EP1602779A1 - Complexes de cuivre en tant que photostabilisants pour textiles - Google Patents

Complexes de cuivre en tant que photostabilisants pour textiles Download PDF

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Publication number
EP1602779A1
EP1602779A1 EP04013229A EP04013229A EP1602779A1 EP 1602779 A1 EP1602779 A1 EP 1602779A1 EP 04013229 A EP04013229 A EP 04013229A EP 04013229 A EP04013229 A EP 04013229A EP 1602779 A1 EP1602779 A1 EP 1602779A1
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EP
European Patent Office
Prior art keywords
parts
compounds
formula
minutes
added
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.)
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Application number
EP04013229A
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German (de)
English (en)
Inventor
Erfindernennung liegt noch nicht vor Die
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant International Ltd
Original Assignee
Clariant International Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Clariant International Ltd filed Critical Clariant International Ltd
Priority to EP04013229A priority Critical patent/EP1602779A1/fr
Priority to DE602005025488T priority patent/DE602005025488D1/de
Priority to JP2007514206A priority patent/JP2008501817A/ja
Priority to CNB2005800181294A priority patent/CN100503963C/zh
Priority to ES05750523T priority patent/ES2354892T3/es
Priority to US11/628,531 priority patent/US20080010755A1/en
Priority to EP05750523A priority patent/EP1774086B8/fr
Priority to PCT/IB2005/001688 priority patent/WO2005118949A1/fr
Priority to AT05750523T priority patent/ATE492681T1/de
Publication of EP1602779A1 publication Critical patent/EP1602779A1/fr
Withdrawn legal-status Critical Current

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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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/5214—Polymers of unsaturated compounds containing no COOH groups or functional derivatives thereof
    • D06P1/5228—Polyalkenyl alcohols, e.g. PVA
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/56—Condensation products or precondensation products prepared with aldehydes
    • 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
    • D06P1/60—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 polyethers
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
    • D06P1/6133—Addition products of hydroxyl groups-containing compounds with oxiranes from araliphatic or aliphatic alcohols
    • 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
    • D06P1/60—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 polyethers
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6138—Polymerisation products of glycols, e.g. Carbowax, Pluronics
    • 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

Definitions

  • the present invention relates to organic copper complexes based on bisazomethines, which the dyeing of textiles, in particular undyed polyamide, as light stabilizers Be dyed bath and leave much less copper in the dyeing waste water than before used substances.
  • EP 0 245 204 A1 discloses a process for photochemical stabilization of undyed and dyed polyamide fiber material or mixtures thereof with others Fiber materials disclosed, wherein the fiber material with a mixture of an organic Copper complex, a light stabilizer and optionally an antioxidant is treated.
  • n is 0 or 1, preferably 0, and M is H or methyl.
  • Particularly useful are compounds wherein n is 0, M is H or methyl, and R is H or wherein both R's together with the C atoms to which they are attached, an aliphatic ring with 6 C atoms form.
  • the hydrogen atoms in the two -OH groups may also be represented by methyl be replaced, such as in formula (IV).
  • the present compounds can be prepared by reacting 2,4-dihydroxybenzophenone or 2-hydroxy-4-methoxybenzophenone with a C 2 -C 4 -alkylenediamine, 1,2-diaminocyclohexane or with o-phenylenediamine and then reacting further with a copper salt ,
  • 2,4-dihydroxybenzophenone and ethylenediamine are used as starting materials used.
  • the copper compounds according to the invention are suitably in the form of aqueous Dispersions used, wherein the concentration of active substance in the range of 2 to 30, preferably from 5 to 15% by weight.
  • the dispersions are prepared by milling in the presence obtained conventional dispersant.
  • the compounds mentioned or the dispersions mentioned are outstandingly suitable as light-stabilizing additive to the textile dye baths, in particular for fibers or fabrics undyed polyamide, the wastewater is much less loaded with copper than with other commercially available light stabilizers for polyamide, given the environmental issues represents an important technical advantage.
  • Another object of the present invention is thus the use of the described Compounds or dispersions containing these compounds as a light-stabilizing additive to the dyebaths for textiles. Especially for undyed polyamide brings this application significant improvements to the state of the art.
  • This product is dissolved at 100 ° C in 450 ml of dimethylformamide. To this solution is added within 10 minutes a solution consisting of 28.60 g of copper sulfate pentahydrate, 64 ml of ammonia solution (25%) and 125 ml of water. After about 10 minutes, a pink solid precipitates. After 2 hours under reflux, it is cooled to room temperature, the precipitate is filtered, and washed with 200 ml of water. The presscake is dried at 60 ° C in a vacuum.
  • This product is dissolved at 100 ° C in 500 ml of dimethylformamide. To this solution is added within 10 minutes, a solution consisting of 25.60 g of copper sulfate pentahydrate, 60 ml of ammonia solution (25%) and 125 water. After about 10 minutes, a dark green solid begins to precipitate. After 2 hours of heating under reflux, it is cooled to room temperature, the precipitate is filtered, and washed with 200 ml of water. The presscake is dried at 60 ° C in a vacuum.
  • This product is dissolved at 100 ° C in 500 ml of dimethylformamide. To this solution is added within 10 minutes a solution consisting of 30.4 g of copper sulfate pentahydrate, 66 ml of ammonia solution (25%) and 125 ml of water. After about 10 minutes, a dark green solid begins to precipitate. After 2 more hours under reflux, it is cooled to room temperature, the precipitate is filtered, and washed with 200 ml of water. The presscake is dried at 60 ° C in a vacuum.
  • the liquor 1 part of a commercial leveling agent (eg Sandogen® NH liquid from Clariant) may be added.
  • a commercial leveling agent eg Sandogen® NH liquid from Clariant
  • the lightfastness according to ISO standard 105-B06 (2, 4 and 6 FAKRA) is measured and the content of residual copper in the dyebaths determined.
  • the liquor 1 part of a commercial leveling agent (eg Sandogen® NH liquid from Clariant) may be added.
  • a commercial leveling agent eg Sandogen® NH liquid from Clariant
  • the lightfastness according to ISO standard 105-B06 (2, 4 and 6 FAKRA) is measured and the content of residual copper in the dyebaths determined.
  • the pH of the dyebath is adjusted to 6 in the dyeing apparatus, the dyebath is heated to 98.degree. C. over 30 minutes, and dyeing is continued for 1 hour at this temperature. It is then cooled and the resulting gray color thoroughly rinsed cold and dried at room temperature.
  • the liquor 1 part of a commercial leveling agent eg Sandogen® NH liquid from Clariant
  • a commercial leveling agent eg Sandogen® NH liquid from Clariant
  • Polyamide Nylsuisse and Autovelours (Dura) from BMW (Bayharide Motorenwerke, Kunststoff, Germany) were also used with a similar formula.
  • the lightfastness according to ISO standard 105-B06 (2, 4 and 6 FAKRA) is measured and the content of residual copper in the dyebaths determined.
  • the liquor 1 part of a commercial leveling agent eg Sandogen® NH liquid from Clariant
  • a commercial leveling agent eg Sandogen® NH liquid from Clariant
  • the lightfastness according to ISO standard 105-B06 (2, 4 and 6 FAKRA) is measured and the content of residual copper in the dyebaths determined.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP04013229A 2004-06-04 2004-06-04 Complexes de cuivre en tant que photostabilisants pour textiles Withdrawn EP1602779A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
EP04013229A EP1602779A1 (fr) 2004-06-04 2004-06-04 Complexes de cuivre en tant que photostabilisants pour textiles
DE602005025488T DE602005025488D1 (de) 2004-06-04 2005-05-23 Verwendung von kupferkomplexen als lichtschutzmittel für textilien
JP2007514206A JP2008501817A (ja) 2004-06-04 2005-05-23 テキスタイルのための耐光性剤としての銅錯体の使用
CNB2005800181294A CN100503963C (zh) 2004-06-04 2005-05-23 铜络合物作为纺织品光稳定剂的用途
ES05750523T ES2354892T3 (es) 2004-06-04 2005-05-23 Usos de complejos con cobre como agentes fotoestabilizadores para materiales textiles.
US11/628,531 US20080010755A1 (en) 2004-06-04 2005-05-23 Use Of Copper Complexes As Light Stabilzers For Textiles
EP05750523A EP1774086B8 (fr) 2004-06-04 2005-05-23 Utilisation de complexes de cuivre en tant que photostabilisants pour textiles
PCT/IB2005/001688 WO2005118949A1 (fr) 2004-06-04 2005-05-23 Utilisation de complexes de cuivre en tant que photostabilisants pour textiles
AT05750523T ATE492681T1 (de) 2004-06-04 2005-05-23 Verwendung von kupferkomplexen als lichtschutzmittel für textilien

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP04013229A EP1602779A1 (fr) 2004-06-04 2004-06-04 Complexes de cuivre en tant que photostabilisants pour textiles

Publications (1)

Publication Number Publication Date
EP1602779A1 true EP1602779A1 (fr) 2005-12-07

Family

ID=34925252

Family Applications (2)

Application Number Title Priority Date Filing Date
EP04013229A Withdrawn EP1602779A1 (fr) 2004-06-04 2004-06-04 Complexes de cuivre en tant que photostabilisants pour textiles
EP05750523A Not-in-force EP1774086B8 (fr) 2004-06-04 2005-05-23 Utilisation de complexes de cuivre en tant que photostabilisants pour textiles

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP05750523A Not-in-force EP1774086B8 (fr) 2004-06-04 2005-05-23 Utilisation de complexes de cuivre en tant que photostabilisants pour textiles

Country Status (8)

Country Link
US (1) US20080010755A1 (fr)
EP (2) EP1602779A1 (fr)
JP (1) JP2008501817A (fr)
CN (1) CN100503963C (fr)
AT (1) ATE492681T1 (fr)
DE (1) DE602005025488D1 (fr)
ES (1) ES2354892T3 (fr)
WO (1) WO2005118949A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115417792B (zh) * 2022-08-31 2023-10-13 万华化学集团股份有限公司 适合低温潮湿环境中使用的环氧树脂固化剂、其制备方法与应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3573626D1 (en) * 1984-05-22 1989-11-16 Ciba Geigy Ag Process for the photochemical stabilisation of materials containing polyamide fibres
EP0181836B1 (fr) * 1984-11-09 1988-12-21 Ciba-Geigy Ag Procédé d'amélioration de la solidité à la lumière de cuirs teints
DE3563462D1 (en) * 1985-05-09 1988-07-28 Ciba Geigy Ag Process for the photochemical stabilisation of undyed and dyed polyamide fibrous material and its mixtures

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
ANGEWANDTE MAKROMOLEKULARE CHEMIE , 138, 159-66 CODEN: ANMCBO; ISSN: 0003-3146, 1986 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; DINJUS, U. ET AL: "Schiff bases of substituted o-hydroxybenzophenones and .alpha.,.omega.-diamines as ligands in 3d-element complexes", XP002307058, retrieved from STN Database accession no. 1980:487584 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; GUO, YING-CHEN: "Synthesis of N,N'-bis(o-hydroxy-p-methoxybenzophenone)ethylenediamine complexes with copper(II), nickel(II) and cobalt(II)", XP002307054, retrieved from STN Database accession no. 2002:403532 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; JENSEN, H. P.: "Structure of copper(II) complexes with Schiff bases derived from reaction of diamines with dihydroxybenzophenone and dihydroxyacetophenone", XP002307057, retrieved from STN Database accession no. 1984:521900 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; SPIRATOS, MIHAELA ET AL: "Coordination polymers. 7. Synthesis and characterization of some polychelates derived from bisphenolic complexes", XP002307056, retrieved from STN Database accession no. 1986:207809 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; SPIRATOS, MIHAELA ET AL: "Oxygen-carrying polychelates derived from bisphenolic complexes", XP002307055, retrieved from STN Database accession no. 1992:165030 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; ZARZHETSKAYA, L. K. ET AL: "Thermostable molding composition", XP002307059, retrieved from STN Database accession no. 1976:106625 *
INDIAN JOURNAL OF CHEMISTRY, SECTION A: INORGANIC, PHYSICAL, THEORETICAL & ANALYTICAL , 23A(6), 475-6 CODEN: IJCADU; ISSN: 0376-4710, 1984 *
INORG. ORGANOMET. OLIGOMERS POLYM., PROC. IUPAC SYMP. MACROMOL., 33RD , MEETING DATE 1990, 295-300. EDITOR(S): HARROD, JOHN FRANK; LAINE, RICHARD M. PUBLISHER: KLUWER, DORDRECHT, NETH. CODEN: 57OAAE, 1991 *
YINGYONG HUAXUE , 19(5), 503-505 CODEN: YIHUED; ISSN: 1000-0518, 2002 *
ZEITSCHRIFT FUER ANORGANISCHE UND ALLGEMEINE CHEMIE , 464, 37-44 CODEN: ZAACAB; ISSN: 0044-2313, 1980 *

Also Published As

Publication number Publication date
US20080010755A1 (en) 2008-01-17
CN1969085A (zh) 2007-05-23
DE602005025488D1 (de) 2011-02-03
ES2354892T3 (es) 2011-03-18
JP2008501817A (ja) 2008-01-24
CN100503963C (zh) 2009-06-24
EP1774086A1 (fr) 2007-04-18
WO2005118949A1 (fr) 2005-12-15
EP1774086B1 (fr) 2010-12-22
EP1774086B8 (fr) 2011-01-26
ATE492681T1 (de) 2011-01-15

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