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WO1997027249A1 - Teintures diazoiques reactives heteropolyfonctionnelles - Google Patents

Teintures diazoiques reactives heteropolyfonctionnelles Download PDF

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Publication number
WO1997027249A1
WO1997027249A1 PCT/GB1996/003237 GB9603237W WO9727249A1 WO 1997027249 A1 WO1997027249 A1 WO 1997027249A1 GB 9603237 W GB9603237 W GB 9603237W WO 9727249 A1 WO9727249 A1 WO 9727249A1
Authority
WO
WIPO (PCT)
Prior art keywords
optionally substituted
compound
independently
formula
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.)
Ceased
Application number
PCT/GB1996/003237
Other languages
English (en)
Inventor
Andrew Hunter Morris Renfrew
Mark Kenworthy
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.)
Syngenta Ltd
Original Assignee
Zeneca 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 Zeneca Ltd filed Critical Zeneca Ltd
Priority to AU12042/97A priority Critical patent/AU1204297A/en
Priority to GB9811592A priority patent/GB2323369B/en
Publication of WO1997027249A1 publication Critical patent/WO1997027249A1/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
    • 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

Definitions

  • This invention relates to organic chemicals suitable for use as reactive dyes, to intermediate compounds therefor and to processes for their manufacture and use.
  • Reactive dyes have been known since the 1950's and are often applied to cellulosic substrates in a dyebath in conjunction with an alkali to assist covalent bond formation.
  • the dyebath is not completely exhausted of dye leaving some dye in the dyebath.
  • some dye only loosely adheres to the substrate and has to be washed at a later stage.
  • Unused or hydrolysed dye in the dyebath or washings must be disposed of and this is a major burden on dyehouses. Therefore there is a need for dyes which are exhausted efficiently from dyebaths and fix well to substrates thereby reducing effluent.
  • A is optionally substituted phenylene
  • B and E are each independently optionally substituted phenylene or optionally substituted naphthylene; D is a coupling component; each R 1 independently is H or optionally substituted alkyl;
  • X is a labile atom or group; and each Y independently is O or S.
  • the total number of sulpho groups in the compound of Formula (1) is form 2 to 6.
  • the optional substituents which may be present on A B, D, E and R 1 are preferably each independently selected from C ⁇ -alkyl, especially methyl; C M -alkoxy, especially methoxy; halo.especially Cl; nitro; amino; hydroxy; sulpho; cyano; carboxy; ureido; and C ⁇ -amido, especially acetamido.
  • ⁇ B and E are preferably each independently optionally substituted 1,3- or 1,4- phenylene.
  • D is preferably optionally substituted naphthylene, more preferably optionally substituted 2,6-, 2,7- or 2,8- naphthylene, especially optionally substituted naphthylene having a hydroxy group at the 1 -position of the naphthylene ring; optionally substituted phenylene, more preferably 1,3- or 1,4- phenylene; or an optionally substituted pyridonylene or pyrazolonylene group.
  • Each R 1 independently is preferably H or C M -alkyl, especially H or methyl.
  • Y is preferably O.
  • X is preferably a pyridinium group, especially 3- or 4- carboxy pyridinium; more preferably a halo atom, especially F or Cl, more especially Cl.
  • a preferred class of compounds according to the invention is of the Formula (2) or a salt thereof:
  • R 2 and R 3 are each independently H, S0 3 H, C M -alkyl (preferably methyl),
  • each R 4 independently is H, S0 3 H, C M -alkoxy, C ⁇ -alkyl or halo;
  • R 5 is H or SO 3 H
  • R ⁇ X and Y are as hereinbefore defined.
  • R 5 is H.
  • Compounds of the invention may be prepared by condensing compounds of Formula (3) and (4) wherein A, B, D, E, R 1 , X and Y are as hereinbefore defined:
  • condensation of the compounds of Formula (3) and (4) is performed in an aqueous medium, especially water.
  • the precise conditions will be chosen to prevent or limit side reactions such as hydrolysis of the dye.
  • a temperature in the range 0°C to 50°C is used.
  • Diazotisation conditions are well known in the art, for example treating an amine with NaN0 2 under acidic conditions at 0-5°C.
  • the compounds of Formula (1) can be isolated from the medium in which they have been prepared by conventional methods used for isolation of water-soluble dyes, e.g. by salting out followed by filtration and drying by spray drying the reaction mixture. If desired, stabilisers such as alkali metal hydrogen phosphates, polyphosphates or diluents such as sodium chloride or urea can be added.
  • the dyes may also be desalinated using techniques such as reverse osmosis and/or ultrafiltration to give formulations having high solubility in water.
  • formulae includes salts of the compounds, and in particular the alkali metal salts such as the sodium, potassium, lithium or mixed sodium lithium salt.
  • a further feature of the present invention provides a process for the coloration of a substrate by applying thereto a compound of Formula (1)or (2).
  • the compounds of Formula (1) can be applied to a wide variety of substrates, particularly those having -OH or -NH- groups, and are especially valuble as dyes for cellulosic materials such as cotton, jute, hemp and flax.
  • the compound is applied in conjunction with an acid binding agent, e.g. an alkali metal carbonate or bicarbonate, at a temperature of 120°C to 180°C.
  • an acid binding agent e.g. an alkali metal carbonate or bicarbonate
  • the dyes are preferably applied using standard pad-dry-bake methods and are characterised by very high fixation and high wash-fastness with little colour loss during wash-off. Generally few wash-off steps are required and little effluent is generated.
  • Stage b To a slurry of 4-amino-1,1 1 -azobenzene-3-sulphonic acid, 4 1 - sulphatoethylsulphonamide (44g, 0.02M) in ice water (300ml) was added concentrated hydrochloric acid (11 ml) followed by 2N NaN0 2 (11 ml). The mixture was stirred at 0- 5°C until diazotisation was complete and excess nitrous acid was destroyed by adding sulphamic acid. Sodium acetate was added to give a pH of 9.4 and the mixture was added to the product of stage a. NaHC0 3 was added to the mixture to pH6 and the mixture was stirred at pH6, 0-5°C for 2 hours. KCI (15% w/v) was added and the resultant precipitate filtered off, washed and dried.
  • stage b The product from stage b (10.98g, 7.4 x 10 "3 moles) was dissolved in water (200ml). 3-( ⁇ -sulphatoethylsulphonamido)aniline (5.0g, 0.017 mole) was added and the mixture stirred at room temperature and pH6.3 for 1 day. The solution was salted to 10% w/v with KCI and the resultant precipitate filtered-off, washed and dried to give the title product (12.1g) having a ⁇ max at 528nm.
  • the title product was applied to cotton by using the pad-dry-bake method and was found to have excellent fixation. After washing the wash liquors were essentially colourless.
  • Example 1 The general method of Example 1 may be repeated except that the components used in stage a), b) and c) are as shown in Table 1 below wherein,
  • Example 1 The method of Example 1 may be repeated except that in place of cyanuric chloride there is used cyanuric fluoride.
  • the chlorine atom in product of Examples 1 to 8 may be replaced by a 3-carboxy pyridinium group by heating the dyes (1 part at 80°C) with 3-carboxy pyridine (1.2 parts) in water for approximately 1 hour.
  • the resultant dye may be applied on cotton by the pad-dry-bake method.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

La présente invention concerne un composé de formule (1) et des sels de ce composé. A est le phénylène, éventuellement substitué; B et E sont chacun, de manière indépendante, du phénylène ou du naphtylène, tous deux éventuellement substitués; D est un constituant de couplage; chaque R1 est, de manière indépendante, H ou un alkyle éventuellement substitué; X est un atome ou un groupement labiles, et chaque Y est, de manière indépendante, O ou S. Ces composés sont utiles pour colorer des supports très divers, en particulier les supports cellulosiques par le procédé de fixage par foulardage-séchage.
PCT/GB1996/003237 1996-01-27 1996-12-24 Teintures diazoiques reactives heteropolyfonctionnelles Ceased WO1997027249A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU12042/97A AU1204297A (en) 1996-01-27 1996-12-24 Heteropolyfunctional reactive disaro dyes
GB9811592A GB2323369B (en) 1996-01-27 1996-12-24 Heteropolyfunctional reactive disaro dyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9601696.9 1996-01-27
GBGB9601696.9A GB9601696D0 (en) 1996-01-27 1996-01-27 Organic chemicals

Publications (1)

Publication Number Publication Date
WO1997027249A1 true WO1997027249A1 (fr) 1997-07-31

Family

ID=10787700

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1996/003237 Ceased WO1997027249A1 (fr) 1996-01-27 1996-12-24 Teintures diazoiques reactives heteropolyfonctionnelles

Country Status (3)

Country Link
AU (1) AU1204297A (fr)
GB (1) GB9601696D0 (fr)
WO (1) WO1997027249A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1041122A1 (fr) * 1999-03-30 2000-10-04 Ciba SC Holding AG Colorants réactifs, procédé pour leur Préparation et leur utilisation
US6451072B1 (en) 1999-03-30 2002-09-17 Ciba Specialty Chemicals Corporation Reactive dyes, process for their preparation and their use
CN102433028A (zh) * 2011-09-29 2012-05-02 天津德凯化工股份有限公司 一种偶氮类红色活性染料及其中间体
CN102876079A (zh) * 2012-09-20 2013-01-16 天津德凯化工股份有限公司 一种活性黑染料及其制备方法
WO2013189813A1 (fr) 2012-06-18 2013-12-27 Dystar Colours Distribution Gmbh Colorants réactifs, procédé de production et utilisation de ceux-ci

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1228601A (fr) * 1958-06-10 1960-08-31 Basf Ag Procédé pour la production de colorants azoïques
FR1256161A (fr) * 1960-03-04 1961-03-17 Ici Ltd Colorants azoïques réactifs pour matières textiles naturelles et artificielles
GB1118785A (en) * 1964-11-13 1968-07-03 Ici Ltd Water-soluble phthalocyanine reactive dyestuffs
FR1546109A (fr) * 1966-11-29 1968-11-15 Ici Ltd Nouveaux colorants anthraquinoniques réactifs solubles dans l'eau

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1228601A (fr) * 1958-06-10 1960-08-31 Basf Ag Procédé pour la production de colorants azoïques
FR1256161A (fr) * 1960-03-04 1961-03-17 Ici Ltd Colorants azoïques réactifs pour matières textiles naturelles et artificielles
GB1118785A (en) * 1964-11-13 1968-07-03 Ici Ltd Water-soluble phthalocyanine reactive dyestuffs
FR1546109A (fr) * 1966-11-29 1968-11-15 Ici Ltd Nouveaux colorants anthraquinoniques réactifs solubles dans l'eau

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1041122A1 (fr) * 1999-03-30 2000-10-04 Ciba SC Holding AG Colorants réactifs, procédé pour leur Préparation et leur utilisation
US6451072B1 (en) 1999-03-30 2002-09-17 Ciba Specialty Chemicals Corporation Reactive dyes, process for their preparation and their use
CN102433028A (zh) * 2011-09-29 2012-05-02 天津德凯化工股份有限公司 一种偶氮类红色活性染料及其中间体
WO2013189813A1 (fr) 2012-06-18 2013-12-27 Dystar Colours Distribution Gmbh Colorants réactifs, procédé de production et utilisation de ceux-ci
CN102876079A (zh) * 2012-09-20 2013-01-16 天津德凯化工股份有限公司 一种活性黑染料及其制备方法

Also Published As

Publication number Publication date
GB9601696D0 (en) 1996-03-27
AU1204297A (en) 1997-08-20

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