Patent GB-835819-A (GB)
Title: New dyestuffs of the anthraquinone series
Inventor: LODGE FRANK
IPC: C09B1/60
Filed: 1957-10-04
Abstract: Alcohols of the formula HO-CH2-CH2-Y, where Y is beta-aryloxyethoxy, beta-arylthioethoxy, beta-N-arylaminoethoxy, beta-N-aryl - N - alkylaminoethoxy, beta - aryloxyethylthio, beta-arylthioethylthio, beta - N-arylaminoethylthio or beta - N - aryl - N - alkylaminoethylthio are made by condensing the benzoates of beta - chloro - beta1 - hydroxy-diethylether or beta-chloro-beta1-hydroxy-di-ethyl sulphide with the sodium salt of a phenol or thiophenol or an arylamine or an N-aryl-alkylamine and hydrolysing the esters formed with aqueous sodium hydroxide. Alcohols of the formula HO-CH2-CH2-Y, where Y is beta-amyl sulphonylethoxy, betaaryloxyethylsulphonyl, betaarylsulphonylethylsulpohonyl, beta - N - arylaminoethylsulphonyl or beta - N - aryl - N - alkylaminoethylsulphonyl are made by oxidizing the corresponding thio compounds in acetic acid solution with hydrogen peroxide.  Alcohols of the formula HO-CH2-CH2-Y, where Y is beta-arylsulphonylethylthio are made by condensing the sodium salt of thioglycol with an aryl beta-chlorethylsulphone.ALSO:The invention comprises dyestuffs of the formula <FORM:0835819/IV(c)/1> where X is oxygen or sulphur, Z is a hydroxyl or primary amino group, Y is chlorine or bromine, or an aryl, aryloxy, arylthio, arylsulphonyl, -O.CH2CH2R, -SCH2CH2R or -SO2-CH2CH2R radical where R is a chlorine or bromine atom or a hydroxy, aryloxy, arylthio, arylsulphonyl, b -hydroxyethoxy, b -chloroethoxy, b -bromoethoxy, b -aryloxyethoxy, b -arylthioethoxy, b -arylamino or b -N-aryl-N-alkylamino group, provided that Y is not chlorine or bromine when X is sulphur.  The invention also comprises processes for making the dyestuffs of the above general formula where X is oxygen and Y has the values aryl, aryloxy, arylthio, arylsulphonyl, -OCH2CH2R1 -SCH2CH2R or -SO2CH2CH2R where R i a hydroxy, aryloxy, arylthio, arylsulphonyl, b -hydroxyethoxy, b -aryloxyethoxy, b -arylamino or b -N-aryl-N-alkylamino group by reacting an alcohol of the formula HOCH2CH2Y with a 1-amino-4-amino- or -hydroxy-anthraquinone containing in the 2-position an aryloxy group, a halogen atom or a sulphonic acid group, provided that when the latter is present the reaction is conducted in the presence of sodium or potassium hydroxide.  The invention further comprises processes for making the dyestuffs of the above formula where X is sulphur and Y is aryl, aryloxy, arylthio, arylsulphonyl, -OCH2CH2R, -SCH2CH2R or -SO2CH2 CH2R where R is chlorine, bromine, hydroxy, aryloxy, arylthio, arylsulphonyl, b -hydroxy-ethoxy, b -chloroethoxy, b -bromoethoxy, b -aryloxyethoxy, b  - arylthioethoxy, b  - N - arylamino, or b -N-aryl-N-alkylamino group, by reacting a halogen compound of the formula Ha1CH2CH2Y with 1 - amino - 2 - mercapto4 - amino - or - hydroxy - anthraquinone, and for making dyestuffs of the above general formula where Y is chlorine or bromine or R is chlorine or bromine or a b -chloro- or b -bromoethoxy group by reacting a dyestuff of the above formula where X is oxygen or sulphur and R is hydroxy or b -hydroxyethoxy or wherein X is oxygen and Y is hydroxy with a chlorinating or brominating agent, and for making dyestuffs of the above general formula where Y contains an aryloxy or arylthio residue by reacting a dyestuff of the above formula where Y contains a b -chloroethyl or b -bromoethyl group or Y is a halogen atom with an aromatc hydroxy or thio compound.  Examples are given.  Aqueous dispersions of one or more of the dyestuffs are made by milling them with water and a dispersing agent such as disodium methylene bis - (naphthalene - 2 - sulphonate) and may be dried to form dispersible powders.  The dispersions are used to dye acetate rayon, cellulose triacetate and polyethylene terephthalate fibres.  The dyestuffs colour acetate rayon, cellulose triacetate and artificial fibres such as those of polyethylene terephthalate red to bluish red shades and may be used in fibres which are heat set.  The Provisional Specification also relates to dyestuffs of the above general formula where X is sulphur when Y is chlorine or bromine and where X is oxygen or sulphur and Y is -OCH2CH2R, -SCH2CH2R or -SO2CH2 CH2R where R is alkoxy or beta-alkoxyethoxy.