JP4959652B2 - Hydrocarbon solvent composition - Google Patents

Description

  The present invention relates to a hydrocarbon-based solvent composition. Specifically, the present invention relates to a hydrocarbon solvent composition that includes a high-boiling aromatic hydrocarbon and is excellent in safety.

In general, hydrocarbon solvents are used as components of ink compositions, coating compositions, resin compositions, and as various solvents or diluents.
These hydrocarbon solvents are expected to have higher safety, and are considered to affect the human body such as naphthalene and phenanthrene in consideration of handling in the production process and use by spraying or spraying to the natural world. It is desirable to be a hydrocarbon solvent that is substantially free of aromatic hydrocarbons, has low volatility, has low odor, and has a low environmental impact.

  Examples of highly safe solvents include hydrocarbon solvents having a high boiling point. High-boiling hydrocarbon solvents can be used for recording materials that obtain copy records by applying pressure, that is, pressure-sensitive copying materials, and pesticide compositions in the fields of agricultural chemicals, ant protection, antiseptics and weeding. Is known (see Patent Documents 1 and 2).

  Hydrocarbon solvents are used together with color formers in the field of pressure-sensitive paper or drug substances in the field of pest control agents, but conventional solvents have a low solubility and are difficult to have an aromatic odor. is there. In Patent Document 2, an aromatic odor is suppressed by adding a fragrance, but it is not a radical odor solution.

As a method for reducing the odor of the hydrocarbon solvent, hydrorefining, clay treatment, acid-alkali treatment, and the like may be performed when the odor is caused by impurities such as olefins and oxidative degradation products. However, removal of odors peculiar to aromatics is difficult even with these methods. In addition, high boiling point hydrocarbons have a problem of high viscosity and are difficult to use as a solvent.
JP 09-157189 A JP-A-10-130620

  An object of the present invention is to provide a low-viscosity hydrocarbon-based solvent having high dissolving power, excellent safety, low aromatic odor, high boiling point, and suitable as a solvent.

  As a result of intensive studies in view of such a situation, the present inventors have found that a high-boiling hydrocarbon-based composition containing an aromatic compound having a specific molecular weight can solve the above-mentioned problems, thereby completing the present invention. It came.

That is, the hydrocarbon solvent composition of the present invention is a solvent composition containing 90% by mass or more of an aromatic compound,
The content of a compound having a molecular weight of 224 having an aryl group is 5% by mass or more, the content of a compound having a molecular weight of 210 having an aryl group is 35% by mass or less, and the content of an alkylnaphthalene is 50% by mass or less. Yes.

Such a hydrocarbon-based solvent composition of the present invention has a 10% distillation temperature of 285 ° C or higher,
The 90% distillation temperature is preferably 320 ° C. or lower.
The hydrocarbon solvent composition of the present invention preferably has a phenanthrene content of 1.0% by mass or less and a naphthalene content of 0.1% by mass or less.

  The hydrocarbon solvent composition of the present invention preferably has a mixed aniline point of 14 ° C. or lower.

  According to the present invention, the content of aromatic compounds, such as naphthalene and phenanthrene, which are concerned about the influence on the human body is low, the safety is low, the volatility is low, the odor is low, the load on the environment is small, and the viscosity is low. Therefore, it is possible to provide a hydrocarbon solvent composition that is low in color, little colored, and excellent in solubility. The hydrocarbon solvent composition of the present invention can be widely used in various fields such as agricultural chemicals, pressure-sensitive adhesives, adhesives, inks, paints, dyes for pressure-sensitive copying materials, reaction solvents, rubbers, cleaning agents, and resins.

Hereinafter, the present invention will be specifically described.
The hydrocarbon solvent composition of the present invention is a solvent composition mainly composed of an aromatic hydrocarbon containing 90% by mass or more, preferably 95% by mass or more, more preferably 97% by mass or more of an aromatic compound. The content of the compound having a molecular weight of 224 having an aryl group is 5% by mass or more, the content of the compound having a molecular weight of 210 having an aryl group is 35% by mass or less, and the content of the alkylnaphthalene is 50% by mass or less.

  As the aryl group, a phenyl group, a benzyl group, a tolyl group, a xylyl group and the like are preferable. As the compound having a molecular weight of 224 having an aryl group (M224) and the compound having a molecular weight of 210 having an aryl group (M210), a compound having two benzene rings is preferable. Specifically, as the compound having a molecular weight of 224 having an aryl group (M224), alkylbiphenyls and alkyldiphenylalkanes having a total of 5 carbon atoms other than those constituting an aromatic ring are preferable. As the compound (M210) having a molecular weight of 210, alkylbiphenyls and alkyldiphenylalkanes having a total of 4 carbon atoms other than those constituting an aromatic ring are preferable. Alkylnaphthalene is a compound in which one or more hydrogen elements of naphthalene are substituted with an alkyl group.

  In the hydrocarbon solvent composition of the present invention, the content of the aryl group-containing compound having a molecular weight of 224 (M224) is 5% by mass or more, preferably 10-60% by mass, more preferably 25-50% by mass. In addition, the content of the compound having a molecular weight of 210 (M210) having an aryl group is 35% by mass or less, preferably 33% by mass or less. Furthermore, the content of alkylnaphthalene is 50% by mass or less, preferably 35% by mass or less. When M224 is less than 5% by mass, when the content of M210 exceeds 35% by mass, and when the alkylnaphthalene exceeds 50% by mass, the aromatic odor or unpleasant odor becomes strong.

  Increasing the content of high-molecular-weight or high-boiling aromatic compounds is undesirable because the kinematic viscosity of the solvent increases or the mixed aniline point increases and the solubility decreases, increasing the amount of low-molecular-weight or low-boiling aromatic compounds. This is not preferable because the odor increases. Therefore, it is desirable that the total amount of M224 and M210 is 40 to 80% by mass or more, more preferably 50 to 75% by mass.

The molecular weight can be measured with a gas chromatograph mass spectrometer (GC / MS), and the content can be measured with an FID detector.
The hydrocarbon solvent composition of the present invention has a 10% distillation temperature in distillation properties of 285 ° C. or higher,
The temperature is preferably 290 ° C. or higher, and the 90% distillation temperature is 320 ° C. or lower, preferably 90% distillation temperature is 315 ° C. or lower. If the 10% distillation temperature is less than 285 ° C., the odor of the aromatic odor becomes strong, which is not preferable. In addition, when the 90% distillation temperature exceeds 320 ° C., the kinematic viscosity of the solvent is high, the solubility is lowered and the use as a solvent may be limited, and the phenanthrene content is 1.0% by mass. Since it may exceed, it is not preferable. Since phenanthrene is regulated by the Law Concerning the Release of Specific Chemical Substances to the Environment and the Promotion of Improvements in Management (PRTR Law) for the purpose of preventing problems in environmental conservation, carbonization The content of phenanthrene in the hydrogen-based solvent composition is 1.0% by mass or less, more preferably 0.5% by mass or less, and particularly preferably 0.1% by mass or less. For this reason, it is more preferable that the hydrocarbon solvent composition of the present invention does not substantially contain a component having a boiling point of 330 ° C. or higher, and the distillation end point temperature is preferably 330 ° C. or lower, more preferably 325 ° C. or lower. Is desirable.

  In addition, it is not preferable that the hydrocarbon-based solvent composition contains naphthalene because the aromatic odor becomes strong and there is a concern about adverse effects on the human body. The hydrocarbon solvent composition of the present invention may be substantially free of naphthalene, but the content is preferably 0.1% by mass or less, more preferably 0.5% by mass or less, particularly 0.01%. It is desirable that it is less than mass%.

  For this reason, the hydrocarbon solvent composition of the present invention is more preferably substantially free of components having a boiling point of 230 ° C. or lower, and the initial distillation temperature is preferably 230 ° C. or higher, more preferably 250 ° C. or higher. Is desirable. Such a hydrocarbon-based solvent composition is preferable because it contains substantially no benzene, toluene, xylene, 1,3,5-trimethylbenzene, etc. in addition to naphthalene, and is therefore less susceptible to adverse effects on the human body. . The distillation property is a value measured by a method defined in JIS K2254.

  The sulfur content and the nitrogen content in the hydrocarbon solvent composition are preferably as low as possible from the viewpoint of reducing the load on the environment, and are 10 mass ppm or less, preferably 5 mass ppm or less, particularly 1 mass ppm or less. The sulfur content is a value measured according to the method specified in JIS K2541, and the nitrogen content is determined according to JIS K2609.

  The mixed aniline point of the hydrocarbon solvent composition is an indicator of solubility, and the lower the better, the better, but from the viewpoint of solubility, it is 14 ° C. or lower, preferably 13 ° C. or lower, more preferably 12 to 13 ° C. is there. The mixed aniline point is a value measured by a method defined in JIS K2256.

  The Saybolt color is not particularly limited, but is preferably +1 or more, more preferably +10 or more, and particularly +20 or more. In the case of use as a solvent, it is desirable because it is preferably near colorless and transparent. The Saebold color is a value measured by a method defined in JIS K2580.

  The flash point of the hydrocarbon solvent composition of the present invention is usually 130 ° C. or higher, preferably 140 ° C. or higher. A flash point of 130 ° C. or higher is preferred because of low volatility, low environmental burden, easy handling and high safety. The flash point is a value measured by a method defined in JIS K2265.

The kinematic viscosity depends on the use of the solvent composition, but is 5.0-13.0 mm ² / s at 30 ° C.
Hereinafter, it is preferably 6.0 to 12.0 mm ² / s or less. The kinematic viscosity is a value measured by a method defined in JIS K2283.

Examples of the raw material for the hydrocarbon solvent composition of the present invention include hydrocracking in petroleum refining,
A naphtha fraction distilled from a thermal cracking or catalytic cracking apparatus or a catalytic reforming fraction obtained by a catalytic reforming reaction using straight-run naphtha as a raw material can be used. Impurities such as sulfur and nitrogen in these raw materials are preferably removed in advance by performing a hydrogenation treatment with a pretreatment device. Among these raw materials, a catalytic reforming fraction obtained by a catalytic reforming reaction using naphtha as a raw material is particularly preferably used.

  The method for producing the hydrocarbon solvent composition of the present invention is not particularly limited, but the hydrocarbon solvent of the present invention is obtained by fractionating the above raw materials such as catalytic reforming fraction by precision distillation. A composition can be obtained easily. The hydrocarbon solvent composition of the present invention can also be produced by mixing two or more fractions obtained by fractional distillation of the above raw materials.

  In particular, a hydrocarbon solvent composition that can be used for various applications by cutting the raw material so that the 10% distillation temperature is 285 ° C or higher and the 90% distillation temperature is 320 ° C or lower. Is preferable.

  Such a hydrocarbon solvent composition of the present invention has low volatility, low odor, high safety to the human body, and excellent viscosity and solubility. The hydrocarbon solvent composition of the present invention has a high boiling point, high safety, and excellent solubility, so that it is a pressure-sensitive adhesive, adhesive, paint, ink, electrical insulating oil, pressure sensitive copying material dye, cleaning agent, It can be suitably used as a solvent for substances selected from the group consisting of agricultural chemicals, reaction solvents, synthetic resins, and rubbers.

EXAMPLES Hereinafter, although this invention is demonstrated further more concretely based on an Example, this invention is not limited to these Examples.
[Example 1]
The reformed fraction obtained by the catalytic reforming reaction of the naphtha fraction was fractionated into a fraction having a boiling point of 288.5 to 297.0 ° C. by precision distillation to obtain a hydrocarbon solvent composition. Table 1 shows the properties of the obtained hydrocarbon solvent composition.

The molecular weight was measured using a gas chromatograph mass spectrometer (GC / MS) (HP 5973N manufactured by Hewlett Packard, non-polar column, inlet temperature 290 ° C., initial column temperature 50 ° C. (retention time 5 minutes), temperature increase rate 2 The final column temperature was 300 ° C. (holding time: 10 minutes)), and the compound was confirmed from the obtained mass spectrum to measure the molecular weight. Moreover, the content was implemented using the gas chromatograph (FID detector). Evaluation tests other than the above were performed by the methods shown below.
・ Density: JIS K2249
Odor sensory test: In the odor sensory test, 50 ml of a sample was placed in a 100 ml glass container, and a sensory test was conducted at room temperature by four men and two women, and the following criteria were used.

A: Does not feel aromatic odor or irritation / unpleasant odor B: Slightly feels aromatic odor or irritation / unpleasant odor C: Strongly feels aromatic odor or irritation / unpleasant odor [Examples 2-6, Comparative Examples 1- 3]
In the distillation operation of Example 1, a fraction having a boiling point of 293.5 to 301.0 ° C. (Example 2), a fraction having a boiling point of 299.0 to 305.5 ° C. (Example 3), and a boiling point of 301.0 to 310 A fraction having a boiling point of 30 ° C. to 311.0 ° C. (Example 5), a fraction having a boiling point of 306.0 to 315.0 ° C. (Example 6), a boiling point of 257 A fraction having a boiling point of 275.0 to 282.0 ° C (Comparative Example 2) and a fraction having a boiling point of 282.5 to 290.0 ° C (Comparative Example 3) The properties were measured or evaluated in the same manner as in Example 1.

  The hydrocarbon solvent composition of the present invention is, for example, as a solvent in various fields such as pressure-sensitive adhesives, adhesives, paints, inks, electrical insulating oils, pressure-sensitive copying material dyes, cleaning agents, agricultural chemicals, reaction solvents, and synthetic resins. It can be used widely and suitably.

Claims (4)

A solvent composition containing 90% by mass or more of an aromatic compound,
The content of a compound having a molecular weight of 224 having an aryl group is 5% by mass or more, the content of a compound having a molecular weight of 210 having an aryl group is 35% by mass or less, and the content of an alkylnaphthalene is 50% by mass or less. A hydrocarbon solvent composition.   The hydrocarbon solvent composition according to claim 1, wherein the 10% distillation temperature is 285 ° C or higher and the 90% distillation temperature is 320 ° C or lower.   The hydrocarbon solvent composition according to claim 1 or 2, wherein the phenanthrene content is 1.0 mass% or less and the naphthalene content is 0.1 mass% or less.   The hydrocarbon solvent composition according to any one of claims 1 to 3, wherein the mixed aniline point is 14 ° C or lower.