JPH05987A - Aromatic ether - Google Patents

Abstract

PURPOSE:To provide the subject thermally stable compound having large solubility and effective as an additive for thermosensitive sheet, pressure-sensitive sheet, heat-transfer recording sheet, etc., for highly sensitizing the sheets. CONSTITUTION:A compound of the formula (R1-R4 are H, halogen, alkyl, aryl, etc., but R1 and R2, and R3 and R4 may be combined with each other into a ring, respectively). For example, 1,5-diphenoxy-3-methylpentane. The compound of the formula is produced e.g. by reacting a phenolic compound or phenolate compound with an aryloxyalkyl sulfonate in the presence of a catalyst such as sodium hydroxide or copper powder at 30-150 deg.C in a solvent such as DMF or methanol, which nitrogen gas is bubbled.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an aromatic ether which is useful as a sensitizer for a recording material utilizing the dissolution or melting of various organic compounds, particularly a heat-sensitive recording material.

[0002]

2. Description of the Related Art The present inventors have made various recording materials (heat-sensitive paper,
Various additives have been investigated for pressure sensitive paper, thermal transfer recording paper, laser recording paper). And we have developed various ethers and diethers. This time, we have newly found a compound that has a skeleton different from that of conventional ethers and is effective for increasing the sensitivity.

[0003]

DISCLOSURE OF THE INVENTION The present invention is to develop a novel aromatic ether compound which is thermally stable, has high solubility, and is effective for high sensitivity.

[0004]

The above object has been achieved by developing a branched ether represented by the general formula (1). General formula (1)

[0005]

[Chemical 2]

In the formula, R ₁ , R ₂ , R ₃ and R ₄ may be the same or different and each is a hydrogen atom, a halon atom, an alkyl group, an aryl group, an acyl group, an aralkyl group, an alkoxycarbonyl group or a cyano group. , A thioalkoxy group, a phenoxy group, an aryloxy group or an alkoxy group, R
₁ and R ₂ , and R ₃ and R ₄ may be bonded to each other to form a 5- or 6-membered ring composed of a non-metal atom.

Specific examples of the compound of the present invention are shown below.
1,5-di-phenoxy-3-methylpentane, 1,5
-Bis (p-methoxyphenoxy) 3-methylpentane, 1,5-bis (p-ethoxyphenoxy) 3-methylpentane, 1,5-bis (p-methylphenoxy) 3
-Methylpentane, 1,5-bis- (ethylphenoxy) 3-methylpentane, 1,5-bis (p-isopropylphenoxy) 3-methylpentane, 1,5-bis (p-chlorophenoxy) 3-methylpentane 1, 5
-Bis (p-acetylphenoxy) 3-methylpentane, 1,5-bis (β-naphthoxy) 3-methylpentane, 1,5-bis (α-naphthoxy) 3-methylpentane, 1,5-bis (3 , 5-dimethylphenoxy) -3
-Methylpentane, 1,5-bis- (p-methylthiophenoxy) 3-methylpentane and the like.

These are obtained by reaction of corresponding phenols, phenolates with aryloxyalkyl sulfonates, reaction with aryloxyalkyl halides or reaction of corresponding alkylene dihalides with phenols.

In the above reaction, polar solvents such as dimethylformamide, dimethylacetamide, sulfolane, hexamethylphosphoramide, 2-methyl-N-methylimidazole and dimethylsulfoxide, methanol, isopropanol, diethylene glycol, cellosolve, etc. Alcohol, diglyme, ether acetone such as tetrahydrofuran, methyl ethyl ketone, ketones such as methyl isobutyl ketone, xylene, aromatics such as cumene, halides such as trichloroethylenedichloroethane, acetonitrile, using various solvents such as water alone or in combination, As a catalyst, caustic soda, caustic potash, potash carbonate, potash fluoride, etc., hardness, potash, copper powder,
Inorganic compounds such as copper chloride, phase-transfer catalysts such as benzyltributylammonium chloride and amylpyridinium bromide, combined use of polyethylene glycol, etc. 30
It is also possible to take various means for promoting the reaction, improving yield or improving purity, such as adjusting the temperature to 150 ° C., passing nitrogen gas during the reaction, or using a trace amount of sulfite together.

It is also possible to use equimolar amounts or more of components that are easily dissolved in water or alkaline water during the reaction. In that case, after the reaction, it is convenient to pour into water and separate the precipitated product. The present invention will be described in detail below with reference to examples.

[0011]

【Example】

Example 1 Synthesis of 1,5-bis (p-methoxyphenoxy) 3-methylpentane In a three-necked flask equipped with a stirrer and an air condenser, 3
-Methyl-1,5-pentanediol bis-p-toluenesulfonate 0.1 mol, dimethylformamide 1
Weigh 00 ml. 0.22 mol potassium carbonate and 0.21 mol p-methoxyphenol are added with good stirring. After holding at 90 to 95 ° C. for 4 hours, when poured into water, white crystals start to precipitate. The crystals obtained are collected by filtration and then recrystallized from methanol / ethyl acetate. The yield was 75% and the melting point was 95 ° C.

Examples 2 to 3 Example 2 The same experiment was conducted except that the p-methoxyphenol used in Example 1 was replaced with phenol. 1,5-di-phenoxy-3-methylpentane melting point 4
6 to 47 ° C. Example 3 A similar experiment was performed except that β-naphthol was used instead of p-methoxyphenol used in Example 1. 1,5-bis (β-naphthoxy) 3-methylpentane
Melting point 107-108 ° C

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical display location C07C 43/225 C 8619-4H 49/84 C 9049-4H 69/92 9279-4H 255/54 8519 -4H 323/20 8217-4H 323/21 8217-4H 323/62 8217-4H

Claims (1)

[Claims] 1. An aromatic ether of the general formula (1) General formula (1) [Chemical 1] Where R₁, R₂, R₃, R_FourAre the same or different
Well, hydrogen atom, halogen atom, alkyl group, aryl
Group, acyl group, aralkyl group, alkoxycarbonyl
Group, cyano group, alkylthio group or alkoxy group
And R₁And R₂, R ₃And R_FourMay form a ring with each other
Yes.