Patent GB-1033385-A (GB)
Title: Di-arylene azolyl styrene compounds and their use as optical brightening agents
IPC: C07D263/62
Filed: 1963-03-28
Abstract: Di-arylene azolyl styrene compounds of formula <FORM:1033385/C4-C5/1> in which A and A1 are the same or different and are substituted or unsubstituted benzene or naphthalene nuclei fused to the adjacent azolyl ring; the benzene ring b  may carry substituents; X and X1 are the same or different and each represents an oxygen or sulphur atom or one of them may represent a group -NR- in which R is a hydrogen atom or an alkyl, aryl or aralkyl group; and Y and Y1 are the same or different and are hydrogen or halogen atoms or alkyl groups; are used as optical brightening agents in conjunction with soaps and detergents, e.g. a polyethylene glycol ether of aliphatic higher alcohols, and also with a bleaching agent, e.g. sodium hypochlorite, for the treatment of polyester or polyether materials, e.g. sheets, fabrics or fibres.ALSO:The invention comprises di-arylene azolyl styrene compounds of formula <FORM:1033385/C2/1> in which A and A1 are the same or different and are substituted or unsubstituted benzene or naphthalene nuclei fused to the adjacent azolyl ring; the benzene ring B may carry substituents; X and X1 are the same or different and each represents an oxygen or sulphur atom or one of them may represent a group -NR- in which R is a hydrogen atom or an alkyl, aryl or aralkyl group; and Y and Y1 are the same or different and are hydrogen or halogen atoms or alkyl groups, the compounds being free of water-solubilizing groups and chromogenic groups and the groups A, A1 and B being free from substitution by alkyl groups containing 4 or more carbon atoms. Preferred compounds are those of formula <FORM:1033385/C2/2> in which X, X1, Y and Y1 are as defined above and R1, R2, R3, R4, R5 and R6 may be the same or different and are hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, cycloalkyl, aralkyl, aryl, nitro or cyano.  The new compounds may be prepared as follows:-(a) a diazonium compound of a 2-(p-aminoaryl)arylene azole of formula <FORM:1033385/C2/3> is coupled with an a ,b  unsaturated dicarboxylic acid of formula HOOC-CY = CY1-COOH (or the anhydride thereof) and the product, which is a cinnamic acid derivative of formula <FORM:1033385/C2/4> is coupled with a diazonium compound of an amine of formula <FORM:1033385/C2/5> (b) the cinnamic acid derivative referred to in (a) is condensed with an amine of formula <FORM:1033385/C2/6> (c) a b -(arylene-2-azolyl)-acrylic acid of formula <FORM:1033385/C2/7> is coupled with a diazonium compound of a 2-(p-aminoaryl) arylene azole as defined in (a); and (d) compounds in which the 2 arylene azolyl groups are the same, may be prepared by condensing a 4-carboxycinnamic acid of formula <FORM:1033385/C2/8> in which R7 is H or a C1-C3 alkyl group with an amine of formula <FORM:1033385/C2/9> in which X is oxygen or sulphur.  The new diarylene azolyl compounds and their sulphonamide and sulphonic acid derivatives may be used as optical brightening agents.ALSO:Di-arylene azolyl styrene compounds of formula <FORM:1033385/C3/1> in which A and A1 are the same or different and are substituted or unsubstituted benzene or naphthalene nuclei fused to the adjacent azolyl ring, the benzene ring B may carry substituents; X and X1 are the same or different and each represents an oxygen or sulphur atom or one of them may represent a group -NR- in which R is a hydrogen atom or an alkyl, aryl or aralkyl group, and Y and Y1 are the same or different and are hydrogen or halogen atoms or alkyl groups, are used as optical brightening agents for polymeric materials. The polymeric materials may be in the form of filaments, yarns, threads, films, sheets, foils or plates and may be, for example, polyfines such as polypropylene, polyethylene and ethylene-propylene copolymers or may be polyesters derived from dicarboxylic acids and dihydric alcohols, e.g. polyethylene glycol terephthalate.  The styrene derivatives may be incorporated in the polymeric materials before or after shaping them.ALSO:Di-arylene azolyl styrene compounds of formula <FORM:1033385/D1-D2/1> in which A and A1 are the same or different and are substituted or unsubstituted benzene or naphthalene nuclei fused to the adjacent azolyl ring; the benzene ring B may carry substituents; X and X1 are the same or different and each represents an oxygen or sulphur atom or one of them may represent a group -NR- in which R is a hydrogen atom or an alkyl, aryl or aralkyl group; cdY and Y1 are the same or different and are hydrogen or halogen atoms or alkyl groups; are used as optical brightening agents for polyester or polyolefin textile materials or fibres.