Patent GB-1037161-A (GB)
Title: 2-(ª¤-aminoaryl) aryltriazoles
IPC: C08F246/00
Filed: 1963-02-15
Abstract: The invention comprises 2-(o-aminophenyl)-2,1,3-benzotriazoles of formula <FORM:1037161/C2/1> where R is hydrogen or an acyl group free of acetylenic unsaturation and at least one of the groups (R11)m and (R1)n is a di-n-trivalen alkenylene group which forms together with the aromatic ring to which it is attached a condensed aromatic system containing up to 14 ring carbon atoms, the values of m and n for the groups forming the condensed system being 2, 3, or 4 and when R11 or R1 does not have this meaning they may represent an alkoxy or an electronegative group and in which case m or n may be 0, 1, 2, 3 or 4.  The compounds may be prepared by oxidizing o,o1-diaminoazobenzene in a nitrogen containing solvent, e.g. pyridine or ammonia, with an oxidizing agent such as cupric sulphate and chromium trioxide, or alternatively by treating dibenzo-1,3a,4,6a-tetraazapentalene with a reducing agent such as lithium, sodium, or potassium-aluminium hydrides, or lithium, sodium and potassium borohydrides in an inert medium such as tetrahydrofuran, tetrahydronaphthalene, decahydronaphthalene, pyridine and cyclohexane.  Alkoxy, acyl and electronegative groups are listed and examples describe the preparation of 2-(o-aminophenyl) - 2,1,3 - a ,b  - naphthotriazole and its benzamido derivative, and 2-(o-aminonaphthyl)-2,1,3-benzotriazole. The compounds are opaque to ultra-violet light and are suitable as stabilizers for dyes, and polymers.  Compounds with the acyl groups comprising a monoethylenically unsaturated acyclic hydrocarbon, may be homopolymerized or copolymerized to products with light resistance.ALSO:Photo-stabilizers for polymers and copolymers comprise 2 - (o - aminophenyl) - 2,1,3 - benzotriazoles of formula <FORM:1037161/C3/1> where R is hydrogen or an acyl group free of acetylenic unsaturation, and at least one of the groups (R11)m and (R1)n is a di- or trivalent alkenylene group which forms together with the aromatic ring to which it is attached, a condensed aromatic system containing up to 14 ring carbons, the values of m and n for said group(s) forming said condensed ring system being 2, 3 or 4 and where the group R11 or R1 which if present does not have this meaning they may represent an alkoxy or an electro-negative group and in which case m or n may be 0, 1, 2, 3 or 4 (see Division C2).  Natural, addition and condensation polymers, e.g. polyesters, polyamides, polycarbonates, and polymethanes; polyethylene, polypropylene, polystyrene, polyvinyl chloride, polyvinyl fluoride, polyvinylidene fluoride, polyvinyl acetate, propionate and butyrate, polyacrylonitrile, polymethylacylonitrile, polymethyl acrylate and methacrylate, copolymers of ethylene, copolymers of styrene, polyvinyl pyrrolidone, polyvinyl succinimide, polyvinyltrimethyl acetate; and nitrocellulose, cellulose acetate, propionate and butyrate and regenerated cellulose may be photo-stabilized. The benzotriazole may be added to a condensation polymerization as a chain terminator, and in the use with addition polymers, when the acyl group is unsaturated, it may be copolymerized with the polymer to be stabilized, or polymerized and added separately. Polyamides.-The triazoles having at least two COOH substituents may be condensed with diamines.