CA1085559A - Continuous dyeing of polyester fibers and cellulose fibers - Google Patents

Continuous dyeing of polyester fibers and cellulose fibers

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Publication number
CA1085559A
CA1085559A CA244,331A CA244331A CA1085559A CA 1085559 A CA1085559 A CA 1085559A CA 244331 A CA244331 A CA 244331A CA 1085559 A CA1085559 A CA 1085559A
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CA
Canada
Prior art keywords
dye
fibers
dyes
liquor
oxide
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Expired
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CA244,331A
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French (fr)
Inventor
Peter Freyberg
Dieter Horn
Knut Oppenlaender
Hans Wolf
Dieter Distler
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BASF SE
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BASF SE
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Publication of CA1085559A publication Critical patent/CA1085559A/en
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/60General 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
    • D06P1/607Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6076Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82Textiles which contain different kinds of fibres
    • D06P3/8204Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8223Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8238Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/918Cellulose textile
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/922Polyester fiber

Abstract

ABSTRACT OF THE DISCLOSURE: Polyester fibers and cellulose fibers, and blends of these fibers, are dyed continuously with dis-perse dyes, or dispersed dyes, by continuous application of an aqueous dye liquor which contains, as the essential dyeing assistant, a poloxyalkylated amine, a polyoxyalkylated amine-oxide and/or a quaternized polyoxyalkylated amine which in 1% strength aqueous so-lution has a cloud point of not less than 18°C and which is derived from amines which contain at least 2 nitrogen atoms and at least one group which can be oxyalkylated, followed by drying and fixing.

Description

o.z. 31,133 lOBSSS9 CONTINUOUS DYEING OF POLYESTER FIBERS AND CELLULOSE FIBERS
The present invention relates to a process for the continuous dyeing o~ polyester fibers and cellulose fibers, and blends of these ~ibers, with dlspersed dyes and/or disperse dyes by applying an aqueouB dye llquor, whlch contains a dyelng asslstant, t~ the ~1-bers, drylng and fixlng the dyes.
Contlnuous dyeing o~ polyester flbers wlth dlsperse dyes and o~ cellulose ~ibers wlth vat dyes ls known. In these processes, a dye llquor ls applled, eg. by means of a padder, to the ~abrlc, whlch ls then drled and subsequently sub~ected to ~urther treatment to ~ix the dyes. Durlng the lntermedlate dry~ng of the rabrlc, the dye mlgrates to the sur~ace or wherever evaporatlon ls taklng place, BO that unevenness results. A conventlonal method o~ obtalning level dyelngs ls to add to the dye llquor antlmlgratlon agents, eg. al-glnates, carboxymethylcellulose~ polyacrylamldes and copolymers con-talnlng acryllc acld unlts. The conventlonal antimigration agents are not su~lclently e~fectlve as asslstants, ln continuous dyeing of polyester ~lbers and cellulose ~ibers and thelr blends, to give dye-lngs which con~orm to the highest standards. Texturized polyester ma-terlal ls partlcularly dl~ficult to dye evenly by a continuous pro-cess. Some conventional antimlgration agents distabilize the liquor,even at room temperature, whilst ~thers increase the viscosity and tend to deposit on the applicator rolls.
q~

~8 ~
O.Z. 31,133 It is an ob~ect of the present invention to provide an anti-migration agent, for the process described above, which is more ef-fective than the conventional antimigration agents.
We have found that this ob~ect is achieved, according to the lnvention, by using, as dyeing assistants, polyoxyalkylated amines, amine-oxides of polyoxyalkylated amines and/or quaternized polyoxy-alkylated amines which in 1~ strength aqueous solution have a cloud point Or at least 18C and which are each derived from amines which contain at least two nitrogen atoms and at least one group which can ~e oxyalkylated, and in which the polyoxyalkylene chain contains a) ethylene oxide unit~ and b) propylene oxide, butylene oxide, cyclohexene oxide and/or styrene oxlde units in the molar ratio a:b Or from 10:1 to 0.1:1.
Amines o~ which the molecule contains at least two nitrogen atoms and ~t least one group which can be oxyalkylated are used as startlng materlals ~or the manuracture or the dyeing assistants to bo employed accordlng to the inventlon. An example o~ a group which can be oxyalkylated ls the NH group. The dyelng assistants may also be derlved rrom tertiary amines with at least two nitrogen atoms, provlded the tertiary amine stlll contalns at least one group whlch can be oxyalkylated, eg. a hydroxyl, mercapto, carboxyl and/or carb-oxylic acid amide group. The amines may be aliphatic, aromatic, ar-allphatlc, cycllc or heterocyclic. It is also possible to sub~ect a mixture Or dif~erent amlnes to the oxyalkylation reactlon. Examples o~ suitable amines are ethylenedlamlne, 2-dlmethylaminoethylamlne,
2-dlethylaminoethylamine, 1,2-propylenediamine, 1,3-diaminopropane, ~-methylaminopropylamlne, ~-dimethylaminopropylamine, 3-diethylamino-propylamine, 3-cy¢lohexylaminopropyla~ine, 1 J 4-diaminobutane, 4-di-
3~ ethylaminobutylamine, 1-diethylamino-4-aminopentane, hexamethylene-diamine J 2,5-dimethylhexane-2,5-diamineJ 4J 9-dioxadodecane-1 J 12-di-amine, 6,6-dlmethyl-4J8-dioxaundecane-lJll-diamine, diethylenetri-amine, the amide o~ oleic acid with diethylenetriamine, the amide Or ; -2-1~855~9 o.z. ~1, 13 lauric acid with diethylenetriamine, dlpropylenetriamine, bis-(3-aminopropyl)^methylamine, 1,2-bis-(3-aminopropylamino)-ethane, bis-(6-aminohexyl)-amine, triethylenetetramine, tripropylenetetramine, tetraethylenepentamine, tetrapropylenepentamine, polyimines, eg.
polyethyleneimine, 2-aminomethylcyclopentylamine, 1,1-bis-(4-amino-phenyl)-cyclohexane, 4,4'-diaminodicyclohexylmethane, 3J3'-dimethyl-
4,4'-diaminodicyclohexylmethane, 2,2'-bis-(4-aminocyclohexyl)-pro-pane, 4,4'-diaminodiphenylmethane, N,N'-dimethyl-4,4'-dlaminodiphe-nylmethane, 3,3'-dimethyl-4,4'-diaminodiphenylmethane, tris-(2-amino-ethyl)-amlne, tris-(2-aminopropyl)-amine, aminoethylethanolamine, o-phenylenediamine, p-phenylenediamine, 4-aminopyridine, 2-aminopyrlmi-dine, l-hydroxyethyl-2-dodecylimldazoline, 1-aminoethyl-2-dodecyl-imidazoline, l-hydroxyethyl-2-heptadecenyl-imidazoline, piperazine, 1-(2-hydroxyethyl)-piperazine, 1-(2-aminoethyl)-piperazine, 1,4-bis-(~-aminopropyl)-piperazine and 1-(2-aminopropyl)-piperidine.
The er~lcient dyelng asslstants o~ the present invention are manura¢tured by oxyalkylatlng the relevant amines. As a rule, the pro¢edure rollowed læ to cause the approprlate amine to undergo addi-tlon rea¢tlon, at the group or groups whlch can be oxyalkylated, rin~
wlth the deslred amount o~ one alkylene oxlde, then wlth the lnten-ded amount of the next alkylene oxlde, etc. The sequence ln whlch the oxyalkylation is carrled out ls not crltlcal.
When using, eg., ethylene oxide and propylene oxide as oxyal-kylatlng agents, the ethylene oxide and propylene oxide units may undergo additlon reactlon wlth the amine elther in statistical dis-trlbution or as blocks. A statistical distrib~tion, in the addltion reactlon o~ the alkylene oxide, ls achieved by oxyalkylating the amine wlth a mlxture Or ethylene oxlde and propylene oxlde. In the case Or block copolymeræ, the æequence or addition Or ethylene oxlde and pro-3 pylene oxide may be varied. The molar ratlo ethylene oxide to theother alkylene oxldes may be varied within broad limits and is rrom 0.1:1 to 10:1, and prererably ~rom 0.~:1 to 5:1. Each hydrogen re-placeable by alkylene oxide, e~. the hydrogen o~ an amino group or _~_ 10855~ o.z. 31,133 of an OH group, can be replaced by from 1 to 100 ethylene oxide units or propylene oxide units, preferably by from 2 to 50 alkylene oxide units. Instead of propylene oxide, butylene oxides (1,2-, 2,3-or iso-butylene oxide), styrene oxide and cyclohexene oxide may al-so be employed, individually or together with propylene oxide.
Further very effective antimigration agents for the continuous dyeing of polyester fibers and cellulose fibers are the am~ne oxides which can be prepared from the polyoxyalkylated amines described above. These amine oxides are obtained by reacting the polyoxyal-kylated amines with hydrogen peroxide. Depending on the degree of conversion, partially or completely oxidlzed polyoxyalkylated amines are obtalned, and these may be emp~oyed by themselves or mixed with the oxyalkylated amines.
Quaternized polyoxyalkylated amines are also excellent anti-migration agents. They are obtained, eg., ~rom polyo~yalkylated amines by reaction with conventlonal quaternizing agents, eg. di- -methyl sul~ate. It is also possible to employ completely or partlal-ly quaternized products, or mlxtures of quaternized polyoxyalkylated amlnos and (non-quaternl~ed) polyoxyalkylated amines.
The dyeing assistants to be employed accordlng to the invention are also characterlzed by thelr cloud point, which in 1% strength aqueous solution ls at least 18C. It ls determined in accordance wlth DIN 5~,917, Method 6.1 (August 197~). The cloud polnt is an im-po~tant datum for characterlzing the polyoxyalkylated amines, because the appropriate dyeing assistants cannot be adequately defined in term~ of the degree o~ oxyalkylation, the ratio Or the various al-kylene oxides and other data such as hydroxyl numbers, viscositles and the like.
The dyelng assistants to be employed accordlng to the ln~entlon arç added to the aqueous liquor in amounts of rrom 0.5 to 70 g/l, preferably from 2 to 50 g/l. They cause the dyes to flocculate from the liquors at elevated temperatures, eg. at from 30 to 100C. An optlmum flocculation temperature for the particular dyeing process 1~85559 o,z. 31,133 may be obtained by selecting suitable polyoxyalkylated amines, poly-oxyalkylated amine oxides or quaternized polyoxyalkylated amines.
It ls known that padding should be carried out with dye liquors which are stable at the conventional padding temperatures (below 35C).
Flocculation is only allowed to occur at a higher temperature. In continuous dyeing, this temperature is reached, and exceeded, during the intermediate drying operation following padding with the liquor.
The temperature at which flocculation occurs can be controlled both by the selection Or sultable polyoxyalkylated amines, the corres-pondlng amlne oxldes Or polyoxyalkylated amines and the correspond-ing quaternlzed polyoxyalkylated products, and by varying the amount of these compounds and the pH of the liquor. It ls particularly ad-vantageous lf the pH of the paddlng llquor ls less than 7. Prererab-ly, the pH ls ad~usted to from ~ to 6.5, although lt ls possible to carry out the process according to the lnventlon at a pH above 7.
The antlmlgration agents accordlng to the lnventlon may be em-ployed together with conventional dyelng asslstants such as levelling agents and dlspersing agents, wlth conventlonal antlmlgration agents, wlth non-lonlc, anlonlc and catlonlc emulslflers, wlth natural and synthetlc protective colloids and with natural and synthetlc thlcke-ners, eg. those conventlonally used in textile printlng.
In the present cantext, polyester flbers are to be understood as linear polyester fibers, eg. polyethylene terephthalate fibers.
Cellulose ribers are, eg.,flbers Or natural, esterlfled or regene-rated cellulose, such as cotton, rayon staple, vlscose, cuprammonium rayon, a¢etate and triacetate. The polyester flbers are dyed wlth disperse dyes, whllst the cellulose rlbers are dyed wlth dlspersed dyes, above all vat dyes, but also with naphthol dyesJ sulfur dyes and some dlrect dyes. The method ls not li~lted to a certaln state ~0 of the ribers durlng processing, and can instead be employed, in prlnclple, rOr dyeln~ tow, card,yarn, woven fabric and knitted fa-brlc. The ~ibers may be texturlzed or non-texturized.
The process is carried out contlnuously by first paddlng, eg.,
-5-o.z. 31,133 a polyester ~abric with the aqueous dye liquor on a padder, then sub~ecting the fabric to an intermediate drying operation and there-a~ter heating it to a higher temperature to fix the dye. In continu-ous dyeing of cellulose fibers, fixlng means, in relation to the in-ventlon, developing the vat dye, ie. reduction, soaping and oxida-tion. In continuous dyeing Or fabrics consisting of blends of poly-ester fibers and cellulose fibers, the fabric is padded with a dye liquor which contains at least one disperse dye and at least one vat dye or other dyes suitable for dyeing cellulose fibers. The liquor may also be applied to the fabric by drawing the latter through the liquor and then bringing it to a certain liquor pick-up by, eg., squeezing off. Preferably, the aqueous dye liquor containing the assistants according to the invention is applied at room tempera-ture, but the process can also be carried out at up to 40C, or even above. The woven or knitted fabric treated with the liquor is then heated at ~rom 80 to 150C, preferably rrom 100 to 140C, to dry lt. To ~lx the di8perse dyes to the ribers, the rabrlc ls heated at rrOm 150 to 230C, preferably rrOm 160 to 220C. The drying, and rlxing of the disporse dyos, can also be carrled out in a slngle step, eg. by lmmedlately treatlng the rabric at 175C, uslng live steam as the heating medium. When the disperse dye has been rlxed, the vat dye ls developed. The pH can be brought to the most advan-tageous range ror the dyelng prooess by using acids or salts con-, ventionally employed ln dyeing, eg. weak acids such as acetic acld, j formlc acld and oxalic acid, or salts such as sodium acetate.
I The dyeing assistants to be employed accordin~ to the invention j prove to be very efrectlve even wlth texturlzed polyester knltted ~abrics, have no adverse efrect on the stabllity Or the liquor and hardly afrect the viscosity of the latter. Because Or their own good wetting action, the use o~ wetting agents proves superfluous with a~umber of the compounds according to the invention. Though addition products of ethylene oxide and/or propylene oxide with alcohols, eg. glycols, have cloud points in the range from 30 to 100C, they
-6-1085559 o. z. 31, 13~
nevertheless are unsuitable ~or uc;e as antimigration agents in con-tinuous processes for dyeing polyester fibers and cellulose fibers.
Experiments have shown that the oxyalkylated monoamines de-scrlbed in French Patent 1,436,9ll (eg. reaction products o~ l mole o~ oleylamine and 25 moles of ethylene oxide or of l mole of stearyl-amlne and 25 moles of ethylene oxide) cannot be employed success-~ully as antimigration agents ~or the process described above.
The invention is explained in more detail in the Examples which follow, in which parts and percentages are by weightO The cloud point was determined by the method of DIN 53,9l7.
MANUFACTURE OF THE POLYOXYALKYLATED AMINES
The oxyalkylated amlnes are manu~actured by conventional methods to which no claim is made herein.
A: Thermal Reaction Sta~e I
1 mole o~ a polyamine and 5% by welght of water, based on the polyamlne, are lntrodu¢ed into an autoclave and reacted, at from 90 to 100C, wlth one mole o~ propylene oxlde or ethylene oxlde (the epoxldo belng added ln portlons) per alkyleneamlne unit or NH group, 80 that all reaotlve NH groups are converted to alkanolamlne groups.
It ls advlsable to uæe a 10% excess of epoxlde. me reactlon tlme, at 6 atmospheres pressure, ls about 2 hours at 90C for ethylene oxlde, and about 3 hours at 100C ~or propylene oxlde. The reactlon product ls then drled at ~rom 90 to 100C and 15 mm Hg.
Bs Catalytlc Stage II
l mole o~ the product manuractured accordlng to A and 1% by welght (based on A) o~ 100% strength KOH are lntroduced into a stlrred autoclave and are reacted, in acaordance with the deslred degree Or oxyalkylation, wlth the approprlate amount o~ propylene oxlde added ln portions at from 130 to 135C and/or wlth the re-quislte amount o~ ethylene oxlde at from 120 to 125C. The sequence ls optlonal and it is also possible to use a gaseous mixture o~
ethylene oxlde and propylene oxide, but in that case random co-polymers are obtained. The reaction time is ~rom 6 to 8 hours at 8 10855~ o.z. 31,133atmospheres pressure and the vemperature glven above for each al-kylene oxide. For a gaseous mixture of ethylene ox~de and propylene oxide the temperature is from 125 to 1~0C. To complete the reac-tlon, the mixture ls allowed to post-react for ~ hours under pres-sure, The polyoxyalkylated amines listed in Table 1 were manufactured ~n accordance with the process described above. The amine oxides of polyoxyalkylated amines and quaternized polyoxyalkylated amines, also shown in Table 1, were manufactured respectively by oxidation or quaternization o~ the corresponding polyoxyalkylated amines.
The following abbreviations were used:
E0 for ethylene oxlde, and P0 for propylene oxide.
The ~rd column of Table 1 shows the number of moles of ethylene oxlde (E0) and propylene oxide (P0) which have undergone additlon reaatlon per mole o~ amlne. The ~lrst-mentioned oxlde was rlrst sub-Jected to the addltlon reactlon, and only afterward was the other oxide block polymerlzed onto the produ¢t. In the case o~ the poly-lmlnes, the moles of E0 and P0 are per ethylenelmine unlt.
In the case of dyelng asslstant No. 9, E0 and P0 were not grarted onto the amlne successlvely, but as a gaseous mlxture, and thls produ¢es a random copolymer of the two monomers, ln contrast to the block copolymers (EO)x-(PO)y.
The penultlmate column shows the cloud polnt, ln degrees centl-grade, Or the particular dyelng assistant, measured ln 1% strength aqueous solutlon.
The last column shows the molar ratlo of ethylene oxlde (E0) to p~opylene oxlde (P0).

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/~ J N C~J ~U 1 Use of the compounds according to the invention The conventional test methods used ror testlng the antlmigra-tion effect (H. Lehmann and F. Somm, Textil-Praxis 197~, page 52) wlll first be described briefly:
Plate test at 100C
A plece of fabric (woven or knitted) of slze about 12 cm x 12 cm ls padded and then lmmediately placed on a glass plate ~about 12 cm x 12 cm) and covered ln the center only with a 1 cm thick clrcular glass plate (diameter about 7 cm). The assembly is then immediately placed in a drying oven at 100C. After drying, the depth of color of the covered and uncovered areas are compared.
In this test, very great differences in depth of color between the covered and uncovered areas of the strip of woven or knitted -fabric are found (a substantially lighter, circular patch being found in the covered area) even lf conventional industrially used anti-mlgration agents, such as alginates, polyacrylamides, polycarboxylic aclds (lnoludlng acryllc acld copolymers) or carboxymethylcelluloses are employed. Even lf the sald assistants are employed ln very high concentrations, the test ln general only shows moderate inhibltion o~ mlgratlon.
Foldlng test at 100 C( cf. M.Brauer, Melliand Textllber.41(1960)1102) The strip of woven or knitted fabric of slze about 12 x 12 cm, which has been padded with the dye liquor, is folded once, closed alr-tlght at the 3 open ends with broad metal cllps and hung in a drylng oven at 100C. As a result of the strip having been folded, drying is only posslble on the outer face of the fabric. The dye inside the fabric strlp will attempt to mlgrate through the fabrlc.
Accordingly, dlstinct differences in depth of color are found be-tween the inner ~ace and outer face.

L~ ' . . .~, . . .

~parison of inside and olltside of a tex~ b~e~
A strip of polyester knitted fabric (Diolen loft ~ tted fabric, Trevira 2,000 knitted fabric etc.) of size about 40 cm x 12 cm is padded, dried for 120 seconds on a pin stenter at 110C and then ther-mosoled for 90 seconds at 165C. A~ter reductive cleanlng for 30 ml-nutes at 70C ln a liquor comprlsing 4 g/l of sodium hydroxide so-lutlon Or 38Bé streng~ 2 g/l of concentrated hydrosulflte powder and 1 g/l Or oleylamlne polyglycol ether, uslng a liquor ratio of 40:1, the evenness and depth of color, the dye migration at the edges and perforatlon points of the pins, and the dirference in depth of color between the inside and the outside of the texturized polyester knitted fabric ls assessed; an assessment Or the latter dlfference is very easlly possible by stretching the knitted fabric.
The ob~ectlve ls that with the fabric stretched, the obviousness o~
llghter-colored stripes should be minimlzed.

A texturlzed polyester materlal (Diolen loft knitted fabric) is padded at room temperature with a liquor, which contalns, per llter o~ water, 25 g of the yellow dlsperse dye C.I. No. 47,023, in lts commercial rorm and conslstency, and lO g of the dyelng asslstant No. 2, and which has been brought to pH 4.5 with acetic acld; the llquor plck-up is about 80% (based on dry goods weight).
The plate test is carried out with a part of the padded fabric, at 100C. The test shows only very sllght dye migration, ln con-trast to experiments with conventional antimigration agents, eg.
a medium-viscoslty sodium alginate or a copolymer of acrylic acid, having a Ford cup 8 flow time of 100 seconds. With a compound of 1 mole o~ oleylamlne and 25 moles of ethylene oxide, agaln vlrtual-ly no migration-lnhi~itlng effect is found.

* Trademark for polyethylene terephthalate (polyester fiber) made by Enka-Glanzstoff AG.

** Trademark.

iR

~085559 Another part of the padded fabric is intermediately dried on a pin stenter at 110 C for 120 seconds, then subjected to a thermosol treatment at 165C for 90 seconds and cleaned reduc-tively in the conventional manner. A level deep dyeing with good general fastness properties is obtained. On pulling the knitted fabric apart, lighter-colored stripes do not become visible.
Extremely little dye migration is found at the points of per-foration of the pins. The antimigration effect of the assistant used by far surpasses that of conventional migration inhibitors.

Similar results are obtained if Diolen loft knitted fabric is dyed with the dyes and assistants shown in Table II, under the conditions also shown in the Table:

* Trademark for polyethylene terephthalate (polyester fiber) made by Enka-Glanzstoff AG.

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~XAMPL~ 2 A texturized polyester material (Trevira 2000 ~nitted rabrlc) ~-ls padded at room temperature with a llquor which contalns, per llter Or water, 50 g o~ the red dlsperse dye from German Patent 1,271,284~
Example 4, column 9, 1st line, in its commercial ror~ and consisten-cy, and 13 g o~ the dyeing assistant No. 4, and which has been brought to pH 4.5 with acetic acid; the rabric is squeezed off to a liquor pick-up of about 80~.
The plate test at 100C is carried out with a part of the strip of knitted fabrlc, and the folding test at 100C with another part of the rabric. Both test methods show only negligible dye migration, which in the plate test manlfests itself in the circular patch o~
the covered area being barely discernible and in the folding test in that there are virtually no differences in depth Or color between the inside and outside. If the conventional antimigration agents, eg.
a carboxymethylcellulose which in 30% strength aqueous solution has a Ford cup 8 flow tlme o~ 58 seconds, or an acrylic acid copolymer which has a Ford cup 8 ~low tlme of 100 seconds, are used, the suc-¢ess, as measured by the above test methods, ln suppressing dye ml-gratlon ls only very moderate.
Dye mlgration can also not be prevented by using a compound of 1 mole of oleylamine and 25 moles of ethylene oxide or a compound o~
1 mole o~ dodecylamine, 5 moles of propylene oxlde and cO moles of ethylene oxlde (accordlng to French Patent 1,436,911).
Slmllar results are obtalned 1~ Trevlra 2,000 knltted fabric ls dyed wlth the dyes and asslstants shown ln Table III, under the condltions also shown in the Table.

** Trademark i 1~

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The same dye liquors as in Exampl36 2 are used ~or padding non-texturized polyester woven fabric, but the liquor pick-up is about 60%, based on the fabric. With this fabric, again, both the plate test and the folding test shows at most an extremely slight dye mi-gration, in the case of all the assistants employed.

A blended woven fabric of polyester ribers and cotton fibers mixed in the proportions o~ 67:~3 is padded at room temperature with a liquor which contains, per llter of water, 25 g of the vat dye C.I. No, 67,ooo, 10 g of the pink disperse dye from German Patent 1,209,680, Example 2/1, 4 g of the red disperse dye from German Pa-tent 1,259,285, Example 2 and 2 g of the red dlsperse dye from Ger-man Patent 1,271,284, Example 4, column 9, 1st line, in their com-mercial ~orm and consistency, and 10 g of the dyeing asslstant No.10 (~rom Table I), and which has been brought to pH 4.5 with acetic acid; the llquor pick-up is about 60% (based on dry goods).
The plate test at 100C and/or the roldlng test at 100C are osrried out ~lth a part o~ the padded strip of rabric. The other part Or the blended ~abrlo is drled ~or 60 se¢onds at 110C, then treated with hot air at 210C ~or 60 seconds, and therearter deve-2R loped, ln the laboratory, ln a continuously rotatin~ apparatus work-lng on the Launder-0-Meter prlnclple, ~or 30 mlnutes at 60C using a ¢hemical liquor (liquor ratio 1:5) which contains, per liter Or wa~er, 20 ¢¢s of sodium hydroxide solution o~ 38Bé strength, 8 g o~ concentrated hydrosul~ite powder and 3 g o~ a dlspersing agent ba~ed on the sodlum salt Or a ~-naphthalenesul~onic acid/rormalde-hyde oondensat$on product.
Arter soaping at the boll ln the conventional manner ~or 20 mlnutes, the polyester and cotton constituents o~ the fabric are dyed red ln approximately matchlng shades. -In both the plate test and the ~olding test virtually no dye migration is foun~. The effect is clearly superior to that of con-1~85559 o. z. 31, 1~3 ventional antlmlgration agents, such as an acrylic acld copolymer havlng a Ford cup 8 flow time of 100 seconds.
The flnlshed deyings are deep and le~el; their general fastness properties are ~ood.
Simllar results are obtalned if the dye mixtures shown in Table IV, in thelr commercial form and consistency, and the assis-tants also shown in Table IV are employed:

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-24_ 108~ O.Z. 31,133 A cotton woven fabric is padded at room temperature with a liquor whlch contains, per liter of water, 40 g o~ the red vat dye C.I. 67,ooo in its commercial form and consistency and 8 g of dyeing assistant No. 3, and which has been brought to pH 4.5 with acetic acld; the fabric is squeezed off to a liquor pick-up of 60% based on dry goods weight.
After padding, a part of the fabric is sub~ected to the plate test at 100C. The other piece of fabric is intermediately dried ~or 60 seconds at 110C and then developed in the laboratory in a con-tinuously rotatlng apparatus, worklng on the Launder-0-Meter prin-clple at 60C for 4~ mlnutes, using a chemlcal llquor (liquor ratio - 4:1) whlch contalns, per liter of water, 18 ccs of sodlum hydroxide solution Or 38B~ strength and 5 g of concentrated hydrosulfite pow-der, and ls then soaped at the boll. A smooth deep red dyelng of good eVenlle88 i8 obtalned. The plate test showæ vlrtually no dye mlgra-tion, ln contra~t to the reæult obtained with liquors containing the oonventlonal antlmlgration agents, eg, a medlum-vlscoælty sodlum alglnate or an a¢rylic a¢id copolymer havlng a Ford cup 8 flow tlme o~ 100 ~econds.
Similar results are obtained lf the dyeæ and aæælstants shown ln Table V are employed:

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Claims (7)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. A process for the continuous dyeing of polyes-ter fibers, cellulose fibers or blends of these fibers, which process comprises:
continuously applying to said fibers an aqueous dye liquor which contains I. a disperse dye for polyester fibers, and for cellulose fibers a dye selected from the group consisting of vat dyes, naphthol dyes, sulfur dyes and direct dyes, and II. from 0.5 to 70 g/l of said aqueous dye liquor of an antimigration agent selected from the group consisting of polyoxyalkylated amines, amine oxides of polyoxyalkylated amines and quaternized polyoxyalkylated amines which in 1%
strength aqueous solution have a cloud point of at least 18° C and which are each derived from amines which contain at least 2 nitrogen atoms and at least one group which can be oxyalkylated and in which the polyoxyalkylene chain contains a. ethylene oxide units and b. a second component selected from the group consisting of propylene oxide, butylene oxide, cyclohexene oxide and styrene oxide units in the molar ratio a:b of from 10:1 to 0.1:1, said continuous application being carried out at a temperature below that at which the dye or dyes flocculate from the liquor;

drying the fibers while heating at an elevated temper-ature sufficient to flocculate the dye or dyes from the liquor; and fixing the dye or dyes to said fibers.
2. A process as claimed in claim 1, in which from 2 to 50 g/l of aqueous dye liquor of the antimigration agent are employed.
3. A process as claimed in claim 1, in which the polyoxyalkylated amine, amine oxide or quaternized amine is derived from 1,6-hexamethylenediamine, ethylenediamine, triethylenetetramine, orthophenylenediamine or polyethyleneimine.
4. A process as claimed in claim 3, in which the antimigration agent employed is a polyethyleneimine which is first oxyalkylated with ethylene oxide and then with propylene oxide, and is finally quaternized.
5. A process as claimed in claim 1, in which the pH of the dye liquor is from 3 to 6.5.
6. A process as claimed in claim 1, in which the continuous dye application is carried out at about room temperature up to about 40° C. and the dye flocculation is carried out at a drying temperature of from about 80° to 150° C.
7. A process as claimed in claim 6, in which the pH
of the dye liquor is from 3 to 6.5.
CA244,331A 1975-02-01 1976-01-23 Continuous dyeing of polyester fibers and cellulose fibers Expired CA1085559A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP2504282.4 1975-02-01
DE2504282A DE2504282C3 (en) 1975-02-01 1975-02-01 Process for the continuous dyeing of polyester and cellulose fibers

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CA (1) CA1085559A (en)
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GB1591034A (en) * 1977-01-14 1981-06-10 Ici Ltd Process for the continuous colouration of aromatic polyester or cellulose triacetate textile materials and of unions of aromatic polyester with cellulose
CH634708B (en) * 1978-09-29 1900-01-01 Ciba Geigy Ag PROCESS FOR PUMPING OF TEXTILE MATERIALS COMPOSING WHOLE OR PARTLY CELLULOSE FIBERS
US4659802A (en) * 1982-12-23 1987-04-21 The Procter & Gamble Company Cationic compounds having clay soil removal/anti-redeposition properties useful in detergent compositions
CH671052A5 (en) * 1985-01-30 1989-07-31 Sandoz Ag
US5238464A (en) * 1986-06-05 1993-08-24 Burlington Industries, Inc. Process for making flame-resistant cellulosic fabrics
US4902300A (en) * 1986-06-05 1990-02-20 Burlington Industries, Inc. Simultaneously dyed and flame-retarded fabric blends
US5364462A (en) * 1991-08-14 1994-11-15 Graphic Utilities, Incorporated Waterfast inks
US6794355B1 (en) * 1998-11-02 2004-09-21 The Procter & Gamble Company Fabric care composition having reduced fabric abrasion
EP1716285A1 (en) * 2004-02-19 2006-11-02 Huntsman Advanced Materials (Switzerland) GmbH Method of increasing depth of shade
WO2006108856A2 (en) * 2005-04-15 2006-10-19 Basf Aktiengesellschaft Amphiphilic water-soluble alkoxylated polyalkylenimines with an internal polyethylene oxide block and an external polypropylene oxide block
AU2008324178A1 (en) * 2007-11-09 2009-05-14 Basf Se Amphiphilic water-soluble alkoxylated polyalkyleneimines having an inner polyethylene oxide block and an outer polypropylene oxide block
MX307780B (en) 2007-11-09 2013-03-08 Procter & Gamble Cleaning compositions comprising a multi-polymer system comprising at least one alkoxylated grease cleaning polymer.
ES2479392T3 (en) * 2007-11-09 2014-07-24 The Procter & Gamble Company Cleaning compositions with amphiphilic water-soluble polyalkyleneimines having an internal block of poly (ethylene oxide) and an external block of polypropylene oxide
US9068147B2 (en) 2012-05-11 2015-06-30 Basf Se Quaternized polyethylenimines with a high quaternization degree

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US3223471A (en) * 1965-12-14 Process fgr dyeing textile materials
US2674619A (en) * 1953-10-19 1954-04-06 Wyandotte Chemicals Corp Polyoxyalkylene compounds
GB976529A (en) * 1961-06-09 1964-11-25 Asahi Denka Kogyo Kk An improved method for dyeing nitrogenous fibres and textiles
FR1378695A (en) * 1963-01-05 1964-11-13 Sandoz Sa Process for obtaining well-even dyes on textiles with special additives
US3503698A (en) * 1963-02-08 1970-03-31 Geigy Ag J R Pad-dyeing and printing textile fibers
DE1619542B1 (en) * 1967-08-08 1971-02-04 Bayer Ag Process for dyeing nitrogen-containing fiber materials
ES367288A1 (en) * 1968-05-17 1971-04-01 Sandoz Ag Levelling agents for and process for colouring a fibrous natural polyamide with reactive dyes
US3822113A (en) * 1970-07-09 1974-07-02 Ciba Geigy Ag Acid dye and ethylene oxide condensate of an n-long chain alkyl dipropylene triamine
BE789814A (en) * 1971-10-07 1973-04-06 Basf Ag PROCESS FOR PREVENTING MIGRATION INTO DYING OR PRINTING OF FIBROUS MATERIALS USING PIGMENTARY DYES
DE2348518B2 (en) * 1973-09-27 1978-06-29 Basf Ag, 6700 Ludwigshafen Powdery, highly concentrated and dispersion-stable dye preparations and processes for their production

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FR2299450A1 (en) 1976-08-27
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IT1053421B (en) 1981-08-31
DE2504282A1 (en) 1976-08-05
DE2504282B2 (en) 1979-07-26
BR7600591A (en) 1976-08-31
GB1526332A (en) 1978-09-27
FR2299450B1 (en) 1979-05-04

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