US3621089A - Process for spinning dye-resistant copolyamide filaments - Google Patents

Process for spinning dye-resistant copolyamide filaments Download PDF

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Publication number
US3621089A
US3621089A US578980A US3621089DA US3621089A US 3621089 A US3621089 A US 3621089A US 578980 A US578980 A US 578980A US 3621089D A US3621089D A US 3621089DA US 3621089 A US3621089 A US 3621089A
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US
United States
Prior art keywords
acid
filaments
stabilizer
copolyamide
basic
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Expired - Lifetime
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US578980A
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English (en)
Inventor
Owen Burchell Edgar
Michael Richard Yates
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • GPHYSICS
    • G21NUCLEAR PHYSICS; NUCLEAR ENGINEERING
    • G21CNUCLEAR REACTORS
    • G21C3/00Reactor fuel elements and their assemblies; Selection of substances for use as reactor fuel elements
    • G21C3/30Assemblies of a number of fuel elements in the form of a rigid unit
    • G21C3/36Assemblies of plate-shaped fuel elements or coaxial tubes
    • 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E30/00Energy generation of nuclear origin
    • Y02E30/30Nuclear fission reactors

Definitions

  • ABSTRACT A terpolyamide, formed from reactants polymerized in the presence of the equivalent of at least 3.0 mole percent of a monofunctional acid or basic stabilizer, is melt spun into filaments which are subsequently cold drawn.
  • PROCESS FOR SPINNING DYE-RESISTANT COPOLYAMIDE ILAMENTS The present invention is concerned with filaments formed from copolyamides which resist dyeing by acid or basic dyestufis.
  • Polyamide yarns, and fabrics made therefrom, are normally dyed with disperse or acid dyestuffs, basic dyestuffs being seldom used at present. in some end uses it is desirable that not all of the yarns employed should be dyed to the same extent by one of the above classes of dyestuffs, so that in piece dyeing, for example, contrast dyeing and other effects may be obtained. In order to achieve these effects some polyamide yarns are modified, e.g., chemically. in order to resist dyeing by, usually, acid dyestuffs. Such yarns are known as dye-resist yams. it is of course important that the modifications made to the yarns should in no way impair their desirable characteristics, and that physical properties of the different yarns should be as nearly as possible identical.
  • copolyamides may be prepared which, while having substantially the same softening points as polyhexamethylene adipamide have considerably higher melt viscosities at the same, or nearly the same molecular weights.
  • copolyamides referred to are ternary copolymers of polyhexamethylene adipamide and polyhexamethylene terephthalamide together with a minor proportion of a third component such as polyhexamethylene isophthalamide or polyepsilon caprolactam.
  • the molecular weight of these ternary copolyamides can be decreased by the addition of relatively large amounts of a molecular weight stabilizer, for example an acid, without reducing the melt viscosities thereof to levels at which they cannot be melt spun as would normally be the case.
  • a molecular weight stabilizer for example an acid
  • the filaments obtained from copolyamides prepared in the presence of a relatively large amount of an acid stabilizer by the normal processes of melt spinning and drawing are resistant to acid dyeing.
  • Use of correspondingly large amounts of a basic stabilizer would of course, render the yarns resistant to basic dyeing.
  • Such filaments would, of course, also be useful in deep dye filaments since the large number of amine end groups available as a result of the addition of a basic stabilizer would make the filaments particularly suitable for acid dyeing.
  • the present invention provides a process for the manufacture of polyamide filaments by melt spinning and subsequently cold drawing a copolyamide having a melt viscosity of at least 400 poisis at 290 C, wherein said copolyamide comprises at least 50 percent by weight of polyhexamethylene adipamide together with 20 percent to 40 percent by weight of polyhexamethylene terephthalate and from 2 to 20 percent by weight of a third polyamide and is formed by the polymerization of a mixture of hexamethylene diammonium adipate, hexamethylene diammonium terephthalate and a third polyamide forming salt or lactam in the presence of the equivalent of at least 3.0 mole percent of a monofunctional acid or basic stabilizer.
  • the expression the equivalent of at least 3.0 mole percent of a monofunctional acid or basic stabilizer includes a difunctional stabilizer present in an amount equivalent to at least 3.0 mole percent of a monofunctional stabilizer.
  • stabilizer is meant the acid or basic compound, e.g., acetic acid, normally added to a polyamide fonning salt to control the molecular weight thereof.
  • the third polyamide forming salt or lactam in the mixture constitutes 5 to ID percent thereof and is hexamethylene diammonium isophthalate or epsilon caprolactam.
  • the stabilizer may be an acid and is preferably a dibasic acid such as adipic acid or terephthalic acid.
  • the yarn was knitted on a circular stocking machine together with a 66 nylon control and the fabric was dyed with Solway Blue B. A distinct shade difference was visible between the panels and after overdyeing with Dispersal fast Yellow A the panel containing the copolymer yarn was yellow and the 66 nylon control panel green.
  • Filaments spun from the copolymers were resistant to acid dyeing.
  • EXAMPLE IV TABLE 3 Properties of 6.6/6T/6 copolyamide stabilized with 2 mole percent of hexamethylene diamine 16 .1045 noises an Amine end group equivalents per l0 3. Carboxyl end group equivalents per l0 g. Melt viltcoulty Filaments spun from the copolymer were resistant to basic dyestuffs, but dyed well with acid dyes.
  • a process for the manufacture of drawn terpolyamide filaments comprising melt spinning into filaments terpolyamide having a melt viscosity of at least 400 poises at 290C. and formed by the polymerization of a mixture of hexamethylene diammonium adipate, hexamethylene diammonium terephthalate and a third polyamide forming member selected from the group consisting of hexamethylene diammonium isophthalate and epsilon caprolactam in the presence of the equivalent of at least 3.0 mole percent of a monofunctional acid or basic stabilizer, and subsequently cold drawing the said filaments.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plasma & Fusion (AREA)
  • General Engineering & Computer Science (AREA)
  • High Energy & Nuclear Physics (AREA)
  • Polyamides (AREA)
  • Artificial Filaments (AREA)
US578980A 1965-09-16 1966-09-13 Process for spinning dye-resistant copolyamide filaments Expired - Lifetime US3621089A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB39588/65A GB1114542A (en) 1965-09-16 1965-09-16 Dye-resist copolyamide filaments

Publications (1)

Publication Number Publication Date
US3621089A true US3621089A (en) 1971-11-16

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ID=10410378

Family Applications (1)

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US578980A Expired - Lifetime US3621089A (en) 1965-09-16 1966-09-13 Process for spinning dye-resistant copolyamide filaments

Country Status (7)

Country Link
US (1) US3621089A (nl)
BE (1) BE687016A (nl)
CH (1) CH482847A (nl)
DE (1) DE1669455A1 (nl)
GB (1) GB1114542A (nl)
LU (1) LU51970A1 (nl)
NL (1) NL6613152A (nl)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3926924A (en) * 1965-09-16 1975-12-16 Ici Ltd Polyamide copolymers from hexamethylene diammonium adipate/terephthalate and a third polyamide forming reactant
US4076696A (en) * 1976-12-09 1978-02-28 Chevron Research Company Extrusion of polypyrrolidone
US4521484A (en) * 1984-06-07 1985-06-04 E. I. Du Pont De Nemours And Company Self-crimping polyamide filaments
US5081222A (en) * 1987-07-17 1992-01-14 Basf Aktiengesellschaft Partly aromatic copolyamide of reduced triamine content
US5223196A (en) * 1990-11-20 1993-06-29 E. I. Du Pont De Nemours And Company Processing of pigmented nylon fibers using modified polymers
US5298595A (en) * 1987-07-17 1994-03-29 Basf Aktiengesellschaft Partly aromatic copolyamides of reduced triamine content
US5422420A (en) * 1990-11-20 1995-06-06 E. I. Du Pont De Nemours And Company Terpolyamides and multipolyamides containing amide units of 2-methylpentamethylenediamine and products prepared therefrom
US5504146A (en) * 1988-02-12 1996-04-02 Basf Aktiengesellschaft Toughened partly aromatic copolyamides

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1581745A (en) 1976-03-30 1980-12-17 British Industrial Plastics Hot melt adhesive
US20060030693A1 (en) 2004-07-27 2006-02-09 Martens Marvin M Process for the preparation of thermoplastic polyamide and polyester compositions exhibiting increased melt flow and articles formed therefrom

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2163584A (en) * 1936-12-01 1939-06-27 Du Pont Preparation of polyamides
US2252555A (en) * 1939-04-04 1941-08-12 Wilmington Trust Co Polymeric material
US3322731A (en) * 1962-05-22 1967-05-30 Du Pont Interpolymers of caprolactam, hexamethylene diamine, adipic acid and sebacic acid
US3376369A (en) * 1964-03-13 1968-04-02 Du Pont Process for making molecular oriented fibers of polymerized lactams
US3380968A (en) * 1965-05-21 1968-04-30 Monsanto Co Novel terpolyamides from phenylindan carboxylic acid
US3383369A (en) * 1965-05-24 1968-05-14 Monsanto Co Novel terpolyamides of aliphatic and aromatic acids and process
US3388099A (en) * 1965-05-14 1968-06-11 Monsanto Co Terpolyamides
US3454536A (en) * 1964-11-12 1969-07-08 Chemische Werke Witten Gmbh Process for the preparation of polyamides
US3475387A (en) * 1963-08-31 1969-10-28 British Nylon Spinners Ltd Manufacture of polyamides from aromatic dicarboxylic acids
US3500498A (en) * 1966-05-28 1970-03-17 Asahi Chemical Ind Apparatus for the manufacture of conjugated sheath-core type composite fibers

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2163584A (en) * 1936-12-01 1939-06-27 Du Pont Preparation of polyamides
US2252555A (en) * 1939-04-04 1941-08-12 Wilmington Trust Co Polymeric material
US3322731A (en) * 1962-05-22 1967-05-30 Du Pont Interpolymers of caprolactam, hexamethylene diamine, adipic acid and sebacic acid
US3475387A (en) * 1963-08-31 1969-10-28 British Nylon Spinners Ltd Manufacture of polyamides from aromatic dicarboxylic acids
US3376369A (en) * 1964-03-13 1968-04-02 Du Pont Process for making molecular oriented fibers of polymerized lactams
US3454536A (en) * 1964-11-12 1969-07-08 Chemische Werke Witten Gmbh Process for the preparation of polyamides
US3388099A (en) * 1965-05-14 1968-06-11 Monsanto Co Terpolyamides
US3380968A (en) * 1965-05-21 1968-04-30 Monsanto Co Novel terpolyamides from phenylindan carboxylic acid
US3383369A (en) * 1965-05-24 1968-05-14 Monsanto Co Novel terpolyamides of aliphatic and aromatic acids and process
US3500498A (en) * 1966-05-28 1970-03-17 Asahi Chemical Ind Apparatus for the manufacture of conjugated sheath-core type composite fibers

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Bulletin of the Oyonite Chemical Co., Bulletin No. 10 (revised Apr. 22, 1955), U.S. Pat. Office Scientific Library, received Nov. 27, 1957, composed of a total of 63 pages; 4 pages, excerpts. *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3926924A (en) * 1965-09-16 1975-12-16 Ici Ltd Polyamide copolymers from hexamethylene diammonium adipate/terephthalate and a third polyamide forming reactant
US4218509A (en) * 1965-09-16 1980-08-19 Imperial Chemical Industries, Limited Polyamide copolymers
US4076696A (en) * 1976-12-09 1978-02-28 Chevron Research Company Extrusion of polypyrrolidone
US4521484A (en) * 1984-06-07 1985-06-04 E. I. Du Pont De Nemours And Company Self-crimping polyamide filaments
US5081222A (en) * 1987-07-17 1992-01-14 Basf Aktiengesellschaft Partly aromatic copolyamide of reduced triamine content
US5298595A (en) * 1987-07-17 1994-03-29 Basf Aktiengesellschaft Partly aromatic copolyamides of reduced triamine content
US5504146A (en) * 1988-02-12 1996-04-02 Basf Aktiengesellschaft Toughened partly aromatic copolyamides
US5223196A (en) * 1990-11-20 1993-06-29 E. I. Du Pont De Nemours And Company Processing of pigmented nylon fibers using modified polymers
US5391703A (en) * 1990-11-20 1995-02-21 E. I. Du Pont De Nemours And Company Polyamide pigment dispersion
US5422420A (en) * 1990-11-20 1995-06-06 E. I. Du Pont De Nemours And Company Terpolyamides and multipolyamides containing amide units of 2-methylpentamethylenediamine and products prepared therefrom

Also Published As

Publication number Publication date
LU51970A1 (nl) 1966-11-15
DE1669455A1 (de) 1969-10-16
GB1114542A (en) 1968-05-22
CH482847A (de) 1969-12-15
NL6613152A (nl) 1967-03-17
BE687016A (nl) 1967-03-16

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