JPS6130583A - 2,6-dibromo-4-tert-alkylphenyl glycidyl ether and its preparation - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I (R is 5-8C tert-alkyl). EXAMPLE:2,6-Dibromo-4-tert-pentylphenyl glycidyl ether. USE:An organic electrical insulating material for electricity and electronics. Having flame retardance, extremely low viscosity, and improved compatibility with epoxy resins. PREPARATION:A compound shown by the formula II (e.g., 2,6-dibromo-4-tert- pentylphenol, etc.) and preferably 2-8 times molar amount of epichlorohydrin based on the compound shown by the formula I are subjected to glycidyl formation reaction in the presence of both an alkali (preferably sodium hydroxide) and a catalyst (preferably phase transfer catalyst such as tetramethylammonium chloride, etc.). In case of necessity, a solvent such as benzene, etc. may be used.

Description

DETAILED DESCRIPTION OF THE INVENTION A. Industrial Application Field The present invention is directed to the following general formula (I) t( (I) (wherein R represents a tert-alkyl group having 5 to 8 carbon atoms). ) The present invention relates to 2,6-dipromo 4-tert-alkylphenyl glycidyl ether represented by the following formula and a method for producing the same.

The 2,6-dipromo 4-tert-alkylphenyl glycidyl ether represented by the general formula (I) obtained by carrying out the present invention can be used as a casting material, an impregnating material, a paint, an adhesive,
This compound is expected to have a wide range of uses, including as a sealant.

B. Conventional technology Conventional, 4-te! Because of its low viscosity, rt-alkylphenyl glycidyl ether can be used as a reactive diluent by electricity,
It is widely used as an insulating material for electronics, but
The flame retardancy required by the electronics industry was not always sufficient.

C1 Problems to be Solved by the Invention The 2,6-dipromo 4 represented by the general formula (I) of the present invention
-tert-furkylphenyl glycidyl ether is
Because it is flame retardant and has a reactive epoxy group,
Compared to additive-type flame retardants, there is less deterioration in the physical properties of the cured resin.

In addition, it exhibits properties such as low viscosity and excellent compatibility with various epoxy resins, and exhibits other properties that are superior to compounds with small alkyl groups in terms of flexibility, punching properties, work characteristics, etc. . Therefore, it is a useful compound that can be expected to have excellent performance as an organic insulating material for electrical and electronic applications.

The content of the present invention will be explained in more detail in terms of the means and method of action for solving and overcoming the D9 problem.

The substance of the present invention is a 2,6-dipromo-4-tert-alkylphenyl represented by the general formula (I) (wherein R represents a tert-alkyl group having 5 to 8 carbon atoms). It is a glycidyl ether, and is a new compound that has not been described in any literature.

The substance of the present invention is a 2,6-dipromo-4-tert-alkylphenol represented by the general formula (n) (wherein R represents a tert-alkyl group having 5 to 8 carbon atoms). It can be advantageously produced by reacting epichlorohydrin with an alkali using a catalyst to cause a glycidylation reaction.

In addition, 2,6-dipromo4 represented by general formula (II)
There are two methods for carrying out the glycidylation reaction using -tert-alkylphenol and epichlorohydrin as raw materials: There is a two-step method in which an addition reaction is first carried out using a catalyst such as a quaternary ammonium salt, and then a dehydrohalogenation reaction is carried out with an alkali, but this method is difficult in terms of yield and product purity. The latter two-step method is preferred.

The powder used for the above epichlorohydrin is 1% per 2.6-dimethylphenol of the raw material and 4-tert-alkylphenol.
~15 times by mole, preferably 2 to 8 times by mole. Epichlorohydrin used in excess can be recovered by distillation and reused. Furthermore, an organic solvent that does not participate in the glycidylation reaction can also be added. Examples of the organic solvent for this purpose include benzene, toluene, methyl isobutyl lactone, and the like.

Examples of the alkali include butrium hydroxide, potassium hydroxide, 11-lium hydrogen carbonate, butrium carbonate, and preferably sodium hydroxide or potassium hydroxide.

Further, as the catalyst, a phase transfer catalyst is preferable, whereby the glycidylation reaction can be carried out efficiently. Examples of the phase transfer catalyst include quaternary ammonium salts such as tetramethylammonium chloride, tetraethylammonium bromide, benzyltriethylammonium bromide, and phosphonium salts such as tetramethylphosphonium chloride and methyltriphenylphosphonium bromide.

Examples of other catalysts include alkali metal halides such as potassium bromide and potassium chloride, which may be used singly or in combination. The amount of catalyst to be used is 0.05 to 5 parts by weight per 100 parts by weight of raw materials.
．． It is about 0 parts by weight.

The reaction temperature varies depending on the type of reactants, but is usually 3.
The temperature is 0 to 120°C, preferably 40 to 90°C. The reaction time is until the reaction is substantially completed, and varies depending on the reaction temperature, but is usually 0.5 to 12 hours, preferably 2 to 8 hours.

E. Examples A more detailed explanation will be given below with reference to Examples, but these Examples are merely illustrative, and the present invention is not limited by these exemplifications.

[Example 1] 322 g (1.0 mol) of 2.6-dipromo-4-tert-pentylphenol, 370 g of epichlorohydrin
9 (4.0 mol) and 3.2 g of tetramethylammonium bromide were placed in a flask equipped with a thermometer, a condenser, a stirrer, and a water-epichlorohydrin separator for circulating epichlorohydrin into the reaction vessel at 80°C. The mixture was allowed to react for 4 hours.

Next, 78.4 g of 50% aqueous sodium hydroxide solution (0
, 98 mol) was added dropwise over 3 hours.

At this time, the inside of the system was set to about 150 #s HQ, and the water in the system was removed from the system by azeotroping with epichlorohydrin, while the reaction was carried out while circulating the shrimp chlorohydrin in the system.

After completing the dropwise addition of the aqueous sodium hydroxide solution, excess 1-pichlorohydrin was removed by distillation under reduced pressure.

Next, chloroform 800- was added to dissolve the glycidyl ether, and the mixture was washed with pure 500 #11+ four times to remove sodium chloride produced as a by-product in the reaction. Separate the organic layer;
After distilling off the solvent, vacuum distillation was performed to obtain 2,6-dipromo4.
-tert-pentylphenyl glycidyl ether 34
5g was obtained.

[Examples 2 and 3] Example 1 except that the compound described in Group 1 was used as the raw material
I did the same thing.

[Example 4.5] A reaction was conducted in the same manner as in Example 3 using the catalyst and solvent shown in Table 1 in the amounts shown in Table 1.

The above manufacturing method is shown in Table 1. In addition, the boiling point and infrared absorption spectrum (IR spectrum) of the obtained target compound
,')-1-The analysis results of nuclear magnetic resonance spectra (PMR spectra) are shown in Table 2.

L*) Comparative theoretical yield ◎) tert-hexyl is 1,1-dimethylbutyl ☆) tert-A ctyl is ? , 1,3.3-tetramethylbutyl Table 2

[Brief explanation of drawings]

Figures 1 to 3 are a chart showing the infrared absorption spectra of the compounds of Examples 1 to 3 of the present invention, respectively, and Figure 4 shows the nuclear magnetic resonance spectrum of the compound of Example 3 of the present invention. This is a diagram.

Claims (5)

[Claims] (1) The following general formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (I) (However, in the formula, R represents a tert-alkyl group having 5 to 8 carbon atoms.) 2,6 -dibromo-4-tert-alkylphenyl glycidyl ether. (2) 2,6-dibromo-4-tert-alkylphenyl glycidyl ether is 2,6-dibromo-4-t
A substance according to claim 1 which is ert-pentylphenyl glycidyl ether. (3) 2,6-dibromo-4-tert-alkylphenyl glycidyl ether is 2,6-dibromo-4-t
The substance according to claim 1, which is ert-hexylphenyl glycidyl ether. (4) 2,6-dibromo-4-tert-alkylphenyl glycidyl ether is 2,6-dibromo-4-t
The substance according to claim 1, which is ert-octylphenyl glycidyl ether. (5) The following general formula (II) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (II) (However, in the formula, R represents a tert-alkyl group having 5 to 8 carbon atoms.) 2,6 - A method for producing 2,6-dibromo-4-tert-alkylphenyl glycidyl ether, which comprises reacting dibromo-4-tert-alkylphenol with epichlorohydrin.