Classifications

• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
  • D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
  • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
  • D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes

Definitions

• the invention relates to a process for dyeing nitrogencontaining textile fibres with wool dyestuffs in the presence of a combination of levelling agents substantially consisting of (a) quaternary ammonium compounds and (b) acid esters of at least dibasic oxygen acids and their corresponding alkali metal, ammonium and amine salts, of polyglycol compounds.
• At least one quaternary compound and at least one acid ester of the composition defined above which are derived from identical or different polyglycol compounds, both these polyglycol compounds answering to the above definition.
• the aliphatic hydrocarbon residues containing 12 to 24 carbon atoms may be saturated or unsaturated, branched or preferably linear.
• they contain 16 to 3,529,922- Patented Sept. 22, 1970 and octadecenylamine.
• monoalkyl-alkylenediamines Whose alkyl radical contains 12 to 24 and the alkylene radical 2 to 3 carbon atoms. These alkyl radicals may be of the same composition as mentioned with the rnonoamines referred to above.
• alkenoxy compounds of low or high molecular weight there are obtained in known manner polyglycol compounds.
• Suitable alkenoxy compounds are, for example, low-molecular compounds such as ethylene oxide, propylene oxide, or butylene oxide, or compounds of higher molecular Weight such as decene-oxide, olefine oxides containing 16 to 18 carbon atoms or styrene oxide.
• the amine may be reacted with a unitary alkylene oxide or With a mixture of different alkylene oxides. By virtue of its ready accessibility propylene oxide in admixture with ethylene oxide is preferred to the other alkylene oxides. At least a substantial portion of the resulting groups should be ethenoxy groups.
• both the quaternary ammonium compounds and the acid esters are derived from polyglycol compounds of the formula oHPom-o H M
• R represents an aliphatic, preferably linear, hydrocarbon residue containing 12 to 24 carbon atoms
• m and s each is 1 or 2
• p, q and r are Whole numbers, the sum p+q+r(m-l) being at least 4.
• Quaternation of the amine-alkylene oxide adducts gives rise to the compounds (a) and esterification to the compounds (b). Both these reactions may be carried out in known manner.
• the esterification is advantageously performed with functional derivatives of at least dibasic oxygen acids under conditions such that at least one acid ester group preferably in the form of an alkali, ammonium or amine saltis introduced.
• Polybasic organic acids suitable for formation of the acid esters are organic polycarboxylic acids or carboxylic acid-sulphonic acids, for example maleic or succinic acid-sulphonic acid, or poly'basic inorganic oxygen acids such as phosphoric acid or preferably sulphuric acid, or functional derivatives of these acids such as their anhydrides, halides or amides. It is advantageous to manufacture the acid sulphuric acid esters in the form of their ammonium salts directly by heating the starting materials with amidosulphonic acid in the presence of urea.
• the starting polyglycol compounds are reacted in known manner with a conventional alkylating or aralkylating agent such as dimethylsulphate, ethylbromide, benzylchloride, chloracetamide, ethylene-chlorohydrin, ethylene-bromohydrin, epichlorohydrin or epibromohydrin.
• a conventional alkylating or aralkylating agent such as dimethylsulphate, ethylbromide, benzylchloride, chloracetamide, ethylene-chlorohydrin, ethylene-bromohydrin, epichlorohydrin or epibromohydrin.
• the acid esters (b) must contain at least one ester group per molecule. In other respects, there may be used compounds of which only some or 11 hydroxyl groups present are esterified. In the case of the compounds (a) most or all of the tertiary nitrogen atoms should be quaternated. The effect of the products is, however, hardly impaired when a monoamino-polyglycol compound is quaternated only to 85 to 90% or when in a diamino-polyglycol compound only one of the two nitrogen atoms is quaternated.
• the compounds (a) and (b) may be advantageous when the compounds (a) and (b) have a higher or lower content of alkenoxy groups and the compounds (a) have been reacted with certain quaternating agents.
• the present process my be used for dyeing nitrogenous fibres in any desired stage of their processing, which are suitable for dyeing with wool dyestuffs in the usual manner, for example polyamide fibres from E-caprolactam or adipic acid and hexamethylenediamine. Particularly suitable are natural fibres such as silk or above all wool.
• wool yarn may be dyed with any desired wool dyestuff by one of the conventional methods.
• the dyestuffs may belong, for eX- ample, to the following types:
• Acid wool dyestuffs including dyestuffs, especially anthraquinone and azo dyestuffs that contain at least one acid group imparting solubility in water, preferably a sulphonic acid group, but which contain no metal in complex union and no reactive groups.
• (B) 1 2-chromium or -cobalt dyestuff complexes that are free from acid groups imparting solubility in water that do not participate in the complex formation.
• These dyestuffs contain as a rule a sulphonamide group which may be substituted on the nitrogen atom or a methylsulphone group.
• Reactive dyestuffs which, in contradistinction to the above types of dyestuffs, contain at least one group or substituent capable of reacting with the nitrogenous fibre.
• these dyestuffs may belong to widely disparate types; they may be, for example, stilbene, perinone, peridicarboxylic acid imide, nitro, triphenylmethane or phthalocyanine dyestuffs or above all acid anthraquinone or azo dyestuffs, including both metal-free and metallizable and metalliferous monoazo or polyazo dyestuffs containing groupings or substituents capable of reacting with the nitrogenous fibres.
• the dyestuffs contain at least one, but generally 2 or more, acid groups imparting solubility in water. Particularly good results are in general achieved with dyestuffs that contain 3 sulphonic acid groups.
• labile substituents that can be eliminated with entrainment of the electron pair of the bond there may be mentioned, for example, aliphatically bound phosphoric acid ester or sulphuric acid ester groups, sulphonylfluoride groups, aliphatically bound sulphonyloxy groups and above all halogen atoms, especially a mobile chlorine atom.
• These labile substituents advantageously occupy the 'y or ii-position of an aliphatic residue bound with the dyestuff molecule directly or through an amino, sulphone or sulphonamide group.
• these mobile halogen atoms may also be in an aliphatic acyl radical (for example in the B-position of a propionyl residue) or preferably in a heterocycle; in this last-mentioned case there may be used dyestuffs containing a monohalogenated heterocycle, for example a monochlorinated 1,3,5-triazine residue, such as the 1,3,5-triazine residue of the formula where X is an alkyl, aryl, aralkyl, alkylmercapto or arylmercapto radical, especially a possibly substituted amino group or a preferably substituted hydroxy group, as well as dyestuffs that contain a dichlorotriazine or a dichloropyrimidine residue.
• a monohalogenated heterocycle for example a monochlorinated 1,3,5-triazine residue, such as the 1,3,5-triazine residue of the formula where X is an alkyl, aryl, aralky
• the quaternary ammonium compounds (a) preferably contain a halogen as the anion so that, for example, said quaternating compounds are obtained by reaction of a tertiary amine with chloracetamide, ethylene-chlorohydrin, ethylene-bromohydrin, epichlorohydrin or epibromohydrin.
• the quaternary compounds (21) and the acid esters (b) contain at least 15, for example 20 to 35, alkenoxy groups such as ethenoxy groups, they are particularly suitable for use in dyeing with dyestuffs sub A, B or E, and also sub D, especially when the quaternary nitrogen atoms are linked to dimethylsulphate.
• the proportions of substances to be added to the dyebaths to be used in the present dyeing process may vary within relatively wide limits.
• the amount of dyestuff depends on the desired tinctorial strength, taking into consideration the nature of the material to be dyed. It is advantageous to choose the quantity of the polyglycol compounds (a) and b) as a whole, that is to say a+b, referred to the weight of the fibre] from the range of 0.2 to 3%.
• the ratio of quaternary compound (a) to acid ester (b) should be from 3:1 to 1:3 or preferably from 2:1 to 1:2. It is advantageous to use equimolecular proportions of (a) and (b).
• the known dyeing methods conventionally employed for the selected type of dyestuif may be used.
• it is advantageous to dye wool in an acid medium that is to say at a pH value from 1.7 to 6, which is adjusted by adding acetic, formic or sulphuric acid.
• Dyeing is performed at an elevated temperature, for example by starting the dyeing process proper at 50 to 80 C., heating the bath to the boil and continuing and completing the dyeing process at the boil.
• the material to be dyed may be advantageous to introduce the material to be dyed into the bath containing the polyglycol compounds (a) and (b) and the further ingredients at room temperature or at a moderately raised temperature, whereupon the material to be dyed is heated, and at an elevated temperature, for example, at 50 to 80 C., an aqueous solution of the dyestuff is added to the dyebath.
• the quaternary ammonium compound (a) and the acid ester (b) may be added to the dyebath separately.
• a stable dyeing preparation ready for use may be manufactured by mixing the two components as such, or aqueous solutions thereof, at a suitable ratio, for example of 1:3 to 3:1, which preparations contain (a) quaternary ammonium compounds of polyglycol compounds and (b) acid esters of polyglycol compounds, derived from at least dibasic oxygen acids;
• the compounds (a) and (b) have the compositions defined above.
• the two polyglycol compounds produce on textile fibres, especially on wool in any stage of processing, a good levelling effect.
• This is a true combination eifect, since, when the quaternary compound (a) is used in combination with the acid ester (b), there are achieved effects which as a whole cannot be achieved with either component by itself. It is a substantial advantage of the combination that it can be used for a wide range of types of dyestuffs. Furthermore, various disadvantages which impede or restrict the use of known wool levelling agents do not occur in this process.
• the known levelling agents increase the adhesion between fibre and fibre so that a more or less pronounced sticking together of the yarns occurs, and as a result channels are formed in the material and the dyeing turns out uneven.
• the known levelling agents have the further disadvantage that adducts from dyestuif and levelling agent on being heated below the boiling temperature undergo dehydration and settle out in droplet form (the so-called turbidity point) which are mechanically retained by the material. This phenomenon, called the draining effect, may result in dyeings that are instable towards abrasion and uneven.
• levelling agents for wool compounds obtained by treating esterifiable polyglycol compounds, whose molecule contains at least one basic nitrogen atom, a lipophilic residue and a polyglycol chain of at least 4 ethoxy groups, with sulphating or phosphating agents and quaternating at least one tertiary nitrogen atom with dimethylsulphate.
• the known compounds of this composition can, however, be used only to a limited extent as levelling agents for wool dyestuffs, and moreover they cause deformation of crosswound bobbins.
• the combinations to be used in the present invention display on dyeing unwoven wool none of the aforementioned disadvantages of the known levelling agents developed for this purpose, they satisfy all requirements of the dyeing practice and render superfluous the use of dyeing assistants which render the dyeing process more complicated and expensive.
• the present process may also be successfully applied to cleaning and at the same time dyeing greasy wool, for example wool in the yolk.
• Manufacturing instruction I (a) 1190 parts (1 mol) of an adduct from 20 mols of ethylene oxide and 1 mol of a commercial fatty amine (tallow fatty amine) which contains 35% of hexadecylamine, 25% of octadecylamine and of octadecenylamine are heated to 55 to 80 C. while being stirred. Within 15 minutes 126 parts of dimethylsulphate are added and the whole is heated for 1 hour at 75 to 80 C., then dissolved in 1316 parts of water, to yield a solution of strength of the quaternation product.
• a commercial fatty amine tallow fatty amine
• Levelling agent 1 1 part of the quaternation product described under (a) and 1 part of the esterifiable product sub (b) are mixed together: Levelling agent 1.
• Manufacturing instruction II (a) 5 80 parts (1 mol) of an adduct from about 7 mols of ethylene oxide with 1 mol of a commercial fatty amine consisting of 35% of hexadecylamine, 25% of octadecylamine and 45% of octadecenylamine are heated to 60 to 65 C. In the source of 30 minutes 145 parts of chloracetamide are stirred in and the batch is heated for 12 hours at 95 to 100 C. and then dissolved in 622 parts of water, to yield a solution of about 50% strength which contains the quaternation product.
• Manufacturing instruction HI 144 parts each of the adduct from 8 mols of ethylene oxide with 1 mol of a commercial alkylpropylenediamine of the formula RNH(CH NH [where R represents the hydrocarbon corresponding to soybean fatty amine], are
• Manufacturing instruction IV (a) 926 parts (1 mol) of an adduct from 14 mols of ethylene oxide and 1 mol of a commercial fatty amine containing about 10% of stearylamine, 55% or arachidylamine and 35% of behenylamine are mixed at 60 C. with 150 parts of epichlorohydrin and then quaternated for 16 hours at 100 to 105 C.
• Manufacturing instruction V 580 parts (1 mol) of the adduct, used in manufacturing instruction Ila, from 1 mol of tallow fatty amine and 7 mols of ethylene oxide are mixed within 30 minutes at 80 C. with 108 parts of maleic anhydride, and the mixture is kept for 30 minutes at 100 C. and then for 30 minutes at 120 C. After cooling to 100 C., a solution of 200 parts of sodium sulphite in 720 parts of Water is added and the batch is heated for another hour at 95 to 100 C., to yield a solution of 50% strength which contains the sodium salt of the sulphosuccinic acid ester of the ethylene oxide-fatty amine product.
• 1 part of the resulting product is mixed at about 40 C. with 1 part of the quaternation product obtained according to manufacturing instruction IIa: Levelling agent V.
• Manufacturing instruction VI 1410 parts (1 mol) of an adduct obtained by adding 1 mol of styrene oxide, 1 mol of propylene oxide and thenu 21 mols of ethylene oxide on to 1 mol of tallow fatty amine is quaternated with 360 parts of dimethylsulphate for 6 hours at 100 to 105 C. under nitrogen. 1 part of the resulting product is dissolved at 60 C. in 1 part of water and then mixed with 3 parts of the product prepared according to manufacturing instruction Ib: Levelling agent VI.
• Manufacturing instruction VII 2620 part (1 mol) of an adduct from 50 mols of ethylene oxide with 1 mol of stearylamine and 2 mols of butylene oxide are mixed at 60 C. with 200 parts of urea and 320 parts of amidosulphonic acid and esterified for 6 hours at 100 to 105 C. The reaction product is then dissolved in 2480 parts of water, to yield a solution of about 50% strength which contains the ammonium salt of the acid sulphuric acid ester of the adduct. 5 parts of the resulting product are mixed with 2 parts of the product prepared according to manufacturing instruction Ia: Levelling agent VII.
• Manufacturing instruction VIII 4410 parts (1 mol) of an adduct from 1 mol of a commercial laurylpropylenediamine, 2 mols of a commercial olefine oxide containing a total of 16 to 18 carbon atoms, and 160 mols of ethylene ovide are quaternated under nitrogen with 440 parts of dimethylsulphate for 12 hours at to C. 8 parts of the resulting product are then dissolved with heating in 8 parts of water and then mixed at about 40 C. with 5 parts of the product prepared according to manufacturing instruction Ib: Levelling agent VIII.
• Manufacturing instruction IX 7770 parts (1 mol) of an adduct from 1 mol of a commercial laurylpropylenediamine, 2 mols of dodecene oxide and 160 mols of ethylene oxide are quaternized under nitrogen with 950 parts of dimethylsulphate for 12 hours at 100 to C. 8 parts of the resulting product are dissolved with heating in 8 parts of water and then mixed at about 40 C. with 9 parts of the esterified product prepared according to manufacturing instruction Ib: Levelling agent IX.
• Manufacturing instruction X (a) 580 parts (1 mol) of the adduct, used in manufacturing instruction IIa, from 1 mol of tallow fatty amine with 7 mols of ethylene oxide are quaternated with 196 parts of epichlorohydrin for 12 hours at 100 to 105 C. and then dissolved in 658 parts of water.
• Manufacturing instruction XI 580 parts (1 mol) of an adduct from 1 mol of tallow fatty amine and 7 mols of ethylene oxide are quaternated with 120 parts of ethylene-chlorohydrin for 24 hours at 9 120 to 125 C. and then dissolved with heating in 620 parts of water.
• the resulting preparation which is of 50% strength, is mixed at about 40 C., with the product obtained according to manufacturing instruction Xb: Levelling agent XI.
• Manufacturing instruction XII 580 parts (1 mol) of an adduct from 1 mol of tallow fatty amine with 7 mols of ethylene oxide are quaternated with 188 parts of ethylene-bromohydrin for 24 hours at 105 to 110 C. and then dissolved with heating in 642 parts of water.
• the resulting product which is of 50% strength, is mixed at about 40 C. with the product obtained according to manufacturing instruction Xb: Levelling agent XII.
• Manufacturing instruction XIII (a) 162 parts (1 mol) of the adduct, described in manufacturing instruction Ib, from 1 mol of fatty amine and 30 mols of ethylene oxide are quaternated under nitrogen with 21 parts of dimethylsulphate for 6 hours at 95 to 100 C. On dissolving the reaction product in 180 parts of water a preparation of about 50% strength is obtained.
• Manufacturing instruction XIV A mixture of 27.6 parts of urea phosphate and 31.6 parts of urea is slowly heated to 155 C. and then for 30 minutes at 155 to 160 C., allowed to cool to 110 C., then 64.8 parts of the adduct, described in manufacturing instruction Ib, from 1 mol of fatty amine and 30 mols of ethylene oxide are added and the whole is heated under nitrogen for 2 hours at 145 to 150 C. After cooling the flask contains 107 parts of a hard substance which is dissolved in 166 parts of hot water, to yield a solution of about 25% strength which contains the ammonium salt of the acid phosphoric acid ester of the fatty amine-ethylene oxide adduct.
• Manufacturing instruction XV 1190 parts (1 mol) of an adduct from 1 mol of tallow fatty amine and 20 mols of ethylene oxide are quaternated for 24 hours at 110 to 115 C. With 126 parts of benzylchloride.
• Manufacturing instruction XVI 1190 parts (1 mol) of an adduct from 1 mol of tallow fatty amine and 20 mols of. ethylene oxide are dissolved in 400 parts of absolute alcohol and stirred with 400 parts of methylbromide for 8 hours at 5 to 10 C. and then for 20 hours at 20 to 25 C.
• the liquid constituents are distilled off under vacuum on the waterbath, to leave 1286 parts of the quaternation product.
• Manufacturing instruction XVII (a) 2510 parts (1 mol) of an adduct from 1 mol of tallow fatty amine and 50 mols of ethylene oxide are quaternated with 440 parts of dimethylsulphate under nitrogen for 6 hours at to C.
• Manufacturing instruction XVIII 7770 parts (1 mol) of an adduct from 1 mol of a commercial laurylpropylenediamine, 2 mols of dodecene oxide and 160 mols of ethylene oxide are quaternated under nitrogen with 950 parts of dimethylsulphate for 12 hours at 100 to C.
• Example 1 100 kilograms of Wool yarn on crosswound bobbins are wetted for 10 minutes in 1500 litres of water at 50 C. in a dyeing apparatus for crosswound bobbins. There are then added: 2 kg. of acetic acid of 80% strength, 10 kg. of crystalline sodium sulphate, 1 kg. of levelling agent I and 0.5 kg. of the 1:2-cobalt complex of the dyestuif of the formula The temperature is raised within 60 minutes to the boil and the whole is boiled for one hour; the yarn is then rinsed, the bobbins are freed from theirwater content and dried. An even, yellow dyeing is obtained. The crosswound bobbins have not been deformed. When the levelling agent I is replaced by an equal quantity of levelling agent XVIII, similar results are obtained.
• Example 3 100 kilograms of wool yarn on crosswound bobbins are wetted in 1000 litres of Water containing 1 kg. of levelling agent II at 50 C. for minutes in a vat for dyeing crosswound bobbins. 2 kilograms of acetic acid of 80% strength, 10 kg. of crystalline sodium sulphate SOKH and 1 kg. of one of the dyestufis of the following formublue o N-O-NH-OC-OHa N Example 2 (l HN- -NIIO/ ⁇ CHNO 100 kilograms of wool yarn are wetted in 2000 litres So H of water and 6 kg. of sulphuric acid of 98% strength 0 for 10 minutes at 50 C. in a hank dyeing vat. There are then added: 10 kg. of crystalline sodium sulphate,
• the whole is heated within 20 minutes to 80 C. and dyeing is performed for one hour at 80 C.
• the yarn is then rinsed.
• levelling agent X there may be used the products mentioned in Example 4, and also levelling agent II or XV IH.
• Example 7 100 kilograms of wool slubbings are packed into a machine for dyeing slubbings. In the liquor tank a bath is prepared from:
• Example 8 100 kilograms of nylon 6 spun yarn on conical crosswound bobbins are wetted in a machine for dyeing crosswound bobbins in 2000 litres of water at 50 C. Then the following are added:
• the temperature is raised to the boil within 60 minutes, and the yarn is dyed for 60 minutes at the boil, then rinsed and dried, whereupon it displays a level, fast, blue shade.
• the bobbins have undergone no deformation.
• Example 9 200 kilograms of wool yarn in hank form are wetted in a hank dyeing machine in 3000 litres of water at C. Then the following are added.
• levelling agent XVII 2 kg. of the 1:2-cobalt complex containing two molecules of the dyestuif component of the formula NHCH(OHa)z 0.5 kg. of the dyestufl of the formula SOaH 0.5 kg. of the dyestufr of the formula HOaS 0311
• the dyebath is heated to the boil and the yarn is dyed for minutes at the boil, then rinsed and dried; it displays a level claret shade.
• the yarn is lofty and voluminous. Similar results are achieved with levelling agents X IH, XIV, VI, VII, VIII, IX, XV and XVI.
• Example 10 kilograms of woolen pieces are wetted in a winch vat in 4000 litres of water at 40 C. Then the following are added:
• N N- C I C N HgN S 02''- I I 3O C1 C0 OH HzN Blue.
• Process for dyeing nitrogenous textile fibers with wool dyestuffs which consists in dyeing the fibers with dyeing preparations containing a levelling agent substantially consisting of mixtures of (a) quaternary ammonium compounds and (b) acid esters of at least dibasic oxygen acids or their alkali, ammonium or amine salts, both of polyglycol compounds, each corresponding to the formula wherein R represents an aliphatic hydrocarbon atom with 12 to 24 carbon atoms, Z is a member selected from the group consisting of a hydrogen atom, an alkyl group with 1 to 16 carbon atoms and a phenyl group, wherein at least one Z is a hydrogen atom, m and a each is 1 or 2, p, q and r are whole numbers, the sum p+q+r(m-1) being at least 4 and at the most 200; the quaternated products being obtained by reacting the polyglycol compounds With quaternating agents selected from the group ride, chloracetamide, ethylene
• polyglycol compounds by reacting the polyglycol compounds with at least dibasic acids or their functional derivatives such as their anhydrides, halides or amides selected from the group consisting of sulfuric acid, phosphoric acid, chlorosulphonic acid, amidosulphonic acid and maleic anhydride; the ratio of quaternary compound (a) to acid ester (b) being in the range 3:1 to 1:3.
• 19 p, q, and p, q, are whole numbers wherein the sum (p+q) and (p'+q) each is at least 4.
• the quaternating agent of compound (a) is a member selected from the group consisting of dimethylsulfate, chloroacetamide, epichlorohydrin, epibromohydrin, ethylene chlorohydrin, ethylene bromohydrin benzylchloride and methylbromide and the acid ester radical belongs to an acid selected from the group consisting of sulfuric acid, sulfosuccinic acid and phosphoric acid or a water soluble salt of such acids.
• wool dyestutfs selected from the group consisting of acid wool dyes, 1: l-chromium complex dyes containing sulfonic acid groups, 1:2-chromium or cobalt complex dyes containing at least one free acid group imparting solubility in water; 1:2-chromium or cobalt complex dyes containing sulfonamide or alkylsulfone groups and reactive dyestuffs.
• Wool is dyed with water-soluble wool dyes selected from the group con sisting of lzl-chromium complex dyes containing sulfonic acid groups, 1:2-chromium or cobalt complex dyes containing at least two free acid water-solubilizing groups and reactive dyes in the presence of (a) quaternary ammonium compounds obtained by quaternating with a compound selected from the group consisting of chloroacetamide, ethylene chlorohydrin, ethylene bromohydrin, epichlorohydrin and epibromohydrin and (b) the ammonium salt of the sulfuric acid ester of polyglycol compounds containing 6 to 9 alkenoxy groups.
• water-soluble wool dyes selected from the group con sisting of lzl-chromium complex dyes containing sulfonic acid groups, 1:2-chromium or cobalt complex dyes containing at least two free acid water-solubilizing groups and reactive dyes in the presence of (a) quaternary ammonium compounds obtained by qua
• wool is dyed with water-soluble wool dyes selected from the group consisting of acid wool dyes 1:1-chromium complex dyes containing sulfonic acid groups, 1:2-chromium or cobalt complex dyes containing one sulfonic acid group, and 1:2- chromium or cobalt complex dyes containing sulfonamide or methylsulfone groups in the presence of (a) quaternary ammonium compounds obtained by quaternating with dimethylsulfate and (b) the ammonium salt of the sulfuric acid ester of polyglycol compounds containing 20 to 35 alkenoxy groups.
• water-soluble wool dyes selected from the group consisting of acid wool dyes 1:1-chromium complex dyes containing sulfonic acid groups, 1:2-chromium or cobalt complex dyes containing one sulfonic acid group, and 1:2- chromium or cobalt complex dyes containing sulfonamide or methylsulfone groups in the presence of (a) quaternary
• dyeing assistant suitable for carrying out the dyeing process according to claim 1 which dyeing assistant substantially consists of a mixture of (a) quaternary ammonium compounds and (b) acid esters of at least dibasic oxygen acids or their alkali, ammonium or amine salts, both of polyglycol compounds, each corresponding to the formula (H-CH-Oh-H I g I I Z -1 Z Z wherein R represents an aliphatic hydrocarbon atom with 12 to 24 carbon atoms, Z is a member selected from the group consisting of a hydrogen atom, an alkyl group with 1 to 16 carbon atoms and a phenyl group, wherein at least one Z is a hydrogen atom, m and s each is 1 or 2, p, q and r are whole numbers, the sum p+q+r(m1) being at least 4 and at the most 200; the quaternated products being obtained by reacting the polyglycol compounds with quaternating agents selected from the group consisting of dimethylsulf

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• 1965
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• 1966
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