Patent GB-1031548-A (GB)
Title: Pyrazine-type optical brightening agents and their use
IPC: C07D241/26
Filed: 1964-10-28
Abstract: Novel 3,5-diamino-pyrazine-2,6-dicarboxylic acid derivatives of the formula <FORM:1031548/C2/1> wherein A represents -SO2- or -CO-, X represents -N(R)- or, if A is -CO-, may also be -O-, and R is hydrogen or C1- 6 alkyl, Y represents a divalent aliphatic radical containing at least 2 carbon atoms, or a cycloalkylene radical, R1 and R11 separately each represent an alkyl, cycloalkyl or aralkyl radical, or together form with the nitrogen atom to which they are attached a heterocyclic ring, and the ring B may contain halogen, C1- 6 alkyl or C1- 6 alkoxy groups, and their corresponding quaternary compounds of the formula <FORM:1031548/C2/2> wherein R111 represents a substituted or unsubstituted alkyl, cycloalkyl or aralkyl radical and An represents an anion, are prepared by reacting compound A with compound B <FORM:1031548/C2/3> and, if desired, quaternating the product with an alkylating cycloalkylating or aralkylating agent. Alternatively, compound C is reacted with compound D C. <FORM:1031548/C2/4> D. <FORM:1031548/C2/5> and, if desired, the product is quaternated with an alkylating, cycloalkylating or aralkylating agent.  1 - Aminobenzene - 3 - sulphonic acid - (g -dimethylaminopropyl) - amide, 1 - aminobenzene-3 - carboxylic acid - (g  - dimethylaminopropyl)-amide and 1 - aminobenzene - 4 - carboxylic acid - (b  - diethylaminoethyl - ester are prepared by reduction of the corresponding nitro compounds.  1 - Nitrobenzene - 3 - sulphonic acid - (g -dimethylaminopropyl) - amide and 1 - nitro-benzene - 3 - carboxylic acid - (g  - dimethylaminopropyl) - amide are prepared by condensing g -dimethylaminopropylamine with the corresponding acid.  1 - Nitrobenzene - 4 - carboxylic acid - (b  - diethylaminoethyl) - ester is prepared by reacting 1 - nitrobenzene - 4 - carboxylic acid chloride with b -diethylaminoethanol.  3,5 - Bis - methylamino - pyrazine - 2 - carboxylic acid methylamide - 6 - carboxylic acid chloride is prepared by reacting the corresponding acid with thionyl chloride.  An acid chloride of the formula <FORM:1031548/C2/6> is prepared by reacting 3,5-bis-methylaminopyrazine - 2 - carboxylic acid methylamide-6 - carboxylic acid chloride with 1 - amino-benzene - 3 - carboxylic acid to form a carboxylic acid which is then converted to the acid chloride.ALSO:Textile materials such as polymerized and copolymerized acrylonitrile fibres, yarns and staple fibre fabrics, nylon fabrics, cellulose-2, 5-acetate and bleached triacetate charmeuse are brightened by treatment with aqueous solutions of 3, 5-diamino-pyrazine-2, 6-dicarboxylic acid derivatives of the formula:- <FORM:1031548/D1-D2/1> wherein A represents -SO2- or -CO-, X represents -N(R)- or, if A is -CO-, may also be -O-, and R is hydrogen or C1-6 alkyl, Y represents a divalent aliphatic radical containing at least 2 carbon atoms, or a cycloalkylene radical, R1 and R11 separately each represent an alkyl, cycloalkyl or aralkyl radical, or together form with the nitrogen atom to which they are attached a heterocyclic ring, and the ring B may contain halogen, C1-6 alkyl or C1-6 alkoxy groups, or their corresponding quaternary compounds of the formula:- <FORM:1031548/D1-D2/2> wherein R111 represents a substituted or unsubstituted alkyl, cycloalkyl or aralkyl radical and An represents an anion. The treatment may take the form of exhaustion from baths or impregnation by foularding, optionally followed by development using a hot moist treatment such as steaming.  The aqueous treatment solutions may be acid, neutral or weakly alkaline and may be washing liquors containing anionic or non-ionogenic washing agents usual in laundering.  Specified further ingredients are acetic, oxalic and formic acids, sodium sulphate, sodium tripolyphosphate, fatty alcohol polyglycol ethers, nonyl phenol/ethylene oxide condensation products, the bis-(b -hydroxy-ethyl)-amine salt of coconut oil fatty acid and coconut oil fatty acid -N, N bis-(b -hydroxy-ethyl)-amide.