EP0051188B1 - Verfahren zur Verbesserung der Lichtechtheit von Polyamidfärbungen - Google Patents
Verfahren zur Verbesserung der Lichtechtheit von Polyamidfärbungen Download PDFInfo
- Publication number
- EP0051188B1 EP0051188B1 EP81108415A EP81108415A EP0051188B1 EP 0051188 B1 EP0051188 B1 EP 0051188B1 EP 81108415 A EP81108415 A EP 81108415A EP 81108415 A EP81108415 A EP 81108415A EP 0051188 B1 EP0051188 B1 EP 0051188B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyamide
- light fastness
- copper
- alkyl
- dyes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/503—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms without bond between a carbon atom and a metal or a boron, silicon, selenium or tellurium atom
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/58—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with nitrogen or compounds thereof, e.g. with nitrides
- D06M11/63—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with nitrogen or compounds thereof, e.g. with nitrides with hydroxylamine or hydrazine
-
- 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
- D06P1/64—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 using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6423—Compounds containing azide or oxime 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
- 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
- D06P1/64—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 using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65112—Compounds containing aldehyde or ketone 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
-
- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
-
- 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
Definitions
- the present invention relates to a method for improving the light fastness of polyamide fibers dyed with acid dyes or metal complex dyes by treatment with copper complex compounds before, during or after the dyeing.
- plastic materials such as. B. polyamide fibers, which may contain any dyes, can be stabilized with metal complexes from Schiff bases.
- metal complexes from Schiff bases.
- chelates of salicylaldehyde derivatives and Sc, Ti, V, Cr, Mn, Co, Cn and especially Ni are used, inter alia, for improving the light fastness of cellulose materials dyed with vat dyes.
- the compounds (II) and (III) are used in amounts of 0.5 ⁇ 4, preferably 1 ⁇ 2%, based on the weight of the polyamide.
- the compounds (1) are obtained in a manner known per se (cf., for example, US Pat. No. 3,361,710) by reacting the corresponding starting compounds with - preferably stoichiometric amounts - a copper salt, in particular a salt of a mineral acid such as copper-II -chloride in preferably alcoholic or aqueous-alcoholic medium.
- Polyamide is understood to mean natural and synthetic polyamide.
- the dyeings can be produced in a conventional manner using both metal complex dyes and acid dyes.
- the known types in particular the 1: 2 chromium or 1: 2 cobalt complexes of mono- or disazo dyes, which are described in large numbers in the literature, are used as metal complex dyes.
- the dyes can in particular also contain 1-2 sulfo groups.
- Suitable acid dyes are commercially available types, which are preferably used in combination with the metal complex dyes.
- the compounds I are of course used in finely divided form, as is obtained by grinding in the presence of customary dispersants.
- 100 g of polyamide 6 fibers are introduced into 2000 ml of an aqueous dye liquor, which contains 0.1 g of the copper complex of the formula and 0.5 g of the metal complex dye of the formula contains.
- a pH of 6 is set by adding acetic acid. Then the temperature of the liquor is slowly increased with occasional stirring. It is dyed at 98 ° C for 1 hour.
- the goods are then removed from the dye bath and rinsed thoroughly.
- the dyeing produced in this way shows improved lightfastness compared to the dyeing not treated with (1).
- the staining can also be done under HT conditions, i.e. H. at temperatures of 110-130 ° C in an autoclave.
- a polyamide 6 fabric 100 g of a polyamide 6 fabric are placed in 2000 ml of an aqueous dye liquor containing 0.5 g of the metal complex dye of the formula (2). It is dyed in the usual way at 98 ° C. and pH 6. After rinsing, drying is carried out and the polyamide fabric is impregnated with a liquor on a padder; which contains 1 g of compound (1) in dispersed form per liter of water.
- the pressure of the foulard rollers is set so that the impregnated polyamide doubles its dry weight when wet.
- the dyeing treated in this way shows improved lightfastness compared to the dyeing not treated.
- a further improvement in light fastness can be achieved if an impregnating liquor is used which contains 10.0 g of compound (3) in addition to (1).
- the dyeing produced in this way shows improved lightfastness compared to the dyeing not treated with (1).
- a further improvement in light fastness is achieved if, in addition to (1), 1.0 g of compound (3) are added to the liquor.
Description
- Die vorliegende Erfindung betrifft ein Verfahren zur Verbesserung der Lichtechtheit von mit Säurefarbstoffen oder Metallkomplexfarbstoffen gefärbten Polyamidfasern durch Behandlung mit Kupferkomplexverbindungen vor, während oder nach der Färbung.
- Es ist bereits bekannt, daß Plastikmaterialien, wie z. B. Fasern aus Polyamid, die gegebenenfalls irgendwelche Farbstoffe enthalten, mit Metallkomplexen von Schiff'schen Basen stabilisiert werden können. Über die Art der Farbstoffe und/oder die Verhinderung des Ausbleichens von Färbungen durch diese Hilfsmittel wird indessen nichts berichtet.
- Gemäß GB-A-1 321 645 werden unter anderem Chelate von Salicylaldehydabkömmlingen und Sc, Ti, V, Cr, Mn, Co, Cn und vor allem Ni zur Lichtechtheitsverbesserung von mit Küpenfarbstoffen gefärbten Cellulosematerialien eingesetzt.
- Aus US-A-3 203 752 war weiterhin bekannt, die Lichtechtheit von Polyolefin- und Polyacetalfärbungen durch Metallchelate bestimmter Stabilität, u. a. auch Kupfersalicylaldoxim, zu verbessern.
- Aus der DE-A-2 625 386 war bekannt, das Ausbleichen verschiedener Farbstoffgruppen durch den Zusatz von Singulett-Sauerstoff-desaktivierenden Substanzen, beispielsweise Ni-Salicylaldehydoxim-Komplexen zu verringern. Schließlich wird in American Dystuff Reporter 50 (1961), 583-588 und 51, (1964), 99-104 u. a. beschrieben, wie man die Lichtechtheit von Polyamidfärbungen mit metallfreien UV-Absorbern verbessern kann.
- Keiner dieser Publikation kann jedoch der Hinweis entnommen werden, daß Kupferkomplexe von Schiff'schen Basen des Salicylaldehyds besonders geeignet zur Lichtechtheitsverbesserung von mit bestimmten Farbstoffen gefärbten Polyamidfasern sind.
-
- R = C1―C18-Alkyl oder Cycloalkyl bedeutet und die Ringe A durch C1-C4-Alkyl, Cycloalkyl, C1―C4-Alkoxy, Halogen oder OH substituiert sein können.
- Die Verbindungen (I) werden dabei in Mengen von etwa 0,05-2%, vorzugsweise 0,1-0,2%, bezogen auf das Gewicht des Polyamids, eingesetzt. Vorzugsweise erfolgt der Zusatz der Verbindungen (1) zum Färbebad in Kombination mit gegebenenfalls weitersubstituierten 2-(2'-Hydroxyphenyl)-benzot- riazolen (111), insbesondere solchen der Formel
- X=H,CI
- R1, R2 = H, Alkyl, insbesondere C1―C4-Alkyl
- Die Verbindungen (II) und (III) werden dabei in Mengen von 0,5―4, vorzugsweise 1―2%, bezogen auf das Gewicht des Polyamids, eingesetzt.
- Die Verbindungen (1) erhält man in an sich bekannter Weise (vgl. z. B. US-A-3 361 710) durch Umsetzung der entsprechenden Ausgangsverbindungen mit - bevorzugt stöchiometrischen Mengen - eines Kupfersalzes, insbesondere eines Salzes einer Mineralsäure wie Kupfer-II-chlorid in vorzugsweise alkoholischen oder wäßrig-alkoholischen Medium.
- Unter Polyamid wird natürliches und synthetisches Polyamid verstanden.
- Die Färbungen können in herkömmlicher Weise sowohl mit Metallkomplexfarbstoffen als auch mit Säurefarbstoffen erzeugt werden.
- Als Metallkomplexfarbstoffe werden die bekannten Typen, insbesondere die 1 :2-Chrom- oder 1 : 2-Kobaltkomplexe von Mono- oder Disazofarbstoffen eingesetzt, die in der Literatur in großer Zahl beschrieben sind. Die Farbstoffe können insbesondere auch 1-2 Sulfogruppen enthalten.
- Geeignete Säurefarbstoffe sind handelsübliche Typen, die vorzugsweise in Kombination mit den Metallkomplexfarbstoffen eingesetzt werden.
- Die Verbindungen I kommen - sofern sie nicht wasserlöslich sind - selbstverständlich in fein verteilter Form, wie sie durch Mahlung in Gegenwart üblicher Dispergiermittel erhalten wird, zum Einsatz.
-
- 568 g Cyclohexylamin, 683 g Salicylaldehyd und 2,5 1 Toluol werden am Wasserabscheider unter Stickstoff am Rückfluß gehalten, bis kein Wasser mehr abgeschieden wird. Das Toluol wird unter reduziertem Druck abdestilliert. Der Rückstand wird mit einer Lösung aus 196 g Natriumhydroxyd und 2 I Methanol versetzt und 30 Min. zum Sieden erhitzt. Dann werden 448 g Kupfer-II-chloriddihydrat gelöst in 2 Methanol rasch unter Rühren zugetropft. Nach 30 Min. Rückfluß wird abgesaugt. Das Produkt kann aus DMF umkristallisiert werden. Man erhält braune Kristalle vom Schmelzpunkt 165-168° C.
- 100 g Polyamid-6-Fasern werden in 2000 ml einer wäßrigen Färbeflotte eingetragen, die 0,1 g des Kupferkomplexes der Formel
- Danach wird die Ware dem Färbebad entnommen und gründlich gespült.
- Die so hergestellte Färbung zeigt eine verbesserte Lichtechtheit gegenüber der nicht mit (1) behandelten Färbung.
-
- Die Färbung kann auch unter HT-Bedingungen, d. h. bei Temperaturen von 110-130°C im Autoklaven, durchgeführt werden.
- 100 g eines Polyamid-6-Gewebes werden in 2000 ml einer wäßrigen Färbeflotte gegeben, die 0,5 g des Metallkomplex-Farbstoffes der Formel (2) enthält. Es wird in üblicher Weise bei 98°C und pH 6 gefärbt. Nach dem Spülen wird getrocknet und das Polyamidgewebe auf einem Foulard mit einer Flotte imprägniert; die pro Liter Wasser 1 g der Verbindung (1) in dispergierter Form enthält.
- Der Druck der Foulard-Walzen ist so eingestellt, daß das imprägnierte Polyamid im feuchten Zustand sein Trockengewicht verdoppelt.
- Nach dem Imprägnier-Vorgang wird bei 180° C 30 Sekunden getrocknet und fixiert.
- Die so behandelte Färbung zeigt gegenüber der nicht behandelten Färbung eine verbesserte Lichtechtheit.
- Eine weitere Verbesserung der Lichtechtheit kann erreicht werden, wenn eine Imprägnierflotte verwendet wird, die zusätzlich zu (1) noch 10,0 g der Verbindung (3) enthält.
-
- Die so hergestellte Färbung zeigt eine verbesserte Lichtechtheit gegenüber der nicht mit (1) behandelten Färbung.
-
einsetzt.
und/oder gegebenenfalls weitersubstituierten 0,0'-Dihydroxybenzophenonen (11), insbesondere 4,4'-Dialkoxy-2,2'-dihydroxybenzophenonen (111) eingesetzt.
Claims (4)
einsetzt.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3041153 | 1980-10-31 | ||
DE19803041153 DE3041153A1 (de) | 1980-10-31 | 1980-10-31 | Verfahren zur verbesserung der lichtechtheit von polyamidfaerbungen |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0051188A1 EP0051188A1 (de) | 1982-05-12 |
EP0051188B1 true EP0051188B1 (de) | 1984-07-18 |
Family
ID=6115701
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP81108415A Expired EP0051188B1 (de) | 1980-10-31 | 1981-10-16 | Verfahren zur Verbesserung der Lichtechtheit von Polyamidfärbungen |
Country Status (4)
Country | Link |
---|---|
US (1) | US4383835A (de) |
EP (1) | EP0051188B1 (de) |
JP (1) | JPS57101083A (de) |
DE (2) | DE3041153A1 (de) |
Families Citing this family (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3247051A1 (de) * | 1982-12-20 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur verbesserung der lichtechtheit von polyamidfaerbungen |
DE3417782A1 (de) * | 1983-05-23 | 1984-11-29 | Sandoz-Patent-GmbH, 7850 Lörrach | Faerbereihilfsmittel |
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 |
DE3326640A1 (de) * | 1983-07-23 | 1985-01-31 | Basf Ag, 6700 Ludwigshafen | Verfahren zur verbesserung der lichtechtheit von faerbungen mit saeure- oder metallkomplexfarbstoffen auf polyamid |
EP0162811B1 (de) * | 1984-05-22 | 1989-10-11 | Ciba-Geigy Ag | Verfahren zur fotochemischen Stabilisierung von Polyamidfasermaterial |
EP0181836B1 (de) * | 1984-11-09 | 1988-12-21 | Ciba-Geigy Ag | Verfahren zur Verbesserung der Lichtechtheit von Lederfärbungen |
EP0185611B1 (de) * | 1984-12-21 | 1988-09-21 | Ciba-Geigy Ag | Verfahren zur fotochemischen Stabilisierung von synthetischen Polyamidfasermaterialien |
EP0200843B1 (de) * | 1985-05-09 | 1988-06-22 | Ciba-Geigy Ag | Verfahren zur fotochemischen Stabilisierung von ungefärbtem und gefärbtem Polyamidfasermaterial und dessen Mischungen |
US4775386A (en) * | 1986-05-05 | 1988-10-04 | Ciba-Geigy Corporation | Process for photochemical stabilization of undyed and dyed polyamide fibre material and blends thereof with other fibres: copper complex and light stabilizer treatment |
ZA873171B (en) * | 1986-05-05 | 1987-12-30 | Ciba Geigy Ag | Process for the photochemical stabilization of undyed and dyed polyamide fibre material and blends thereof with other fibres |
DE3622864A1 (de) * | 1986-07-08 | 1988-01-21 | Bayer Ag | Verfahren zur verbesserung der lichtechtheit von polyamidfaerbungen |
US4874391A (en) * | 1986-07-29 | 1989-10-17 | Ciba-Geigy Corporation | Process for photochemical stabilization of polyamide fiber material and mixtures thereof with other fibers: water-soluble copper complex dye and light-stabilizer |
US4813970A (en) * | 1988-02-10 | 1989-03-21 | Crompton & Knowles Corporation | Method for improving the lightfasteness of nylon dyeings using copper sulfonates |
US5700850A (en) | 1993-08-05 | 1997-12-23 | Kimberly-Clark Worldwide | Colorant compositions and colorant stabilizers |
US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
US5645964A (en) | 1993-08-05 | 1997-07-08 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
US6017471A (en) | 1993-08-05 | 2000-01-25 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
US5773182A (en) | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
US5721287A (en) | 1993-08-05 | 1998-02-24 | Kimberly-Clark Worldwide, Inc. | Method of mutating a colorant by irradiation |
US6242057B1 (en) | 1994-06-30 | 2001-06-05 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition and applications therefor |
US6071979A (en) | 1994-06-30 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition method of generating a reactive species and applications therefor |
US5685754A (en) | 1994-06-30 | 1997-11-11 | Kimberly-Clark Corporation | Method of generating a reactive species and polymer coating applications therefor |
US6008268A (en) | 1994-10-21 | 1999-12-28 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition, method of generating a reactive species, and applications therefor |
US5786132A (en) | 1995-06-05 | 1998-07-28 | Kimberly-Clark Corporation | Pre-dyes, mutable dye compositions, and methods of developing a color |
SK160497A3 (en) | 1995-06-05 | 1998-06-03 | Kimberly Clark Co | Novel pre-dyes |
MX9710016A (es) | 1995-06-28 | 1998-07-31 | Kimberly Clark Co | Colorantes novedosos y modificadores de colorante. |
DE69620428T2 (de) | 1995-11-28 | 2002-11-14 | Kimberly Clark Co | Lichtstabilisierte fabstoffzusammensetzungen |
US5855655A (en) | 1996-03-29 | 1999-01-05 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6099628A (en) | 1996-03-29 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5782963A (en) | 1996-03-29 | 1998-07-21 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5891229A (en) | 1996-03-29 | 1999-04-06 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6524379B2 (en) | 1997-08-15 | 2003-02-25 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
JP2002517540A (ja) | 1998-06-03 | 2002-06-18 | キンバリー クラーク ワールドワイド インコーポレイテッド | インク及びインクジェット印刷用のネオナノプラスト及びマイクロエマルション技術 |
SK1552000A3 (en) | 1998-06-03 | 2000-08-14 | Kimberly Clark Co | Novel photoinitiators and applications therefor |
BR9912003A (pt) | 1998-07-20 | 2001-04-10 | Kimberly Clark Co | Composições de tinta para jato de tinta aperfeiçoadas |
CA2353685A1 (en) | 1998-09-28 | 2000-04-06 | Kimberly-Clark Worldwide, Inc. | Chelates comprising chinoid groups as photoinitiators |
ES2195869T3 (es) | 1999-01-19 | 2003-12-16 | Kimberly Clark Co | Nuevos colorantes, estabilizantes de colorantes, compuestos de tinta y metodos mejorados para su fabricacion. |
US6331056B1 (en) | 1999-02-25 | 2001-12-18 | Kimberly-Clark Worldwide, Inc. | Printing apparatus and applications therefor |
US6294698B1 (en) | 1999-04-16 | 2001-09-25 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6368395B1 (en) | 1999-05-24 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Subphthalocyanine colorants, ink compositions, and method of making the same |
JP2001131883A (ja) * | 1999-10-29 | 2001-05-15 | Milliken Japan Kk | 着色された漂白剤耐久性のパイルファブリック及び前記パイルファブリックを具備するフロアマット物品 |
US6486227B2 (en) | 2000-06-19 | 2002-11-26 | Kimberly-Clark Worldwide, Inc. | Zinc-complex photoinitiators and applications therefor |
JP5938820B2 (ja) * | 2011-01-31 | 2016-06-22 | 国立大学法人 東京大学 | 蓄熱材及びそれを利用した熱利用システム |
CN103265565B (zh) * | 2013-05-31 | 2016-04-06 | 桂林理工大学 | 3,5-二溴水杨酸吖嗪双希夫碱铜配合物的原位合成方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL287100A (de) * | 1961-12-22 | |||
US3329696A (en) * | 1963-06-17 | 1967-07-04 | Universal Oil Prod Co | N-(2-hydroxyphenylmethylene)-cycloalkyl amines and metal salts thereof |
US3363969A (en) * | 1964-02-12 | 1968-01-16 | Du Pont | Dyeing and light stabilizing nylon yarns with sulfonated dyes; sterically hindered phenols, and alkylnaphthalene sulfonates with or without other ultraviolet light absorbers |
GB1321645A (en) * | 1970-07-02 | 1973-06-27 | Ici Ltd | Colouration process |
GB1392953A (en) * | 1972-07-18 | 1975-05-07 | Ici Ltd | Colouration process |
DE2625386A1 (de) * | 1976-06-05 | 1977-12-15 | Manfred Rembold | Farbstoffe mit verringerter katalytischer ausbleichung, faerbverfahren und inhibitoren zur verringerung der katalytischen ausbleichung |
-
1980
- 1980-10-31 DE DE19803041153 patent/DE3041153A1/de not_active Withdrawn
-
1981
- 1981-10-15 US US06/311,490 patent/US4383835A/en not_active Expired - Fee Related
- 1981-10-16 EP EP81108415A patent/EP0051188B1/de not_active Expired
- 1981-10-16 DE DE8181108415T patent/DE3164902D1/de not_active Expired
- 1981-10-27 JP JP56170852A patent/JPS57101083A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JPS57101083A (en) | 1982-06-23 |
US4383835A (en) | 1983-05-17 |
EP0051188A1 (de) | 1982-05-12 |
DE3164902D1 (en) | 1984-08-23 |
DE3041153A1 (de) | 1982-06-16 |
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