JPS6023464A - Production of fluorescence developing material for writing utensil containing quinazolone derivative as main agent - Google Patents

Abstract

PURPOSE:To provide a visible substance for writing utensils, developing fluorescence by the irradiation of ultraviolet rays when used as a colorant of color pencil, crayon, ink, etc., by using a quinazolone derivative as a main component, and dispersing a polycondensation polymer compound, a rubber, water, etc. in the above component. CONSTITUTION:A quinazolone derivative [a compound which is almost colorless under white light and emits strong fluorescence by ultraviolet irradiation, preferably e.g. the compound of formula (X is aromatic sulfonyl)] is used as a main component, and is mixed and dispersed with one or more materials selected from polycondensation polymer compound, thermoplastic resin, rubber, wax, paraffin, clay, water, and solvent, at normal temperature or under heating.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a fluorescent substance for writing using a quinazolone derivative as a main ingredient. , Powder Ink ○Printing ink, transfer ink, rubber ink, stamp ink, etc., which attempt to provide substances that exhibit fluorescence when irradiated with ultraviolet rays.

Quinazolone derivatives R,, R11, R,, R4 Various substituents (including H) It is recognized that some of these quinazolone derivatives exhibit fluorescent properties.

Of the compounds having this quinazolone skeleton, the present invention has selected the following (I ) The method for producing thanoyl anthranilic acid anhydride (aminophenylbenzoxazinone) as a starting material is shown below.

Aminophenylbenzoxazinone This primary amine group was treated with an aromatic sulfochloride and the oxygen atom in the ring was replaced with a nitrogen atom to convert it into a quinazolone derivative, as shown in the following (IN).

2-(2-(aromatic sulfamide)-ph22-4-quinazolinone is produced.

X-Aromatic sulfonyl group This compound is almost colorless under white light, but has the property of emitting strong fluorescence when irradiated with ultraviolet light.

The present invention is a method for producing the above-mentioned fluorescent material for writing using this quinazolone derivative as a main ingredient.First, a specific example of the method for obtaining this quinazolone derivative will be shown in order.

The anthranoylanthranilic anhydride 109- shown in (i) above is dissolved in a solvent such as methyl cellosolve 80CQ.
, is dissolved in pyridine 8ω, and balatoluene sulfochloride 20P is gradually added thereto at room temperature, the temperature is raised to 40-50"C with stirring, and 300 cc of concentrated aqueous ammonia is added and stirred. Then, 2. A solution of caustic soda No. 11 dissolved in water No. 12 is added and heated under reflux for 2 to 3 hours. After the reaction is complete, the reaction solution is acidified with acetic acid and left to stand, resulting in 2-(2- (P-)luenesulfoamid)-phenyl)-4-quinazolinone is precipitated.

When this is recrystallized using orundichlorobenzene□hexane solvent, a substance having a melting point of 280°C can be obtained.

Although this substance is almost colorless, it is observed to emit strong fluorescence when irradiated with ultraviolet light.

Example 2゜In the previous example, paratoluenesulfochloride was used to introduce aromatic sulfonic acid residues, but even if benzenesulfochloride is used, the corresponding quinazolinone can be produced by performing the same procedure as in the previous example. can do. That is, as X of G[), the melting point of the pen substance is 2 when recrystallized.
It shows 82°C.

Although this substance is almost a colorless compound, it also emits strong fluorescence when irradiated with ultraviolet light.

Here, the above two examples of quinazolone derivatives are used as the main agent,
The gist is to mix one or more of polymeric polymer compounds, thermoplastic plastics, rubbers, waxes, paraffins, rosins, clay, water, and solvents, and disperse the mixture at room temperature or under heating. Examples of the method of the present invention are shown below. The numbers on each side are in weight % (?γ).

0 Example 1゜-4(3)-quinazolonequidylole 44 Ethylcyclohexane 38 Maleated rosin 10 Polyoxyethylene nonylphenol ether 2 Maleated rosin and polyoxyethylene nonylphenol ether in a key/role and ethylcyclohexane mixed solvent After addition, stir and dissolve, gradually add 2-(! and stir and disperse thoroughly to prepare ink.

The ink is achromatic and UV rays (525 with 365n+Q irradiation)
nm.

emits fluorescent light. This is suitable for oil-based marking pens.

○ Example 2゜2-(2-penzamidophenyl) -+(:sr-quinazolone 9 Polyvinylpyrrolidone 2 Hydroxyethyl cellulose 0.5 Sodium dialkyl sulfosuccinate 0.1 Polyoxyethylene nonylphenol ether 01 Ethylene glycol U Benzoin Acid Sodium 0.3 Water 64 Hydroxyethylcellulose, Polyvinyl Pyrrolide 1
) and ethylene glycol are mixed and dispersed uniformly, water is added and dissolved. Sodium dialkyl sulfoconophosphate, polyoxyethylene nonylphenol ether, and 2-(2-benzamidophenyl)-4(3)-quinazolone, After adding sodium benzoate and premixing,
Thoroughly disperse the ink by applying it to an attritor to prepare an ink for water-based felt veneers. The ink is achromatic and emits fluorescence at 546 nm when exposed to ultraviolet light.

Example 8゜2-(4-Methoxyphenyl)-4(3) Quinazolone 12 Methyl cellulose 02 Polyvinylpyrrolidone 8 Glycerin A Polyoxyethylene nonylphenol ether 0,2 Naphthalenesulfonic acid formalin condensate Sodium 2 Sodium benzoate 0. 3 Water 32.3 After mixing and uniformly dispersing methylcellulose and polyvinyl pyrrolidone, add glycerin and dissolve, polyoxyethylene nonylphenol ether, naphthalene sulfur
After sequentially adding and premixing formalin phonate, 2-(4-methoxyphenyl)-4(3) quinazolone, and sodium benzoate, the mixture is dispersed using an attritor to prepare an ink. The ink is suitable for use as an aqueous stamp ink. Achromatic color with UV irradiation of 472 nm
, emits fluorescent light.

Example 4゜2-(2-hydroxy-4-chlorophenyl)12
-4 (3)-Quinazolone clay ρ Talc 8 Liquid paraffin 14 Beeswax 8 Wood wax 16 Carpoxymethyl cellulose H1 Gum arabic 5 Gum tragacanth 5 2-(2-hydroxy-4-chlorophenyl)-4
(3) - Liquid paraffin was added to quinazolone and kneaded well to fully disperse the mixture, then beeswax, wood wax, carboxymethyl cellulose, gum arabic, and gum tragacanth were mixed and melted by heating to a temperature of 120°C to mix uniformly. rear,
Add clay and talc, disperse uniformly, and cool to prepare lead for colored pencils. The colored pencils are achromatic and have a color of 51 when exposed to ultraviolet light.
It emits fluorescent light of 2 nm.

Example 5゜2-(2-benzenesulfamidophenyl)6-4 (
3) - Quinazolone wax stearic acid r O liquid paraffin 12 Precipitated magnesium carbonate, mu 15 0 resin 4 2-(2-benzenesulfamidophenyl) -4 (3)
- Add liquid paraffin to quinazolone (knead and disperse thoroughly. Mix and melt the wax, stearic acid, precipitated magnesium carbonate, and rosin while heating to 120°C and disperse uniformly, then cool. A crayon is prepared.The crayon is achromatic and emits fluorescence at 520 nm when exposed to ultraviolet light.

Example 6゜2-(2-hala)luenesulfamidophenyl)7-4
(3)-Quinazolone benzyl alcohol I Ethylene glycol monophenyl ether 42 Ketone resin 18 Polyvinyl pyrrolidone 2. O N-alkyltrimethylenediamine oleate 1.
After thoroughly dispersing 2-(2-paratoluenesulfamidophenyl)-4(3)-quinazolone in a mixed solvent of 0-benzyl alcohol and ethylene glycol monophenyl ether, ketone resin, polyvinyl pyrrolidone, and N- A ballpoint pen ink is prepared by adding alkyltrimethylenediamine oleate soda and sufficiently dissolving and dispersing it. The ballpoint pen ink is achromatic and emits fluorescence at 525 nm when irradiated with ultraviolet light.

Example 7゜2-(2-paratoluenesulfamidophenyl)11-
4(3)-Quinazolone brilliant carmine 5B 1 ○ Clay Added paraffin-14 Beeswax 10 Wood wax 16 Hydroxyethylcellulose 8 Gum arabic 6 Gum tragacanth 6 Talc 8 2-(2-halatoluenesulfamidophenyl)-4(
3) - Add liquid paraffin to quinazolone and knead well to fully disperse it, then add beeswax, plywood wax, hydroxyethyl cellulose, gum arabic, and gum tragacanth.
After heating and melting to 20°C and mixing uniformly, clay and talc are added and dispersed, and the mixture is cooled to prepare a colored pencil lead.

This product has a red color and is 624nm after being irradiated with ultraviolet rays.
m, emits fluorescent light.

Example 8゜-4(3)-Quinazolone rhodamine B base 4 Xylo-A/62 n-butanol 16 0 Zineste/I/10 Polyoxyethylene nonylphenol ether 20-
An ink is prepared by processing and dissolving rosin ester and polyoxyethylene nonylphenol ether in a mixed solvent of Damin B base, Kijirol and hin-7'tanol. The ink is suitable for oil-based marking pens, has a red color, and has a wavelength of 53Q nm when irradiated with ultraviolet rays.

emits fluorescent light.

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Claims (1)

[Claims] The main ingredient is a quinazolone derivative, and one or two of these include polycondensation polymer compounds, thermoplastics, rubbers, waxes, paraffins, rosins, clay, water, and solvents.
A method for producing a revealing substance for writing, the main ingredient of which is a quinazolone derivative, which is characterized by mixing seeds or more and dispersing at room temperature or under heating.