Appleton Papers Inc.

Appvion, Inc.

Ponnampalam Mathiaparanam

Mark Robert Fisher

John Charles DeBraal

Stacey Ann Justa MacNeil

Debra Arlene Berggren

Kenneth D Glanz

Dean G Dalebroux

The invention teaches an improved process for the manufacture of useful fluoran dyes of the structure according to formula 1  comprising condensing in an alkanesulfonic acid or an arenesulfonic acid to acid according to formula 2  with an aminodiphenylamine of formula 3  wherein R, R-Rare as defined in the specification.

Process for manufacture of fluoran dyes

A linerless label system comprising pressure adhesive coating, release coating and thermal imaging coating is described. The thermal imaging coating contains as one of its components the compounds of the formula (I)  The imaged linerless label according to the invention has been a bar reflectance of less than 20 at 670 nanometers, a print control contrast signal of at least 80 and a BNL background of at least 75%.

Linerless labels

Thermally-responsive record material

Modifier compounds

The present invention is a novel process, with or without solvent, for manufacture of compounds of the formula

Process for preparing alkoxy or arylmethoxy aroxyethanes

Novel bis-(indolyl)ethylenes, process for their production and record systems utilizing such bis-(indolyl)ethylene chromogens are described.

Bis-(indolyl)ethylenes: process for their preparation

Preparation of novel mono(indolylethylenyl) phthalides is disclosed. Specifically, these compounds are chromogenic mono(indolylethylenyl)phthalides of the formula ##STR1## wherein A is as hereinafter defined and selected from moieties of the type ##STR2## wherein L is an indole moiety as hereinafter defined; wherein B is a moiety of the type ##STR3## as hereinafter defined. The process disclosed comprises condensing indolylethylene with a keto acid or its derivative and an electron acceptor in an organic solvent.

Method of preparing mono (indolylethylenyl) phthalides

Mono(indolylethylenyl)phthalides

Pressure-sensitive and heat-sensitive record materials are described comprising a substrate, an acidic developer and chromogenic di-[bis-(indolyl) ethylenyl]tetrahalophthalides of the formula ##STR1## wherein each X.sup.1, S.sup.2, X.sup.3, and X.sup.4 is independently selected from chlorine or bromine;

Di[bis-(indolyl)ethylenyl]tetrahalophthalide record materials

A process for producing a bis-(indolyl)ethylene of the formula ##STR1## is described, wherein A, B, a, b, R, Z, R.sup.5', R.sup.6 and R.sup.6' are as defined in the specification, said method comprising reacting an indole of the formula ##STR2## with an acylindole of the formula in the presence of a Vilsmeier reagent selected from the group consisting of phosphoryl chloride, phosgene, oxalyl chloride, benzoyl chloride, thionyl chloride, alkanesulfonyl chloride, arene-sulfonyl chloride, alkylchoroformate, and arylchloroformate, together with a Lewis Acid selected from the group consisting of zinc chloride, boron trifluoride and aluminum chloride.

Process for bis(indolyl)ethylene synthesis

Bis-(indolyl)ethylenes of the following general formula are prepared: ##STR1## wherein a is 1 or 2, wherein b is 1 or 2, wherein each A is independently selected from a dialkylamino, dialkoxyalkylamino, diaroxyalkylamino, diarylamino, alkylarylamino, dicyloalkylamino, alkylcycloalkylamino, arylcycloalkylamino, pyrrolidino, piperidino, or morpholino radical, wherein each B is independently selected from A or an alkoxy, alkoxyalkyl or aroxy radical, wherein each R is independently selected from hydrogen, halogen, alkyl, or alkoxy, wherein each of R.sup.5, R.sup.5', R.sup.6, and R.sup.6' are each independently selected from hydrogen, alkyl (C.sub.1 -C.sub.8), alkoxyalkyl, aroxyalkyl, halogen, phenyl, or phenyl substituted by alkyl or alkoxy, the alkyl moieties referred to herein being of one to eight carbons, the cycloalkyl moieties referred to herein being of three to six carbons.

Bis-(indolyl)ethylenes

Preparation of novel symmetrical and unsymmetrical chromogenic di-[bis-(indolyl)ethylenyl]tetrahalophthalides is disclosed. Specifically these compounds are chromogenic di-[bis-(indolyl)ethylenyl]tetrahalophthalides of the formula ##STR1## wherein L and X are as hereinafter defined. The process disclosed involves condensing bis(indolyl)ethylenes with tetrahalophthalic anhydride in acetic anhydride, in the presence of an electron acceptor or preferably an acetate of Group I or II of the Periodic Table. Optionally, and preferably, where unsymmetrical di-[bis-(indolyl)ethylenyl]tetrahalophthalides are desired, indoles are reacted with an acylindole in the presence of a Vilsmeier reagent to form the starting bis(indolyl)ethylene.

Process for producing di[bis-(indolyl)ethylenyl]tetrahalophthalides

Novel bis-(indolyl)ethylenes, process for their production and record systems utilizing such bis-(indolyl)ethylene chromogens are described. Bis-(indolyl)ethylenes of the following general formula are prepared: ##STR1## wherein each L.sup.1 and L.sup.2 is the same or different and is each independently selected from indole moieties (J1) through (J4) (L.sup.1 need not be the same as L.sup.2), ##STR2## wherein Z is hydrogen, alkyl (C.sub.1 -C.sub.8), substituted or unsubstituted aryl, aralkyl, aroxyalkyl, alkoxyalkyl or halogen.

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Appleton, WI, United States of America

Ponnampalam Mathiaparanam