US3785767A

US3785767A - Process for the continuous dyeing and printing of fibre materials containing ionic groups

Info

Publication number: US3785767A
Application number: US00062651A
Authority: US
Inventors: D Hildebrand; R Kuth
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1969-08-16
Filing date: 1970-08-10
Publication date: 1974-01-15
Anticipated expiration: 1991-01-15
Also published as: CH544183A; CA977904A; CH1219270A4; JPS5029074B1; FR2058330B1; BE754886A; DE1941698A1; GB1274134A; DE1941698B2; NL7012054A; FR2058330A1

Abstract

Pad-steaming process for the continuous dyeing and printing of fibre materials containing ionic groups, from organic solvents, characterised in that the fibre materials are dyed or printed with chlorinated hydrocarbon dyeing baths containing ionic dyestuffs which have been rendered soluble in chlorinated hydrocarbons by the formation of salts or addition products with lipophilic compounds. With the new process, it is possible to produce on fibre materials containing ionic groups strong, level and well developed dyeings and prints in excellent yields.

Description

nited States-Patent 1191 Hildebrand et al.

[ PROCESS FOR THE CONTINUOUS DYEING AND PRINTING OF FIBRE MATERIALS CONTAINING IONIC GROUPS [75] Inventors: Dietrich Hildebrand, Odenthal; Robert Kuth, Cologne, both of Germany [73] Assignee: Bayer Aktiengesellschaft,

Leverkusen, Germany 22 Filed: Aug. 10,1970

21 Appl. No.: 62,651

[30] Foreign Application Priority Data Aug. 16, 1969 Germany 1941698 [52] U.S. Cl 8/54, 8/94, 8/168, 8/174, 8/169 [51] Int. Cl D061) 3/14 [58] Field of Search 8/94, 168, 174, 173, 8/178, 6, 54

[56] References Cited UNITED STATES PATENTS 3,510,243 5/1970 Seuret et a1 8/94 X 2,721,111 10/1955 Long et al 8/6X 3,164,449 1/1965 Bux'baum 8/6 X 2,274,751 3/1942 Sowter et a1 8/173 3,523,749 8/1970 MacLeod et a1 8/54.2

1 1 Jan. 15, 1974 3,623,834 11/1971 Seuret et a1 8/173 FOREIGN PATENTSOR APPLICATIONS 682,830 1/1966 Belgium 8/174 454,084 6/1968 Switzerland 8/178 R 1,581,325 8/1969 France 8/94 OTHER PUBLICATIONS CQIQLLUEZS, 72nd El ar 195M91- VZLEPM- 2815 and 2816.

Primary Examiner-Donald Levy Assistant Examiner-T, J. Herbert, .lr. Attorney-Plumley and Tyner [5 7] ABSTRACT 8 Claims, No Drawings PROCESS FOR THE CONTINUOUS DYEING AND PRINTING F FIBRE MATERIALS CONTAINING IONIC GROUPS The invention relates to a pad-steaming process for the continuous dyeing and printing of fibre materials containing ionic groups, from organic solvents; the process is characterised in that the fibre materials are dyed or printed with chlorinated hydrocarbon dyebaths containing ionic dyestuffs which have been rendered soluble in chlorinated hydrocarbons by the formation of salts or addition products with lipophilic compounds.

Chlorinated hydrocarbons suitable for the process according to the invention are primarily the chlorinated hydrocarbons the boiling points of which lie between 40 and 170C, e.g. aliphatic chlorinated hydrocarbons such as methylene chloride, chloroform, car- .bon tetrachloride l l -dichloroethane, 1 ,2- dichloroethane, l,l ,l-trichloroethane, 1,1,2- trichloroethane, 1,1 ,l ,2-tetrachloroethane, 1,1 ,2,2- tetrachloroethane, pentachloroethane, l-

chloropropane, l,2-dichloropropane, l-chlorobutane, 2-chlorobutane, 1,4-dichlorobutane, l-chloro-2- methylpropane, 2-chloro-2-methylpropane or 4-chloro-2-methylpropane, and aromatic chlorinated hydrocarbons such as chlorobenzene and chlorotolune. Tetrachloroethylene, trichloroethylene and 1,1,1- trichloropropane have proved particularly satisfactory.

The fibre materials containing ionic groups, which are to be dyed according to the invention comprise:

a. fibre materials containing cationic groups.

These include all natural or synthetic fibre materials which can be dyed with anionic dyestuffs. These are natural polyamides especially wool and synthetic polyamides, e.g., poly-c-caprolactam, polyhexamethylene-diamine adipate and poly-wamino-undecanic acid;

b. fibre materials containing anionic groups.

These include all synthetic fibre materials which can be dyed with basic dyestuffs, especially the commercial polyacrylonitrile containing anionic groups such as sulphonic acid, sulphimide, carboxyl and- /or phosphonic acid groups; polyesters modified by carboxyl and/or sulphonic acid groups, such as polyethylene terephthalate, polycyclohexanedimethylene terephthalate; heterogeneous polyesters obtained from terephthalic acid, isophthalic acid and ethylene glycol or from terephthalic acid, sulphoisophthalic acid and ethylene glycol; furthermore, copolyether ester fibres obtained from phydroxybenzoic acid, terephthalic acid and ethylene glycol; or polyamides modified by sulphonic acid groups, such as polyhexamethylene adipate, polycaprolactam of poly-w-aminoundecanic acid.

The ionic dyestuffs which have been rendered soluble in chlorinated hydrocarbons by the formation of salts or addition products with lipophilic compensating ions and serve in the process according to the invention for the dyeing of fibre materials containing cationic groups comprise chlorinated hydrocarbon-soluble amine salts and amine addition products of dyestuffs containing 1 to 4 carboxyl and/or sulphonic acid groups.

The dyestuffs containing 1 to 4 sulphonic acid groups from which the amine salts or amine addition products soluble in chlorinated hydrocarbons are derived, may belong to a variety of dyestuff classes, for example, to

the azo, anthraquinone, phthalocyanine, azine and triphenyl-methane dyestuffs. These dyestuffs may also contain reactive groups.

Suitable amines on which the amine salts or amine addition products soluble in chlorinated hydrocarbons are based, are primary, secondary and tertiary monoamines as well as primary, secondary and tertiary polyamines. Examples of primary, secondary and tertiary monoamines are: optionally substituted aliphatic amines, such as tri-n-propylamine, 2-ethyl-hexylamine, dodecylamine, dodecylamine polyglycol ether with 20 mol ethylene oxide, hexadecylamine, hexadecylamine polyglycol ether with 20 mol ethylene oxide, octadecylamine,

N-methyl-octadecylamine, N-methyl-octadecylamine polyglycol other with 10 mol ethylene oxide,

cetylamine,

N,N-dimethyl-dodecylamine, N,N-dimethyl-hexadecylamine, v

N ,N-dimethyl-octadecylamine, N,N-dibutyl-dodecylamine, N,N-di-2-hydroxyethyl-oleylamine, N,N-dimethyl-N-(dodecanoylaminomethyl)-amine, N-methyl-N-2-hydroxyethyl-N-[y- (octadecanoylamino)-propyl]-amine, e-aminocapronic acid butyl ester, e-aminocapronic acid dodecylamide, e-aminoundecanic acid butyl-ester;

technical mixtures of fatty amines, such as coconut fatty amine and sperm oil fatty amines and their ethoxylation and propoxylation products; optionally substituted cycloaliphatic amines, such as N,N-dimethyl-cyclohexylamine, N-ethyl-cyclohexylamine, N-2-hydroxyethyl-cyclohexylamine, N,N-bis-(2-hydroxyethyl)-cyclohexylamine, N,N-bis-(2-chloroethyl)-cyclohexylamine, l-cyclohexylamino-propanol-Z, l-cyclohexylamino-propylamine-3 and dicyclohexylamine;

optionally substituted araliphatic amines, such as benzylamine, N,N-dimethyl-benzylamine, N,N-dibenzylamine, N-methyl-N,N-dibenzylamine,

l -amino-1 -phenyl-ethane,

i-amino-2-ethane;

optionally substituted aromatic amines, such as N-ethyl-aniline,

N,N-dimethyl-aniline,

N,N-diethyl-aniline,

N-propyl-aniline, N,N-dipropyl-aniline,

Nbutyl-aniline,

N-isobutyl-aniline, N-(2-chloroethyl)-N-butyl-aniline, N-2-hydroxyethyl-aniline, N-methyl-N-(2hydroxyethyl)-aniline, N-butyl-N-(2-hydroxyethyl)-aniline, N,N-bis-(2-hydroxyethyl)-aniline, N-methyl-N-(2-cyanoethyl)-aniline,

2-aminotoluene,

2-methylamino-toluene, Z-dimethylamino-toluene, 2-ethylamino-toluene,

3-amino-toluene, B-dimethylamino-toluene, 3-ehtylamino-toluene, 3-butylamino-toluene, 3(N-ethyl-N-hydroxyethyl )-amino-toluene, S-[N-bis-(ZZ-hydroxyethyl)l-amino-toluene, 3-[N-ethyl-N-( 2-dimethylaminoethyl)]-amino toluene,

4-methylamino-toluene, 4-dimethylamino-toluene,

'4-ethylamino-toluene,

4-diethylamino-toluene, N-ethyl-N-benzyl-aniline, 3-(N-ethyl-N-benzyl)-amino-toluene, xylidine,

2iso-propyl-aniline, 2-methyl-o-ethyl-aniline, 2,6-diisopropyl-aniline,

4-dodecyl-aniline, N,N dimethyl-4-dodecyl-aniline, 5,6,7,8-tetrahydro-naphthylamine-( l l-diethylamino-naphthalene, 4,4-diamino-dicyclohexylmethane, optionally substituted heterocyclic amines, such as N-propyl-morpholine, N-hexyl-morpholine, N-dodecyl-morpholine, N-hexadecyl-morpholine, N-dodecyl-piperidine, N-hexadecyl-piperidine, N-dodecyl-imidazole, 2-dodecyl-hydroindole, N-dodecyl-benzimidazole, 2-dodecyl-benzimidazole, l-(B-hydroxyethyl)2-octadecyl-imidazoline, l-(B-octadecanoylaminoethyl)2-octadecylimidazoline.

Examples of primary, secondary and tertiary polyamines are primarily aliphatic polyamines, such as N-dodecyl-N',N'-dimethyl-ethylene-diamine, N-dodecyl-N',N-diethyl-ethylene-diamine, N-octadecyl-N',N'-diethyl-ethylene-diamine, N-phenyl-N,N'-dimethyl-ethylene-diamine, N-oleyl-N,N'-dimethyl-ethylene-diamine, N-oleyl-N',N'-diethyl-ethylene-diamine, N-dodecyl-N',N '-dimethyl-propylene-diamine-(1,3), N-dodecyl-N',N'-diethyl-propylene-diamine-( l ,3), N-oleyl-N ,N '-dimethyl-propylene-diamine-( 1,3), N-oleyl-N ,N -diethyl-propylene-diamine-(1,3), N-dodecyl-ethylene-triamine, N-dodecyl-ethylene-tetramine, N-octadecyl-ethylene-tetramine.

lf acidic dyestuffs containing reactive groups are used, obviously, only those amines are suitable for the formation of salts or addition products, which contain no free NH-group.

Ionic dyestuffs which have been rendered soluble in chlorinated hydrocarbons by the formation of salts or addition products with lipophilic compounds and serve in the process according to the invention for the dyeing 6 of fibre materials containing anionic groups comprise all cationic dyestuffs which contain at least one cationic nitrogen atom and the anion of an acid which forms a salt soluble in chlorinated hydrocarbons with the cationic dyestuff.

The cationic dyestuffs from which the dyestuff salts to be used according to the invention, which contain at least one cationic nitrogen atom and are soluble in chlorinated hydrocarbons are derived, may belong to a variety of dyestuff classes, for example, to the azo, anthraquinone, azine, oxazine, xanthene, methine, triphenyl-methane and phthalocyanine dyestuffs. The dyestuffs include optical brightening agents, e.g. optical brightening agents from the stilbehe, couinarin, azole, and naphthalimide series.

Anions suitable for the dyestuff salts are: anions of acidic esters of inorganic acids, such as the dodecyl sulphate, I stearyl sulphate, oleyl sulphate, oleic acid sulphate, oleic acid butyl ester sulphate, ricinoleic acid ethyl ester sulphate, ricinoleic acid monoethyl glycol ester sulphate, oleic acid ethylamide sulphate, oleic acid ethanolamide sulphate, oleic acid diethanolamide sulphate, oleic acid diisobutylamide sulphate, oleic acid anilicle sulphate,

N-acetyloleylamine sulphate, undecylethylene glycol ether sulphate, tetradecyltriglycol ether sulphate, hexadecyldiglycol ether sulphate, octadecylpentaglycol ether sulphate, N-oleyl-4-aminobutano-Z-sulphate ions and anions of organic acids, such as oleic acid-N-dimethylamide sulphonate,

C, -C, -paraffin sulphonate, n-butylbenzene sulphonate, n-amylbenzene sulphonate, N-hexylbenzene sulphonate, n-heptylbenzene sulphonate, diisopropylnaphthalene sulphonate, dibutylnaphthalene sulphonate, di-(diisobutyl-methyl)-naphthalene sulphonate, dibutylphenyl polyglycol ether sulphate, n-octylbenzene sulphonate, n-nonylbenzene sulphonate, n-decylbenzene sulphonate, n-dodecylbenzene sulphonate, n-tetradecylbenzene sulphonate, n-hcxadecylbenzene sulphonate, n-octadecylbenzene sulphonate, Z-ethyl-hexylbenzene sulphonate, 2-propyl-heptylbenzene sulphonate, 2-butyl-octylbenzene sulphonate, Z-amyl-nonylbenzene sulphonate, dodecyl-(6)-benzene sulphonate and tetrapropylene benzene sulphonate ions; and also the palmitate, stearate, oleate ions.

The amounts in which the dyestuff amine salts or addition products or the salts of dyestuff bases with aliphatic or aromatic carboxylicor sulphonic acids to be used according to the invention are added to the chlorinated hydrocarbon paddingliquors may vary within wide limits, dependent upon the desired depth of colour; in general, amounts of 5 gm 30 g in 1000 g of padding liquor have proved satisfactory.

In the process according to the invention it has frequently proved useful, in order to increase the viscosity -'of the padding liquors, to add to the padding liquors about 8 to per cent by weight of water, referred to the weight of the chlorinated hydrocarbons, and 0 to 5 per cent by weight, referred to the weight of the ch1orinated hydrocarbons, of emulsifiers which form thickened emulsions with the chlorinated hydrocarbons when water is added. Suitable thickening emulsifiers are commercial non-ionic, anion-active, cation-active or zwitterionic emulsifiers, for example, oleic acid ethanolamide, oleyl alcohol eicosaglycol ether, nonylphenol heptaglycol ether, nonylphenol decaglycol ether, dodecylbenzene sulphonate, stearyl alcohol sulphate, N,N-dimethyl-N-benzyl-N-oleyl ammonium chloride and N,N-dimethyl-N-hexadecyl-N-(2-hydroxy-3- sulpho)-propylbetaine.

Furthermore, the chlorinated hydrocarbon dyebaths may contain auxiliaries which further the fixing of the dyestuff and/or improve the quality of the dyeing, for example, the levelness. Auxiliaries which have proved satisfactory are, for example, interface-active compounds which are soluble in chlorinated hydrocarbons, such as alkylbenzene sulphonates, fatty alcohol sulphates, ethoxylation products of fatty alcohols, alkylphenols, fatty amines, fatty acid amides and fatty acids; furthermore, fatty acid ethanolamides, fatty amine oxides, fatty acid amideamine oxides, as well as mixtures thereof. The quantities in which the auxiliaries are added to the dyebath amount to 0 4%, preferably 0.5 2%, referred to the fibre material to be dyed. Furthermore, the dyebaths may contain 0.1 2 per cent by weight, referred to the weight of the chlorinated hydrocarbons, of a lower carboxylic acid, suchas formic acid or acetic acid.

The process according to the invention is advantageously carried out by spraying or impregnating the fibre materials with the chlorinated hydrocarbon liquors, squeezing to a liquor absorption of 60 160%, and then treating them, optionally after an intermediate drying, with saturated steam or overheated steam at 100 200C. The fibre materials are subsequently rinsed with chlorinated hydrocarbons, in order to remove the non-fixed dyestuff, and subsequently dried by blowing with hot air.

The dyestuffs soluble in chlorinated hydrocarbons can be added to the chlorinated hydrocarbons liquors in undissolved form. However, it has also proved satisfactory to add them to the chlorinated hydrocarbons in the form of concentrated, e.g., 25 50%, solutions in chlorinated hydrocarbons or in organic solvents of unlimited miscibility with the latter, such as dimethyl formamide, isopropanol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, benzyl alcohol or butyrolactone.

From Swiss Patent Specification No. 454,084 there is known a process for the continuous dyeing of textile rhriErTi of synthetic poly amides rrbfii' organic sol- 7 vents, in which the textile materials are dyed or printed with dyebaths containing disperse dyestuffs or watersoluble dyestuffs in solvent mixtures. Compared with this process, the process according to the invention in which dyestuffs soluble in chlorinated hydrocarbons are used, is superior in that it yields stronger and more brilliant dyeing and prints, since the good solubility of the dyestuffs to be used according to the invention, in chlorinated hydrocarbons even without the addition of solubilizers enables stable single-phase padding liquors of high dyestuff concentrations to be prepared. Moreover, the use of dyestuffs soluble in chlorinated hydrocarbons according to the invention makes it pos- ,sible to rinse the fibre materials with chlorinated hydrocarbons so that the whole dyeing process can be carried out without the occurrence of waste water.

With the aid of the process according to the invention it is possible to produce on fibre materials containing ionic groups strong, lever and well developed dyevings and prints of outstanding fastness properties in ex cellent yields and without the occurrence of waste water, while the original textile fibre properties of the dyed material are retained to the optimal extent.

The parts given in the following Examples are parts by weight.

EXAMPLE 1 A wool fabric is padded on a foulard with a thickened padding liquor consisting of 20 parts of the dyestuff of the formula [coconut fatty aminel oas- 2 parts nonylphenol decaglycol ether,

898 parts perchloroethylene and parts of water i with a liquor absorption of steamed at 102C for 10 minutes, subsequently rinsed three times with perchloroethylene at room temperature and dried by blowing with hot air.

Without the occurrence of waste water, there is obtained a wool fabric which is dyed in a level red shade and has a substantially better-appearance than a fabric dyed in an aqueous solution.

EXAMPLE 2 A wool fabric is impregnated with a padding liquor 7 8 consisting of l i 2 parts N,N-dimethyl-N-hexadecyl-N-(2-oxy-3-sul- 20 parts of the dyestuff of the formula pho)-propyl-betaine,

$03 m Hty- \I CH3 ea K [CH:.(CHz)2nCHz-g -N=N F H\ CH2 a =s40 parts of a compound of the formula a 1 p glacial acetic acid '5 100 parts water and 03 HaN-CH2CH2OH 857 parts perchloroethylene with a liquor absorption of 100%, dried and steamed at 103C for minutes.

The fabric is subsequently rinsed in perchloroeth- CJHNGSO) ylene at 40C for 3 minutes and freed from the adher- 6 parts 1,3-bis-(2-ethyl-hexyl)-glycerol e h ing solvent by blowing with air. A clear brilliant yellow h 20 dyeing is obtained without the occurrence of waste wap ate, 2 parts isononyl phenol heptaglycol ether, 2 parts N,N-dimethyl-N-hexadecyl-N-(2-oxy-3-sulpho)-propyl-betaine, EXAMPLE 4 4 parts benzyl alcohol, 4 A polyacrylonitrile rope is impregnated with a pad- 200 parts water and ding liquor consisting of 756 parts perchloroethylene 20 parts of a dyestuff preparation consisting of with a liquor absorption of 104%, and, without inter- 34 parts f th d t ff f the formula Mfll CHa aim Q [-1 CH3 CH3 H mediate drying, steamed with steam at 103C for 15 8 Parts water minut 32 parts benzyl alcohol an The fabric is subsequently rinsed with a solution at 26 Parts p pf 60C f 1 part glacial acetic acid 2 parts of a mixture consisting of 40 P i of stofik emulslon fonslstmg of? 24.6 parts N,N-dimethyl-N,N-bis-octadecyl ammo- 1 Part 01816 acld ethanolamlde,

1 part oleylalcohol eicosaglycol ether,

4 parts water and i 6 parts perchloroethylene as well as 939 parts perchloroethylene with a liquor absorption of 100% and, without intermediate drying, steamed at 103C for 10 minutes. To remove the non-fixed dyestuff, the rope is rinsed in per- EXAMPLE 3 chloroethylene at 45C for 5 minutes and subsequently dried with hot air. A clear greenish yellow dyeing of good fastness properties is obtained without the occurrence of waste water.

nium chloride 17.5 parts oleic acid heptaglycol ether 57.9 parts of water in 45 1600 parts perchloroethylene. After drying, an intense red dyeing is obtained without the occurrence of waste water.

A polyacrylonitrile fabric is padded on a foulard with a thickened padding liquor consisting of r 30 parts of a dyestuff preparation consisting of 17.3 parts of the dyestuff salt of the formula EXAMPLE 5 elm e9 7 6 ,]-0H=0HN00m OlZHlbQ-SOJ H I OH: OCH:

25 parts butyrolactone and A fabric of anion-modified polyethylene terephthal- 57.7 parts perchloroethylene, 65 ate fibres is impregnated with a padding liquor consist- 3.5 parts glycerol monoacetate, in of 3.5 parts methylglycol acetate, parts of a dyestuff preparation consisting of 3 art nonylphenol decaglyC l th 15.7 parts of the dyestuff of the formula GHQ e 0111.01 1 CH=CHN/ 58.8 parts perchloroethylene and 25.5 parts butyrolactone, 1 part glacial acetic acid 40 parts of a stock emulsion consisting of:

1 part oleic acid ethanolamide, 1 part oleyl alcohol eicosaglycol ether, 4 parts water and 6 parts perchloroethylene as well as 899 parts perchloroethylene with a liquor absorption of 104% and, without intermediate drying, steamed at 115C for minutes. To remove the non-fixed dyestuff, the fabric is rinsed in perchloroethylene at 45C for 5 minutes. It is subsequently dried with hot air. A clear pink dyeing is obtained without the occurrence of waste water.

EXAMPLE 6 cmcnm-o H-0 0 0 lgilm 32 parts of a stock emulsion consisting of:

1 part oleyl alcohol heptadecaglycol ether,

1 part oleic acid etha'nolamide,

4 parts water and 6 parts perchloroethylene as well as 958 parts perchloroethylene with a liquor absorption of 64% and, without intermediate drying, steamed at 105C for 10 minutes. The fabric is subsequently rinsed in perchloroethylene at C for 5 minutes and then dried with hot air. A clear blue dyeing of good fastness properties is obtained without the occurrence of waste water.

EXAMPLE 7 A yarn of p0lyhexamethylene-diamine adipate threads is sprayed in stripes with a dyestuff solution consisting of parts of a dyestuff preparation consisting of 15 parts of the dyestuff of the formula and parts diethylene glycol monobutyl ether in 950 parts trichloroethylene dried and steamed at l03C for 15 minutes. The yarn is subsequently rinsedin trichloroe'thylene at 45C for 5 minutes and then dried by blowing with hot air. A clear yellow unlevel dyeing of good fastness properties is obtained without the occurrence of waste water.

1 1 l2 and 85 parts diethylene glycol monobutyl ether in ing point between 40C and 170C;

950 parts trichloroethylene 3. up to by weight of water based on said chloand, without intermediate drying, steamed at 103C for rinated hydrocarbon solvent; and I minutes. The combed material is subsequently 4. 0 to 5% by weight based on said chlorinated hyrinsed in trichloroethyleneat 45C for 5 minutes and 5 dro r n lvent f an emulsifier which forms then dried by blowing with hot; air. A clear green unat c e em sion in the presence of water level dyeing of good fastness properties is obtained. d rina d hydrocarbon Solvent;

B. subjecting the fiber material to a treatment with r r steam.

EXAMPLE 9 l0 2. The process of claim 1 in which the fiber material A fabric of poly-e-caprolactam is impregnated with a is subjected to an intermediate drying step before the padding liquor consisting of steam treatment step (B).

3.0 parts of the fluorescent dyestuff of the formula 3. The process of claim 1 in which the fiber material 1 part oleic acid ethanolamide, is rinsed with o nated hydrocarbon solvent to re- 1 part oleyl al h l h t d l l ether, move non-fixed dyestuff subsequent to the steam treat- 4 parts water and p I 99] parts trichloroethylene 4. The process of claim 1 m which said fiber material with a liquor absorption of 64% and steamed at 105C P W001} f polyamldel p y y onitrilecontainfor 15 minutes. The fabric is subsequently rinsed in tri- 8 amomc groups Selected t Sulflnlc aCld, sulfichloroethylene at room temperature for 4 minutes, ii carboxyl and P acld p p y ers then centrifuged and freed from the adhering solvent wit carboxyl or Sulfomc acld groups; or polyamlde with sulfonic acid groups.

5. The process of claim 1 in which the pad-liquor contains in addition to the amine salt or addition prod- Waste Wateruct (l) and the'chlorinated hydrocarbon solvent (2);

We claim: I (3) an auxiliary which assists in the fixing of the dye- 1. Pad steaming process for the continuous dyeing Stuff and printing of fiber material containing ionic groups comprising the steps of A. impregnating said fiber material which is selected from the group consisting of natural polyamides, synthetic polyamides, anionically modified synthetic polyamides, anionically modified polyacrylo- 40 -nitrile and anionically modified polyesters with by blowing with hot air. A strongly and evenly bright- 3O ened white fabric is obtained without the occurrence'of 6. The process of claim 1 in which the pad-liquor contains in addition to the amine salt or addition product (1) and the chlorinated hydrocarbon solvent (2); (3) an auxiliary which improvesthe levelness of the dyeing.

7. The process of claim 1 in which the pad-liquor pad liquor consisting essentially of a Solution of contains in addition to the amine salt or addition prodl a salt or addition product of a p p y uct (1) and the chlorinated hydrocarbon solvent (2);

pound and an ionic dyestuff having the opposite (3) 0.1 to 2 percent by weight of a lower carboxylic charge of the ionic groups on Said fiber material; acid based on the weight of chlorinated hydrocarbon solvent.

2. organic solvent said organic solvent consisting of The fiber material d by the process of claim a chlorinated hydrocarbon solvent having a boil-

Claims

2. organic solvent said organic solvent consisting of a chlorinated hydrocarbon solvent having a boiling point between 40*C and 170*C;
2. The process of claim 1 in which the fiber material is subjected to an intermediate drying step before the steam treatment step (B).
3. The process of claim 1 in which the fiber material is rinsed with chlorinated hydrocarbon solvent to remove non-fixed dyestuff subsequent to the steam treatment step (B).
3. up to 10% by weight of water based on said chlorinated hydrocarbon solvent; and
4. 0 to 5% by weight based on said chlorinated hydrocarbon solvent of an emulsifier which forms a thickened emulsion in the presence of water and chlorinated hydrocarbon solvent; B. subjecting the fiber material to a treatment with steam.
4. The process of claim 1 in which said fiber material is wool; synthetic polyamide, polyacrylonitrile containing anionic groups selected from sulfinic acid, sulfimide, carboxyl and phosphonic acid groups; polyesters with carboxyl or sulfonic acid groups; or polyamide with sulfonic acid groups.
5. The process of claim 1 in which the pad-liquor contains in addition to the amine salt or addition product (1) and the chlorinated hydrocarbon solvent (2); (3) an auxiliary which assists in the fixing of the dyestuff.
6. The process of claim 1 in which the pad-liquor contains in addition to the amine salt or addition product (1) and the chlorinated hydrocarbon solvent (2); (3) an auxiliary which improves the levelness of the dyeing.
7. The process of claim 1 in which the pad-liquor contains in addition to the amine salt or addition product (1) and the chlorinated hydrocarbon solvent (2); (3) 0.1 to 2 percent by weight of a lower carboxylic acid based on the weight of chlorinated hydrocarbon solvent.
8. The fiber material dyed by the process of claim 1.