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
  • D06P3/791—Polyolefins using acid dyes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
  • C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
  • C08G73/08—Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles
• • 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
• • 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
  • 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
  • D01F6/02—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
• • 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
  • D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
  • D06P1/621—Compounds without 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
  • 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
  • D06P1/647—Nitrogen-containing carboxylic acids or their salts
• • 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
• • 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
  • D06P1/6536—Aromatic
• • 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
• • 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
  • Y10S8/92—Synthetic fiber dyeing
  • Y10S8/928—Polyolefin fiber

Definitions

• This invention relates to processes for improving the dyeability of articles made of polyolefins.
• polyolefin is not improved by these known methods to an extent such as to be suitable for dyeing by all kinds of acid dyes.
• polyolefin articles which are improved to an extent such that their excellent physical properties are not damaged, cannot be dyed well with an efiicient exhaustion of dye in the associated dyebath and, moreover, cannot be dyed to deep or black shades.
• the dyeability of polyolefin articles can be improved remarkably by employing monocyclic aromatic carboxylic acids including benzoic acid, salicyclic acid, gallic acid, cinnamic acid, phthalic acid and their derivatives such as methyl salicylic acid, nitrobenzoic acid, nitrosobenzoic acid, nitrophthalic acid, chlorobenzoic acid, anthranilic acid, dihydroxyphthalic acid, hydroxyphthalic acid and sulfosalicyclic acid.
• monocyclic aromatic carboxylic acids including benzoic acid, salicyclic acid, gallic acid, cinnamic acid, phthalic acid and their derivatives such as methyl salicylic acid, nitrobenzoic acid, nitrosobenzoic acid, nitrophthalic acid, chlorobenzoic acid, anthranilic acid, dihydroxyphthalic acid, hydroxyphthalic acid and sulfosalicyclic acid.
• the temperature employed may, generally speaking, be with in the range of from room temperature up to 150 C.
• the temperature employed may, generally speaking, be with in the range of from room temperature up to 150 C.
• another processing plant e.g., a dyeing factory.
• Polyolefins to be used in this invention are modified by the addition thereto 1 to 20% by weight of a material having a melting point between 100 and 300 C. and having the following general formula:
• R and R are members selected from the group consisting of alkylene, phenylene, cycloalkylene, pyridyl, and naphthyl radicals, the alkylene radical being represented by the formula (CH wherein m is a number between 2 and 10;
• X and X are members selected from the group consisting of hydrogen, alkyl, alkenyl, phenyl, naphthyl, amino, benzalamino, formalamino, acetamino, carbamylamino, pyrrolyl and pyridyl radicals, the alkyl radical having from 1 to 18 carbon atoms and being linear or branched, the alkenyl radical having from 2 to 18 carbon atoms;
• Z and Z are selected from the group consisting of carboxyl and hydrazide radicals; and n is a number greater than one.
• polymer% C-CH The polyolefins having been mixed with the abovedescribed additive material can be as easily shaped or processed as ordinarily polyolefins, without suffering from discoloration or degradation and decrease in processability.
• the present invention provides numerous advantages. Firstly, the present invention enables an efficient dyeing of polyolefin articles and is of value from the viewpoint of economics. Secondly, the invention enables the use of polyolefin which is less modified than with conventional techniques. Thirdly, the invention enables the use of all kinds of commercially available acid dyes, especially acid dyes and disperse dyes for the dyeing of polyolefin articles and further yields durable products which may be dyed in all kinds of shade.
• Meunier Pat. No. 2,628,152 wherein it is recommended to dye modified polyacrylonitrile staple fabric with an acid dye in the presence of benzoic acid or salicylic acid.
• the difierences between said patent and our invention are important.
• Meunier merely discloses a levelling effect by the use of benzoic acid or salicylic acid and is not concerned with improving dyeability of a shaped polyolefinic material which has. added thereto a polytriazole with the use of aromatic carboxylic acids for adsorbability of dyestuffs.
• the 118 Standards, 5th class consists of two tests, a washing test and a rubbing test, and is carried out as follows:
• Example 1 A mixture of 5 parts by Weight sebacic acid dihydrazide and 1 part by weight hydrazine hydrate was subjected to reaction under normal pressure in an atmosphere of nitrogen and the resulting condensation polymer was found on chemical analysis to contain 20% nitrogen. It was identified as poly(octamethylene triazole) (12:5) by infrared absorption spectrum. The melting point of the product was 180 C. It was mixed, in an amount of 5% by weight, with powdered polypropylene resin having an average molecular weight of 200,000, and the resulting mixture was subjected to melt spinning by extrusion at 250 C. to produce yarn comprising rnonofilaments of 6 deniers.
• the yarn was immersed in a solution containing salicylic acid at a concentration of g./l. at 60 C., was left to stand overnight, was washed with water and then dried. Then it was dyed to a brilliant red color with 3% Benzyl Fast Yellow GR (C.I. Acid Yellow 40, 18,950) at a bath ratio of 50 and a temperature of 100 C.
• the dyed material passed the HS, 5th class, in its resistance to abrasion and laundering.
• Example 2 To low pressure polyethylene pellet having an average molecular weight of 150,000, was added 5% by weight poly (tetramethylene N-benzal-aminotriazole) (11:3), obtained by reacting adipic acid dihydrazide-condensation polymer with benzaldehyde. The mixture was passed into a pelletizer at 240 C. to produce pellets which were then melt-spun by means of an extruder at 240 C. to produce yarn comprising monofilaments of 10 deniers. The yarn so produced was dyed to a deep yellow color by using a dyeing bath of 3% Dispersol Fast Yellow G (C.I.
• Disperse Yellow 3, 11,855) containing salicylic acid at a concentration of 20 g./l., at a bath ratio of 50 and a temperature of 100 C.
• the dyed material had good resistance to both abrasion and laundering, high enough to pass the 118 Standards, 5th class.
• Example 3 The same yarn as was used in Example 2 was dyed to a deep blue color with 3% Benzyl Blue RBF (C.I. Acid Blue 15, 42,645) in a 10 g./l. terephthalic acid-containing bath at a bath ratio of 20 and a temperature of 100 C.
• the dyed material passed the 118 Standards, 5th class, in its resistance to abrasion and laundering.
• Example 4 3% by weight poly(phenylene methyltriazole) (11:1), obtained by reacting terephthalic acid dihydrazide-condensed polymer with sodium methylate and methyl iodide, was added to polypropylene resin pellet having an average molecular weight of 100,000 and the resulting mixture was passed through an extruder to produce a mixed pellet. This was then extruded at 240 C. to produce yarn comprising monofilaments of 5 deniers. The yarn was dyed with 3% Coomassie Fast Scarlet B (C.I. Acid Red 111, 23,265) in a 20 g./l. gallic acid-containing dyeing bath (the bath ratio was 30 and the temperature 100 C.). The dyed material passed the HS Standards, 5th class, in its resistance to abrasion and laundering.
• Coomassie Fast Scarlet B C.I. Acid Red 111, 23,265
• Example 8 To polypropylene resin powder having an average molecular weight of 100,000, was added 3% by weight poly (phenylene acetaminotriazole) (11:1). The resulting mixture was extruded and spun to produce yarn of 10 denier monofilament. The yarn was treated in a bath containing benzoic acid at a concentration of 20 g./l., at 100 C. for one hour, and was then dyed to a beautiful red color with Rose Bengale (C.I. Acid Red 94, 45,440) at a bath ratio of 50 and at a temperature of 100 C.
• benzoic acid at a concentration of 20 g./l., at 100 C. for one hour
• Rose Bengale C.I. Acid Red 94, 45,440
• Example 15 To low pressure polyethylene resin having an average molecular weight of 150,000 was added 5% by weight a copolymer of poly(octamethylene-4-stearyltriazole) and poly(octamethylene-4-amino triazole) (11:7), obtained by reacting seb-acic acid dihydrazide condensation polymer with stearylamine and 80% hydrazine hydrate, and further treating the result polymer with lauric acid hydrazide. The resulting mixture was subjected to melting spinning to produce yarn comprising multifilaments of 90 deniers/ 15 filaments. The yarn was dyed to a deep purple color with 3% Benzyl Violet 3B (C.I. Acid Violet 17,
• the dyed material passed the I IS Standards, 5th class, in its resistance to abrasion and laundering.
• Example 17 To low pressure polyethylene pellet having an average molecular weight of 150,000 was added 5% by weight poly(octamethylene 4 oleyl triazole-octamethylene 4- aminotriazole) (11:8), obtained by reacting a sebacic acid dihydrazide condensation polymer with oleylamine and hydrazine hydrate and further treating the resultant polymer with acetamide. The resulting mixture was subjected to melt spinning to produce yarn of 10 denier monofilaments. The yarn was treated with a solution of 10 g./l. benzoic acid at 100 C. for one hour and was then dyed to a beautiful red color with 3% Rose Bengale DY (C.I. Acid Red 94, 45,440) at a bath ratio of 30 for one hour. The fastness was found to be JIS Standards, 5th class.
• the degree of condensation n is determined by the osmotic pressure method with the use of a benzyl-alcohol (for a low molecular weight polymer) or a m-cresol (for a high molecular weight polymer) solution or by the end group analysis with the use of K10 What is claimed is:
• polyolefin material selected from the group consisting of polyethylene, polypropylene and polybutenes
• improvement comprising improving the dyeability of the polyolefin article by reacting the article with a monocyclic aromatic carboxylic acid which contains one benzene ring, said polyolefins having been modified by the addition thereto 1 to 20% by weight of a material having a melting point between and 300 C.

Landscapes

• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Polymers & Plastics (AREA)
• Medicinal Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Organic Chemistry (AREA)
• General Chemical & Material Sciences (AREA)
• Manufacturing & Machinery (AREA)
• Coloring (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Artificial Filaments (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=12840558

Family Applications (1)

Country Status (4)

Cited By (3)

Families Citing this family (1)

Citations (6)

• 0
  • NL NL270090D patent/NL270090A/xx unknown
  • NL NL124955D patent/NL124955C/xx active
• 1961
  • 1961-09-28 GB GB34981/61A patent/GB951981A/en not_active Expired
  • 1961-10-07 DE DE19611419531 patent/DE1419531A1/de active Pending
• 1964
  • 1964-03-11 US US351211A patent/US3316054A/en not_active Expired - Lifetime

Patent Citations (6)

Also Published As

Similar Documents