US3383161A - Process for improving dyeability of the fibres and shaped articles of polypropylene - Google Patents

Process for improving dyeability of the fibres and shaped articles of polypropylene Download PDF

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Publication number
US3383161A
US3383161A US383218A US38321864A US3383161A US 3383161 A US3383161 A US 3383161A US 383218 A US383218 A US 383218A US 38321864 A US38321864 A US 38321864A US 3383161 A US3383161 A US 3383161A
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United States
Prior art keywords
polypropylene
acid
fibre
dyed
fibres
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Expired - Lifetime
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US383218A
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English (en)
Inventor
Kimura Hiroshiro
Koshimo Akio
Nara Hirohisa
Fukunaga Shunichi
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Nippon Rayon Co Ltd
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Nippon Rayon Co Ltd
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Publication of US3383161A publication Critical patent/US3383161A/en
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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
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • 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
    • 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
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • 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
    • D06P1/653—Nitrogen-free carboxylic acids or their salts
    • D06P1/6533—Aliphatic, araliphatic or cycloaliphatic

Definitions

  • the present invention relates to a process for improving dyeability of the fibres and the shaped articles of polypropylene. More particularly, this invention relates to a process for improving the dyeability of polypropylene fibres and the shaped articles blended with bisamide compounds of low molecular weight, treated with at least one compound selected from the group consisting of the halides of acetic acid, hydrogen halides and iodine, and then treated with aliphatic amine compounds.
  • the fibers and the shaped articles of polypropylene have good mechanical properties, it is difiicult to. dye them satisfactorily by using conventional dyestuffs and dyeing methods.
  • the fibres and the shaped articles formed of propylene polymer have little afiinity for dyestutfs because of the chemical and structural characteristics.
  • a process for improving dyeability of the fibres and the shaped articles of polypropylene characterized in that polypropylene is blended with bisamide compounds of having high hydrohobicity, treated with at least one compound selected from the group consisting of the halides of acetic acid, hydrogen halides and iodine after spinning and drawing or shaping processes, and then treated with aliphatic amine compounds after washing.
  • the excellent afiinity of the fibres to anionic dyestuffs such as acid dyestufis, direct dyestuffs, chrome dyestuffs, metal complex dyestufis, reactive dye- ICC stuffs, is obtained.
  • the dyed materials have a very deep shade and good fastness.
  • polypropylene fibres and the shaped articles showed little damage in tensile strength.
  • polypropylene fibres and the shaped articles are dyed not only in a deep shade, but also in all tints of colour so that absolute black colour on the dyed materials can be obtained.
  • the bisamide compounds used in the present invention have good compatibility with polypropylene because of high ,hydrohobicity and nonpolarizability of the bisamide compounds, give no trouble in spinning and drawing or shaping processes and can maintain the obtained materials transparent.
  • Bisamide compounds used in the present invention have a good heat stability, good compatibility with polypropylene in melting process and are represented by the following formula:
  • R and R stand for alkyl group
  • R stands for alkylene group
  • X and X stand for -NHCO, -CONH, NHCOO, or COONH groups.
  • Such bisamide compounds as methylene bisamides, ethylene bisamides, propylene bisamides, butylene bisamides, pentamethylene bisamides, hexamethylene bisamides, produced from capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid, cerotic acid, montanic acid or mixture of them, are of value.
  • these bisamide compounds are blended with polypropylene being in the form of powder or pellets in a quantity of from 1 to 25% based upon the weight of polypropylene.
  • the compounds used in the amine treatment are aliphatic amines, and especially ethylene diamine, hexamethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene-pentamine, and ethylene imine give good results.
  • the concentration of the acids and/or iodine, or the amines in these treatments are above 1% based upon the weight of the fibre, and the treatment is carried out for not less than a few seconds and at above room temperature. They depend upon the form of the fibres of the shaped articles. These treatments and rinsing can be carried out in a continuous or a discontinuous process.
  • Example 1 min. at 100 C., then completely rinsed with water, then also immersed in a 50% aqueous diethylene triamine solution at -90" C. for 60 min. and finally completely rinsed with water.
  • treated fibre was dyed in an acid dye bath containing 5% based upon the weight of fibre of an acid dyestulf, such as Supranol Blue BL (Cl. Acid Blue 59 CI. 50315) or Supramine Red B (Cl. Acid Red 6 CI. 14680) at 100 C. for 60 min.
  • an acid dyestulf such as Supranol Blue BL (Cl. Acid Blue 59 CI. 50315) or Supramine Red B (Cl. Acid Red 6 CI. 14680) at 100 C. for 60 min.
  • the dyed materials thus obtained were approximately same deep shade as nylon 6 fibre dyed with the same dyestuffs under the conditions as described above.
  • fibre produced of polypropylene alone was hardly dyed, even if treated with a monochloro acetic acid solution and diethylene triamine solution under the same conditions as described above.
  • Example 2 The fibre produced of polypropylene blended with 3% of methylene bisstearamide and 3% of methylene bispalmitamide was immersed in a 50% aqueous solution of dichloro acetic acid at 100 C. for min., thereafter completely rinsed with water, then also immersed in a aqueous solution of ethylene diamine at 100 C. for 20 min. and finally completely rinsed with water.
  • treated fibre was dyed in an acid dye bath containing 5% based upon the weight of fibre of an acid dyestuff, such as Solway Purple R (C.I. Acid Violet 43 C.I. 60730) at 100 C. for 60 min. Dyed materials have very deep shades.
  • an acid dyestuff such as Solway Purple R (C.I. Acid Violet 43 C.I. 60730) at 100 C. for 60 min. Dyed materials have very deep shades.
  • Example 3 The fibre, produced of crystalline polypropylene blended with 3% of methylene bisamide was melt-spun and drawn as described in Example 1, was treated with a aqueous solution of monochloro acetic acid at 100 C. for 15 min., thereafter completely rinsed with water, then also immersed in a aqueous solution of hexamethylene diamine at 90 C. for 30 min. and finally completely rinsed with water.
  • Example 4 Crystalline polypropylene material having an average molecular Weight of 66,000 was blended with 7% of ethylene bisstearamine, then melt-spun and drawn as described in Example 1. The resulting fibre was immersed in a 20% aqueous solution of hydrogen iodide at 100 C. for 3 min., completely rinsed with water, then also immersed in a 30% aqueous solution of triethylene tetramine at 100 C. for 20 min. and finally completely rinsed with water.
  • treated fibre was dyed in an acid dye bath containing 5% based upon the weight of fibre of an acid dyestufi, such as Anthraquinone Green GNN (C.I. Acid 25 CI. 61570) or a direct dyestuif, such as Japanol Brown M (01. Direct Brown 2 CI. 22311) and Supraxcel Violet 3RL (Cl. Direct Violet 51 CI. 27905) at 100 C. for 60 min. Dyed materials have very deep shades.
  • an acid dyestufi such as Anthraquinone Green GNN (C.I. Acid 25 CI. 61570) or a direct dyestuif, such as Japanol Brown M (01. Direct Brown 2 CI. 22311) and Supraxcel Violet 3RL (Cl. Direct Violet 51 CI. 27905) at 100 C. for 60 min. Dyed materials have very deep shades.
  • an acid dyestufi such as Anthraquinone Green GNN (C.I. Acid 25 CI
  • Example 5 Crystalline polypropylene material was blended with 3% of hexamethylene bisstearamide and then drawn to a length of 5 times the original one after melt-spun at 270 C. The resulted'fibre was then immersed in 3% aqueous solution of iodine dissolved by potassium iodide at 100 C. for 10 min., completely rinsed with water, then also immersed in a 50% aqueous solution of tetraethylene pentamine at 90 C. for 30 min. and finally completely rinsed with water.
  • Example 6 Crystalline polypropylene material having an average molecular weight of 77,000 was blended with 2% of ethylenebisamide prepared from the mixture of 7 parts of stearic acid and 3 parts of palmitic acid. The resulted fibre was immersed in a 50% aqueous solution of monochloro acetic acid at 100 C. for 10 min., completely rinsed with water, then also immersed in a 2% aqueous solution of ethylene imine at C. for 10 min. and finally completely rinsed with water. Thus treated fibre was dyed With the same dyestutf and the same condition as described in Example 1, and the dyed material have a very brilliant and deep shade.
  • Example 7 Crystalline polypropylene material was blended with 7% of methylene bisstearamide and then melt-Spun and drawn as described in Example 1. Thus obtained fibre was immersed in a bath composed of the mixture of 20% of monochloro acetic acid and 2% of iodine dissolved in potassium bromide at 100 C. for 5 min., completely rinsed with water and then immersed in an 30% aqueous solution of diethylene triamine at C. for 5 min. and completely rinsed with water.
  • the fibre thus treated was found to be dyed in a deep shade and in good fastness.
  • the dyeing was carried out in an acid dye bath containing 5% based upon the weight of fibre of an acid dyestutf, such as Supranol Fast Cyanine 5R (C.I. Acid Blue 113 CI. 26360), or a metal complex dyestulf, at C. for 60 min.
  • an acid dyestutf such as Supranol Fast Cyanine 5R (C.I. Acid Blue 113 CI. 26360), or a metal complex dyestulf
  • Example 8 The fibre produced of crystalline polypropylene blended with 7% of methylene bislauramide was melt-spun and drawn as described in Example 1, was immersed in a 60% aqueous solution of monochloro acetic acid at 100 C. for 5 min., thereafter completely rinsed with water, then also immersed in a 50% aqueous solution of diethylene triamine at 100 C. for 5 min. and finally completely rinsed with water.
  • treated fibre was dyed with the same dyestuif and the same condition as described in Example 1, and the dyed material have a very deep shade.
  • Example 9 The fibre produced of crystalline polypropylene blended with 6% of methylene biscerotamide, was melt-spun and drawn as described in Example 1, was immersed in a 50% aqueous solution of monochloro acetic acid at 100 C. for 5 min., thereafter completely rinsed with water, then also immersed in a 50% aqueous solution of ethylenediamine at 100 C. for 30 min. and finally completely rinsed with water.
  • treated fibre was dyed in an acid dye bath containing acid dyestuffs of 0.2% based upon the weight of fibre in the form of mixture at 100 C. for 60 min. Dyed material has very deep pastel colour.
  • Example 10 Crystalline polypropylene material was blended with 3% of ethylene bismyristamide and 4% of methylene bisarachiamide, then melt-spun and drawn. The resulting fibre was immersed in a 50% aqueous solution of hydrogen iodide at 100 C. for 10 min., completely rinsed with water, then also immersed in a 50% aqueous solution of hexamethylenediamine at 95 C. for 30 min. and finally completely rinsed with Water.
  • treated fibre was dyed in an acid dye bath containing 5% based upon the weight of fibre of a metal complex dyestuff, such as Vialon Fast Blue FFG, Vialon Fast Red G (C.I. Acid Red 226) and Vialon Fast Orange R (Cl. Acid Orange 89) at 100 C. for 60 min.
  • a metal complex dyestuff such as Vialon Fast Blue FFG, Vialon Fast Red G (C.I. Acid Red 226) and Vialon Fast Orange R (Cl. Acid Orange 89) at 100 C. for 60 min.
  • a process for improving the dyeability of polypropylene which comprises the steps of blending polypropylene with from 1 to 25 percent by Weight based on the weight of polypropylene of a bisamide having the formula wherein R and R are lower alkyl, R is lower alkylene and X and X are selected from the group consisting of NHCO and CONH; treating said blended polypropylene with an acid selected from the group consisting of monochloroacetic acid; dichloroacetic acid and trichloroacetic acid and then with a low molecular weight alkylene polyamine.
  • said amine is selected from the group consisting of ethylene diamine, heXarnethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine and ethylene imine.
  • the bisamide is selected" from the group consisting of methylene bistearamide, methylene bispalrnitarnide, methylene bisamide, ethylene bistearamide, hexamethylene 'bistearamide and methylene bislauramide.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Artificial Filaments (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US383218A 1963-07-17 1964-07-16 Process for improving dyeability of the fibres and shaped articles of polypropylene Expired - Lifetime US3383161A (en)

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JP3626263 1963-07-17

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US (1) US3383161A (de)
BE (1) BE650673A (de)
CH (1) CH464524A (de)
DE (1) DE1243385B (de)
GB (1) GB1030554A (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070044255A1 (en) * 2005-08-25 2007-03-01 Mohawk Brands, Inc. Increasing receptivity for acid dyes
US20070071972A1 (en) * 2005-09-28 2007-03-29 Mccoy Kay M Textile fibers having soft hand characteristics and methods of making thereof
US20070157395A1 (en) * 2006-01-12 2007-07-12 Gongping Cao Method for preparing insecticidal textiles by a dyeing process of synthetic fibres with pyrethoids
US20150305859A1 (en) * 2014-04-28 2015-10-29 Cook Medical Technologies Llc Selective Fluid Barrier Valve Device and Method of Treatment

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE628687A (de) * 1962-02-22
US2238949A (en) * 1936-02-06 1941-04-22 Process of modifying the electro
US2276951A (en) * 1939-02-25 1942-03-17 Standard Oil Dev Co Chlorinated polyisobutylene and process of making the same
US2805960A (en) * 1952-11-29 1957-09-10 Du Pont Process for treating polyethylene structures and articles resulting therefrom
US2932550A (en) * 1953-10-14 1960-04-12 Chemstrand Corp Acid pretreatment of polyacrylonitrile-type fibers and the treated fibers
US2991264A (en) * 1957-05-01 1961-07-04 Du Pont Method of partially crystallizing an alpha-olefin polymer
US3098697A (en) * 1956-12-12 1963-07-23 Dichloroethane
US3112199A (en) * 1958-01-28 1963-11-26 Montedison Spa Laminates including photographic films comprising modified, superficially adhesive films of crystalline polymeric alpha-olefins, and methods for making such laminates
US3137989A (en) * 1959-02-18 1964-06-23 Montedison Spa Dyeable bulky yarns based on polypropylene
US3165492A (en) * 1959-10-14 1965-01-12 Eastman Kodak Co Solid poly-alpha-mono-olefin containing n, n'-alkylene bis amides
US3195975A (en) * 1961-08-10 1965-07-20 Montedison Spa Tri-methylol propane diallyl ether treatment of polyolefin-polymeric nitrogenous compound mixtures and fibers and product thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE569039A (de) * 1955-03-30

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2238949A (en) * 1936-02-06 1941-04-22 Process of modifying the electro
US2276951A (en) * 1939-02-25 1942-03-17 Standard Oil Dev Co Chlorinated polyisobutylene and process of making the same
US2805960A (en) * 1952-11-29 1957-09-10 Du Pont Process for treating polyethylene structures and articles resulting therefrom
US2932550A (en) * 1953-10-14 1960-04-12 Chemstrand Corp Acid pretreatment of polyacrylonitrile-type fibers and the treated fibers
US3098697A (en) * 1956-12-12 1963-07-23 Dichloroethane
US2991264A (en) * 1957-05-01 1961-07-04 Du Pont Method of partially crystallizing an alpha-olefin polymer
US3112199A (en) * 1958-01-28 1963-11-26 Montedison Spa Laminates including photographic films comprising modified, superficially adhesive films of crystalline polymeric alpha-olefins, and methods for making such laminates
US3137989A (en) * 1959-02-18 1964-06-23 Montedison Spa Dyeable bulky yarns based on polypropylene
US3165492A (en) * 1959-10-14 1965-01-12 Eastman Kodak Co Solid poly-alpha-mono-olefin containing n, n'-alkylene bis amides
US3195975A (en) * 1961-08-10 1965-07-20 Montedison Spa Tri-methylol propane diallyl ether treatment of polyolefin-polymeric nitrogenous compound mixtures and fibers and product thereof
BE628687A (de) * 1962-02-22

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070044255A1 (en) * 2005-08-25 2007-03-01 Mohawk Brands, Inc. Increasing receptivity for acid dyes
US20070071972A1 (en) * 2005-09-28 2007-03-29 Mccoy Kay M Textile fibers having soft hand characteristics and methods of making thereof
US20070157395A1 (en) * 2006-01-12 2007-07-12 Gongping Cao Method for preparing insecticidal textiles by a dyeing process of synthetic fibres with pyrethoids
US20150305859A1 (en) * 2014-04-28 2015-10-29 Cook Medical Technologies Llc Selective Fluid Barrier Valve Device and Method of Treatment
CN105013077A (zh) * 2014-04-28 2015-11-04 库克医学技术有限责任公司 选择性流体阻隔阀装置和治疗方法
US9980813B2 (en) * 2014-04-28 2018-05-29 Cook Medical Technologies Llc Selective fluid barrier valve device and method of treatment

Also Published As

Publication number Publication date
DE1243385B (de) 1967-06-29
CH464524A (de) 1968-10-31
GB1030554A (en) 1966-05-25
BE650673A (de) 1964-11-16

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