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Aftertreatment of dyed polypropylene fibers containing a metal compound with metal complexes

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US3203752A
US3203752A US24492362A US3203752A US 3203752 A US3203752 A US 3203752A US 24492362 A US24492362 A US 24492362A US 3203752 A US3203752 A US 3203752A
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copper
metal
zinc
containing
polypropylene
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Mills Walter Percival
O'neill William Alexander
Price Raymond
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS, OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02After-treatment
    • D06P5/04After-treatment with organic compounds
    • D06P5/06After-treatment with organic compounds containing nitrogen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS, OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/005Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using metallisable or mordant dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS, OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/79Polyolefins
    • D06P3/795Polyolefins using metallisable or mordant dyes, dyeing premetallised fibres
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/928Polyolefin fiber

Description

United States Patent 3,203,752 AFTERTREATMENT OF DYED POLYPROPYLENE FIBERS CONTAINING A METAL COMPOUND WITH METAL COMPLEXES Walter Percival Mills, Manchester, William Alexander ONeill, Harrogate, and Raymond Price, Manchester, England, assignors to Imperial Chemical Industries Limited, London, England, a corporation of Great Britain No Drawing. Filed Dec. 17, 1962, Ser. No. 244,923 Claims priority, application Great Britain, Dec. 22, 1961,

,033 5 Claims. (Cl. 8-75) This invention relates to the aftertreatment of dyed fibres and more particularly to a process for aftertreating dyed polyolefine and polyacetal fibres containing metal compounds, in order to improve the tastness of the dyestufi to light.

It is known that polyolefine and polyacetal fibres containing metal compounds may be dyed with metallisable dyestuffs, and that by this means the dyestuif becomes firmly anchored within the fibre.

A process is known for the production of coloured shaped articles of poly-a-olefines, in particular coloured fibres of stereoregular polypropylene, wherein there is incorporated a basic or anionic exchange substance which contains a metal, characterized in that the article is dyed with an acid dyestufi which forms a chelate compound.

A process is also known for the production of coloured shaped articles containing or consisting of polyacetals, wherein there is incorporated a basic or anionic exchange substance which contains a metal, characterised in that the article is dyed with an acid dyestufi which forms a chelate compound.

Among the metals which may be contained in the anionic exchange substances particular mention may be made of zinc, magnesium and calcium since these metals do not discolour or adversely affect the properties of the fibre. Other metals may, however, be contained in the anionic exchange substance.

We have now found that the light fastness of metallisable dyes on polyolefine and polyacetal fibres containing certain metals may be improved by aftertreatment of the dyed fibre with certain chelate compounds of other metals.

According to the invention therefore, we provide a process for improving dyeings of metallisable dyes on polyolefine and polyacetal fibres containing zinc, calcium, magnesium or aluminium compounds which comprises treating said dyeings with a chromium, cobalt, nickel or copper complex of a chelating agent which yields a zinc complex having a stability constant not greater than 12.0.

The term stability constant has the meaning attributed to it in Chemistry of the Metal Chelate Compounds, by Martell and Calvin, published in New York in 1952 by Prentice-Hall, Inc. Methods for the determination of stability constants are described in Chapter 3.

We mention the following chelating agents which yield zinc complexes having stability constants not greater than 12.0. 8-hydroxyquinoline (10.9), acetylacetone (5.6), benzoylacetone (5.6), glycine (5.5), salicylic acid, salicylaldehyde (4.5), salicylaldoxime, o-hydroxyacetophenone oxime, ethylene diamine (5.9) and o-phenanthroline (6.4). The chromium, cobalt, nickel and copper complexes of such chelating agents are of value in the process of the invention.

During the process of the invention metal exchange is believed to occur, resulting in the formation of a dyestutf complex of chromium, cobalt, nickel or copper within the polypropylene fibre. It is surprising that metal ex change can be brought about so readily in a completely non-polar medium such as polypropylene. The remark- 3,203,752 Patented Aug. 31, 1965 ice able increases in light fastuess which we are able to produce are in themselves evidence that a considerable amount of metal exchange takes place.

The chromium, cobalt, nickel and copper complexes of acetylacetone are especially valuable in the process of the invention, being stable under ordinary conditions of storage and in aqueous dispersion, but sufdciently reactive with the dyed fibre to produce rapid and extensive metal exchange under the conditions described above.

The process of our invention may conveniently be carried out by treatment of the dyeing with an aqueous dispersion of the chromium, cobalt, nickel or copper complex (obtained, for example, by milling the complex with an aqueous solution of a dispersing agent such as a sulphonated naphthalene-formaldehyde condensate). Such treatment may readily be carried out at a temperature between 70 C. and 120 C., especially between and 100 C. The process is usually complete after heating for about 1 hour between 80 and 100 C., and the textile material may then be rinsed, treated with soap or detergent in normal manner and dried.

Dyed polyolefine or polyacetal fibres suitable for aftertreatment with metal complexes by the process of the invention may be obtained according to known processes generally described above. It is especially advantageous to use a sequestering agent at some stage of the dyeing operation. Particularly, dyed fibres of stereoregular polypropylene containing the said metal compounds may be used in the process of our invention. The zinc, calcium, magnesium or aluminium compounds contained in such fibres are preferably salts of high molecular weight carboxylic acids e.g. 8 to 18 carbon atoms carboxylic acids such as caprylic, stearic or naphthenic acids. Other metal compounds such as inorganic salts and oxides may be contained in the fibres if desired.

The invention is of great value when it is applied to dyeings of metallisable dyestufis on polyolefine and polyacetal fibres containing compounds of zinc, magnesium or calcium. Such dyeings, especially when obtained from metallisable dyestuffs of the monoazo or anthraquinone series are normally of low fastness to light, and aftertreatment with the metal chelate compound brings about a marked improvement. A very marked improvement in light fastness occurs when the dyestufi' used is a monoazo dyestuff containing metal-reactive (especially hydroxy) groups in positions orthoto the azo group.

The invention is illustrated but not limited by the following examples in which the parts are by weights. The light fastness figures are those obtained by the method adopted by the International Organization for Standardization (1.8.0. Recommendation R 105, Part II). The method of testing is also described in British Standards, under BS 1006.

Example 1 100 parts of a polypropylene textile material containing 95% isotatic polypropylene and 5% Zinc stearate is scoure'd for 30 minutes at C. in a bath containing 0-2 part of sodium oleyl p-anisidide sulphonate and 2 parts of ethylene diamine tetraacetic acid sodium salt per 1000 parts water, and rinsed thoroughly in water.

1.5 parts of 1-(2'-hydroxyphenylazo)-2-naphthol is dispersed in water by gravel milling with 0.3 part of a sulphonated naphthalene formaldehyde condensation product, and added to 4000 parts of water at 50 C. containing 4 parts sulphonated naphthalene-formaldehyde condensation product. The scoured polypropylene textile material is immersed in the liquid thus obtained and the temperature is raised is 100 C. Dyeing is continued for minutes at C. and the textile material is then rinsed in water. The deep red textile material is then after-treated by immersion in 4000 parts of warm water con- 3 taining 2 parts of the copper complex of S-hydroxyquinoline (dispersed by gravel milling with 0.5 parts of sulphonated naphthalene-formaldehyde condensation product and 10 parts of water) and 4 parts of sulphonated naphthalene formaldehyde condensation product. The

the copper complex is omitted the dyeing has a light fastness between 1 and 2.

Example 3 Example 1 is repeated using a polypropylene textile temperature is raised to 85 C. for 1 hour and the textile mateflal containing 95 PQ YP PY and 5% material is rinsed in water and washed for 15 minutes Calclllm OXlde- Th6 dyelng obtalned has a llght fast at 60 c. in a solution of a synthetic detergent and ii ness f If the aftertreatment W1th the pp ll i d i water d d i d plex is omitted the dyelng has a llght fastness of 1.

The dyeing so obtained has a light fastness of 5. If 10 The following tables give further examples, mdlcahng 1n the aftertreatment with the copper complex is omitted, 01urnn5 e shades obtamed polypropyleheteXhle the dyeing has a light fastness of 2. terial contaimng 95% isotactic polypropylene and 5% E l 2 Zinc stearate by dyeing With the dyestuffs listed in column xamp e 2 and aftertreating with an aqueous dispersion of the Example 1 is repeated using a polypropylene textile metal complexes listed in column 4, using the procedures material containing 95% isotactic polypropylene and 5% 0 described in Example 1. The light fastness figures, bemagnesium naphthenate. The dyeing so obtained has a fore and after the treatment with the metal complex are light fastness between 4 and 5. If the aftertreatment with given in columns 3 and 6 respectively.

TABLE I Light Light tast- Example Dyestui'r' fast- Metal complex Shade ness alter ness treatment 1-(quinoline-8-azo)-2-naphthol 2-3 Copper/8-hydroxyquinolinc Rubiue..- 4 1-(2-hydroxyphenylazo)-2-naphtho 2 Copper/acetyl acetone Deep red 5 d0 2 Copper/salicylic acid d 4-5 2 Cobalt/acetyl acetone 5 2 Chromium/S-hydroxyquinoline 4 3 Copper/8-hydroxyquinoline 6 naphth 10 d0 3 Copperlsalicylaldoxime- 6 11 1-(Whfiglqoxy-V-chlorophenylazo)-2- 4 Copper/S-hydroxyquinoline -.d0 5-6 nap o. 12.- do 4 Copper/o-hydroxyacetophenone do 5-6 oxime.

TABLE II Ex- Light Light fasta p Metal Compound Dyestufi fast- Metal complex Shade ness after. ness treatment Zinc stearate 2:4'-Diohloro-2-hydroxy-5-methylazobenzene 4 Copper/acetyl acetone Yellow. 5

d 1-(4-Methoxypheny1azo)-2-naphthoi 2-3 do Pink-l 4 l-(2'-Carhoxypheny1azo)-2 naphtho1 2-3 Copper/salicyl-aldoxlmc Red. 4 1-(2-l\lethoxyphenylazo)-2-naphtho1 2-3 Copper/o-hydroxyacetophenone Pmk 4 0311119. 17 Calcium stcaratel-(2-hydroxy-5-chlorophenylaz0)-2-11aphth0l 4 Chromium/acetyl acetoneg Bluidsli 5 re 18 Zinc naphthenatc. 1-(2-Hydroxy-5-ch1oropheny1azo)-2naphtho1 4 Copper/ethylene diamine do 5-6 19 Zinc stearate l-Pllenyl-B-ethoxyearbonyl-4-(2'-hyd r0xy- 3-4 Copper/glycine Yellow... 4

phenylazo)-5-pyrazo1one. 20 d0. l-Phenyl-3-ethoxycarbonyl-4-(4'-nitro-2-hy- 2 Copper/bcnzoyl acetone Orange 4 droxyphenylazo)-5-pyrazolone. 21 do 1-(4-ch1orophenyl)-3-methyl-4 (2"-hydroxy- 2 Copper/acetyl acetone Yellow-. 4

pheny1azo)-5-pyrazolone. 22 Zinc naphthenate. 1-Pheny1-3-ethoxycarbonyl)-4-(2-hydroxy- 3-4 Copper/3-dodeeylpentane-2:4- do 4-5 pheny1azo)-5-pyrazo1one. dione. 23- -do 1-Pheny1-3-ethoxycarbonyl)-4-(2-hydroxy- 3-4 Copper/5-dodecy1-5-hydroxyquido 4-6 pheny1azo)-5-pyrazolone. noline. 24. d0 .do 3-4 Copper/S-n-pmpyl-8-l1ydr0xydo 4-5 quinoline. 25. Magnesium 5-(4-Diethylamlnophenylazo)-8-hydroxyqui- 2 Oopper/methylacetone Red 4 naphthenate. noline. 26. Zinc octoate 5-(2-etl1oxy-4-diethylaminophenylazo)-8-hy- 3 Cohalt/3-n-butylpentane 2:4- do 5 droxyquinoline. ione. 27 l -do 5-(4-chlfgro-y-methylphenylazo)-8-hydroxy- 4 Copper/o-phenanthroline Orange- 5-6 quino me. 28.. lvtagmilstifimt 5-(2:4-dichlorophenylazo)-8-hydroxyquinoline 4 Cobalt/benzoylacetone do 5-6 nap ena e.

do 5- 4-methylpheny1azo)-8-hydroxyquino1ine 4 Nickel/acetylaeetone d0 5-6 1-( F-diet]:ylaminophenylazo)-4-hydroxyacridine 2 Copper/aeety1acetone Brown 4 1-(4-pheny1henzeneazo)-4-hydroxyacridi.ne 3 Nickellacetylacetonm do 4-5 7(4-n-butylphenylazo)-2-acety1amino-4-hy- 2-3 do Yellow 5 droxybenzthiazole. 7(4-chlor0phenylazo)-2-acetyla.mino-4-hydroxy- 3 Copper/S-hydroxyquinoline d0i 5 benzthiazole. 7(2':4'-dichl0rophenylazo)-2-acetylamin0-4-hy- 3-4 Copper/acetylacetone do. 5-6

droxybenzthiazole. 3-oximinomethy1-4-hydroxy-4'-methy1azoben- 2 do "do"--- 4 zone. 3-carboxy-4-hydroxy-4-nitroazobenzene 3-4 do "do..." 5 3:4-dihydroxy-4-ethoxyazobcnzene 2-3 do Brown 4 1:2-dihydroxy-Zi-nitroanthraquinone 5-6 Copper/S-hydroxyquinolinc Rigd- 6-7 IOVVII. 1:2-dihydroxyanthraquinone 6 do Maroon 6-7 1:5:8-trihydroxy-2-aminoanthraqujnonc 4-5 Bordeaux- 5-6 1:2-dihydroxy-B-aminoanthraquinone 4-5 do Brown 5-6 42 -i Zinc stearate 5:8-di(4-methylphenylamino)1:2-dihydroxy- 5 d0 Blue 6 anthraquinone. 43 do 3-cyano-1:5-di(o-hydroxyphenyl) formazan 2 Copper/ethylene diamine 4 We claim:

1. A process for improving dyeings of dyestulfs selected from the class consisting of metallisable dyestutfs of the monoazoand anthraquinone series on stereoregular polypropylene fibres containing metal compounds selected from the class consisting of zinc, calcium, magnesium and aluminum salts of eight to eighteen carbon atom carboxylic acids which comprises immersing said dyeings in an aqueous dispersion of a metal complex selected from the class consisting of chromium, cobalt, nickel and copper complexes of chelating agents, which chelating agents yield zinc complexes having stability constants of at least 4.0 and at most 12.0, at a temperature between 70 and 120 C.

2. A process for improving dyeings of monoazo dyestuffs having hydroxy groups in positions ortho to the azo group on stereoregular polypropylene fibres containing a zinc salt of an 8 to 18 carbon atom carboxylic acid which comprises immersing said dyeings in an aqueous dispersion of a copper complex of a chelating agent, which chelating agent yields a zinc complex having a stability constant of at least 4.0 and at most 12.0, at a temperature between 70 and 120 C.

3. A process for improving dyeings of monoazo dyestuffs having hydroxy groups in positions ortho to the azo group on stereoregular polypropylene fibres containing a zinc salt of an 8 to 18 carbon atom carboxylic acid which comprises immersing said dyeings in an aqueous dispersion of a copper complex of acetylacetone at a temperature between 70 and 120 C.

4. A process for improving dyeing of dyestulfs selected from the class consisting of metallisable dyestuffs of the monoazoand anthraquinone series on stereoregular polypropylene fibres containing a zinc salt of eight to eighteen carbon atom carboxylic acids with comprises immersing said dyeings in an aqueous dispersion of a metal complex selected from the class consisting of chromium, cobalt, nickel and copper complexes of chelating agents, which chelating agents yield zinc complexes having stability constants of up to about 12.0 at a temperature within the range of about to about C.

5. A process for improving dyeings of dyestuffs selected from the class consisting of metallisable dyestuffs of the monoazoand anthraquinone series on stereoregular polypropylene fibres containing metal compounds selected from the class consisting of zinc, calcium, magnesium and aluminum salts of eight to eighteen carbon atom carboxylic acids which comprises immersing said dyeings in an aqueous dispersion of a metal complex selected from the class consisting of chromium, cobalt, nickel and copper complexes of chelating agent, which chelating agents yield zinc complexes having stability constants of at most 12.0, at a temperature between 70 and 120 C.

References Cited by the Examiner UNITED STATES PATENTS 120,393 10/71 Raraf 829 1,805,467 5/ 3 1 Dreyfus 8--3 1 1,896,381 2/ 33 Weber et a1. 895 1,947,597 2/ 34 Hoelkeskamp 8-95 2,215,196 9/40 Schlack 829 2,945,010 7/ 60 Caldwell et al 8-99 X 2,984,634 5/61 Caldwell et al.

3,008,858 11/61 Blake et al.

NORMAN G. TORCHIN, Primary Examiner.

ABRAHAM H. WINKELSTEIN, Examiner.

Claims (1)

1. A PROCESS FOR IMPROVING DYEINGS OF DYESTUFFS SELECTED FROM THE CLASS CONSISTING OF METALLISABLE DYESTUFFS OF THE MONOAZO- AND ANTHRAQUIONE SERIES ON STEREOREGULAR POLYPROPYLENE FIBRES CONTAINING METAL COMPOUNDS SELECTED FROM THE CLASS CONSISTING OF ZINC, CALCIUM, MAGNESIUM AND ALUMINUM SALTS OF EIGHT TO EIGHTEEN CARBON ATOM CARBOXYLIC ACIDS WHICH COMPRISES IMMERSING SAID DYEINGS IN AN AQUEOUS DISPERSION OF A METAL COMPLEX SELECTED FROM THE CLASS CONSISTING OF CHROMIUM, COBALT, NICKEL AND COPPER COMPLEXES AND CHELATING AGENTS, WHICH CHELATING AGENTS YIELD ZINC COMPLEXES HAVING STABILITY CONSTANTS OF AT LEAST 4.0 AND AT MOST 12.0, AT A TEMPERATURE BETWEEN 70* AND 120*C.
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Cited By (12)

* Cited by examiner, † Cited by third party
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US3317272A (en) * 1963-01-11 1967-05-02 Bayer Ag Process for the dyeing and printing of polypropylene fibers
US3340919A (en) * 1965-12-15 1967-09-12 Johnson & Johnson Bag
US3365264A (en) * 1963-02-12 1968-01-23 Allied Chem Dyeing metallized polyolefin with quinoline dyes
US3399027A (en) * 1962-08-20 1968-08-27 Geigy Ag J R Dyeing nickel chelate modified polyolefin with azomethine dyes
US3399952A (en) * 1965-02-26 1968-09-03 Mitsui Kagaku Kogyo Kabushiki Metallized polyolefin dyeing with 1, 4-dihydroxy-or 1, 4, 5, 8-tetrahydroxy-halogenated anthraquinones substituted in the 2-position by phenoxy, alkylmimno, anilino and nu-alkylanilino groups
US3459703A (en) * 1965-10-21 1969-08-05 Ici Ltd Resins stabilized with a nickel,chromium or cobalt chelate
EP0051188A1 (en) * 1980-10-31 1982-05-12 Bayer Ag Process for improving the light fastness of polyamide dyeings
US4544372A (en) * 1982-12-20 1985-10-01 Bayer Aktiengesellschaft Process for improving the light fastness of polyamide dyeings
US4613334A (en) * 1983-07-23 1986-09-23 Basf Aktiengesellschaft Lightfastness of dyeings obtained with acid dyes or metal complex dyes on polyamides
US4655783A (en) * 1985-05-09 1987-04-07 Ciba-Geigy Corporation Process for photochemical stabilization of non-dyed and dyed polyamide fibre material and mixtures thereof
US4655785A (en) * 1984-05-22 1987-04-07 Ciba-Geigy Corporation Process for photochemical stabilization of polyamide and polyurethane fiber materials with metal complex compounds
US4707161A (en) * 1983-07-23 1987-11-17 Basf Aktiengesellschaft Lightfastness of dyeings obtained with acid dyes or metal complex dyes on polyamides: treatment with copper hydroxamates

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NL6401736A (en) * 1963-02-28 1964-08-31
US3341277A (en) * 1963-03-26 1967-09-12 Otto B May Inc Dyeing with a trifluoromethylphenylazo-8-quinolinol and articles so dyed
DE1262210B (en) * 1963-11-02 1968-03-07 Hoechst Ag A method of dyeing, printing and painting of articles made of polyacetal resins
GB1069890A (en) * 1964-02-20 1967-05-24 Toyo Rayon Co Ltd Process for colouring a polyolefinic shaped article containing a metal compound
FR1424072A (en) * 1964-03-05 1966-01-07 Ciba Geigy A process for dyeing and printing contehant polyolefins nickel
GB1070105A (en) * 1964-03-11 1967-05-24 Toyo Rayon Co Ltd Process for colouring a polyolefinic shaped article containing a metal compound
DE1258819B (en) * 1964-07-25 1968-01-18 Hoechst Ag A process for dyeing and printing textile material made of nickel-polypropylene

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3399027A (en) * 1962-08-20 1968-08-27 Geigy Ag J R Dyeing nickel chelate modified polyolefin with azomethine dyes
US3317272A (en) * 1963-01-11 1967-05-02 Bayer Ag Process for the dyeing and printing of polypropylene fibers
US3365264A (en) * 1963-02-12 1968-01-23 Allied Chem Dyeing metallized polyolefin with quinoline dyes
US3399952A (en) * 1965-02-26 1968-09-03 Mitsui Kagaku Kogyo Kabushiki Metallized polyolefin dyeing with 1, 4-dihydroxy-or 1, 4, 5, 8-tetrahydroxy-halogenated anthraquinones substituted in the 2-position by phenoxy, alkylmimno, anilino and nu-alkylanilino groups
US3459703A (en) * 1965-10-21 1969-08-05 Ici Ltd Resins stabilized with a nickel,chromium or cobalt chelate
US3340919A (en) * 1965-12-15 1967-09-12 Johnson & Johnson Bag
US4383835A (en) * 1980-10-31 1983-05-17 Bayer Aktiengesellschaft Process for improving the light fastness of polyamide dyeings with copper complexes of schiff bases or ortho-hydroxy benzophenone
EP0051188A1 (en) * 1980-10-31 1982-05-12 Bayer Ag Process for improving the light fastness of polyamide dyeings
US4544372A (en) * 1982-12-20 1985-10-01 Bayer Aktiengesellschaft Process for improving the light fastness of polyamide dyeings
US4613334A (en) * 1983-07-23 1986-09-23 Basf Aktiengesellschaft Lightfastness of dyeings obtained with acid dyes or metal complex dyes on polyamides
US4707161A (en) * 1983-07-23 1987-11-17 Basf Aktiengesellschaft Lightfastness of dyeings obtained with acid dyes or metal complex dyes on polyamides: treatment with copper hydroxamates
US4655785A (en) * 1984-05-22 1987-04-07 Ciba-Geigy Corporation Process for photochemical stabilization of polyamide and polyurethane fiber materials with metal complex compounds
US4655783A (en) * 1985-05-09 1987-04-07 Ciba-Geigy Corporation Process for photochemical stabilization of non-dyed and dyed polyamide fibre material and mixtures thereof

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NL287100A (en) application
US3186788A (en) 1965-06-01 grant
GB967393A (en) 1964-08-19 application

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