JPS608855B2 - dispersant - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a dispersant for dispersing fine solid particles in a non-aqueous solvent.

More specifically, a group represented by the general formula or [wherein R is an alkyl group having 10 to 16 carbon atoms, R' is a methyl or ethyl group, and X is a halogen atom or a methyl sulfate or ethyl sulfate residue] The present invention relates to a dispersant for dispersing solid fine particles containing a quaternary ammonium salt as an essential component in a non-aqueous solvent.

The technology of dispersing and suspending solid particles in non-aqueous solvents has important significance in various industrial fields such as oil-based paints, oil-based inks, fuel oil additives, sludge dispersants for internal combustion engines and lubricating oils, and even flushing. .

Although many theoretical considerations have been made regarding dispersion, in reality, many types of surfactants and polymer compounds are used in combination based on experience and intuition in each technical field. The current situation is that For example, in the case of paints and inks, the formulation differs depending on the type, and the contents are usually kept secretly as part of each company's know-how. However, surfactants and polymer compounds that are generally considered to be effective are known, and in many cases, a synergistic effect is required by combining them. Therefore, there is a strong demand for a surfactant that has a higher dispersion effect than the surfactants that have been known to be effective. The present inventors investigated the dispersion effect of surfactants with various structures in non-aqueous soot, and found that at least secondary alkyl groups, which had not been known about their dispersion effect in non-aqueous solvents, It was discovered that one quaternary ammonium salt has an extremely excellent dispersion performance.

Typical examples of dispersants effective in non-aqueous solvents include petroleum sulfonates, aliphatic amine salts, quaternary ammonium salts, sorbitan alkyl esters, and lecithin.

Of these, no quaternary ammonium salt having a secondary alkyl group bonded to a nitrogen atom is known at all.
The reason is that the secondary alkyl group has a quaternary alkyl group bonded to the nitrogen atom.
This is probably because the primary ammonium salt was not commercially available and it was not expected that the dispersion performance would be significantly different depending on the difference between the linear alkyl group and the secondary alkyl group. In the quaternary ammonium salt, which is effective in the present invention and has a secondary carbon of a secondary alkyl group bonded to a nitrogen atom, the secondary alkyl group has 10 carbon atoms.
-16 are particularly effective.

The position of the carbon to which the amino group is bonded is most preferably the second carbon from the viewpoint of industrial productivity. Other groups constituting the quaternary ammonium salt are composed of either an alkyl group, a hydroxyalkyl group, or a group in which two residues are combined with N to form a morpholine ring. The most preferred hydroxyalkyl group is a hydroxyethyl group. The anionic residue may be a halogen residue such as chlorine, bromine, or iodine, methyl sulfate, or the like. The quaternary alkyl ammonium salt containing a secondary alkyl group used in the present invention is prepared by converting a tertiary amine prepared by the method described in Japanese Patent Publication No. 51-20484 into a quaternary alkyl ammonium salt by a conventional method. It can be obtained by converting

That is, a long chain secondary alkyl group halide represented by the general formula: "R and R' have the same meanings as above and x represents a halogen atom" and an excess amount of the formula: or are reacted without a solvent to form an upper layer. A reaction product (tertiary amine) is obtained from the reaction mixture, and the obtained tertiary amine is converted into a quaternary ammonium salt by a conventional method.

Reference example 1 2-chlorohexadecane and 2-chlorooctadecane (1
50 parts by weight of jetanolamine were added to 250 parts by weight of the mixture) and vigorously heated at 16,000 for 3 hours.

After the reaction, the mixture was allowed to stand still and the upper layer was removed. The upper layer was N-(2-hexadecyl/octadecyl)diethanolamine. Obtained Amin 1
7.5 parts by weight was dissolved in benzene, 55 parts by weight of methyl bromide was added dropwise under reflux conditions, and after reacting for about 3 hours, the benzene was distilled off. The product was used as a dispersant [1] in Examples. Reference example 2 2-chlorododecane and 2-chlorotetradecane (1:1
A quaternary ammonium salt was obtained according to Reference Example 1 except that 200 parts by weight of the mixture was used.

This was used as a dispersant [D] in Examples. Dispersant [1
]: Fractional material [m [In the formula, R, 4 to 6 represent an alkyl group having 10 to 16 carbon atoms, and Rm to 2 represent an alkyl group having 10 to 12 carbon atoms.

The same applies below. Example 1 (Dispersion stability test of fuel oil additives) 5 parts by weight of various surfactants were dissolved in 45 parts by weight of kerosene, 5 parts by weight of magnesium hydroxide was added, and this was mixed in 3 parts with a homogenizer. worship the shrine.

The resulting homogeneous suspension (fuel oil additive) was placed in five cylinders with 100-liter stoppers and allowed to stand at room temperature for 50 days.
Measure the volume of the supernatant solution and precipitate every 10 days, and calculate the percentage of the sample volume.

Dispersant [1] and Dispersant [0] having the above-mentioned compositions were used in the test, and the following surfactant conventionally known as a dispersant for non-aqueous solvents was used as a comparison sample. Comparative sample petroleum sulfonate: petroleum sulfol R-20, R-
10 and Ca-45 (both manufactured by Matsumura Sekiyu Co., Ltd., trade names) Aliphatic amine salt A: [RNH2(CH2)3N ratio]2-[R'COO-]2
Aliphatic amine salt B: RCOONH3R' Quaternary ammonium salt C: [Ru2~14N(CH3)3]decaCr Quaternary ammonium salt D: [R,8N(Cmelon)3]decaCI-4th Class ammonium salt E: [(R,8)2N(CH3)2]10CI-Ampholytic surfactant: lecithin Nonionic surfactant: sorbitan monolaurate, sorbitan monooleate, sorbitan sesochyleate,
The sorbitan triolate test results are shown in Table-1.

Table 1 Example 2 Add 40 parts by weight of alkyd resin to 1 part by weight of carbon black to prepare a carbon black base.

Separately, dispersed soot is prepared by dissolving 2 parts by volume of a surfactant in a mixed solvent of 3 parts by volume of toluene and 2 parts by volume of kerosene. As the surfactant, the dispersant used in Example 1 [1], [0]
and the quaternary ammonium salt D which showed the best results in Comparative Example 1 are used as Comparative Example 2. Add 80 parts by volume of a dispersion medium to 2 parts by volume of the above paint base and thoroughly saturate. Put this in a centrifuge at 100 pm for 5 minutes,
Measure the amount of sediment. The results are shown in Table-2. Incidentally, the amount of precipitation is expressed in volume % of the precipitate relative to the total sample. Table 2 Example 3 1 part by weight of ammonium powder and 40 parts by weight of alkyd resin are mixed as uniformly as possible in a mineral spirit-butyl acetate mixture, and the total amount is brought to 100 parts by volume while kneading to prepare an aluminum paint base.

Separately, 2 parts by volume of a surfactant is dissolved in a solution of 2 parts by volume of toluene and 1 part by volume of kerosene to prepare dispersed soot. Dispersants [1] and [B] are used as surfactants, and quaternary ammonium salt D used in Comparative Example 2 is used as a comparative example. Uniformly disperse 6 parts of the aluminum paint base into 4 parts of the above dispersion medium, and place the mixture in a test tube. Measure the amount of precipitate and supernatant solution after 1 day and 2 days. The results are shown in Table-3.
The numerical values in the table are expressed in volume % of the precipitate or toplighting liquid relative to the sample amount. Table-3

Claims (1)

[Claims] 1 General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Or: ▲There are numerical formulas, chemical formulas, tables, etc.▼ [In the formula, R is an alkyl group having 10 to 16 carbon atoms, and R' is methyl or ethyl group, X represents a halogen atom or a methyl sulfate or ethyl sulfate residue]
A dispersant for dispersing fine solid particles containing grade ammonium salt as an essential component in a non-aqueous solvent.