WO2012171638A1 - Mélanges de colorants acides pour polyamide et laine contenant des colorants acides dimériques - Google Patents

Mélanges de colorants acides pour polyamide et laine contenant des colorants acides dimériques Download PDF

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Publication number
WO2012171638A1
WO2012171638A1 PCT/EP2012/002497 EP2012002497W WO2012171638A1 WO 2012171638 A1 WO2012171638 A1 WO 2012171638A1 EP 2012002497 W EP2012002497 W EP 2012002497W WO 2012171638 A1 WO2012171638 A1 WO 2012171638A1
Authority
WO
WIPO (PCT)
Prior art keywords
dye
hydrogen
acid
sulfo
wool
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.)
Ceased
Application number
PCT/EP2012/002497
Other languages
German (de)
English (en)
Inventor
Helmut Sieber
Rainer Nusser
Rino Marazzi
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 EP12727801.8A priority Critical patent/EP2721113A1/fr
Priority to BR112013032249A priority patent/BR112013032249A2/pt
Priority to MX2013014769A priority patent/MX2013014769A/es
Priority to JP2014515091A priority patent/JP2014519543A/ja
Priority to KR1020147001074A priority patent/KR20140041744A/ko
Priority to CN201280029412.7A priority patent/CN103619962A/zh
Publication of WO2012171638A1 publication Critical patent/WO2012171638A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • 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
    • 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

Definitions

  • Acid dyes are mainly used to dye wool, others
  • Acid dye on polyamide can differ significantly from those on wool. These are, for example, the color itself
  • Acid dye mixture on polyamide, wool and on polyamide / wool blended fibers provides good reproducible colorations with good wet fastness.
  • the present invention is an acid dye mixture comprising
  • R1 is H, d-Ce-alkyl
  • R 2 is H, C 1 -C 6 alkyl; b) from 5 to 30% by weight, preferably from 5 to 20% by weight, particularly preferably from 10 to 15% by weight, of at least one dye B having the general structure (B)
  • R 3 is H, phenyl, where phenyl is substituted or unsubstituted
  • C C double bond an unsubstituted or substituted phenyl ring, R6 H, sulfo;
  • weight percentages are based on the total weight of the
  • Acid dye mixture are related.
  • the positive charge in formula (B) is usually substituted by a negative charge of a sulfo group contained in the molecule or by an equivalent of an anion, e.g. B. Cl " , VT S0 4 2" neutralized.
  • sulfo is a radical of formula S0 3 M.
  • M is preferably a single negative charge, hydrogen, an alkali metal or ammonium.
  • alkali metal preferably means Li, Na, or K, especially Na.
  • ammonium is preferably NH 4 + ,
  • Substituted phenyl ring preferably denotes a phenyl radical which is mono- or polysubstituted, preferably mono-, di- or trisubstituted, by one or more substituents selected from the group consisting of C 1 -C 4 -alkyl, halogen, C 1 -C 4 -alkoxy, hydroxy, sulfo , Amino or nitro are particularly preferred substituents are methyl, Cl, amino, methoxy, ethoxy and sulfo.
  • R 1 and R 2 independently of one another are hydrogen or methyl.
  • R 3 is hydrogen, unsubstituted phenyl or phenyl substituted with amino, sulfo and / or ethoxy.
  • R5 is hydrogen or methoxy, or in a likewise preferred embodiment, R4 and R5
  • Preferred dyes of the formula (B) are those in which
  • R3 is hydrogen or unsubstituted phenyl
  • R4 is hydrogen or sulfo
  • R5 is hydrogen or methoxy
  • R6 is hydrogen or sulfo
  • R3 is phenyl substituted with amino, sulfo and / or ethoxy
  • R4 is hydrogen or sulfo
  • R6 is hydrogen
  • the dyes of the formulas (A) and (B) are known per se and can be prepared by known methods, for example as described in: Ulimann, 6.Aveml., 0.1002 / 14356007. a02_355, pages 1 - 68
  • Another object of the present invention is a process for the preparation of the acid dye mixture described above, by mixing the at least one dye A with the at least one dye B in the weight ratios indicated above, for example in the form of their dry powder, press cake or preferably aqueous solutions.
  • the dyes A and B can also be mixed together only in the dyebath.
  • the dye mixtures according to the invention are particularly suitable for fibrous material which consists of natural and / or synthetic
  • Polyamides consists of dyeing or printing in blue tones.
  • the dye mixtures according to the invention are also suitable for producing inkjet printing inks and for printing with these fibrous material which consists of natural and / or synthetic polyamides or cellulose (eg paper).
  • Another object of the invention is the use of said
  • Another object of the invention is the use of said
  • the dyeing is carried out according to known methods, such as. B. the
  • the substrate to be dyed z. B. in the form of yarn, fabric, knitted or carpet. Fully-fashioned dyeings are also on delicate substrates, eg. Lambswool, cashmere, alpaca and mohair very well possible. Particularly suitable are the dye mixtures according to the invention for dyeing fine-denier fibers (microfibers).
  • the dye mixtures according to the invention show good compatibility with known acid dyes. Accordingly, the dye mixtures may be used alone in a dyeing or printing process or as a blue component in a combination dyeing or printing composition along with other acid dyes of the same class, i. H. With
  • Acid dyes which have comparable dyeing properties, such as fastness properties and Ausziehraten from Därbebad on the substrate.
  • the dyes of the present invention may be used in conjunction with other acid dyes.
  • the dye mixtures according to the invention are particularly suitable for dyeing wool, silk and all nylon types on which dyeings having a high level of fastness, in particular good light fastness and good
  • the dye mixtures according to the invention can also be used as blue components in the trichromatic dyeing process or trichromatic printing process.
  • Trichromiefärben or printing can be used on all conventional and known dyeing and printing methods, such as. B. the
  • Trichromatic dye mixture used in the process of the invention depends on the desired shade. For a shade of brown you can
  • a yellow component 20-40% by weight of a yellow component, 40-60% by weight of an orange or red component and 10-20% by weight of an acid dye mixture according to the invention are used as the blue component.
  • parts are parts by weight and percentages are by weight.
  • a dyebath of 40 ° C consisting of 2000 parts of water, 1 part of a weakly cationic, dye-affinity leveling agent based on an ethoxylated aminopropyl fatty acid amide, 0.25 parts of the following
  • Example 1b (wool dyeing):
  • a dyebath of 40 ° C consisting of 4000 parts of water, 1 part of a weakly dye affinity leveling agent with amphoteric character on the basis of a sulfated, ethoxylated fatty acid amide, 0.4 parts of the dye mixture of Example 1a, with 1 - 2 parts 40% Acetic acid was adjusted to pH 5, 100 parts of wool fabric are added. After 10 minutes at 40 ° C, the dyebath with a temperature increase of 1 ° C per minute on
  • Wool fabric is taken out of the bath, rinsed with warm and then cold water and dried. The result is a blue level wool dyeing with good light and wet fastness with excellent levelness within the fiber (root-tip).
  • the dyes of Examples 2 to 18 listed in the table below are mixed in the ratio Dye B: Dye A of 1: 9 or of 2: 8 and used for dyeing in analogy to Examples 1a and 1b.
  • the dye mixtures of the invention provide on the respective substrate (polyamide or wool) well reproducible, level dyeings with very good wet and light fastness. 10
  • a dye bath of 40 ° C consisting of 2000 parts of water, 1 part of a weakly cationic dye-like leveling agent based on an ethoxylated Aminopropylfettklamids, 0.3 parts of a dye mixture from Example 1a, with 1-2 parts of 40% acetic acid to pH 5.5, 100 parts of nylon 6,6 fabric are added. After 10 minutes at 40 ° C, the dyebath is heated with a temperature increase of 1.5 ° C per minute to 120 ° C and then left for 15-25 minutes at this temperature.
  • Polyamide 6,6 fabric is removed from the dyebath, rinsed with warm and then cold water and dried. It results in a blue one
  • Dye mixture from Example 1a which was adjusted to pH 5 with 1 to 2 parts of 40% acetic acid are added to 100 parts of polyamide 6.6 fabric. After 10 minutes at 40 ° C, the dyebath is heated with a temperature increase of 1 ° C per minute to 98 ° C and then left for 45 to 60 minutes at boiling temperature. It is then cooled to 70 ° C within 15 minutes. The dyed fabric is removed from the bath, rinsed with warm and then cold water and dried. The result is a level gray polyamide dyeing, which shows good light and wet fastness.
  • Example 23 Example 23
  • Example 24 (wool / polyamide blended fabric dyeing)
  • a dyebath of 40 ° C consisting of 4000 parts of water, 1 part of a weakly dye affinity leveling agent with amphoteric character on the basis of a sulfated, ethoxylated fatty acid amide, 0.4 parts of the dye mixture of Example 1a, with 1 - 2 parts 40% Acetic acid adjusted to pH 5 100 parts of wool / polyamide blended fabric are added.
  • the dyebath is heated to boiling temperature with a temperature increase of 1 ° C per minute and then left for 40 - 60 minutes at boiling temperature.
  • the mixture is then cooled to 70 ° C within 20 minutes.
  • the dyed wool / polyamide blend is removed from the bath, rinsed with warm and then cold water and dried. The result is a blue level wool / polyamide blend fabric dyeing with good light and wet fastness properties with excellent levelness within the wool fiber (root-lace) and equal shade on nylon and wool fibers.
  • Example 1a prepared and a polyamide 6 fabric dyed analogously to Example 1a.
  • Example 1b prepared and a wool fabric dyed analogously to Example 1b. It creates a restless appearance.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

L'invention concerne un mélange de colorants acides comprenant a) de 70 à 95% en poids d'au moins un colorant A présentant la structure générale (A) et b) de 5 à 30 % en poids d'au moins un colorant B présentant la structure générale (B).
PCT/EP2012/002497 2011-06-16 2012-06-13 Mélanges de colorants acides pour polyamide et laine contenant des colorants acides dimériques Ceased WO2012171638A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP12727801.8A EP2721113A1 (fr) 2011-06-16 2012-06-13 Mélanges de colorants acides pour polyamide et laine contenant des colorants acides dimériques
BR112013032249A BR112013032249A2 (pt) 2011-06-16 2012-06-13 misturas de corantes ácidos para poliamida e lã contendo corantes ácidos dímeros
MX2013014769A MX2013014769A (es) 2011-06-16 2012-06-13 Mezclas de colorante acido para poliamida y lana, que contienen colorantes acidos dimericos.
JP2014515091A JP2014519543A (ja) 2011-06-16 2012-06-13 二量体酸性染料を含有するポリアミド及び羊毛のための酸性染料混合物
KR1020147001074A KR20140041744A (ko) 2011-06-16 2012-06-13 이합체 산성 염료를 함유한, 폴리아미드 및 양모용 산성 염료 혼합물
CN201280029412.7A CN103619962A (zh) 2011-06-16 2012-06-13 包含二聚酸性染料的用于聚酰胺和羊毛的酸性染料混合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102011104362.8 2011-06-16
DE102011104362 2011-06-16

Publications (1)

Publication Number Publication Date
WO2012171638A1 true WO2012171638A1 (fr) 2012-12-20

Family

ID=46317338

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/002497 Ceased WO2012171638A1 (fr) 2011-06-16 2012-06-13 Mélanges de colorants acides pour polyamide et laine contenant des colorants acides dimériques

Country Status (8)

Country Link
EP (1) EP2721113A1 (fr)
JP (1) JP2014519543A (fr)
KR (1) KR20140041744A (fr)
CN (1) CN103619962A (fr)
BR (1) BR112013032249A2 (fr)
MX (1) MX2013014769A (fr)
TW (1) TW201313840A (fr)
WO (1) WO2012171638A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201611573D0 (en) 2016-07-01 2016-08-17 Technip France Sas Cracking furnace
CN110128847B (zh) * 2019-05-18 2020-09-29 上海雅运新材料有限公司 一种蓝色酸性染料组合物及其在纤维上的染色应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2732586A1 (de) * 1976-07-22 1978-01-26 Ciba Geigy Ag Verfahren zum faerben linearer polyester in der schmelze
EP0726297A1 (fr) * 1995-02-10 1996-08-14 Ciba-Geigy Ag Mélanges de colorants et leur utilisation
WO2002046318A1 (fr) 2000-12-05 2002-06-13 Clariant Finance (Bvi) Limited Procede de teinture trichromatique
WO2008090091A1 (fr) * 2007-01-26 2008-07-31 Unilever Plc Composition de nuançage
WO2011045195A1 (fr) * 2009-10-13 2011-04-21 Unilever Plc Polymères colorants

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4514187A (en) * 1982-07-21 1985-04-30 Ciba-Geigy Corporation Process for dyeing differential-dyeing polyamide fibres
DE3466715D1 (en) * 1983-05-25 1987-11-12 Ciba Geigy Ag Trichromatic dyeing or printing process
GB8424137D0 (en) * 1983-09-29 1984-10-31 Sandoz Ltd Organic compounds
JP3290486B2 (ja) * 1992-12-14 2002-06-10 田岡化学工業株式会社 ポリアミド繊維用染料組成物、その染色法及びその染色物
JP4073202B2 (ja) * 2000-11-13 2008-04-09 オリヱント化学工業株式会社 レーザー光透過性着色樹脂組成物用着色剤及びその関連技術
PL1945747T3 (pl) * 2006-08-10 2010-02-26 Unilever Nv Cieniująca kolor kompozycja

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2732586A1 (de) * 1976-07-22 1978-01-26 Ciba Geigy Ag Verfahren zum faerben linearer polyester in der schmelze
EP0726297A1 (fr) * 1995-02-10 1996-08-14 Ciba-Geigy Ag Mélanges de colorants et leur utilisation
WO2002046318A1 (fr) 2000-12-05 2002-06-13 Clariant Finance (Bvi) Limited Procede de teinture trichromatique
WO2008090091A1 (fr) * 2007-01-26 2008-07-31 Unilever Plc Composition de nuançage
WO2011045195A1 (fr) * 2009-10-13 2011-04-21 Unilever Plc Polymères colorants

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"OPTILAN BLAU MF-GL", 26 June 2009 (2009-06-26), http://www.clariant-msds.pl/, pages 1 - 6, XP055044167, Retrieved from the Internet <URL:http://www.clariant-msds.pl/karty/OPTILAN BLAU MF-GL sgr _3_260609_ R.pdf> [retrieved on 20121114] *

Also Published As

Publication number Publication date
KR20140041744A (ko) 2014-04-04
JP2014519543A (ja) 2014-08-14
TW201313840A (zh) 2013-04-01
EP2721113A1 (fr) 2014-04-23
BR112013032249A2 (pt) 2016-12-20
CN103619962A (zh) 2014-03-05
MX2013014769A (es) 2014-07-30

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