Patent GB-1016365-A (GB)
Title: New azolyl-thiophene derivatives, process for their preparation and their use
IPC: C08K5/45
Filed: 1963-11-27
Abstract: Azolyl-thiophene compounds of Formula (1) <FORM:1016365/C3/1> in which R1 is a benzene or naphthalene residue; R is a thiophene residue linked in position 2 with R1 and position 5 with the azole ring; X represents-O-,-S-,-NH-or -NA- in which A is an alkyl, alkenyl, hydroxyalkyl or cyanoalkyl group containing up to 4 carbon atoms or an aralkyl or carboxylacyl group; and R2 is a benzene or naphthalene residue linked to the azole ring as shown and carrying at least one carboxylic group (or a functionally converted carboxylic group retaining the <FORM:1016365/C3/2> group) linked directly to a carbon atom of the aromatic nucleus, are used for optically brightening synthetic fibres, particularly polyester fibres and polyamide fibres.  They may be added to the reaction mixtures before or during the polymerization leading to the formation of the polyesters and polyamides. Examples are given of the use of the new compounds in brightening (a) a polyester granulate of polyterephthalic acid ethylene glycol ester and (b) a polyamide prepared from hexamethylene diamine adipate.ALSO:The invention comprises azolyl-thiophene compounds of formula <FORM:1016365/C2/1> in which R1 is a benzene or naphthalene residue; R is a thiophene residue linked in position 2 with R1 and position 5 with the azole ring; X represents -O-, -S-, -NH-or -NA-, in which A is an alkyl, alkenyl, hydroxyalkyl or cyanoalkyl group containing up to 4 carbon atoms or an aralkyl or carboxylic acyl group; and R2 is a benzene or naphthalene residue linked to the azole ring as shown and carrying at least one carboxylic group (or a functionally converted carboxylic group retaining the >C = O group) linked directly to a carbon atom of the aromatic nucleus.  The nucleus R2 may carry other substituents, e.g. C1-C4 alkyl groups, in addition to the carboxylic group, and the nucleus R1 may also carry substituents, e.g. a halogen atom, a C1-C4 alkyl or alkoxy group.  The functionally converted carboxylic group attached to the residue R2 may be an amide, hydrazide or ester group. The new compounds may be prepared by reacting a carboxylic acid of formula R1-R-COOH at elevated temperature and preferably in the presence of a condensation catalyst with an amino compound of the formula <FORM:1016365/C2/2> and the residue R2 carrying an ester group which may be hydrolysed or converted into another functionally modified carboxylic acid group.  The new compounds are useful as optical brightening agents for synthetic fibres and are added to the reaction mixtures before or during polymerization or polycondensation. Examples are given of the preparation of compounds of the above general formula in which X is the group -O-; R1 is phenyl, 4-methoxy-phenyl, 4-methyl phenyl, or 4-chloro-2,5-di-methoxy phenyl and R2 is a phenyl residue carrying the group -COB, in which B is hydroxy, methoxy, N-morpholinyl, phenylamino, 2,5 - dimethoxy - 4 - chlorophenylamino -, b  - hydroxyethylamino -, allylamino -, NH2, allyloxy, benzyloxy, p-tolyloxy, isopropyloxy, 2 - ethylhexyloxy -, n - hexadecyloxy, and -OCH2CH2OCH2CH2OCH2CH2 CH2CH3.