Patent GB-1017695-A (GB)
Title: Chromogenous aminophenyl derivatives of benzodifurandione and marking method using same
IPC: B41M5/145
Filed: 1962-08-22
Abstract: The invention comprises (A) compounds having the structural formula:- <FORM:1017695/C4-C5/1> (B)  isomers thereof having the structural formula:- <FORM:1017695/C4-C5/2> and (c) mixtures of compounds (A) and (B), in which each of X and X1 is a radical of the formulae:- <FORM:1017695/C4-C5/3> <FORM:1017695/C4-C5/4> or <FORM:1017695/C4-C5/5> or an N-substituted aminonaphthyl radical having as N-substituents R and R1, wherein Q and Q1 are hydrogen or any of methyl, fluoro, chloro or bromo in 2- or 5-position or any two of these in the 2- and 5-positions and R and R1 are alkyl or hydroxyalkyl of up to 5 carbons, n-hexyl, cycloalkyl, chloromethyl, benzyl, phenyl, sulphophenyl, tolyl or methyl-benzyl or together with the N-atom form a piperidino radical and wherein R1 may also be hydrogen.  The invention further comprises the dark-coloured substance developed by contacting the above compounds and mixtures (A), (B) and (C) with a substance which is electrophilic thereto, e.g. attapulgite and argosite clay, magnesium trisilicate, activated silica, sodium aluminium zeolite, bentonite, calcium sulphate, basic aluminium sulphate, calcium fluoride, citric acid and tartaric acid.ALSO:In an Example (2) an isomeric mixture of 2:5 - bis - (41 - dimethylaminobenzoyl) terephthalic acid and 4:6-bis-(41-dimethylaminobenzoyl)-isophthalic acid is made by reacting N:N-dimethylaniline with pyromellitic dianhydride in carbon disulphide in the presence of aluminium chloride; on heating the isomeric mixture with N:N-dimethylaniline and acetic anhydride a mixture is obtained of the monolactones of the formulae <FORM:1017695/C2/1> and <FORM:1017695/C2/2> In a further Example (9) an isomeric mixture of 2:5-bis-(9-julolidylcarbonyl) terephthalic acid and 4:6 - bis - (9 - julolidylcarbonyl) isophthalic acid is similarly prepared from julolidine and pyromellitic dianhydride.ALSO:A manifolded set, which may be of paper sheets, comprises a first web 11 having on one side a transfer coating 12 containing a colourless or lightly-coloured substance (A), (B) or (C) described below, and a second web 13 carrying on one side an adherent coating 14 containing a colour-activating substance which is electrophilic relative to substance (A), (B) or (C), coatings 12 and 14 being in face-to-face relationship so that on impact the substances are brought into contact with each other and a dark-coloured mark is formed.  The substances are (A) compounds of the formula:-  <FORM:1017695/D1-D2/1> (B) isomers thereof of the formula:-  <FORM:1017695/D1-D2/2> and (C) mixtures of compounds (A) and (B), in which each of X and X1 is a radical of the formula:- <FORM:1017695/D1-D2/3> or an N-substituted aminonaphthyl radical having as N-substituents R and R1, wherein Q and Q1 are hydrogen, any of methyl, fluoro, chloro or bromo in 2- or 5-position or any two of these in 2- and 5-positions and R and R1 are alkyl or hydroxyalkyl of up to 5 carbons, n-hexyl, cycloalkyl, chloromethyl, benzyl, phenyl, sulphophenyl, tolyl or methylbenzyl or together with the N-atom form a piperidino radical and wherein R1 may also be hydrogen. Electrophilic colour-activating substances are attapulgite clay, argosite clay, magnesium trisilicate, calcined diatomaceous silica, activated silica, sodium aluminium zeolite, pyrophyllite, bentonite, halloysite, magnesium montmorillonite, the sulphates of calcium, zinc and barium, basic aluminium sulphate, calcium fluoride, acetic acid, citric acid and tartaric acid.  The second web 13 may be modified by the addition of an optional transfer coating 15 similar to coating 12 and one or more additional webs identical with web 13 carrying the coating 15 may be manifolded beneath the modified web 13.  A modified web 13 may also form the top sheet of a manifolded set.  The units of the manifolded set may be fastened together in a pad.  The transfer coating may comprise solid (A), (B) or (C) bonded to the web by a solid adhesive or binder, e.g. a waxy or plastic material, or the coating may be a film-forming material rupturable on impact and containing as a finely dispersed phase numerous cells of a liquid vehicle in which is dissolved the substance (A), (B) or (C).  The film-forming material may be casein, gelatin or polyvinyl alcohol applied as a hydrophilic aqueous composition containing the liquid vehicles emulsified therein.  Vehicles specified are chlorinated biphenyl, benzyl butyl phthalate, benzyl salicylate, phenyl ether or halogenated phenyl ethers and mixtures thereof.  The adherent coating 14 contains the colour-activating substance bonded by a starch or polybutadiene-styrene binder.