Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From ketone or ketene reactant
Reexamination Certificate
2000-11-01
2003-12-23
Hampton-Hightower, P. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From ketone or ketene reactant
C528S339000, C528S339300, C564S511000, C564S512000, C106S246000, C106S269000, C106S277000
Reexamination Certificate
active
06667382
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a polyamine which is used in an asphalt emulsion, a catalyst for urethane, a chelating agent, a material for surfactants, a mining flotation agent, a material for fiber softeners and the like. The present invention also relates to an asphalt emulsion composition which is obtained by using the above-mentioned polyamine.
BACKGROUND ART
Heretofore, aliphatic amines, which have a straight-chain alkyl group having 12 to 22 carbon atoms, have been used in an emulsifier or the like for the production of an asphalt emulsion. However, since these amines are solids or pastes at normal temperature, the handling of these amines was not easy. Despite efforts, which have been made traditionally in order to liquefy these compounds, the following problems still remain.
For example, a significant sacrifice of surface activity is associated with the amines obtained by a process described in U.S. Pat. No. 2,930,701 comprising oxyalkylating an alkylamine or an alkylpropylenediamine, or by a process described in U.S. Pat No. 4,561,900 comprising methylating a secondary nitrogen. That is, when these amines are used, the adding amount thereof needs to be larger than that of the solid amine as a material thereof, or alternatively, when these amines are used for the production of an emulsion, a larger amount of mechanical energy is required.
Meanwhile, when a road is paved with an asphalt emulsion, in order to open the road after paving operation thereof quickly to traffic, a method such as slurry seal or micro-surfacing is adopted. In this method, an asphalt emulsion, aggregates and water are loaded in a vehicle by a special mechanism which prevents their mutual contact. The asphalt emulsion, aggregates and water are mixed by a mixer while the vehicle moves and the mixture is spread on a road. In this method, when the asphalt emulsion, aggregates and water be mixed, it is desired that the vehicle runs and puts (or moves) easily on the mixture. Namely, the asphalt emulsion, aggregates and water should be mixed well and the mixture needfully has a sufficient fluidity (being as “miscibility of aggregates”). Further when the mixture is spread on a road, the demulsification desirably takes place as soon as possible so that the mixture sets (being as “quick hardenability”). A mixture, which sets within one hour after the spreading thereof so that the pavement is open to traffic, is described as having a quick setting property. Since the setting time significantly varies depending on the types of aggregates and temperatures, it is desired that the setting rate be controllable so that the mixture can be used under various conditions.
In order to meet the above-mentioned points and required performances, a variety of emulsifiers for asphalt and cationic asphalt emulsion compositions have been proposed.
For example, CA-A 953452 discloses a cationic asphalt emulsion in which a quaternary ammonium salt is used as an emulsifier, and U.S. Pat. No. 5,242,492 describes a reaction product made from a fatty acid having 20 or more carbon atoms with a polyamine. However, none of these techniques satisfy the above-mentioned requirements.
Accordingly, one objective of the present invention is to provide an amine which has a surface activity not inferior to that of an amine based on a solid tallow and an excellent workability and which is suited for use in the emulsification of asphalt or the like. Another objective of the present invention is to provide an asphalt emulsion composition which is obtained by using the amine and which has a quick setting property.
DISCLOSURE OF INVENTION
The present inventors found that a specific polyamine is in a liquid state at normal temperature and the ability of the specific polyamine to emulsify asphalt is not reduced unlike the case of conventional liquid amines. In addition, they found that an asphalt emulsion composition containing a water-soluble salt of the specific polyamine has an excellent quick setting property; that is to say, the asphalt emulsion composition is excellent in the miscibility of aggregates; the setting time after paving operation can be controlled by the amounts added of fillers, such as cement, slaked lime and the like, and that of water; and the use of this emulsion composition makes it possible to open the road to traffic when one hour elapses after the paving operation under a wide range of conditions.
Accordingly, the present invention provides a polyamine represented by the formula (1) (hereinafter referred to as polyamine (1)), a process for producing the polyamine, use of an amine composed of the polyamine in an asphalt emulsion and an asphalt emulsion composition containing a salt of the amine preferably being water-soluble;
wherein R is a straight or branched hydrocarbon group having 8 to 22 carbon atoms; x is a number of 1 to 5; and each of y and z is a number of 0 to 5 with the proviso that both of y and z are not 0 at the same time, or a salt thereof.
The invention provides a salt of a polyamine for use in an asphalt emulsion, said amine being obtained by carrying out the cyanoethylation of a compound represented by the formula (2) by reacting 0.2 to 3 moles of acrylonitrile with 1 mole of the compound or carrying out the cyanoethylation of a compound represented by the formula (3) by reacting 1.4 to (m+2) moles of acrylonitrile with 1 mole of the compound; and hydrogenating the cyanoethylation product.
The invention provides an asphalt emulsion composition containing a salt of the polyamine as above described and then an asphalt emulsion comprising asphalt, water and a salt of the polyamine.
The invention provides a method of emulsifying asphalt with a salt of the polyamine. Asphalt may be emulsified with the polyamine and an acid, preferably the polyamine being used in an equivalent or more to the acid.
The invention provides use of a salt of the polyamine as an emulsifier for asphalt.
Modes for Carrying Out the Invention
In the polyamine (1) of the present invention, preferably R has 10 to 20 carbon atoms from the standpoint of emulsifiability and preferably R has 8 to 18 carbon atoms from the standpoint of being a liquid at normal temperature. From these standpoints, most preferably R has 10 to 18 carbon atoms. Besides, the hydrocarbon group may be made up of a mixture of hydrocarbon groups. X is preferably 1 to 2, and most preferably 1. The sum of y and z is preferably 1 to 4, and most preferably 1 to 3.
Examples of the polyamine (1) include the following compounds. Among them, from the standpoint of emulsifiability, preferable examples are (b), (c), (d), (h) and (i), and most preferable examples are (b), (c) and (d).
The polyamine (1) is obtained by carrying out the cyanoethylation of a compound represented by the formula (2) (hereinafter referred to as compound (2)) or a compound represented by the formula (3) (hereinafter referred to as compound (3)) by reacting acrylonitrile therewith and thereafter hydrogenating the cyanoethylation product;
wherein R is as defined above; and m is a number of 1 to 3.
Specific examples of the compound (2) include N-myristyl-N-aminopropylpropylenediamine, N-stearyl-N-aminopropylpropylenediamine, N-tallow alkyl-N-aminopropylpropylenediamine and the like.
In the compound (3), m is 1 to 3 and is preferably 1 to 2 from the standpoint of emulsifiability. Besides, the group having m may be made up of a mixture of groups. Specific examples of the compound (3) include myristylpropylenediamine, stearylpropylenediamine, tallow alkylpropylenediamine, palm kernel oil alkylpropylenediamine, tallow alkyldipropylenetriamine, tallow alkyltripropylenetetramine and the like.
When the compound (2) is reacted with acrylonitrile, it is preferable that 0.2 to 3 moles of acrylonitrile be reacted per mole of the compound (2). Meanwhile, when the compound (3) is reacted with acrylonitrile, it is preferable that 1.4 to (m+3) moles of acrylonitrile be reacted per mole of the compound (3).
In the hydrogenating reaction of cyanoethylation product, the reaction temperature is
Fukushima Tetsuaki
Isobe Kazuo
Nishimoto Uichiro
Tamaki Ryoichi
Tomioka Keiichiro
Hampton-Hightower P.
Kao Corporation
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