Patent GB-923162-A (GB)
Title: Process for dyeing, printing and/or optical brightening of textile materials and dye preparations therefor
Inventor: LUETZEL GERHARD
IPC: C09B62/443
Filed: 1961-10-31
Abstract: Compounds of the formula:  <FORM:0923162/IV(a)/1> are obtained from hexahydro-1,3,5-tri-(b  -chloropropionyl)-s-triazine by the action of tertiary amines such as pyridine, quinoline, N-methylimidazole or N-vinylimidazole.  Polyamides are obtained by reaction of 2 moles acrylic acid chloride with 1 mole of ethylene, propylene, butylene or hexamethylene diamine or 1,4-diaminobenzene-2-sulphonic acid, or by reaction of 3 moles of acrylic acid chloride with 1 mole of diethylene or dipropylene triamine, or by reaction of 4 moles acrylic acid chloride with 1 mole of triethylene tetramine. Alternatively instead of acrylic acid chloride the following chlorides may be used: b -chloropropionyl, b -sulphato-propionic acid, b -methoxypropionic acid, b -phenoxypropionic acid, b -(4-chlorothiophenyl)-propionic acid or b -phenylsulphone propionic acid chloride.  Those compounds containing the b -chloro-propionyl radical may be quaternised with a tertiary amine.  Methylene-bis-acrylamide of the formula: <FORM:0923162/IV(a)/2> is obtained by reaction of 2 moles acrylamide with 1 mole formaldehyde.  The above compound may be converted into cyclic compounds with dialdehydes, e.g. with glyoxal to a compound of the formula:  <FORM:0923162/IV(a)/3>ALSO:Textile materials are dyed, printed and/or optically brightened in the presence of an alkaline agent with (a) a dye or optical brightener having one or more reactive hydrogen atoms preferably attached by way of N, O or S atoms or which is capable of making such hydrogen atoms available during the process and (b) a polyfunctional colourless non-fluorescent compound which bears two or more CH2 = CH-CO-groups attached through nitrogen or which is capable of forming such groups during the process.  The textile materials may be of acrylic polymers, linear aromatic polyesters, polyamides or especially of cellulosic materials such as cotton or rayon.  The alkaline agents specified are sodium and potassium hydroxide, carbonate and bicarbonate, disodium and trisodium phosphate.  The dyes or brighteners (a) may bear 1-11 reactive H atoms in the form of 1 DEG  or 2 DEG  amino groups, sulphonic acid amide, alkylamide and arylamide groups, carboxylic acid amide and alkylamide groups, hydroxyl and sulphydryl groups but particularly -alkylene-OH, -alkylene-NH2, -SO2-NH2, -CH2CH2-OH, -CH2CH2-NH2, -SO2-NH-CH2CH2-OH and -SO2-NH-CH3 groups.  Dyestuffs containing methylene ether and ester groups which are converted into methylol groups during the process are also suitable.  The dyes may be water-soluble or insoluble and are preferably of low substantivity but may be of the reactive type.  (a) and (b) are said to react in the manner of the Michael reaction.  The specified compounds (b) are: hexahydro-1, 3, 5-triacryloyl-s-triazine obtainable by reaction of acrylonitrile and formaldehyde, hexahydro-1, 3, 5-tri-(p-chloropropionyl)-s-triazine and its derivatives quaternated with pyridine, quinoline, N-methylimidazole or N-vinylimidazole, the reaction products of 2 moles acrylic acid chloride with 1 mole ethylene, propylene, butylene or hexamethylene diamine or 1, 4-diaminobenzene-2-sulphonic acid, the reaction products of 3 moles acrylic acid chloride with 1 mole of diethylene or dipropylene triamine and the reaction product of 4 moles acrylic acid chloride with 1 mole of triethylene tetramine. Instead of acrylic acid chloride in the above products there may be used the following acyl chlorides: b -chloropropionyl, b -sulphatoethylpropionic acid, b -methoxypropionic acid, b -phenoxypropionic acid, b -(4-chlorothio-phenyl)-propionic acid or b -phenylsulphone-propionic acid chloride.  Those compounds containing the b -chloropropionyl radical may be quaternized as above.  Also suitable are methylene-bis-acryloylamide obtainable by reaction of 2 moles acrylamide with 1 mole formaldehyde and its condensation product with glyoxal of the formula <FORM:0923162/IV(a)/1> Fixation may be accomplished at room temperature but preferably at 70 DEG -150 DEG C. by steaming or dry heating for about 5-10 minutes.  (a) and (b) may be applied in either sequence but are preferably applied simultaneously from a single bath or paste also containing the alkaline agent by means of jiggers, vats, winch becks, high temperature dyeing apparatus or especially by padding or printing. Resin finishing may be carried out simultaneously.  Compounds (b) may be used together with dispersing agents and/or protective colloids as aqueous solutions or dispersions or as solutions in water miscible solvents such as dimethylformamide (preferred), dimethylacetamide, N-methyl-2-pyrrolidone, glycol ethyl ether, tetrahydrofuran, methanol, ethanol, isopropanol, acetone, formic or acetic acid.  Many other adjurants are specified among which are dispersing agents such as lignin sulphonate and a naphthalene-2-sulphonic acid/formaldehyde condensate, protective colloids such as carboxymethyl-cellulose, acetylated polyvinyl alcohol or polyvinyl pyrrolidone both of k-value 30, antioxidants such as hydroquinone; wetting agents such as the sodium salt of sulphonated oleic acid N-methylcyclohexylamide, migration inhibitors such as sodium acetate and thickening agents such as sodium alginate.  Examples are given of dyeing and printing in which a great variety of dyestuffs is employed; some of them are described in Specifications 520,199, 771,320, 811,221, 811,222, 824,300, 827,568 and 900,764 and German Specifications 335,809, 742,932, 742,939 and 908,068.  Other dyestuffs referred to include <FORM:0923162/IV(a)/2> and <FORM:0923162/IV(a)/3> Specifications 520,301 and 805,548 also are referred to.