US3215487A - Articles having improved tinctorial properties and method of preparing same - Google Patents

Articles having improved tinctorial properties and method of preparing same Download PDF

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Publication number
US3215487A
US3215487A US282514A US28251463A US3215487A US 3215487 A US3215487 A US 3215487A US 282514 A US282514 A US 282514A US 28251463 A US28251463 A US 28251463A US 3215487 A US3215487 A US 3215487A
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United States
Prior art keywords
amines
fibres
chlorohydroxypropyl
dyes
articles
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Expired - Lifetime
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US282514A
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English (en)
Inventor
Cappuccio Vittorio
Corso Calogero
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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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • 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
    • C08L23/12—Polypropene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • 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
    • D06P1/642—Compounds containing nitrogen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions 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
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors

Definitions

  • the present invention relates to the improvement of the tinctorial characetristics of textile fibres, films, tapes, shaped articles and the like, obtained by extrusion of mixtures of polyolefins consisting essentially of isotactic macromolecules and basic substances acting as tinctorial modifiers, with or without other materials such as stabilizers, solid dispersing agents, opacifiers, dyes and the like.
  • the present invention relates to the treatment of fibres and the like with monoand/or bifunctional derivatives obtained by the reaction of epichlorohydrin with long chain aliphatic amines or with aromatic or heterocyclic amines in order to improve dye receptivity, and to obtain a good color fastness and improved hand characteristics in the resulting textile fibres.
  • Textile fibres obtained from mixtures of synthetic polymers and tinctorial modifiers of a basic nature have a good receptivity to dyes, but are disadvantageous in that the basic compounds mixed with the olefin polymer is somewhat water soluble. Moreover, the tinctorial modifier shows a tendency to migrate out from the fibres, thus causing a greasiness in the manufactured articles ultimately obtained.
  • the treatment of the present invention makes it possible to reduce the amount of tinctorial modifiers incorporated in the 'polyolefin, since the treatment with the nitrogen compounds according to the invention makes it possible to introduce into the fibre that amount of nitrogen required to increase the dyeability of the polyolefin with acid dyes.
  • Suitable compounds which can be used according to the present invention include N-mono-glycidyl derivatives and N-di-glycidyl derivatives of n-dodecylamine and of n-octadecylamine, N-monoand di-chlorohydroxypropyl derivatives of n-dodecylamine and octadecylamine, N- glycidylpiperazine, N,N' -diglycidylpiperazine, N-chlorohydroxypropylpiperazine, and N,N'-di(chlorohydroxypropyl)piperazine.
  • N-monoand diglycidyl derivatives of primary C C aliphatic amines and of piperazine as well as the mono-chlorohydroxypropyl and di- (chlorohydroxypropyl) derivatives are applied from solutions or dispersions in water or in an organic solvent or in the anhydrous state.
  • the application of the foregoing compounds can be carried out before or after stretching of the fibres.
  • the duration of the treatment may vary from a few seconds to 3 hours, at a temperature of from about room temperature to C. below the softening point of the base polymer.
  • Textile fibres which are to be subjected to the treatment of the present invention consist essentially of at least of a polyolefin, more particularly polypropylene consisting essentially of isotactic macromolecules and obtained by stereospecific catalysis of propylene, and from about 1 to 25% of a tinctorial modifier.
  • the tinctorial modifiers (basic nitrogen compounds) used for preparing dyeable textile fibres may be amines or imines of the polyalkylenimine type, or may comprise a nitrogen polycondensate of epichlorohydrin, having a specific viscosity, determined at 25 C. in 1% isopropanol solutions, comprised between 0.1 and 0.7.
  • the mixtures, after granulation or simple sintering, are extruded in a melt spinning device using spinnerets having a length/ diameter ratio greater than 1.
  • the granulation and spinning are carried out by operating in the absence of oxygen, and preferably under an inert gas (e.g., nitrogen).
  • an inert gas e.g., nitrogen
  • Spinning of the mixtures can conveniently be carried out in the presence of a small amount of a solid dispersing agent which facilitates the homogeneous dispersion of the basic nitrogen compound in the molten polymer mass.
  • the dispersing agent is desirably one of the following materials: octyl' and/or stearyl alcohols, stearic acid, benzoin, furoin, vinyl stearate, mono-, diand tri-stearic esters of glycerol, monoethanolamine stearate, stearamide, N-diethanol-lauramide, C C aliphatic amines, condensation products of ethylene oxide with amines of phenols, polystearamide, polyacrylic acid, polystyrene, styrene copolymers, terpene polymers, and the like.
  • stabilizers, opacifiers, and organic or inorganic pigments can, if desired, be added to the polyolefin in addition to the foregoing nitrogen compounds.
  • the fibres, after spinning, are subjected to a stretching process, with stretching ratios of from about 1:2 to 1:10, at temperatures of from about to C., in stretching devices heated with hot air or steam or with a similar fluid, or provided with a heating plate.
  • the fibres thus obtained can be subjected to a dimensional stabilization treatment under conditions of free or hindered shrinking from about 80160 C.
  • the fibres obtained by extrusion of the mixtures of the present invention can be monoor plurifilaments and can be used for preparing bulk yarns or bulk staple fibres.
  • the fibres subjected to the treatment with the aforementioned monoand diglyciciyl derivatives and/or monoand di-(chlorohydroxypropyl) derivatives exhibit a remarkable receptivity for acid dyes, metallized dyes, and disperse dyes.
  • Such fibres also exhibit a good afiinity for basic and vat dyes, exhibit superior hand characteristics, and show particularly solid colors.
  • the fibres obtained according to the present invention show an increased stability with respect to light.
  • control dyeing tests Were carried out for 1 hour and half at the boiling point, in baths containing 2.5% of dye by weight of the fibre, with a fibre/bath ratio of 1:40.
  • Dyeing with acid and metallized dyes was carried out in the presence of 3% ammonium acetate (calculated on the fibre weight) and of 1% of a surface-active agent, namely, the condensation product of 620 mols of ethylene oxide with 1 mol of an alkylphenol such as p-tert. octylphenol, nonylphenol and the like.
  • a surface-active agent namely, the condensation product of 620 mols of ethylene oxide with 1 mol of an alkylphenol such as p-tert. octylphenol, nonylphenol and the like.
  • the fibres were rinsed with running water, and the resulting fibres showed intense colors with acid dyes, metallized dyes, and disperse dyes.
  • the process of the present invention can be also used for improving the tinctorial characteristics and color fastness of various other synthetic fibres, such as the fibres obtained from polyamides, polyesters, acrylic polymers and copolymers, vinyl polymers and copolymers, each in admixture with basic nitrogen substances.
  • a yarn is prepared by extruding a mixture of: 9.6 kg. of polypropylene having an intrinsic viscosity [77] of 1.58 (measured in tetrahydronaphthalene at 135 C.), an ash content of 0.012%, and a residue after heptane extraction of 96.2%; 0.4 kg. of a basic nitrogen polycondensate obtained by reacting 1.30 moles of epichlorohydrin with 0.3 mol of octadecylamine and 1 mole of piperazine, and having a specific viscosity [1 of 0.32 (determined in 1% isopropanol solution at 25 C).
  • the mix is spun and then treated With diglycidyloctadecylamine under the operating conditions reported in the table hereinafter.
  • a yarn is prepared by extruding a mixture of: 9.6 kg. of polypropylene having an intrinsic viscosity [7;] of 1.58 (determined in tetraline at 135 C.), an ash content of 0.012% and a residue after heptane extraction of 97.2%; 0.4 kg. of a basic nitrogen polycondensate obtained by reacting of 0.65 mol of epichlorohydrin with 0.3 mol of dodecylamine and 0.35 mol of piperazine, and having a specific viscosity [1 of 0.27 (determined in 1% isopropanol solution at 25 C.
  • the mix is spun and then treated with diglycidyl pipera- Zine under the operative conditions reported in the table.
  • a yarn is prepared by extruding a mixture of: 9.8 kg. of polypropylene having an intrinsic viscoisty [77] of 1.62 (measured in tetraline at 135 C.), an ash content of 0.015%, and a residue after heptane extraction of 95.6%; 0.4 kg. of a basic nitrogen polycondensate obtained by reaction of 1 mole of diglycidylpiperazine with 1 mole of piperazine, and having a specific viscosity [1 of 0.29 (determined in 1% isopropanol solution at C.).
  • the mix is spun and then treated with di(chlorohydroxypropyl)dodecylamine under the operative conditions reported in the table.
  • a yarn is prepared by extruding a mixture of: 9.6 kg. of polypropylene having an intrinsic viscosity [1;] of 1.62 (measured in tetraline at 135 C.), an ash content of 0.015%, and a residue after heptane extraction of 95.6%; 0.4 of a basic nitrogen polycondensate obtained by reacting 1.3 moles of epichlorohydrin with 0.3 mole of octadecylamine and 1 mole of piperazine, and having a specific viscosity [1 of 0.32 (determined in 1% isopropanol solution at 25 C.).
  • the mix is spun and then treated with diglycidylpiperazine under the operative conditions reported in the table.
  • a yarn is prepared by extruding a mixture obtained from 9.6 kg. of polypropylene having an intrinsic viscosity of 1.62 (measured in tetraline at 135 C.), an ash content of 0.015% and a residue after heptane extraction of 95.6%; and 0.4 kg. of poly-Z-vinylpyridine prepared with stereospecific catalysts, and having an intrinsic viscosity [7 of 0.45 (determined in dimethylformarnide at C.).
  • the mix is spun and then treated with diglycidylpiperazine under the operative conditions reported in the table.
  • Alizarine yellow 20 (0.1. mordant yellow 1).
  • W001 red B (0.1. acid red Alizariue red S (0.1. mordant red 3)-- Alizarine blue SE (0.1. acid blue 43)- Acid black JVS (0.1. acid black 1)
  • a process for rendering more dye receptive textile fibres obtained by the extrusion of a mixture of a synthetic polymer with a basic nitrogen substance which functions as a tinctorial modifier comprising treating said fibres with a compound selected from the group consisting of monoglycidyl amines, diglycidyl amines, chlorohydroxypropyl amines and di(chlorohydroxypropyl) amines, said amines being selected from the group consisting of aliphatic, aromatic, and heterocyclic amines.
  • polymer is a poly-alpha olefin consisting essentially of isotactic macromolecules.
  • polyalpha-olefin is polypropylene consisting essentially of isotactic macromolecules.

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  • 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)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Artificial Filaments (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Coloring (AREA)
US282514A 1962-05-24 1963-05-22 Articles having improved tinctorial properties and method of preparing same Expired - Lifetime US3215487A (en)

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IT1033762 1962-05-24

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US (1) US3215487A (en(2012))
AT (1) AT243747B (en(2012))
BE (1) BE632726A (en(2012))
CH (2) CH393252A (en(2012))
DE (1) DE1246659B (en(2012))
ES (1) ES288263A1 (en(2012))
GB (1) GB1009661A (en(2012))
NL (1) NL293146A (en(2012))
SE (1) SE315568B (en(2012))

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3294864A (en) * 1962-10-05 1966-12-27 Exxon Research Engineering Co Polyolefins blended with amineepoxide condensate
US3363030A (en) * 1962-05-24 1968-01-09 Montedison Spa Dyeable polyolefin textile fibers containing amine condensates of improved thermal stability
US3395969A (en) * 1963-12-28 1968-08-06 Asahi Chemical Ind Method for dyeing polyolefin shaped articles
US3652198A (en) * 1968-09-13 1972-03-28 Uniroyal Inc Mixture of filaments capable of being dyed to a multicolor pattern with anionic disperse dyes
US5326391A (en) * 1992-11-18 1994-07-05 Ppg Industries, Inc. Microporous material exhibiting increased whiteness retention

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3039840A (en) * 1960-10-12 1962-06-19 Hercules Powder Co Ltd Process for manufacturing readily dyeable stereo regulated polyolefin articles and methods for dyeing the same
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
US3115478A (en) * 1959-08-03 1963-12-24 Montedison Spa Poly-alpha-olefin compositions having improved dye affinity
US3127234A (en) * 1964-03-31 Method of producing folyolefev shaped

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE579238A (en(2012)) * 1958-05-31

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3127234A (en) * 1964-03-31 Method of producing folyolefev shaped
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
US3115478A (en) * 1959-08-03 1963-12-24 Montedison Spa Poly-alpha-olefin compositions having improved dye affinity
US3039840A (en) * 1960-10-12 1962-06-19 Hercules Powder Co Ltd Process for manufacturing readily dyeable stereo regulated polyolefin articles and methods for dyeing the same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3363030A (en) * 1962-05-24 1968-01-09 Montedison Spa Dyeable polyolefin textile fibers containing amine condensates of improved thermal stability
US3294864A (en) * 1962-10-05 1966-12-27 Exxon Research Engineering Co Polyolefins blended with amineepoxide condensate
US3395969A (en) * 1963-12-28 1968-08-06 Asahi Chemical Ind Method for dyeing polyolefin shaped articles
US3652198A (en) * 1968-09-13 1972-03-28 Uniroyal Inc Mixture of filaments capable of being dyed to a multicolor pattern with anionic disperse dyes
US5326391A (en) * 1992-11-18 1994-07-05 Ppg Industries, Inc. Microporous material exhibiting increased whiteness retention

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Publication number Publication date
CH641163A4 (de) 1964-12-31
NL293146A (en(2012)) 1900-01-01
DE1246659B (de) 1967-08-10
SE315568B (en(2012)) 1969-10-06
AT243747B (de) 1965-11-25
ES288263A1 (es) 1963-12-16
CH393252A (de) 1964-12-31
GB1009661A (en) 1965-11-10
BE632726A (en(2012)) 1900-01-01

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