US3506990A - Process for dyeing drawn filaments of aromatic polyamides with basic dye-stuffs in the presence of an organic dye carrier - Google Patents

Process for dyeing drawn filaments of aromatic polyamides with basic dye-stuffs in the presence of an organic dye carrier Download PDF

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Publication number
US3506990A
US3506990A US602144A US3506990DA US3506990A US 3506990 A US3506990 A US 3506990A US 602144 A US602144 A US 602144A US 3506990D A US3506990D A US 3506990DA US 3506990 A US3506990 A US 3506990A
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Prior art keywords
dye
dyeing
aromatic
aromatic polyamides
stuffs
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US602144A
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English (en)
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Arturo Jorge Richardson
Robert E Walck Jr
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EIDP Inc
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EI Du Pont de Nemours and Co
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/242—Polyamides; Polyurethanes using basic dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino-carboxylic acids or of polyamines and polycarboxylic acids
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
    • D01F6/605—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides from aromatic polyamides
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber
    • Y10S8/925—Aromatic polyamide

Definitions

  • Aromatic polyamides have been found well-suited for a broad range of utility where exposure to high temperatures is involved. Such polymers and shaped structures derived therefrom are shown, for example, in the Kwolek et al. US. Patent 3,063,966, which teaches process for their manufacture. Consistent with their excellent utility at high temperature there is a strong tendency for members of this class to crystallize or, by some mechanism not yet defined, to develop a highly consolidated, dense structure.
  • the closely packed molecular configuration of shaped structures comprising aromatic polyamides known Description of the prior art While the various manipulative steps are individually known in the art, their combination in order to obtain the highly desirable result of the present invention is not known to be suggested by the art.
  • a process for dyeing textiles formed from synthetic meta or para oriented, wholly aromatic polyamides containing from 2 to about 15 molar percentage of an aromatic dye associable copolymeric unit which comprises heating the drawn filaments of the said textile while the said filaments are free to relax to a temperature between about 150 to 280 C. for a period between about l'minute (at the upper temperature) and about 45 minutes (at the lower temperature) and thereafter dyeing the said textile in a dye-bath containing (1) a dye with which the said 00- polymeric unit is associable and (2) a dye assistant.
  • a dye assistant is meant any organic substance which is substantially inert to the dyebath under the conditions employed and capable of being absorbed by the shaped aromatic polyamide structure to the indicated extent under the conditions of dyeing specified.
  • the substance may be a pure compound or a mixture of compounds.
  • K/S refers to the ratio of absorbed light to scattered light as measured in the usual manner, using a photometer for measuring incident and reflected light.
  • K/S values are related to apparent depth of dyeing attained; percent dye on fiber is no more complex than implied for the expression, being merely an indication of the quantity of dye in or on the fiber which is not removed by a simple scour.
  • Dye yield is calculated as the ratio of K/S value to the percent dye-on-fiber and is an indication of the effectiveness of the dye taken up by the fiber in producing visible coloration. Dye yield and percent-exhaust are closely allied to economy of the dyeing operation and therefore of great practical importance.
  • Example 1 A series of aromatic copolyamides is prepared by a process as taught in the Kwolek et al. US. Patent 3,063,-'
  • the tows. are then cut to about a 2-inch staple length, and hand-carded pads are prepared from each lot for dyeing.
  • the pads are dyed individually under a pressure of 20 p.s.i.g. in 40 times their weight of a dye-bathof the following parts by weight composition:
  • a total of 13 dyeings is made, six without a dye assistant
  • the yarn is knitted on a stoll-knitting machine and the and seven with an equal weight mixture of dimethyl ter- 15 resulting knitted fabric is relaxed at 240 C. for 30 minephthalate and benzanilide as a dye assistant.
  • the dyeing utes under conditions of no restraint.
  • the relaxed fabric periods and results obtained are summarized in Table II. is dyed with an acid dye under a pressure of 15 p.s.i.g.
  • the a items each were dyed with the dye assistant, the for two hours, the dye bath having the following compob items contained no dye assistant. sition and the ratio of bath to tubing being 50/ 1.
  • dye pickup Example 3 by the Polymer P thls examPle 18 5 as to This example illustrates suitability of the process of pletely unattractive commerclally even Wlth the highest this invention for dyeing of ordqed copolymers such as level of modification by NaSMPD. It will be apparent disclosed i US. 3,232,910.
  • the solution is solution is neutralized by the addition of 69 parts dry dry spun in a manner equivalent to that of Example 1 lime slurried in an additional 117 parts of DMAc.
  • the and the filaments so obtained are extraction-drawn to solution is vacuum-deaerated with elimination of 180 450% of their spun length in hot water.
  • the filaments are parts of DMAc containing a small amount of water, after heated at 260 C. for 20-30 minutes under conditions which it contains'19.5% of a copolymer of MPD-I/MPD- 70 of no restraint.
  • the former yield polymers having the repeating structure 0 H H NAr N( JAr-a while the latter yields polymers having the repeating structure H i Y R -N-Ano N-And' wherein Ar and Ar represent divalent aromatic residues and may be the same or different.
  • Ar and Ar represent divalent aromatic residues and may be the same or different.
  • Also useful in the practice of this invention are the various combinations, ordered or random, of both types of structures. Ordered copolymers are illustrated in the Preston US. Patent 3,232,910.
  • the minor amide constituents are exemplified by those derived from and the like.
  • blends of polyamides where a minor component of the lend is a polyamide containing a dye associable substituent may be used in the process of the present invention, the minor component constituting from about 2 to about 15 weight percentage of the blend.
  • a typical blend for such a purpose can be formed by mixing 2400 parts of an 18.4% MPD-I polymer solution in DMAc/calcium chloride with 272 parts of a 20% solution of a CaSMPD-I polymer in DMAc. The solution can then be dry spun toafilament.
  • the process of this invention is generally applicable to aromatic polyamide structures. It is especially useful for aromatic polyamides which strongly tend to consolidate to highly dense structures at high temperature; these are characterized as those having a well-ordered molecular structure and/ or unsubstituted amide hydrogens. When highly consolidated by heat, structures of polyamides are not penetrated by dyes available in the trade to a useful extent.
  • the utility of this invention in process for dyeing of such structures is subject only to three limitations: (1) the polymer must carry functional groups which tend to yield stable associations with a dyestuff, (2) high temperature exposure in the process for preparation of the shaped structure must be encountered only when the structure is free to relax, and not exceed 280 C., and (3) a dye assistant is required which is, under the conditions of dyeing, absorbed by the structure to the extent of at least 5%.
  • Typical useful dye assistants are B-napthol; diphenyl sulfone; salicyl aldehyde; salicylic acid, salicylanilide; dimethyl isophthalate; benzyl alcohol; pelargonic acid; benzoic acid; o-phenyl phenol; dimethyl terephthalate; benzanilide; isopropylidene 4,4'-di-phenol; hexamethyl phosphorarnide; dimethyl acetamide; or other members of the homologous series, wherein the acyl residue comprises 1-10 carbon atoms, formic acid and the lower homologues thereof, methylene chloride, dimethyl cyanamide, tetramethylene sulfone, 2,4-dimethyltetramethylene sulfone, ethylene diamine, triethylene tetramine, pyrrolidine, pyridine, piperidine, cyclohexylamine, and the like, it being required only that the compound or mixture employed as a dye
  • the fibers of the present invention In processing the fibers of the present invention it is important that they not be exposed to temperatures as high as about 200 C. while taut prior to high-temperature relaxation. Heating of the drawn filaments while relaxed for as little as 1 min. at the upper range of tempeature treatment is usually adequate for purposes of the present invention. Longer periods are required if lower temperatures are used. Generally a draw of about 4 /2 times extruded length is used to develop good textile properties in the yarn, and relaxed heating is provided until an effective draw of about 3 /2 times is reached due to shrinkage in the heat treatment step.
  • the heat relaxation step can be performed upon the yarn, staple or fabric. It is often advantageous to steam the drawn yarn (or staple or fabric) prior to heat relaxation in order to reduce residual shrinkage in boiling water in the final structure. Such steaming does not affect dyeability.
  • the invention is not limited to the exemplified anionicactive or cationic-active copolymeric constituents. It will be apparent to one skilled in this art that the only criterion of such a constituent is that it comprise an aromatic-ring substituent of the desired functionality in combination with bifunctional, polyamide-forming capability. Such a compound may comprise one or more aromatic rings and where two or more are involved may comprise additionally alkylene, cycloalkylene or heterocyclic groups therebetween with the limitation that the chain-extending, amide-precursive groups must, in each case, be directly attached to carbon of aromatic rings.
  • bifunctional radicals which may bridge between aromatic moieties of the starting materials are x0; sulfide, disulfide, methylene, propylene, dimethyl methylene, carbonyl, sulfo, hexafluoroisopropylidene and the like. It is within the scope of this invention to employ an amino carbonyl halide bearing a functional group capable of stable association with a dyestuif, as exemplified by 3- amino chlorobenzoyl 5-sulfonic acid.
  • organic dye carrier is an equal weight mixture of dimethyl terephthalate and benzilide.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Coloring (AREA)
US602144A 1966-12-16 1966-12-16 Process for dyeing drawn filaments of aromatic polyamides with basic dye-stuffs in the presence of an organic dye carrier Expired - Lifetime US3506990A (en)

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US60214466A 1966-12-16 1966-12-16

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BE (1) BE708043A (enrdf_load_html_response)
FR (1) FR1548029A (enrdf_load_html_response)
LU (1) LU55113A1 (enrdf_load_html_response)
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Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3630662A (en) * 1966-09-19 1971-12-28 Celanese Corp Process of dyeing shaped condensation polymer material in heated two-phase dye liquid
US3652199A (en) * 1969-08-28 1972-03-28 Du Pont Process for drying polyamide fibers catonic dyes and zinc thiocyanate
US3673160A (en) * 1970-02-12 1972-06-27 Rhodiaceta Process for producing brilliant sulfonated polyamide-imide fibers and such fibers so produced
US3779705A (en) * 1970-08-14 1973-12-18 Teijin Ltd Process for dyeing fibers or fabrics of aromatic polyamides
US3836327A (en) * 1971-01-08 1974-09-17 Sybron Corp Aromatic alcohol-aromatic aldehyde carrier dyeing of aromatic polyamides
US3873338A (en) * 1973-02-28 1975-03-25 Us Air Force Thermal stabilization of polyamide fibers
US3900286A (en) * 1971-11-19 1975-08-19 Ciba Geigy Ag Dyestuff preparations and processes for the dyeing of synthetic organic material
US3953167A (en) * 1973-07-24 1976-04-27 Teijin Ltd. Process for dyeing fibers or fabrics of aromatic polyamides
US4059403A (en) * 1974-08-10 1977-11-22 Bayer Aktiengesellschaft Process for dyeing wet-spun aromatic polyamides in gel form
US4078889A (en) * 1974-08-10 1978-03-14 Bayer Aktiengesellschaft Process for dyeing dry-spun aromatic polyamides
US4108936A (en) * 1974-08-10 1978-08-22 Bayer Aktiengesellschaft Process for dyeing wet-spun aromatic polyamides in gel form
US4741740A (en) * 1986-05-14 1988-05-03 Burlington Industries, Inc. Flame-resistant properties of aramid fibers
US4814222A (en) * 1986-05-14 1989-03-21 Burlington Industries, Inc. Aramid fibers with improved flame resistance
US4824916A (en) * 1985-03-15 1989-04-25 The Dow Chemical Company Water-insoluble, crosslinked, sulfonated aromatic polyamide
US4895660A (en) * 1986-07-14 1990-01-23 The Dow Chemical Company Water-soluble aromatic polyamides and polyureas
US5298201A (en) * 1990-12-21 1994-03-29 Milliken Research Corporation Method for improving dyeability of fiber and associated fabric utilizing radiation
US5404625A (en) * 1990-10-12 1995-04-11 Milliken Research Corporation Method and apparatus for modifying fibers and fabric by impaction with particles
US5437690A (en) * 1994-05-25 1995-08-01 Springs Industries, Inc. Method for dyeing fibrous materials and dye assistant relating to the same
US5852087A (en) * 1996-02-13 1998-12-22 Teijin Limited Easily dyeable meta-linkage-containing aromatic polyamide fibers
EP0806198A3 (de) * 1996-05-09 2001-07-25 Wella Aktiengesellschaft Färbemittel
EP1902808A1 (en) 2006-09-21 2008-03-26 Louis Wardlaw Enclosure for use during operations for applying heat to at least one conduit member comprising gloved armature means and viewing section ; Method of enclosing a conduit upon which a heating process is to be conducted using such enclosure
US20080152888A1 (en) * 2006-09-08 2008-06-26 Southern Mills, Inc. Methods and Systems for Providing Dyed, Stretchable Flame Resistant Fabrics and Garments
US20080295232A1 (en) * 2007-05-08 2008-12-04 Southern Mills, Inc. Systems and methods for dyeing inherently flame resistant fibers without using accelerants or carriers
US20100024103A1 (en) * 2004-08-18 2010-02-04 Southern Mills, Inc. Reflective Printing on Flame Resistant Fabrics
WO2011033145A1 (es) 2009-09-18 2011-03-24 Tag Innovación, S. A. Textil de doble tela
US20110257359A1 (en) * 2007-12-19 2011-10-20 E. I. Du Pont De Nemours And Company Low shrinkage, dyeable mpd-i yarn
US9903073B2 (en) 2013-02-08 2018-02-27 Dupont Teijin Advanced Papers (Japan), Ltd. Colored aramid paper and process for producing same
CN107814928A (zh) * 2017-11-07 2018-03-20 东华大学 一种阳离子染料易染的改性聚间苯二甲酰间苯二胺及其制备方法和应用
WO2021009502A1 (en) 2019-07-12 2021-01-21 Aw Hainsworth And Sons Limited Fire resistant textile material

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3184436A (en) * 1959-09-04 1965-05-18 Du Pont Polycarbonamides of improved dye affinity having the benzene sulfonic acid salt moiety as an integral part of the polymer chain

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3184436A (en) * 1959-09-04 1965-05-18 Du Pont Polycarbonamides of improved dye affinity having the benzene sulfonic acid salt moiety as an integral part of the polymer chain

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3630662A (en) * 1966-09-19 1971-12-28 Celanese Corp Process of dyeing shaped condensation polymer material in heated two-phase dye liquid
US3652199A (en) * 1969-08-28 1972-03-28 Du Pont Process for drying polyamide fibers catonic dyes and zinc thiocyanate
US3673160A (en) * 1970-02-12 1972-06-27 Rhodiaceta Process for producing brilliant sulfonated polyamide-imide fibers and such fibers so produced
US3779705A (en) * 1970-08-14 1973-12-18 Teijin Ltd Process for dyeing fibers or fabrics of aromatic polyamides
US3836327A (en) * 1971-01-08 1974-09-17 Sybron Corp Aromatic alcohol-aromatic aldehyde carrier dyeing of aromatic polyamides
US3900286A (en) * 1971-11-19 1975-08-19 Ciba Geigy Ag Dyestuff preparations and processes for the dyeing of synthetic organic material
US3873338A (en) * 1973-02-28 1975-03-25 Us Air Force Thermal stabilization of polyamide fibers
US3953167A (en) * 1973-07-24 1976-04-27 Teijin Ltd. Process for dyeing fibers or fabrics of aromatic polyamides
US4059403A (en) * 1974-08-10 1977-11-22 Bayer Aktiengesellschaft Process for dyeing wet-spun aromatic polyamides in gel form
US4078889A (en) * 1974-08-10 1978-03-14 Bayer Aktiengesellschaft Process for dyeing dry-spun aromatic polyamides
US4108936A (en) * 1974-08-10 1978-08-22 Bayer Aktiengesellschaft Process for dyeing wet-spun aromatic polyamides in gel form
US4824916A (en) * 1985-03-15 1989-04-25 The Dow Chemical Company Water-insoluble, crosslinked, sulfonated aromatic polyamide
US4741740A (en) * 1986-05-14 1988-05-03 Burlington Industries, Inc. Flame-resistant properties of aramid fibers
US4814222A (en) * 1986-05-14 1989-03-21 Burlington Industries, Inc. Aramid fibers with improved flame resistance
US4895660A (en) * 1986-07-14 1990-01-23 The Dow Chemical Company Water-soluble aromatic polyamides and polyureas
US5404625A (en) * 1990-10-12 1995-04-11 Milliken Research Corporation Method and apparatus for modifying fibers and fabric by impaction with particles
US5298201A (en) * 1990-12-21 1994-03-29 Milliken Research Corporation Method for improving dyeability of fiber and associated fabric utilizing radiation
US5437690A (en) * 1994-05-25 1995-08-01 Springs Industries, Inc. Method for dyeing fibrous materials and dye assistant relating to the same
US5852087A (en) * 1996-02-13 1998-12-22 Teijin Limited Easily dyeable meta-linkage-containing aromatic polyamide fibers
EP0806198A3 (de) * 1996-05-09 2001-07-25 Wella Aktiengesellschaft Färbemittel
US20100024103A1 (en) * 2004-08-18 2010-02-04 Southern Mills, Inc. Reflective Printing on Flame Resistant Fabrics
US20080152888A1 (en) * 2006-09-08 2008-06-26 Southern Mills, Inc. Methods and Systems for Providing Dyed, Stretchable Flame Resistant Fabrics and Garments
EP1902808A1 (en) 2006-09-21 2008-03-26 Louis Wardlaw Enclosure for use during operations for applying heat to at least one conduit member comprising gloved armature means and viewing section ; Method of enclosing a conduit upon which a heating process is to be conducted using such enclosure
US20080295232A1 (en) * 2007-05-08 2008-12-04 Southern Mills, Inc. Systems and methods for dyeing inherently flame resistant fibers without using accelerants or carriers
US20110257359A1 (en) * 2007-12-19 2011-10-20 E. I. Du Pont De Nemours And Company Low shrinkage, dyeable mpd-i yarn
US9080260B2 (en) * 2007-12-19 2015-07-14 E I Du Pont De Nemours And Company Low shrinkage, dyeable MPD-I yarn
WO2011033145A1 (es) 2009-09-18 2011-03-24 Tag Innovación, S. A. Textil de doble tela
US9903073B2 (en) 2013-02-08 2018-02-27 Dupont Teijin Advanced Papers (Japan), Ltd. Colored aramid paper and process for producing same
CN107814928A (zh) * 2017-11-07 2018-03-20 东华大学 一种阳离子染料易染的改性聚间苯二甲酰间苯二胺及其制备方法和应用
CN107814928B (zh) * 2017-11-07 2020-04-21 东华大学 一种阳离子染料易染的改性聚间苯二甲酰间苯二胺及其制备方法和应用
WO2021009502A1 (en) 2019-07-12 2021-01-21 Aw Hainsworth And Sons Limited Fire resistant textile material

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Publication number Publication date
NL6717240A (enrdf_load_html_response) 1968-06-17
LU55113A1 (enrdf_load_html_response) 1968-03-05
FR1548029A (enrdf_load_html_response) 1968-11-29
BE708043A (enrdf_load_html_response) 1968-06-17

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