Patent GB-978547-A (GB)
Title: New thiophene derivatives, process for their preparation and their use
IPC: C07D413/14
Filed: 1963-07-26
Abstract: The invention comprises thiophene derivatives of the general formula: <FORM:0978547/C1/1> in which A represents a benzene nucleus in which two visual carbon atoms are members of the oxazole ring, R is a thiophene residue bound in positions 2 and 5 to the oxazole rings. The aralkyl radicals may have up to three carbon atoms in the alkyl portion and the thiophene ring may be substituted by methyl groups. The compounds are prepared by heating a compound of formula <FORM:0978547/C1/2> in the molecular ratio of 2:1 with a compound HOOC-R-COOH, or a functional derivative thereof, preferably in the presence of a condensation catalyst.  The reaction is preferably carried out in an inert gas, e.g. nitrogen at 160 DEG -260 DEG C. and in a high-boiling solvent. The catalyst may be boric acid, zinc chloride, paratoluenesulphonic acid, or a polyphosphoric acid, e.g. pyrophosphoric acid.  The compounds are used as optical brightening agents.ALSO:Polymers are optically brightened by incorporating therein a compound of the general formula: <FORM:0978547/C3/1> in which A represents a benzene nucleus in which two vicinal carbon atoms are members of the oxazole ring, R is thiophene residue bound in positions 2 and 5 to the oxazole ring. Polymers include polyethyleneglycol terephthalate, polyhexamethylene -diamine adipate, alkyd resins polyvinyl chloride, polystyrene, polyvinylidene chloride, polyvinyl alcohol, polyvinyl esters of organic acids.ALSO:Detergent compositions contain, as optical brightener a compound of the general formula <FORM:0978547/C4-C5/1> in which A represents a benzene nucleus in which two vicinal carbon atoms are members of the oxazole ring, R is a thiophone residue bound in positions 2 and 5 to the oxazole ring.  Suitable detergents are soaps, salts of sulphonate products, e.g. sulphonated benzimidazoles substituted on the carbon atom 2 by higher alkyl radicals, salts of monocarboxylic acid esters of 4-sulphophthalic acid with higher fatty alcohols, salts of fatty alcohol sulphonates, alkylarylsulphonic acids or condensation products of higher fatty acids with aliphatic hydroxysulphonic or aminosulphonic acids, polyglycol ethers derived from ethylene oxide and higher fatty alcohols, alkyl phenols or fatty amines.ALSO:Synthetic fibres, as staple fibres, monofilaments, hanks or fabrics are optically brightened by using a compound of the general formula <FORM:0978547/D1-D2/1> in which A represents a benzene nucleus in which two vicinal carbon atoms are members of the oxazole ring, R is a thiophane residue bound in positions 2 and 5 to the oxazole ring.  The compounds are suspended in aqueous medium, which may be neutral, weakly alkaline, or acidic.  The treatment bath may also contain dispersing agents, e.g. soaps, polyglycol ethers of fatty alcohols, fatty amines or alkyl phenols, cellulose sulphite waste liquor or condensation products of optionally alkylated naphthalenesulphonic acids with formaldehyde.  The fibres may be from cellulose esters, e.g. cellulose propionate, or cellulose di- or tri-acetate, polyamides, polyesters or polyolefines.