US20050022310A1

US20050022310A1 - Process for treating solvent-spun, cellulosic fibres

Info

Publication number: US20050022310A1
Application number: US10/832,693
Authority: US
Inventors: Andrew Renfrew
Original assignee: Lenzing AG
Current assignee: Lenzing AG
Priority date: 2001-11-02
Filing date: 2004-04-22
Publication date: 2005-02-03
Also published as: CN1578854A; TR200400926T2; WO2003038164A3; KR100927184B1; KR20050042027A; EP1440190A2; JP2005507035A; WO2003038164A2; CN1270004C; AU2002342379A1; ATE417952T1; PT1440190E; ES2319623T3; EP1440190B1; BR0213716A; AT413824B; DE50213134D1; ATA17312001A; TW200300186A; BR0213716B1

Abstract

The invention relates to a process for treating solvent-spun, cellulosic fibres, wherein the fibres are contacted with a textile auxiliary agent in an alkaline environment. The process according to the invention is characterized in that a compound of the general formula

or a salt thereof, respectively, is used as the textile auxiliary agent, wherein

R₁is a bridging link selected from the group consisting of a linear or branched chain comprising 1 to 4 C-atoms and phenyl,
R₂and R₃are the same or different and are selected from the group consisting of (CH₂)_m—CH═CH₂with m=0 to 2, and wherein R₄denotes a ionic group and/or a group ionizable in an alkaline environment.

Description

The invention relates to a process for treating cellulose fibres and assemblies made of those cellulose fibres, wherein the fibres or the fibre assemblies, respectively, are contacted with a textile auxiliary agent in order to impart improved properties to the fibres.
As an alternative to the viscose process, in recent years there have been described a number of processes wherein cellulose, without forming a derivative, is dissolved in an organic solvent, a combination of an organic solvent and an inorganic salt, or in an aqueous saline solution. Cellulose fibres made from such solutions are called “solvent-spun fibres” and have received by BISFA (The International Bureau for the Standardisation of man made Fibres) the generic name Lyocell. As Lyocell, BISFA defines a cellulose fibre obtained by a spinning process from an organic solvent. By “organic solvent”, BISFA understands a mixture of an organic chemical and water. “Solvent-spinning” is supposed to mean dissolution and spinning without derivatization.
So far, however, only a single process for the production of a solvent-spun cellulose fibre has achieved industrial-scale realization. In this process a tertiary amine-oxide, particularly N-methylmorpholine-N-oxide (NMMO), is used as a solvent. Such a process is described for instance in U.S. Pat. No. 4,246,221 and provides fibres which are distinguished by a high tensile strength, a high wet-modulus and a high loop strength.
However, the usability of textile fabrics, for instance woven fabrics, produced from the above-mentioned fibres, is restricted to a large extent by those fibres' pronounced tendency to fibrillate in the wet state. Fibrillation means the breaking up of the fibre in longitudinal direction at mechanical stress in the wet state, whereby the fibre assumes a hairy, furry appearance. In the course of a couple of washings, a dyed fabric produced from those fibres loses a great deal of its colour intensity. Add to this that bright streaks develop in edges created by scouring and crumpling. The reason for fibrillation is thought to be that the fibre consists of fibrils arranged in the direction of the fibre, with crosslinking existing between them only to a small extent.
Furthermore, streak formation may also occur if the fibres are dyed in the form of tows. In textile areas, the formation of knots may result from friction in the dry state, which property is known as “pilling”.
WO 92/07124 describes a process for the production of a fibre having a reduced tendency to fibrillation, according to which the freshly spun, i.e. not yet dry, fibre is treated with a cationic polymer. As such a polymer, a polymer comprising imidazole and azetidine groups is mentioned. In addition, furthermore a treatment with an emulsifiable polymer, such as polyethylene or polyvinyl acetate, or also a crosslinking with glyoxal may take place.
In a lecture given by S. Mortimer at the CELLUCON conference in 1993 in Lund, Sweden, it was mentioned that the tendency to fibrillation rises as drawing is increased.
EP-A 0 538 977 and WO 94/09191 as well as WO 95/28516 describe a process of the initially mentioned kind, wherein solvent-spun fibres are contacted with a textile auxiliary agent in order to decrease the tendency to fibrillation.
WO 94/24343 describes a process for the production of cellulose fibres having a decreased tendency to fibrillation, wherein a solution of cellulose is spun to fibres in a tertiary amine oxide and the freshly spun fibres are contacted with a textile auxiliary agent carrying at least two reactive groups and are washed with an aqueous buffer, with glyoxal not being used as the textile auxiliary agent. According to this previously known process, the freshly spun fibres are contacted with the textile auxiliary agent best in an alkaline environment.
Furthermore, it is known that, for the manufacture of washproof woven and knitted fabrics, fibre assemblies made of solvent-spun fibres may be crosslinked with methylol compounds. However, it has turned out to be impossible to prevent scouring edges from forming during dyeing when using those compounds. For that purpose, crosslinking would have to occur prior to dyeing or at least during dyeing. However, methylol compounds and also the other classic permanent finishing agents are hardly suitable for this. A further disadvantage of the methylol compounds is the formation of formaldehyde, leading to an impairment of the workplace.
Further processes for treating cellulose fibres of the genus Lyocell are known, for instance, from WO 97/49856, the Austrian Utility Model no. 2527 and WO 99/19555.
However, the processes suggested in the prior art for treating cellulose fibres of the genus Lyocell exhibit a number of disadvantages:
For instance, a great number of the textile auxiliary agents suggested up to now are very tedious in their manufacture and hence are expensive. With other textile auxiliary agents, it may be observed that they are subject to hydrolysis in the alkaline environment necessary for the reaction with the cellulose. Therefore, losses of hydrolysis occur. Furthermore, many of the proposed textile auxiliary agents are not soluble enough in the necessary alkaline environment and must be used in the form of a dispersion. This can lead to irregular treatment effects. Finally, it must be mentioned that the use of some known textile auxiliary agents is difficult because of their toxicity.
The present invention aims at providing a process for treating cellulose fibres of the genus Lyocell and assemblies made of those fibres, which process may be realized in a simple manner and makes it possible that the treated fibres exhibit a decreased tendency to fibrillation or that the treated fibre assemblies, respectively, exhibit improved scouring and pilling values.
The process according to the invention for treating solvent-spun fibres, wherein the fibres are contacted with a textile auxiliary agent, is characterized in that a compound of the general formula

or a salt thereof, respectively, is used as the textile auxiliary agent, wherein

R₁is a bridging link selected from the group consisting of a linear or branched chain comprising 1 to 4 C-atoms and phenyl,
R₂and R₃are the same or different and are selected from the group consisting of (CH₂)_n—CH═CH₂with m=0 to 2, and wherein R₄denotes a ionic group and/or a group ionizable in an alkaline environment.

Surprisingly, it was found that the textile auxiliary agents used according to the invention, which are available at relatively low costs, give rise to an improvement of the properties of the treated fibres to the same or even to a larger extent as do, for instance, the substances known from EP-A 0 538 977, which are to be manufactured with effort.
Furthermore, it was found that the substances used according to the invention are extremely resistant to hydrolysis in an alkaline environment. Therefore, in comparison with the textile auxiliary agents disclosed, for instance, in the Austrian Utility Model no. 2527 or in WO 99/19555, no losses of hydrolysis occur in the course of the treatment. For that reason, less textile auxiliary agent is needed in order to achieve equivalent or even better properties of the treated fibres.
In the processes described in WO 94/09191 and WO 95/28516, respectively, a 1,3,5-trisacryloyl tetrahydro-1,3,5-triazine as well as N,N′-methylene bisacrylamide are used as textile auxiliary agents. Those textile auxiliary agents are present in nonionic form. As opposed to that, the compounds used according to the invention are present in ionic and dissolved form in an aqueous alkaline environment.
Also, the compounds used according to the invention are volatile only to a small extent or not at all.
Preferably, the residue R₄is selected from the group consisting of-SO₃H, —COOH, —OH and —SH.
Furthermore, R₂and R₃both preferably mean (CH₂)_m—CH═CH₂in the textile auxiliary agent used.
A textile auxiliary agent used with particular preference is a compound of the formula

or a salt thereof, respectively.
Furthermore, a compound of the formula

or a salt thereof, respectively, is used preferably as a textile auxiliary agent.
A compound of the formula

i.e. the 2,4-bis(acrylamido)benzene sulfonic acid, or a salt thereof, respectively, is used with particular preference as a textile auxiliary agent.
In a further preferred embodiment, a compound of the formula

or a salt thereof, respectively, is used as a textile auxiliary agent.
The use of a compound of the formula

i.e. of the bisacrylamido acetic acid, or a salt thereof, respectively, as a textile auxiliary agent is particularly preferred.
Preferably, the textile auxiliary agent is used in the form of the sodium, lithium, potassium, calcium or magnesium salt. But also other salts, in particular metallic salts, may be used.
In the process according to the invention, the fibres preferably are contacted with an alkaline solution of the textile auxiliary agent.
A particularly interesting and inexpensive variant of the process according to the invention consists in that an alkaline solution of a compound of the formula

wherein R₅and R₆both are (CH₂)_n—X, n=2 to 4, X=halogen, is produced and that, prior to or during contacting with the fibres, this compound in an alkaline solution is reacted to a textile auxiliary agent according to formula (I), wherein R₂and R₃both mean (CH₂)_m—CH═CH₂, wherein m=n−2.
Thus, prior to or during contacting with the fibres, the compound used according to the invention is prepared in the impregnating solution virtually in situ by producing the two acrylamido groups from the respective ω-halogen alkyl compound by means of an elimination reaction.
In case of the preferably used 2,4-bis(acrylamido)benzene sulfonic acid (or, e.g., of its sodium salt, respectively), it can be produced in the impregnating solution directly from the sodium salt of the 2,4-bis(3-chloropropionamido)benzene sulfonic acid.
Preferably, the process according to the invention is carried out for the treatment of fibres which are provided in the never-dried state.
For the continuous treatment of never-dried, solvent-spun fibres, the cut fibres washed free from NMMO and having a defined moisture of from 50% to 500% adjusted, for instance, by squeezing may be contacted in a loose structure (“fleece”) on a moving screen belt with the bath containing the textile auxiliary agent and may be soaked, for instance, by spraying (“impregnation”). The fleece has a weight per unit area of 0.2-15 kg/m², preferably of between 1 and 8 kg/m², based on the dry fibre, whereby the retention time of the fibre in that field of impregnation may amount to between 1 and 25 min, preferably, however, to from 2 to 10 min. The impregnation of the fibre can be effected only from one side but also from both sides of the fleece, whereby the ratio between fibre and treatment bath (kg/kg) may amount to from 1:1 to 1:50. In doing so, the textile auxiliary agent can be applied in a mixture with or separate from the catalyst which optionally is necessary.
After impregnation, the fleece is squeezed to a defined moisture of from 50% to 500%, the squeezed treatment bath is returned to the impregnation cycle and the temperature of the fleece is adjusted by suitable means, preferably by hot water vapour, and is maintained, whereby the retention time may amount to about 2-15 min. In doing so, the fibre heats up along with the bath to the desired temperature and the cellulose reacts with the textile auxiliary agent. Preferably, the treatment is carried out such that the fibre is thereby not dried.
Subsequently, the fibre is washed free from non-fixed reaction products, if possible under neutralization. With basically catalyzed crosslinking agents, an acidified washing bath may be used for that in the first washing stages. The number of washing stages complies with the employed concentrations and/or the washing efficiency of the individual stages.
The textile auxiliary agents used according to the invention are excellently suitable also for the treatment of already dried fibres and for the treatment of fibre assemblies, such as yarns, woven or knitted fabrics, containing solvent-spun fibres. The fibres may be provided in dyed or undyed form.
Furthermore, the present invention relates to the use of a compound of the formula

wherein R₁, R₂, R₃and R₄have the above-indicated meaning, or of a salt thereof, respectively, as a textile auxiliary agent for the treatment of solvent-spun fibres.
Thereby, the compounds of formula (I) are particularly suitable for decreasing the tendency to fibrillation of solvent-spun fibres.
However, the compounds of formula (1), in particular those in which R₁is phenyl, were surprisingly also found to cause the increase of the ultraviolet absorption of solvent-spun fibres.
The present invention furthermore relates to solvent-spun fibres which are obtainable in accordance with the process according to the invention as well as to fibre assemblies containing such solvent-spun fibres.
The textile auxiliary agents used according to the invention, in which the residue R₁is phenyl, are new compounds. Therefore, the invention furthermore relates to a compound of the formula

wherein R₂, R₃and R₄each have the above-indicated meaning, as well as to the salts thereof, provided that

- if R₄═—OH and R₂and R₃both are —CH═CH₂, the two amide groups are not in para-position to each other,
- if R₄═—SO₃H, R₂and R₃both are —CH═CH₂and the two amide groups are in ortho-position to each other, the calcium salt is excluded.

The N,N′-(2-hydroxy-1,4-phenylene)-bis-2-propenamide is registered in the “Chemical Abstracts” (American Chemical Society) under registration no. 105298-66-6.
The calcium salt of the 3,4-bis-[(1-oxo-2-propenyl)amino]benzene sulfonic acid is registered in the “Chemical Abstracts” (American Chemical Society) under registration no. 58772-33-1.
The compounds according to the invention may be produced in that a compound of the formula

is reacted with a compound of the formula

wherein R₂, R₃and R₄each have the above-indicated meanings, and the product obtained optionally is converted to the form of a salt.
The compounds of formula (II) may be produced in that a compound of the formula

wherein R₅and R₆both are (CH₂)_n—X, n=2 to 4, X=halogen, is reacted in an alkaline solution to a compound according to formula (II), wherein R₂and R₃both mean (CH₂)_m—CH═CH₂, wherein m=n−2.
The compounds of formula (X) are new as well. They may be produced in that a compound of the formula

is reacted with a compound of the formula

wherein R₄, R₅and R₆have the above-indicated meanings, and the product obtained optionally is converted to the form of a salt.

EXAMPLES

Example 1

Preparation of 2,4-bis(acrylanido)benzene Sulfonic Acid-Sodium Salt

In a 5 l beaker with an automatic stirrer, 66 g of KH₂PO₄and 3 g of Na₂HPO₄were dissolved in 1. 5 l of H₂O (pH=6.4). After adding 100 g (=0.53 mol) of 2,4-diaminobenzene sulfonic acid, the solution was cooled to <1° C. by the introduction of ice. Within 70 min, 260 ml (=233 g=2.58 mol) of acrylic-acid chloride was dropped in through a drip funnel, and by adding a 20% NaOH solution the pH value was adjusted to approximately 3.5 (pH values of below 3 and above 4 are to be avoided). By the introduction of ice, the temperature of the solution was kept at <1° C. When adding was completed (final volume=5 l), stirring was carried out for 1 h, whereby the solution was allowed to heat up to room temperature (RT).
After the neutralization with NaOH, the small amount of white solid was filtered off from the black solution, enough NaCl was added to the filtrate for a 20% solution to emerge, and the solution was stirred slowly overnight. The nascent grey precipitate was filtered off, was washed with a 20% NaCl solution and dried in the drying cabinet at approximately 65° C. (for about 24 h).
The final product was analyzed by means of HPCL and an NMR spectroscopy.
Yield: 152 g (=90% d. Th.) 2,4-bis(acrylamido)benzene sulfonic acid-sodium salt.

Example 2

Preparation of 2.4-bis(3-chloropropionamido)benzene sulfonic acid-sodium salt:

38.8 g of 2,4-diaminobenzene sulfonic acid (manufacturer BASF) was dispersed in 600 ml of water and was stirred. The pH value was adjusted to 6.5 by means of dissolved NaOH.
After cooling down to 10° C., 5.3 g of 3-chloropropionyl chloride was added dropwise (0.5 h), whereby the temperature was kept at 5-10° C. and the pH value was kept at 3.0-3.5. When adding was finished, it was determined by thin-layer chromatography that traces of the monoacylated product were still present. Therefore, another 13 g of acid chloride was added in order to complete the reaction. After raising the pH value to 5, 20% w/v of a NaCl solution was used for salting out, and the grey solid formed was filtered off. The cake was washed with 150 ml of a sodium chloride solution (20% w/v) and was oven-dried at 65° C., wherefrom 146 g of a product was obtained.

Example 3

Solvent-spun fibres produced according to the process described in WO 93/19230 and having a titre of 1.3 dtex were treated as follows in the never-dried state: At a bath ratio of 1:10, the fibres were impregnated with a solution, containing 50 g/l of sodium salt of the 2,4-bis(acrylamido)benzene sulfonic acid and 100 g/l of sodium sulfate, for 4 minutes at 30° C. Thereupon, 4 g/l of NaOH was added, and impregnation was continued for another 2 minutes. The solution had a pH value of 12.7. Subsequently, the fibres were squeezed to a moisture content of 100%-110% by means of a squeezer and were heat-treated with saturated steam (100%) at 100° C. for 4 minutes, were washed out and dried.
The degree of fibrillation of the fibres was determined by way of the wet abrasion resistance (testing method in accordance with WO 99/19555) of the individual fibres. According to this testing method, the sample treated according to the invention turns out to exhibit an average value of 560 revolutions. Compared with that, an untreated fibre exhibits a wet abrasion value of only 40-60 revolutions. The nitrogen content of the treated fibres amounts to 0.34%.

Example 4

At a bath ratio of 1:10, never-dried, solvent-spun fibres having a titre of 1.3 dtex were impregnated with a solution, containing 50 g/l of sodium salt of the 2,4-bis(acrylamido)benzene sulfonic acid and 50 g/l of sodium sulfate, to which shortly before impregnation 4 g/l of NaOH had been added, for 2 minutes at room temperature (RT) (pH value of the solution 12.7). Thereupon, the fibres were squeezed to a moisture content of 100%-110% by means of a squeezer (Foulard), were heat-treated with saturated steam for 6 minutes, were washed out and dried.
The determination of the wet abrasion resistance of the fibres treated in this manner yielded an average value of 1180 revolutions. The nitrogen content of the fibres amounts to 0.38%.

Example 5

In Situ-generation of 2,4-bis(acrylamido)benzene Sulfonic Acid

A solution, containing 50 g/l of sodium salt of the 2,4-bis(3-chloropropionamido)benzene sulfonic acid, is mixed with 10 g/l of sodium hydroxide at 30° C. and is stirred for 20 minutes at this temperature. In that solution, never-dried, solvent-spun fibres (titre 1.3 dtex) were impregnated at a bath ratio of 1:10 for more than 2 minutes at 30° C. Thereupon, 100 g/l of sodium sulfate was dissolved in the impregnating solution, and after 2 minutes 4 g/l of NaOH was added. After another 4 minutes of impregnation at 30° C., the fibres were squeezed to a pick-up of 100%-110%, were heat-treated with saturated steam for 4 minutes, were washed out and dried.
The determination of the wet abrasion resistance of the fibres treated in this manner yielded an average value of 780 revolutions. The nitrogen content of the fibres amounts to 0.34%.

Example 6

In Situ-generation of 2,4-bis(acrylamido)benzene Sulfonic Acid

A solution, containing 50 g/l of sodium salt of the 2,4-bis(3-chloropropionamido)benzene sulfonic acid, was mixed with 10 g/l of sodium hydroxide at 30° C. and was stirred for 20 minutes at this temperature. In that solution, 100 g/l of sodium sulfate and 4 g/l of NaOH were dissolved. At a bath ratio of 1:10, a piece of that fleece made of never-dried, solvent-spun fibres (titre 1.3 dtex) was impregnated in that solution for 4 minutes at 30° C.
Thereupon, the piece of fleece was squeezed to a pick-up of 100%-110%, was heat-treated with saturated steam for 4 minutes, was washed out and dried.
The determination of the wet abrasion resistance of the fibres treated in this manner yielded an average value of 570 revolutions. The nitrogen content of the fibres amounts to 0.39%.

Example 7

At a bath ratio of 1:30, a dyed knitted fabric made of solvent-spun fibres was impregnated with an aqueous solution, containing 50 g/l of sodium salt of the 2,4-bis(acrylamido)benzene sulfonic acid and 50 g/l of sodium sulfate, to which shortly before impregnation 4 g/l of NaOH had been added, for 2 minutes at room temperature (RT) (pH value of the solution 12.7). By means of a Foulard, the excess solution was squeezed out at 1 bar. For 5 minutes, the knitted fabric was heat-treated with water vapour at 100° C. Subsequently, the knitted fabric was washed repeatedly with 2% acetic acid and water and was finally dried.
Individual fibres of the knitted fabric were prepared and subjected to a wet abrasion test. The mean value of the wet abrasion test amounted to 650 revolutions.

Example 8

An undyed knitted fabric made of solvent-spun fibres was treated as described in Example 7 and was subjected to a wet abrasion test. The mean value of the wet abrasion test amounted to 620 revolutions.

Example 9

A solution, containing 60 g/l of bisacrylamido acetic acid, was mixed with 21 g/l of sodium hydroxide at 30° C., was stirred, and never-dried, solvent-spun fibres having a titre of 1.3 dtex were immediately added to that solution at a bath ratio of 1:10 and were then impregnated for 2 min. at 50° C. Thereupon, 100 g/l of sodium sulfate was added to that solution, and impregnation was continued for another 3 min. at 50° C. Thereupon, squeezing was carried out to a pick-up of 100-110%, and 4 minutes of heat-treatment with saturated steam, washing-out and drying were effected.
The wet abrasion resistance of the individual fibre yielded an average value of 700 revolutions. The nitrogen content of the fibre amounted to 0.33%.

Example 10

A solution, containing 60 g/l of bisacrylamido acetic acid, was mixed with 21 g/l of sodium hydroxide at room temperature, was stirred, and never-dried, solvent-spun fibres having a titre of 1.3 dtex were immediately added to that solution at a bath ratio of 1:10 and were then impregnated for 2 min. at room temperature. Thereupon, 100 g/l of sodium sulfate was added to that solution, and impregnation was continued for another 3 min. at 50° C. Thereupon, squeezing was carried out to a pick-up of 100-110%, and 4 minutes of heat-treatment with saturated steam, washing-out and drying were effected.
The wet abrasion resistance of the individual fibre yielded an average value of 400 revolutions. The nitrogen content amounted to 0.32%.

Example 11

A solution, containing 60 g/l of bisacrylamido acetic acid, was mixed with 21 g/l of sodium hydroxide at room temperature, was stirred, and never-dried, solvent-spun fibres having a titre of 1.3 dtex were immediately added to that solution at a bath ratio of 1:10 and were then impregnated for 5 min. at room temperature. Thereupon, squeezing was carried out to a pick-up of 100-110%, and 4 minutes of heat-treatment with saturated steam, washing-out and drying were effected.
The wet abrasion resistance of the individual fibre yielded an average value of 320 revolutions. The nitrogen content of the fibre amounted to 0.31%.

Claims

1-21. (Cancelled)

22. A process for treating solvent-spun, cellulosic fibers comprising contacting the fibers with a textile auxiliary agent in an alkaline environment, wherein the textile auxiliary agent has a general formula (I)

or is a salt thereof,

wherein R₁is a bridging link selected from the group consisting of a linear or branched chain comprising 1 to 4 C-atoms and phenyl,

wherein R₂and R₃are the same or different and are selected from the group consisting of (CH₂)_m—CH═CH₂with m=0 to 2, and

wherein R₄denotes a ionic group and/or a group ionizable in an alkaline environment.

23. The process according to claim 22, wherein R₄is selected from the group consisting of —SO₃H, —COOH, —OH and —SH.

24. The process according to claim 22, wherein R₂and R₃are (CH₂)_m-CH═CH₂.

25. The process according to claim 23, wherein R₂and R₃are (CH₂)_m—CH═CH₂.

26. The process according to claim 22, wherein the textile auxiliary agent has a formula (II)

or is a salt thereof.

27. The process according to claim 23, wherein the textile auxiliary agent has a formula (II)

or is a salt thereof.

28. The process according to claim 24, wherein the textile auxiliary agent has a formula (II)

or is a salt thereof.

29. The process according to claim 26, wherein the textile auxiliary agent has a formula (III)

or is a salt thereof.

30. The process according to claim 27, wherein the textile auxiliary agent has a formula (IV)

or is a salt thereof.

31. The process according to claim 28, wherein the textile auxiliary agent has

or is a salt thereof.

32. The process according to claim 22, wherein the textile auxiliary agent has a formula (V)

or is a salt thereof.

33. The process according to claim 23, wherein the textile auxiliary agent has a formula (V)

or is a salt thereof.

34. The process according to claim 24, wherein the textile auxiliary agent has a formula (V)

or is a salt thereof.

35. The process according to claim 32, wherein the textile auxiliary agent has a formula (VI)

or is a salt thereof.

36. The process according to claim 33, wherein the textile auxiliary agent has a formula (VI)

or is a salt thereof.

37. The process according to claim 34, wherein the textile auxiliary agent has a formula (VI)

or is a salt thereof.

38. The process according to claim 22, wherein the textile auxiliary agent is in the form of the sodium, lithium, potassium, calcium or magnesium salt.

39. The process according to claim 22, wherein the fibers are contacted with an alkaline solution of the textile auxiliary agent.

40. The process according to claim 22, further comprising providing a compound of the formula (VII)

wherein R₅and R₆both are (CH₂)_n—X, n=2 to 4, X=halogen; reacting the compound of formula (VII) to a textile auxiliary agent according to formula (I) prior to or during contacting the fibers with the textile auxiliary agent according to formula(I), wherein R₂and R₃both mean (CH₂)_m-CH═CH₂, wherein m=n−2.

41. The process according to claim 22, wherein the fibers are provided in the never-dried state.

42. The process according to claim 22, wherein the fibers are provided as fiber assemblies or as a component of a fiber assembly

43. Solvent-spun cellulose fibers treated by a process comprising contacting the fibers with a textile auxiliary agent in an alkaline environment, wherein the textile auxiliary agent has a general formula (I)

or is a salt thereof,

44. A fiber assembly containing solvent-spun cellulose fibers treated by a process comprising contacting the fibers with a textile auxiliary agent in an alkaline environment, wherein the textile auxiliary agent has a general formula (I)

or is a salt thereof,

wherein R₂and R₃are the same or different and are selected from the group consisting of (CH₂)_m—CH═CH₂with m=0 to 2,

wherein R₄denotes a ionic group and/or a group ionizable in an alkaline environment, and wherein the fibers are provided as fiber assemblies or as a component of a fiber assembly.

45. A compound having the formula (II)

or is a salt thereof, wherein R₂and R₃are the same or different and are selected from the group consisting of (CH₂)_m—CH═CH₂with m=0 to 2, R₄denotes a ionic group and/or a group ionizable in an alkaline environment provided that

if R₄═—OH and R₂and R₃both are —CH═CH₂, the two amide groups are not in para-position to each other,

if R₄═—SO₃H, R₂and R₃both are —CH═CH₂and the two amide groups are in ortho-position to each other, the calcium salt is excluded.

46. A process for the production of a compound according to claim 45 comprising reacting a compound having the formula (VIII)

with a compound having the formula (IX)

wherein R₂and R₃are the same or different and are selected from the group consisting of (CH₂)_m—CH═CH₂with m 0 to 2, R₄denotes a ionic group and/or a group ionizable in an alkaline environment.

47. The process of claim 46, further comprising converting the compound obtained to the form of a salt.

48. A process for the production of a compound according to claim 45 comprising reacting in an alkaline solution a compound having the formula (X)

wherein R₅and R₆both are (CH₂)_n—X, n=2 to 4, X=halogen, with a compound having a formula (II),

wherein R₂and R₃both mean (CH₂)_m—CH═CH₂, wherein m=n−2.