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
  • D06P3/798—Polyolefins using reactive dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
  • C09B62/78—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with other reactive 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
  • D06P3/34—Material containing ester groups
  • D06P3/52—Polyesters
  • D06P3/528—Polyesters using reactive dyes

Definitions

• the present invention relates to a process for fast dyeing of polymeric hydrocarbon, chlorinated polymeric hydrocarbon or polyester fibres or their shaped articles.
• polyester fibres When dyeing polyester fibres, for example, they are usually dyed in a dispersion by high-pressure dyeing, carrier dyeing, or thermosol dyeing, but in these processes, fastness to sublimation is often unsatisfactory depending on the structure of the dyestulf.
• azo dyestuffs having a sulfon azide group in a molecule
• anthraquinone dyestuffs quinoline dyestuffs
• methine dyestuffs diphenylamine dyestuffs
• indigoid dyestuffs indigoid dyestuffs
• nitro dyestuffs there are exemplified azo dyestuffs having a sulfon azide group in a molecule.
• the so-called reactive groups of this patent are also polar groups.
• dyed articles with good fastness is obtained by forming a covalent bond as allowing sulfonyl nitrene (-SOgN) produced by thermal decomposition or photolysis of a sulfon azide group to attack a methyl group (or a methylene or methine group) or a benzene nucleus in fibres possessing a reactive group but no polar group such as polyester fibres and polypropylene fibres, their shaped articles or polyethylene shaped articles.
• sulfonyl nitrene Sulfonyl nitrene
• the process of this invention is substantially dilferent from the process of Japanese patent publication No. 19233/1961 wherein a dyestutf reacts with a reactive polar group in a fibre from the standpoint of the reaction mechanism, and it is an absolutely novel process for dyeing.
• the gist of the present invention is that polymeric hydrocarbon, chlorinated polymeric hydrocarbon or polyester fibres or their shaped articles (for example, film, sheet, etc.) are dyed with a dyestuif having a general formula,
• thermosol dyeing a good result is obtained by a usually employed process, and it is no need to repeat heat treatment and other treatment.
• a sulfon azide group attacks a carbon atom in a methyl group (or a methylene or methine group) or a benzene nucleus to react via a sulfonylnitrene intermediate and a nitrogen-carbon bond is accomplished, as described previously.
• the dyed articles thus obtained is further treated with an organic solvent and/or soaped to remove the unreacted dyestuff, and then water-washed and dried.
• the dyed articles thus obtained have excellent fastness, and particularly, fastness to sublimation is so excellent as bleeding on the attached cloth (of polyester) is 4.5-5 class in the test performed at 2.00 C. for 1 minute.
• polyester polypropylene
• polyethylene polyethylene
• polystyrene polyvinyl chloride
• polyvinylidene chloride polyvinylidene chloride
• chlorinated polyethylene there are exemplified polyester, polypropylene, polyethylene, polystyrene, polyvinyl chloride, polyvinylidene chloride, and chlorinated polyethylene.
• the dyestuif having a sulfon azide group used in this invention is manufactured by the following method: a dyestutf is chlorosulfonated by a conventional method to introduce a sulfonyl chloride group, and the obtained chlorosulfonate is allowed to react with sodium azide to form a sulfon azide group.
• hydrozine hydrate or hydrazine to react with said chlorosulfonate to form a sulfon hydrozide group with which sodium nitritereacts to form a sulfon azide group.
• a dyestulf having: a sulfonic acid group (or an intermediate containing a sulfonic acid group for forming such a dyestuff) is converted to sulfon halogenide by a usual method, and sulfon azide group is formed by the above-described method.
• azo dyestufis when using an amino compound having a sulfon halogenide group as a diazo component, after forming a sulfon hydrozide group, a sulfon hydrozide group is converted to azide simultaneously to diazotization of an amine group by treating with nitrite and an acid.
• Example 1 In a dyebath prepared by adding to 4000 parts of water containing 1 part of sodium oleylsulfate a dispersion produced by grinding 1.5 part of a dyestutf represented by the following Formula I 1.5 parts of a condensate of alkylnaphthaline sulfonic acid as a dispersing agent and 0.7 part of sodium polyalkylnaphthaline sulfonate as a wetting agent together with water for a several hours, 100 parts of polyester fibre (for example, Tetron cloth) were immersed and dyed in a pressure container at 130 C. for 60 minutes. After water-washing the dyed fibre, it was treated at 160 C.
• a dyestutf represented by the following Formula I 1.5 parts of a condensate of alkylnaphthaline sulfonic acid as a dispersing agent and 0.7 part of sodium polyalkylnaphthaline sulfonate as a wetting agent together with water for a several hours
• Example 2 was dispersed and high-pressure dyeing, heat treatment and treatment with N,N-dimethylformic amide were performed, as similar in Example 1: thus, there was obtained a fast dyed article, particularly a clear bluish red polyester dyed article having excellent fastness to sublimation.
• Example 3 1.5 parts of a dyestutf represented by the following Formula III:
• Example l was dispersed by the same method as described in Example l: in a dyebath consisting of said dispersion, 5 parts of a commercially available carrier (Carriant 323, manufactured by Toho Kagaku Co.) and 1500 parts of water, 100 parts of Tetron fabric was immersed. The dyebath was heated up to the boiling point within 30 minutes and the temperature was maintained for 60 minutes. The dyed article was water-washed, treated at 160 C. for
• the dyestufi (III) may be prepared by the reaction with hydrazine hydrate at 25 C. after converting to chlorosulfonate, and after converting to sulfonic hydrazide, adding an aqueous solution of sodium nitrite to convert to azide.
• Example 4 1.5 part of a dyestuff represented by the following general Formula IV:
• the used azo dyestuff (IV) was prepared as follows: 14 parts of 4-amino-phenyl-sulfonic hydrazide were dissolved in a solution consisting of 45 parts of concentrated hydrochloric acid and 200 parts of water, and as cooling at temperatures lower than 5 C., a solution consisting of 11 parts of sodium nitrite and parts of water was dripped: reaction was performed for 1 hour at temperatures lower than 10 C. to form diazo and diazide and then added gradually to a solution consisting of 12 parts of N,N-diethyl-m-toluidine and 200 parts of methanol as cooling. Coupling was performed at 10-15 C. and the separated crystal was filtered and dried in vacuum.
• Example 5 1.5 parts of a dyestutf represented by the following general Formula V:
• Example 6 was treated similarly as described in Example 1 to prepare a dyebath, in which 100 parts of polyester film were Example 6 1.5 parts of a dyestuif (VI) represented by the following general Formula VI:
• Example 2 was treated similarly as described in Example 1 to prepare a dyebath, in which 100 parts of polypropylene film were immersed: after keeping them in the dyebath at 100 C. for 90 minutes, they were water-washed. Then, the dye film was exposed to ultraviolet rays by means of a high-pressure mercury lamp for 15 minutes at room temperature. The unreacted dyestuff' was extracted in trichloroethylene at room temperature, and the film was water-washed to obtain yellow dyed polypropylene film.
• the used dyestulf (V) was prepared similarly to the dyestuff (IV), except that 4-amino-3-chlorophenyl-sulfonic hydrazide was used instead of 4-aminophenyl-su1- fonic hydrazide and N,N-dimethylaniline instead of N,N diethyl-m-toluidine.
• Example 7 Using each 1.5 part of the dyestuffs shown by the following Formulae VII-XXVII, polyester fibres were dyed by the same method as described in Example 1, and there could be obtained fast dyed articles having the hue shown in the right side, particularly dyed articles having excellent fastness to sublimation.
• a process for fast dyeing polymeric hydrocarbon, chlorinated polymeric hydrocarbon or polyester fibers which do not contain a polar group but which do contain at least one of the following: a methyl, methylene, or methine group or a benzene nucleus, or a shaped article made from such fibers comprising: dyeing the fibers or shaped articles with a dyestuff containing a sulfon azide group; exposing the dyestufl molecules attached to the fibers or shaped article to heat, steam or ultra-violet rays to a degree and for a length of time sufficient to decompose the sulfon azide to sulfonyl nitrene, which then forms a covalent bond to the methyl, methylene or methine group, or the benzene nucleus

Landscapes

• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Coloring (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=14080010

Family Applications (1)

Country Status (2)

Cited By (3)

• 1970
  • 1970-11-18 US US90873A patent/US3695821A/en not_active Expired - Lifetime
  • 1970-11-20 GB GB1294989D patent/GB1294989A/en not_active Expired

Also Published As

Similar Documents