US3399027A - Dyeing nickel chelate modified polyolefin with azomethine dyes - Google Patents

Dyeing nickel chelate modified polyolefin with azomethine dyes Download PDF

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US3399027A
US3399027A US302465A US30246563A US3399027A US 3399027 A US3399027 A US 3399027A US 302465 A US302465 A US 302465A US 30246563 A US30246563 A US 30246563A US 3399027 A US3399027 A US 3399027A
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nickel
parts
benzene
group
polyolefine
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US302465A
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Siegrist Gerald
Biedermann Walter
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Novartis AG
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JR Geigy AG
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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
    • D06P3/795—Polyolefins using metallisable or mordant dyes, dyeing premetallised fibres
    • 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
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/04—Azo compounds in general
    • C09B45/12—Azo compounds in general other metal compounds
    • 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
    • C09B55/00—Azomethine 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
    • Y10S8/933—Thermosol dyeing, thermofixation or dry heat fixation or development

Definitions

  • Shaped polyolefines which contain organic nickel chelate complexes as dye acceptors are dyed or printed by contacting shaped articles of such polyolefine material with fine dispersions, either in the form of solution or fine suspensions of certain metallizable azo or azomethine dyestuffs which are capable of taking part in metal complex formation.
  • the present invention concerns a process for the dyeing and printing of shaped goods made from polyolefines and more particularly from polypropylene or polyethylene material, as well as an industrial product, the shaped polyolefine goods colored or printed according to this process.
  • shaped articles of polyolefine material of strong and light-fast shades are obtained by dyeing or printing such articles, the polyolefine of which contains organic nickel chelate complexes as dye acceptors, with fine dispersions, either in the form of solutions or fine suspensions of certain metallizable azo or azomethine dyestuffs defined below which are free from salt-forming, water-solubilizing groups, or containing only such salt-forming groups as defined below, which are capable of taking part in metal complex formation.
  • the resulting dyed and printed polyolefine goods are distinguished particularly by a lightfastness which is due, on the other hand to the good lightfastness properties of the resulting dye component in the colored material and, on the other hand, to the fact that the organic nickel chelate complexes have the double function of acting as dye acceptors and as light stabilizers, the combined effect being an excellent light-fastness of the dyed polyolefine article.
  • organic nickel chelate complexes is used herein to describe polydentate organic chelating agents capable of acting as dye acceptors which preferably contain several oxygen atoms and in certain cases, in addition, sulfur or nitrogen atoms as donor atoms.
  • the starting polyolefine material which is dyed according to the invention contains preferably nickel chelate complexes of the aromatic series, preferably of :alkylated o,o'-dihydroxydiphenyl sulfides, each of the alkyl radicals advantageously containing about 4 to 12 carbon atoms.
  • Polyolefine, which contains the nickel complex of 2,2'-dihydroxy-5,5'-diisooctyldiphenyl sulfide is particularly suitable for the dyeing process according to the inven- 3,399,027 Patented Aug. 27, 1968 tion because remarkable deep dyeings can be attained therewith.
  • Ni-ethylene diamine tetraacetate can be used as second choice only, with less improvement in fastness of the dyeings.
  • the foregoing other chelate complexes are preferred.
  • polypropylene e.g. isotactic polypropylene
  • polyethylene e.g. isotactic polypropylene
  • mixed polymers of these two olefines containing the abovedefined nickel chelates can be dyed or printed according to the invention.
  • these polyolefines advantageously contain other additives such as antioxidants, additional light stabilizers, delustering agents, etc.
  • the polyolefine material can 'be used in any form desired, eg as foils, granulates, and the like disperse dyes, but, preferably, as fibers.
  • the content of nickel is about 0.1 to not more than 2% and preferably 0.1 to 1.2% of the weight of the material to be dyed; lower contents than 0.1% have a disadvantageous effect on the fastness properties of the resulting dyeings or prints.
  • azo and azomethine dyestuffs are suitable for the dyeing and printing of the abovedescribed polyolefine materials in the process according to the invention.
  • Disazo dyestuffs which are derived from the dyestufis defined above under (1), wherein one benzene ring bears, in p-position to the azo bridge or in p-position to a metallizable hydroxy substituent defined above, a benzeneazo or naphthalene-azo substituent.
  • dyestuffs defined above under 1) and (2) either bear no further substituents, or they are further ring-substituted, preferably in a position other than ortho, to the metallizable azo bridge, namely, alkyl with from 1 to preferably not more than 12 carbon atoms, e.g.
  • cycloaliphatic substituents particularly cyclohexyl
  • araliphatic substituents particularly benzyl or phenylethyl
  • aromatic substituents especially phenyl, chlorophenyl, brornophenyl, lower alkyl-phenyl, lower alkoxy-phenyl, nitrophenyl; lower alkoxy, e.g.
  • acylamino substituents especially alkanoylamino, preferably with a total of from 2 to 7 carbon atoms; halogen substituents such as fluorine, chlorine or bromine; carbamyl or sulfamyl groups wherein the nitrogen atom is mono-substituted with alkyl with 1 to 8 carbon atoms, or phenyl, or cyclohexyl, or wherein the nitrogen atom is di-substituted with two alkyl groups or with one alkyl and one phenyl or one alkyl and one alkyl-phenyl radical, the total number of carbon atoms of the two nitrogen substituents being from 2 to 8; sulfonic acid aryl ester radicals, especially phenoxy sulfon
  • Disazo dyestuffs derived from the monoazo dyestuffs described under (3), wherein the benzene ring is substituted in p-position to the azo bridge or in p-position to the metallizable OH substituent with phenylazo or naphthylazo.
  • the benzene or naphthalene nuclei of the dyestuif molecules defined under (3) and (4) are either free from further substituents or contain substituents from the class defined above as permissible ring substituents.
  • Monoazo dyestuffs of the naphthalene-azo-benzene or the naphthalene-azo-naphthalene series wherein one naphthalene nucleus bears, in o-position to the azo bridge, a metallizable COOH group, while the other component, either a benzene or a naphthalene ring, bears in position to the azo bridge a -OH, NH or NHR group, wherein R is either lower alkyl, phenyl, lower alkyl-phenyl, chlorophenyl, bromophenyl or ortho-carboxyphenyl.
  • Monoazo dyestuffs of the naphthalene-azo-pyrazol- -one and the naphthalene-azo-(S-amino-pyrazole) series wherein the naphthalene nucleus bears, in o-position to the azo bridge, a COOH group.
  • the naphthalene, and especially benzene, nuclei of these dyestuffs where the latter are present in l-position at the pyrazole nucleus are either unsubstituted or substituted with ring substituents of the class defined above; the pyrazole nuclei are substituted in 1- and 3-position as defined under (3).
  • Azomethine dyestuffs of the benzene-azomethinebenzene and the benzene-azo-benzene-naphthalene series wherein the benzene nucleus linked to the nitrogen atom of the azomethine bridge bears, in o-position to said bridge, a --OH or COOH group while the nucleus of the other component bears, in o-position to the bridge, a hydroxy group.
  • the nuclei of these dyestuffs are either free from further substituents or bear further ring-substituents of the class defined above.
  • Azomethine dyestuf is derived from the dyestuffs defined in (7) above, wherein either the benzene ring linked to the nitrogen atom of the azomethine bridge bears, in p-position to said bridge or in p-position to a metallizable OH group, or wherein a benzene nucleus linked to the methine group of the azomethine bridge bears, in pposition to the metallizable hydroxy group, a phenylazo or naphthylazo substituent.
  • the aromatic nuclei of these dyestuffs are either free from further substituents or are further substituted with ring-substituents of the class defined above.
  • the metallizable groups in the o,o'-positions of azo or azomethine compounds are responsible for the metallization of these dyestuffs, e.g. hydroxyl, carboxyl or amino groups.
  • dyestuffs with a different type of metal complexing configuration which contain an o(lower alkyl carbonyl)phenol hydroxycarboxy-hydroxy-phenyl-o-amino-carboxyphenyl grouping such as the o-acetyl-phenol or salicylic acid radical, can also be used.
  • substituents of a hydrophobic character in particular alkyl radicals having 4 to 12 carbon atoms, but also the nitro group and/or halogen substituents, especially chlorine, bromine or fluorine, or trifiuoromethyl, are preferred ring-substituents.
  • azomethine dyestuffs defined above under (7) and (8) are preferred, in which the aromatic nuclei are either unsubstituted or substituted with alkyl having 4 to 12 carbon atoms, nitro, fluorine, chlorine or bromine.
  • Dyeing is performed from a weakly alkaline, neutral or weakly acid, preferably aqueous dyebath wherein the dyestuff is finely dispersed as a solution and/or a fine suspension, preferably at boiling temperature, or at a temperature above C. under corresponding excess pressure.
  • Aqueous dispersions used as the dyebath according to the invention preferably contain as dispersing agents condensation products of formaldehyde and naphthalene sulfonic acids, of unsulfonated or sulfonated amines and higher fatty acids, e.g., of p-anisidine sulfonic acid with coconut oil fatty acid in a molar ratio of 1:1 or polyethylene-glycol ether of fatty alcohols with ethylene oxide in a molar ratio of from 1:10 to 1:20.
  • Contact time between the dyebath and the goods to be dyed is preferably about 30 to minutes.
  • Printing is performed with a printing paste which contains the usual thickeners, e.g. water-soluble salts of alginic acids or crystal gum solution as well as, optionally, other additives usual in textile printing, such as urea.
  • the print is fixed by known methods, e.g. by steaming at higher temperatures, preferably not exceeding about C. in the case of polypropylene and not exceeding 115 C. in the case of polyethylene.
  • the dyeings and prints on polyolefine articles, in particular of polypropylene fibers produced by the process according to the invention, are very strong in color, and they also have good wet and wash fastness including fastness to perspiration, as well as fastuess to light, to rubbing, to sublimation, to migration and to gas fumes.
  • A is a dye acceptor radical selected from the group consisting of alkylated diphenyl sulfide nickel chelate, nickel acetylacetonate, Ni-salt of glycine, 8- hydroxy-quinoline nickel complex, o-dihydroxy-benzene nickel complex, o-hydroxy-benzophenone nickel complex, salicylic aldehyde nickel complex radicals, and
  • B represents the radical of one of the dyestuffs defined above under (1) to (10),
  • All dyestutfs of classes (1) to (10) must be free from -SO H substituents and also from such COOH and the like salt-forming substituents unless the latter are capable of .chelating nickel atoms present in the polyolefine material being dyed.
  • Example 1 250 parts of unstabilized polypropylene powder, 0.25 part of 2,2-dihydroxy-3,3-di-tert. butyl-5,5-di-ethyldiphenylmethane and 3.75 parts of the complex nickel compound from 1 atom of nickel and 2 molecules of 2,2-
  • the fabric is introduced into the warm bath, the temperature is raised to the boil within 30 minutes and the bath is kept at this temperature for minutes. The fabric is then rinsed hot and cold.
  • An orange colored fiber is obtained which is fast in particular to light, washing and rubbing.
  • Example 2 Example 1 is reacted, but 3.75 parts of nickel acetylacetone are used instead of 3.75 parts of the complex nickel compound from 1 atom of nickel and 2 molecules of 2,2-dihydroxy-5,5-di-tert. octyl-diphenyl sulfide; colored fibers are obtained which are also dyed on orange shade with the dyestuff mentioned in Example 1. The dyeings are also fast to light and washing.
  • Example 3 Example 1 is repeated, but instead of the dyestuff used in the same process, 2 parts of a dyestuff preparation from 3 parts of the monoazo dyestutf of the formula and 4 parts of the disodium salt of dinaphthylmethane disulfonic acid are used; a dark violet-colored fiber is obtained which has good fastness, among others, to light. washing and rubbing.
  • Example 4 100 parts of yarn produced according to part (a) of Example 1 treated in a dyebath obtained from 5000 parts of Water, 2.5 parts of ammonium sulfate and 2 parts of a dyestuif preparation produced by milling 3 parts of the dyestuff of the formula dihydroxy-5,5'-di-tert. octyl-diphenyl sulfide are mixed together in a dry state, then homogenized on a set of mixing rollers at 180 for 5 to 10 minutes and finally sheeted into a foil of 0.5 mm. thickness.
  • Strips of 6 x 50 mm. of cuts from this foil and 6 to 8 parts thereof are fed into the cylinder of a melt index tester of the type described in the Tentative Method of Test for Measuring Flow Rates of Thermoplastics by Extrusion Plastometer, ASTM Designation: D1238-57T, issued 1952; revised 1957.
  • the polypropylene is extruded and simultaneously wound onto a perforated drum.
  • the monofilament so obtained is stretched at the ratio of from 1:6 to 1:8 by rewinding over a stretching device operating at room temperature.
  • Example 4 is repeated, but instead of the dyestuif used therein, 2 parts of a dyestuff preparation from 3 parts of the monoazo dyestuff of the formula and 4 parts of the disodium salt of dinaphthalmethane disulfonic acid are used; a bordeaux colored fiber which has good fastness particularly to light, washing and rubbing is obtained.
  • Example 6 A fabric made from the nickel-containing polypropylene fibers produced by the process described in part (a) of Example 1 is dyed with 2 parts of the dyestufr' preparation from 3 parts of the monoazo dyestufl? of the formula and 4 parts of the disodium salt of dinaphthylmethane disulfonic acid, under the conditions and with the other ingredients described in Example 4. An orange colored material which has good fastness especially to light, washing and rubbing is obtained.
  • Example 7 A fabric made from the nickehcontaining polypropylene fibers produced by the process described is dyed with 2 parts of the dyestuff preparation from 3 parts of the disazo dyestutf of the formula and 4 parts of the disodium salt of dinaph thylmethane disulfonic acid, according to the method described in Example 1, all other ingredients and conditions remaining unchanged. A blueish brown colored material is obtained which has good fastness, among others, to light, washing and rubbing.
  • Example 8 COOH The goods are entered at 50, the bath is brought to 110 within 30 minutes, the goods are dyed for 30 minutes at this temperature and then rinsed first hot and then cold. A vivid yellow-colored yarn is obtained which has good fastness especially to light, washing and rubbing.
  • Example 9 Example 8 is repeated, but instead of the dyestuif there mentioned, 2 parts of the dyestufi of the formula H? liIO are used; an orange-colored yarn is obtained which has good fastness to in particular light, washing and rubbing.
  • Example 10 A fabric made from nickel-containing polypropylene fiber produced as described in paragraph (a) of Example 1, is printed with a printing paste of the following composition: 20 g. of the dyestuff preparation from 8.6 parts 'of the monoazo dyestufi of the formula C 0011 H0 C4He and 11.4 parts of the disodium salt of dinaphthylmethane disulfonic acid,
  • Example 12 250 parts of low-pressure polyethylene granulate containing 0.25 parts of tert. butyl-p-cresol and 0.75 part of dilauryl thiodipropionate as stabilizers, are thoroughly mixed in a mixing drum with 3.75 pants of finely pulverized nickel acetylacetonate. The granules are then melted in an extruder and a monofilament is extruded at'a temperature of 180 through a die of 1.0 mm. diameter. The monofilament obtained is stretched on a hot apparatus to six times its length.
  • 100 parts of the fiber produced as described above are treated in a dyebath consisting of 5000 parts of water, 2.5 parts of sodium N-oleyl-N-methyl-amino ethylsulfonate, and 2.5 parts of amomnium sulfate and 2 parts of dyestutf preparation produced by milling 3 parts of the monoazo dyestutf of the formula with 4 parts of the disodium salt of dinaphthyl methane disulfonic acid.
  • the monofilament is entered at 50 into the dyebath, the temperature is raised to within 30 minutes and the bath is kept at this temperature for 60 minutes.
  • a deep grey-colored monofilament is obtained.
  • the dyeing is fast to light, washing and rubbing.
  • a process for coloring shaped goods of a polyolefine We claim: material selected from the group consisting of shapable 1.
  • a process for coloring shaped goods of a polyolefine polyethylene and shapable polypropylene comprising, in material selected from the group consisting of shapable combination: polyethylene and shapable polypropylene, comprising, in a) admixing 'with said polyolefine an organic nickel combination:
  • an organic nickel chelate selected from the group consisting of alkylated 0,0'-dihydroxydiphenyl sulfide nickel chelate, nickel chelate selected from the group consisting of alkyl acetylacetonate, Ni-s-alt of glycine, 8-hydroxy quin'oated 0,0'-dihydroxydiphenyl sulfide nickel chelate, line nickel complex, o dihydroxy-benzene nickel comnickel acetylacetonate, Ni-salt of glycine, 8-hydroxyplex, o-hydroxy'benzophenone nickel complex, saliquinoline nickel complex, o-dihydroxy-benzene nickel cylic aldehyde nickel complex and ethylene diamine complex, o-hydroxybenzophenone nickel complex, tetraacetate in an amount corresponding to from salicylic aldehyde nickel complex and ethylene di about 0.1 to 1.2% by weight of nickel in the resultamine
  • the molar ratio to the nickel chelate present in the polyolefine goods being colored not exceding substantially 1:1.
  • the molar ratio to the nickel chelate present in the polyolefine goods being colored not exceeding substantially 1:1.
  • a process for coloring shaped goods of a polyole 4.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Coloring (AREA)
US302465A 1962-08-20 1963-08-15 Dyeing nickel chelate modified polyolefin with azomethine dyes Expired - Lifetime US3399027A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH993062A CH393253A (de) 1962-08-20 1962-08-20 Verfahren zum Färben und Bedrucken von textilen Gebilden aus nickelhaltigen Polyalkylenen mit metallisierbaren Azo- oder Azomethinfarbstoffen

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US (1) US3399027A (enrdf_load_stackoverflow)
BE (1) BE650012A (enrdf_load_stackoverflow)
CH (1) CH393253A (enrdf_load_stackoverflow)
DE (1) DE1244708B (enrdf_load_stackoverflow)
FR (1) FR1366469A (enrdf_load_stackoverflow)
GB (1) GB980904A (enrdf_load_stackoverflow)
NL (1) NL296819A (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3533723A (en) * 1964-02-20 1970-10-13 Toray Industries Metallized polypropylene dyeing with o - hydroxy-,o' alkylaminonaphthaleneazo naphthalene
US3630656A (en) * 1968-10-19 1971-12-28 Bayer Ag Process for the dyeing and printing of metal-containing polyolefin textile materials
US5405497A (en) * 1990-08-28 1995-04-11 Kamyr, Inc. Method of chemically reacting a liquid with a gas in a vortex

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3148936A (en) * 1963-04-12 1964-09-15 Exxon Research Engineering Co Blending polyolefin with chelating agent to improve dyeability
US3164438A (en) * 1962-03-29 1965-01-05 Hercules Powder Co Ltd Process for dyeing polypropylene fibers with azoic dyes
US3203752A (en) * 1961-12-22 1965-08-31 Ici Ltd Aftertreatment of dyed polypropylene fibers containing a metal compound with metal complexes
US3240552A (en) * 1961-05-15 1966-03-15 Eastman Kodak Co Crystalline polymerized alpha-monoolefinic hydrocarbons containing an organic addition polymer and a metal compound to improve their dyeability

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1235806A (fr) * 1957-01-30 1960-07-08 Eastman Kodak Co Procédé pour améliorer les propriétés tinctoriales d'un hydrocarbure polymère cristallisable et nouveaux produits obtenus

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3240552A (en) * 1961-05-15 1966-03-15 Eastman Kodak Co Crystalline polymerized alpha-monoolefinic hydrocarbons containing an organic addition polymer and a metal compound to improve their dyeability
US3203752A (en) * 1961-12-22 1965-08-31 Ici Ltd Aftertreatment of dyed polypropylene fibers containing a metal compound with metal complexes
US3164438A (en) * 1962-03-29 1965-01-05 Hercules Powder Co Ltd Process for dyeing polypropylene fibers with azoic dyes
US3148936A (en) * 1963-04-12 1964-09-15 Exxon Research Engineering Co Blending polyolefin with chelating agent to improve dyeability

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3533723A (en) * 1964-02-20 1970-10-13 Toray Industries Metallized polypropylene dyeing with o - hydroxy-,o' alkylaminonaphthaleneazo naphthalene
US3630656A (en) * 1968-10-19 1971-12-28 Bayer Ag Process for the dyeing and printing of metal-containing polyolefin textile materials
US5405497A (en) * 1990-08-28 1995-04-11 Kamyr, Inc. Method of chemically reacting a liquid with a gas in a vortex

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Publication number Publication date
DE1244708B (de) 1967-07-20
NL296819A (enrdf_load_stackoverflow)
FR1366469A (fr) 1964-07-10
GB980904A (en) 1965-01-20
BE650012A (enrdf_load_stackoverflow) 1964-11-03
CH993062A4 (enrdf_load_stackoverflow) 1965-02-26
CH393253A (de) 1965-10-30

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