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
  • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
  • D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
  • C08L23/02—Compositions 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
  • C08L23/02—Compositions 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
  • C08L23/10—Homopolymers or copolymers of propene
• • 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
  • D01F1/00—General methods for the manufacture of artificial filaments or the like
  • D01F1/02—Addition of substances to the spinning solution or to the melt
  • D01F1/10—Other agents for modifying properties
• • 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
  • D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • D01F6/04—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polyolefins
  • D01F6/06—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polyolefins from polypropylene
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
  • D06M11/73—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with carbon or compounds thereof
  • D06M11/75—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with carbon or compounds thereof with phosgene; with compounds containing both carbon and sulfur, e.g. thiophosgene
• • 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
  • D06P1/00—General 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
  • D06P1/44—General 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
  • D06P1/64—General 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 low-molecular-weight organic compounds without sulfate or sulfonate groups
  • D06P1/651—Compounds without nitrogen
  • D06P1/65106—Oxygen-containing compounds
  • D06P1/65143—Compounds containing acid anhydride or acid halide groups
• • 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
  • D06P1/00—General 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
  • D06P1/44—General 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
  • D06P1/673—Inorganic compounds
  • D06P1/67333—Salts or hydroxides
  • D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
  • D06P1/67358—Halides or oxyhalides
• • 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
  • D06P3/79—Polyolefins
• • 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
  • D06P3/79—Polyolefins
  • D06P3/791—Polyolefins using acid dyes
• • 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
  • D06P3/79—Polyolefins
  • D06P3/792—Polyolefins using basic dyes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L2203/00—Applications
  • C08L2203/12—Applications used for fibers
• • 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
  • Y10S8/09—Polyolefin

Definitions

• the present invention relates to the preparation of dyed polyolefin fibres and, more particularly, to a process for improving the tinctorial characteristics of such fibres.
• the chief object of the present invention is the treatment of polyolefin fibres to render them easily dyed with acid or basic dyes. Additional objects will become apparent hereinafter.
• the treatment with phosgene may be carried out directly on the polyolefin fibre, either in gaseous medium in liquefied phosgene, or in suspension in another liquid.
• the liquid may be organic, e.g. cyclohexane, or inorganic, e.'g., sulfuric acid.
• the liquid used should not dissolve the fibre polymer.
• the fibre may be employed in the form of staple, yarn or fabric.
• the treatment with phosgene does not alter the physical characteristics of the fibres, but does cause a structure modification resulting in a certain variation of the infrared spectrum.
• the fibres thus treated acquire high dyability with basic and microsetyl dyes.
• the polyolefin fibres treated with phosgene may be subjected to an amination treatment in order to increase the afiinity to acid dyes.
• the conditions of the phosgenation treahnent may be very mild provided that initially hydroperoxy groups have been introduced, into the polyolefin fibre, e.g., as by treatment of the fibre in an oven at 76-80 C.
• the polyolefin before extrusion the polyolefin is mixed with a polyhydroxyl compound or with a compound capable of becoming such during the extrusion operation.
• the mix is then extruded and the fibres are treated with carbonyl chloride. Subsequent treatment with amines imparts to the fibres high dyability with acid dyes.
• the polyhydroxyl compound should have the following characteristics: be dispersible in the polyolefin in the molten state; have a sufliciently high melting point, i.e., not much higher than the melting point of the polyolefin yet higher than the extrusion temperature; have thermal stability and low vapor pressure at the extrusion temperature.
• Suitable polyhydroxyl compounds include aliphatic or States Patent i was Patented Jan. 1%64 aromatic epoxy resins or phenol-formaldehyde condensation resins of the novolac type.
• the epoxy resins are preferably of low molecular weight. Hydroxyl groups are formed by the opening of the epoxy ring,
• Epoxy resins are well known in the art and are described in the book Epoxy Resins, by Irving Skeist (Reinhold Publishing Co., 1958), and also in Modern Plastics Encyclopedia, issue for 1960, at pages 899*3 (Modern Plastics, Inc., New York, September 1959).
• phenol-formaldehyde resins of the novolac type are also well known. They may be characterized by the following formula:
• n is an integer from about 2 to 10.
• the polyhydroxyl compound reacts with the carbonyl chloride (phosgene) as shown by the following equation:
• R is the residue of the polyhydroxyl compound, which residue also contains hydroxy groups.
• the ROCOCI compound thus obtained then reacts with an amine, either in the presence or absence of water.
• the amination may be carried out with compounds containing amine or imine groups.
• Suitable amines include ethylenediamine, trimethylene diamine, diethylene triamine, tetraethylene pentamine, hexamethylene diamine, etc.
• Suitable irnines include alkylene imines such as ethylene imine, etc.
• the reaction with phosgene can be effected directly on the polyhydroxyl compound, before mixing it with the polyolefin.
• the phosgenation is carried out before extruding the polyolefin-polyhydroxyl compound mix.
• reaction of carbonyl chloride with the fibre and the amination may be carried out either before or after stretching the fibre.
• the amination of the phosgenated fibres is preferably carried out by treating the fibres with boiling aqueous solutions of amines for a time that may vary from a few seconds to two or three hours, depending on the reactivity of the amine used.
• the polyhydroxyl compounds (or the reaction products thereof with carbonyl chloride) are added to the polyolefin, before spinning, in the ratio of between about 1 to 20% by weight of the mix.
• the reaction of carbonyl chloride with the fibre takes place by exposure of the fibre for about 15 to minutes to a stream of COCI
• this may be carried out in homogeneous phase (e.g., solution in organic solvents) or in heterogeneous phase by passing for 30 to minutes a stream of COCl through the solution.
• the dyes suitable for dyeing the fibres according to this feature of the invention are acid, basic or acetate dyes.
• Example 1 10 g. polypropylene staple are immersed in 200 ml. of cyclohexane in a tube provided with a porous diaphragm. Phosgene is passed through at 25 C. for 10 hours. After treatment with air, the fibre is removed from the solvent. It is then washed, first with water acidified with hydrochloric acid, and then with tap water. The fibre is then dried. The fibre is dyed with Brilliant Green (Color Index No. 42,040), thereby obtaining a green color presenting good fastness.
• Brilliant Green Color Index No. 42,040
• Example 3 10 g. polypropylene fabric are treated as described in Example 1, except that the flask is maintained at 25 C. for 18 hours. The fabric is washed with a 0.12% sodium hydroxide solution and then with water. The fabric is dyed with Astrazon Orange G (Color Index 48,035), thereby obtaining a color presenting good general fastness.
• Astrazon Orange G Color Index 48,035
• Example 4 A polypropylene yarn is passed continuously in liquid phosgene at C. with a residence time of about half an hour. The yarn is freed of residual gas by washing, first with dilute aqueous ammonia and then with tap water.
• Example 5 g. polypropylene fabric are treated with stirring, in
• Example 6 A mix of 95 kg. polypropylene (having an intrinsic viscosity of 1.09 determined in tetrahydronaphthalene at 135 C., a residue after heptane extraction of 86.2%, and an ash content of 0.028%) and 5 kg. epoxy resin, obtained from the condensation of epichlorohydrin with bisphenol-A is prepared at room temperature in Werner type mixer. The mix is spun under the following conditions:
• the fibres When dyed with acid dyes, the fibres give colors with good intensity and fastness.
• Dispersed acetate dyes such as Setyl Yellow 56, Setacyl Yellow 36, Acetoquinone Scarlet N, Cibacet Scarlet ER, Acetoquinone Blue RHO.
• Example 7 A mix of kg. polypropylene (having an intrinsic viscosity of 1.28, a residue after heptane extraction of 84.2%, and an ash content of 0.02%) and 10 kg. epoxy resin, obtained from the condensation of epichlorohydrin with bis-phenol-A, is prepared at room temperature in a Werner type mixer. This mix is spun under the following conditions:
• the fibres obtained can be worked, e.g., as described in Italian Patent 579,116, so as to obtain a bulky yarn.
• the yarn skeins (so worked or not) are phosgenated at room temperature for 30 minutes as in the preceding example. They are then washed with Water and then immersed for 30 minutes in a boiling aqueous ethylene diamine solution (80%).
• the fibers thus obtained are dyed with the following acid dyes for wool:
• Example 8 An epoxy resin, obtained from the condensation of epichilorohydrin with ethylene glycol and having an average molecular weight of 300, is dissolved in tetrahydrofurane (30% solution). C081; is bubbled through this solution for 15 minutes. The solvent is evaporated and the phosgenated epoxy resin is mixed with polypropylene (having an intrinsic viscosity of 1.23, a residue after heptane extraction of 85.6% and an ash content of 0.20%) in the proportion of 10% of the mix. g. of this mix are spun in a melt spinning device at an extrusion temperature of about 200 C. under a pressure of 3 kg./'cm. The fibres obtained are treated with amine as describe in Example 7. The fibres give intense and solid dyes with the following dyes:
• Example 10 A mix (100 g.) is prepared consisting of 90% polypropylene (having an intrinsic viscosity of 1.28, a residue after heptane extraction of 94.2%, and an ash content of 0.02%) and 10 g. epoxy resin obtained from the condensation of epichlorohydrin and hydroquinone and having an average molecular weight of 800. This mix is spun in a melt spinning device at an extrusion temperature of about 230 C. under a pressure of 4.5 l g./cm The fibres obtained are treated with phosgene and then with amine as described in Example 7. They are then stretched and dyed with the following dyes, thereby obtaining intense and solid colors:
• Example 11 10 g. polypropylene staple are treated with phosgene as in Example 5. After removal of the acid, the staple is washed with cold water until it is neutral and is then maintained at about C. for about 6 hours in a aqueous monoethylamine solution. The fibre, after thorough washing with water, is dyed with Brilliant Green (Colour Index No. 42,040) thus obtaining an intense dark green color.
• Brilliant Green Cold Index No. 42,040
• Example 12 10 g. polyethylene yarn are treated with phosgene for 6 hours at 20 C. in 500 g. 98% sulfuric acid. It is then washed with cold water until it is neutral, and is treated with a 30% monoethyl-amine solution at about 20 C. for about 6 hours. After washing, the yarn is dyed with the following dyes, thereby obtaining very intense colors:
• a process for preparing fibres from polypropylene containing isotactic macromolecules, which fibres are particularly receptive to dyes, comprising treating said fibres with phosgene.
• a process for preparing fibres from polypropylene containing isotactic macromolecules, which fibres are particularly receptive to dyes comprising treating with phosgene a polyhydroxyl compound selected from a group consisting of the condensation product of epichlorohydrin with a phenol, the condensation product of epichlorohydrin with a polyhydric alcohol, and the novolac condensation product of formaldehyde with a phenol, mixing the thus treated polyhydroxyl compound with the polypropylene, and extruding the mixture.

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• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Polymers & Plastics (AREA)
• Medicinal Chemistry (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Inorganic Chemistry (AREA)
• Manufacturing & Machinery (AREA)
• Artificial Filaments (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Coloring (AREA)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

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Cited By (3)

Citations (6)

• 0
  • NZ NZ126064D patent/NZ126064A/xx unknown
  • BE BE589527D patent/BE589527A/xx unknown
• 1959
  • 1959-04-09 IT IT587759A patent/IT611206B/it active
• 1960
  • 1960-04-04 GB GB11821/60A patent/GB881981A/en not_active Expired
  • 1960-04-05 AU AU59119/60A patent/AU5911960A/en not_active Expired
  • 1960-04-05 US US20017A patent/US3116966A/en not_active Expired - Lifetime
  • 1960-04-06 LU LU38489A patent/LU38489A1/fr unknown
  • 1960-04-06 FR FR823564A patent/FR1254106A/fr not_active Expired
  • 1960-04-07 CH CH391360D patent/CH391360A4/de unknown
  • 1960-04-07 DE DEM44916A patent/DE1124917B/de active Pending
  • 1960-04-08 NL NL250319A patent/NL250319A/nl unknown
  • 1960-04-08 ES ES0257225A patent/ES257225A1/es not_active Expired

Patent Citations (6)

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