US2952506A

US2952506A - Process for even and level dyeing of filament nylon fabrics

Info

Publication number: US2952506A
Application number: US605941A
Authority: US
Inventors: Dimitri D Dellis
Original assignee: Chemstrand Corp
Current assignee: Solutia Inc
Priority date: 1956-08-24
Filing date: 1956-08-24
Publication date: 1960-09-13
Anticipated expiration: 1977-09-13
Also published as: BE560259A; FR1181678A; ES234195A1; GB806026A; DE1153341B

Description

Unite atent r 2,952,506 Patented Sept. 13, 1960 fiice PROCESS FOR EVEN AND LEVEL DYEING OF FEAR/TENT NYLON FABRICS No Drawing. Filed Aug. 24, 1956, Ser. No. 605,941 Claims. (Cl. 8-55) This invention relates to the even dyeing of textile fabrics, and more particularly to the even and level dyeing of fabrics composed of filaments of a polycarbonamide, more familiarly known as nylon.

In the past the commercial practice of dyeing the synthetic linear polycarbonamides more familiarly known as nylon has been carried out by means of the dispersed or acetate dyestuifs. These dispersed dyestuffs have great covering power for nylon yarns and are not highly sensitive to the normal variations found in such yarns. However, the dispersed or acetate colors lack fastness to light and to Washing. In contrast, the anionic dyestufis best exemplified by the classes of acid and direct dyes have extremely good fastness to both light and washing on nylon. It has not been commercially feasible to utilize the anionic dyestutfs in the majority of nylon filament dyeings, however, since those dyestufis are extremely sensitive to variations between difierent fibers and different parts of the same fibers. Nylon yarns which have been spun at difierent times or from ditferent lots of polymer demonstrate these variations most clearly. Frequently yarns spun at different times are dyed to diiferent shades with the anionic dyestuflfs when dyed by standard dyeing procedures. As a result the nylon fabrics dyed with anionic dyes are often colored in an uneven fashion, showing streaks and shade depth variations in knitted goods, and barr elfects, warp streaks and the like in woven goods. The inability to secure even dyeing of nylon yarns and fabrics is believed to be due to slight variations in the chemical compositions of the parent polymers, to variations in orientation due to slight differences in the drawing to which the yarns are subjected either in spinning and processing of the yarn, or in the mechanical action of the textile machinery used in the knitting or weaving of the fabrics, and perhaps to other causes as well. This inability to evenly dye nylon yarns and fabrics with the anionic dyestulfs has curtailed the large scale use of such dyestuffs for dyeing the nylon materials on which they exhibit excellent light and wash fastness properties.

The primary object of the present invention is to provide a new and improved process for dyeing polycarbonamide textile articles. A further object is to provide a process for dyeing nylon yarns evenly and levelly by means of anionic dyestufis Without the resulting streaks and shade depth variation that have previously characterized the use of the anionic dyestuffs for the dyeing of nylon fabrics. Other objects will appear from the description hereinafter.

In general the objects of this invention are accomplished by the process of dyeing polycarbonamide textile articles which comprises dyeing the articles in an aqueous dyeba-th containing an anionic dyestufi selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes and a substituted imidazoline compound selected from the group consisting of (l) a salt of an imidazoline having the general. formula wherein R is selected from the group consisting of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals and R is an open aliphatic chain consisting of from ten to 18 carbon atoms, such as I-butyl-2-hexadecyl-irnidazoline, 1- benzyl-Z-hexadecyl imidazoline, 1-(2-hydroxyethy1)-2- heptadecyl-imidazoline, I-(Z-hydroxyethyl) 2 heptadecenyl-imidazoline, and l-(2-hydroxyethyl)-2-undecylimidazoline, (2) a quaternary imidazolinium compound having the general formula wherein R and R are selected from the group consisting of alkyl, phenyl, hydroxyalkyl and carboxyalkyl radicals, R is an open aliphatic chain consisting of from ten to 18 carbon atoms and X is a halogen, such as,l,ldi-(Z-hydroxyethyl)-2-heptadecyl imidazolinium chloride, 1,1-di-(2-hydroxyethyl) 2 heptadecenyl-imiclazolinium chloride, Z-tridecyl-l-hydroxyethyl-l-benzyl-imidazolinium chloride and 1,1-dibutyl-2-hexadecyl-imidazolinium chloride, and (3) a quaternary imidazolinium compound having the general formula EEC-N t wherein R and R are selected from the group consisting of hydroxyalkyl, alkali metal-substituted hydroxyalkyl, and alkali metal-substituted carboxyalkyl radicals and R is an open aliphatic chain consisting of from ten to 18 carbon atoms, such as l,l-di(2-hydroxyethyl)-2-heptadecyl imidazolinium hydroxide and the disodium salt of Z-nndecyl-l-(2-hydroxyethyl)-1-(carboxymethyl) imidazolinium hydroxide. It has now been found that quite even and level dyeings of nylon yarns and fabrics can be achieved by means of the anionic dyestuifs claimed above if the dyeing is carried out in an acidic dyebath containing a substituted imidazoline compound of one of the abovedescribed types.

The amount of the substituted imidazoline compounds which can be used in the process of the present invention can vary between one and ten times the weight of the dyestuffs employed. Many of the anionic dyestuffs suitable for use in the process may be used to dye nylon fabrics evenly and levelly when employing as little as one to two times the weight of the dyestufi of the substituted imidazoline compounds. However, with others of the anionic dyestuffs, although these amounts of the substituted imidazoline compounds give even dyeings from fiber to fiber they may result in unlevel dyeings, i.e. unequal penetration as between the fibers. With these dyestuffs both even and level dyeings of nylon fabrics may be acheived by increasing the ratio of the substituted imidazoline compounds to the dyestufit employed to a value of from about 6 to 10 times the weight of the dyestuff. Normally a ratio of approximately 41 to 6 times the weight of the dyestufl for the amount of the substituted imidazoline compounds is preferred.

The synthetic linear polycarbonamides, more familiarly known as nylons, to which the process of this invention is applicable are of the general type described in U.S. Patents 2,071,250; 2,071,253 and 2,130,948. The contemplated polycarbonamides comprise the reaction products of linear polymer-forming compositions containing amideforming groups, for example reaction materials consisting of bifunctional molecules containing two reactive groups which are complementary to reactive groups in other molecules and which include the. complementary amideforming groups. These polycarbonamides are of two distinct types. Those synthetic linear polycarbonamides which comprise the self-polymerization products of monoamino monocarboxycyclic acids containing at least five carbon atoms in the chain separating the amino and carboxyl' groups and those synthetic linear polycarbonamides derived from the reaction of suitable diamines with suitable dicarboxylic acids in substantially equimolar amounts. It is. to be understood that reference herein tothe amino acids, diamines, and dicarboxylic acids is intended to include the equivalent amide-forming derivatives of those reactants. Upon hydrolysis the amino acid polycarbonamides yield the amino acid hydrochloride, and the diamine-dicarboxyclic acid polycarbonamides yield the dicarboxyclic acid and the diamine hydrochloride. Further, the average number of carbon atoms separating the amide groupsin the polycarbonamides is at least two.

These polycarbonamides contain recurring amide r ps:

I II

wherein R is a member of the group of hydrogen and monovalent hydrocarbon radicals, as a part of main chain of atoms of the polymer. Particularly useful polycarbonamides in the present invention are the simple unsubstituted polycarbonamides, such as those formed by the reaction of tetramethylene diamine with adipic acid, tetramethylene diamine with suberic acid, tetrarnethylene diamine with sebacic acid, hexamethylene diamine with adipic acid, hexamethylene diamine with suberic acid, hexamethylene diamine with sebacic acid, or the polymerization product of epsilon-caprolactam. In addition, polymers formed from the reaction of two ormore di-. amines with dicarboxylic acids and/or two or more di carboxylic acids with diamines are contemplated in the practice of the-instant invention.

Most types of anionic dyestufis function with the process. of this invention. The two most common classes of anionic dyestuffs and two which give excellent light and wash fastness when used on nylons are the acid and direct dyes, but other classes of anionic dyestuffs may be employed in this process as well, such as acid metallized and mordant acid or chrome dyes. Thus, at least four of the recognized classes of anionic dyes, the direct dyes, the acid dyes, the acid metallized dyes and the mordant acid or chrome dyes can be successfully applied to nylons by the process of this invention. Examples of certain of the direct dyestuffs which have been successfully employed to dye nylon fabricslevelly and uniformly by the process of this invention include Paper Yellow 3GXA (CI 364), Chrysophenine (CI 365), Chlorantine Fast Yellow SGLL (CI 346), Calcodur Orange GL (CL 653), Calcodur Red SBL (CL 278), Triazol Fast Scarlet B (CI 382). Congo Red (CI 370), Diarnine Fast Red FA- CF (CI 419), and Diphenyl Violet EV Supra (CI 394). Examples of acid dyestufis which may be employed include Pontacyl Dark Green (CI 247), Amacid Red 3B (CI 280), Benzyl Red G (CI 275), Brilliant Croceine Scarlet MOO (CI, 252), Anthraquinone Violet 3RAv (CI 1080) and Alizarin Fast Light Blue C (CI 108-8). Examples of mordant acid or chrome dyestuifs which may be used include Omega Chrome Orange G (CI 274), Eriochrome Blue Black R (CI 202), Calcochrome Black T (CI 203), Chrome Yellow A (CI 219), and Calcochrome Alizarine Gray 2BLS (Pr. 206). Examples of acid metallized dyestufls which may be employed include Neolan Blue 2G (Pr. 144), Neolan Navy Blue RLG (Pr. 561), and Chromacyl Black W (Pr. 143). Not all dyestuffs of each class of anionic dyes enumerated will dye nylon yarns or fabrics equally as well, as is well known. However, the best dyes from among each class can easily be selected, and a large number of the dyestuffs in each named class can be effectively utilized to dye nylon materials evenly and levelly. by the process of this invention,

The conditions of dyeing employed in theprocess of the present invention are substantially those of the normal dyeing procedure with the particular classes of. anionic dyes employed. That is, with all of the named classes of anionic dyestuffs dyeing is usually carried out at a temperature of from about 200 to about 210 F. and at a pH of from about 2 to about 5.5. The preferred pH with the acid and direct dyestufi's is from about 3 to about 5.

The amount of dyestulf employed and the volumeof dye-.

bath are the same as those commonly used in the acid and direct dyeing of woolen, cellulosic and other type fibers. The length of time of the dyeing to result in even and, level dyeings of nylon is generally from about 1 to about 4 hours.

The mechanics of carrying out the dyeing are not. critical and may be varied to suit the normal dyeing practice. That is, the fabric may be entered into the bath cold and the bathslowly raised to dyeing temperature after all the ingredients have been added, or the fabric may be added to the bath first and the dyestufi and substituted imidazoline compound added afterwards. The order of addition of components to the dyebath, is a matter of choice.

Although the process of the present invention does not require the use of other dispersing agents inaddition to the dyestulf and the substituted imidazoline compounds.

referred to above, it is sometimes of advantage in obtaining greater levelling as well as eveness of dyeing to employ in the dyebath in addition to the named ingredients a non-ionic dispersing agent. Such non-ionic dispersing agents as those containing the condensation products. of polyglycols with higher fatty acids, higher fatty alcohols, amides of higher fatty acids, or long chain alkyl substituted phenols can be added to the dyebath of the present invention to assist in obtaining more level dyeings on certain nylon constructions. The non-ionic dispersingagents may be used in concentrations of from about 0.1% to about, 4%. The use of the non-ionic dispersing agents not only improves the levelness of penetration of the dyes from fiber to fiber but also insures that those fibers on the interior of the skein are evenly dyed with those on the exterior. Consequently, when dyeing certain closely woven fabrics such as taffetas it is preferred to include a non-ionic dispersing agent of the above-described type. in the dyebath.

It has also been found that the substituted imidazoline,

compounds are effective to convert an unevenly dyed nylon fabric to an evenly dyed one by subjecting the,

dyed fabric to an aqueous treatment therewith. Thus, an

unevenly dyed talfeta or chiffon fabric displaying streaks.

and shadevariations throughout the piececan be rendered even and level by treating for several hours in a bath containing one of the substituted. imidazoline. compounds for example, 1,1 di (2-hydroxyethyl) -2-heptadecenyl imidazolinium chloride, in the same general amounts that are used to evenly dye such fabrics by the process of this invention. The bath may be maintained at an acidic pH at or near the boil until the dyeing has become even and level. If such procedure is not suflicient to produce an even and level dyeing of verybadly streaked fabrics, it is also possible to treat the fabric in an alkaline bathcontaining one of the substituted imidazolme compounds and after the dyestuff originally prescut on the fabric has been substantially removed into solution, then adjusting the pH of the bath to an acidic pH and thereby effecting a redyeing of the fabric with the same dyestuif, but in a completely even and level manner. Although it is not required that such treating baths contain a non-ionic dispersing agent, the presence of such an agent, for example the condensation product of one mole of stearyl alcohol with 20 moles of ethylene oxide is preferred, since less of the substituted irnidazoline compound is required when a non-ionic dispersant is also present. By this means previously uneven dyeings can be converted to even dyeings on nylon fabrics and knitted goods.

The applications of the principles of this invention are more particularly illustrated in the examples below. Parts are by Weight unless otherwise stated.

EXAMPLE I A dyebath was prepared containing 0.25% Pontacyl Dark Green G (CI 247), 1.4% of 1,1-di-(2-hydroxyethyl)-2-heptadecenyl-imidazolinium chloride, and 5% glacial acetic acid in 40 volumes of water, all percentages being based on Weight of the fabric to be dyed. A specially knit nylon tricot was employed in the dyeing. This nylon tricot fabric was made up of seven different samples of nylon yarn, spun and drawn under different conditions so as to display different dyeing rates. The fabric was knit on a 14 gauge machine with 20 ends of each yarn sample knit side by side in the following order: (1) a sample of normal commercial 70 denier, 34 filament nylon yarn, (2) a sample of the same yarn count spun on a pilot plant spinning machine in the normal manner, (3) a sample of the same yarn drawn at a 3.2% higher than normal draw ratio, (4-) a sample of the same yarn drawn at a 2.6% lower than normal draw ratio, (5) a sample of the yarn spun from the same batch employing a higher than normal air flow in the spinning machine, (6) a sample of yarn spun from the same batch employing C. lower than normal temperature of the melt entering the spinneret, and (7) a sample of the same commercial 70 denier normally spun nylon yarn as in 1) above. The specially knit tricot fabric employed was knit from yarns having sufficient differences in the spinning and drawing thereof to demonstrate pronounced dilferences in shade upon dyeing with an acid or direct dyestuff. One part of the specially knit tricot fabric was entered into the bath and the temperature of the bath slowly raised to 200 F. The bath was held at this temperature for 3 hours. The shade depth variations between the seven different yarns making up the tricot fabric were hardly noticeable to the eye. The gray scale ratings of the differences at each knitting junction of the specially knit tricot fabric are based upon the International Geometric Grey Scale of the Society of Dyers and Colorists, wherein a rating of 5 represents negligible shade variation from the next proceding sample or section thereof, a rating of 4 represents noticeable variation, a rating of 3 represents appreciable variation, 2. rating of 2 represents considerable variation, a rating of 1 represents much variation and a plus or minus indicates slightly more or less than the given rating. The grey scale ratings of the fabric dyed in the above manner are set out in Table I below.

One part 'of the same specially knit nylon tricot fabric employed above was dyed in a dyebath containing 0.25%

Pontacyl Dark Green G (CI 247 and 5% of ammonium slowly to 200 acetate in 40 volumes of water, the percentages being based on the weight of the fabric dyed, in the same manner as above. The shade depth variations between the seven different yarns composing the specially knit tricot fabric were quite noticeable as between the yarns. The grey scale ratings of the difference at each knitting junc- A dyebath was prepared containing the following ingredients: 0.25% Pontacyl Dark Green G (CI 247), 0.5% of l,l-(2-hydroxyethyl)-2-heptadecenyl-imidazolinium chloride, and 16% glyceryl diacetate in 40 volumes of water, all percentages being based on the weight of the fabric to be dyed. One part of the same specially knit nylon tricot fabric as employed in Example I was entered into the dyebath. The temperature of the bath was raised to 200 F. and held at this temperature for minutes. The sample of the specially knit tricot fabric was levelly and evenly dyed and the shade depth variations were hardly noticeable to the eye.

EXAMPLE III A dyebath was prepared containing the following ingredients: 0.5% of Pontacyl Dark Green G (CI 247 2.5% of l,l-(Z-hydroxyethyl)2-heptadecenylirnidazolinium chloride, 5% glacial acetic acid and 40 volumes of water, all percentages being based on the Weight of the fabric to be dyed. One part of a nylon taffeta fabric was entered into the bath and the temperature of the dyebath was slowly raised to 200 F. and held there for 2 /2 hours. The taifeta was evenly and levelly dyed and the fabric was well penetrated with the acid dyestuif when treated by the procedure outlined above.

EXAMPLE IV A dyebath containing the following ingredients Was prepared: 0.5 of Diphenyl Brilliant Violet DB (Pr. 35), 1.0% of l-(2-hydroxyethyl)-2-undecylimidazolinium acetate, and 2% glacial acetic acid based on the weight of the fabric to be dyed. One part of nylon taffeta fabric was entered into the dyebath. The temperature of the bath was slowly raised to 200 F. and maintained at this temperature for two hours. The warp streaks present in the fabric were hardly noticeable.

The levelness of dying was improved by repeating the above dyeing with the exception of substituting formic for acetic acid for pH adjustment and adding 0.25% of the condensation product of 1 mole of stearyl alcohol and 20 moles of ethylene oxide.

EXAMPLE V A dyebath was prepared containing the following ingredients: 0.25% of Chromacyl Black W (Pr. 143), 1.0% of condensation product of 1 mole of oleyl alcohol condensed with 15 to 20 moles of ethylene oxide, 2.0% of glacial acetic acid, and 2.0% of 1,l-di-(2-hydroxyethyl)'- Z-heptadecenylimidazolinium chloride in 40 volumes of water based upon the Weight of the fabric to be dyed. One part of the specially knit nylon tricot fabric containing seven different yarns spun under different conditions was entered into the dyebath. The dyebath Was raised F. and maintained at that temperature for 2 hours. Differences in shade between knit junctions of the specially knit fabric were hardly noticeable.

7 EXAMPLE VI A dyebath was prepared containing the following ingredients: 0.25% Pontacyl Dark Green G (CI 247), 2.0% of formic acid, 2.0% of the condensation product of stearyl alcohol condensed with 20 moles of ethylene oxide, and 2.0% of 1,1-di-(2-hydroxyethyl)-2-heptadecylimidazolinium hydroxide in 40 volumes of water, all percentages being based on the weight of the fabric to be dyed. One part of the specially knit nylon tricot fabric knit from seven yarns of diiferent dyeing characteristics was entered into the dyebath. The temperature of the dyebath was slowly raised to 200 F. and maintained at that temperature for 2 /2 hours. The shade variations at the knitting junctions were hardly noticeable to the eye after the dyeing procedure outlined above.

EXAMPLE v11 A dyebath was prepared containing the following ingradients: 1.0% Omega Chrome Orange G (CI 247), 2.0% of formic acid, 1.0 percent of 1,1-di-(2-hydroxyethyl)-2-heptadecenyl-imidazolinium chloride, and 2.0% of the condensation product of 1 mole of stearyl alcohol condensed with 20 moles of ethylene oxide in 40 volumes of water, all percentages being based on the weight of the fabric to be dyed. One part of a nylon taffeta fabric Was entered into the dyebath and the dyebath temperature slowly raised to 200 F. This temperature was maintained for 1 hour and the fabric then Washed and dried. The warp streaks normally occurring in nylon taffeta when dyed with chrome dyestuffs were not noticeable to the eye, and the tatfeta was evenly and levelly dyed with good penetration.

It may be seen from the foregoing examples that the amount of the various anionic dyestuffs applied to the nylon fabrics by the methods of this invention are substantially those same quantities which may be applied by conventional methods. That is, the employment of the substituted imidazoline compound in the dyebath does not act to increase the susceptibility of the nylon fibers or fabrics to dyeing by these dyes, but on the contrary provides a method for applying the same dyes more uniformly and levelly than can be accomplished by the normal methods.

The foregoing description makes evident the fact that this invention provides a practical, economical and commercial process for effecting uniform and level application of the four classes of anionic dyestuffs demonstrating the best light and water fastness on nylon yarns and fabrics. This result has been achieved even though wide variations in the amount of dye absorption exist when these same anionic dyes are applied by conventional dyeing methods.

As many variations within the spirit and scope of this invention will occur to those skilled in art, it is to be understood that the invention is not limited to the specific embodiments thereof except as set forth in the appended claims.

I claim:

1. -A process for evenly dyeing polycarbonamide textile anticles which comprises dyeing the article in an aqueous acidic dyebath containing an anionic dyestufi. selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes, and from one to ten times the weight of the dyestuif of a substituted imidazoline compound selected from the group consisting of (1) a salt of an imidazoline having the general formula.

C-Ra

wherein R is selected from the group consisting of alkyl,

wherein R and R are selected from the group consisting of alkyl, phenyl, hydroxyalkyl and carboxyalkyl radicals, R is an open aliphatic chain consisting of from 10 to 18 carbon atoms and X is a halogen and (3) a quaternary imidazolinium compound having the general formula wherein R and R are selected from the group consisting of hydroxyalkyl, alkali metal substituted-hydroxyalkyl and alkali metal-substituted carboxyalkyl radicals, and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.

2. A process as defined in claim 1 wherein the anionic dyestuif is a direct dye.

3. A process as defined in claim 1 wherein the anionic dyestutf is an acid dye.

4. A process as defined in claim dyestufi is an acid metallized dye.

5. A process as defined in claim 1 wherein the anionic dyestulf is a mordant acid dye.

6. A process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestuff selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes and from one to ten times the weight of the dyestuif of a salt of an imidazoline having the general formula 1 wherein the anionic wherein R is selected from the group consisting of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals, and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.

7. A process as described in claim 6 wherein the dyebath is maintained at a pH of from 2.0 to 5.5 and a temperature of from 200 to 210 F. and the dyeing is carried out for 1 to 4 hours.

8. A process as described in claim 6 wherein the salt of the imidazoline is 1-(2-hydroxyethyl)-2-undecylimidazoliniurn acetate.

9. A process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestulf selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes and from one to ten times the weight of the dyestuif of a quaternary imidazolinium compound having the general formula wherein R and R are selected from the group consisting of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals, R is an open aliphatic chain consisting of from ten to 18 carbon atoms, and X is a halogen.

10. A process as described in claim 9 wherein the dyebath is maintained at a pH of from 2.0 to 5.5 and a 9 temperature of from 200 to 210 F. and the dyeing is carried out for one to four hours.

11. A process as described in claim 9 wherein the quaternary imidazolinium compound is 1,l-di-(2-hydroxyethyl) -2-heptadecenyl-imidazolinium chloride.

12. A process as defined in claim 9 wherein the quaternary imidazolinium compound is 1,1-di-(2-hydroxy ethyl)-2-undecyl-imidazolinium chloride.

13. A process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes and from one to ten times the weight of the dyestulf of a quaternary imidazolinium compound having the general formula wherein R and R are selected from the group consisting of hydroxyalkyl, alkali metal-substituted hydroxyalkyl and alkali metal-substituted carboxyalkyl radicals and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.

14. A process as described in claim 13 wherein the dyebath is maintained at a pH of from 2.0 to 5.5 and a temperature of from 200 to 210 F. and the dyeing is carried out for 1 to 4 hours.

15. A process as described in claim 13 wherein the quaternary imidazolinium compound is 1,1-di-(2-hydroxy ethyl)-2-heptadecyl-imidazolinium hydroxide.

16. A process as described in claim 13 wherein the quaternary imidazolinium compound is the disodium salt of 1-(2-hydroxyethyl)-1-carboxyethyl undecyl-imida zd linium hydroxide.

17. A process for evenly dyeing polycarbonamide textile articles which comprises dyeing the article in an aqueous acidic dyebath containing an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes, from 0.1 percent to 4.0 percent of a non-ionic dispersing agent selected from the group consisting of the condensation products of polyglycols with higher fatty acids, the condensation products of polyglycols with higher fatty alcohols, and long chain alkyl-substituted phenols, and from one to ten times the weight of the dyestuff of a substituted imidazoline compound selected from the group consistring of (l) a salt of an imidazoline having the general formula wherein R is selected from the group consisting of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms, (2) a quaternary imidazolinium compound having the general formula wherein R and R are selected from the group consisting of alkyl, phenyl, hydroxyalkyl and carboxyalkyl radicals, R is an open aliphatic chain consisting of from 10 to 1 0 18 carbon atoms and X is a halogen and 3) a quaternary imidazolinium compound having the general formula Ha -N 0H- H: -N

34 Ra wherein R and R are selected from the group consisting of hydroxyalkyl, alkali metal substituted-hydroxyalkyl and alkali metal-substituted carboxyalkyl radicals, and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.

18. A process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes, from 0.1 percent to 4.0 percent of a non-ionic dispersing agent which is a condensation product of ethylene oxide with a higher fatty alcohol, and from one to ten times the weight of the dyestutf of a salt of an imidazoline having the general formula wherein R is selected from the group consisting of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals, and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.

19. A process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes, from 0.1 percent to 4.0 percent of a non-ionic dispersing agent which is a condensation product of ethylene oxide with a higher fatty alcohol, and'from one to ten times the weight of the dyestuif of a quaternary imidazolinium compound having the general formula wherein R and R are selected from ing of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals, R is an open aliphatic chain consisting of from ten to 18 carbon atoms, and X is a halogen.

20. A process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes, from 0.1 percent to 4.0 percent of a non-ionic dispersing agent which is a condensation product of ethylene oxide with a higher fatty alcohol, and from one to ten times the weight of the dyestuif of a quaternary imidazolinium compound having the general formula the group consistwherein R and R are selected from the group consisting of hydroxyalkyl, alkali metal-substituted hydroxyalkyl and alkali metal-substituted carboxyalkyl radicals and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.

(References on following page) 1 1 References Cited in the file of this patent UNITED STATES PATENTS 2,043,164 Grgnacher June 2, 1936 2,083,182 Zweifel June 8, 1937 2,268,273 Wilkes Dec. 30, 1941 Douglas p. 122.

12 MacGregor Mar. 13, 1945' Smith July 19, 1955 Mooradia'n Nov. 8, 1955 OTHER REFERENCES Amer. Dyestuff Rep., February 19, 1951,

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent N0a 2,952 506 September 13 1960 Dimitri D., Dellis Column 5 lines 55 and 56 for "proceding" read receding column 7 line l9 for "247" read 274 Signed and sealed this 11th day of April 1961.,

(SEAL) Attest:

Attesting Oflicer Acting Commissioner of Patents

Claims

1. A PROCESS FOR EVENLY DYEING POLYCARBONAMIDE TEXTILE ARTICLES WHICH COMPRISES DYEING THE ARTICLE IN AN AQUEOUS ACIDIC DYEBATH CONTAINING AN ANIONIC DYESTUFF SELECTED FROM THE GROUP CONSISTING OF DIRECT DYES, ACID DYES ACID METALLIZED DYES, AND MORDANT ACID DYES, AND FROM ONE TO TEN TIMES THE WEIGHT OF THE DYESTUFF OF A SUBSTITUTED IMIDAZOLINE COMPOUND SELECTED FROM THE GROUP CONSISTING OF (1) A SALT OF AN IMIDAZOLINE HAVING THE GENERAL FORMULA.