Mitsui Toatsu Chemicals, Incorporated

Michihiro Tsujimoto

Kiyoharu Hasegawa

Ichiro Okubo

Makoto Asano

Hiroyuki Akahori

Tsutomu Nishizawa

Ryoichi Tsukahara

Eishi Tanaka

Masaaki Torisu

Kisuke Osawa

Nobuyoshi Abe

Disclosed herein is a novel benzoquinone derivative represented by the following general formula (I): ##STR1## wherein R.sub.1 means an alkyl or cycloalkyl group, R.sub.2 denotes an alkyl or cycloalkyl group, a phenyl group which may optionally contain one or more halogen atoms and/or alkyl, cycloalkyl, alkoxy, alkylene, phenoxy, phenyl and/or biphenylyl groups, or a benzyl or naphthyl group which may optionally contain one or more methyl groups. This compound is useful as an oxidative color-developing agent for recording materials.

Novel benzoquinone derivatives and production process thereof as well as

Process for the preparation of triarylmethane compounds

Heat-sensitive recording unit

Dyestuff-containing microscopic capsule suspension for record materials, containing in microscopic capsules a lactone family dyestuff represented by the general formula (I): ##STR1## wherein a, b, c and d are each a carbon atom or either one or two atoms of said a, b, c and d are nitrogen atoms and the remaining atoms are carbon atoms, said a, b, c and d may have one or two substituent groups, adjacent a-b, b-c or c-d bond may form another ring, X and Y represent individually a benzene, naphthalene or aromatic heterocyclic ring which may include one or more substituent groups, and X and Y may be the same or different and may be coupled together to form a ring; and a metal ion sequestering agent in the capsules or a liquid medium in which the capsules are suspended.

Dyestuff-containing microscopic capsule suspension for record materials

Disclosed is a pressure sensitive recording unit which comprises a single base web sheet and a methine-type dyestuff and an organic oxidizing compound both supported on the single base web sheet, or a combination of first and second base web sheets and the methine-type dyestuff and organic oxidizing compound supported individually on the first and second base web sheets. Such a recording unit includes for example a pressure sensitive recording unit formed in combination of (a) a back-coated topsheet (CB-sheet) making use of microscopic capsules containing a solution obtained by dissolving a methine-type dyestuff in a solvent having a high boiling point and (b) a front-coated undersheet (CF-sheet) carrying an organic oxidizing compound coated thereon. Also disclosed is a pressure sensitive recording unit which includes a base web sheet carrying thereon such a methine-type dyestuff together with a metal ion sequestering agent and/or alkanol amine.

Pressure sensitive recording unit

A dyestuff-containing microscopic capsule dispersion for record materials, which comprises at least one methine dyestuff represented by the general formula (I): ##STR1## wherein X means a phenyl, naphthyl, indolyl, .beta.-styryl, pyridyl, pyrimidyl or pyrazinyl group which may optionally be substituted, R.sub.1 -R.sub.6 are individually an amino, substituted amino, lower alkyl, cycloalkyl, lower alkoxy or lower haloalkyl group or a halogen or hydrogen atom, R.sub.7 and R.sub.8 are each a hydrogen or halogen atom or a lower alkoxy group and may be coupled together to form a ring, and said methine dyestuff contains at least one substituted amino group at a position para to the central methine group in the molecule thereof, said methine dyestuff being contained in microscopic capsules; and alkanolamine represented by the general formula (II): ##STR2## wherein R denotes a lower alkylene, hydroxyalkylene or poly(oxyalkylene) group, R' and R' mean individually a hydrogen atom, an alkyl, hydroxyalkyl, aryl, aralkyl, acyl, or .omega.-hydroxyalkyl-polyoxyalkylene group or a lower alkyl ether of an .omega.-hydroxyalkyl-polyoxyalkylene group, and R' and R' may be coupled together to form a ring, and/or a metal ion sequestering agent, said alkanolamine and/or metal ion sequestering agent being contained in said microscopic capsules and/or a liquid medium wherein said microscopic capsules are dispersed.

Dyestuff-containing microscopic capsule dispersion for record materials

Novel chlorinated 4-methylphthalic acids or anhydrides of the general formula ##STR1## wherein n is an integer of 1, 2 or 3, with the proviso that when n is 1, the chlorine atom is positioned at 3- or 5-position and when n is 2, the chlorine atoms are positioned at 3- and 5-positions. The new compounds are produced by dissolving 4-methylphthalic anhydride in concentrated sulfuric acid or fuming sulfuric acid to form a solution, and reacting the solution with chlorine at room temperature preferably in the presence of a catalytic amount of iodine, thereby to yield a crude product containing a mixture of chlorinated 4-methylphthalic acids. By subjecting the mixture to a thermal dehydration treatment in an inactive organic solvent, each of the chlorinated compounds may be isolated as its corresponding anhydride in the form of crystals. These chlorinated 4-methylphthalic anhydrides are valuable as intermediates for the preparation of dyestuffs or pigments.

Chlorinated 4-methylphthalic anhydrides

Method of coloring an organic material with the naphthacenequinone derivative having the formula: ##STR1## wherein X is --OH, --NH.sub.2, --NHR' wherein R' is lower alkyl or aryl group, Y is --H, --Cl, --OH, --OR'' --SR'', --NH.sub.2, --NHR'', methyl, cyclohexyl or benzyl group wherein R'' is aryl or alkyl which may be substituted with lower alkoxy or lower alkylthio group, R and R' is --H, --Cl, --CH.sub.3, --OCH.sub.3, phenyl group or may together form a benzene ring. Colored organic materials with the compound exhibit brilliant nuance with characteristic fluorescence.

Coloring of the organic materials with naphthacenequinones

Method of coloring an organic material with a naphthacenequinone derivative having the formula: ##STR1## wherein R.sub.1 and R.sub.3 are members selected from the group consisting of hydrogen, chlorine, hydroxyl or amino, R.sub.2 is a member selected from the group consisting of carboxyl or its derivative, sulfonamide, sulfonate and phenylsulfonate, X is a member selected from the group consisting of hydrazo and aromatic diamino. Organic materials with the compound have a brilliant hue with characteristic fluorescence and high sublimation fastness.

Coloring resins by mixing naphthacenequinones therewith

Method of coloring an organic material with an asymmetric thioindigoid compound having the formula: ##STR1## wherein R is a hydrogen atom or lower alkyl group; R' is a member selected from the group consisting of a hydrogen atom, halogen atoms, lower alkyl groups, lower alkoxy groups, sulfonamide group or its derivatives, and aryl sulfonate groups or their derivatives; R' is a hydrogen atom or methyl group; and X is an oxygen atom or sulfur atom. Organic materials colored with the compound have a brilliant nuance with characteristic fluorescence.

Coloring of organic materials with asymmetric thioindigoid compounds

2-Phenyl-1.2.3-triazole-4-carboxaldehydes having the formula: ##STR1## are obtained by oxidizing a 2-phenylglycosotriazole having the formula: ##STR2## wherein R is hydrogen, halogen, methyl, carboxyl, a sulfonic acid group or the alkali metal salt thereof, n is 2 or 3, R' is hydroxymethyl when n is 2 and is hydroxymethyl or methyl when n is 3, with an oxide of manganese such as manganese dioxide or manganese oxide in dilute sulfuric acid of 20 to 80 wt. % concentration at a temperature of 0.degree. to 80.degree. C. The oxidation reaction is carried out in a dispersed state for from 2 to 100 hours and the resultant aldehyde is separated from the reaction mixture by extraction with an organic solvent. The purity of the aldehyde thus obtained is higher than 85 wt. % and the yield is 40% to quantitative on the basis of 2-phenylglycosotriazole. The aldehyde can be further purified by convenient means.

Process for producing substituted or unsubstituted

Method of coloring an organic material with a naphthacenequinone derivative having the formula ##SPC1##

Dyeing synthetic and semisynthetic materials with naphthacenequinine

Method of coloring a synthetic or semisynthetic organic high molecular weight material with a asymmetric thioindigoid compound having the formula ##SPC1## Wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and are selected from the group consisting of a hydrogen atom, chlorine atom, lower alkyl group, lower alkoxy group, cyclohexyl group, phenyl group, benzyl group and styryl group, the benzene nucleus of the phenyl and benzyl group may be optionally substituted with a methyl group or chlorine atom, R.sub.1 and R.sub.2 may together form a tetramethylene ring, R.sub.4 is a hydrogen atom or methyl group with the proviso that R.sub.4 is a methyl group when R.sub.1, R.sub.2 and R.sub.3 are each a hydrogen atom and R.sub.4 is a hydrogen atom when R.sub.1 is a methyl group and R.sub.2 and R.sub.3 are each a hydrogen atom. The colored organic high molecular weight materials exhibit brilliant nuance with characteristic fluorescence.

Method of coloring an organic material with an asymmetric thioindigoid compound having the formula: ##SPC1## Wherein R is a hydrogen atom or lower alkyl; R' is a member selected from the group consisting of a hydrogen atom, halogen atoms, lower alkyl groups, lower alkoxy groups, sulfonamide group or its derivatives, and aryl sulfonate groups or their derivatives; R' is a hydrogen atom or methyl group; and X is an oxygen atom or sulfur atom. Organic materials colored with the compound have a brilliant nuance with characteristic fluorescence.

Growing community of inventors

Tachikawa, Japan

Michihiro Tsujimoto