IL43714A - Quaternary phosphonium salts their preparation and their use in dyeing - Google Patents

Description

quaternary p their preparation and their use in dyeing The present invention relates to a new method of preparing quaternary phosphonium their use in and to certain such new quaternary phosphonium In particular the invention relates to a method of preparing quaternary phosphonium salts of the formula X wherein B represents an alkyl radical with 4 to 18 carbon atoms alkyl radical with 8 12 carbon is 1 or X is a chlorine or bromine atom and n is an integer between 3 and which comprises treating 1 mole triphenylphosphine with moles of polyethylene glycol monoether of formula wherein and n are as defined in the presence of moles HC1 or the reaction taking place at the melting of the components or in an excess of polyethoxylate compound of the formula II as at a temperature from and preferably from and at atmospheric pressure and under nitrogen The polyethylene glycol mono ethers are easily obtainable intermediates and final products of the detergent Some examples of compounds of formula II are triethylene glycol butyl triethylene glycol or pentadeca ethylene glycol monolauryl or entadecaethlene lcol monocet l In these procedures it is possible to use chemically homogeneous compounds of formula or mixtures of such compounds where the components of the mixture differ by Unetherized polyethylene glycol often present in such does not disturb the quaternary salts obtained in the reaction may be prepared in pure state either by precipitation from the mixture with an organic in which the phosphonium salts are insoluble or by precipitation with an anion with large followed by the decomposition o the complex or by preparatory but when used as the product may not be in a pure There may also be used the solution of the quaternary phosphonium salts in the excess of polyethoxylate compound as they result from the These solutions are much stabler than the pure phosphonium salts and they may be kept The pure quaternary phosphonium salts of the formula I are very colourless crystalline solids or viscous The obtained quaternary phosphonium salts I possess excellent properties as retarder in dyein polyacrylonitrile fibres or fibres from polyaerylonltrile copolymers with basic In comparison with the ordinary cationic retarders they display a satisfying at already very small concentrations as by weight to the Their action is not by surfactants and it becomes as the dyeing so that a better usage of the dye The fibres are dyed according to the known procedure of dyeing with basic but instead of the retarder in use the above described quaternary phosphonium salts are So quaternary phosphonium salt have not been used as retarder in the of The compounds of formula I wherein S is an to 18 carbon atoms or from 8 to 12 n is an integer from 3 to are new In the following examples the for n in the general formula is to b understood as a mean that stands for a homogenous chemical compound which is actually equivalent to a mixture of either polyethylene glycol monoethers or quaternary phosphonium Example 1 Into a flask with four with ascending thermometer and nitrogen g phosphine and g triethylene glycol ether are Nitrogen is blown inside and a nitrogen atmosphere is maintained by continuous There are duced g hydrochloric acid in concentrated lution and while stirring the mixture of is heated up to This temperature is maintained till no more water is this markin the end of the The conversion is The obtained precipitates a lower temperature than its solidification point from the ture of by diluting the latter with a 40 fold amount of anhydrous After the precipitate saturated with ethyl acetate is dried in a vacuum dryer in the presence of phosphorus The precipitation of the product in order to obtain it in pure state can be made with carbon tetrachloride or The same as in the above can be reached if one works with a bigger excess of polyetoxylate the adding of an amount larger than 3 moles to 1 mole of tertiary phosphine being If we use g instead of c Q with Example 2 Into a flask like the one in example g triphenylphosphine and g triethylene glycol reaction is continued art This operation is repeated once The total amount of hydrochloric g When no water the reaction is The separation be as in example with quantitative I use g instead of in centrated we get the corresponding in tive 4 Into a flask like the one in example g triphenylphosphine and g triethylene glycol monocetyl ether are At nitrogen atmosphere g in concentrated solution are added and the flask is heated at During the reactio iore are added in three The reaction is completed when more water The of separation may be as If instead of glycol ether there are used or glycol get the also wit quantitative A redaction of the reaction rate with the increase of the etoxylation degree If nse triethylene glycol ether the equivalent of triethylene glycol we get in quantitative dye bath prepared adding a litre of g acid of 3 g anhydrous g B and g heated at 30 g of are In 30 minutes the temperature is to and it is maintained for 90 The dyeing process s interrupted and dyed material is and is uniformly in contraittstinction another dyed in the the absence of the obvious inequalities in The same result is reached if or g of phosphor from this example to the dye bath in a ution of of triethylene glycol inonolauryl ether or i instead of same amsnnt of is 6 dye bath is prepared adding to a litre of water aeetic acid of 3 g anhydrous sodium g nonionic agent ethoxilate fatty Maxxlonblau and g 8 A dye bath is to litre of water g acetic acid of 3 g anhydrous g onblaa and g in of in triethylene glycol and 30 g insufficientOCRQuality

Claims (1)

1. 8 A of preparing quaternary phosphonium salts of the general formula I wherein R represents an containing from 4 to 18 carbon atoms or an alkyl radical containing from 8 to 12 carbon is 0 or X is or and n is an integer from 3 to which comprises treating 1 mole with moles polyethylene glycol monoether of the formula II R OH wherein R and n are as defined in the presence of moles or the reaction taking place at the melting of the components or in an excess of ethoxylated compound of the formula at tures from to preferably from at atmospheric pressure and under nitrogen A method according to claim wherein said compounds of the formula II are adducts of butyl alcohol and 3 moles of ethylene of lauryl alcohol and 9 or moles of ethylene of alcohol and 12 or 15 moles ethylene or of isooctylphenol and 3 moles of ethylene A method of applying quaternary phosphonium salts of the general formula I in claim 1 as retarders in the dyeing of polyacryloaitrlle fibres with basic consisting in adding of of the said quaternary phosphonium salts to the the bath and dyeing in the usual prescribed for basic 9 A of applying quaternary salts according to claim wherein quaternary phosphonium salts of the general are added to the dye hath in pure or as solutions in the excess of the polyethoxylated compound XX used as Quaternary phosphonium salts of the general X wherein is an containing 7 to 18 carbo atoms or radical containing 8 to 12 carbon is or or and a integer 3 to insufficientOCRQuality