Patent GB-1111986-A (GB)
Title: Optical brighteners
IPC: D06L4/657
Filed: 1965-09-24
Abstract: As optical brighteners, use is made of pyrazoline sulphones of the formula <FORM:1111986/C3/1> in which R denotes an aryl radical, Y denotes oxygen or sulphur and R1 denotes an alkyl, aralkyl or phenyl radical, any of which may be substituted by a hydroxy, alkoxy or carboxy group, a carboxy group esterified with an alkanol of 1-4 carbon atoms, or a dialkylamino group which may be a compound in which the two alkyl groups, together with the nitrogen atom, form a 5- or 6-membered heterocyclic ring or may form part of a quaternary trialkylammonium group (see Division C2).  The pyrazoline derivatives may be added to spinning or moulding masses of synthetic high polymers, e.g. vinyl or vinylidene chloride, polyethylene, polypropylene or polyamides, from which filaments, foils and other shaped structures are to be made.  In Example 10, a polyamide melt is made from caprolactam and extruded, a pyrazoline derivative as defined above being included in the melt.ALSO:As optical brighteners in detergent compositions, use is made of pyrazoline sulphones of the formula <FORM:1111986/C4-C5/1> in which R denotes an aryl radical, Y denotes oxygen or sulphur and R1 denotes an alkyl, aralkyl or phenyl radical, any of which may be substituted by an hydroxy, alkoxy or carboxy group, a carboxy group esterified with an alkanol of 1-4 carbon atoms, or a dialkylamino group which may be a compound in which the two alkyl groups, together with the nitrogen atom, form a 5- or 6-membered heterocyclic ring or may form part of a quaternary trialkylammonium group (see Division C2).  Detergent compositions containing the compounds may contain also oxidizing bleaching agents, e.g. perborates, or reducing bleaching agents, e.g. sodium dithionate or sodium boron hydride.  In examples 2 and 6, a bleached protein or polycaprolactam fabric is treated with a detergent composition of specified constitution, in each example a pyrazoline derivative as defined above being included in the composition.ALSO:The invention comprises pyrazoline derivatives of the formula <FORM:1111986/C2/1> in which R denotes an aromatic radical, preferably a p-chlorophenyl radical, Y denotes oxygen or sulphur and R1 denotes an alkyl, aralkyl or phenyl radical, any of which may be substituted by a hydroxy, alkoxy or carboxy group, a carboxy group esterified with an alkanol of 1-4 carbon atoms or a dialkylamino group which may be a compound in which the two alkyl groups, together with the nitrogen atom, form a 5- or 6-membered heterocyclic ring or may form part of a quaternary trialkylammonium group.  The compounds may be preparted by addition of a vinylsulphone compound of the formula <FORM:1111986/C2/2> to an aliphatic, araliphatic or aromatic hydroxy or mercapto compound.  A number of suitable vinylsulphone compounds and hydroxy or mercapto compounds are specified, and examples are given of the addition of 1-(41-vinylsulphonylphenyl) - 3 - p - chlorophenyl - D 2 - pyrazoline to (a) thioglycollic acid, (b) thiosalicylic acid methyl ester, (c) N-b -hydroxyethylpiperidine and (d) 1 - dimethylaminopropanol-2, the product of this example being optionally quaternized by treatment with dimethyl sulphate.  An alternative method of preparing the pyrazoline derivatives comprises the reaction of 4-(b -alkoxy-, aralkoxy- or phenoxy-ethylsulphonyl)-phenylhydrazines or the corresponding thioethers with o -chloropropiophenone and substitution products thereof, but no examples of this method are given. The products are useful as optical brighteners (see Divisions C3, C5 and D1).ALSO:As optical brighteners, use is made of pyrazoline sulphones of the formula <FORM:1111986/D1-D2/1> in which R denotes an aryl radical, Y denotes oxygen or sulphur and R1 denotes an alkyl, aralkyl or phenyl radical, any of which may be substituted by a hydroxy, alkoxy or carboxy group, a carboxy group esterified with an alkanol of 1-4 carbon atoms, or a dialkylamino group which may be a compound in which the two alkyl groups, together with the nitrogen atom, form a 5- or 6- membered heterocyclic ring or may form part of a quaternary trialkylammonium group (see Division C2).  The pyrazoline derivatives may be used in aqueous or organic solvent solution or in dispersion for the treatment of organic fibrous materials, e.g. cotton, cellulose acetate, wool, polyamides or polyacrylonitrile or its co-polymers.  The compounds may be used alone or in association with other textile-treating media, e.g. detergent, dyeing or antistatic compositions.  In examples 1, 4 and 7, a bleached protein, polycaprolactum or polyacrylonitrile fabric is brightened.  In example 3, a bleached protein fabric is dyed with a basic dyestuff of specified constitution.  In examples 5 and 8, a bleached polycaprolactum or polyacrylonitrile fabric is given an antistatic treatment with a commercial antistatic agent or with a polyethylene glycol-epichlorohydrin reaction product after-treated with ammonia. In example 9, a bleached cellulose fabric is given a soft handle by impregnation with a polyvinyl acetate-paraffin dispersion.  In each example, a pyrazoline derivative as defined above is included in the treating composition.