Patent GB-933042-A (GB)
Title: 3-phenyl-7-hydroxy-coumarin compounds
IPC: D06L3/12
Filed: 1961-02-22
Abstract: Brightening agents for polyacrylonitrile fibres comprising 3-phenyl-7-hydroxy coumarin compounds of formula, <FORM:0933042/IV(a)/1> in which R represents a hydrogen atom or an alkyl containing up to 4 carbon atoms, and R1 is a hydrogen atom or an alkyl, hydroxyalkyl, alkoxyalkyl, haloalkyl, cyanoalkyl, carboxyalkyl, sulphoalkyl, alkenyl, aralkyl, aryl, arylketoalkyl, acyl, or carbamyl radical or the groups, <FORM:0933042/IV(a)/2> wherein R2 and R3 represent hydrogen atoms or unsubstituted or substituted alkyl, cycloalkyl, alkenyl, or aralkyl radicals, and R4, R5, R6 are the same or different unsubstituted or substituted alkyl, cycloalkyl, alkenyl, or aralkyl radicals whereas X represents the bivalent residue of an aliphatic hydrocarbon, and Y an inorganic or organic acid residue, and wherein any of the aromatic rings in the compound may be substituted by other than nitro groups (Group IV(b)) are included in the spinning solution.  In an example 1 part polyacrylonitrile in 8 parts of dimethyl formamide with 1 part of brightening agent is added as a stock solution to the spinning solution to give a proportion of 0,25% by weight of brightening agent or the polyacrylonitrile.ALSO:The invention comprises 3-phenyl-7-hydroxy-coumarin compounds of formula <FORM:0933042/IV(a)/1> where R represents a hydrogen atom or an alkyl radical with up to 4 carbon atoms, and R1 a hydrogen atom or an alkyl, hydroxyalkyl, alkoxy-alkyl, haloalkyl, cyanoalkyl, carboxyalkyl, sulphoalkyl, alkenyl, aralkyl, aryl, arylketoalkyl, acyl, or carbamyl radical or the grouping <FORM:0933042/IV(a)/2> , <FORM:0933042/IV(a)/3> or <FORM:0933042/IV(a)/4> or <FORM:0933042/IV(a)/5> p  where R2 and R3 represent hydrogen atoms or unsubstituted or substituted alkyl, cycloalkyl, alkenyl or aralkyl radicals and R4, R5 and R6 are the same or different unsubstituted or substituted alkyl, cycloalkyl, alkenyl or aralkyl radicals, X represents the bivalent residue of an aliphatic hydrocarbon with preferably 1-4 carbon atoms and Y represents an inorganic or organic acid residue, and the aromatic rings may contain further substituents except nitro groups.  The compounds are suitable as optical brightening agents and are prepared by reacting a 2,4-dihydroxy-benzaldehyde or substitution product thereof with phenyl acetic acid or a functional derivative or substitution product thereof.  Examples describe the preparation of 3-phenyl-7-acetoxy-, 3-phenyl-7-hydroxy-, 3-phenyl-7-methoxy, 3-phenyl-7-ethoxy coumarins, sodium 3-phenyl-coumarin 7-butoxy sulphonate and sodium 3-phenyl coumarin 7-methoxy sulphonate, butyl, isopropyl, allyl, ethylane and benzyl alkylation products of 3-phenyl-7-hydroxy coumarin, 3-phenyl-7-(21-diethylaminoethoxy)-coumarin, 3-(p-methylphenyl)-7-hydroxy, and methoxy-, coumarin, 3-phenyl-5-methyl-7-hydroxy-, methoxy, and acetoxy-, coumarin, 3-phenyl-6-methyl-7-hydroxy- and acetoxy-coumarin, 3-(41-chlorophenyl)-7-hydroxy-, methoxy- and acetoxy coumarin, 3-phenyl-5,7-dihydroxy-, and dimethoxy coumarin, 3-phenyl-7-methoxy- and ethoxy coumarin, 3-(21,41-dimethylphenyl)-7-methoxy, 3-(41-carboxyphenyl)-7-acetoxy coumarin, 3-(41-ethylphenyl)- 7-hydroxy- and methoxy-coumarin, 3-(41- isopropylphenyl)7-acetoxy coumarin, 3-(31,41- tetramethylenephenyl)-7- methoxycoumarin, 3-(41-carbomethoxy phenyl)-7-methoxy coumarin and the compound obtained by reacting 2,4-dihydroxy benzaldehyde with sodium phenylene-1,4-diacetate and acetic anhydride, <FORM:0933042/IV(a)/6> and their use as brightening agents by the treatment of fibres, e.g. polyamide, cellulose acetate, polyacrylonitrile, polyester and polyurethane fibres, woollen fabric, or by the addition to a spinning solution of, for example, polyacrylonitrile.ALSO:Brightening agents for fibres, threads, films, and woven materials of wool, cellulose esters and synthetic polymers such as polyamides, polyacrylonitrile, polyesters and polymethanes comprise 3-phenyl-7-hydroxy-coumarin compounds of general formula <FORM:0933042/IV(a)/1> in which R represents a hydrogen atom or alkyl radical with up to 4 carbon atoms, and R1 is a hydrogen atom or an alkyl, hydroxyalkyl, alkoxyalkyl, haloalkyl, cyanoalkyl, carboxyalkyl, sulphoalkyl, alkenyl, aralkyl, aryl, arylketoalkyl acyl, or carbamyl radical or the groups <FORM:0933042/IV(a)/2> R2 and R3 represent hydrogen atoms or unsubstituted or substituted alkyl, cycloalkyl, alkaryl, or aralkyl radicals, and R4, R5 and R6 are the same or different, unsubstituted or substituted alkyl, cycloalkyl, alkenyl or aralkyl radicals, X represents the bivalent residue of an aliphatic hydrocarbon, and Y stands for an inorganic or organic acid residue and the aromatic rings may contain further substituents other than nitro groups (see Group IV(b)).  Solutions in water or organic solvents or aqueous dispersions may be used for the treatment and examples are given which include, in addition to the brightening agents, oleyl-alcohol sulphonate, oxalic acid and sodium chlorite, or formic acid.