Verfahren zur Herstellung von farbigen Kondensationsprodukten

• Main Author: PUGIN,ANDRE,DR
• Format: Patent
• Language: German
• Published: 15.05.1960
• Subjects: ADHESIVES; CHEMISTRY; COMPOSITIONS BASED THEREON; DYES; HETEROCYCLIC COMPOUNDS; LAKES; METALLURGY; MISCELLANEOUS APPLICATIONS OF MATERIALS; MISCELLANEOUS COMPOSITIONS; MORDANTS; NATURAL RESINS; ORGANIC CHEMISTRY; ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES; ORGANIC MACROMOLECULAR COMPOUNDS; PAINTS; POLISHES; THEIR PREPARATION OR CHEMICAL WORKING-UP; USE OF INORGANIC OR NON-MACROMOLECULAR ORGANIC SUBSTANCES ASCOMPOUNDING INGREDIENTS

3 - Imino - isoindole - 1 - ones containing at least three halogen atoms in the benzo radical are made by treating with ammonia or a primary amine the correspondingly halogenated 1 : 3 : 3 - trichloro - isoindolenines, which may be made from the corresponding phthalimide by reaction with 2 mols. of phosphorus pentachloride in absence of moisture, or by similar treatment of 3 : 3-dichloro-isoindole-1-ones containing at least three halogen atoms in the benzo radical. The latter may be made by reacting at least one mol. of phosphorus pentachloride with the corresponding phthalimide or by hydrolysis of the corresponding 1 : 3 : 3 - trichloroisoindolenine. The 3 - imino - isoindole - 1 - ones are also made by heating tri- or tetra-halogen phthalic acid anhydride in nitrobenzene with urea and ammonium molybdate.ALSO:The invention comprises coloured condensation products of the formula <FORM:0833548/IV(c)/1> where Hal is a halogen atom, R is a direct linkage when m = 0 or the radical of an organic compound of the homo- or hetero-cyclic aromatic series, the nitrogen atoms being directly bound to the aromatic nucleus of the radical, n is 3 or 4 and m is 0 or 1. The invention further comprises a process for making coloured condensation products by condensing polyprimary amino compounds of the homo- or hetero-cyclic aromatic series or hydrazine with a molecular equivalent for every primary amino group thereof of the same or different isoindole-1-ones containing at least 3 halogen atoms in the benzo radical and containing in the 3-position an imino group which may be organically substituted, a doubly bound sulphur atom, two halogen atoms, two secondary amino groups or two ether groups. Instead of an isoindole-1-one containing two halogen atoms in the 3-position, a 1 : 3 : 3-trichloro-isoindolenine may be used provided water is present. The polyprimary amino compounds mentioned include those derived from stilbene, naphthalene, anthraquinone, thiazoles, oxdiazoles and thiadiazoles. Examples are given. The condensation products colour synthetic polymers such as polyvinyl chloride, lacquers, rubber, viscose or cellulose esters in the mass, paper and cellulose and animal fibres.ALSO:A thin foil is made by mixing on a roller frame polyvinyl chloride, dioctyl phthalate, titanium dioxide, dibutyl tin dilaurate and a pigment having the formula <FORM:0833548/IV (a)/1> where R is the 3 : 31-dimethoxy-4 : 41-diphenylene radical. A mixture comprising titanium dioxide, a 60% solution of a modified urea alkyd resin in xylene/butanol 1 : 1, turpentine oil and xylene and a pigment of the above formula, where R is the 4 : 41-diphenylene radical is milled in a ball mill, poured on to aluminium sheets and annealed.