WO2002055611A1 - Teintures azoiques insolubles halogenees et sulfonees - Google Patents

Teintures azoiques insolubles halogenees et sulfonees Download PDF

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Publication number
WO2002055611A1
WO2002055611A1 PCT/US2002/000270 US0200270W WO02055611A1 WO 2002055611 A1 WO2002055611 A1 WO 2002055611A1 US 0200270 W US0200270 W US 0200270W WO 02055611 A1 WO02055611 A1 WO 02055611A1
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WO
WIPO (PCT)
Prior art keywords
chlorine
hydrogen
bromine
group
ring
Prior art date
Application number
PCT/US2002/000270
Other languages
English (en)
Inventor
David Anthony Akerman
John Anthony Taylor
Original Assignee
The Procter & Gamble Company
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 The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to EP02713365A priority Critical patent/EP1348009A1/fr
Priority to CA002429812A priority patent/CA2429812A1/fr
Priority to JP2002556669A priority patent/JP2004517985A/ja
Publication of WO2002055611A1 publication Critical patent/WO2002055611A1/fr
Priority to US10/614,591 priority patent/US20040111811A1/en

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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
    • 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
    • D06P1/38—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 reactive dyes
    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
    • C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
    • C09B62/4411—Azo dyes
    • C09B62/4415—Disazo or polyazo dyes
    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
    • C09B62/507—Azo dyes
    • C09B62/513—Disazo or polyazo dyes
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments

Definitions

  • the present invention relates to novel dyes, and fabrics and yarns dyed with them, which have improved fade resistance during washing with bleach-containing detergents.
  • a widely used fabric dye is the disazo compound CI Reactive Black 5 (also known as Everzol Black B) .
  • This compound is a compound of Formula 1
  • SES is an abbreviation for sulphato-ethane- sulphonyl .
  • SES is a reactive group which forms a vinyl sulphone under alkaline dyeing conditions .
  • the vinyl sulphone group then reacts with hydroxy or amino containing textile substrates with covalent bond formation, thus giving improved fastness.
  • the oxygen substituent in ring B and the adjacent hydrazo group can alternatively be written as a hydroxy group and an azo group .
  • CI Reactive Black B is the largest selling reactive dye. By varying the concentration of Reactive Black 5 and by blending it with other dyes various colours can be obtained. Very large volumes of Reactive Black 5 are used as a fabric or yarn dye.
  • CI Reactive Black 5 Despite the very wide acceptance of CI Reactive Black 5, it does suffer from a disadvantage in that fibres dyed with it tend to fade in colour when washed with detergents containing a peroxy bleach, such as a detergent containing a bleach activator such as N,N,N' ,N' -tetraacetylethylene diamine (TAED) and perborate or percarbonate . This fading is noticed primarily on lighter shades. Accordingly it would be desirable to be able to modify Reactive Black 5, and related dyes, in a simple and economic manner so as to maintain the desirable colour effects and cost effectiveness of the dyes whilst improving their fastness when washed with an aqueous detergent containing peroxy bleach.
  • a peroxy bleach such as a detergent containing a bleach activator such as N,N,N' ,N' -tetraacetylethylene diamine (TAED) and perborate or percarbonate .
  • TAED N,N,N' ,N'
  • the purpose of the substituents in the ortho position in ring A is to generate another hydroxy group in that ortho position, whereupon the two hydroxy groups can then complex heavy metals, such as copper. Accordingly, even though other substituents may initially be present in the ortho position in ring A, in actual use the substituent is another hydroxy group which can form the complex with a heavy metal .
  • Y is fluorine, chlorine or bromine and Z represents 1, 2 or 3 sulphonic-groups and/or 1 or 2 substituents selected from nitro, lower alkoxy, lower alkyl, carboxy, fluorine, chlorine or bromine.
  • the problem solved by these dyes is the problem of changes in shade in the presence of copper ions in the dye liquor.
  • the dyes are all said to give good dying properties and fastness similar to the dyes of the prior art, ie without the halogen Y. It . appears that the presence or absence of the halogen Y makes no difference to the resistance to fading when fabrics dyed with this dye are washed with detergents containing a peroxy bleach.
  • X is fluorine, chlorine, bromine or iodine
  • R is fluorine, chlorine, bromine, iodine, hydrogen or R 3
  • R 2 are the same or different and are H or R 3
  • R 3 substituents are the same or different and are selected from -SO 3 H, -N0 2 , a fibre reactive group or any moiety linked to the benzene ring by a carbon atom
  • n is 0, 1, 2 or 3
  • m is 0, 1, 2 or 3
  • water soluble salts thereof usually alkali metal salts especially sodium or potassium salts.
  • halogen in the 2 position of ring A as group X, and hydrogen or halogen in the 6 position as the group R 17 yields compounds which give improved fastness (especially of light shades) against peroxy-bleach containing wash liquors relative to compounds which do not have halogen in the 2 and 6 positions or halogen in the 2 position with the 6 position unsubstituted.
  • the invention follows from extensive research into the theories and the mechanisms by which fading may be caused of dyes such as CI Reactive Black 5 in the presence of peroxy containing aqueous detergent wash liquors. As a result of this we believe that the fading is due to simultaneous nucleophilic and electrophilic attacks on the C-0 bond at the 8" position and on the NH bond in the hydrazo group between rings A and B.
  • the 2 halo or 2 , 6 halo substitution in ring A suppresses both the electrophilic attack and the nucelophilic attack.
  • Preferred compounds are those in which X is bromine or chlorine and R 1 is hydrogen, bromine or chlorine. Chlorine is generally preferred. R is preferably hydrogen.
  • the groups R 2 are preferably hydrogen and/or S0 3 H and often both are hydrogen.
  • the S0 3 H groups in rings C and B are preferably in the 3" and 6" positions.
  • Preferred compounds have an SES group or other fibre reactive group in ring A and/or in ring D at a position meta or para to the azo group, and the sulphonic group in ring C is preferably at a position ortho to the azo group in ring C.
  • the preferred compounds are derivatives of Reactive Black 5 achieved solely by introducing halogen at the 2- position and optionally the 6-position in the ring A.
  • the groups R 3 can be selected individually from hydrogen, fibre-reactive groups, alkyl, alkoxy, acyla ino, cyano, -COOH, -COOR 4 where R 4 an esterifying group such as alkyl, -S0 3 H (or a salt) or -N0 2 .
  • the preferred fibre reactive group is SES but, in general, preferred fibre reactive groups can be defined as having the formula -S0 2 Y where Y is ⁇ -sulphatoethyl, ⁇ - chloroethyl, ⁇ -thiosulphatoethyl, vinyl, quaternary ammonium ethyl or ⁇ -acyloxyethyl where the acyl radical is the radical of an alkane carboxylic acid or of a benzoic acid or of a benzene sulphonic acid.
  • fibre reactive groups are the corresponding compounds in which the S0 2 group in -S0 2 Y is replaced by another electron withdrawing group such as - NHCO- .
  • Other fibre-reactive groups are heterocyclic groups having the Formulae 4 or 5, optionally linked to rings A or D through a -NH group:
  • a to e are halogen, especially fluorine or chlorine, or other atoms or groups which are readily displaced by nucleophilic species such as cellulosate, for instance -S0 2 CH 3 , -S0 3 " Na + , -N + R 3 (such as -N + Me 3 and compounds of formula 6
  • R 5 is H or COOH (meta or para) .
  • All these fibre-reactive groups may be selected in known manner from a wide range of electrophilic species which react with hydroxyl groups of hydroxyl-containing fibres such as cellulose (including cotton) and viscose or amino groups of fibres such as wool or polyamide (nylon) .
  • the compounds of the invention may be made by coupling appropriately substituted diazo components which provide rings A and D with an appropriate coupling component which provides rings B and C, for instance by the general method described in US 4,492,654.
  • the compounds can be used to dye suitable fibres, generally cotton, viscose or other cellulose fibres, nylon or wool fibres by conventional dyeing techniques. Dyeing may be conducted onto the fibres in freeform, generally as yarn, or in preformed fabric form, for instance a non-woven or, more usually, a woven or knitted fabric.
  • the fabric is generally of the type which would conventionally be laundered frequently using aqueous detergents containing a bleach, for instance towelling or clothing fabrics.
  • the manufacturer needs to make warranties as to its performance, and thus show the performance of the dye under standard conditions, such as under a standard aqueous detergent peroxy bleach wash.
  • the dye Once the dye has become accepted as an industry standard, it may no longer be necessary for the manufacturer to continue to show what the properties of the dye are since the customer will buy the dye knowing the previously published properties of it. Nevertheless that use of the dye by the customer is still associated with the original showing of the properties of the dye in an aqueous detergent containing peroxy bleach.
  • the invention is of particular value in all those situations where the customer needs a dye which has been shown to have good wash fastness when washed with an aqueous detergent containing a peroxy bleach such as perborate or percarbonate .
  • the industry standard is usually an aqueous detergent containing a perborate bleach. Any showing utilising such a detergent, or any other detergent which is indicative of fastness to peroxy bleaches, can be relied upon in the invention.
  • MCT is the compound of formula 5 where d is CI and e is amine
  • MFT is the compound of formula 5 in which d is fluorine and e is amine
  • DCT is the compound of formula 5 in which d and e are both chlorine
  • Pyr is the compound of formula 4 where c is hydrogen or chlorine and one or both of a and b are fluorine or chlorine.
  • the compound of Example 1 was dyed by exhaust dyeing.
  • a wash liquor was prepared by dispensing 10 grams of ECE detergent powder with 1.8 grams TAED at 100% and 12 grams sodium perborate per litre of water. These ingredients were dispersed vigorously at 20°C for 10 minutes. Specimens of dyed fabric measuring 5 by 10 centimetres which had been weighed were placed in a dyeing machine together with the wash liquor to provide a liquor to goods ratio of 100 to 1. The temperature was raised from 20°C to 60°C in 22 minutes and the test continued at 60°C for a further 30 minutes. The specimens were removed at the end of the wash and placed in a 4 litre beaker half filled with water. The specimens were gently agitated and then rinsed for one minute. The specimens were placed under a cold running tap for 10 minutes and squeezed to remove excess water .
  • Example 1 After air drying, the specimens were assessed for colour change using a spectraflash 600 spectrophotometer against unexposed standards. As a comparison, CI Reaction Black 5 was also tested in a similar manner on a similar fabric.
  • the compound of Example 1 passed the UK-TO test unambiguously at depths of shade k/s equalling 13 and k/s 26 and showed a change in shade (DE CIE lab) of 1.5 and 2.1 units respectively.
  • the compound of formula 3 in which X is chlorine and R x and both R 2 groups are hydrogen gives better performance than the compound in which X and R x and one of the R 2 groups is hydrogen and the other R 2 group is chlorine.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Detergent Compositions (AREA)
  • Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)

Abstract

L'invention concerne de nouvelles teintures pour fibres présentant une plus grande résistance à la décoloration lorsqu'elles sont lavées à l'aide de liqueurs de lavage peroxy aqueuses. Les nouvelles teintures sont représentées par la formule suivante dans laquelle X est du fluor, du chlore, du brome ou de l'iode; R1 est du fluor, du chlore, du brome, de l'iode, de l'hydrogène ou R3; les substituants de R3 sont identiques ou différents et sont sélectionnés parmi SO3H, -NO2, un groupe de réaction aux fibres ou un quelconque fragment lié au noyau de benzène par un atome de carbone; n est 0, 1, 2 ou 3; m est 0, 1, 2 ou 3.
PCT/US2002/000270 2001-01-05 2002-01-04 Teintures azoiques insolubles halogenees et sulfonees WO2002055611A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP02713365A EP1348009A1 (fr) 2001-01-05 2002-01-04 Teintures azoiques insolubles halogenees et sulfonees
CA002429812A CA2429812A1 (fr) 2001-01-05 2002-01-04 Teintures azoiques insolubles halogenees et sulfonees
JP2002556669A JP2004517985A (ja) 2001-01-05 2002-01-04 ハロゲン化およびスルホン化アゾ染料
US10/614,591 US20040111811A1 (en) 2001-01-05 2003-07-07 Halogenated and sulfonated azodyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0100192.4 2001-01-05
GB0100192A GB2370842A (en) 2001-01-05 2001-01-05 Optionally reactive 1-amino-2-(phenylazo)-7-(2-halophenylazo)-8-hydroxynaphthalene-disulphonic acid derivatives with improved resistance to peroxy wash fading

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/614,591 Continuation US20040111811A1 (en) 2001-01-05 2003-07-07 Halogenated and sulfonated azodyes

Publications (1)

Publication Number Publication Date
WO2002055611A1 true WO2002055611A1 (fr) 2002-07-18

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ID=9906252

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2002/000270 WO2002055611A1 (fr) 2001-01-05 2002-01-04 Teintures azoiques insolubles halogenees et sulfonees

Country Status (6)

Country Link
EP (1) EP1348009A1 (fr)
JP (1) JP2004517985A (fr)
CN (1) CN1484678A (fr)
CA (1) CA2429812A1 (fr)
GB (1) GB2370842A (fr)
WO (1) WO2002055611A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0031099A2 (fr) * 1979-12-21 1981-07-01 BASF Aktiengesellschaft Composés avec des restes réactifs et leur utilisation pour la teinture des fibres
EP0048355A1 (fr) * 1980-09-06 1982-03-31 Hoechst Aktiengesellschaft Composés bis-azoiques solubles dans l'eau, procédé pour leur préparation et leur utilisation comme colorants
EP0063276A2 (fr) * 1981-04-07 1982-10-27 Hoechst Aktiengesellschaft Procédé de préparation de composés disazoiques
US4492654A (en) * 1980-07-05 1985-01-08 Hoechst Aktiengesellschaft Water-soluble azo compounds, a process for their preparation and their use as dyes
JPH0532908A (ja) * 1990-08-28 1993-02-09 Sumitomo Chem Co Ltd ビスアゾ化合物及びそれを用いて繊維材料を染色又は捺染する方法
EP1046677A1 (fr) * 1999-04-22 2000-10-25 DyStar Textilfarben GmbH & Co. Deutschland KG Composés disazoiques solubles dans l'eau dérivés de diazos contenant un groupe arylcarbonamide, procédé pour leur préparation et leur utilisation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL137328B2 (en) * 1984-10-04 1986-05-31 Method of manufacture of novel trisazo dyes
JPS6286070A (ja) * 1985-10-11 1987-04-20 Ricoh Co Ltd 水性インク組成物
JPS6286072A (ja) * 1985-10-11 1987-04-20 Ricoh Co Ltd 水性インク組成物
JP2517596B2 (ja) * 1987-05-21 1996-07-24 株式会社リコー 水性インク組成物
DE3906778A1 (de) * 1989-03-03 1990-09-06 Hoechst Ag Wasserloesliche faserreaktive farbstoffe, verfahren zu ihrer herstellung und ihre verwendung

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0031099A2 (fr) * 1979-12-21 1981-07-01 BASF Aktiengesellschaft Composés avec des restes réactifs et leur utilisation pour la teinture des fibres
US4492654A (en) * 1980-07-05 1985-01-08 Hoechst Aktiengesellschaft Water-soluble azo compounds, a process for their preparation and their use as dyes
EP0048355A1 (fr) * 1980-09-06 1982-03-31 Hoechst Aktiengesellschaft Composés bis-azoiques solubles dans l'eau, procédé pour leur préparation et leur utilisation comme colorants
EP0063276A2 (fr) * 1981-04-07 1982-10-27 Hoechst Aktiengesellschaft Procédé de préparation de composés disazoiques
JPH0532908A (ja) * 1990-08-28 1993-02-09 Sumitomo Chem Co Ltd ビスアゾ化合物及びそれを用いて繊維材料を染色又は捺染する方法
EP1046677A1 (fr) * 1999-04-22 2000-10-25 DyStar Textilfarben GmbH & Co. Deutschland KG Composés disazoiques solubles dans l'eau dérivés de diazos contenant un groupe arylcarbonamide, procédé pour leur préparation et leur utilisation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 017, no. 327 (C - 1073) 22 June 1993 (1993-06-22) *

Also Published As

Publication number Publication date
GB2370842A (en) 2002-07-10
EP1348009A1 (fr) 2003-10-01
JP2004517985A (ja) 2004-06-17
CN1484678A (zh) 2004-03-24
CA2429812A1 (fr) 2002-07-18
GB0100192D0 (en) 2001-02-14

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