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GB1580660A - Disazo dyestuffs containing 2-amino-8-hydroxy-naphthalene-6-sulphonic acid - Google Patents

Disazo dyestuffs containing 2-amino-8-hydroxy-naphthalene-6-sulphonic acid Download PDF

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GB1580660A
GB1580660A GB30858/77A GB3085877A GB1580660A GB 1580660 A GB1580660 A GB 1580660A GB 30858/77 A GB30858/77 A GB 30858/77A GB 3085877 A GB3085877 A GB 3085877A GB 1580660 A GB1580660 A GB 1580660A
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compound
formula
mixture according
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Sandoz AG
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    • 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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups

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

(54) DISAZO DYESTUFFS CONTAINING 2-AMINO-8 HYDROXY NAPHTHALENE-6-SULPHONIC ACID (71) We, SANDOZ LTD., of 35 Lichtstrasse, 4002 Basle, Switzerland, a Swiss Body Corporate, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: The present invention relates to azo compounds and mixtures thereof, their production and use.
Accordingly, the present invention provides azo compounds of formula I,
in which D is the radical of a diazo component of formula (a), (b) or (c),
in which R, is trifluoromethyl, -COOM1, -COOR2; or a group of formulae -NHR3, -NR3R4 or -NR5COR6 in a position meta or para to the azo group; ring A being optionally further substituted by a total of up to two further substituents selected from halogen, (C,~4)alkyl (preferably methyl), (C,~4)alkoxy (preferably methoxy) and trifluoromethyl (only one further trifluoromethyl group), R2 is (C,~,2)alkyl, each of R3 and R4, independently, is (C,~8) alkyl, R5 is hydrogen or (C,~4)alkyl, R6 is (Ct )alkyl, (C,~8)alkoxy or (C,~8)alkyl mono-substituted by chlorine or methoxy, B is a divalent radical of the 1,4-phenylene, 1,4-naphthylene or 1,2,3,4-tetrahydronaphthylene-5,8 series, and each of M and M,, independently, is hydrogen or an equivalent of a non-chromophoric cation, with the proviso that the molecule contains a single --SO3M group, and mixtures thereof, which compounds and mixtures are useful as anionic dyestuffs.
The alkyl radicals as R2, R3, R4, R5 and R6 may be straight- or branched-chain.
R2 is preferably (C,~8)alkyl. More preferably, R2 is R2, where R2 is (C,~4)alkyl.
Each of R3 and R4, independently, is preferably (C,~4)alkyl, more preferably R3 and R4 are R3 and R4,, respectively, where each of R3 and R4, independently, is methyl or ethyl, especially methyl.
Any alkyl as R5 is preferably methyl. Preferably, R is Rss where R'5 is hydrogen or methyl, especially hydrogen. 5 5, where R5 is Any unsubstituted alkyl as R6 is preferably a (C1-4)alkyl, more preferably methyl or ethyl, especially methyl. Any substituted alkyl as R6 is preferably wchloro- or methoxy-substituted (C,~3)alkyl. Any alkoxy group as R6 is preferably (C,~4)alkoxy, with methoxy being most preferred.
R6 is preferably R6', where R'8 is (C,~4)alkyl, w-chloro- or methoxy-substituted (C,~3)alkyl or (C1-4)alkoxy. More preferably Re is RN8, where R'8 is methyl, ethyl, methoxy, 2-methoxyethyl or 3-methoxypropyl. Most preferably, Re is R8", where R6''' is methyl or methoxy, with methyl being especially preferred.
R, is preferably RI, where R1' is trifluoromethyl, -COOR2, -NHR3, -NR3,R4' or-NR5'COR6'. More preferably R, is R;', where R"1 is -COOR; or NR5COR8'. Most preferably, R, is R," where R," is NR5,CORe"' with -NHCOCH3 being especially preferred.
Preferably any halogen on ring A is chlorine or bromine, with chlorine being most preferred.
The ring A is preferably further unsubstituted or further substituted by a total of up to two substituents selected from chlorine, methyl and methoxy.
Where the ring A bears one substituent in addition to R1, the 2 substituents are preferably in the 2,4-, 2,5- and 3,4-positions, with the 3,4-positions being especially preferred.
Where the ring A bears two substituents in addition to R1, the three substituents are preferably in the 2,3,5-, 2,4,5- or 2,4,6-positions, with the 2,4,5- and 2,4,6-positions being most preferred.
Preferably the group (a) is (a1),
wherein the ring A is further unsubstituted or further substituted by a total of up to two substituents selected from the group consisting of halogen, (C1-4)alkyl, (C,~4)alkoxy and trifluoromethyl (only one trifluoromethyl), with the substituents chlorine, methyl and methoxy being especially preferred. More preferably R, and R"1 More preferably (a) is (a2),
Wherein R, is hydrogen, chlorine, methyl or methoxy, especially hydrogen. In (a2) most preferably R7 is hydrogen and R;" is -NHCOCM3, such group being designated as (a ) hereinafter.
D is preferably (a,) or (b), more preferably (a2), with the group (a3) being most preferred.
B is preferably 1,4-naphthylene, 1,2,3,4-tetrahydronaphthylene-5,8, or a group of formula (d),
in which each of R8 and R9, independently, is hydrogen, (C1 4)alkyl or (C1 4)alkoxy.
Any alkyl as R8 and/or R9 is preferably methyl or ethyl, most preferably methyl.
Any alkoxy as Re and/or R9 is preferably methoxy or ethoxy, most preferably methoxy.
R8 is preferably Rg, where R8 is methyl, methoxy or ethoxy, most preferably methoxy.
R9 is preferably R9, where R9 is hydrogen, methyl, methoxy or ethoxy, most preferably R9 is Rug', where R9' is methyl or methoxy.
Preferably, the group (d) is (d1), where (d1) is a group of formula (d) where R8 is R8 and R9 is R9, more preferably (d) is (d2), where (d2) is (d) wherein R8 is methoxy and R9 is R9', preferably methoxy.
B is preferably 1,4-naphthylene or a group of formula (d), with (d) being especially preferred. More preferably, B is a group of formula (d1), most preferably (d2) Preferred compounds of formula I are those in which D is a group of formula (a) or (b) and B is a group of formula (d) or l,4-naphthylene.
More preferred compounds of formula I are those where D is a group of formula (a1) (preferably where R1 is R;') and B is (d) or is 1,4-naphthylene; of these, those compounds where D is a group of formula (a2) are even more preferred. Most preferred compounds are those wherein D is (a3) and B is (2).
The non-chromophoric cations as M and M1, independently, may be any one of those common the chemistry of anionic dyestuffs. Preferably each M and M1 independently, is hydrogen, an alkali metal cation, such as lithium, sodium or potassium, an unsubstituted, lower alkyl substituted or a hydroxyalkyl substitutedammonium ion of formula Ne(R10)4 in which each R,,, independently, is hydrogen, (C,~3)alkyl or 2- 3- or 4-hydroxy(C,~4)alkyl. Examples of such ammonium ions are ammonium, triethylammonium, mono-, di-, tri- or tetramethylammonium, mono-, di- or triethanolammonium or mono-, di- or triisopropanolammonium. Preferably M and M, are identical. Alkali metal cations are the preferred cations.
It will be appreciated that the substituted ammonium cation should not contain groups which would cause stability or steric problems, for example tetraalkanolammonium.
The present invention further provides a process for the production of compounds of formula I, or a mixture thereof, comprising coupling the diazo derivative of an amine of formula II, D-N=N-B-NH2 II or a mixture thereof with a compound of formula III,
or a mixture thereof.
The coupling reaction is carried out in acid medium, preferably at a pH value of from 3 to 4.5, in accordance with conventional methods.
Diazotization of the compounds of formula II may be carried out in accordance with known methods.
The compounds of formula II are either known or may be prepared in accordance with known methods by coupling the diazo derivative of an amine D-NH2 with a compound of B-NH2 in acid medium.
The compounds of formula III are known.
In general, as a result of the process of production, the compounds of formula I are obtained in salt form, usually in the sodium or potassium salt form and may be isolated as such from the reaction mixture in accordance with known methods.
However, they may also be isolated in the form of free acids by adding acid to the reaction mixture. The compounds may be employed for dyeing as such or may be converted into the salt form by the addition of bases such as hydroxides, carbonates, bicarbonates or acetates.
The compounds of formula I and mixtures thereof in the free acid or salt form are useful for dyeing or printing anionic dyable substrates. Examples of suitable substrates are natural and synthetic polyamide fibres, basic modified polyolefins, polyurethanes and leather. Preferred substrates are fibres of natural and synthetic polyamides such as wool, silk and especially nylon. Dyeing may be carried out in accordance with known methods, especially in accordance with pad dyeing or preferably exhaust dyeing methods. The dyestuffs of formula I and mixtures thereof exhaust from a neutral dyebath.
The dyestuffs according to the present invention are well soluble in water and build up well. The dyeings possess notable wet fastness for example wash- and sweatfastness, notable rubbing fastness and lightfastness. The dyestuffs according to the present invention combine well with other neutral-exhausting dyestuffs, the advantages such as build-up and fastnesses being retained.
The dyestuffs according to the present invention may be employed as such or may be used in the form of liquid or solid preparations. The liquid and solid preparations may be formed in accordance with conventional methods, for example by dissolving in suitable solvents, optionally with the addition of conventional additives such as stabilizers and/or dissolving agents for example, urea with subsequent grinding or granulating. Such preparations may be obtained in accordance with the procedure described in French Patents 1,572,630 and 1,581,900.
Further, the mixtures according to the present invention may be made up into preparations which are dispersable in cold water. for the preparation of such dispersions the dye mixture may be ground wet or dry to a particle size of less than 20 u, preferably 1--5 , in the presence of one or more conventional anionic dispersing agents and optionally in the presence of a non-ionic dispersing agent, with or without subsequent spray drying. The preparations so obtained are finely dispersed in cold water and are thus easy to handle.
The following Examples futher serve to illustrate the invention. In the Examples all parts are by weight and all temperatures are in degrees Centigrade.
Example I 15 parts of 4-aminoacetanilide are diazotised with 24 parts of concentrated hydrochloric acid and 7.0 parts of sodium nitrite in conventional manner. The excess nitrite is decomposed with amidosulphonic acid. 15.3 parts of l-amino-2,5- dimethoxybenzene are entered into 80 parts of water at 600, then dissolved by adding 10 parts of concentrated hydrochloric acid and cooled to 04 with ice.
The above solution of the diazotised 4-aminoacetanilide is added to this solution over the course of half an hour. The pH value is kept at 3.0 to 3.5 by the addtion of sodium acetate. Stirring takes place for 2 hours at 04", and then stirring is continued for a futher 16 hours at room temperature. The precipitated dyestuff is filtered and washed with a 5% hydrochloric acid solution.
The paste of the aminomonoazo dyestuff is dissolved at 800 with 70 parts water and 120 parts of glacial acetic acid then 20 parts of concentrated hydrochloric acid are added and the temperature is set at 040 by adding ice. An aqueous solution of 8.0 parts of sodium nitrite is passed in and stirred for 2 hours; the excess nitrite is subsequently decomposed with amidosulphonic acid. 23.9 Parts of 2-amino-8hydroxynaphthalene-6-sulphonic acid are stirred with 100 parts of water, and dissolved by adding about 12 parts of 30% caustic soda. This solution is added over the course of one hour to the above diazomonoazo solution, whereby the pH is kept at 3.54.0 by adding sodium acetate. The reaction mixture is stirred for a further 16 hours at 00, then set at a pH of 8.5 with caustic soda and stirred at room temperature for 2 hours.The precipitated dyestuff is filtered at this temperature, washed to neutral with a 5% sodium chloride solution and dried. It corresponds to formula
and dyes natural and synthetic polyamide fibres in dark blue shades.The dyeings have notable wet and light fastness.
Further compounds of general formula Ia which may be produced in analogous manner to the above procedure are given in Table 1.
The dyestuffs of Examples 2-5, 7, 8 and 10-34 give dyings of dark blue shades on polyamide fibre, the dyestuffs of Examples 6 and 9 give dyeings of violet shades. The dyeings obtained have comparable properties with the dyeings obtained with the dyestuff of Example 1.
TABLE 1
Example No. R1 (position) R, (position) R8 R9 2 NHCOOCH3 (4) H SOCH3 CH3 3 NHCOOCH3 (3) H do. do. 4 do. H do. OCH3 5 NHCOCH3 (4) H do. CH3 6 do. H CH3 do. 7 NHCOCH3 (3) H OCH3 OCH3 8 do. H do. CH3 9 do. H CH3 do. 10 do. H OCH3 H 11 do. CH3 (4) do. OCH3 12 do. Cl (4) do. do. 13 N(CH3)COCH3 (4) H do. do. 14 N(CH3)COCH3 (3) H do. do. 15 NHCOCH2CI (4) H do. CH3 16 do. H do. OCH3 17 NHCOCH2Cl (3) H do. do. 18 COOC2Hs (2) H do. do. 19 COOC2H5 (4) H do. do. 20 COOnC4H9 (4) H do. H 21 CF3 (3) H do. OCH3
TABLE 1 (continued)
Example No. R1 (position) R, (position) R, 22 CF3 (2) Cl (5) do. CH3 23 NHCOOC2Hs (3) H do. H 24 NHCOOC2Hs (4) H do. OCH3 25 NHCOC2Hs (4) H OCH3 CH3 26 NHCOC2Hs (3) H do. do.
27 COOnC4H9 (4) H do. OCHa 28 NHCOOCH2CH2OCH3 (4) H do. CH3 29 NHCOOCH2CH2OCH3 (3) H do. H 30 NHCOO(CH2)30CH3 (4) H H H 31 NHCH 3 - (4) H OCH3 OCH3 32 N(C2H3Y2 (4) H do. do.
33 N(CH3)COCH3 (4) H do. H 34 NHCOCH3 (3) CH3 (4) do. CH3 Further compounds of formula I which correspond to the general formula Ib,
and which may be prepared in analogous manner to the procedure described in Example I are given in Table 2. the dyes of Examples 35--42 and 4446 give dyeings of a dark blue shade on polyamide fibres and the dyestuff of Example 43 gives dyeings of violet shades on polyamide fibres. The dyeings obtained exhibit similar properties to those of the dyeings obtained with the compound of Example 1.
Table 2
Example D B No.
35 CH3CONH e t 36 0 do.
NHCOCH3 37 CH3CONH 38 t do.
NHCOCH3 39 + t NHCocH 40 who3.
CH3 OCH 41 Q.
OCH3 42 OCH3 43 do.
44 > + COOC2H5 O 45 bo.
N - COCH3 CR3 033 do.
CR3 Application Example A 100 parts of pre-wetted nylon cloth (nylon 66) are entered at 400 into a dye bath consisting of 4000 parts of water, 10 parts of anhydrous sodium sulphate and 2 parts of the dyestuff from Example 1.
The dye liquor is heated over the course of 30 minutes to boiling temperature, kept at this temperature for I hour, then 4 parts of glacial acetic acid are added thereto and dyeing is completed by heating for a further 30 minutes at boiling temperature. During dyeing, the water that evaporates is continuously replaced.
The dark-blue dyed nylon cloth is then removed from the liquor, rinsed with water and dried. Wool may also be dyed by the same process.
Dyeings may be made in the same manner using the dyestuffs from Examples 246, or mixtures thereof.
The dyeings have notable wet and light fastness.
Application Example B Polyamide is printed with a printing paste containing: 30 parts dyestuff of Example 7 50 parts urea 50 parts dissolving agent (e.g. thiodiethylene glycol) 290 parts water 500 parts suitable thickening agent (e.g. based on locus bean gum) 20 parts acid donating agent (e.g. ammonium tartrate) 60 parts thio urea The printed textile goods are steamed for 40 minutes at 1020 (saturated steam), then rinsed with cold water, subsequently washed at 600 with a dilute solution of a conventional detergent and rinsed again with cold water. A dark-blue print having notable light and wet fastness is obtained.
In analogous manner printing pastes may be made employing the dyestuffs of Examples 1--6 or 846 or mixtures of dyestuffs of Examples 146, such pastes may be employed for printing in accordance with the above given procedure.
WHAT WE CLAIM IS: 1. An azo compound of formula I,
in which D is the radical of a diazo component of formula (a), (b) or (c),
in which R, is trifluoromethyl, -COOM1, -COOR2; or a group of formulae -NHR3, -NR3R4 or -NR5COR6 in a position meta or para to the azo group; ring A being optionally further substituted by a total of up to two further substituents selected from halogen, (C,~4)alkyl, (C1~4)alkoxy and trifluoromethyl (only one further trifluoromethyl group, R2 is (C,~12)alkyl, each of Ra and R4, independently, is (C1 8) alkyl, R5 is hydrogen or (C14)alkyl, R6 is (C16)alkyl, (C1 s)alkoxy or (C,~8)alkyl mono-substituted by chlorine or methoxy, B is a divalent radical of the 1,4-phenylene, 1,4-naphthylene or 1,2,3,4-tetrahydronaphthylene-5,8 series, and each of M and M1,
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (39)

  1. **WARNING** start of CLMS field may overlap end of DESC **.
    Application Example A
    100 parts of pre-wetted nylon cloth (nylon 66) are entered at 400 into a dye bath consisting of 4000 parts of water, 10 parts of anhydrous sodium sulphate and 2 parts of the dyestuff from Example 1.
    The dye liquor is heated over the course of 30 minutes to boiling temperature, kept at this temperature for I hour, then 4 parts of glacial acetic acid are added thereto and dyeing is completed by heating for a further 30 minutes at boiling temperature. During dyeing, the water that evaporates is continuously replaced.
    The dark-blue dyed nylon cloth is then removed from the liquor, rinsed with water and dried. Wool may also be dyed by the same process.
    Dyeings may be made in the same manner using the dyestuffs from Examples 246, or mixtures thereof.
    The dyeings have notable wet and light fastness.
    Application Example B Polyamide is printed with a printing paste containing: 30 parts dyestuff of Example 7 50 parts urea 50 parts dissolving agent (e.g. thiodiethylene glycol) 290 parts water 500 parts suitable thickening agent (e.g. based on locus bean gum) 20 parts acid donating agent (e.g. ammonium tartrate) 60 parts thio urea The printed textile goods are steamed for 40 minutes at 1020 (saturated steam), then rinsed with cold water, subsequently washed at 600 with a dilute solution of a conventional detergent and rinsed again with cold water. A dark-blue print having notable light and wet fastness is obtained.
    In analogous manner printing pastes may be made employing the dyestuffs of Examples 1--6 or 846 or mixtures of dyestuffs of Examples 146, such pastes may be employed for printing in accordance with the above given procedure.
    WHAT WE CLAIM IS: 1. An azo compound of formula I,
    in which D is the radical of a diazo component of formula (a), (b) or (c),
    in which R, is trifluoromethyl, -COOM1, -COOR2; or a group of formulae -NHR3, -NR3R4 or -NR5COR6 in a position meta or para to the azo group; ring A being optionally further substituted by a total of up to two further substituents selected from halogen, (C,~4)alkyl, (C1~4)alkoxy and trifluoromethyl (only one further trifluoromethyl group, R2 is (C,~12)alkyl, each of Ra and R4, independently, is (C1 8) alkyl, R5 is hydrogen or (C14)alkyl, R6 is (C16)alkyl, (C1 s)alkoxy or (C,~8)alkyl mono-substituted by chlorine or methoxy, B is a divalent radical of the 1,4-phenylene, 1,4-naphthylene or 1,2,3,4-tetrahydronaphthylene-5,8 series, and each of M and M1,
    independently, is hydrogen or an equivalent of a non-chromophoric cation, with the proviso that the molecule contains a single -SO3M group, or mixtures thereof.
  2. 2. A compound or mixture according to Claim 1, in which R2 is (C,~8)alkyl.
  3. 3. A compound or mixture according to Claim I or Claim 2, in which each of R3 and R4 independently, is (C1-4)alkyl.
  4. 4. A compound or mixture according to any one of Claims 1 to 3, in which R6 is (C14)alkyl, (C1~4)alkoxy or (C1-3)alkyl monosubstituted by chlorine or methoxy.
  5. 5. A copmpound or mixture according to any one of Claims 1 to 4, in which R2 is R2 where R2 is (C14)alkyl.
  6. 6. A compound or mixture according to any one of Claims í to 5, in which R3 and R4 are 3 and R4 where each of R3 and R4, independently, is methyl or ethyl.
  7. 7. A compound or mixture according to any one of Claims I to 6, in which R5 is R5 where R5 is hydrogen or methyl.
  8. 8. A compound or mixture according to any one of Claims I to 7, in which R6 is R6', where R8' is (C14)alkyl, (C1~4)alkoxy or co-chloro- or methoxy-substituted (C1 3)alkyl,
  9. 9. A compound or mixture according to any one of Claims 5 to 8, in which R1 is R;, where R'1 is trifluoromethyl, -COOR'2, NHR3, -NHR3'R4' or NR5CORé.
  10. 10. A compound or mixture according to Claim 9, in which R1 is R''1, where R"1 is -COOR2' or NR'5COR"6 where R6, is methyl, ethyl, methoxy, 2-methoxyethyl or 3-methoxypropyl.
  11. Il. A compound or mixture according to Claim 10, in which R1 is R", where R;" is NR'5COR6" where R6"' is methyl or methoxy.
  12. 12. A compound according to any one of the preceding claims in which the ring A is further unsubstituted or further substituted by up to two substituents selected from chlorine, methyl and methoxy.
  13. 13. A compound or mixture according to Claim 9, in which the group (a) is (a,)
    in which R; is as defined in Claim 9, and the ring A is substituted by up to two substituents selected from halogen, (C14)alkyl, (C14)alkoxy and trifluoromethyl (only one further trifluoromethyl substltuent).
  14. 14. A compound or mixture according to Claim 13, in which (a) is (a2)
    wherein R;" is as defined in Claim 11 and R7 is hydrogen, chloride, methyl or methoxy.
  15. 15. A compound or mixture according to any one of the preceding claims, in which B is 1,4-naphthylene, 1 ,2,3,4-tetrahydronaphthylene or a group of formula (d)
    in which each of R8 and R9, independently, is hydrogen, (C1~4)alkyl or (C1-4)alkoxy.
  16. 16. A compound or mixture according to Claim 15, in which R8 is R8, where R8' is methyl, methoxy or ethoxy and R9 is R9', where R; is hydrogen, methyl, methoxy or ethoxy.
  17. i7. A compound or mixture according to Claim 16, in which (d) is a group (d,), where (d,) is a group of formula (d) where R8 is R' and R9 is R'9.
  18. 18. A compound or mixture according to Claim 15, in which B is 1,4naphthylene or a group of formula (d).
  19. 19. A compound or mixture according to Claim 1, in which D is a group of formula (a) or (b) and B is a group of formula (d) as defined in Claim 15, or 1,4naphthylene.
  20. 20. A compound or mixture according to Claim 13, in which D is a group of formula (a,) and B is (d,), as defined in Claim 17, or 1,4-naphthylene.
  21. 21. A compound or mixture according to Claim 20, in which, in the group of formula (a,), R, is -COOR2, or NR5COR8'.
  22. 22. A compound or mixture according to Claim 21, in which D is a group of formula (a2) as defined in Claim 14.
  23. 23. A compound or mixture according to Claim 22, in which D is a group of formula (a2) wherein R7 is hydrogen and R," is -NHCOCH3, B is (d2), where (d2) is (d) wherein R8 is methoxy and R9 is methyl or methoxy.
  24. 24. A compound of formula
    in which M is as defined in Claim 1.
  25. 25. A compound of formula
    in which M is as defined in Claim 1.
  26. 26. A compound of formula
    in which M is as defined in Claim 1.
  27. 27. A compound according to any one of Examples 2 to 4, 6 or 8 to 46.
  28. 28. A compound or mixture according to any one of the preceding claims in which M and, where R, is COOM, M,,are, in dependently, hydrogen or an alkali metal cation or a group of formula N(R,0)4 in which each R,,, independently, is hydrogen, (C,~3)alkyl or 2-, 3- or 4-hydroxy(C24)alkyl.
  29. 29. A compound or mixture according to Claim 28, in which M and M, are the same and signify hydrogen or an alkali metal cation.
  30. 30. A compound or mixture according to Claim 1, in which R, is other than --COOM, and, when R, is a group of formula -NR5COR6, R5 is hydrogen and R6 is (C16)alkyl.
  31. 31. A compound or mixture according to Claim 1, in which R1 is other than -COOM1.
  32. 32. A process for the production of a compound of formula 1, as defined in Claim 1, or a mixture thereof, comprising coupling the diazo derivative of an amine of formula II D-N=N-B-NH2 II or a mixture thereof with a compound of formula III,
    or a mixture thereof.
  33. 33. A process for the production of a compound of formula I, as defined in Claim I, or | a mixture thereof, substantially as hereinbefore described with reference to any one of Examples I to 46.
  34. 34. A compound of formula I, as defined in Claim 1, or a mixture thereof, whenever obtained by a process according to Claim 32 or Claim 33.
  35. 35. A process for dyeing or printing anionic dyeable substrates comprising employing a compound or mixture according to any one of Claims I to 31 or 34, as dyeing or printing agent.
  36. 36. A process according to Claim 35, in which the substrate consists of natural or synthetic polyamide fibres, basic modified polyolefins, polyurethanes or leather.
  37. 37. A process according to Claim 35, in which the substrate consists of wool, silk or nylon.
  38. 38. A process for dyeing or printing anionic dyeable substrates substantially as hereinbefore described with reference to Example A or B.
  39. 39. Dyed or printed substrates whenever obtained by a process according to any one of Claims 35 to 38.
GB30858/77A 1976-07-28 1977-07-22 Disazo dyestuffs containing 2-amino-8-hydroxy-naphthalene-6-sulphonic acid Expired GB1580660A (en)

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GB (1) GB1580660A (en)
HK (1) HK7982A (en)
IT (1) IT1079386B (en)
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JPH0670311B2 (en) * 1986-04-28 1994-09-07 キヤノン株式会社 Dyeing method and dyed product obtained by the method
US4753922A (en) * 1987-11-20 1988-06-28 Eastman Kodak Company Neutral-black dye-donor element for thermal dye transfer
JP5133713B2 (en) * 2008-01-21 2013-01-30 日東電工株式会社 Polarizer, coating liquid, and method for producing polarizer

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US1873606A (en) * 1930-05-28 1932-08-23 Gen Aniline Works Inc Secondary disazo dyes
DE2453209C2 (en) * 1974-11-09 1983-02-03 Bayer Ag, 5090 Leverkusen Disazo dyes, process for their preparation and their use

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HK7982A (en) 1982-03-05
ES8305808A3 (en) 1983-04-16
BE892014Q (en) 1982-08-04
FR2359883A1 (en) 1978-02-24
ES510236A0 (en) 1983-04-16
FR2359883B1 (en) 1982-07-09
MY8200240A (en) 1982-12-31
DE2732356A1 (en) 1978-02-02
JPS5316036A (en) 1978-02-14
KE3191A (en) 1982-04-02

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