US3128221A - Dye receptive filament - Google Patents

Dye receptive filament Download PDF

Info

Publication number
US3128221A
US3128221A US173892A US17389262A US3128221A US 3128221 A US3128221 A US 3128221A US 173892 A US173892 A US 173892A US 17389262 A US17389262 A US 17389262A US 3128221 A US3128221 A US 3128221A
Authority
US
United States
Prior art keywords
copolymer
filament
dye
isophthalamide
nylon
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US173892A
Other languages
English (en)
Inventor
Flores Juan Antonio
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to NL137598D priority Critical patent/NL137598C/xx
Priority to NL276647D priority patent/NL276647A/xx
Priority to GB170462A priority patent/GB978171A/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to US173892A priority patent/US3128221A/en
Priority to DEP29039A priority patent/DE1238155B/de
Priority to CH361262A priority patent/CH419439A/de
Priority to CH98864A priority patent/CH404077A/de
Priority to GB12070/62A priority patent/GB965815A/en
Priority to BE615856A priority patent/BE615856A/fr
Priority to FR892911A priority patent/FR1318577A/fr
Application granted granted Critical
Publication of US3128221A publication Critical patent/US3128221A/en
Priority to MY196874A priority patent/MY6800074A/xx
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • 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
    • D01F8/00—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof
    • D01F8/04—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers
    • D01F8/12—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one polyamide as constituent
    • 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
    • C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic 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
    • D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
    • D01F6/80—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyamides
    • 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
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2929—Bicomponent, conjugate, composite or collateral fibers or filaments [i.e., coextruded sheath-core or side-by-side type]
    • Y10T428/2931—Fibers or filaments nonconcentric [e.g., side-by-side or eccentric, etc.]
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer
    • Y10T428/2969—Polyamide, polyimide or polyester

Definitions

  • This invention relates generally to synthetic linear polycarbonamides and, more particularly, to a copolyamide of poly(hexamethylene adipamide) which, when spun and otherwise processed in a conventional manner, yields fabrics having a unique combination of rapid dyeability and a high level of retained physical properties as compared to fabrics produced from a 66 nylon homopolymer.
  • Poly(hexarnethylene adipamide) is Well known for superior textile properties such as tenacity, resilience, wear resistance and the like. However, it is also known that textile products produced therefrom do not dye rapidly and uniformly. Previous attempts to remedy this defect by copolyrnerization with other polyamide-forming components have resulted in an intolerable loss in physical properties such as tenacity and yarn stability.
  • the most important object of the present invention is to provide a copolyamide textile filament having physical properties substantially equivalent to those of 66 nylon as well as a high dye absorption rate and improved uniformity of dyeing.
  • This copolyamide is readily prepared under conventional polyamidation conditions and no special equipment is required. Likewise, it can be spun and drawn on conventional equipment.
  • the tensile properties of the co polyamide filament are substantially equivalent to 66 nylon as will be shown hereinafter. In contrast, the rate of dye penetration is nearly ten times as rapid as for a corresponding filament of 66 nylon.
  • the appended drawing consists of a graph showing the effect of copolymer composition on the tenacity of and dye penetration into the copolymer filament of the present invention.
  • the dye rate is measured by immersing a skein of yarn weighing 15 grams in a test tube containing a solution of 0.001 gram per milliliter of the cobalt complex dye disclosed in Example III of German Patent 743,155 (1943) and known as Perlon Fast Red 3B5.
  • the solution is maintained at the test temperature (55 C. in the following examples).
  • the test tube is placed between a light source and a photocell and the light absorption of the solution is measured as a function of time, as the dye is taken up by the fiber. The reciprocal of the time elapsed until the absorption rate has dropped to one half the original value is a measure of the dye rate.
  • the uniformity of dye penetration is determined by irrunersing skeins of test yarn in a bath containing 1 gram of Color Index Number Acid Blue 113 in 4 liters of water, maintained at a temperature of 80-90 C. The amount of dye is in excess of that required for saturation dyeing.
  • the skeins are removed, rinsed, dried and cross-sections are examined under a microscope. The percentage of radial penetration of the dye is easily measured.
  • the copolyamide of this invention has also been found to be particularly useful as one component of a composite filament consisting of two or more components held together in eccentric relationship as described in US. Patent No. 2,931,091.
  • the copolyamide may be extruded in side-by-side relationship from the same orifices of a spinneret with another polymer such as 66 or 6 nylon to produce two-component structures which, after conventional quenching and drawing, may be crimped by exposure to boiling water or otherwise to produce very desirable elfects in fabrics.
  • sheath-core structures may be produced with the copolymer in either the sheath or core position.
  • Example I A 48% aqueous solution of nylon salt is prepared.
  • the salt component consists of 92% by weight hexamethylene diammonium adipate and 8% hexamethylene diammonium isophthalate.
  • To the solution is added 0.03% of excess hexamethylene diamine, to serve as a viscosity stabilizer.
  • This solution is charged to an evaporator, concentrated to about at 13 p.s.i. and transferred to an autoclave previously purged with oxygen free gas.
  • the mixture is heated under autogenous steam pressure until 250 p.s.i. is reached, requiring about twenty minutes. Steam is then bled off while maintaining a pressure of 250 p.s.i. Heating is continued until the nominal salt concentration is about corresponding to a temperature of 230 C.
  • the flake is charged to a grid melter and blanketed with an atmosphere of steam as disclosed by Waltz in US. Patent 2,571,975.
  • Molten polymer issuing from the melter is pumped through a filter pack to a spinneret of 34 holes at a temperature of 288 C., extruded, quenched, steamed, contacted with a liquid finish and Wound up on a package.
  • the filaments are then drawn four times their extruded length to form a 70 denier yarn.
  • the dye rate (at 55 C.) of the thus-prepared copolymer yarn is determined, using the procedure previously described.
  • Example II Percent Tenacity, Percent Sample No. 6-I g.p.d. Dye Penetration
  • Example III 66 nylon flake having a relative viscosity of 45 is prepared in the conventional manner.
  • the 66 nylon fiake and 66/ 61 flake, prepared as described in Example I, are melted separately in screw melters and extruded in sideby-side relation from holes in a spinneret of the type shown in FIG. 6 of U.S. Patent No. 2,931,091 to produce filaments containing about 50% of the copolymer.
  • the spinneret has 34 holes.
  • the filaments are quenched by passing air transversely across the filament bundle as described in U.S. Patent No. 2,273,105.
  • the filaments are then wound into a package in the conventional manner.
  • the filaments are subsequently withdrawn from the package and drawn to a ratio of 2.66.
  • the yarn is then passed through a steam tube at 381 yards per minute and permitted to relax 11% as illustrated in U.S. Patent No. 3,003,222.
  • the steam tube is 2 inches in length and is supplied with steam at 175 C. and 12 p.s.i.
  • the yarn is then interlaced with an air jet as described in U.S. Patent No. 2,985,995 and wound into a package in the conventional manner.
  • the filaments develop about ten crimps per inch.
  • the resulting fabric has excellent bulk, liveliness and dryness and the excellent dyeing characteristics of the copolymer are carried over to the two-component fiber.
  • the copolymer component is the load-bearing component with the result that the same relationship illustrated in this graph for single component filaments is equally applicable to the exemplified two component filamcnts.
  • the copolymer composition of this invention is that it can be processed on conventional 66 nylon equipment, with only minor changes in processing conditions.
  • the polymer can be prepared in a conventional autoclave or it can be made in a continuous polymerizer. Due to a slightly slower reaction rate, slightly longer reaction cycles should be employed. Spinning and drawing processes are likewise conventional with the exception that a higher melt viscosity is encountered. This normally requires a filter pack with a smaller amount of fine sand.
  • the polymer may be spun directly from a continuous polymerizer, or the flake may be melted on a grid or a screw melter may be used. Conventional drawing equipment for 66 nylon is satisfactory.
  • the yarn may be drawn over an unheated snubbing pin or, alternatively, a heated pin may be employed.
  • the yarn may be drawn in a single stage or in two or more stages; it may be after-treated with steam or hot air to anneal or relax the yarn. It may be bulked, crimped, twisted, false-twisted and set, according to the requirements for a particular end use.
  • the copolymer of this invention may contain the usual additives for polyamides, including delusterants, such as those disclosed in U.S. Patent No. 2,205,722, pigments, antioxidants, such as those disclosed in U.S. Patent No. 2,510,777 or light stabilizers, such as those disclosed in U.S. 2,887,462. It may be used as a monofilament, e.g., in hosiery, or as a multifilament yarn as disclosed in the examples. It is also suitable for extrusion simultaneously with filaments of one or more other polyamides, to form a mixed filament yarn, as disclosed more fully in the copending application of Knospe, filed on March 31, 1961, and bearing Serial No. 99,883.
  • the filaments may be extruded as round, trilobal, ribbon or other cross sections.
  • the copolymer of this invention is particularly useful as one component of a two or multicomponent filament (Example III).
  • the copolymer may be combined with other components having a lower shrinkage potential to produce crimped or crirnpable filaments which may be used to prepare fabrics of improved aesthetics and excellent dyeability.
  • the preferred polyamides for use in conjunction with the copolymer of this invention in multicomponent filaments are polyhexamethylene adipamide and polycaproamide.
  • Various other suitable polyarnides and copolyamides may be selected from those disclosed in U.S. Patents Nos. 2,071,250, 2,071,253, 2,130,523, 2,465,319, 2,130,948, and 2,190,770.
  • the products disclosed herein are particularly useful in the production of textile fabrics, especially those which are to be dyed.
  • the filaments may be used as such or converted to staple and used in 100% synthetic yarns or in blends with other fibers, natural, artificial, or manmade.
  • Other variations and adaptations in the end use may be made without departing from the spirit of the present invention which is therefore intended to be limited only by the scope of the appended claims.
  • a drawn nylon filament consisting essentially of a copolymer of polyhexamethylene adipainide and polyhexamethylene isophthalamide, there being less than 10% by weight of the isophthalamide in the copolymer.
  • the filament of claim 1 containing more than 4% by weight of the isophthalamide.
  • a drawn nylon filament consisting essentially of a copolymer of polyhexamethylene adipamide and polyhexamethylene isophthalamide, the latter being present in the range of from 59% by weight of the copolymer.
  • a high shrinkage, dye receptive filament consisting essentially of a copolymer of polyhexamethylene adipamide and polyhexamethylene isophthalamide, said copolymer containing more than by weight of the adipamide.
  • a drawn nylon filament comprising at least two continuous adhered components, one of said components consisting essentially of a homopolyamide, another component consisting essentially of a copolymer of polyhexamethylene adipamide and polyhexamethylene isophthalamide, there being less than 10% by weight of the isophthalamide in the copolymer.
  • a drawn nylon filament comprising a copolymer of polyhexamethylene adipamide and polyhexamethylene isophthalamide, there being less than 10% by weight of the isophthalamide in the copolymer.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Artificial Filaments (AREA)
  • Multicomponent Fibers (AREA)
  • Amplifiers (AREA)
US173892A 1961-03-31 1962-02-19 Dye receptive filament Expired - Lifetime US3128221A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
NL137598D NL137598C (nl) 1961-03-31
NL276647D NL276647A (nl) 1961-03-31
GB170462A GB978171A (nl) 1961-03-31 1962-01-17
US173892A US3128221A (en) 1961-03-31 1962-02-19 Dye receptive filament
DEP29039A DE1238155B (de) 1961-03-31 1962-03-22 Faeden aus einem Polyamid-Mischpolymerisat
CH98864A CH404077A (de) 1961-03-31 1962-03-26 Gefärbtes Textilgut aus Copolyamid
CH361262A CH419439A (de) 1961-03-31 1962-03-26 Faden aus Polyamid und Verfahren zu seiner Herstellung
GB12070/62A GB965815A (en) 1961-03-31 1962-03-29 Copolyamide filaments and process for their production
BE615856A BE615856A (fr) 1961-03-31 1962-03-30 Nouveau copolyamide et procédé pour sa préparation
FR892911A FR1318577A (fr) 1961-03-31 1962-03-30 Nouveau copolyamide et procédé pour sa préparation
MY196874A MY6800074A (en) 1961-03-31 1968-12-31 Improvements in or relating to the recording of signals

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9980361A 1961-03-31 1961-03-31
US173892A US3128221A (en) 1961-03-31 1962-02-19 Dye receptive filament

Publications (1)

Publication Number Publication Date
US3128221A true US3128221A (en) 1964-04-07

Family

ID=26796492

Family Applications (1)

Application Number Title Priority Date Filing Date
US173892A Expired - Lifetime US3128221A (en) 1961-03-31 1962-02-19 Dye receptive filament

Country Status (8)

Country Link
US (1) US3128221A (nl)
BE (1) BE615856A (nl)
CH (2) CH419439A (nl)
DE (1) DE1238155B (nl)
FR (1) FR1318577A (nl)
GB (2) GB978171A (nl)
MY (1) MY6800074A (nl)
NL (2) NL276647A (nl)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5371132A (en) * 1992-06-25 1994-12-06 Asahi Kasei Kogyo Kabushiki Kaisha Polyamide resin composition and molded articles obtained therefrom

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1481960A (fr) * 1966-01-10 1967-05-26 Societe D'etudes, Recherches Et Constructions Electroniques Procédé et dispositif de codage numérique
EP2581400B1 (en) * 2010-06-11 2017-03-29 Asahi Kasei Kabushiki Kaisha Polyamide and polyamide composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR873983A (fr) * 1939-08-29 1942-07-24 Ig Farbenindustrie Ag Procédé de fabrication de polyamides linéaires de hauts degrés de polymérisation
US2742496A (en) * 1952-09-19 1956-04-17 California Research Corp Process for separating hexamethylene diamine salts of isophthalic and terephthalic acids
US2931091A (en) * 1954-02-26 1960-04-05 Du Pont Crimped textile filament
US2965616A (en) * 1957-01-24 1960-12-20 Eastman Kodak Co Linear polyamides from aliphatic dicarboxy compounds and aliphatic diamines upgraded with trans-1, 4-cyclohexanedicarboxylic acid

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE894769C (de) * 1944-10-11 1953-10-26 Basf Ag Verfahren zur Herstellung von Loesungen von Mischpolyamiden
US2766221A (en) * 1953-06-04 1956-10-09 California Research Corp Synthetic fiber-forming polymers from meta-xylylene diamine and adipic acid

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR873983A (fr) * 1939-08-29 1942-07-24 Ig Farbenindustrie Ag Procédé de fabrication de polyamides linéaires de hauts degrés de polymérisation
US2742496A (en) * 1952-09-19 1956-04-17 California Research Corp Process for separating hexamethylene diamine salts of isophthalic and terephthalic acids
US2931091A (en) * 1954-02-26 1960-04-05 Du Pont Crimped textile filament
US2965616A (en) * 1957-01-24 1960-12-20 Eastman Kodak Co Linear polyamides from aliphatic dicarboxy compounds and aliphatic diamines upgraded with trans-1, 4-cyclohexanedicarboxylic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5371132A (en) * 1992-06-25 1994-12-06 Asahi Kasei Kogyo Kabushiki Kaisha Polyamide resin composition and molded articles obtained therefrom

Also Published As

Publication number Publication date
DE1238155B (de) 1967-04-06
FR1318577A (fr) 1963-02-15
NL137598C (nl)
CH404077A (de) 1966-06-30
CH98864A4 (nl) 1965-08-31
GB978171A (nl) 1964-12-16
BE615856A (fr) 1962-10-01
MY6800074A (en) 1968-12-31
NL276647A (nl)
GB965815A (en) 1964-08-06
CH419439A (de) 1966-08-31

Similar Documents

Publication Publication Date Title
US5445884A (en) Multi-lobal composite filaments with reduced stainability
US3389549A (en) Aromatic dicarbonyl sulfonate modified polycarbonamides
US3418199A (en) Crimpable bicomponent nylon filament
US3593513A (en) Dyeing of mixed synthetic polymeric yarns
US4521484A (en) Self-crimping polyamide filaments
US3998042A (en) Mixed shrinkage yarn
US3681910A (en) Composite yarn product
US5559194A (en) Modified nylon fibers
DE60208081T3 (de) Verfahren zur herstellung von polyamidmischgarnen
US5093061A (en) Deep dyeing conjugate yarn processes
US3128221A (en) Dye receptive filament
US4721755A (en) Fibers and yarns from a blend of aromatic polyamides
US3939636A (en) Mixed yarn
US3328341A (en) Polyamides containing butyrolactone
JPS6052616A (ja) ポリアミドモノフイラメントおよびその製造方法
EP0228224B1 (en) Aromatic polyamide fibers and processes for making such fibers
US6524503B2 (en) Process for the manufacture of polyamide yarns dyeable in melange shades
US3664917A (en) Two-component polyamide yarns
US3720576A (en) Crimped composite fibers and process for preparation thereof
JPS5830407B2 (ja) ポリカプラミドフイラメントヤ−ン
US4845934A (en) False twisted bulky multifilament yarn, method of making and end use of this yarn
US3475111A (en) Tone-on-tone acid dyeing blended textile of nylon and nylons with small amounts of phthalic acid sulfonic acid,phosphoric or phosphonic acid ester condensed therein and the textile so produced
IE43335B1 (en) Composite bicomponent polyamide filaments
BR112020007709A2 (pt) fibras têxteis de náilon de alta capacidade de suporte de carga com aditivo, fios e tecidos combinados dos mesmos
US3542745A (en) Terpolyamides useful in preparing textile fibers consisting essentially of nylon 66,nylon 6,and nylon 2-6ia