GB1122389A - Reactive dyestuffs containing a free or salified acid group and a halopyridine residue - Google Patents

Reactive dyestuffs containing a free or salified acid group and a halopyridine residue

Info

Publication number
GB1122389A
GB1122389A GB3367365A GB3367365A GB1122389A GB 1122389 A GB1122389 A GB 1122389A GB 3367365 A GB3367365 A GB 3367365A GB 3367365 A GB3367365 A GB 3367365A GB 1122389 A GB1122389 A GB 1122389A
Authority
GB
United Kingdom
Prior art keywords
acid
nitro
pyridine
salt
prepared
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
Application number
GB3367365A
Inventor
Marice Rene Jean Vallette
Jean Andre Paul Kienzle
Andre Albert Paul Simonnet
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.)
Kuhlmann SA
Original Assignee
Kuhlmann SA
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 Kuhlmann SA filed Critical Kuhlmann SA
Publication of GB1122389A publication Critical patent/GB1122389A/en
Expired legal-status Critical Current

Links

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
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/36—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to some other heterocyclic ring
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • 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
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/343—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a five membered ring

Landscapes

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

Abstract

The invention comprises dyestuffs of the formula <FORM:1122389/C4-C5/1> where A is the residue of a dyestuff molecule containing a free or solified acid group, one X is halogen and the others are H, OH, CH3 or halogen, Y is -NRCO-, -NRSO2- or -N = N-, Z is H, alkyl, hydroxyalkyl, -COOR, <FORM:1122389/C4-C5/2> -CONalkylene, -CONalkanetriyl-OH, -CN, -SO3H, <FORM:1122389/C4-C5/3> or NO2 R and R1 are H, alkyl or hydroxyalky and n is 1 or 2. The compounds wherein R is -NRCO- or -NRSO2- may be prepared by reacting together <FORM:1122389/C4-C5/4> and A(NHR)n where W1 is SO2 or CO. The compounds wherein R is -N = N- may be prepared by diazotization and coupling of appropriate components.ALSO:2 - Hydroxy - 5 - nitro - pyridine - 3 -sulphonic acid is prepared from 2 - hydroxy - 5 nitro - pyridine and chlorosulphonic acid; this acid is converted to the Ca salt with CaCO3 and then to the Na salt with Na2CO3; this Na salt is treated with POCl3 to give 2 - chloro - 5 - nitro - pyridine - 3 - sulphonyl chloride; this chloride is converted into the Na salt of 2-chloro - 5 - nitro - pyridine - 3 - sulphonate by Na2CO3 and this nitro compound is reduced to the corresponding amine by the Bechamp method using Fe powder. 2-Aminopyridine is treated with chlorosulphonic acid to give a mixture of 2-aminopyridine 3- and 5-sulphonic acid, the amino groups of which are converted to hydroxy groups via the diazo compounds and the resulting mixture when treated with PCl5 gives a mixture of 2-chloropyridine-3- and 5-sulphonychloride. 2 - Chloropyridine - 5 - sulphonylchloride may also be prepared from N - methyl - 2 - pyridone - 5 - sulphonic acid. 3,5 - Dichlorosulphonyl - 2 - chloropyridine is obtained by treating the mixture of 2-hydroxypyridine 3- and 5-sulphonic acid with chlorosulphonic acid.
GB3367365A 1964-08-08 1965-08-06 Reactive dyestuffs containing a free or salified acid group and a halopyridine residue Expired GB1122389A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR984647A FR1420406A (en) 1964-08-08 1964-08-08 New reactive dyes, their applications and intermediates for their preparation

Publications (1)

Publication Number Publication Date
GB1122389A true GB1122389A (en) 1968-08-07

Family

ID=8836370

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3367365A Expired GB1122389A (en) 1964-08-08 1965-08-06 Reactive dyestuffs containing a free or salified acid group and a halopyridine residue

Country Status (6)

Country Link
BE (1) BE667565A (en)
CH (1) CH456527A (en)
DE (1) DE1469689A1 (en)
FR (1) FR1420406A (en)
GB (1) GB1122389A (en)
NL (2) NL6510350A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1948354A1 (en) * 1968-09-24 1970-04-23 Ici Ltd Reactive dyes
US4039523A (en) * 1970-12-22 1977-08-02 Ciba-Geigy Ag 3-Sulfoalkyl-6-hydroxy-pyrid-(2)-one-containing azo dyestuffs
US4092308A (en) * 1972-10-05 1978-05-30 Ciba-Geigy Corporation 4-Sulphomethyl substituted hydroxypyridone azo dyestuffs
US4213899A (en) * 1977-05-27 1980-07-22 Imperial Chemical Industries Limited Reactive dyestuffs containing chlorine or fluorine substituents and one or more pyridine radicals linked to the dyestuff at the 2-, 4- or 6-position
US5373094A (en) * 1992-06-25 1994-12-13 Zeneca Limited Reactive dyes containing a 2,6-difluoro-3,5-dichloropyridine group

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1350602A (en) * 1970-07-10 1974-04-18 Ici Ltd Azo dyestuffs
PL197843B1 (en) 1997-04-28 2008-05-30 Encysive Pharmaceuticals Inc Sulphonamides for treating endothelin-involving disorders
DE19918021C1 (en) 1999-04-21 2000-06-29 Ruetgers Organics Gmbh Preparation of chlorinated pyridine sulfonic acid chloride derivatives from hydroxypyridine sulfonic acids and phosphorus trichloride/chlorine gas; useful as intermediates for drugs, e.g. torasemide

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1948354A1 (en) * 1968-09-24 1970-04-23 Ici Ltd Reactive dyes
US4039523A (en) * 1970-12-22 1977-08-02 Ciba-Geigy Ag 3-Sulfoalkyl-6-hydroxy-pyrid-(2)-one-containing azo dyestuffs
US4092308A (en) * 1972-10-05 1978-05-30 Ciba-Geigy Corporation 4-Sulphomethyl substituted hydroxypyridone azo dyestuffs
US4213899A (en) * 1977-05-27 1980-07-22 Imperial Chemical Industries Limited Reactive dyestuffs containing chlorine or fluorine substituents and one or more pyridine radicals linked to the dyestuff at the 2-, 4- or 6-position
US5373094A (en) * 1992-06-25 1994-12-13 Zeneca Limited Reactive dyes containing a 2,6-difluoro-3,5-dichloropyridine group

Also Published As

Publication number Publication date
NL128672C (en)
DE1469689A1 (en) 1968-12-19
CH456527A (en) 1968-07-31
CH1037365A4 (en) 1968-02-15
BE667565A (en) 1966-01-28
FR1420406A (en) 1965-12-10
NL6510350A (en) 1966-02-09

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