JP2001072761A - Liquid composition containing alkylene oxide adduct of melamine or alkylene oxide adduct of melamine derivtive and production of the composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a liquid composition containing an allkylene oxide adduct of melamine or its derivative in a high yield at a low cost by subjecting an alkylene oxide to addition reaction with melamine or its derivative in the presence of an alkylene oxide adduct of phenol or benzyl alcohol. SOLUTION: This composition contains (A) an alkylene oxide adduct of melamine or its derivative and (B) an alkylene oxide adduct of phenol or benzyl alcohol. Preferably, 5 to 12 mol of an alkylene oxide is subjected to addition reaction with 1 mol of melamine or its derivative; and 1 to 5 mol of an alkylene oxide, with 1 mol of phenol or benzyl alcohol. Preferably, the wt. ratio of A/B is 0.1 to 5.0. The melamine derivative is preferably benzoguanamine, acetoguanamine or the like. Ethylene oxide and propylene oxide are preferable as the alkylene oxide.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a melamine-based alkylene oxide adduct which is particularly useful as a flame retardant for urethane.

[0002]

2. Description of the Related Art As a technique for adding an alkylene oxide to melamine, Japanese Patent Application Laid-Open Nos. Sho 42-15639 and
-198216, JP-A-10-251399, etc., all of which use a large amount of a solvent or use a basic catalyst, so that it is necessary to recover and remove the solvent, which increases the cost and increases the production process. Was also complicated and not a reasonable technology.

[0003]

DISCLOSURE OF THE INVENTION The present invention provides a high yield,
It is intended to provide an alkylene oxide adduct of melamine or a melamine derivative which can be produced at low cost, and a method for producing the same.

[0004]

That is, the present invention provides a liquid composition comprising the following (a) and (b). (A) An alkylene oxide adduct of melamine or an alkylene oxide adduct of a melamine derivative. (B) An alkylene oxide adduct of phenol or an alkylene oxide adduct of benzyl alcohol. Further, the present invention provides a method for producing the liquid composition, which comprises adding an alkylene oxide to melamine or a melamine derivative in the presence of an alkylene oxide adduct of phenol or an alkylene oxide adduct of benzyl alcohol.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION Melamine derivatives include all derived from melamine in chemical structure, but preferably include benzoguanamine, acetoguanamine and the like.
Examples of the alkylene oxide include ethylene oxide, propylene oxide, butylene oxide and the like, and preferably ethylene oxide and propylene oxide. The liquid composition of the present invention comprises (a) an alkylene oxide adduct of melamine or an alkylene oxide adduct of a melamine derivative, and (b) an alkylene oxide adduct of phenol or an alkylene oxide adduct of benzyl alcohol. Is 3 to 30 moles, preferably 5 to 5 moles per 1 mole of melamine or melamine derivative.
12 moles. The number of moles of the alkylene oxide added to the phenol or benzyl alcohol is preferably 1 to 5 mol, and more preferably 1 to 3 mol.
(A) / (b) is preferably 0.1 to 5.0 in weight ratio,
More preferably, it is 0.5 to 3.0. The composition of the present invention is liquid at normal temperature.

The method for producing the liquid composition of the present invention is described below. The production of the liquid composition of the present invention is characterized in that an alkylene oxide is added to melamine or a melamine derivative in the presence of an alkylene oxide adduct of phenol or an alkylene oxide adduct of benzyl alcohol as a solvent. As the alkylene oxide adduct of phenol or alkylene oxide adduct of benzyl alcohol, a low addition molar form of phenol or benzyl alcohol alkylene oxide is preferred. Examples thereof include phenoxyethanol, phenoxypropanol, a 1 mol adduct of benzyl alcohol with ethylene oxide, a 1 mol adduct of benzyl alcohol with propylene oxide, and more preferably phenoxyethanol and phenoxypropanol.

The (c) alkylene oxide adduct of phenol or the alkylene oxide adduct of benzyl alcohol is liquid at room temperature, and a powder of (d) melamine or a melamine derivative is dispersed in the liquid. Since this melamine-containing slurry has a high viscosity at room temperature, the liquid temperature is raised to 50 to 100 ° C., preferably 70 to 80 ° C., and then stirred to wet the melamine or a derivative thereof with the liquid, and Disperse. The weight ratio (c) / (d) is 0.2 to 2.0, preferably 0.5 to 1.2. Subsequently, an alkylene oxide is added at an addition temperature of 140 to 200 ° C, preferably 170 to 190 ° C.
It is. In the present invention, it is an advantage over the prior art that the reaction proceeds sufficiently without a catalyst.

The alkylene oxide includes ethylene oxide, propylene oxide, butylene oxide and the like, and is preferably ethylene oxide or propylene oxide. These may be any of single, block and random addition, but are preferably single or block addition. The number of moles to be added is 2 to 40 moles, preferably 3 to 30 moles per mole of melamine or a melamine derivative.

At the above reaction temperature, an addition reaction is carried out by a known method. After aging, the mixture is cooled to 100 ° C. or lower, and unreacted melamine or a derivative thereof is removed by filtration.
To obtain a liquid composition containing (b). In this reaction,
Alkylene oxide is a competitive addition reaction to (c) and (d) at the start of the reaction, but the reaction with (d) that has been liquefied gradually proceeds preferentially. The alkylene oxide adduct of (c) can be optionally separated by distillation or the like to increase the proportion in the composition of (d). For example, the liquid composition of the present invention may be used as a flame retardant for urethane. When used as (c), the alkylene oxide adduct of (c) exhibits an effect as a viscosity reducing agent, and further, in order to maintain the viscosity of the liquid composition at a relatively low viscosity which is easy to handle, the (c) It is important that an alkylene oxide adduct is contained in the liquid composition at a fixed ratio, and thus it is possible to produce the product as it is without performing a separation step such as a distillation operation.

[0010]

EXAMPLES Examples of the present invention will be described below, but the present invention is not limited to these examples. [Example 1] A melamine-containing slurry obtained by premixing 420 g of phenoxyethanol and 420 g of melamine at 70 ° C in a 4 L pressure-resistant reaction vessel, and after replacing with nitrogen 180 ±
The mixture is heated to 5 ° C., and 1935 g of propylene oxide (hereinafter abbreviated as PO) is added dropwise without a catalyst to cause an addition reaction.
The pressure of the system during the reaction is about 400 kPa (4 kgf / c
m ² ). After the reaction, the reaction mixture was aged until a certain pressure was reached, and after degassing and cooling, unreacted melamine was removed by pressure filtration to obtain a liquid composition. Example 2 A liquid composition was obtained in the same manner as in Example 1 except that the amount of PO was changed to 1161 g.

Example 3 Phenoxyethanol 210
g, melamine 210 g, and PO 2709 g, to obtain a liquid composition in the same manner as in Example 1. No unreacted melamine was found. Example 4 Instead of PO, ethylene oxide (hereinafter, referred to as “PO”)
A liquid composition was obtained in the same manner as in Example 1 except that EO was abbreviated to 880 g. Example 5 A liquid composition was obtained in the same manner as in Example 1 except that phenoxypropanol was used instead of phenoxyethanol. [Comparative Example 1] PO was replaced by polyethylene glycol (average molecular weight: 200) instead of phenoxyethanol.
A liquid composition was obtained in the same manner as in Example 1 except that the amount was 161 g.

The results are summarized in Table 1. The number of moles of alkylene oxide added is the number of alkylene oxides introduced into the reaction system in terms of 1 mole of melamine. For example, 10PO means 10 moles of propylene oxide. The pH is the value of an aqueous dispersion of 7.7% by weight of the product (according to JIS K1557). The amine value was measured by the acetic acid solvent method (this method can measure the total of primary amine to tertiary amine). The hydroxyl value was measured by a phthalation method (based on JIS K1557). The units of the amine value and the hydroxyl value are both mgKOH / g. The melamine conversion was calculated from the weight ratio of unreacted melamine after filtration to the charged amount. (A) / (b) is to dissolve the obtained liquid composition in a 20% aqueous solution of isopropanol, and then pass through a column filled with an ion-exchange resin to separate a melamine-derived compound and a non-melamine-derived compound. ^It was calculated from the relative proton ratio of the peak derived from melamine and the peak derived from phenol by ¹ H-NMR.

[0013]

[Table 1]

[0014]

Industrial Applicability The present invention provides a liquid composition of a melamine-based alkylene oxide adduct which is easy to handle, and particularly provides a liquid composition useful as a flame retardant for urethane. Another object of the present invention is to provide a low-cost, high-yield production method of the liquid composition.

Claims (2)

[Claims] 1. A liquid composition comprising the following (a) and (b): (A) An alkylene oxide adduct of melamine or an alkylene oxide adduct of a melamine derivative. (B) An alkylene oxide adduct of phenol or an alkylene oxide adduct of benzyl alcohol. 2. The process for producing a liquid composition according to claim 1, wherein the alkylene oxide is added to melamine or a melamine derivative in the presence of an alkylene oxide adduct of phenol or an alkylene oxide adduct of benzyl alcohol.