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
  • D06P1/44—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
  • D06P1/655—Compounds containing ammonium groups
  • D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
• • 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
  • D06P3/70—Material containing nitrile groups
  • D06P3/76—Material containing nitrile groups using basic 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
  • Y10S8/92—Synthetic fiber dyeing
  • Y10S8/927—Polyacrylonitrile fiber

Definitions

• the invention relates to a process for the dyeing of fibre materials produced from polyacrylonitrile or R stands for a C C ,-alkyl, C C ,,alkenyl or an optionally substituted cycloaklyl or aralkyl radical;
• R and R independently of one another stand for C -C -alkyl or C,-C,-hydroxyalkyl radicals or form together with the nitrogen atom a heterocyclicring and
• A means an optionally substituted naphthyl or tetrahydronaphthyl radical.
• R there may be mentioned by way of example: as alkyl radicals, the n-octyl, Z-ethylhexyl, n-decyl, 2,2- dimethyl-octyl, n-dodecyl, 2,2 -dirnethyl-decyl, 2- methyl-undecyl, n-tridecyl, 2-methyl-dodecyl, ntetradecyl, n-hexadecyl and n-octadecyl radicals;
• alkenyl radicals the tetradecenyl, hexadecenyl and octadecenyl radicals
• cycloaklyl radicals the cyclohexyl, methylcyclohexyl, dimethyl-cyclohexyl, decahydronaphthyl and abietyl radicals;
• aralkyl radicals the benzyl, chlorobenzyl, phenylethyl, 9( l)-phenyl-stearyl and naphthyl-(l )methyl radicals.
• C,-C -alkyl and hydroxyalkyl radicals for R and R there may be mentioned, by way of example, the methyl, ethyl, propyl, i-propyl, n-butyl, sec. -butyl, 2- hydroxyethyl, 2-hydroxypropyl-(l 3-hydroxypropyl- (l) and 4-hydr'oxybutyl-(l) radicals.
• Suitable heterocyclic rings which may be formed from R and R are primarily the pyrrolidine, piperidine and morpholine rings.
• the naphthalene or tetrahydronaphthalene radical may be linked in the lor 2-position to the methylene group.
• the naphthalene ring is preferably linked in the l-position, the tetrahydronaphthalene ring preferably in the 2-position.
• Suitable substituents for the naphthalene or tetrahydro-naphthalene radical are, for example, C,C -alkyl radicals such as the methyl, ethyl, i-propyl or tert. -butyl radicals; furthermore, halogen atoms such as the chlorine or bromine atom; or nitro groups.
• Inorganic as well as organic acids are suitable for salt formation with the ammonium bases of the formula (I); preferred acids are the known inorganic acids, such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulphuric acid, nitric acid or perchloric acid; and organic acids, such as the lower aliphatic carboxylic acids, e.g., formic acid, acetic acid; aromatic sulphonic acids, such as benzene-sulphonic acid, toluenesulphonic acid; and the semie'sters of sulphuric acid, such as methyl-sulphuric acid and ethyl'sulphuric acid.
• preferred acids are the known inorganic acids, such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulphuric acid, nitric acid or perchloric acid
• organic acids such as the lower aliphatic carboxylic acids, e.g., formic acid, acetic acid; aromatic
• R R independently of one another, stand for a methyl, ethyl, 2-hydroxyethyl or 2-hydroxypropyl- (1) group.
• Examples of compounds suitable for the process are the following: dimethyl-decyl-[naphthyl-( l )-methyl]-ammonium chloride, dimethyl-decyl-[naphthyl-(2)-methyl]- ammonium bromide, dimethy-l-dodecyl-[naphthyl-( l methyl]-ammonium chloride, dimethyl-tetradecyl- [naphthyl-( 1 )-methyl]-ammonium chloride, dimethylhexadecyl-[naphthyl-( l )methyll-ammonium bromide, dimethyl-octadecyl-[naphthyl l )-methyl]-ammonium chloride, dimethyl-octadecenyl-[naphthyl'( l methyl]-ammonium acetate, diethyl-dodec
• the compounds to be used according to the invention can be prepared in known manner, for example, by reacting halomethylated naphthalenes or tetrahydronaphthalense with the appropriate tertiary amines.
• the reaction may be carried out in the presence of solvents, such as water, alcohols, glycols, formamide, dimethyl formamide, dimethyl sulphoxide or halogenated hydrocarbons, at temperatures from 30 to l50C.
• Suitable cationic dyestuffs are dyestuffs from various classes of compounds, for example, diphenyl-methane, triphenylmethane and rhodamine dyestuffs; azo or anthraquinone dyestuffs containing onium groups; furthermore, thiazine, oxazine, methine and azomethine dyestuffds, such as are described, for example, in Ullrnanns Encyclopadie der technis'chen Chemie, Third Edition 1970, Supplement, page 225.
• Dyeing of the polyacrylonitrile fibre materials can be carried out in the usual way, by introducing the material to be dyed into an aqueous dyebath which has been heated to about 50 60C and contains the cationic dyestuff, compounds of the formula (I), added salts, such as sodium acetate or sodium sulphate, and acids, such as acetic acid or formic acid; subsequently raising the temperature of the dyebath to approximately 100C in the course of about 30 minutes; and then keeping the dyebath at the same temperature until it is exhausted.
• aqueous dyebath which has been heated to about 50 60C and contains the cationic dyestuff, compounds of the formula (I), added salts, such as sodium acetate or sodium sulphate, and acids, such as acetic acid or formic acid
• fibre materials which consist of polyacrylonitrile or of acrylonitrile-containing copolymers or contain uch polymers or copolymers and which may be present in various stages of processing, for example, as spun cables, combed material, loose material, filaments, yarns, fabrics or knitted fabrics, with outstanding levelness and in deep shades.
• the compounds of the formula (I) Compared with the quaternary ammonium salts commonly used for the dyeing of polyacrylonitrile with cationic dyestuffs, the compounds of the formula (I) have a substantially increased effectiveness which permits of working with substantially smaller amounts of auxiliaries.
• the increased effectiveness is of particular importance for the dyeing of dyestuffs of high affinity i.e., which draw very fast, since in this case the known retarders have to be used in large amounts, in order to obtain level dyeings.
• EXAMPLE l The bath is heated to 98C and kept at the same temperature for 60 minutes. A level blue dyeing is obtained.
• R and R independently of one another stand for a methyl, ethyl, 2-hydroxyethyl or 2-hydroxypropyl- Yarn of polyacrylonitrile fibres is introduced in a li- (1) group. quor ratio of l 40 into a bath which has been heated 3.

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Cited By (3)

Citations (5)

• 1971
  • 1971-09-08 CA CA122,298A patent/CA954255A/en not_active Expired
  • 1971-09-08 JP JP46068992A patent/JPS5247062B1/ja active Pending
  • 1971-09-09 AT AT783571A patent/AT316478B/de active
  • 1971-09-09 IT IT52779/71A patent/IT939395B/it active
  • 1971-09-09 NL NL7112436A patent/NL7112436A/xx unknown
  • 1971-09-10 GB GB4236271A patent/GB1301780A/en not_active Expired
  • 1971-09-10 FR FR7132803A patent/FR2106457B1/fr not_active Expired
  • 1971-09-10 ES ES394965A patent/ES394965A1/es not_active Expired
  • 1971-09-10 CH CH1333271D patent/CH1333271A4/xx unknown
  • 1971-09-10 CH CH1333271A patent/CH541665A/de unknown
  • 1971-09-10 BE BE772477A patent/BE772477A/xx unknown
  • 1971-09-10 US US00179571A patent/US3785768A/en not_active Expired - Lifetime

Patent Citations (5)

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