independently an integer of 2 to 6, and R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a hydrocarbon group which may have a substituent, and R 2 and R 3 may also be bonded. Forming a ring structure]

[4]如上述[1]所記載之瀝青用添加劑,其中上述式(1)所表示之化合物或其鹽為式(6)所表示之化合物或其鹽。 [4] The additive for the asphalt according to the above [1], wherein the compound represented by the above formula (1) or a salt thereof is a compound represented by the formula (6) or a salt thereof.

[式中,t及u分別獨立為2~6之整數] [where t and u are independent integers of 2~6, respectively]

[5]如上述[1]至[4]中任一項所記載之瀝青用添加劑,其中上述鹽為羧酸鹽。 [5] The additive for pitch according to any one of [1] to [4] wherein the salt is a carboxylate.

[6]如上述[1]至[5]中任一項所記載之瀝青用添加劑,其進而包含選自由石油系混合油及潤滑油所組成之群中之至少一種油。 [6] The additive for asphalt according to any one of the above [1] to [5], further comprising at least one selected from the group consisting of petroleum-based mixed oils and lubricating oils.

[7]如[6]所記載之瀝青用添加劑,其中式(1)所表示之化合物或其鹽之含量相對於油100重量份為0.01重量份~200重量份。 [7] The additive for pitch according to [6], wherein the content of the compound represented by the formula (1) or a salt thereof is from 0.01 part by weight to 200 parts by weight per 100 parts by weight of the oil.

[8]如[6]或[7]所記載之瀝青用添加劑,其進而包含界面活性劑。 [8] The additive for asphalt described in [6] or [7], which further comprises a surfactant.

[9]如[8]所記載之瀝青用添加劑,其中界面活性劑之含量相對於式(1)所表示之化合物或其鹽100重量份為0.01重量份~100重量份。 [9] The additive for pitch according to [8], wherein the content of the surfactant is 0.01 parts by weight to 100 parts by weight based on 100 parts by weight of the compound represented by the formula (1) or a salt thereof.

[10]一種瀝青組合物,其含有如上述[1]至[9]中任一項所記載之瀝青用添加劑、及瀝青。 [10] An asphalt composition containing the additive for pitch as described in any one of the above [1] to [9], and an asphalt.

[11]如上述[10]所記載之瀝青組合物,其相對於瀝青100重量份而含有0.005重量份~20重量份之式(1)所表示之化合物或其鹽。 [11] The asphalt composition according to the above [10], which contains 0.005 parts by weight to 20 parts by weight of the compound represented by the formula (1) or a salt thereof, based on 100 parts by weight of the pitch.

[12]一種道路舖面用瀝青混合物,其含有如上述[10]或[11]所記載之瀝青組合物與骨材。 [12] A bituminous mixture for road paving, comprising the bituminous composition and the aggregate according to the above [10] or [11].

[13]如上述[12]所記載之瀝青混合物,其用以於100~300℃之溫度下進行製造及施工。 [13] The asphalt mixture according to [12] above, which is used for production and construction at a temperature of from 100 to 300 °C.

[14]一種舖面體,其包含如上述[12]或[13]所記載之道路舖面用 瀝青混合物。 [14] A surfacing body comprising the road paving according to the above [12] or [13] Asphalt mixture.

根據本發明,可使瀝青與骨材之混合時及瀝青施工時之瀝青混合物之黏度降低,且可使瀝青與骨材之混合時及瀝青施工時之溫度下降。又,由於可提高骨材握持力,故而可獲得施工後之道路之穩定性優異之瀝青舖面體。 According to the present invention, the viscosity of the asphalt mixture during the mixing of the asphalt and the aggregate and the asphalt construction can be lowered, and the temperature of the asphalt and the aggregate and the temperature during the asphalt construction can be lowered. Moreover, since the grip strength of the aggregate can be improved, an asphalt pavement excellent in stability of the road after construction can be obtained.

以下,對本發明進行詳細說明。 Hereinafter, the present invention will be described in detail.

本發明之瀝青用添加劑含有以下之式(1)所表示之化合物或其鹽。 The additive for asphalt of the present invention contains a compound represented by the following formula (1) or a salt thereof.

[式中,n及m分別獨立為1~20之整數,較佳為2~6之整數,更佳為2~3之整數,l為1~4之整數,較佳為2~4之整數,更佳為2,p及q分別獨立為0或1,A1及A2分別獨立表示-CO-、-CH2-、-O-、-CO2-、或-OCO-,較佳為表示-CO-、或-CH2-, R1、R2、R3及R4分別獨立表示氫原子或可具有取代基之烴基,R2及R3亦可鍵結而形成環狀結構] [wherein, 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, and 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, and A 1 and A 2 independently represent -CO-, -CH 2 -, -O-, -CO 2 -, or -OCO-, preferably And -CO-, or -CH 2 -, R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a hydrocarbon group which may have a substituent, and R 2 and R 3 may be bonded to form a cyclic structure]

式(1)所表示之化合物或其鹽較佳為以下之式(3)所表示之化合物或其鹽。 The compound represented by the formula (1) or a salt thereof is preferably a compound represented by the following formula (3) or a salt thereof.

[式中,n及m分別獨立為1~20之整數,較佳為2~6之整數,更佳為2~3之整數,p及q分別獨立為0或1,A1及A2分別獨立表示-CO-、-CH2-、-O-、-CO2-、或-OCO-,較佳為表示-CO-、-CH2-,R1、R2、R3及R4分別獨立表示氫原子或可具有取代基之烴基,R2及R3亦可鍵結而形成環狀結構] [wherein, 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, and p and q are independently 0 or 1, respectively, and A 1 and A 2 are respectively Independently represents -CO-, -CH 2 -, -O-, -CO 2 -, or -OCO-, preferably -CO-, -CH 2 -, R 1 , R 2 , R 3 and R 4 respectively Independently represents a hydrogen atom or a hydrocarbon group which may have a substituent, and R 2 and R 3 may also bond to form a cyclic structure]

式(1)所表示之化合物或其鹽更佳為以下之式(4)及/或式(5)所表示之化合物或其鹽。 The compound represented by the formula (1) or a salt thereof is more preferably a compound represented by the following formula (4) and/or formula (5) or a salt thereof.

[式(4)及式(5)中,t及u分別獨立為1~20之整數,較佳為2~6之整數,更佳為2~3之整數,p及q分別獨立為0或1,較佳為0,R1、R2、R3及R4分別獨立表示氫原子或可具有取代基之烴基,R2及R3亦可鍵結而形成環狀結構] [In the formulas (4) and (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, and p and q are each independently 0 or 1, preferably 0, R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a hydrocarbon group which may have a substituent, and R 2 and R 3 may also bond to form a cyclic structure]

式(1)所表示之化合物或其鹽進而較佳為以下之式(6)所表示之化合物或其鹽。 The compound represented by the formula (1) or a salt thereof is more preferably a compound represented by the following formula (6) or a salt thereof.

[式中,t及u分別獨立為1~20之整數,較佳為2~6之整數,更佳為2~3之整數] [wherein, 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]

作為上述R1、R2、R3、R4、R5及R6之可具有取代基之烴基,較佳為可具有取代基之碳數1~30之烴基,可為飽和之烴基,亦可為不飽和之烴基,可為直鏈狀或支鏈狀之烴基,亦可於基之一部分具有環狀結構。又,作為上述取代基,可列舉含雜原子之基及鹵素原子。含雜原子之基可含1個雜原子,亦可含相同或不同之複數個雜原子,作為一例,可列舉羥基、碳數1~20之烷氧基。上述烴基中,作為碳數3~20之烴基之例,例如可列舉:丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基、二十烷基、硬脂基、月桂基、肉豆蔻基、2-乙基己基、9-十六碳烯基、順式-9-十八烷基、11-十八碳烯基、順式,順式-9,12-十八碳二烯基、9,12,15-十八碳三烯基、6,9,12-十八碳三烯基、9,11,13-十八碳三烯基、十八碳四烯基、二十碳烯基、11,14-二十碳二烯基、13,16-二十二碳二烯基、5,8,11,14-二十碳四烯基、順式-15-二十四碳烯基、二十碳五烯基、二十二碳五烯基、二十二碳六烯基、11-羥基-8-順式十七碳烯基等烷基或烯基;己基苯基、庚基苯基、辛基苯基、壬基苯基、癸基苯基、十一烷基苯基、十二烷基苯基、十三烷基苯基、十四烷基苯基、十五烷基苯基、十六烷基苯基、十七烷基苯基、十八烷基苯基等烷基苯基;及苯基。該等中,較佳為碳數3~20之烷基、苯基及碳數7~18之烷基苯基,更佳為碳數6~18之直鏈狀烷基。其中,進而較佳為己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、及11-羥基-8-順式十七碳烯基。再者,於本說明書中,上述烯基不僅為僅具有一個雙鍵者,亦包括具有兩個以上雙鍵者,例如烷二烯基、烷三烯基等。 The hydrocarbon group which may have a substituent of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 , preferably a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, may be a saturated hydrocarbon group, It may be an unsaturated hydrocarbon group, may be a linear or branched hydrocarbon group, or may have a cyclic structure in one part of the base. Further, examples of the substituent include a hetero atom-containing group and a halogen atom. The hetero atom-containing group may have one hetero atom, and may contain the same or different plural hetero atoms. Examples thereof include a hydroxyl group and an alkoxy group having 1 to 20 carbon atoms. In the above hydrocarbon group, examples of the hydrocarbon group having 3 to 20 carbon atoms include propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, decyl, undecyl, and dodecane. , tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, stearyl, lauryl, meat Myristyl, 2-ethylhexyl, 9-hexadecenyl, cis-9-octadecyl, 11-octadecenyl, cis, cis-9,12-octadecaene , 9,12,15-octadecatrienyl, 6,9,12-octadecatrienyl, 9,11,13-octadecatrienyl, octadecyltetraal, twenty Carbonyl, 11,14-eicosadienyl, 13,16-docosadienyl, 5,8,11,14-eicosatetraenyl, cis-15-twenty-four Alkenyl or alkenyl group such as hexenyl, eicosapentaenyl, docosylpentenyl, docosylhexenyl, 11-hydroxy-8-cis heptadecenyl; hexylphenyl , heptylphenyl, octylphenyl, nonylphenyl, nonylphenyl, undecylphenyl, dodecylphenyl, tridecylphenyl, tetradecylphenyl, ten Pentaalkylphenyl, An alkylphenyl group such as hexadecylphenyl, heptadecylphenyl or octadecylphenyl; 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. Of these, it is further preferably hexyl, heptyl, octyl, decyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, Heptadecyl, octadecyl, and 11-hydroxy-8-cis heptadecenyl. Furthermore, in the present specification, the above alkenyl group includes not only one double bond but also two or more double bonds, such as an alkadienyl group, an alkanetrienyl group and the like.

式(1)中,較佳為R1與R4相同,較佳為R2與R3相同,較佳為A1與A2相同,較佳為n與m相同,較佳為p與q相同。 In the formula (1), R 1 is preferably the same as R 4 , preferably R 2 is the same as R 3 , preferably A 1 is the same as A 2 , preferably n is the same as m, preferably p and q. the same.

式(3)中,較佳為R1與R4相同,較佳為R2與R3相同,較佳為A1與A2相同,較佳為n與m相同,較佳為p與q相同。 In the formula (3), R 1 and R 4 are preferably the same, preferably R 2 is the same as R 3 , preferably A 1 is the same as A 2 , preferably n is the same as m, preferably p and q. the same.

式(4)中,較佳為R1與R4相同,較佳為R2與R3相同,較佳為t與u相同。 In the formula (4), R 1 and R 4 are preferably the same, and it is preferred that R 2 is the same as R 3 , and it is preferable that t is the same as u.

式(5)中,較佳為R1與R4相同,較佳為R2與R3相同,較佳為t與u相同。 In the formula (5), R 1 and R 4 are preferably the same, and R 2 and R 3 are preferably the same, and t is preferably the same as u.

式(6)中,較佳為t與u相同。 In the formula (6), t is preferably the same as u.

作為式(1)所表示之化合物,較佳為:l為2~4之整數,n及m分別獨立為2~6之整數,p及q分別獨立為0或1,A1及A2分別獨立為-CO-、或-CH2-,R2及R3為氫原子,R1及R4分別獨立為氫原子或碳數3~20之烷基之式(1)所表示之化合物;l為2~4之整數,n及m分別獨立為2~6之整數,p及q分別獨立為0或1,A1及A2分別獨立為-CO-、或-CH2-,R2及R3為氫原子,R1及R4分別獨立為氫原子、苯基或碳數7~18之烷基苯基之式(1)所表示之化合物;l為2~4之整數,n及m分別獨立為2~6之整數,p及q分別獨立為0或1,A1及A2分別獨立為-CO-、或-CH2-,R2及R3為氫原子,R1及R4分別獨立為氫原子或碳數6~18之直鏈狀烷基之式(1)所表示之化合物;l為2~4之整數,n及m相同且為2~6之整數,p及q為1,A1及A2相同且為-CO-,R2及R3為氫原子,R1及R4相同且為碳數3~20之烷基之式(1)所表示之化合物;l為2~4之整數,n及m相同且為2~6之整數,p及q為1,A1及A2相同且為-CO-,R2及R3為氫原子,R1及R4相同且為碳數6~18之直鏈狀烷基之式(1)所表示之化合物;l為2~4之整數,n及m相同且為2~6之整數,p及q為0,R2及R3 為氫原子,R1及R4為氫原子、或相同且為碳數3~20之烷基之式(1)所表示之化合物;及l為2~4之整數,n及m相同且為2~6之整數,p及q為0,R2及R3為氫原子,R1及R4為氫原子、或相同且為碳數6~18之直鏈狀烷基之式(1)所表示之化合物。 As a compound represented by the formula (1), it is preferred that l is an integer of 2 to 4, and n and m are each independently an integer of 2 to 6, and p and q are each independently 0 or 1, and A 1 and A 2 are respectively a compound represented by the formula (1) which is independently -CO- or -CH 2 -, 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; l is an integer from 2 to 4, n and m are each an integer of 2 to 6, and p and q are each independently 0 or 1, and A 1 and A 2 are independently -CO-, or -CH 2 -, R 2 And R 3 is a hydrogen atom, and R 1 and R 4 each independently represent a compound represented by the formula (1) of a hydrogen atom, a phenyl group or an alkylphenyl group having 7 to 18 carbon atoms; and l is an integer of 2 to 4, n And m are independently an integer of 2-6, p and q are each independently 0 or 1, and A 1 and A 2 are independently -CO-, or -CH 2 -, and R 2 and R 3 are hydrogen atoms, R 1 And R 4 are each independently a hydrogen atom or a compound represented by the formula (1) having a linear alkyl group having 6 to 18 carbon atoms; 1 is an integer of 2 to 4, and n and m are the same and an integer of 2 to 6, p and q are 1, and A 1 and A 2 are the same and are -CO-, R 2 and R 3 are hydrogen atoms, and R 1 and R 4 are the same and are represented by the formula (1) having an alkyl group having 3 to 20 carbon atoms. a compound; l is an integer from 2 to 4, n and m The same and is an integer of 2 to 6, p and q is 1, and A 1 and A 2 is the same as CO-, R 2 and R 3 is a hydrogen atom, R 1 and R are the same and a carbon number of 46 to 18 a linear alkyl group of the compound represented by the formula (1); 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 a hydrogen atom. R 1 and R 4 are a compound represented by the formula (1) which is a hydrogen atom or the same and is an alkyl group having 3 to 20 carbon atoms; and l is an integer of 2 to 4, and n and m are the same and are 2 to 6 a compound represented by the formula (1) in which an integer, p and q are 0, R 2 and R 3 are a hydrogen atom, and R 1 and R 4 are a hydrogen atom or a linear alkyl group having the same carbon number of 6 to 18 .

作為式(3)所表示之化合物,較佳為:n及m分別獨立為2~6之整數,p及q分別獨立為0或1,A1及A2分別獨立為-CO-或-CH2-,R2及R3為氫原子,R1及R4分別獨立為氫原子或碳數3~20之烷基之式(3)所表示之化合物;n及m分別獨立為2~6之整數,p及q分別獨立為0或1,A1及A2分別獨立為-CO-或-CH2-,R2及R3為氫原子,R1及R4分別獨立為氫原子、苯基或碳數7~18之烷基苯基之式(3)所表示之化合物;n及m分別獨立為2~6之整數,p及q分別獨立為0或1,A1及A2分別獨立為-CO-、或-CH2-,R1及R3為氫原子,R1及R4分別獨立為氫原子或碳數6~18之直鏈狀烷基之式(3)所表示之化合物;n及m相同且為2~6之整數,p及q為1,A1及A2相同且為-CO-,R2及R3為氫原子,R1及R4相同且為碳數3~20之烷基之式(3)所表示之化合物;n及m相同且為2~6之整數,p及q為1,A1及A2相同且為-CO-,R2及R3為氫原子,R1及R4相同且為碳數6~18之直鏈狀烷基之式(3)所表示之化合物;n及m相同且為2~6之整數,p及q為0,R2及R3為氫原子,R1及R4為氫原子、或相同且為碳數3~20之烷基之式(3)所表示之化合物;及n及m相同且為2~6之整數,p及q為0,R2及R3為氫原子,R1及R4為氫原子、或相同且碳數6~18之直鏈狀烷基之式(3)所表示之化合物。 As the compound represented by the formula (3), it is preferred that n and m are each independently an integer of 2 to 6, and p and q are each independently 0 or 1, and A 1 and A 2 are independently -CO- or -CH, respectively. 2 -, R 2 and R 3 are each a hydrogen atom, and R 1 and R 4 each independently represent a compound represented by the formula (3) of a hydrogen atom or an alkyl group having 3 to 20 carbon atoms; n and m are each independently 2 to 6 The integers, p and q are each independently 0 or 1, and A 1 and A 2 are independently -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 compound represented by the formula (3) of a phenyl group or an alkylphenyl group having 7 to 18 carbon atoms; n and m are each independently an integer of 2 to 6, and p and q are each independently 0 or 1, and A 1 and A 2 are respectively Independently being -CO- or -CH 2 -, 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; a compound represented by n; m and m are the same and 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 R 3 are hydrogen atoms, and R 1 and R 4 are the same and a compound represented by the formula (3) having an alkyl group having 3 to 20 carbon atoms; n and m are the same and an integer of 2 to 6, p and q are 1, and A 1 and A 2 are the same and are -CO-, R 2 and R 3 are hydrogen atoms, R 1 and R 4 phases A compound represented by the formula (3) which is a linear alkyl group having 6 to 18 carbon atoms; 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 a hydrogen atom. And R 1 and R 4 are a compound represented by the formula (3) which is a hydrogen atom or the same and is an alkyl group having 3 to 20 carbon atoms; and n and m are the same and are integers of 2 to 6, and p and q are 0. A compound represented by the formula (3) wherein R 2 and R 3 are a hydrogen atom, and R 1 and R 4 are a hydrogen atom or a linear alkyl group having the same carbon number of 6 to 18.

作為式(4)所表示之化合物,較佳為:t及u分別獨立為2~6之整數,R2及R3為氫原子,R1及R4分別獨立為碳數3~20之烷基之式(4)所表示之化合物;t及u分別獨立為2~6之整數,R2及R3為氫原子,R1及R4分別獨立為碳數6~18之直鏈狀烷基之式(4)所表示之化合物;t及u相同且為2~6之整數,R2及R3為氫原子,R1及R4相同且為碳數3~20之烷基之式(4)所表示之化合物;及t及u相同且為2~6之整數,R2及R3為氫原子,R1及R4相同且為碳數6~18之直鏈狀烷基之式(4)所表示之化合物。 As a compound represented by the formula (4), t and u are each independently an integer of 2 to 6, and R 2 and R 3 are each a hydrogen atom, and R 1 and R 4 are each independently an alkyl group having 3 to 20 carbon atoms. a compound represented by the formula (4); t and u are each independently an integer of 2 to 6, R 2 and R 3 are each a hydrogen atom, 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, and R 1 and R 4 are the same and are an alkyl group having 3 to 20 carbon atoms. (4) the compound represented; and t and u are the same and are an integer of 2 to 6, R 2 and R 3 are a hydrogen atom, and R 1 and R 4 are the same and are a linear alkyl group having 6 to 18 carbon atoms. a compound represented by the formula (4).

作為式(5)所表示之化合物,較佳為:t及u分別獨立為2~6之整數,R2及R3為氫原子,R1及R4分別獨立為氫原子或碳數3~20之烷基之式(5)所表示之化合物;t及u分別獨立為2~6之整數,R2及R3為氫原子,R1及R4分別獨立為氫原子或碳數6~18之直鏈狀烷基之式(5)所表示之化合物;t及u相同且為2~6之整數,R2及R3為氫原子,R1及R4為氫原子、或相同且為碳數3~20之烷基之式(5)所表示之化合物;及t及u相同且為2~6之整數,R2及R3為氫原子,R1及R4為氫原子、或相同且為碳數6~18之直鏈狀烷基之式(5)所表示之化合物。 As a compound represented by the formula (5), it is preferred that t and u are each independently an integer of 2 to 6, R 2 and R 3 are each a hydrogen atom, and R 1 and R 4 are each independently a hydrogen atom or a carbon number of 3 to 3; a compound represented by the formula (5) of 20 alkyl groups; t and u are each independently an integer of 2 to 6, R 2 and R 3 are each a hydrogen atom, and R 1 and R 4 are each independently a hydrogen atom or a carbon number of 6~ a linear chain alkyl group of the formula (5); t and u are the same and an integer of 2 to 6, R 2 and R 3 are a hydrogen atom, and R 1 and R 4 are a hydrogen atom or the same a compound represented by the formula (5) having an alkyl group having 3 to 20 carbon atoms; and t and u are the same and an integer of 2 to 6, R 2 and R 3 are a hydrogen atom, and R 1 and R 4 are a hydrogen atom; Or a compound represented by the formula (5) which is the same and is a linear alkyl group having 6 to 18 carbon atoms.

本發明之瀝青用添加劑可含有上述化合物之鹽,例如上述化合物之羧酸或磺酸等有機酸之鹽,或鹽酸、氫溴酸、硫酸、磷酸等無機酸之鹽。於本發明中,作為上述化合物之羧酸鹽,可列舉己酸鹽、庚酸鹽、辛酸鹽、壬酸鹽、癸酸鹽、十一烷酸鹽、月桂酸鹽、十三烷酸鹽、肉豆蔻酸鹽、十五烷酸鹽、棕櫚酸鹽、十七烷酸鹽、硬脂酸鹽、α-次亞麻油酸鹽、亞麻油酸鹽、油酸鹽、蓖麻油酸鹽、檸檬酸鹽、琥珀酸鹽、酒石酸鹽、蘋果酸鹽、肉豆蔻油酸鹽、棕櫚油酸鹽、十六碳烯酸鹽、反油酸鹽、異油酸鹽、鱈油酸鹽、十二碳烯酸鹽、芥酸 鹽、二十四碳烯酸鹽、二十碳二烯酸鹽、二十二碳二烯酸鹽、十八碳三烯酸鹽、桐酸鹽、二十碳三烯酸鹽(Mead acid)、二十碳三烯酸鹽(eicosatrienoic acid)、十八碳四烯酸鹽、花生四烯酸鹽、二十碳四烯酸鹽(eicosatetraenoic acid)、二十二碳四烯酸鹽(adrenic acid)、十八碳五烯酸鹽、二十碳五烯酸鹽、二十二碳五烯酸鹽、鯡魚酸鹽、二十四碳五烯酸鹽、二十二碳六烯酸鹽、二十四碳六烯酸鹽、松香酸鹽、脫氫松香酸鹽、新松香酸鹽、海松酸鹽、異海松酸鹽、長葉松酸鹽等碳數2~30之飽和或不飽和羧酸鹽等。該等中,較佳為碳數8~24之飽和或不飽和羧酸鹽,更佳為碳數10~20之飽和或不飽和羧酸鹽,進而較佳為癸酸鹽、月桂酸鹽、肉豆蔻酸鹽、十五烷酸鹽、棕櫚酸鹽、十七烷酸鹽、硬脂酸鹽、油酸鹽、亞麻油酸鹽、次亞麻油酸鹽、及蓖麻油酸鹽。 The additive for pitch of the present invention may contain a salt of the above compound, for example, a salt of an organic acid such as a carboxylic acid or a sulfonic acid of the above compound, or a salt of an inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid or phosphoric acid. In the present invention, examples of the carboxylate of the above compound include hexanoate, heptanoate, octoate, decanoate, decanoate, undecanoate, laurate, and tridecanoate. Myristate, pentadecanoate, palmitate, heptadecanoate, stearate, alpha-linolenic acid oleate, linoleate, oleate, ricinoleate, citric acid Salt, succinate, tartrate, malate, myristate, palm oleate, hexadecenoate, oleate, isooleate, oleate, dodecene Acid salt Salt, tetracosenoate, eicosadienoate, behenodiate, octadecatrienoate, octoate, mead acid , eicosatrienoic acid, octadecatetraenoate, arachidonic acid, eicosatetraenoic acid, adrenic acid ), octadecapentate, eicosapentaenoate, docosapentaenoate, salmonate, docosapentaenoate, docosahexaenoate, A saturated or unsaturated carboxylic acid having 2 to 30 carbon atoms such as tetradecane hexaenoate, rosinate, dehydroabietic acid salt, neo-rosin acid salt, sea pine acid salt, isopimasone salt, long-leafed pine acid salt Salt and so on. Among these, a saturated or unsaturated carboxylic acid salt having a carbon number of 8 to 24 is preferred, and a saturated or unsaturated carboxylic acid salt having a carbon number of 10 to 20 is more preferred, and more preferably a decanoate or a laurate. Myristate, pentadecanoate, palmitate, heptadecanoate, stearate, oleate, linoleate, linolenate, and ricinoleate.

式(1)所表示之化合物例如可藉由Jaesung Choi等人之「Journal of Organic Chemistry」、1995年、第60卷、p.3266-3267中所記載之方法等公知方法而製造。 The compound represented by the formula (1) can be produced, for example, by a known method such as the method described in "Journal of Organic Chemistry" by Jaesung Choi et al., 1995, vol. 60, p. 3266-3267.

本發明之瀝青用添加劑可含有選自由石油系混合油及潤滑油所組成之群中之至少一種油。作為石油系混合油,可列舉芳香族碳數為總碳數之35重量%以上之芳香族系、環烷環碳數為總碳數之30~45重量%之環烷系、及鏈烷支鏈碳數為總碳數之50重量%以上之鏈烷系等。於本發明中,可適當地使用該等中之1種或2種以上。作為潤滑油,可列舉石油系潤滑油、合成潤滑油、脂肪油等,該等可適當地使用其中1種或2種以上。所謂石油系潤滑油係指藉由真空蒸餾將以原油常壓蒸餾之蒸餾殘油之形式獲得之沸點約30℃以上之重油分為各種餾出油,分別進行例如脫蠟、硫酸處理、溶劑萃取、脫瀝青、白土處理等適當精製處理,而精加工為最終製品。所謂合成潤滑油係指藉由有機合成法所製造,通常根據用途而分類之潤滑油,例如可列舉錠子 油、壓縮機油、電機油、渦輪機油、機油、引擎油、噴射引擎油、液壓油等。所謂脂肪油主要指混合至石油系潤滑油中,作為混成油而用於需要油性或乳化性之用途者。於本發明中,較佳為使用合成潤滑油。於將石油系混合油及潤滑油併用之情形時,其合計量為特定量即可。 The additive for asphalt of the present invention may contain at least one oil selected from the group consisting of petroleum-based mixed oils and lubricating oils. Examples of the petroleum-based mixed oil include an aromatic system having an aromatic carbon number of 35% by weight or more, a naphthenic system having a carbon number of 30 to 45% by weight of the total carbon number, and an alkane branch. The chain carbon number is an alkane system or the like having a total carbon number of 50% by weight or more. In the present invention, one or two or more of these may be used as appropriate. Examples of the lubricating oil include a petroleum-based lubricating oil, a synthetic lubricating oil, and a fatty oil. One or two or more of these may be used as appropriate. The term "oil-based lubricating oil" refers to a heavy oil having a boiling point of about 30 ° C or more obtained by distillation of crude oil at atmospheric distillation by vacuum distillation into various distillates, for example, dewaxing, sulfuric acid treatment, solvent extraction, respectively. , deasphalting, clay treatment, and other appropriate refining treatment, and finishing into the final product. The synthetic lubricating oil refers to a lubricating oil which is produced by an organic synthesis method and is generally classified according to the use, and for example, a spindle can be cited. Oil, compressor oil, motor oil, turbine oil, engine oil, engine oil, jet engine oil, hydraulic oil, etc. The fatty oil is mainly used in a petroleum-based lubricating oil, and is used as a blended oil for applications requiring oiliness or emulsifying properties. In the present invention, synthetic lubricating oil is preferably used. When the petroleum-based mixed oil and the lubricating oil are used in combination, the total amount thereof may be a specific amount.

於本發明之瀝青用添加劑包含油之情形時,式(1)所表示之化合物或其鹽之含量相對於油100重量份,通常為0.01重量份~200重量份,較佳為0.1重量份~150重量份,更佳為1~100重量份。 When the additive for asphalt of the present invention contains an oil, the content of the compound represented by the formula (1) or a salt thereof is usually from 0.01 part by weight to 200 parts by weight, preferably 0.1 part by weight, per 100 parts by weight of the oil. 150 parts by weight, more preferably 1 to 100 parts by weight.

本發明之瀝青用添加劑除上述油以外,亦可含有界面活性劑。作為界面活性劑,亦可使用離子性界面活性劑及非離子性界面活性劑之任一者。 The additive for pitch of the present invention may contain a surfactant in addition to the above oil. As the surfactant, any of an ionic surfactant and a nonionic surfactant can also be used.

作為離子性界面活性劑,可列舉以下者:陰離子界面活性劑,例如聚氧乙烯烷基醚磷酸(鹽)、聚氧乙烯烷基磺基琥珀酸鹽、烷基硫酸鹽、脂肪酸鹽等;陽離子界面活性劑,例如四級銨鹽、脂肪醯胺-胺等;兩性界面活性劑,例如烷基甜菜鹼、氧化烷基胺等。 The ionic surfactant may, for example, be an anionic surfactant such as polyoxyethylene alkyl ether phosphate (salt), polyoxyethylene alkyl sulfosuccinate, alkyl sulfate, fatty acid salt or the like; Surfactants such as quaternary ammonium salts, fatty amide amines, and the like; amphoteric surfactants such as alkyl betaines, alkylated amines, and the like.

作為非離子性界面活性劑,可列舉以下者:具有酯結構之酯系界面活性劑,例如山梨糖醇酐脂肪酸酯等;具有醚結構之醚系界面活性劑,例如聚氧伸烷基烷基醚、聚氧乙烯衍生物、聚氧乙烯聚氧丙烯二醇等。 Examples of the nonionic surfactant include an ester surfactant having an ester structure, such as a sorbitan fatty acid ester, and an ether surfactant having an ether structure, such as polyoxyalkylene oxide. Alkyl ether, polyoxyethylene derivative, polyoxyethylene polyoxypropylene diol, and the like.

本發明之瀝青用添加劑可含有2種以上之界面活性劑。於本發明之瀝青用添加劑含有界面活性劑之情形時,界面活性劑之含量相對於式(1)所表示之化合物或其鹽100重量份,通常為0.01重量份~100重量份,較佳為0.05重量份~80重量份,更佳為0.1重量份~50重量份。 The additive for asphalt of the present invention may contain two or more kinds of surfactants. In the case where the additive for the pitch of the present invention contains a surfactant, the content of the surfactant is usually from 0.01 part by weight to 100 parts by weight per 100 parts by weight of the compound represented by the formula (1) or a salt thereof, preferably 0.05 parts by weight to 80 parts by weight, more preferably 0.1 parts by weight to 50 parts by weight.

又,本發明亦提供一種含有上述瀝青用添加劑之瀝青組合物。作為本發明所使用之瀝青,並無特別限定,可列舉:湖瀝青等天然瀝青;摻合瀝青、石油溚、瀝青(pitch)、直餾瀝青、吹製瀝青、半吹製 瀝青、溶劑脫瀝青(例如丙烷脫瀝青)等石油瀝青。作為天然瀝青,例如可列舉硬瀝青、脆瀝青、特立尼達湖(Trinidad lake)瀝青等。該等瀝青可單獨使用,亦可將2種以上混合。又,向上述瀝青中以任意比率混入有人工瀝青者亦可用作原料瀝青。作為本發明中可使用之人工瀝青之一例,可列舉將石油系混合油與黏著賦予劑樹脂類以重量百分率計以石油系混合油:黏著賦予劑樹脂類=(0~100重量%):(100~0重量%)之比率進行調配而獲得者。 Further, the present invention also provides an asphalt composition containing the above-mentioned additive for asphalt. The bitumen used in the present invention is not particularly limited, and examples thereof include natural asphalt such as lake asphalt; blended asphalt, petroleum raft, pitch, straight-run asphalt, blown asphalt, and semi-blowing. Petroleum asphalt such as asphalt and solvent deasphalting (for example, propane deasphalting). Examples of the natural pitch include hard pitch, brittle pitch, Trinidad lake pitch, and the like. These pitches may be used singly or in combination of two or more. Further, the artificial asphalt may be used as the raw material pitch by mixing the artificial pitch into the above pitch at an arbitrary ratio. An example of the artificial pitch which can be used in the present invention is a petroleum-based mixed oil of a petroleum-based mixed oil and an adhesion-imparting agent resin: an adhesive-imparting agent resin (0 to 100% by weight): The ratio of 100 to 0% by weight is obtained by blending.

於本發明之瀝青組合物中,作為瀝青,可使用改質瀝青,例如改質瀝青I型、改質瀝青II型、改質瀝青H型、高黏度改質瀝青、較該高黏度改質瀝青黏度更高之改質瀝青等稱為再生瀝青之瀝青。 In the asphalt composition of the present invention, as the asphalt, modified asphalt may be used, such as modified asphalt type I, modified asphalt type II, modified asphalt type H, high viscosity modified asphalt, and higher viscosity modified asphalt. The modified asphalt with higher viscosity is called asphalt of recycled asphalt.

作為改質瀝青,可使用利用橡膠及/或熱塑性彈性體對直餾瀝青進行改質而獲得者。作為橡膠,可列舉天然橡膠或氯丁二烯橡膠。作為熱塑性彈性體,例如可列舉苯乙烯-丁二烯嵌段共聚物、苯乙烯-異戊二烯嵌段共聚物、乙烯-乙酸乙烯酯共聚物、乙烯-丙烯酸乙酯共聚物、丙烯酸酯、甲基丙烯酸酯、苯乙烯之均聚物及將該等組合之共聚物等,尤佳為苯乙烯-丁二烯嵌段共聚物、苯乙烯-異戊二烯嵌段共聚物。橡膠及熱塑性彈性體之合計相對於瀝青100重量份,以較佳為0.1~25重量份,更佳為1~20重量份,進而較佳為3~15重量份之比率使用。 As the modified asphalt, those obtained by modifying the straight-run asphalt with rubber and/or a thermoplastic elastomer can be used. As the rubber, natural rubber or chloroprene rubber can be cited. Examples of the thermoplastic elastomer include a styrene-butadiene block copolymer, a styrene-isoprene block copolymer, an ethylene-vinyl acetate copolymer, an ethylene-ethyl acrylate copolymer, and an acrylate. A methacrylate, a homopolymer of styrene, a copolymer of the above, and the like are preferably a styrene-butadiene block copolymer or a styrene-isoprene block copolymer. The total amount of the rubber and the thermoplastic elastomer is preferably from 0.1 to 25 parts by weight, more preferably from 1 to 20 parts by weight, still more preferably from 3 to 15 parts by weight, based on 100 parts by weight of the pitch.

作為再生瀝青,並無特別限定,可列舉包含用於對道路進行施工後之瀝青舖面廢料之瀝青。於本發明中,作為瀝青舖面廢料,可列舉各種,可列舉各種工程時產生之瀝青舖面廢料、例如地鐵工程、地下配管工程、道路舖面工程等時所產生之瀝青舖面廢料。根據本發明,於為該等任一種瀝青之情形時,均能夠降低加熱混合及施工時之瀝青之黏度,且發揮出亦提高骨材握持力之效果。 The recycled asphalt is not particularly limited, and examples thereof include asphalt which is used for asphalt paving waste after road construction. In the present invention, various types of asphalt paving waste can be cited, and various types of asphalt paving wastes generated during various engineering operations, such as subway works, underground piping works, road paving works, and the like, can be cited. According to the present invention, in the case of any of the above-mentioned asphalts, the viscosity of the asphalt during heating mixing and construction can be reduced, and the effect of improving the grip strength of the aggregate can be exerted.

於本發明之瀝青組合物中,只要不妨礙本發明之效果,則可調 配亦稱為加工處理油之石油系混合油。作為石油系混合油,可列舉芳香族碳數為總碳數之35重量%以上之芳香族系、環烷環碳數為總碳數之30~45重量%之環烷系、及鏈烷支鏈碳數為總碳數之50重量%以上之鏈烷系等。於本發明中,可適當地使用該等中之1種或2種以上。又,可使用潤滑油代替石油系混合油,又,亦可將兩者併用。於將兩者併用之情形時,其合計量為特定量即可。作為潤滑油,可列舉石油系潤滑油、合成潤滑油、脂肪油等,該等亦可適當地使用其中1種或2種以上。所謂石油系潤滑油係指藉由真空蒸餾將以原油常壓蒸餾之蒸餾殘油之形式獲得之沸點約30℃以上之重油分為各種餾出油,分別進行例如脫蠟、硫酸處理、溶劑萃取、脫瀝青、白土處理等適當精製處理,而精加工為最終製品。所謂合成潤滑油係指藉由有機合成法所製造,通常根據用途而分類之潤滑油,例如可列舉錠子油、壓縮機油、電機油、渦輪機油、機油、引擎油、噴射引擎油、液壓油等。所謂脂肪油主要指混合至石油系潤滑油中,作為混成油而用於需要油性或乳化性之用途者。於本發明中,較佳為使用合成潤滑油。 In the asphalt composition of the present invention, it is adjustable as long as it does not hinder the effect of the present invention. It is also known as a petroleum-based mixed oil for processing oil. Examples of the petroleum-based mixed oil include an aromatic system having an aromatic carbon number of 35% by weight or more, a naphthenic system having a carbon number of 30 to 45% by weight of the total carbon number, and an alkane branch. The chain carbon number is an alkane system or the like having a total carbon number of 50% by weight or more. In the present invention, one or two or more of these may be used as appropriate. Further, a lubricating oil may be used instead of the petroleum-based mixed oil, or both may be used in combination. When the two are used together, the total amount may be a specific amount. Examples of the lubricating oil include a petroleum-based lubricating oil, a synthetic lubricating oil, and a fatty oil. These may be used singly or in combination of two or more kinds. The term "oil-based lubricating oil" refers to a heavy oil having a boiling point of about 30 ° C or more obtained by distillation of crude oil at atmospheric distillation by vacuum distillation into various distillates, for example, dewaxing, sulfuric acid treatment, solvent extraction, respectively. , deasphalting, clay treatment, and other appropriate refining treatment, and finishing into the final product. The synthetic lubricating oil refers to a lubricating oil which is produced by an organic synthesis method and is generally classified according to the use, and examples thereof include spindle oil, compressor oil, motor oil, turbine oil, engine oil, engine oil, jet engine oil, and hydraulic pressure. Oil, etc. The fatty oil is mainly used in a petroleum-based lubricating oil, and is used as a blended oil for applications requiring oiliness or emulsifying properties. In the present invention, synthetic lubricating oil is preferably used.

於本發明之瀝青用添加劑及瀝青組合物中,只要不妨礙本發明之效果,則可進而調配各種添加劑。作為添加劑,並無特別限定,可列舉:石粉、滑石、碳酸鈣等填料,水泥、活性碳、熟石灰、甲基纖維素、聚乙烯醇等纖維質補強劑,2,6-二第三丁基-4-甲基苯酚等抗氧化劑,紫外線吸收劑,光穩定劑等。 In the asphalt additive and the asphalt composition of the present invention, various additives may be further prepared as long as the effects of the present invention are not impaired. The additive is not particularly limited, and examples thereof include fillers such as stone powder, talc, and calcium carbonate, and fibrous reinforcing agents such as cement, activated carbon, slaked lime, methyl cellulose, and polyvinyl alcohol, and 2,6-di-t-butyl group. An antioxidant such as -4-methylphenol, an ultraviolet absorber, a light stabilizer, and the like.

於本發明之瀝青用添加劑及瀝青組合物中,只要不妨礙本發明之效果,則亦可調配黏著賦予劑樹脂類。作為黏著賦予劑樹脂類,可使用天然系樹脂及合成系樹脂之任一者。作為天然系樹脂,可使用萜烯樹脂。又,作為合成系樹脂,可使用石油樹脂、薰草咔-茚樹脂、苯乙烯系樹脂等聚合系樹脂。作為石油樹脂,可列舉:以藉由石腦油分解生成物之蒸餾而分離之沸點為20~60℃之餾分(C5餾分)為主成分 之脂肪族系(C5系)石油樹脂、以同樣藉由石腦油分解生成物之蒸餾而分離之沸點為160~260℃之餾分(C9餾分)為主成分之芳香族系(C9系)石油樹脂、使該等C5系及C9系石油樹脂進行共聚合而生成之脂肪族/芳香族共聚合系(C5/C9系)石油樹脂、及主要使以藉由石腦油分解生成物之蒸餾而分離之高純度之二環戊二烯為主成分之脂環族系(DCPD系)石油樹脂萜烯類與酚類進行共聚合而生成之萜酚樹脂等。除該等以外,作為石油樹脂,可使用天然蠟、合成蠟、調配蠟等石油系,亦可同樣地使用煤系及聚合物系之各種蠟類。該等可列舉石蠟、微晶蠟、松蠟、費-托合成蠟、蓖麻蠟、氫化蠟、褐煤蠟、聚乙烯蠟、聚丙烯蠟等,於本發明中,可使用該等之1種或將2種以上混合而使用。 In the asphalt additive and the asphalt composition of the present invention, the adhesion-imparting resin may be blended as long as the effects of the present invention are not impaired. As the adhesion-imparting resin, any of a natural resin and a synthetic resin can be used. As the natural resin, a terpene resin can be used. Further, as the synthetic resin, a polymer resin such as a petroleum resin, a kumquat-tank resin, or a styrene resin can be used. The petroleum resin is a fraction having a boiling point of 20 to 60 ° C (C5 fraction) separated by distillation of a naphtha decomposition product. An aliphatic (C5-based) petroleum resin, an aromatic (C9-based) oil mainly composed of a fraction having a boiling point of 160 to 260 ° C (C9 fraction) separated by distillation of a naphtha decomposition product. An aliphatic/aromatic copolymerized (C5/C9-based) petroleum resin produced by copolymerizing these C5-based and C9-based petroleum resins, and mainly by distillation of a product obtained by decomposition of naphtha An alicyclic resin (DCPD-based), which is a high-purity dicyclopentadiene as a main component, is a nonylphenol resin obtained by copolymerizing a terpene resin with a phenol. In addition to these, as the petroleum resin, a petroleum system such as a natural wax, a synthetic wax, or a blending wax can be used, and various waxes of a coal-based or polymer-based system can be used in the same manner. Examples of such may include paraffin wax, microcrystalline wax, pine wax, Fischer-Tropsch wax, ramie wax, hydrogenated wax, montan wax, polyethylene wax, polypropylene wax, and the like. In the present invention, one of these may be used. Either two or more types are mixed and used.

於本發明之瀝青用添加劑及瀝青組合物中,只要不妨礙本發明之效果,則可進而調配硫或有機過氧化物。作為硫,可列舉微粉硫、膠態硫、沈澱硫、分散性硫等,並不限定於該等。作為有機過氧化物,例如可列舉過氧化二異丙苯、2,5-二甲基-2,5-二(第三丁基過氧基)己烷、1,3-二(2-第三丁基過氧基異丙基)苯、過氧化二第三丁基、2,5-二甲基-2,5-雙(第三丁基過氧基)-3-己炔等。 In the asphalt additive and the asphalt composition of the present invention, sulfur or an organic peroxide may be further formulated as long as the effects of the present invention are not impaired. Examples of the sulfur include fine powder sulfur, colloidal sulfur, precipitated sulfur, and dispersible sulfur, and are not limited thereto. Examples of the organic peroxide include dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, and 1,3-bis(2- Tributylperoxyisopropyl)benzene, ditributyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)-3-hexyne, and the like.

又,本發明之瀝青用添加劑及含有其之瀝青組合物亦可以不損害本發明之效果之量含有水。 Further, the additive for asphalt 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.

本發明之瀝青組合物相對於瀝青100重量份,含有較佳為0.005重量份~20重量份,更佳為0.01重量份~15重量份,進而較佳為0.1重量份~10重量份之式(1)所表示之化合物或其鹽。 The bituminous composition of the present invention contains preferably from 0.005 parts by weight to 20 parts by weight, more preferably from 0.01 part by weight to 15 parts by weight, even more preferably from 0.1 part by weight to 10 parts by weight, based on 100 parts by weight of the bitumen ( 1) A compound or a salt thereof.

本發明之瀝青組合物於添加骨材之前,亦可應用向瀝青中添加及混合本發明之瀝青用添加劑的預混法、及於瀝青混合場所將瀝青與骨材混合時投入本發明之添加劑之廠拌法之任一方法。於預混法之情形時,有省去於瀝青混合場所投入材料之勞力與時間之優點。於預混法中,可使用均質攪拌機、分散攪拌機、槳式混合器、帶式混合機、 螺旋式攪拌機、行星式混合機、真空逆流攪拌機等將各成分進行混合。於廠拌法之情形時,可使用捏泥攪拌機、旋流式攪拌機、螺旋式攪拌機等對各成分進行攪拌及混合。 The asphalt composition of the present invention may also be applied to a premixing method of adding and mixing the additive for asphalt of the present invention to the asphalt before adding the aggregate, and to the additive of the present invention when the asphalt and the aggregate are mixed in the asphalt mixing place. Any method of factory mixing. In the case of the premixing method, there is an advantage in eliminating the labor and time of inputting materials in the asphalt mixing place. In the premixing method, a homomixer, a dispersing mixer, a paddle mixer, a belt mixer, The components are mixed by a screw mixer, a planetary mixer, a vacuum countercurrent mixer, or the like. In the case of the factory mixing method, each component may be stirred and mixed using a kneading mixer, a cyclone mixer, a screw mixer, or the like.

又,本發明之瀝青用添加劑向瀝青中之添加方法並無特別限定,於對在100~300℃,較佳為120~280℃,更佳為150~250℃下進行加熱溶融後之瀝青或瀝青與骨材之混合物進行攪拌下,添加特定量即可。又,由於本發明之添加劑對瀝青之溶解性、親和性良好,於熱對流或搬運時之振動程度下亦被混合,故而亦可不進行攪拌,但由於有時要求即效性,故而較佳為進行攪拌混合。進而,於向瀝青中添加橡膠及/或熱塑性彈性體之情形時,本發明之瀝青用添加劑與橡膠及/或熱塑性彈性體可同時向加熱後之瀝青中添加,亦可分別添加。於分別添加之情形時,其添加順序並無特別限定。 Moreover, the method of adding the additive for pitch of the present invention to the pitch is not particularly limited, and the pitch or the mixture is heated and melted at 100 to 300 ° C, preferably 120 to 280 ° C, more preferably 150 to 250 ° C. When a mixture of asphalt and aggregate is stirred, a specific amount may be added. Further, since the additive of the present invention has good solubility and affinity for pitch, it is also mixed under the degree of vibration during heat convection or transportation, and therefore, stirring may not be performed. However, it is preferable to require immediate effect. Mix and mix. Further, in the case where a rubber and/or a thermoplastic elastomer is added to the pitch, the additive for pitch of the present invention and the rubber and/or the thermoplastic elastomer may be simultaneously added to the heated pitch or may be separately added. When it is added separately, the order of addition is not specifically limited.

含有本發明之瀝青用添加劑之瀝青組合物可藉由使用例如布氏B型黏度計,並根據其組成或加熱混合溫度、施工溫度等設定測定條件,而確認黏度下降。於改質瀝青H型之情形時,可於例如150℃之溫度下測定黏度。又,於再生瀝青之情形時,可於例如170℃之溫度下測定黏度。 The bituminous composition containing the additive for pitch of the present invention can be confirmed by setting the measurement conditions according to the composition, the heating and mixing temperature, the application temperature, and the like using, for example, a Brookfield B-type viscometer. In the case of upgrading the bitumen H type, the viscosity can be measured, for example, at a temperature of 150 °C. Further, in the case of reclaiming asphalt, the viscosity can be measured at, for example, a temperature of 170 °C.

含有本發明之瀝青用添加劑之瀝青組合物可用於道路舖面材料、蓋屋頂用材料、防水材料等。本發明之瀝青組合物由於骨材握持力優異,故而於瀝青混合物中較佳地使用,且適合於使用道路舖面用瀝青混合物之舖面、尤其是高空隙率之排水性舖面及透水性舖面、高負荷交通道路舖面。 The bituminous composition containing the additive for asphalt of the present invention can be used for road paving materials, roofing materials, waterproof materials, and the like. The bituminous composition of the present invention is preferably used in an asphalt mixture because of its excellent grip strength, and is suitable for use in the paving of road paving asphalt mixtures, especially high porosity and drainage pavements and water permeable pavements. High-load traffic road pavement.

本發明之瀝青混合物可藉由將本發明之瀝青組合物與碎石等骨材進行混合而製造。作為骨材,只要為依據瀝青舖面綱要、舖面設計施工指南、舖面施工手冊(均為公益社團法人日本道路協會發行)中所記載者,則無特別限定,可列舉碎石、砂石、砂、礦渣及填料等。 又,除該等以外亦可不論材質等而使用各種低品質骨材或再生骨材等。骨材可單獨使用,或以2種以上之混合物之形式使用。於以2種以上之混合物之形式使用之情形時,各骨材之種類及調配比率可根據舖面體之必要強度、舖面體之部位、透水性等進行適當選擇。本發明之瀝青混合物較佳為包含瀝青組合物與含有碎石、砂及填料之骨材。於本發明中,瀝青組合物與骨材之調配比率以瀝青混合物之總重量為基準,較佳為1~15重量%之瀝青組合物、99~85重量%之骨材,更佳為1~10重量%之瀝青組合物、99~90重量%之骨材。 The asphalt mixture of the present invention can be produced by mixing the asphalt composition of the present invention with an aggregate such as crushed stone. As the aggregate, there is no particular limitation as long as it is described in the asphalt paving outline, the pavement design and construction guide, and the pavement construction manual (issued by the Japan Road Association, which is a public interest corporation), and may include gravel, sand, sand, Slag and fillers. In addition to these materials, various low-quality aggregates, recycled aggregates, and the like can be used regardless of the material or the like. The aggregate may be used singly or in the form of a mixture of two or more. When it is used in the form of a mixture of two or more kinds, the type and the blending ratio of each of the aggregates can be appropriately selected depending on the necessary strength of the paving body, the location of the paving body, the water permeability, and the like. The asphalt mixture of the present invention preferably comprises an asphalt composition and an aggregate comprising gravel, sand and filler. In the present invention, the blending ratio of the asphalt composition to the aggregate is preferably from 1 to 15% by weight of the asphalt composition, from 99 to 85% by weight of the aggregate, based on the total weight of the asphalt mixture, more preferably 1~ 10% by weight of the asphalt composition, 99 to 90% by weight of the aggregate.

以下,揭示實施例,更詳細地說明本發明,但本發明並不限定於該等實施例。 Hereinafter, the present invention will be described in more detail by way of examples, but the invention is not limited to the examples.

[實施例] [Examples]

劣化瀝青 Degraded asphalt

使用新直餾瀝青60~80(JX日礦日石能源公司製造),依據JISK 2207之薄膜加熱劣化試驗,於163℃下進行加熱劣化5小時後,依據舖面調查、試驗法手冊(公益社團法人日本道路協會編)中記載之加壓劣化試驗,於105℃及氣壓2.10MPa下,經過21小時製成劣化瀝青。由本方法製成之劣化瀝青由於將瀝青置於屋外大致再現約使用5年後之劣化狀態,認為對於製作劣化材料有效,故而設為再生瀝青之模擬。 Using the new straight-run asphalt 60-80 (manufactured by JX Nippon Mining & Energy Co., Ltd.), according to the film heating deterioration test of JIS K 2207, after heating and degrading at 163 ° C for 5 hours, according to the pavement survey and test method manual (public interest corporation) The pressure deterioration test described in the Japan Road Association) was made into a deteriorated pitch at 105 ° C and a pressure of 2.10 MPa over 21 hours. The deteriorated pitch produced by the method is considered to be effective for producing a deteriorated material because the asphalt is placed outside the house and is substantially regenerated in a state of deterioration for about five years, so that it is a simulation of the recycled asphalt.

黏度測定 Viscosity measurement

(實施例1) (Example 1)

使用布氏B型黏度計,於160℃下對添加相對於劣化瀝青100重量份為5重量份之雙(3-胺基丙基)二硫醚之瀝青組合物攪拌3分鐘後,測定黏度。其後,繼續測定於110℃下之黏度。將結果示於表1。再者,表中之黏度之單位為厘泊(cP)。 The viscosity was measured by adding a pitch composition of 5 parts by weight of bis(3-aminopropyl)disulfide to 100 parts by weight of the deteriorated pitch at 160 ° C for 3 minutes using a Brookfield B-type viscometer. Thereafter, the viscosity at 110 ° C was continuously measured. The results are shown in Table 1. Furthermore, the unit of viscosity in the table is centipoise (cP).

(實施例2~3) (Examples 2 to 3)

除了將雙(3-胺基丙基)二硫醚變更為表1中記載之化合物以外, 與實施例1同樣地獲得瀝青組合物,並實施黏度測定。 Except that the bis(3-aminopropyl) disulfide was changed to the compound described in Table 1, The asphalt composition was obtained in the same manner as in Example 1 and the viscosity was measured.

(比較例1) (Comparative Example 1)

除了未使用雙(3-胺基丙基)二硫醚以外,與實施例1同樣地獲得瀝青組合物,並實施黏度測定。 An asphalt composition was obtained in the same manner as in Example 1 except that bis(3-aminopropyl)disulfide was not used, and viscosity measurement was carried out.

(比較例2) (Comparative Example 2)

除了將雙(3-胺基丙基)二硫醚變更為昭和殼牌石油公司製造之礦物油(40℃下之動黏度(JIS K 2283)=257mm2/s,流動點(JIS K 2269)=-22.5℃)以外,與實施例1同樣地獲得瀝青組合物,並實施黏度測定。 In addition to the conversion of bis(3-aminopropyl) disulfide to mineral oil manufactured by Showa Shell Oil Company (kinetic viscosity at 40 ° C (JIS K 2283) = 257 mm 2 /s, pour point (JIS K 2269) = The asphalt composition was obtained in the same manner as in Example 1 except for -22.5 ° C), and the viscosity was measured.

(實施例4~10) (Examples 4 to 10)

除了將劣化瀝青變更為改質瀝青H型,將雙(3-胺基丙基)二硫醚變更為表2中記載之化合物,將黏度測定之溫度變更為170℃及150℃以外,與實施例1同樣地獲得瀝青組合物,並實施黏度測定。 In addition to changing the deteriorated pitch to the modified bitumen H type, the bis(3-aminopropyl) disulfide was changed to the compound described in Table 2, and the temperature of the viscosity measurement was changed to 170 ° C and 150 ° C, and the implementation was carried out. Example 1 A bituminous composition was obtained in the same manner, and viscosity measurement was carried out.

(比較例3) (Comparative Example 3)

除了未使用雙(3-胺基丙基)二硫醚以外,與實施例4同樣地獲得瀝青組合物,並實施黏度測定。 The 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.

(比較例4) (Comparative Example 4)

除了將雙(3-胺基丙基)二硫醚變更為昭和殼牌石油公司製造之礦物油(40℃下之動黏度(JIS K 2283)=257mm2/s,流動點(JIS K 2269)=-22.5℃)以外,與實施例4同樣地獲得瀝青組合物,並實施黏度測定。 In addition to the conversion of bis(3-aminopropyl) disulfide to mineral oil manufactured by Showa Shell Oil Company (kinetic viscosity at 40 ° C (JIS K 2283) = 257 mm 2 /s, pour point (JIS K 2269) = An asphalt composition was obtained in the same manner as in Example 4 except for -22.5 ° C), and viscosity measurement was performed.

(比較例5) (Comparative Example 5)

除了將雙(3-胺基丙基)二硫醚變更為硬脂酸以外,與實施例4同樣地獲得瀝青組合物,並實施黏度測定。 The asphalt composition was obtained in the same manner as in Example 4 except that the bis(3-aminopropyl)disulfide was changed to stearic acid, and the viscosity was measured.

(實施例11) (Example 11)

於170℃下將骨材(碎石:砂:填料之重量比為約80:約15:約5 之混合物)100重量份與實施例4中製成之瀝青組合物5重量份進行混合後,夯實而獲得空隙率為20%之排水性瀝青混合物(骨材最大粒徑13mm)。將所獲得之瀝青混合物之特性示於表3。瀝青混合物之穩定性係藉由馬歇爾穩定度試驗而進行評價。關於馬歇爾穩定度,數值較高時穩定性優異。瀝青混合物之骨材握持力係藉由肯塔堡試驗進行評價。於肯塔堡試驗中,數值較低時因骨材飛散所致之損失率較低。 The weight ratio of the aggregate (gravel: sand: filler) at 170 ° C is about 80: about 15: about 5 The mixture was mixed with 5 parts by weight of the asphalt composition prepared in Example 4, and then tamped to obtain a drainage asphalt mixture having a void ratio of 20% (maximum particle diameter of the aggregate of 13 mm). The properties of the obtained asphalt mixture are shown in Table 3. The stability of the asphalt mixture was evaluated by the Marshall stability test. Regarding the Marshall stability, the stability is excellent when the value is high. The grip strength of the asphalt mixture was evaluated by the Kentaberg test. In the Kentaberg test, the loss rate due to the scattering of aggregates was lower at lower values.

(比較例6~8) (Comparative examples 6 to 8)

除了使用比較例3~5中製成之瀝青組合物代替實施例4中製成之瀝青組合物以外,與實施例11同樣地獲得排水性瀝青混合物,並實施黏度測定。將結果示於表3。 A drain 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. The results are shown in Table 3.

(實施例12) (Embodiment 12)

除了將實施例4中製成之瀝青組合物變更為實施例5中製成之瀝青組合物,將混合之溫度變更為150℃以外,與實施例11同樣地獲得排水性瀝青混合物,並實施排水性瀝青混合物之穩定性及骨材握持力之評價。 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 temperature of the mixture was changed to 150 ° C. Evaluation of the stability of the asphalt mixture and the grip strength of the aggregate.

(比較例9~10) (Comparative examples 9 to 10)

除了變更為比較例3~4中製成之瀝青組合物代替實施例5中製成之瀝青組合物以外,與實施例12同樣地獲得排水性瀝青混合物,並實施排水性瀝青混合物之穩定性及骨材握持力之評價。 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 changed to the asphalt composition prepared in Example 5, and the stability of the drainage asphalt mixture was carried out. Evaluation of the grip strength of the aggregate.

(實施例13) (Example 13)

於室溫下充分混合相對於昭和殼牌石油公司製造之礦物油(40℃下之動黏度(JIS K 2283)=257mm2/s,流動點(JIS K 2269)=-22.5℃)100重量份,為25重量份之雙(3-胺基丙基)二硫醚、及7.5重量份之山梨糖醇酐脂肪酸酯,從而獲得添加劑A。 100 parts by weight of mineral oil (JIS K 2283) = 257 mm 2 /s, pour point (JIS K 2269) = -22.5 ° C) manufactured by Showa Shell Oil Co., Ltd. at room temperature, It is 25 parts by weight of bis(3-aminopropyl)disulfide, and 7.5 parts by weight of sorbitan fatty acid ester, thereby obtaining the additive A.

除了使用所獲得之添加劑A5重量份代替雙(3-胺基丙基)二硫醚5重量份以外,與實施例1同樣地獲得瀝青組合物。並對所獲得之瀝青 組合物實施黏度測定。將結果示於表1。 An asphalt composition was obtained in the same manner as in Example 1 except that 5 parts by weight of the additive A was used instead of 5 parts by weight of bis(3-aminopropyl)disulfide. And the obtained asphalt The composition was subjected to viscosity measurement. The results are shown in Table 1.

(實施例14) (Example 14)

除了使用實施例13中製成之瀝青組合物代替實施例4中製成之瀝青組合物以外,與實施例11同樣地獲得排水性瀝青混合物。對所獲得之排水性瀝青混合物實施黏度測定。將結果示於表3。 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 produced in Example 4. The viscosity of the obtained drainage asphalt mixture was measured. The results are shown in Table 3.

再者,於實施例及比較例中,瀝青組合物及瀝青混合物之物性係藉由以下方式進行測定或定義。 Further, in the examples and comparative examples, the physical properties of the asphalt composition and the asphalt mixture were measured or defined in the following manner.

<瀝青組合物之測定> <Measurement of Asphalt Composition>

(黏度) (viscosity)

使用布氏B型黏度計,於各表中記載之溫度下進行測定。 The measurement was carried out using a Brookfield B-type viscometer at the temperatures described in the respective tables.

<瀝青混合物之測定> <Measurement of asphalt mixture>

(馬歇爾穩定度試驗及肯塔堡試驗) (Marshall Stability Test and Kentaberg Test)

依據舖面試驗法手冊(公益社團法人日本道路協會發行)中記載之試驗方法進行。夯實係對各實施例及比較例中製作之瀝青混合物以空隙率成為20%之方式於較混合溫度低15℃之溫度下進行。關於密實度,作為夯實前之密度相對於夯實後之瀝青混合物之密度之比率即空隙率以%表示。 It is carried out according to the test method described in the Handbook of the Pavement Test Method (issued by the Japan Road Association). The tamping system was carried out at a temperature lower than the mixing temperature by 15 ° C in such a manner that the pitch mixture produced in each of the examples and the comparative examples was 20%. Regarding the degree of compaction, the ratio of the density before compaction to the density of the asphalt mixture after compaction, that is, the void ratio is expressed in %.

由表1或表2明確,藉由混合本發明之瀝青用添加劑(實施例1~10及實施例13),與未加入添加劑之比較例1或3相比,大幅降低了瀝青混合物之黏度。又,由比較例2、4及5明確,本發明之瀝青用添加劑於降低瀝青混合物之黏度之方面遠優於油或蠟。 As is clear from Table 1 or Table 2, by mixing the additives for asphalt of the present invention (Examples 1 to 10 and Example 13), the viscosity of the asphalt mixture was drastically reduced as compared with Comparative Example 1 or 3 to which no additive was added. Further, it is clear from Comparative Examples 2, 4 and 5 that the additive for asphalt of the present invention is far superior to oil or wax in reducing the viscosity of the asphalt mixture.

又,由表3或表4明確,含有本發明之瀝青用添加劑之瀝青混合物於表示瀝青混合物之穩定性之馬歇爾穩定度及表示骨材握持力之損失率之兩方面優異。 Further, it is clear from Table 3 or Table 4 that the asphalt mixture containing the additive for asphalt of the present invention is excellent in both Marshall stability indicating the stability of the asphalt mixture and loss rate indicating the grip strength of the aggregate.

Claims (14)

一種瀝青用添加劑,其含有式(1)所表示之化合物或其鹽, [式中,n及m分別獨立為1~20之整數,l為1~4之整數,p及q分別獨立為0或1,A1及A2分別獨立表示-CO-、-CH2-、-O-、-CO2-、或-OCO-,R1、R2、R3及R4分別獨立表示氫原子、或可具有取代基之烴基,R2及R3亦可鍵結而形成環狀結構]。 An additive for asphalt containing a compound represented by formula (1) or a salt thereof, [wherein, n and m are each independently an integer from 1 to 20, l is an integer from 1 to 4, and p and q are each independently 0 or 1, and A 1 and A 2 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 a hydrocarbon group which may have a substituent, and R 2 and R 3 may also be bonded. Form a ring structure]. 如請求項1之瀝青用添加劑,其中上述式(1)所表示之化合物或其鹽為式(3)所表示之化合物或其鹽, [式中,n及m分別獨立為1~20之整數,p及q分別獨立為0或1,A1及A2分別獨立表示-CO-、-CH2-、-O-、-CO2-、或-OCO-,R1、R2、R3及R4分別獨立表示氫原子、或可具有取代基之烴基,R2及R3亦可鍵結而形成環狀結構]。 The additive for asphalt according to claim 1, wherein the compound represented by the above formula (1) or a salt thereof is a compound represented by the formula (3) or a salt thereof, [wherein, n and m are each independently an integer from 1 to 20, and p and q are each independently 0 or 1, and A 1 and A 2 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 a hydrocarbon group which may have a substituent, and R 2 and R 3 may be bonded to each other to form a cyclic structure]. 如請求項1之瀝青用添加劑,其中上述式(1)所表示之化合物或其鹽為式(4)所表示之化合物或其鹽、或式(5)所表示之化合物或其鹽, [式中,t及u分別獨立為2~6之整數, p及q分別獨立為0或1,R1、R2、R3及R4分別獨立表示氫原子、或可具有取代基之烴基,R2及R3亦可鍵結而形成環狀結構]。 The additive for the bitumen of claim 1, wherein the compound represented by the above 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, [wherein, t and u are each independently an integer of 2 to 6, and p and q are each independently 0 or 1, and R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a hydrocarbon group which may have a substituent. R 2 and R 3 may also be bonded to form a cyclic structure]. 如請求項1之瀝青用添加劑,其中上述式(1)所表示之化合物或其鹽為式(6)所表示之化合物或其鹽, [式中,t及u分別獨立為2~6之整數]。 The additive for asphalt according to claim 1, wherein the compound represented by the above formula (1) or a salt thereof is a compound represented by the formula (6) or a salt thereof, [wherein, t and u are each independently an integer of 2 to 6]. 如請求項1至4中任一項之瀝青用添加劑,其中上述鹽為羧酸鹽。 The additive for asphalt according to any one of claims 1 to 4, wherein the above salt is a carboxylate. 如請求項1至5中任一項之瀝青用添加劑,其進而包含選自由石油系混合油及潤滑油所組成之群中之至少一種油。 The additive for asphalt according to any one of claims 1 to 5, which further comprises at least one oil selected from the group consisting of petroleum-based mixed oils and lubricating oils. 如請求項6之瀝青添加劑,其中式(1)所表示之化合物或其鹽之含量相對於油100重量份為0.01重量份~200重量份。 The asphalt additive of claim 6, wherein the content of the compound represented by the formula (1) or a salt thereof is from 0.01 part by weight to 200 parts by weight based on 100 parts by weight of the oil. 如請求項6或7之瀝青用添加劑,其進而包含界面活性劑。 An additive for asphalt according to claim 6 or 7, which further comprises a surfactant. 如請求項8之瀝青用添加劑,其中界面活性劑之含量相對於式(1)所表示之化合物或其鹽100重量份為0.01重量份~100重量份。 The additive for asphalt according to claim 8, wherein the content of the surfactant is from 0.01 part by weight to 100 parts by weight based on 100 parts by weight of the compound represented by the formula (1) or a salt thereof. 一種瀝青組合物,其含有如請求項1至9中任一項之瀝青用添加劑、與瀝青。 An asphalt composition comprising the additive for asphalt according to any one of claims 1 to 9, and asphalt. 如請求項10之瀝青組合物,其相對於瀝青100重量份而含有0.005 重量份~20重量份之式(1)所表示之化合物或其鹽。 The asphalt composition of claim 10, which contains 0.005 with respect to 100 parts by weight of the asphalt The compound represented by the formula (1) or a salt thereof in an amount of up to 20 parts by weight. 一種道路舖面用瀝青混合物,其含有如請求項10或11之瀝青組合物與骨材。 An asphalt mixture for road paving comprising the asphalt composition and aggregate of claim 10 or 11. 如請求項12之瀝青混合物,其用以於100~300℃之溫度下進行製造及施工。 The asphalt mixture of claim 12, which is used for manufacturing and construction at a temperature of 100 to 300 °C. 一種舖面體,其包含如請求項12或13之道路舖面用瀝青混合物。 A surfacing body comprising the asphalt mixture for road paving as claimed in claim 12 or 13.
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JPH0892486A (en) * 1994-09-20 1996-04-09 J S R Shell Elastomer Kk Asphalt composition
FR2740140B1 (en) * 1995-10-19 1997-11-21 Elf Antar France METHOD FOR PREPARING BITUMEN/FUNCTIONALIZED ELASTOMER COMPOSITIONS WITH A WIDE PLASTICITY RANGE, APPLICATION OF THE COMPOSITIONS OBTAINED TO THE PRODUCING OF COATINGS AND STOCK SOLUTION FOR THIS PREPARATION
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