Patent GB-1018795-A (GB)
Title: Chromogenous aminoderivatives of diphenylphthalan and marking method using same
IPC: C09B11/24
Filed: 1962-08-22
Abstract: The invention comprises (A) the compound of the formula:-<FORM:1018795/C4-C5/1> (B) the compound A in which the two paraaminophenyl radicals attached to the carbon atom designated 1 are linked by an epoxy bridge between the positions in said radicals ortho to said carbon atom 1, (C) the 5-amino derivatives of the compounds A and B, and (D) N-substituted derivatives of each of compounds A, B and C, the N-substituents being selected from alkyl groups of up to 5 carbon atoms, n-hexyl, cyclopropyl, napthyl, benzyl, phenyl, sulphophenyl, tolyl, methylbenzyl, chloromethyl and hydroxymethyl, and wherein the benzene rings of the said para-amino phenyl radicals may be further substituted by methyl, halo or nitro. The compounds are made by reduction with lithium aluminium hydride of the corresponding lactones having a CO group in place of the CH2 group in 3-position.  The invention further comprises the dark-coloured substances obtained by contacting the above substances with electrophilic colour-activating materials including attapulgite clay, magnesium silicate, calcium sulphate, calcium fluoride, citric acid, acetic acid and tartaric acid.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 chromogenous compound as described below, and a second web 13 carrying on at least one surface an adherent coating 14 containing an electrophilic colour-activating substance.  Th chromogenous compounds are (A) the compound of the formula:- <FORM:1018795/D1-D2/1> (B) the compound A in which the two para-aminophenyl radicals attached to the carbon atom designated 1 are linked by an epoxy bridge between the positions in said radicals ortho to said carbon atom 1, (c) the 5-amino derivatives of the compounds A and B, and (D) N-substituted derivatives of each of compounds A, B and C, the N-substituents being selected from alkyl groups of up to 5 carbon atoms, n-hexyl, cyclopropyl, naphthyl, benzyl, phenyl, sulphophenyl, tolyl, methylbenzyl, chloromethyl and hydroxyethyl, and wherein the benzene rings of the said para-aminophenyl radicals may be further substituted by methyl, halo or nitro. Electrophilic colour-activating substances specified include acidic clays such as attapulgite and argosite, activated silica, silicates such as magnesium silicate, calcium sulphate, calcium fluoride and acids such as citric, tartaric and acetic acids.  The second web 13 may be modified by adding an optional transfer layer 15 similar to coating 12 and one or more additional webs identical with the modified web 13 may be manifolded beneath the modified web 13 which may also form a top sheet of a manifolded set.  The units of the manifolded set may be fastened together in a pad. The transfer coating may comprise the solid chromogenous compound in a wax or thermoplastic binder, or the coating may be a film-forming material which is rupturable on impact and contains as a finely dispersed phase numerous cells of a liquid vehicle in which is dissolved the chromogenous compound.  The film-forming material may be casein or gelatin or polyvinyl alcohol applied as an aqueous emulsion containing the oily liquid vehicle. Vehicles specified are chlorinated biphenyl, partially hydrogenated terphenyls, benzyl butyl phthalate, lauryl bromide, butyl oleate, benzyl salicylate and halogenated diphenyl ethers and mixtures thereof.  The adherent coating may comprise the electrophilic colour-activating substance in a starch or polybutadiene-styrene latex binder.