US3274312A - Process for preparing dye-receptive shaped articles - Google Patents

Process for preparing dye-receptive shaped articles Download PDF

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Publication number
US3274312A
US3274312A US244943A US24494362A US3274312A US 3274312 A US3274312 A US 3274312A US 244943 A US244943 A US 244943A US 24494362 A US24494362 A US 24494362A US 3274312 A US3274312 A US 3274312A
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United States
Prior art keywords
mix
dye
shaped articles
fibers
prepared
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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
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US244943A
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English (en)
Inventor
Compostella Mario
Latella Giovanni
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Montedison SpA
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Montedison SpA
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Classifications

    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/04Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polyolefins
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10Homopolymers or copolymers of propene
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00General methods for the manufacture of artificial filaments or the like
    • D01F1/02Addition of substances to the spinning solution or to the melt
    • D01F1/10Other agents for modifying properties
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00Applications
    • C08L2203/12Applications used for fibers

Definitions

  • the present invention relates to a process for preparing dye-receptive shaped articles such as textile fibers, films, sheets, tapes, etc., from alpha-olefin polymers.
  • Processes used for obtaining, for example, textile fibers comprise:
  • any suitable continuous or discontinuous apparatus capable of supplying heat may be employed for the sintering step.
  • 150% of polycondensate may be mixed with 50-99% of polyolefin.
  • the method of the present invention more particularly, 1
  • polyolefins and basic nitrogen polycondensates obtained by reacting (in the presence or absence of solvents and condensing agents) (1) epichlorohydrin, (2) one or more primary C C or secondary C C aliphatic amines and then subjecting the condensation product to a further condensation with one or more aliphatic, aromatic or heterocyclic secondary diamines.
  • These condensates show generally a softening point under C., an intrinsic viscosity (determined in a 1% isopropanol solution) of 005-05 and a nitrogen content up to 35%.
  • the shaped articles such as fibers are then prepared by extruding the granules sintered according to the invention.
  • the mixes to be extruded contain polyolefins, from 1 to 25% by weight of the nitrogen polycondensate and, if desired, 0.1 to 5% of a solid dispersing agent for dispersing the nitrogen condensate in the molten mass.
  • Suitable solid dispersing agents include: cetyl and stearyl alcohols, stearic acid, benzoin, furoin, vinyl stearate, mono-, dior tristearic esters of glycerol, monoethanolamine stearate, stearic amide, C to C aliphatic amines, condensation products of ethylene oxide with alcohols, amines or phenols, polystearamide, polyacrylic acid, polystyrene, styrene copolymers, terpene polymers, etc.
  • the sintering and spinning operations according to the present invention may be conveniently carried out under oxygen-free nitrogen.
  • the fibers produced may be in the form of monoor pluro-filaments and can be employed for preparing continuous fibers or staples or for preparing either bulky yarns or staples.
  • the monoor plum-filaments prepared according to the present invention can be subjected to treatments for the water-insolubilization of the basic nitrogen compound.
  • Particularly useful for this purpose are the treatments with formaldehyde, diisocyanates, diepoxy compounds or various cross-linking agents such as divinyl benzene or the like. These treatments may be carried out either before or after stretching.
  • the stretching is preferably executed using ratios between 1:2 and 1:10 at temperatures between 80 and C. in stretching devices heated with hot air, steam or similar fluids.
  • the fibers thus obtained can be dyed with acid dyes or with plastosoluble dyes. They also exhibit a good aflinity for basic and vat dyestuffs.
  • the sintered granules prepared according to the present invention are also suitable for extrusion into films, tapes and various other shaped articles.
  • Stereospecific catalysts such as those disclosed by Natta et a1. or shown in Italina Patent 526,101, are examples of suitable catalysts.
  • Shaped articles, especially fibers obtained from polyproylene containing predominant amounts (more than 50%) of isotactic macromolecules are of particular interest.
  • the residue of the heptane extraction is an indication of the presence of isotactic macromolecules.
  • Example 1 A mix is prepared from:
  • the mix is then sintered in a machine for preparing tablets.
  • the residence time of the mix in the sintering machine is 1 second, and this device reaches a temperature of 90 C.
  • the sintered granules are then spun in a melt spinning device under the following conditions:
  • Screw temperature C. 250 Head temperature
  • Acid black JVS Acid dye Lanasyn red 2GL Metallized dye. Setacyl yellow 3G Plastosoluble dye. Cibacet scarlet BR Plastosoluble dye. Acetoquinone blue RHO Plastosoluble dye.
  • Example 2 A mix is prepared from:
  • the mix is then sintered in a device for the preparation of tablets.
  • the residence time of the mix in the sinterization device is 1 second and the mix reaches a temperature of 100 C.
  • the sintered granules are spun in a melt spinning device under the following conditions:
  • Screw temperature C. 260 Head temperature
  • C. 265 Spinneret temperature C. 265 Spinneret type
  • mm 198 x 0.8 x 16 Maximum pressure, kg./cm. 100
  • the fibers thus prepared have a clear color and their residual intrinsic viscosity amounts to of the initial value.
  • the fibers after being stretched at 130 C. inthe presence of steam with a stretching ratio of 1:5, exhibit the following serimetric characteristics:
  • Acid black IVS Acid dye Lanasyn red 2G1 Metallized dye. Setacyl yellow 3G Plastosoluble dye. Cibacet scarlet BR Plastosoluble dye. Acetoquinone blue Plastosoluble dye.
  • Example 3 A mix is prepared from:
  • the mixture is then sintered in a device for the preparation of pellets using a residence time in the sintering device of 1 sec.
  • the mix is heated to a temperature of 80 C. in this device.
  • the centered granules are spun in a melt spinning device under the following conditions:
  • Acid black IVS Acid dye Lanasyn red 26L Metallized dye. Setacyl yellow 36 Plastosoluble dye. Cibacet scarlet BR Plastosoluble dye. Acetoquino-ne blue RHO Plastosoluble dye.
  • the basic nitrogen polycondensate is prepared by reacting 1 mol of a compound from (a), 1 to 3 mols of epichlorohydrin and 0.1 to 10 mols of a bissecondary diamine from (c).
  • the amine of (a) is selected from the group consisting of n-dodecylamine, hexadecylamine, octadecylamine, dioctadecylamine, dioctylamine or salts thereof.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Artificial Filaments (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Coloring (AREA)
US244943A 1961-12-21 1962-12-17 Process for preparing dye-receptive shaped articles Expired - Lifetime US3274312A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT2280961 1961-12-21

Publications (1)

Publication Number Publication Date
US3274312A true US3274312A (en) 1966-09-20

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US244943A Expired - Lifetime US3274312A (en) 1961-12-21 1962-12-17 Process for preparing dye-receptive shaped articles

Country Status (9)

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US (1) US3274312A (US06338842-20020115-C00009.png)
AT (1) AT241677B (US06338842-20020115-C00009.png)
BE (1) BE626339A (US06338842-20020115-C00009.png)
DE (1) DE1218655B (US06338842-20020115-C00009.png)
DK (1) DK114993B (US06338842-20020115-C00009.png)
ES (1) ES283581A1 (US06338842-20020115-C00009.png)
FR (1) FR1341351A (US06338842-20020115-C00009.png)
GB (1) GB1006582A (US06338842-20020115-C00009.png)
NL (1) NL286762A (US06338842-20020115-C00009.png)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3917817A (en) * 1971-11-29 1975-11-04 Oreal Hair treating cosmetic compositions containing piperazine based cationic polymer
US4013787A (en) * 1971-11-29 1977-03-22 Societe Anonyme Dite: L'oreal Piperazine based polymer and hair treating composition containing the same

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2945010A (en) * 1956-10-24 1960-07-12 Eastman Kodak Co Preparing polyester fibers of improved dyeability using aromatic amines
FR1245063A (fr) * 1958-11-12 1960-11-04 Montedison Spa Perfectionnements au filage des polymères viscoélastiques
US3013998A (en) * 1956-09-27 1961-12-19 Montedison Spa Dyeable compositions, articles formed therefrom and methods for making said articles
US3059275A (en) * 1959-04-27 1962-10-23 Clarence W Vogt Method and apparatus for making selfsustaining pellets of plastic materials
US3098697A (en) * 1956-12-12 1963-07-23 Dichloroethane
US3151928A (en) * 1960-05-05 1964-10-06 Montedison Spa Process for improving the tinctorial characteristics of polyolefin fibres

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3013998A (en) * 1956-09-27 1961-12-19 Montedison Spa Dyeable compositions, articles formed therefrom and methods for making said articles
US2945010A (en) * 1956-10-24 1960-07-12 Eastman Kodak Co Preparing polyester fibers of improved dyeability using aromatic amines
US3098697A (en) * 1956-12-12 1963-07-23 Dichloroethane
FR1245063A (fr) * 1958-11-12 1960-11-04 Montedison Spa Perfectionnements au filage des polymères viscoélastiques
US3059275A (en) * 1959-04-27 1962-10-23 Clarence W Vogt Method and apparatus for making selfsustaining pellets of plastic materials
US3151928A (en) * 1960-05-05 1964-10-06 Montedison Spa Process for improving the tinctorial characteristics of polyolefin fibres

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3917817A (en) * 1971-11-29 1975-11-04 Oreal Hair treating cosmetic compositions containing piperazine based cationic polymer
US4013787A (en) * 1971-11-29 1977-03-22 Societe Anonyme Dite: L'oreal Piperazine based polymer and hair treating composition containing the same

Also Published As

Publication number Publication date
AT241677B (de) 1965-08-10
ES283581A1 (es) 1963-07-01
BE626339A (US06338842-20020115-C00009.png) 1900-01-01
FR1341351A (fr) 1963-10-25
DE1218655B (de) 1966-06-08
DK114993B (da) 1969-08-25
NL286762A (US06338842-20020115-C00009.png) 1900-01-01
GB1006582A (en) 1965-10-06

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