Patent GB-656110-A (GB)
Title: Manufacture of brightening agents for animal and vegetable fibres
IPC: D06L4/60
Filed: 1948-10-30
Abstract: Compounds of the general formula <FORM:0656110/IV (b)/1> (where X indicates a direct carbon linkage or a divalent bridging member -O-, -NH-, or -alkylene-O-, Y is the acyl radical of a lower aryloxy fatty acid, and R is an alkyl or aryl radical which may be substituted as desired but not with sulphonic group), which are useful as brightening agents for wool or cellulose are prepared by introducing the R-X-CO-group into a 4,41-diaminostilbene-2,21-disulphonic acid which has been monoacylated with a lower aryloxy fatty acid radical. Alternatively, a 4,41-diaminostilbene-2,21-disulphonic acid mono-acylated by an R-X-CO-groups is acylated by treatment with a reactive derivative of a lower aryloxy fatty acid.  In examples: (1) the sodium salt of 4,41-diphenoxyacetaminostilbene-2,21-disulphonic acid is prepared by the action of phenoxy-acetyl chloride on 4,41 - diaminostilbene - 2,21 - disulphonic acid, and is used for brightening cellulose or wool fibres; (2) 4-phenylureido-41-phenoxyacetaminostilbene-2, 21-disulphonic acid is prepared by treating 4-nitro-41-aminostilbene-2,21-disulphonic acid with phenoxyacetyl chloride, reducing, and then reacting with phenyl isocyanate, and may be added to a household washing agent or used as a rinse; (3) 4-amino-41 - phenoxyacetaminostilbene-2,21-disulphonic acid is reacted with p - nitrophenoxyacetyl chloride, reduced, and reacted with ethyl chloroformate; (4) 4-phenoxyacetylamino-41-(211, 511-dichlorophenylureido)-stilbene-2,21-disulphonic acid is prepared by reacting 4,41-nitroaminostilbene-2,21-disulphonic acid with 2,5-dichlorophenyl isocyanate, reducing, and then reacting with phenoxyacetyl chloride; (5) 4,41-nitroaminostilbene-2,21-disulphonic acid is reacted with 3,4-dichlorophenylisocyanate, reduced, and acylated with 3,4-dichlorophenoxyacetyl chloride; (6) 4-amino-41-phenoxyacetaminostilbene-2,21-disulphonic acid is reacted with ethylchloroformate; (7) 4 - amino - 41 - phenoxyacetaminostilbene-2,21-disulphonic acid is reacted with the ethyl ester of phenylisocyanate-m-carboxylic acid; (8) 4,41-nitroaminostilbene-2,21-disulphonic acid is reacted with phenyl chloroformate, reduced, and acylated with phenoxyacetyl chloride; (9) 4,41-nitroaminostilbene-2,21-disulphonic acid is reacted with p-nitrobenzoyl chloride, reduced to the diamino compound and acylated with phenoxyacetyl chloride to give a product useful as an additive to soap powder; (10) 4-phenoxyacetylamino-41-phenylureido - stilbene - 2,21 - disulphonic acid is added to a washing agent containing soap, soda ash and water glass; and (11) to (60), other compounds of the above general formula are specified.  The Specification as open to inspection under Sect. 91 refers also to the compound of the above general formula when Y is C6H5OCH2CH2\t CH2CO- and -XR is -CONH-C4H6-CH3 (m).  This subject-matter does not appear in the Specification as accepted.ALSO:Compounds of the general formula <FORM:0656110/IV (c)/1> (where X indicates a direct carbon linkage or a divalent bridging member -O-, -NH-, or -alkylene-O-, Y is the acyl radical of a lower aryloxy fatty acid, and R is an alkyl or aryl radical which may be substituted as desired but not with sulphonic group), which are useful as brightening agents for wool or cellulose are prepared by introducing the R-X-CO-group into a 4,41-diaminostilbene-2,21-disulphonic acid which has been monoacylated with a lower aryloxy fatty acid radical. Alternatively, a 4,41-diaminostilbene-2,21-disulphonic acid mono-acylated by an R-X-CO-groups is acylated by treatment with a reactive derivative of a lower aryloxy fatty acid.  In examples: (1) the sodium salt of 4,41-diphenoxyacetaminostilbene-2,21-disulphonic acid is prepared by the action of phenoxy-acetyl chloride on 4,41-diaminostilbene 2,21-disulphonic acid, and is used for brightening cellulose or wool fibres; (2) 4-phenylureido-41-phenoxy-acetaminostilbene-2, 21-disulphonic acid is prepared by treating 4-nitro-41-aminostilbene-2,21-disulphonic acid with phenoxyacetyl chloride, reducing, and then reacting with phenyl isocyanate, and may be added to a household washing agent or used as a rinse; (3) 4-amino-41 - phenoxyacetaminostilbene - 2,21 - disulphonic acid is reacted with p-nitrophenoxy-acetyl chloride, reduced, and reacted with ethyl chloroformate; (4) 4-phenoxyacetylamino - 41 - (211,511 - dichlorophenylureido)-stilbene-2,21-disulphonic acid is prepared by reacting 4,41-nitroaminostilbene - 2,21 - disulphonic acid with 2,5-dichlorophenyl isocyanate, reducing, and then reacting with phenoxyacetyl chloride; (5) 4,41-nitroaminostilbene-2,21-disulphonic acid is reacted with 3,4-dichlorophenylisocyanate, reduced, and acylated with 3,4-dichlorophenoxyacetyl chloride; (6) 4 - amino - 41 - phenoxyacetaminostilbene-2,21-disulphonic acid is reacted with ethyl-chloroformate; (7) 4-amino-41-phenoxyacetaminostilbene-2,21-disulphonic acid is reacted with the ethyl ester of phenylisocyanate-m-carboxylic acid; (8) 4,41-nitroaminostilbene-2,21-disulphonic acid is reacted with phenyl chloroformate, reduced, and acylated with phenoxyacetyl chloride; (9) 4,41-nitroamino-stilbene-2,21-disulphonic acid is reacted with p-nitrobenzoyl chloride, reduced to the diamino compound and acylated with phenoxyacetyl chloride to give a product useful as an additive to soap powder; (10) 4-phenoxyacetylamino-41 - phenylureido - stilbene - 2,21 - disulphonic acid is added to a washing agent containing soap, soda ash and water glass and (11) to (60) other compounds of the above general formula are specified.  The Specification as open to inspection under Sect. 91 refers also to the compound of the above general formula when Y=C6H6OCH2 CH2CH2CO- and -XR=CONH-C5H4-CH3(m).  This subject-matter does not appear in the Specification as accepted.ALSO:Compounds of the general formula <FORM:0656110/III/1> (where X indicates a direct carbon linkage or a divalent bridging member -O-, -NH-, or -alkylene-O-, Y is the acyl radical of a lower aryloxy fatty acid, and R is an alkyl or aryl radical which may be substituted as desired but not with a sulphonic group), which are useful as brightening agents for wool or cellulose are prepared by introducing the R-X-CO-group into a 4,41-diaminostilbene-2,21-disulphonic acid which has been monoacylated with a lower aryloxy fatty acid radical. Alternatively, a 4,41-diaminostilbene-2,21-disulphonic acid mono-acylated by an R-X-CO-group is acylated by treatment with p  a reactive derivative of a lower aryloxy fatty acid.  In examples: (1) the sodium salt of 4,41-diphenoxyacetaminostilbene-2,21-disulphonic acid is prepared by the action of phenoxy-acetyl chloride on 4,41 - diaminostilbene - 2,21 - disulphonic acid, and is used for brightening cellulose or wool fibres; (2) 4-phenylureido-41-phenoxyacetaminostilbene-2, 21-disulphonic acid is prepared by treating 4-nitro-41-aminostilbene-2,21-disulphonic acid with phenoxyacetyl chloride, reducing, and then reacting with phenyl isocyanate, and may be added to a household washing agent or used as a rinse; (3) 4-amino-41 - phenoxyacetaminostilbene - 2,21 - disulphonic acid is reacted with p-nitrophenoxyacetyl chloride, reduced, and reacted with ethyl chloroformate; (4) 4 - phenoxyacetylamino-41 - (211,511-dichlorophenylureido)-stilbene-2, 21-disulphonic acid is prepared by reacting 4,41-nitroaminostilbene-2,21-disulphonic acid with 2,5-dichlorophenyl isocyanate, reducing, and then reacting with phenoxyacetyl chloride; (5) 4,41-nitroaminostilbene-2,21-disulphonic acid is reacted with 3,4-dichlorophenylisocyanate, reduced, and acylated with 3,4-dichlorophenoxyacetyl chloride; (6) 4-amino-41-phenoxyacetaminostilbene-2,21-disulphonic acid is reacted with ethylchloroformate; (7) 4-amino-41-phenoxyacetaminostilbene-2,21-disulphonic acid is reacted with the ethyl ester of phenylisocyanate-m-carboxylic acid; (8) 4,41-nitroaminostilbene-2,21-disulphonic acid is reacted with phenyl chloroformate, reduced, and acylated with phenoxyacetyl chloride; (9) 4,41-nitroaminostilbene-2,21-disulphonic acid is reacted with p-nitrobenzoyl chloride, reduced to the diamino compound and acylated with phenoxyacetyl chloride to give a product useful as an additive to soap powder; (10) 4-phenoxyacetylamino-41-phenylureido-stilbene-2, 21-disulphonic acid is added to a washing agent containing soap, soda ash and water glass; and (11) to (60) many other compounds of the above general formula are specified.  The Specification as open to inspection under Sect. 91 refers also to the compound of the above general formula when Y=C6H5OCH2CH2 CH2CO- and -XR=CONH-C6H4-CH3(m). This subject-matter does not appear in the Specification as accepted.