Patent GB-495460-A (GB)
Title: Improvements in the manufacture and production of carbon compounds of high molecular weight
IPC: C10L1/22
Filed: 1937-02-05
Abstract: Compounds of the general formula R-A-X. where R is the radicle of a cyclic compound having at least four condensed rings, A is a nitrogen bridge and X is an alkyl or alkenyl group of at least four carbon atoms, are manufactured by reacting a hydroxy or alkoxy compound containing the radicle R, e.g. a compound of the benzanthracene, perylene, benzperylene, benzophenanthrene, pyrene, chrysene, pyrazolanthrone, benzanthrone, azabenzanthrone, anthanthrene, dibenzanthrene, isodibenzanthrene, pyranthrene, dibenzanthrone, anthranthrone, allo-ms-naphthodianthrone, ms-anthradianthrene, ms-benzdianthrone, ms-naphthodianthrone, acridine, anthrapyridone, anthrapyrimidone, coeramidonine, anthrapyrimidinopyridone, anthrapyrimidinopyrimidone anthradipyrimidone, anthrapyrimidonopyrimidone or anthrapyridone series, with a compound containing an alkyl group of the said kind and at least one hydrogen atom attached to nitrogen, in the presence or absence of diluents, if desired under pressure.  The products may be used as additions to hydrocarbons, rubber or other natural substances, synthetic masses, oils, waxes, mineral oils, lubricating oils, medicaments and cosmetics, and in some cases as dyestuffs for fabrics or for the preparation of dyestuffs.  In examples: (1) hydroxypyranthrone (prepared from pyranthrone by nitration, reduction, diazotization and replacement of the diazo group by a hydroxyl group) or the corresponding methoxypyranthrone is heated with dodecylamine, to produce dodecylaminopyranthrone; corresponding alkylaminopyranthrones are obtained by heating hydroxypyranthrone with palm kernel fatty amine, dodecylamine, nonylamine, undecylamine or propylamine; the hydroxypyranthrone may be replaced by hydroxydibenzpyrenequinones, hydroxypyranthridones, hydroxy-allo-ms-naphthodianthrones, hydroxyanthanthrones or hydroxyperylenetetracarboxylic acid imides; (2) Bz2 : Bz21 - dihydroxydibenzanthrone is heated with dodecylamine, palmitylamine, octodecylamine or octodecenylamine; Bz2 : Bz21 - dimethoxyisodibenzanthrone may be similarly reacted with amines of high molecular weight; (3) 4-hydroxy-methyl-1 : 9 - coeramidonine is heated with dodecylamine, sodium hydrosulphite, methanol and water, after which copper acetate and pyridine are added and air led through the mixture; the compound obtained by reaction of cyclohexanone with 1 - amino - 4 - hydroxyanthraquinone may be similarly treated; (4) 4-hydroxy-Py3-acetyl-1 : 9-anthrapyridone is heated with butylamine solution, or with octylamine, dodecylamine or octodecenylamine; (5) 4-hydroxy-Bz2-methyl-Bz1-azabenzanthrone is heated with butylamine solution; the same product is obtained by reacting 4-amino-Bz2 - methyl - Bz1 - azabenzanthrone with butyl bromide; 4 - hydroxy - 2 : 8 - dimethyl-3 : 9-diazaperylene may be similarly reacted with octodecenylamine; (6) 2-methoxy-1 : 9 : 5 : 10-anthradipyrimidine is heated with dodecylamine; 2-ethoxy-1 : 9 : 4 : 10 - anthradipyrimidine may be similarly reacted with nonylamine; substituted alkylamino - 1 : 9 : 4 : 10 - anthradipyrimidines may be similarly obtained from methoxy - 1 : 9 : 4 : 10 - anthradipyrimidines substituted by methyl, ethyl, nonyl, cyano, thiocyano, amino, alkylamino, acylamino or other groups; (7) 5-amino-2-methoxy - 1 : 9 - anthrapyridimidine or 4-amino-2-ethoxy-1 : 9-anthrapyrimidine is heated with decylamine and nitrobenzene; 2-methoxy-1 : 9-anthrapyrimidine may be similarly reacted with myristylamine; (8) 4-amino-2-methoxy - 1 : 9 - anthrapyrimidine, or the compound obtainable from 1 : 4-diamino-2-methoxyanthraquinone and formamide, is heated with palmitylamine, or other higher alkyl amines, in the presence of ethyl alcohol; (9) 4 - hydroxy - N - or PyC-phenyl - 1 : 9-pyrroloanthrone is heated with octodecylamine and amylalcohol.  Hydroxyanthrapyrimidinopyridone is obtainable by heating 2-hydroxy-4-amino-1 : 9-anthrapyrimidine with acetone in aqueous alkaline suspension.  Hydroxyanthrapyrimidinopyrimidones are obtainable by heating hydroxy-4-amino-1 : 9-anthrapyrimidines with urea in nitrobenzene.  Hydroxyanthradipyrimidones are obtainable by heating 1 : 4- or 1 : 5-diaminohydroxyanthraquinones with urea in nitrobenzene.  Hydroxyanthrapyrimidonopyridones are obtainable by heating hydroxy-4- or 5-aminoanthrapyrimidones with acetone in the presence of aqueous alkali.  Hydroxyanthradipyrimidones are obtainable by heating 1 : 4- or 1 : 5-diaminohydroxyanthraquinones with acetone in aqueous alkaline medium.  4 - Hydroxy - Py3 - acetyl - 1 : 9 - anthrapyridone is obtainable by heating 1-amino-4-hydroxyanthraquinone with acetoacetic ester.  4 - Hydroxy - Bz2 - methyl - Bz1 - azabenzanthrone is obtainable by reacting 1 : 4-diaminoanthraquinone with acetone and saponifying the resulting 4-amino compound with diluted sulphuric acid.  4 - Hydroxy - 2 : 8 - dimethyl - 3 : 9 - diazaperylene is obtainable by reacting 1 : 5-diamino-2-hydroxyanthraquinone with acetone.  2 - Ethoxy - 1 : 9 : 4 : 10 - anthradipyrimidine is obtainable by treating 1 : 4-diamino-2-ethoxyanthraquinone with formamide.  4 - Amino - 2 - methoxy - 1 : 9 - anthrapyrimidine is obtainable by treating the corresponding 2-bromo compound with sodium methylate in the presence of methyl alcohol.  4 - Hydroxy - N - phenyl - 1 : 9 - pyrroloanthrone is obtainable by heating 1-chloro-4-hydroxyanthraquinone with the potassium salt of phenylaminoacetic acid and isobutyl alcohol under pressure in the presence of cuprous chloride and sodium acetate.  4 - Hydroxy - PyC - phenyl - 1 : 9 - pyrroloanthrone is obtainable by heating 1-amino-4-hydroxyanthraquinone with phenylbromacetic acid in the presence of sodium acetate.ALSO:Rubber is coloured or rendered fluorescent by the addition of compounds of the general formula R-A-X where R is the radicle of a cyclic compound having at least four condensed rings, A is a nitrogen bridge and X is an alkyl or alkenyl group of at least four carbon atoms.