Anti-adhesion agent for asphalt mixtures

Abstract

To provide an anti-adhesion agent for asphalt mixtures that suppresses strong adhesion of asphalt, that does not dissolve asphalt, and that forms a uniform solution when diluted with a solvent.SOLUTION: An anti-adhesion agent for asphalt mixtures contains a compound (A) represented by the following formula (1): R1O-(EO)m(PO)n-H. [In the formula, the R1O- group is a group derived from a C8-16 straight-chain secondary alcohol by removing the hydrogen atom from the hydroxyl group; EO represents an oxyethylene group; PO represents an oxypropylene group; and m is the average number of moles of the added oxyethylene groups, and n is the average number of moles of the added oxypropylene groups, satisfying 4≤m≤20, 0≤n≤20, and 4≤m+n≤30.]SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to an asphalt composite adhesion inhibitor.

Background Art

[0002] For pavements such as motorways, parking lots, freight yards, and sidewalks, asphalt paving using an asphalt composition is carried out because it is relatively easy to lay and the time from the start of the paving work to the start of traffic can be shortened. In this asphalt paving, since the road surface is formed by an asphalt mixture in which aggregates are bound with asphalt, the paved road has good hardness and durability.

[0003] Since asphalt has high adhesiveness, it functions as a binder component in the asphalt mixture. However, due to its high adhesiveness, adhesion to unintended locations may become a problem. For example, when compacting with a tire roller during asphalt paving construction, asphalt may adhere to the tire roller. To avoid such problems, various asphalt composite adhesion inhibitors have been proposed.

[0004] Patent Document 1 discloses an asphalt composite adhesion inhibitor that has a high anti-adhesion effect and peeling effect on asphalt composites, is stable at normal temperature or low temperature even after dilution with water, and contains an alkylene oxide derivative with a specific structure and a liquid paraffin having predetermined physical properties in specific ratios. Patent Document 2 discloses an asphalt composite adhesion inhibitor that can stably exhibit an anti-adhesion effect on asphalt composites, particularly an anti-adhesion effect and peeling effect in a state where mineral oil is adhered, over time, and is difficult to separate at normal temperature or low temperature even after dilution with water, and contains a specific polyoxyethylene derivative and a monoterpenoid in specific ratios. Patent Document 3 discloses an anti-adhesion agent for asphalt mixtures, which causes the asphalt mixture on the loading platform of a dump truck or the like to slide out at a low angle, is difficult to stain the loading platform, and has excellent stability at or below room temperature even after dilution with water. The anti-adhesion agent for asphalt mixtures contains a specific polyoxyalkylene monoalkyl ether and a specific nonionic surfactant. Patent Document 4 discloses an anti-adhesion agent for asphalt mixtures, which has high wettability to the metal surface during spraying or coating, has a high anti-adhesion effect and peeling effect on asphalt mixtures, and can be easily emulsified when diluted with water. The anti-adhesion agent for asphalt mixtures contains specific fats and oils, a specific monohydric water-soluble alcohol, and a specific nonionic surfactant in specific proportions. Patent Document 5 discloses an anti-adhesion agent that is excellent in preventing the adhesion of construction materials for asphalt and concrete to construction tools and machinery for asphalt and concrete and in removing the adhered substances, suppresses adverse effects on the properties of asphalt and concrete, and can finish the construction shape and quality in a more stable state. The anti-adhesion agent contains glycols with a predetermined structure.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Patent Document 5

Summary of the Invention

Problems to be Solved by the Invention

[0006] In recent years, due to the increasing awareness of environmental issues, the high durability and long lifespan of asphalt pavement have attracted attention, and the construction of asphalt mixtures applied with new technologies has been actively carried out. On the other hand, such new asphalt mixtures may exhibit different adhesion behaviors from conventional asphalt mixtures, and existing anti-adhesion agents may not be able to sufficiently suppress the adhesion of the mixture to rollers, etc. In particular, tire rollers, due to aging and other reasons, the smoothness of the surface decreases, making it easier for asphalt mixtures to adhere. Therefore, from the perspective of extending the lifespan of construction machinery, a higher-performance anti-adhesion agent is required. Surfaces to which asphalt such as rubber tends to adhere easily are hydrophobic, and it is considered effective to adsorb a hydrophobic surfactant. Examples of hydrophobic surfactants include surfactants with a large number of carbon atoms and a large content of PO (oxypropylene group). However, hydrophobic surfactants have a high affinity for asphalt and tend to dissolve asphalt. When the surfactant dissolves asphalt, there is a concern that the aesthetic appearance of the pavement surface will deteriorate. Furthermore, hydrophobic surfactants have a low solubility in solvents such as water, and there is also a problem of deteriorating solution stability. In the prior art, it has been extremely difficult to provide an anti-adhesion agent that can suppress the adhesion of asphalt mixtures to rollers, etc. at a high level, while not dissolving the asphalt itself and having excellent stability during water dilution, and can also exhibit excellent effects on tire rollers to which asphalt easily adheres.

Means for Solving the Problem

[0007] The present invention relates to an anti-adhesion agent for asphalt composite materials that can suppress the adhesion of asphalt mixtures to rollers, etc. at a high level, while not dissolving the asphalt itself and having excellent stability during water dilution.

[0008] The present invention relates to the following [1]. [1] An anti-adhesion agent for asphalt composite materials containing a compound (A) represented by the following formula (1). R 1 O-(EO) m (PO)n -H ···(1) [In the formula, R 1 The O- group is a group obtained by removing a hydrogen atom from the hydroxy group of a linear secondary alcohol having 8 to 16 carbon atoms, EO is an oxyethylene group and PO is an oxypropylene group, m is the average number of moles of added oxyethylene groups, n is the average number of moles of added oxypropylene groups, and 4 ≤ m ≤ 20, 0 ≤ n ≤ 20, 4 ≤ m + n ≤ 30.] [Advantages of the Invention]

[0009] According to the present invention, it is possible to provide an asphalt composite adhesion inhibitor that highly suppresses the adhesion of an asphalt mixture to a roller or the like, while not dissolving the asphalt itself and having excellent stability during water dilution. [Embodiments for Carrying Out the Invention]

[0010] [Asphalt Composite Adhesion Inhibitor] The asphalt composite adhesion inhibitor of the present invention contains a compound (A) represented by the following formula (1). R 1 O-(EO) m (PO) n -H ···(1) [In the formula, R 1 The O- group is a group obtained by removing a hydrogen atom from the hydroxy group of a linear secondary alcohol having 8 to 16 carbon atoms, EO is an oxyethylene group and PO is an oxypropylene group, m is the average number of moles of added oxyethylene groups, n is the average number of moles of added oxypropylene groups, and 4 ≤ m ≤ 20, 0 ≤ n ≤ 20, 4 ≤ m + n ≤ 30.]

[0011] The compound (A) represented by the formula (1) according to the present invention has a structure derived from a secondary alcohol, and has a molecular structure in which the hydrophilic chain and the hydrophobic chain are nearly orthogonal compared to the conventional surfactant derived from a primary alcohol. Therefore, since the entire hydrophobic chain can interact with the surface that prevents the adhesion of asphalt materials such as rubber, the solid-liquid interface (rubber-water interface) is stabilized, and it is presumed that a uniform and highly retentive water film can be formed on the surface. As a result, it is considered that an excellent effect of preventing the adhesion of the binder can be exhibited even for a rubber roller or the like. In addition, although the detailed mechanism is unknown, if the compound (A) represented by the formula (1) has a predetermined number of carbon atoms, it is possible to simultaneously achieve the property of not dissolving asphalt and excellent stability in an aqueous solution. As a result, it is possible to provide an anti-asphalt binder adhesion inhibitor that can suppress the adhesion of high asphalt while not dissolving asphalt and forming a uniform solution when diluted with a solvent.

[0012] <Compound (A)> Compound (A) is a polyoxyalkylene monoalkyl ether compound represented by the above formula (1). R 1 The O-group is a group obtained by removing a hydrogen atom from the hydroxy group of a straight-chain secondary alcohol having 8 to 16 carbon atoms. That is, compound (A) is a compound in which a hydrogen element is substituted with a hydroxy group at a carbon atom other than the terminal in a straight-chain alkane represented by R 1 H. R 1 From the viewpoint of the effects of the present invention, the number of carbon atoms of the straight-chain secondary alcohol represented by R

[0013] R 1 OH is preferably 10 or more, more preferably 11 or more, and preferably 16 or less, more preferably 15 or less.

[0014]

Chemical formula

[0015] [In the formula, R1a is a linear alkyl group with a carbon number of a 1 , and R 1b is a linear alkyl group with a carbon number of b 1 , and 8 ≤ a 1 + b 1 + 1 ≤ 16.] R 1a has a carbon number of a 1 and R 1b has a carbon number of b 1 are each an integer of 1 or more and 14 or less. Examples of the linear alkyl group represented by R 1a and R 1b include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-dodecyl group, a tridecyl group, and a tetradecyl group. Examples of the linear and secondary alcohol represented by R 1 OH include, for example, 2-undecanol, 3-undecanol, 4-undecanol, 5-undecanol, 6-undecanol, 2-dodecanol, 3-dodecanol, 4-dodecanol, 5-dodecanol, 6-dodecanol, 2-tridecanol, 3-tridecanol, 4-tridecanol, 5-tridecanol, 6-tridecanol, 7-tridecanol, 2-tetradecanol, 3-tetradecanol, 4-tetradecanol, 5-tetradecanol, 6-tetradecanol, 7-tetradecanol, 2-pentadecanol, 3-pentadecanol, 4-pentadecanol, 5-pentadecanol, 6-pentadecanol, 7-pentadecanol, 8-pentadecanol, and the like.

[0016] EO is an oxyethylene group (-C 2 H 4 O-), and PO is an oxypropylene group (-C 3 H 6 O-). m represents the average number of moles of added oxyethylene groups, and n represents the average number of moles of added oxypropylene groups, respectively. m is 4 ≤ m ≤ 20, that is, 4 or more and 20 or less. From the viewpoint of stability upon dilution with water, it is preferably 6 or more, more preferably 8 or more, and is preferably 20 or less, more preferably 16 or less, still more preferably 12 or less. n is 0 ≤ n ≤ 20, that is, 0 or more and 20 or less. From the same viewpoint, it is preferably 0 or more, and is preferably 8 or less, more preferably 6 or less. m + n is 4 ≤ m + n ≤ 30, that is, 4 or more and 30 or less. From the same viewpoint, it is preferably 6 or more, more preferably 8 or more, and is preferably 20 or less, more preferably 15 or less.

[0017] The sequence order of EO and PO in the above formula (1) is not particularly limited and may be block-like or random-like, and is preferably block-like.

[0018] In a preferred embodiment of the present invention, from the viewpoint of the stability of the aqueous solution, 6 ≤ m ≤ 12 and 0.7 ≤ m / (m + n) ≤ 1. m / (m + n) is preferably 0.7 ≤ m / (m + n) ≤ 1, that is, 0.7 or more and 1 or less, and more preferably 0.75 or more. m / (m + n) indicates the ratio of the PO content to the total content of EO and PO.

[0019] The compound (A) represented by the above formula (1) can be produced by a known method. For example, it can be obtained by subjecting a linear and secondary alcohol having 8 to 16 carbon atoms to addition polymerization of ethylene oxide and propylene oxide. The addition polymerization of ethylene oxide and propylene oxide may be either random polymerization or block polymerization. Also, the average number of added moles of each of the oxyethylene group (EO) and the oxypropylene group (PO), and the ratio of the PO content to the total content of EO and PO can be adjusted by adjusting the respective usage amounts of ethylene oxide and propylene oxide.

[0020] As the compound (A) represented by the above formula (1), commercially available products can be used. Examples of such commercially available products include Emulgen 709 (manufactured by Kao Corporation), Softanol EP12030 (manufactured by Nippon Shokubai Co., Ltd.), and the like.

[0021] <Compound (B)> The asphalt composite adhesion inhibitor of the present invention preferably further contains a compound (B) represented by the following formula (2). R 2 O-(EO) k (PO) l -H ···(2) [In the formula, R 2 The O- group is a group obtained by removing a hydrogen atom from the hydroxy group of a branched and primary alcohol having 6 to 10 carbon atoms, EO is an oxyethylene group, and PO is an oxypropylene group, k is the average number of moles of added oxyethylene groups, l is the average number of moles of added oxypropylene groups, 2 ≦ k ≦ 10, and 0.75 ≦ k / (k + l) ≦ 1.]

[0022] Compound (B) is a polyoxyalkylene monoalkyl ether compound represented by the above formula (2). R 2 The O- group is a group obtained by removing a hydrogen atom from the hydroxy group of a branched or straight-chain and primary alcohol having 6 to 10 carbon atoms. That is, compound (B) is a compound in which a hydrogen element is substituted with a hydroxy group at the terminal carbon atom in a branched alkane represented by R 2 H. R 2 The number of carbon atoms of the branched and primary alcohol represented by R

[0023] R 2 OH is preferably 6 or more, more preferably 8 or more, and preferably 10 or less, more preferably 8 or less, from the viewpoint of the stability of the aqueous solution.

[0024]

Chemical formula

[0025] [In the formula, R 2a is a linear alkyl group having a carbon number of a 2 , R 2b is a linear alkyl group having a carbon number of b 2 , R 2c is a linear alkylene group having a carbon number of c 2 , and 6 ≤ a 2 + b 2 + c 2 + 1 ≤ 10.]

[0026] The carbon number a 2a of R 2 , the carbon number b 2b of R 2 , and the carbon number c 2c of R 1 are each an integer of 1 or more and 7 or less. Examples of the linear alkyl group represented by R 2a and R 2b include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, and an n-heptyl group. Examples of the linear alkylene group represented by R 2c include a group obtained by removing a hydrogen atom from the terminal carbon atom of the above linear alkyl group. Examples of the branched primary alcohol represented by R 2 OH include, for example, 2-ethylhexanol, 3-ethylhexanol, and the like.

[0027] EO is an oxyethylene group (-C 2 H 4 O-), and PO is an oxypropylene group (-C 3 H 6 O-). k represents the average number of moles of added oxyethylene groups, and l represents the average number of moles of added oxypropylene groups, respectively. k is 2 ≤ k ≤ 10, that is, 2 or more and 10 or less. From the viewpoint of stability during water dilution, it is preferably 2 or more, more preferably 4 or more, and preferably 8 or less, more preferably 6 or less. From the same perspective, l is preferably 0 ≤ l ≤ 5, that is, l is 0 or more and 5 or less, more preferably 0 or more, and even more preferably 4 or less, still more preferably 3 or less. From the same perspective, k + l is preferably 2 ≤ k + l ≤ 10, that is, k + l is 2 or more and 10 or less, more preferably 2 or more, even more preferably 4 or more, and even more preferably 8 or less, still more preferably 6 or less. From the same perspective, k / (k + l) is preferably 0.75 ≤ k / (k + l) ≤ 1, that is, k / (k + l) is 0.75 or more and 1 or less, more preferably 0.85 or more, even more preferably 1. ≤ k / (k + l) represents the ratio of the content of PO to the total content of EO and PO in the above formula (2).

[0028] The sequence order of EO and PO in the above formula (2) is not particularly limited and may be block-like or random-like, preferably block-like.

[0029] The compound (B) represented by the above formula (2) can be produced by a known method. For example, it can be obtained by addition polymerization of ethylene oxide and propylene oxide to a branched primary alcohol having 6 to 10 carbon atoms. The addition polymerization of ethylene oxide and propylene oxide may be either random polymerization or block polymerization. Also, the average number of moles of addition of each of the oxyethylene group (EO) and the oxypropylene group (PO), and the ratio of the content of PO to the total content of EO and PO can be adjusted by adjusting the respective usage amounts of ethylene oxide and propylene oxide.

[0030] Commercially available products can be used as the compound (B) represented by the above formula (2). Examples of such commercially available products include Braunon EH-4 (manufactured by Aoki Yushi Kogyo Co., Ltd.), Newcol 1004 (manufactured by Nippon Emulsifier Co., Ltd.), and the like.

[0031] When the asphalt composite adhesion inhibitor of the present invention contains the above compound (A) and compound (B), the mass ratio [(A):(B)] is preferably 80:20 to 30:70, more preferably 60:40 to 40:60.

[0032] The asphalt composite adhesion inhibitor of the present invention is used for the purpose of preventing the adhesion of asphalt composites to factory facilities and equipment in contact with asphalt composites, or for the purpose of peeling off the adhered asphalt composites. Asphalt composites (also referred to as asphalt mixtures) are mixed materials obtained by mixing aggregates (such as gravel, sand, and partially melted slag) and fillers with asphalt as a binder, and are used for paving roads and the like. The type of asphalt constituting the asphalt composite is not limited. For example, it is straight asphalt or modified asphalt. As one aspect of modified asphalt, asphalt modified with a thermoplastic elastomer can be mentioned. As another aspect, asphalt modified with a polyester can be mentioned. Such modified asphalt is also called polymer-modified asphalt. The asphalt composite adhesion inhibitor of the present invention exhibits an excellent anti-adhesion effect even when the asphalt is polymer-modified asphalt.

[0033] The asphalt composite adhesion inhibitor of the present invention is usually diluted with a solvent such as water before use. The dilution ratio is 3 to 100 times by mass, preferably 5 to 50 times by mass with water based on the total mass of the above compound (A) and the above compound (B). However, the asphalt composite adhesion inhibitor of the present invention may be used alone with the above compound (A) or a mixture of the above compound (A) and the above compound (B).

[0034] The asphalt mixture adhesion inhibitor of the present invention is mainly used in aggregate factory facilities such as hoppers and skip elevators, but may also be used on the beds of dump trucks used for transportation, finishers, macadam rollers, tire rollers, etc., which are paving equipment. The asphalt mixture adhesion inhibitor of the present invention may be applied using a brush or the like, or may be used by spraying with a spray or the like. The asphalt mixture adhesion inhibitor of the present invention is preferably for tire rollers. The tire roller is preferably made of rubber.

[0035] The asphalt mixture adhesion inhibitor of the present invention may be used in combination with additives within a range that does not inhibit the effects of the present invention. Examples of such additives include organic or inorganic salts, pH adjusters, bactericides, chelating agents, dyes, fragrances, and the like. The content of the additive in the asphalt mixture adhesion inhibitor is preferably 0.1% by mass or more, more preferably 1% by mass or more, and 20% by mass or less, more preferably 10% by mass or less.

[0036] The present invention also provides a method for constructing a road pavement, which includes a step of compacting using a tire roller coated with the above asphalt mixture adhesion inhibitor in a process of constructing an asphalt mixture on a road or the like to form an asphalt pavement layer.

Examples

[0037] Hereinafter, the present invention will be specifically described by way of examples, but the present invention is not limited by these examples.

[0038] Example 1 Using Compound A1 (trade name: Emulgen 709, manufactured by Kao Corporation) as Compound (A), the following Tests 1 to 3 were carried out. <Test 1: Stability evaluation test of aqueous solution> Weighed 2 g of Compound A1 into a plastic cup with a capacity of 200 mL and diluted it with tap water to make a total of 100 g of an aqueous solution. After that, the glass rod was used to stir well for about one minute, and the state of the aqueous solution was observed visually. The stability of the aqueous solution was evaluated according to the following evaluation criteria. The results are shown in Table 1. Non-uniform: The aqueous solution is turbid. Uniform: The aqueous solution is transparent and uniform without turbidity.

[0039] <Test 2: Evaluation Test of Asphalt Adhesion Prevention Effect> The aqueous solution prepared in the same manner as in Test 1 above was allowed to stand at room temperature for 6 hours. Next, a rubber piece at room temperature (width 2 cm × height 5 cm × thickness 1.5 mm) was immersed in the aqueous solution up to a height of 4 cm, then pulled up in the air to form a uniform water film on the surface of the rubber piece. In the case where separation occurred during the standing period, the rubber piece was immersed in the separated state without re-stirring. After that, the rubber piece with the water film formed was immersed in the polymer-modified asphalt type II (manufactured by Toa Road Industry Co., Ltd.) heated to 180 °C in an oven up to a height of 2 cm for 1 second, and then pulled up in the air. The amount of asphalt adhering to the rubber piece was measured at that time. The results are shown in Table 1. The rubber piece mimics a rubber roller, indicating that the smaller the amount of asphalt adhering to the rubber piece, the better the performance as an adhesion preventive agent.

[0040] <Test 3: Evaluation Test of Asphalt Solubility> 0.1 g of polymer-modified asphalt type II and 5 g of compound A1 were weighed into a screw tube and allowed to stand for 6 hours in a state where the asphalt was completely immersed in compound A1 (mixed liquid). Note that compound A1 is a liquid. After 6 hours, the color of the fraction of compound A1 in the obtained mixed liquid was observed visually, and the solubility of asphalt in compound A1 was evaluated according to the following criteria. The results are shown in Table 1. A: The fraction of compound A1 is colorless. B: A small amount of asphalt oozes out in the fraction of compound A1, and the fraction of compound A1 is light yellow (coloration is visible) to less than brown. C: A considerable amount of asphalt oozes out in the fraction corresponding to compound A1, and the fraction of compound A1 is brown to black.

[0041] Example 2 In Example 1, during Tests 2 and 3, polymer-modified asphalt type II (manufactured by Toa Road Industry Co., Ltd.) was changed to straight asphalt 60 / 80 (manufactured by Mitsubishi Corporation Energy Co., Ltd.), and during Test 2, the heating temperature of straight asphalt 60 / 80 was changed to 150°C. Tests 2 and 3 were conducted in the same manner as in Example 1 except for the above changes. Test 1 is the same as in Example 1. The results are shown in Table 1.

[0042] Example 3 In Example 1, during Tests 1 and 2, 2 g of Compound A1 was changed to 1 g of Compound A1, and Tests 1 and 2 were conducted. The results are shown in Table 1. Test 3 is the same as in Example 1.

[0043] Example 4 In Example 3, during Test 2, polymer-modified asphalt type II (manufactured by Toa Road Industry Co., Ltd.) was changed to straight asphalt 60 / 80 (manufactured by Mitsubishi Corporation Energy Co., Ltd.), and the heating temperature of straight asphalt 60 / 80 was changed to 150°C. Test 2 was conducted in the same manner as in Example 3 except for the above changes. The results are shown in Table 1. Test 1 is the same as in Example 1. Test 3 is the same as in Example 2.

[0044] Example 5 In Example 1, Compound A1 was changed to Compound A2 and each test was conducted. The results are shown in Table 1.

[0045] Example 6 In Example 1, during Tests 1 and 2, 2 g of Compound A1 was changed to a mixture of 1 g of Compound A2 and 1 g of Compound B1. Also, during Test 3, 5 g of Compound A1 was changed to a combination of 2.5 g of Compound A2 and 2.5 g of Compound B1. Each test was conducted in the same manner as in Example 1 except for the above changes. The results are shown in Table 1.

[0046] Example 7 In Example 6, during Tests 2 and 3, Polymer-Modified Asphalt Type II (manufactured by Toa Road Industry Co., Ltd.) was changed to Straight Asphalt 60 / 80, and Tests 2 and 3 were carried out. Test 1 is the same as in Example 6. The results are shown in Table 1.

[0047] Example 8 In Example 2, Compound A1 was changed to Compound A3 and each test was carried out. The results are shown in Table 1.

[0048] Comparative Example 1 In Example 1, Compound A1 was changed to Compound a1 and each test was carried out. The results are shown in Table 1.

[0049] Comparative Example 2 In Example 1, during Tests 1 and 2, 2 g of Compound A1 was changed to a mixture of 1.25 g of Compound a2 and 0.75 g of Compound b1. Also, during Test 3, 5 g of Compound A1 was changed to a combination of 3.125 g of Compound a2 and 1.875 g of Compound b1. Except for the above changes, each test was carried out in the same manner as in Example 1. The results are shown in Table 1.

[0050] Comparative Example 3 In Example 1, Compound A1 was changed to Compound B1 and each test was carried out. The results are shown in Table 1.

[0051] Comparative Example 4 In Example 1, during Tests 1 and 2, 2 g of Compound A1 was changed to a mixture of 1.20 g of Compound a3 and 0.80 g of Compound b2. Also, during Test 3, 5 g of Compound A1 was changed to a combination of 3 g of Compound a3 and 2 g of Compound b2. Except for the above changes, each test was carried out in the same manner as in Example 1. The results are shown in Table 1.

[0052] Comparative Example 5 In Test 2 of Example 1, the aqueous solution of Compound A1 was changed to ion-exchanged water, and Test 2 was carried out. Tests 1 and 3 were not carried out. The results are shown in Table 1.

[0053] The compounds used in Examples 1 to 8 and Comparative Examples 1 to 4 are as follows. <Compound (A), etc.> Compound A1: sec-C11~C15-O(EO) 9 -H [in formula (1), R 1 ; having 11 to 15 carbon atoms, m = 9, n = 0], Emulgen 709 (trade name), manufactured by Kao Corporation Compound A2: sec-C12~14-O(EO) 12 (PO) 3 -H [in formula (1), R 1 ; having 12 to 14 carbon atoms, m = 12, n = 3], Softanol EP12030 (trade name), manufactured by Nippon Shokubai Co., Ltd. Compound A3: sec-C12~C14-O(EO) 20 -H [in formula (1), R 1 ; having 12 to 14 carbon atoms, m = 20, n = 0], Softanol 200 (trade name), manufactured by Nippon Shokubai Co., Ltd. Compound a1: poly(ethylene glycol)-block-poly(propylene glycol)-block-poly(ethylene glycol), PEG weight ratio 30% by mass, manufactured by Sigma-Aldrich Compound a2: C13-O(EO) 28 (PO) 18 -H, polyoxyethylene(28) polyoxypropylene(18) tridecyl ether Compound a3: C12-O(EO) 6 -H, polyoxyethylene(6) lauryl ether, manufactured by Kao Corporation <Compound (B), etc.> Compound B1: 2-ethylhexyl (C8)-O(EO) 4 -H [in formula (2), R 2; Carbon number 8, k = 4, l = 0, k / (k + l) = 1], Newcol 1004 (trade name), manufactured by Nippon Emulsion Co., Ltd. Compound b1: C3 - O(EO) 5 (PO) 1 -H Compound b2: Diethylene glycol monobutyl ether, manufactured by Tokyo Chemical Industry Co., Ltd.

[0054]

Table 1

[0055] From the results in Table 1, it can be seen that the anti - adhesion agent containing the compound (A) of the present invention can suppress the adhesion of the asphalt mixture to a rubber roller or the like at a high level. Also, since it does not dissolve the asphalt itself, it does not adversely affect the durability and surface appearance of the pavement, and it is also suggested that it is an anti - adhesion agent with excellent stability when diluted with water. In addition, when using polymer - modified asphalt, which has a higher adhesion force to a roller or the like than straight asphalt, the amount of asphalt adhesion can be minimized, and it is expected to provide an excellent anti - adhesion effect.

Claims

**Claim 1** An anti-asphalt composite adhesion agent containing a compound (A) represented by the following formula (1). R １ O-(EO) ｍ (PO) ｎ -H...(1) [wherein, R １ The O-group is a group obtained by removing a hydrogen atom from a hydroxy group of a linear secondary alcohol having 8 to 16 carbon atoms, EO is an oxyethylene group, PO is an oxypropylene group, m is the average number of moles of added oxyethylene groups, n is the average number of moles of added oxypropylene groups, 4 ≤ m ≤ 20, 0 ≤ n ≤ 20, 4 ≤ m + n ≤ 30.]] **Claim 2** The anti-asphalt composite adhesion agent according to Claim 1, further containing a compound (B) represented by the following formula (2). R ２ O-(EO) ｋ (PO) ｌ -H...(2) [wherein, R ２ O-group is a group obtained by removing a hydrogen atom from a hydroxy group of a branched and primary alcohol having 6 to 10 carbon atoms, EO is an oxyethylene group, PO is an oxypropylene group, k is the average number of moles of added oxyethylene groups, l is the average number of moles of added oxypropylene groups, 2 ≤ k ≤ 10, and 0.75 ≤ k / (k + l) ≤ 1.]] **Claim 3** The anti-asphalt composite adhesion agent according to Claim 2, wherein the mass ratio [(A):(B)] of the compound (A) to the compound (B) is 80:20 to 30:

70. **Claim 4** The anti-asphalt composite adhesion agent according to any one of Claims 1 to 3, wherein in formula (1), 6 ≤ m ≤ 12 and 0.7 ≤ m / (m + n) ≤ 1. **Claim 5** The anti-asphalt composite adhesion agent according to any one of Claims 1 to 4, which is for a tire roller.

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