US3151928A - Process for improving the tinctorial characteristics of polyolefin fibres - Google Patents

Process for improving the tinctorial characteristics of polyolefin fibres Download PDF

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Publication number
US3151928A
US3151928A US106169A US10616961A US3151928A US 3151928 A US3151928 A US 3151928A US 106169 A US106169 A US 106169A US 10616961 A US10616961 A US 10616961A US 3151928 A US3151928 A US 3151928A
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United States
Prior art keywords
fibers
fibres
sulfuric acid
improving
solution
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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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US106169A
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English (en)
Inventor
Cappuccio Vittorio
Riboni Ubaldo
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Montedison SpA
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Montedison SpA
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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
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05B—SPRAYING APPARATUS; ATOMISING APPARATUS; NOZZLES
    • B05B1/00—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means
    • B05B1/26—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means with means for mechanically breaking-up or deflecting the jet after discharge, e.g. with fixed deflectors; Breaking-up the discharged liquid or other fluent material by impinging jets
    • 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
    • D01F11/00—Chemical after-treatment of artificial filaments or the like during manufacture
    • D01F11/04—Chemical after-treatment of artificial filaments or the like during manufacture of synthetic polymers
    • D01F11/06—Chemical after-treatment of artificial filaments or the like during manufacture of synthetic polymers of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/46—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of 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
    • 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
    • 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
    • D06P1/67316—Acids
    • 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

Definitions

  • the present invention relates to a process for improving the tinctorial characteristics of fibres obtained from mixtures containing olefin polymers, especially polypropyl ene, and basic nitrogen compounds, such as:
  • the present invention can be utilized advantageously in addition to said process for improving hand, at a sequence stage to be selected as desired.
  • Fibres of polypropylene consisting essentially of isotactic macromolecules are especially suitable for use in the process of the present invention.
  • This object is achieved by a treatment such as by contacting with sulfuric acid.
  • the treatment with sulfuric acid according to the present invention can be carried out with or without before or after the stretching of the fibres and at some sequence stage such as, before or after the treatment with monoor diepoxy compounds.
  • the treatment can be carried out continuously or batchwise, for times varying from 1 second to 60 minutes, at temperature of between 15 and 100 C.
  • Aqueous sulfuric acid solutions having concentrations "Ice varying from 0.01% to 30% by weight, are employed.
  • any sulfuric acidtreatment-products such as excess or residual sulfuric acid or such as reaction products, of the sulfuric acid, are removed, e.g., the fibres are washed with water and/ or alkaline substances (alkaline o-r earth-alkaline hydroxides, carbonates or the like).
  • the heptane residue percent in the polypropylene of the following specific examples is an indication of the presence of isotactic macromolecules (as defined by Natta et al., for example, in US. Patent No. 2,882,263).
  • the polypropylene of the following examples therefore consists essentially of isotactic macromolecules.
  • the polyimine condensate was prepared by dissolving 1160 g. of hexamethylene diamine in 1800 cc. water at room temperature while agitating in a 6 litre glass vessel, by heating the solution to 90 C. and by adding to it 897 g. of dichloroethane and a 50% aqueous sodium hydroxide solution (725 g.). When the addition is completed, the reaction is continued at 90 C. for 3 hours, it is then cooled at 20-25 C., an upper solid layer is removed to which 2000 cc. water are added, the mass is heated to 7080 C. and decanted While the Water is removed by distillation. A solid polyimine condensate is obtained.
  • the polypropylene-polyimine condensate mix is granulated by extrusion in a screw device at C.
  • the granulate is spun under the following conditions:
  • filaments are then stretched under steam with a stretching ratio of 1:64 and then crimped.
  • the crimped roving is passed into a vessel containing a 5% aqueous sulfuric acid solution maintained at 25 C.
  • the speed of the entering roving is regulated so as to allow the filaments a residence time in the sulfuric solution of 5 seconds. From the sulfuric solution the filaments pass into another vessel containing a 10% aqueous sodium bicarbonate solution.
  • Staples thus obtained are dyed to intense colors with acid, metallizable, plastosoluble (disperse) and vat dyes.
  • the fastness of the colors obtained on the fibres subjected to the contact with sulfuric acid according to the present invention is clearly better than that of the colors obtained on corresponding fibres, by otherwise identical dyeing processes not subjected to this contact with sulfuric acid.
  • Example 2 A yarn identical with that of Example 1 is prepared; however, the filaments leaving the spinnerett are not epoxidized.
  • the filaments after being stretched under steam with a stretching ratio of 1:6.4, are wetted with a 5% aqueous ethyleneglycoldiglycidylether solution and then treated in autoclave with steam under vacuum (150 mm. Hg) at 105-11'0" C.
  • filaments are then passed in a vessel containing a 10% aqueous sulfuric acid solution at 25 C.
  • the speed of the entering roving is regulated so as to allow the filaments a residence time in the sulfuric solution of 2 seconds.
  • the fibres From the sulfuric solution the fibres pass into a vessel containing a 10% aqueous sodium bicarbonate solution. They are then cut and dried. Staples thus obtained are dyed intensely with acid, metallizable, plastosoluble and vat dyes.
  • the fastness of the colors obtained on the fibres subjected to the contact with sulfuric acid according to the invention, especially the fastness to washing, is better than that of the colors obtained on correspondingly dyed fibres not subjected to this contact with the sulfuric acid.
  • the mix is granulated at 200-210 C. and the granulate is spun under the following conditions:
  • the staple thus obtained is contacted for 10 minutes at the boiling point with a 5% aqueous sulfuric acid solution with a fibre/ bath ratio of 1 :20.
  • the fibres obtained quickly exhaust the bath and the colors obtained have a fastness, particularly to washing, clearly better than that of the colors obtained on correspondingly dyed fibres not subjected to a treatment with sulfuric acid.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Artificial Filaments (AREA)
  • Coloring (AREA)
US106169A 1960-05-05 1961-04-28 Process for improving the tinctorial characteristics of polyolefin fibres Expired - Lifetime US3151928A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT802060 1960-05-05

Publications (1)

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US3151928A true US3151928A (en) 1964-10-06

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US106169A Expired - Lifetime US3151928A (en) 1960-05-05 1961-04-28 Process for improving the tinctorial characteristics of polyolefin fibres

Country Status (7)

Country Link
US (1) US3151928A (xx)
BE (1) BE603385A (xx)
CH (1) CH375099A (xx)
DE (1) DE1178549B (xx)
ES (1) ES267151A1 (xx)
GB (1) GB904998A (xx)
NL (1) NL263829A (xx)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3223472A (en) * 1960-12-15 1965-12-14 Montedison Spa Process for improving the tinctorial characteristics of fibers obtained from olefin polymers
US3245751A (en) * 1962-05-24 1966-04-12 Montedison Spa Textile fibers having improved dyeability and method of preparing same
US3274312A (en) * 1961-12-21 1966-09-20 Montedison Spa Process for preparing dye-receptive shaped articles
US3281203A (en) * 1961-06-15 1966-10-25 Montedison Spa Modification of the dyeing characteristics of isotactic polyolefin fibers containing basic nitrogen groups through treatment with a diepoxide precursor and an alkaline catalyst
US3314743A (en) * 1963-11-07 1967-04-18 Gagliardi Domenick Donald Processes for treatment of preformed articles of olefin polymers and resulting products
US3331806A (en) * 1961-03-08 1967-07-18 Montedison Spa Dye receptive polyolefin compositions containing oxides and/or hydroxides
US3361843A (en) * 1964-06-15 1968-01-02 Uniroyal Inc Method of dyeing a blend of a polyolefin and a nitrogen containing polymer by using a dyebath containing lewis acids
US3363030A (en) * 1962-05-24 1968-01-09 Montedison Spa Dyeable polyolefin textile fibers containing amine condensates of improved thermal stability
US3399249A (en) * 1966-01-12 1968-08-27 Rexall Drug Chemical Sulfopropylated olefin block copolymers having terminal segments containing amno groups
US3413076A (en) * 1962-01-17 1968-11-26 Nippon Rayon Kk Dyeing nitric acid treated formed polypropylene objects containing fatty acid diamides of alkylene diamines
US3475518A (en) * 1959-05-26 1969-10-28 Montedison Spa Solid polymonoolefin compositions having improved dye receptivity and new basic nitrogen polycondensates employed therein
US3505429A (en) * 1961-04-04 1970-04-07 Jack J Press Preferentially modified stereoregular polyhydrocarbons
US3532778A (en) * 1968-10-23 1970-10-06 Celanese Corp Art of producing shaped,modified,condensation polymers
US3678136A (en) * 1970-06-24 1972-07-18 Hercules Inc Flame retardant polyolefins
US3873646A (en) * 1971-12-01 1975-03-25 Lubrizol Corp Dyeable polypropylene compositions containing polymers of N-aminoalkyl acrylamides

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3150917A (en) * 1962-04-23 1964-09-29 Gagliardi Domenick Donald Treatment of polyolefin articles and resulting products
US4263009A (en) * 1978-01-31 1981-04-21 Milliken Research Corporation Method for improving the dyeing characteristics of textile materials containing polyolefin fibers and products produced thereby

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1285738A (en) * 1916-08-12 1918-11-26 Cilander Ag Process for producing wool-like effects on cotton fabrics.
US1998576A (en) * 1926-01-16 1935-04-23 Heberlein Patent Corp Novel artificial silk effects and process of producing same
GB613817A (en) * 1945-06-07 1948-12-03 James Gordon Napier Drewitt Improvements in the production or treatment of cellulose derivative or synthetic resin materials
US2536893A (en) * 1948-04-22 1951-01-02 Alginate Ind Ltd Production of alkali-resistant alginate materials
US2668134A (en) * 1948-08-31 1954-02-02 Plax Corp Process for treating polyethylene and coated product
DE1006828B (de) * 1954-09-03 1957-04-25 Bataafsche Petroleum Verfahren zur Erhoehung der Anfaerbbarkeit von Textilien aus synthetischen Fasern und Geweben
US2882263A (en) * 1954-12-16 1959-04-14 Montedison Spa Process for the polymerization of certain unsaturated hydrocarbons using iron-based polymerization agents
US2903381A (en) * 1954-09-03 1959-09-08 Shell Dev Treatment of synthetic textiles with a polyepoxide having a plurality of 1,2 epoxy groups
US2937066A (en) * 1955-11-23 1960-05-17 Dow Chemical Co Method for treating polyethylene and treated polyethylene articles thereby obtained
US3013998A (en) * 1956-09-27 1961-12-19 Montedison Spa Dyeable compositions, articles formed therefrom and methods for making said articles
US3107228A (en) * 1956-12-12 1963-10-15 Montecatimi Societa Generale P Polypropylene containing a dye-receptive modifier which comprises polyal-kyleneimine or mixztures thereof with an epoxy resin

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB683218A (en) * 1950-02-23 1952-11-26 Calico Printers Ass Ltd Improvements relating to the processing of linear polyester materials
FR1142065A (fr) * 1956-01-31 1957-09-13 Houilleres Bassin Du Nord Procédé pour l'obtention de produits orientés à propriétés physiques améliorées par traitement superficiel d'oxydation
GB896598A (en) * 1957-06-14 1962-05-16 Montedison Spa Elastomers obtained from alpha-olefin polymers and copolymers and process for their preparation

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1285738A (en) * 1916-08-12 1918-11-26 Cilander Ag Process for producing wool-like effects on cotton fabrics.
US1998576A (en) * 1926-01-16 1935-04-23 Heberlein Patent Corp Novel artificial silk effects and process of producing same
GB613817A (en) * 1945-06-07 1948-12-03 James Gordon Napier Drewitt Improvements in the production or treatment of cellulose derivative or synthetic resin materials
US2536893A (en) * 1948-04-22 1951-01-02 Alginate Ind Ltd Production of alkali-resistant alginate materials
US2668134A (en) * 1948-08-31 1954-02-02 Plax Corp Process for treating polyethylene and coated product
DE1006828B (de) * 1954-09-03 1957-04-25 Bataafsche Petroleum Verfahren zur Erhoehung der Anfaerbbarkeit von Textilien aus synthetischen Fasern und Geweben
US2903381A (en) * 1954-09-03 1959-09-08 Shell Dev Treatment of synthetic textiles with a polyepoxide having a plurality of 1,2 epoxy groups
US2882263A (en) * 1954-12-16 1959-04-14 Montedison Spa Process for the polymerization of certain unsaturated hydrocarbons using iron-based polymerization agents
US2937066A (en) * 1955-11-23 1960-05-17 Dow Chemical Co Method for treating polyethylene and treated polyethylene articles thereby obtained
US3013998A (en) * 1956-09-27 1961-12-19 Montedison Spa Dyeable compositions, articles formed therefrom and methods for making said articles
US3107228A (en) * 1956-12-12 1963-10-15 Montecatimi Societa Generale P Polypropylene containing a dye-receptive modifier which comprises polyal-kyleneimine or mixztures thereof with an epoxy resin

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3475518A (en) * 1959-05-26 1969-10-28 Montedison Spa Solid polymonoolefin compositions having improved dye receptivity and new basic nitrogen polycondensates employed therein
US3223472A (en) * 1960-12-15 1965-12-14 Montedison Spa Process for improving the tinctorial characteristics of fibers obtained from olefin polymers
US3331806A (en) * 1961-03-08 1967-07-18 Montedison Spa Dye receptive polyolefin compositions containing oxides and/or hydroxides
US3505429A (en) * 1961-04-04 1970-04-07 Jack J Press Preferentially modified stereoregular polyhydrocarbons
US3281203A (en) * 1961-06-15 1966-10-25 Montedison Spa Modification of the dyeing characteristics of isotactic polyolefin fibers containing basic nitrogen groups through treatment with a diepoxide precursor and an alkaline catalyst
US3274312A (en) * 1961-12-21 1966-09-20 Montedison Spa Process for preparing dye-receptive shaped articles
US3413076A (en) * 1962-01-17 1968-11-26 Nippon Rayon Kk Dyeing nitric acid treated formed polypropylene objects containing fatty acid diamides of alkylene diamines
US3363030A (en) * 1962-05-24 1968-01-09 Montedison Spa Dyeable polyolefin textile fibers containing amine condensates of improved thermal stability
US3245751A (en) * 1962-05-24 1966-04-12 Montedison Spa Textile fibers having improved dyeability and method of preparing same
US3314743A (en) * 1963-11-07 1967-04-18 Gagliardi Domenick Donald Processes for treatment of preformed articles of olefin polymers and resulting products
US3361843A (en) * 1964-06-15 1968-01-02 Uniroyal Inc Method of dyeing a blend of a polyolefin and a nitrogen containing polymer by using a dyebath containing lewis acids
US3399249A (en) * 1966-01-12 1968-08-27 Rexall Drug Chemical Sulfopropylated olefin block copolymers having terminal segments containing amno groups
US3532778A (en) * 1968-10-23 1970-10-06 Celanese Corp Art of producing shaped,modified,condensation polymers
US3678136A (en) * 1970-06-24 1972-07-18 Hercules Inc Flame retardant polyolefins
US3873646A (en) * 1971-12-01 1975-03-25 Lubrizol Corp Dyeable polypropylene compositions containing polymers of N-aminoalkyl acrylamides

Also Published As

Publication number Publication date
NL263829A (xx)
DE1178549B (de) 1964-09-24
BE603385A (xx)
GB904998A (en) 1962-09-05
CH375099A (de) 1964-02-15
ES267151A1 (es) 1961-11-01

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