Patent GB-683895-A (GB)
Title: Whitening agents for organic materials
IPC: D06L4/65
Filed: 1949-10-13
Abstract: Fluorescent substantially colourless compounds of the general formula <FORM:0683895/IV (b)/1> wherein Ar stands for an aromatic radical linked to the triazole group by two neighbouring carbon atoms and G stands for an aromatic grouping which in combination with the two groups attached imparts substantivity whereas X stands for an aromatic radical which is linked to G by means of a heterocyclic system such as <FORM:0683895/IV (b)/2> <FORM:0683895/IV (b)/3> said compound carrying sulphonic acid groups, are prepared by diazotizing or tetrazotizing dehydrothiotoluidine sulphonic acid, benzidine or diaminostilbene disulphonic acid, coupling the diazo or tetrazo compound with 2-amino-naphthalene or one of its sulphonic acids or a substitution product thereof, or with an ester or arylide of b -aminocrotonic acid, and converting the ortho-amino azo compound thus obtained into a triazole.  Compounds specified are 4,41 - bis - (51 - sulphonaphtho - 11,21 : 4,5 - triaxolyl - 2) - stilbene - 2,21 - disulphonic acid or a salt thereof, 2-[41-(51-sulphonaphtho-11,21 : 4,5-triazolyl - 2) - phenyl] - 6 - methylbenzthiazole sulphonic acid or a salt thereof, and these may, if desired, be mixed with another fluorescent whitening agent with a faint reddish tint such as (stilbene - 4,41) - bis - (o  - phenyl - urea) - 2,21 disulphonic acid or a salt thereof.  The latter compound is obtained by reacting 1 mol. of 4,41 - diaminostilbene - 2,21 - disulphonic acid and 2 mols. of phenylisocyanate.  The Specification as open to inspection under Sect. 91 refers also to the compound obtained by tetrazotizing 4,41 p  - diaminostilbene - 2,21 - disulphonic acid, coupling with 2-amino-5-methoxynaphthalene-7-sulphonic acid or 2-amino-8-methoxynaphthalene-6-sulphonic acid and oxidizing with ammoniacal copper sulphate.  This subject-matter does not appear in the Specification as accepted.ALSO:Textile materials, paper, including photographic paper and wrapping paper for protecting substances sensitive to ultra-violet light, straw, wood, and other organic materials are given an improved white appearance by incorporating a fluorescent substantially colourless compound of the general formula <FORM:0683895/IV (c)/1> wherein Ar stands for an aromatic radical linked to the triazole group by two neighbouring carbon atoms and G stands for an aromatic grouping which in combination with the two groups attached imparts substantivity whereas X stands for an aromatic radical which is linked to G by means of a heterocyclic system such as <FORM:0683895/IV (c)/2> or <FORM:0683895/IV (c)/3> said compound carrying sulphonic acid groups (see Group IV (b)) and being substantive towards the said material. The compounds may also be added to soap, washing powders, starch and like laundering and finishing agents.  Compounds specified are 4,41 - bis - (51 - sulphonaphtho - 11,21 : 4,5 - triazolyl - 2) - stilbene - 2,21 - disulphonic acid [I] or a salt thereof, 2-[41-(51-sulphonaphtho - 11,21 : 4,5 - triazolyl - 2) - phenyl] - 6 - methylbenzthiazole sulphonic acid [II] or a salt thereof, and these may, if desired, be mixed with another fluorescent whitening agent with a faint reddish tint such as (stilbene4,41) - bis - (o  - phenyl - urea) - 2,21 - disulphoni acid [III] or a salt thereof.  The latter compound is obtained by reacting 1 mol. of 4,41-diaminostilbene - 2,21 - disulphonic acid and 2 mols. of phenylisocyanate.  In examples: (1) a fabric is treated with a liquor containing the compound [I], rinsed and dried-the compound [I] is made by tetrazotizing 4,41-diaminostilbene - 2,21 - disulphonic acid, coupling with 2 mols. of 1- (or 2-) aminonaphthalene-5-sulphonic acid and boiling with ammoniacal copper sulphate solution; (2) white goods are washed with a washing liquor containing sodium carbonate, a detergent, and the compound [II] which is made by diazotizing dehydrothiotoluidine sulphonic acid, coupling with 2-aminonaphthalene-5-sulphonic acid and boiling with alkaline chromate; (3) yellowish white paper is treated with a solution of the compound [I] or the compound may be added to the paper pulp; (4) yellowish nettle cloth is rinsed with a solution containing both compounds [I] and [III]; (5) white goods are washed with a liquor containing, besides the usual washing agents, a mixture of compounds [I] and [III]; and (6) cotton is dyed and then discharged with a Rongalite discharge paste which contains compound [I]-a similar white discharge effect is obtained if the compound [I] is added to the dyebath instead of the discharge paste.  The Specification as open to inspection under Sect. 91 refers also to the use of the compound obtained by tetrazotizing 4,41-diaminostilbene-2,21-disulphonic acid, coupling with 2-amino-5-methoxynaphthalene-7-sulphonic acid or 2-amino - 8 - methoxynaphthalene - 6 - sulphonic acid and oxidizing with ammoniacal copper sulphate.  It also includes an example in which wool is whitened by boiling with a solution containing compound [I] and sulphuric acid.  This subject-matter does not appear in the Specification as accepted.ALSO:Textile materials and other organic materials are given an improved appearance by incorporating a fluorescent substantially colourless compound of the general formula <FORM:0683895/III/1> wherein Ar stands for an aromatic radical linked to the triazole group by two neighbouring carbon atoms and G stands for an aromatic grouping which in combination with the two groups attached imparts substantivity whereas X stands for an aromatic radical which is linked to G by means of a heterocyclic system such as <FORM:0683895/III/2> said compound carrying sulphonic acid groups (see Group IV(b) and being substantive towards the said material. The compounds may also be added to soap, washing powders, starch and like laundering and finishing agents.  Compounds specified are 4.41-bis-(51-sulphonaphtho-11, 21 : 4.5-triazolyl-2-)-stilbene-2-, 21-disulphonic acid [I] or a salt thereof, 2-[41-(51sulphonaphtho-11, 21 : 4, 5-triazolyl-2)-phenyl]-6-methylbenzthiazole sulphonic acid [II] or a salt thereof, and these may if desired be mixed with another fluorescent whitening agent with a faint reddish tint such as (stilbene-4, 41) -bis-(p -phenyl-urea)-2, 21-disulphonic acid [III] or a salt thereof.  The latter compound is obtained by reacting 1 mol of 4, 41-diaminostilbene-2, 21disulphonic acid and 2 mols of phenylisocyanate.  In an example, white good are washed with a composition containing, besides the usual washing agents, a mixture of compounds [I] and [III].  The Specification as open to inspection under Sect. 91, refers also to the use of the compound obtained by tetrazotizing 4,41-diaminostilbene-2, 21-disulphonic acid, coupling with 2-amino-5-methoxynaphthalene-7-sulphonic acid or 2-amino-8-methoxynaphthalene-6-sulphonic acid and oxidizing with ammoniacal copper sulphate.  This subject matter does not appear in the Specification as accepted.ALSO:Textile materials and other organic materials are given an improved white appearance by incorporating a fluorescent substantially colourless compound of the general formula <FORM:0683895/V/1> wherein Ar stands for an aromatic radical linked to the triazole group by two neighbouring carbon atoms and G stands for an aromatic grouping which in combination with the two groups attached imparts substantivity whereas X stands for an aromatic radical which is linked to G by means of a heterocyclic system such as <FORM:0683895/V/2> said compound carrying sulphonic acid groups (see Group IV (b)) and being substantive towards the said material.  The compounds may also be added to starch and like laundering and finishing agents.  Compounds specified are 4,41-bis-(51-sulphonaphtho-11,21:4, 5-triazolyl-2)-stilbene-2,21-disulphonic acid or a salt thereof, 2-[41-(51-sulphonaphtho-11,21:4, 5-triazolyl -2)-phenyl]-6-methylbenzthiazole sulphonic acid or a salt thereof, and these may if desired be mixed with another fluorescent whitening agent with a faint reddish tint such as (stilbene-4,41)-bis-(o -phenyl-urea)-2,21-disulphonic acid or a salt thereof.  The latter compound is obtained by reacting 1 mol of 4,41-diaminostilbene-2,21 disulphonic acid and 2 mols of phenylisocyanate.  The Specification as open to inspection under Sect. 91 refers also to the use of the compound obtained by tetrazotizing 4,41-diaminostilbene-2,21-disulphonic acid, coupling with 2-amino-5-methoxynaphthalene - 7 - sulphonic acid or 2-amino-8-methoxynaphthalene-6-sulphonic acid and oxidizing with ammoniacal copper sulphate.  This subject-matter does not appear in the Specification as accepted.