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
  • 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
  • D06P1/32—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 oxidation dyes
• • 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
  • Y10S8/904—Mixed anionic and nonionic emulsifiers for dyeing
• • 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
  • Y10S8/922—Polyester fiber
• • 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
  • Y10S8/924—Polyamide fiber
• • 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
  • Y10S8/927—Polyacrylonitrile fiber

Definitions

• the dyed fibers, of dark shade, are of excellent fastness to light, sublimation, washing and dry-cleaning.
• This invention relates to fast dyeing of synthetic fibers, and more particularly fast dyeing of polyester fibers with oxidation dyes.
• an object of the present invention is to dye 3,561,913 Patented Feb. 9, 1971 synthetic fibers, particularly polyester fibers in dark shade, particularly in black shade with a very simple operation.
• Another object of the present invention is to provide dark dyed synthetic fibers with excellent fastness to the light, sublimation, washing and dry-cleaning.
• nucleus A is an aromatic nucleus
• nucleus B is an aromatic nucleus or a quinoid ring
• nucleus C is a quinoid ring
• X is a halogen atom
• nucleus C may further be substituted with at least one halogen atom and/ or nitro radical and/ or alkyl radical.
• R is OH
• compounds of the formula II are mor p-hydroxydiphenyl amines, compounds of the formula II; C 011 such as 4-methyl-4'-hydroxydiphenylamine, 3-methyl-4- hydroxydiphenylamine, 2-methyl 4' hydroxydiphenylamine and 4-methyl-3'-hydroxydiphenylamine, and compounds of the formula such as N-(p-hydroxyphenyl)fi-naphthylamine.
• R is 0 in the Formula I are N-phenyl-p-benzoquinone monoimine and N-(p-diethylaminophenyl)p-benzoquinone monoimine.
• Examples of the compounds represented by the general Formula II are and mixtures of two or more of them.
• N-chlorop-benzoquinone monoimine and N,N'-dichloro-p-benzoquinone diimine are preferable.
• the method of dyeing of the present invention may be carried out by treating synthetic fibers or their products (yarns, threads, fabrics, articles of clothing, etc.) with a compound of the above mentioned general Formula I or N,N'-diphenyl-p-benzoquinone diimine and a compound of the general Formula II in any order or simultaneously.
• These compounds may be employed in the form of an aqueous solution or aqueous dispersion with or without the aid of a dispersing agent or emulsifier.
• the treating liquid may be applied to the synthetic fibers by any suitable method commonly employed in the art of dyeing, such as dipping, pad steaming, thermosol padding, spraying, etc.
• the concentration of the respective compounds in the treating liquids varies depending on the desired thickness of the shade or color. However, for thick colors, the amount of each compound to be deposited on the fibers is in the range of 1 to by weight based on the things to be dyed.
• the proper concentration in the dyeing bath is usually 0.05 to 2.0% by weight in the dipping process, and 2 to 8% by weight in the padding process.
• the temperature and time of the treatment may be varied over a wide range.
• the treatment may be conducted at a temperature from the room temperature (e.g. C.) to 180 C. from 20 seconds to one hour depending upon the mode of dyeing.
• the fibers are treated in a treating bath at a temperature from the room temperature to 140 C., preferably from 60 to 130 C. for about 15 minutes to 1 hour, while in the padding process, the fibers are impregnated with the treating liquid usually at the room temperature, are then squeezed to a liquid content of about 50 to and dried if desired, and then heated with a suitably heating medium such as steam, hot air, infrared rays or hot inert liquid at 100 to 180 C. for about 20 seconds to 10 minutes.
• a suitably heating medium such as steam, hot air, infrared rays or hot inert liquid at 100 to 180 C. for about 20 seconds to 10 minutes.
• synthetic fibers are dipped in a dyeing bath (SO- C.) which contains a compound of general Formula I and which, if desired, may also contain an emulsifier or dispersing agent, until a sufficient amount of the compound of the Formula I is absorbed in the fibers. Then the product is briefly washed, and dried if desired. Then it is dipped in an aqueous dispersion or aqueous solution of a compound of the Formula II at a temperature from the room temperature to C., pref erably 60 to 130 C. The treatment is conducted until the reaction proceeds to a desired extent, and then the dyed fibers are washed in the usual manner.
• a dyeing bath SO- C.
• the synthetic fibers can be dyed in a thick dark shade with excellent fastnesses.
• the method of the present invention is particularly useful in dyeing fibers of polyesters such as polyethylene terephthalate, but it can be generally applied also to other synthetic fibers, filaments, films, fabrics, etc., such polyamides as 6-nylon and 6-6-nylon, polyacrylonitriles, polyvinyl alcohols, polyvinyl chlorides, polyure thanes and cellulose acetate.
• EXAMPLE 1 Two parts of a woven fabric of polyethylene terephthalate-isophthalate (copolymerization ratio of 9:1) fibers were heated at a temperature of 100 C. for 30 minutes in 100 parts of an aqueous dispersion containing 0.1 part of p-hydroxydiphenyl amine, 0.4 part of an anionic surfactant (condensate of sodium naphthalene sulfonate and formaldehyde) and 0.1 part of a nonionic surfactant (addition product of p-alkyl phenol and ethylene oxide).
• an anionic surfactant condensate of sodium naphthalene sulfonate and formaldehyde
• a nonionic surfactant addition product of p-alkyl phenol and ethylene oxide
• the fabric was then washed with water, and then dipped in 100 parts of a separate bath containing 0.1 part of N- chloro-p-benzoquinone monoimine and 0.1 part of the above mentioned nonionic surfactant and treated therein at 100 C. for 30 minutes. Then the treated fabric was soaked at a temperature of 100 C. for 20 minutes with an aqueous solution containing 0.1% by weight of the above mentioned nonionic surfactant and 0.2% by weight of Na CO Then, the fabric was washed with water and dried. The fabric was dyed in a thick black shade with a high abrasion resistance and excellent fastness to light, sublimation, Washing and dry-cleaning.
• EXAMPLE 2 A fabric of polyacrylonitrile fibers and a fabric of 6- nylon fibers were dyed in the same manner as in Example 1. In any case, the fabric was dyed in a thick black shade with excellent fastness as in Example 1.
• EXAMPLE 4 A woven fabric of polyethylene terephthalate-isophthalate (a copolymerization ratio of 9:1) fibers was treated with p-hydroxydiphenylamine under the same conditions as in Example 1. After being Washed with water,
• the fabric was dipped in a bath prepared by kneading 0.1 part of N,N-dichloro-p-benzoquinone diimine, 0.4 part of the anionic surfactant in Example 1 and 0.1 part of the nonionic surfactant in Example 1, and dispersing the kneaded mixture in 100 parts of water, and was treated therein at a temperature of 100 C. for 30 minutes.
• the so treated fabric was then soaped in the same manner as in Example 1 and dried.
• the resulting fabric was dyed in a black shade with excellent fastness.
• EXAMPLE 5 One part of a woven fabric of polyethylene terephthalate-isophthalate (a copolymerization ratio of 9:1) fibers was heated at a temperature of 120 C. for 1 hour with a dispersion prepared by kneading 0.1 part of N,N-diphenyl-p-benzoquinone diimine, 0.4 part of the anionic surfactant in Example 1 and 0.1 part of the nonionic surfactant in Example 1, and dispersing the kneaded mixture in 100 parts of water.
• the fabric was cooled a little, washed with water, and was then dipped at the room temperature in a bath prepared by kneading 0.1 part of N,N'-dichloro-p-benzoquinone diimine, 0.4 part of the anionic surfactant in Example 1 and 0.1 part of the nonionic surfactant in Example 1 and dispersing the kneaded mixture in 100 parts of water.
• the temperature of the bath was gradually elevated to 100 C. and the treatment was further conducted at 100 C. for 30 minutes.
• the dyed fabric was soaped at a temperature of 100 C. for 20 minutes with an aqueous solution of 0.1% by weight of the above mentioned nonionic surfactant, and was rinsed and dried.
• the fabric was dyed in a thick black shade with high abrasion resistance and excellent fastness to light, sublimation, washing and dry-cleaning.
• Example 5 when the procedure of Example 5 was repeated except that 2,6-dichloro-N-chloro-p-benzoquinone monoimine was employed instead of N,N-dichloro-p-benzoquinone diimine of Example 5, the fabric was dyed in a thick brown shade with excellent fastness.
• EXAMPLE 7 One part of a woven fabric of polyethylene terephthalate fibers was treated in the same manner as in Example 5 with N,N-diphenyl-p-benzoquinone diimine and with N,N-dichloro-p-benzoquinone diimine, and was soaped to obtain a fabric dyed in a fast thick black shade.
• EXAMPLE 8 Two parts of polyethylene terephthalate-isophthalate (copolymerization ratio of 85:15) fibers were dipped in a bath prepared by kneading 0.1 part of 4-methyl-4-hydroxydiphenylamine, 0.4 part of the anionic surfactant in Example 1 and 0.1 part of the nonionic surfactant in Example 1, and then dispersing the kneaded mixture in 100 parts of water, and heated therein at a temperature of 100 C. for 30 minutes.
• the fabric was then dipped in 100 parts of a bath containing 0.1 part of N-chloro-p-benzoquinone monoimine and 0.1 part of the nonionic surfactant in Example 1, and treated therein at a temperature of 100 C. for 30 minutes. Then the treated fabric was soaped with an aqueous solution of 0.1% by weight of the nonionic surfactant in Example 1 and was rinsed and dried. Thus a fast thick black fabric was obtained.
• EXAMPLE 10 The procedure of Example 8 was repeated except that 0.1 part of N-(p-hydroxyphenyl)-u-naphthylamine or N- (p-hydroxyphenyl)-/3-naphthylamine was employed instead of 4-methyl-4'-hydroxydiphenylamine. As a result, a fabric dyed in a black shade with excellent fastness was obtained.
• EXAMPLE 11 Two parts of a Woven fabric of polyethylene terephthalate-isophthalate (a copolymerization ratio of 9:1) fibers were treated in a tumbler at a temperature of 120 C. for 30 minutes with an aqueous dispersion prepared by kneading 0.1 part of N-phenyl-p-benzoquinone monoimine, 04 part of the anionic surfactant in Example 1 and 0.1 part of the nonionic surfactant in Example 1, and then dispersing the kneaded mixture in 100 parts of water.
• the fabric was rinsed and dipped in a bath prepared by kneading 0.1 part of N,N-dichloro-p-benzoquinone diimine, 0.4 part of the anionic surfactant in Example 1 and 0.1 part of the nonionic surfactant in Example 1, and dispersing the kneaded mixture in 100 parts of water.
• the bath temperature was gradually elevated and the treatment was further conducted at 100 C. for 30 minutes.
• the treated fabric was soaped, rinsed and dried. There was obtained a fabric dyed in a black shade with excellent fastness.
• EXAMPLE 12 The procedure of Example 11 was repeated except that N-(p-diethylaminophenyl)-p-benzoquinone monoimine or N-(p-diethylaminophenyl) -3-phenyl-p-benzoquinone monoimine was used instead of N-phenyl-p-benzoquinone monoimine. Similarly the fabric was dyed in a black shade with excellent fastness.
• EXAMPLE 13 An acrylonitrile polymer fabric and 6-nylon fabric were dyed in the same manner as in Example 11. In any case the fabric was dyed in a deep brown shade with excellent fastness.
• EXAMPLE 14 One part of a polyethylene terephthalate-isophthalate (a. copolymerization ratio of 9:1) fiber fabric was heated at 120 C. for 30 minutes in a tumbler with 50 parts of an aqueous dispersion containing 0.1 part of N,N-di chloro-p-benzquinone diimine, 0.4 part of the anionic surfactant in Example 1 and 0.1 part of the nonionic surfactant in Example 1. The fabric was then washed with water, was then dipped in 50 parts of an aqueous dispersion containing 0.05 part of p-hydroxydiphenylamine, 0.2 part of the above mentioned anionic surfactant and 0.05 part of the above mentioned nonionic surfactant. The fabric was treated therein at 100 C. for 30 minutes, soaped, water-washed and dried. The fabric was dyed in a black shade with excellent fastness.
• EXAMPLE 15 Two parts of polyethylene terephthalate-isophthalate (a copolymerization ratio of :15) fibers were dipped in a bath of parts of an aqueous dispersion containing 0.1 part of N,N-dichloro-p-benzoquinone diimine, 0.1 part of N-phenyl-p-benzoquinone monoimine, 0.8 part of the anionic surfactant in Example 1 and 0.2 part of the nonionic surfactant in Example 1.
• the bath temperature was elevated gradually to 100 C., and the treatment was conducted at 100 C. for 30 minutes.
• the fabric was then soaped, water-washed and dried in the usual manner. The fabric was dyed in a brown shade with excellent fastness.
• EXAMPLE 17 A polyethylene terephthalate-isophthalate (a copolymerization ratio of 9:1) fiber fabric was dipped at the room temperature in a liquid containing 4% by weight of p-hydroxydiphenylamine, 4% by weight of a dispersing agent, 4 g./l. of a chlorobenzene carrier and 1 g./l. of the nonionic surfactant in Example 1. The fabric was squeezed to a liquid content of 80% and was subjected to steaming at 108 C. for 1 minute. The fabric was then rinsed to remove the p-hydroxydiphenylamine deposited on the surface and was dried.
• the fabric was dipped in a liquid containing 5% by weight N-chloro-p-benzoquinone monoimine and 1.2% by weight of the anionic surfactant in Example 1, was squeezed to a liquid content of 80% and was subjected to steaming at 108 C. for 1 minute.
• the fabric was soaped and dried, there was obtained the fabric dyed in a black shade with excellent fastness.
• EXAMPLE 18 Polyethylene terephthalate-isophthalate (a copolymerization ratio of 9:1) fibers were put into an Ober Meyertype dyeing machine, and were dyed therein at a liquor ratio of 1:7 at 100 C. for 40 minutes with an aqueous liquid containing 6% OWF of p-hydroxydiphenylamine, 6% OWF of the dispersing agent and 1 g./1. of the nonionic surfactant in Example 1. After washed with water, the fibers were treated at a liquor ratio of 1:7 at 95 C.
• polyester fibers are treated with a compound of the Formula I or N,N'-diphenyl-p-benzoquinone diimine and a compound of the Formula II in any order or simultaneously.
• polyester fibers are treated first with a compound of the Formula I or N,N-diphenyl-p-benzoquinone diimine and then with a compound of the Formula II.

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• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Coloring (AREA)

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Cited By (2)

• 1967
  • 1967-11-17 US US683827A patent/US3561913A/en not_active Expired - Lifetime
  • 1967-11-24 DE DE19671619647 patent/DE1619647A1/de active Pending
  • 1967-11-24 CH CH1654767A patent/CH503152A/de not_active IP Right Cessation
  • 1967-11-24 CH CH1654767D patent/CH1654767A4/xx unknown

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