[go: up one dir, main page]

WO1996013553A1 - Colorant disaro - Google Patents

Colorant disaro Download PDF

Info

Publication number
WO1996013553A1
WO1996013553A1 PCT/GB1995/002494 GB9502494W WO9613553A1 WO 1996013553 A1 WO1996013553 A1 WO 1996013553A1 GB 9502494 W GB9502494 W GB 9502494W WO 9613553 A1 WO9613553 A1 WO 9613553A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
optionally substituted
compound
water
stage
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/GB1995/002494
Other languages
English (en)
Inventor
Ronald Wynford Kenyon
Prahalad Manibhai Mistry
Peter Gregory
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
Priority claimed from GB9421730A external-priority patent/GB9421730D0/en
Priority claimed from GB9421729A external-priority patent/GB9421729D0/en
Priority claimed from GB9421728A external-priority patent/GB9421728D0/en
Application filed by Zeneca Ltd filed Critical Zeneca Ltd
Priority to GB9704404A priority Critical patent/GB2306968B/en
Priority to AU37035/95A priority patent/AU3703595A/en
Publication of WO1996013553A1 publication Critical patent/WO1996013553A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by 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
    • 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

Definitions

  • This invention relates to a coloured bisazo compound and aqueous solutions thereof suitable for use in the coloration of substrates, especially sheet materials such as paper, and especially by a printing process such as ink jet printing.
  • A is optionally substituted phenyl or optionally substituted naphthyl
  • Y is an naphthylene group of Formula (1a) or a phenylene group of
  • R 1 and R 2 each independently is H, -COOH or -SO 2 OH
  • Z 1 is optionally substituted alkyl, optionally substituted alkoxy or
  • NZ 3 Z 4 Z 2 is H, halo, -COOH, SO 2 OH, optionally substituted alkyl, optionally substituted alkoxy, or optionally substituted alkylthio; Z 3 is H or optionally substituted alkyl; and Z 4 is H, optionally substituted alkyl or acyl.
  • R 3 Is H, optionally substituted alkyl or acyl
  • R 4 & R 5 each independently is H or optionally substituted alkyl; and R 6 is H, optionally substituted alkyl, optionally substituted aryl or acyl.
  • each of the compounds of Formulae (1), (2) & (3) has at least as many carboxy (-COOH) groups as sulpho (-SO 2 OH) groups, more preferably not more than 2 sulpho groups and especially 1 or 2 sulpho groups. It is preferred that each of the compounds of Formula (1), (2) and (3) has from 1 to 3, and especially 2 or 3 carboxy groups. Overall it is preferred that each of the compounds of Formula (1), (2) & (3) contains a total of from 2 to 5 -COOH and -SO 2 OH groups and especially 3 or 4 such groups.
  • A When A is substituted it preferably carries from one to three, especially one or two substituents, preferably in the 2-, 3-, 4-, 2,4-, 3,4-, 2,5- or 3,5- positions, selected from:
  • - alkyl preferably C ⁇ -alkyl and especially methyl
  • R 7 is optionally substituted C ⁇ -alkyl or optionally substituted aryl, especially phenyl; - optionally substituted amino, preferably -NQ 1 Q 2 wherein Q 1 and Q 2 are each independently H or optionally substituted alkyl or aryl, or Q 1 and Q 2 , taken together with the N atom to which they are attached, form an optionally substituted 5- or 6- membered ring; and
  • acylamino especially alkyl- or aryl-carbonylamino or alkyl- or aryl-sulphonylamino, more especially C M -alkyl-CONH- or C M -alkyl-SO 2 NH-.
  • A is carboxyphenyl or carboxynaphthyl, such as 3- or 4- carboxyphenyl, or carboxyphenyl having one or two further substituents, especially one, selected from carboxy, sulpho, methyl, methoxy and chloro. It is especially preferred that A carries at least two carboxy groups.
  • Examples of preferred and especially preferred optionally substituted phenyl and naphthyl groups represented by A are 4-carboxyphenyl, 3-carboxyphenyl, 3,5-dicarboxyphenyl, 3,4-dicarboxyphenyl, 2-methyl-5-carboxyphenyl, 2- sulpho-5-carboxyphenyl, 4-carboxynaphth-1-yl, 5-carboxy-naphth-1-yl, 6-carboxynaphth-1-yl, 7-carboxynaphth-1-yl, 6-carboxynaphth-2-yl and 1-sulpho-6-carboxynaphth-2-yl.
  • R 1 and R 2 are H and the other is H, -COOH or -SO 2 OH.
  • one of R 1 and R 2 is -COOH or -SO 2 OH and the other is H, it is convenient to employ a mixture of isomeric compounds in one of which R 1 is H and R 2 is -COOH or -SO 2 OH and in the other R 2 is H and R 1 is -COOH or -SO 2 OH.
  • Z 3 is H or C w -alkyl, such as methyl or ethyl. It is especially preferred that Z 3 is H. Where Z 4 is alkyl this is preferably C M -alkyl. Where Z 4 is acyl this is preferably NH 2 CO-, R 7 CO- or R 7 SO 2 -, wherein R 7 is as hereinbefore defined, i.e. optionally substituted C ⁇ -alkyl or optionally substituted aryl, especially phenyl. Where Z 4 is other than H, and especially where it is acyl, Z 3 is preferably H. It is preferred that NZ 3 Z 4 in NH 2 .
  • Z 1 is optionally substituted alkyl or optionally substituted alkoxy
  • Z 1 is C M -alkyl such as methyl or ethyl or C ⁇ -alkoxy such as methoxy or ethoxy and it is especially preferred that Z 1 is H, methyl or methoxy.
  • Z 2 is C ⁇ -alkyl, C ⁇ -alkoxy, C lJr alkylthio, Cl, H, COOH or SO 2 OH, more preferably C ⁇ -alkyl, such as methyl or ethyl, or C ⁇ -alkoxy, such as methoxy or ethoxy and it is especially preferred that Z 2 is methyl or methoxy.
  • the C 2 _ 6 -alkylene group represented by B is preferably a C 2 - or C 3 -alkylene groups, especially ethylene, isopropylene or n-propylene, optionally substituted by one of the groups listed below as optional substituents for the alkyl groups represented by R 3 & R 4 , but is preferably unsubstituted. It is preferred that T is H.
  • R 3 and R 6 each independently is H, C M -alkyl, C M -alkyl- carbonyl, C M -alkoxycarbonyl or arylcarbonyl, especially phenylcarbonyl or the equivalent sulphonyl groups.
  • groups are methyl, ethyl, acetyl, methylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoxysulphonyl and benzoyl.
  • R 3 is H or C M -alkyl and R 6 is H, C M -alkyl, C lJ( -alkylcarbonyl, C M -alkoxycarbonyl or benzoyl and more especially that R 3 and R 6 are both H. It is preferred that R 4 and R 5 are each independently H or C ⁇ -alkyl and more especially that both are H.
  • R 3 , R 4 , R 5 , R 6 , R 7 , Q 1 , Q 2 , Z 1 , Z 2 , Z 3 or Z 4 is or includes optionally substituted alkyl, this is preferably C M -alkyl, such as methyl, ethyl, propyl or butyl, optionally substituted by C M -alkoxy, halo, especially chloro, OH, COOR 8 or -SO 2 OH in which R 8 is H, C ⁇ -alkyl or phenyl.
  • R 6 , R 7 , Q or Q 2 is or includes optionally substituted aryl this is preferably phenyl, optionally substituted, preferably in the 2-, 3-, 4-, 2,4-, 3,4- or 3,5- positions, by a group or groups selected from C ⁇ -alkyl, C M -alkoxy, halo, OH, NH 2 , CN, NO 2 , -COOH and -SO 2 OH.
  • a preferred compound of Formula (2) is where A is optionally substituted carboxyphenyl wherein any further substituent is selected from -COOH, -SO 2 OH, methyl, methoxy, chloro and hydroxy, especially 3- or 4-carboxyphenyl or 3,4- or 3,5-dicarboxyphenyl; R 2 is H, -COOH or -SO 2 OH; each of T, R 1 , R 3 and R 6 is H; B is ethylene or propylene; and J is piperazinyl.
  • An especially preferred compound of Formula (2) is where A is 3- or 4-carboxyphenyl or 3,4- or 3,5-dicarboxyphenyl; B is eth-1 ,2-ylene, prop-1 ,2-ylene, or prop-1 ,3-ylene; J is piperazin-1-yl; R 2 is H or -SO 2 OH; and each of R 1 , R 3 , R 6 and T is H.
  • a preferred compound of Formula (3) wherein Z 1 is not NZ 3 Z 4 is where A is optionally substituted carboxyphenyl wherein any further substituent is selected from -COOH, -SO 2 OH, methyl, methoxy, chloro and hydroxy, especially 3- or 4-carboxyphenyl or 3,4- or 3,5-dicarboxyphenyl; Z 1 is methyl or methoxy; Z 2 is H, methyl or methoxy; T and R 3 are both H; B is ethylene or propylene; and J is piperazinyl.
  • A is 3- or 4-carboxyphenyl or 3,4- or 3,5-dicarboxyphenyl
  • B is eth-1 ,2-ylene, prop-1 ,2-ylene, or prop-1 ,3-ylene
  • J is piperazin-1-yl
  • Z 1 is methyl or methoxy
  • Z 2 is H, methyl or methoxy
  • R 3 and T are H.
  • the two azo groups are in para (1 ,4) relationship across the central phenylene group and that Z 2 and Z 1 are also in para (1 ,4) relationship across the central phenylene group. It is also preferred that Z 1 is ortho to the azo group linking A to the central phenylene group and that Z 2 is ortho to the azo group linking the Gamma acid moiety to the central phenylene group.
  • a preferred compound of Formula (3) wherein Z 1 is NZ 3 Z 4 is where A is optionally substituted carboxyphenyl wherein any further substituent is selected from -COOH, -SO 2 OH, methyl, methoxy, chloro and hydroxy, especially 3- or 4-carboxyphenyl or 3,4- or 3,5-dicarboxyphenyl, Z 2 is H, methyl or methoxy, Z 3 is H or C ⁇ -alkyl; Z 4 is H, C ⁇ -alkyl, especially methyl or ethyl, -COC lJt -alkyl, especially acetyl or propionyl, or -COaryl, especially benzoyl; T and R 3 are both H; B is ethylene or propylene; and J is piperazinyl.
  • A is 3- or 4-carboxyphenyl or 3,4- or 3,5-dicarboxyphenyl
  • B is eth-1 ,2-ylene, prop-1 ,2-ylene or prop-1 ,3-ylene
  • J is piperazin-1-yl
  • Z 2 is H, methyl or methoxy
  • Z 4 is H, methyl, ethyl, acetyl or propionyl
  • R 3 , Z 3 and T are H.
  • a 1 is 3-carboxyphenyl, 4-carboxyphenyl, 3,4-dicarboxyphenyl, 3,5-dicarboxyphenyl or 2-methyl-5-carboxyphenyl
  • B 1 is eth-1 ,2-ylene, prop-1 , 2-ylene or prop-1 , 3-ylene;
  • J 1 is piperazin-1-yl
  • R 1 and R 2 are as hereinbefore defined. It is preferred that R 1 is H and R 2 is H or SO 2 OH.
  • a preferred compound of Formula (3) is represented by Formula (5), or a salt thereof :
  • a 1 is 3-carboxyphenyl, 4-carboxyphenyl, 3,4-dicarboxyphenyl, 3,5-dicarboxyphenyl or 2-methyl-5-carboxyphenyl
  • B 1 is eth-1 ,2-ylene, prop-1 ,2-ylene or prop-1 ,3-ylene; J 1 is piperazin-1-yl; and
  • Z 1 and Z 2 are as hereinbefore defined.
  • Z 1 is NH 2 , -NHC M -alkyl, especially methylamino or ethylamino; or -NHCOC ⁇ -alkyl, especially acetyl- amino; and Z 2 is H, C ⁇ -alkyl or C M -alkoxy, especially methyl or methoxy. It is especially preferred that Z 1 is NH 2 or acetylamino and Z 2 is H, C M -alkyl or C M -alkoxy, especially methoxy.
  • Z 1 is C ⁇ -alkyl or C lJr alkoxy, especially methyl or methoxy and Z 2 is H, C lJt -alkyl or C M -alkoxy, especially methyl or methoxy.
  • the compound of Formula (1 ), (2) or (3) may be in the free acid form, as shown, but is preferably in the form of a salt with one or more cations selected from an alkali metal, ammonium and optionally substituted cation
  • a preferred cation consist of a nitrogen atom having four substituents selected from H, C M -alkyl and hydroxy-C M -alkyl, for example mono-, di-, t ⁇ - and tetra-(C 1u) -alkyl)- ammonium and mono-, di-, t ⁇ - and tetra-(hydroxy-C M -alkyl)ammon ⁇ um
  • the compound of Formula (1 ), (2) or (3) is a salt with an ammonium (i e NH ), or a mono- or poly-, methyl- or ethyl-ammonium cation or with a mixture of two or more cations, especially a mixture of alkali metal, (such as sodium) and ammonium cations
  • the present compounds can be prepared by diazotising an amine of formula A-NH 2 , preferably below 5°C using a nitrite and mineral acid, coupling with a substituted aminonaphthalene carrying groups R 1 and R 2 or with a substituted aniline carrying groups Z 1 and Z 2 to give a monoazo compound, diazotising the resultant monoazo compound and coupling with a Gamma acid derivative of Formula (6):
  • Compounds of Formula (6) may be prepared using the Bucherer reaction in which 1-hydroxy-3-sulpho-7-hydroxy (or 7-amino)-naphthalene or 1-hydroxy-3,6-disulpho-7- hydroxy (or 7-amino)-naphthalene is reacted with an amine, R 3 -NH-B-J, in the presence of an alkali metal or ammonium sulphite and bisulphite (e.g. Na 2 SO 3 and NaHS0 3 ) with heating, preferably from 60-100°C and especially 70-90°C.
  • an alkali metal or ammonium sulphite and bisulphite e.g. Na 2 SO 3 and NaHS0 3
  • R 3 is acyl in the compound of Formula (1) it is necessary to use an amine, H-NH-B-J in the above reaction and to incorporate the acyl group subsequently by acylation of the secondary amino group.
  • A, R 1 , R 2 , R 3 , Z 1 , Z 2 , T, B and J are as hereinbefore defined.
  • the present invention relates not only to a compound of Formula (1) or (2) or (3) but also to a composition comprising two or more such compounds.
  • An example of such a composition is a mixture containing two compounds of Formula (2) in one of which R 1 is H and R 2 is -COOH or -SO 2 OH and in the other R 1 is -COOH or -SO 2 OH and R 2 is H. It is preferred that such a composition contains two compounds of Formula (1) in a weight-to-weight ratio of 99:1 to 1 :99, more preferably 90:10 to 10:90, especially 80:20 to 20:80, more especially 60:40 to 40:60.
  • the compound or composition of the present invention may be converted wholly or partially into its ammonium or optionally substituted salt by dissolving in water the compound in the form of a salt with an alkali metal, acidifying the solution with a mineral acid, e.g. hydrochloric acid, separating of the precipitated compound in free acid form, suspending it in water, adjusting the suspension to pH 9-9.5 with ammonia or an optionally substituted lower alkylamine to form the water soluble ammonium or substituted ammonium salt, and removing alkali metal chloride ions by dialysis
  • the alkali metal ion may be partially or wholly exchanged for an optionally substituted ammonium ion by a conventional ion exchange method. It will be understood that the present invention covers all tautome ⁇ c forms of a compound of Formula (1 ) or (2) or (3) for example the tautomeric equivalent of Formula
  • a compound or composition of the present invention is a useful colorant for a black ink. It has good solubility in water and aqueous media and good water fastness and is capable of giving a water-fast print with a strong black shade on plain paper.
  • the compound and composition are versatile, exhibiting high water fastness and rapid fixation on alkaline, neutral and acid papers, good solubility in aqueous ink media and good strong black prints with minimal bronzing.
  • a suitable ink comprises a compound or a composition according to the present invention and a liquid medium, preferably an aqueous medium. It is preferred that the compound or composition is completely dissolved in the liquid medium to form a solution.
  • the ink preferably contains from 0.5% to 20%, more preferably from 0.5% to 15%, and especially from 1 % to 3%, by weight of the compound or composition, based on the total weight of the ink. Although many inks contain less than 5% by weight of colorant, it is desirable that the compound or composition has a water solubility of around 10% or more to allow the preparation of concentrates from which more dilute inks can be prepared and to minimise the chance of precipitation of colorant if evaporation of solvent occurs during use of the ink.
  • the liquid medium is preferably water or a mixture of water and one or more water-soluble organic solvent.
  • the weight ratio of water to organic solvent(s) is preferably from 99:1 to 1 :99, more preferably from 99:1 to 50:50 and especially from 95:5 to 80:20.
  • the water-soluble organic solvent(s) is preferably selected from C lJ( -alkanols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol or isobutanol; amides such as dimethylformamide or dimethylacetamide; ketones or ketone- alcohols such as acetone or diacetone alcohol; ethers such as tetrahydrofuran or dioxane, oligo- or poly-alkyleneglycols such as diethylene glycol, triethylene glycol.
  • C lJ( -alkanols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol or isobutanol
  • amides such as dimethylformamide or dimethylacetamide
  • polyethylene glycol or polypropylene glycol alkyleneglycols or thioglycols containing a C 2 -C 6 -alkylene group such as ethylene glycol, propylene glycol, butylene glycol, pentylene glycol or hexylene glycol and thiodiglycol; polyols such as glycerol or 1 ,2,6-hexanetr ⁇ ol, C ⁇ -alkyl- ethers of polyhydric alcohols such as 2-methoxyethanol, 2-(2-methoxyethoxy)ethanol, 2-(2-ethoxyethoxy)-ethanol, 2-[2-(2-methoxyethoxy)ethoxy]ethanol, 2-[2-(2-ethoxyethoxy)- ethoxy]-ethanol; heterocyclic ketones, such as 2-pyrrolidone and N-methyl-2-pyrrolidone; or mixtures containing two or more of the aforementioned water-soluble organic solvents, for example thiodiglycol and
  • Preferred water-soluble organic solvents are 2-pyrrolidone; N-methyl- pyrrolidone; alkylene- and oligo-alkylene-glycols, such as ethyleneglycol, diethyleneglycol, triethyleneglycol; and lower alkyl ethers of polyhydric alcohols such as or 2-methoxy- 2-ethoxy-2-ethoxyethanol; and polyethyleneglycols with a molecular weight of up to 500.
  • a preferred specific solvent mixture is a binary or ternary mixture of water and diethylene glycol and/or, 2-pyrrolidone or N-methylpyrrolidone in weight ratios 75-95:25-5 and 60-80:0- 20:0-20 respectively.
  • a further aspect of the present invention provides a process for printing a substrate with an ink using an ink jet printer, characterised in that the ink contains at least one compound according to Formula (1) or (2) or (3) as hereinbefore described.
  • a suitable process for the application of an ink as hereinbefore described comprises forming the ink into small droplets by ejection from a reservoir through a small orifice so that the droplets of ink are directed at a substrate.
  • This process is commonly referred to as ink jet printing, and preferred ink jet printing processes for the present inks are piezoelectric ink jet printing and thermal ink jet printing.
  • thermal ink jet printing programmed pulses of heat are applied to the ink in the reservoir by means of a resistor adjacent to the orifice, during relative movement between the substrate and the reservoir.
  • a preferred substrate is an overhead projector slide or a cellulosic substrate, especially cotton or paper, including plain and treated papers, which may have an acid, alkaline or neutral character.
  • the preferred ink used in the process is as hereinbefore described.
  • the monoazo dye prepared in Stage 1 (29 05g) was dissolved in water (800ml) by addition of 2N NaOH solution to pH 9 NaN0 2 (5 5g) was added and the solution added at 0-10°C to a mixture of ice/water (100g) and concentrated HCI (30 ml) The diazo suspension was stirred for 4 hours at 0-10°C and excess HN0 2 removed by addition of a little sulphamic acid
  • the N-(2-p ⁇ peraz ⁇ noethyl)-Gamma acid prepared in Stage 2 (30g) was dissolved in water (400ml) by addition of 2N NaOH, cooled to 0-10°C
  • the above diazo suspension was added at 0-10°C maintaining the pH at 8-9 by addition of 2N NaOH solution
  • the mixture was stirred for 1 hour at 0-10"C and then heated to 70-80°C It was then salted to 20% with NaCI and the pH adjusted to 6 by addition of 2N HCI
  • the precipitated product was filtered and washed with 25% NaCI solution Sta ⁇ e 4 Compound of Formula (A) in which M is NH/
  • the product from Stage 3 was added to water (1 51), the pH adjusted to 9 by addition of concentrated NH 4 OH, the resulting solution added to a water (500ml) and concentrated HCI (30ml) mixture and the precipitated product filtered off.
  • the product in the form of its ammonium salt was made into an ink (2.5% in water/diethylene glycol 90/10) and printed onto plain paper using a thermal ink jet printer. It gave a black shade with very high waterfastness.
  • Example 2 This was prepared as in Example 2 of EP 356080.
  • Staoe 2 Compound of formula (B) In place of the 29.05g of the monoazo dye used in Stage 3 of Example 1 there was used 25.6g of the monoazo dye prepared as in Stage 1 of Example 2.
  • the product was converted to the ammonium salt as in Stage 4 of Example 1, dialysed and screened through a 0.45 micron filter and then evaporated and dried. When made into a 2% ink in water/2-pyrrolidone (90/10), and printed onto plain paper using a thermal ink jet printer, it agave a black shade with very high waterfastness.
  • Example 3 Example 3
  • 3-Aminobenzoic acid (27.4g) was added to a mixture of water (500ml) and concentrated HCI (50ml).
  • a solution of NaNO 2 (14.0g) in water (50ml) was added at 0-5°C and the mixture stirred at 0-5 c C for V ⁇ hr.
  • Excess HNO 2 was removed by addition of a little sulphamic acid.
  • N-(2-P ⁇ peraz ⁇ noethyl)-Gamma acid (25g) from Example 1 Stage 2 was dissolved in water (400ml) by addition of 2N NaOH to pH 9 The solution was cooled to 0-10°C and the above diazo added slowly at 0-10°C maintaining the pH at 8-9 by addition of 2N NaOH. The mixture was then stirred for 1 hour at 0-10°C and then heated to 70°C, salted to 20% with NaCI, the pH adjusted to 4-5 by addition of concentrated HCI and the product filtered off and washed with 25% aqueous NaCI.
  • Sta ⁇ e 3 Compound of Formula (IP in which M is H and T is H
  • the product from Stage 3 was dissolved in water (11) by addition of concentrated NH 4 OH, the solution added to a mixture of water (500ml) and concentrated HCI (30ml) and the product filtered off. This procedure was repeated twice and the isolated product dissolved in water by addition of NH 4 OH to pH 9-10. The solution was dialysed until Cl " ion could no longer be detected, screened through a 0.45 micron filter and evaporated and dried at 60-70°C.
  • Stage 2 Compound of Formula ( ) where M is H and T is COCH,
  • the dry product was made into an ink (2% in water:2-pyrrolidone, 90:10) and printed onto plain paper using a thermal ink jet printer. It gave a fast fixing image having excellent water fastness and a strong black shade.
  • the product of Stage 1 was dissolved in water (800ml) at room temperature by the addition of sufficient 2N NaOH to raise the pH to 9-10 and NaNO 2 (5.5g) was added. This solution was added over a period of 10 minutes to a mixture of concentrated HCI (30ml) and ice-water (150ml), maintaining the temperature at 0-10°C. After 3 hours at 0-10°C excess HNO 2 was destroyed by the addition of sulphamic acid to give a diazo solution.
  • N-(2-piperazinylethyl)-Gamma acid (30.2g) from Stage 2 of Example 1 was dissolved in water (500ml) by the addition of 2N NaOH to pH 9.0 followed by Na 2 CO 3 and the solution was cooled to 0-10°C.
  • the diazo solution was then added slowly over 10 minutes, maintaining the temperature at 0-10°C by the addition of ice and the pH at 9-10 by addition of 2N NaOH solution.
  • the mixture was then stirred for 18 hours allowing the temperature to rise to 20°C.
  • the suspension was then heated to 70°C, salted to 20% with NaCI and the pH adjusted to 6 with 2N HCI.
  • the precipitated product (of Formula (Q) in Na salt form) was filtered and washed with 25% NaCI solution.
  • the filter paste from Stage 2 was dissolved in water (11) by adjusting the pH to 9-10 with cone NH 4 OH. It was then slowly added to 2N HCI (21). The compound of Formula (Q), in free acid form, was filtered and washed with 1N HCI. This procedure was repeated twice before the filter paste was added to water (500ml) and the solid completely dissolved by adjusting to pH 9-10 with cone NH 4 OH. The solution was dialysed until Cl " could no longer be detected, screened through a 0.45 ⁇ m filter, and the product of Formula (Q) (as ammonium salt) isolated by evaporation and dried at 70 ⁇ C.
  • the compound of Formula (Q) (ammonium salt) (2.5 parts) was added to a mixture of water (90 parts) and diethylene glycol (10 parts) and printed onto plain paper substrate using a thermal ink jet printer.
  • the print had a bluish-black shade with excellent water fastness and a fast rate of fixation to the substrate.
  • Example 32 Preparation of the Compound of Formula (R)
  • 3-Aminobenzoic acid (27.4g) was added to a mixture of water (500ml) and concentrated hydrochloric acid (50ml). The solution was cooled to 0-5°C and a solution of sodium nrtrile (15 2g) in water (50ml) was gradually added at 0-5°C After stirring for 1 hour excess nitrous acid was destroyed by addition of a little sulphamic acid
  • each dye of Formula (W) When made into an ink (2% in water/2-pyrrolidone, 90/10) each dye of Formula (W) will give an image having a black shade and very high waterfastness.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

Composé de la formule (1) ou sel de celui-ci, formule dans laquelle A représente phényle éventuellement substitué ou naphtyle éventuellement substitué; Y représente un groupe naphtylène de la formule (1a) ou un groupe phénylène de la formule (1b) dans lesquelles R1 et R2 représentent chacun indépendamment H, -COOH ou -SO¿2OH, Z?1 représente alkyle éventuellement substitué, alcoxy éventuellement substitué ou NZ3Z4, Z2 représente H, halo, -COOH, SO¿2?OH, alkyle éventuellement substitué, alcoxy éventuellement substitué, ou alkylthio éventuellement substitué; Z?3¿ représente H ou alkyle éventuellement substitué, et Z4 représente H, alkyle ou acyle éventuellement substitué; R3 représente H, alkyle ou acyle éventuellement substitué; T représente H ou sulfo, B représente alkylène C¿2-6? et J représente un groupe de la formule (1c) dans laquelle R?4 et R5¿ représentent chacun indépendamment H ou alkyle éventuellement substitué; et R6 représente H, alkyle éventuellement substitué, aryle ou acyle éventuellement substitué. Le composé de la formule (1), sous la forme d'un sel, notamment d'un sel d'ammonium, est utile dans la préparation d'encres destinées à la production, sur papier ordinaire et à l'aide d'une impression par jet d'encre, d'images noires à fixation rapide et résistantes à l'eau.
PCT/GB1995/002494 1994-10-28 1995-10-23 Colorant disaro Ceased WO1996013553A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB9704404A GB2306968B (en) 1994-10-28 1995-10-23 Disazo colorant
AU37035/95A AU3703595A (en) 1994-10-28 1995-10-23 Disaro colorant

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB9421730.4 1994-10-28
GB9421730A GB9421730D0 (en) 1994-10-28 1994-10-28 Organic chemical
GB9421729.6 1994-10-28
GB9421729A GB9421729D0 (en) 1994-10-28 1994-10-28 Organic chemical
GB9421728A GB9421728D0 (en) 1994-10-28 1994-10-28 Organic chemical
GB9421728.8 1994-10-28

Publications (1)

Publication Number Publication Date
WO1996013553A1 true WO1996013553A1 (fr) 1996-05-09

Family

ID=27267449

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1995/002494 Ceased WO1996013553A1 (fr) 1994-10-28 1995-10-23 Colorant disaro

Country Status (3)

Country Link
AU (1) AU3703595A (fr)
GB (1) GB2306968B (fr)
WO (1) WO1996013553A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2318122A (en) * 1996-10-11 1998-04-15 Zeneca Ltd Disazo dyes based on 7-(optionally substituted amino)-3-sulphonaphth-1-ol coupling component and their use in inkjet inks
GB2318124A (en) * 1996-10-11 1998-04-15 Zeneca Ltd Disazo dyes based on 7-(optionally substituted amino)-3-sulphonaphth-1-ol coupling component and their use in inkjet inks
GB2318357A (en) * 1996-10-11 1998-04-22 Zeneca Ltd Disazo dyes based on 7-(optionally substituted amino)-3-sulphonaphth-1-ol coupling component and their use in inkjet inks
GB2318358A (en) * 1996-10-11 1998-04-22 Zeneca Ltd Disazo dyes based on 7-(optionally substituted amino)-3-sulphonaphth-1-ol coupling component and their use in inkjet inks
WO1998023690A1 (fr) * 1996-11-27 1998-06-04 Eastman Chemical Company Procede de preparation de compositions polymeres absorbant la lumiere
US5843218A (en) * 1996-10-11 1998-12-01 Zeneca Limited Bisazo inkjet dyes
US5869627A (en) * 1995-07-13 1999-02-09 Zeneca Limited Stabilised dye composition
WO1999013008A1 (fr) * 1997-09-09 1999-03-18 Avecia Limited Colorants disazoiques solubles dans l'eau et encres pour procede d'impression par jets d'encre contenant ces colorants
US5888286A (en) * 1996-10-11 1999-03-30 Zeneca Limited Bisazo ink-jet dyes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2180390C2 (ru) * 1999-10-25 2002-03-10 Общество с ограниченной ответственностью "Кубаньгазпром" Пакер

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0249127A2 (fr) * 1986-06-11 1987-12-16 Bayer Ag Liquide d'enregistrement pour systèmes d'enregistrement par jet d'encre
EP0356080A2 (fr) * 1988-08-24 1990-02-28 Zeneca Limited Colorant anionique
WO1994016021A1 (fr) * 1993-01-12 1994-07-21 Zeneca Limited Compose azo

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9514386D0 (en) * 1995-07-13 1995-09-13 Zeneca Ltd Stabilised dye composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0249127A2 (fr) * 1986-06-11 1987-12-16 Bayer Ag Liquide d'enregistrement pour systèmes d'enregistrement par jet d'encre
EP0356080A2 (fr) * 1988-08-24 1990-02-28 Zeneca Limited Colorant anionique
WO1994016021A1 (fr) * 1993-01-12 1994-07-21 Zeneca Limited Compose azo

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5869627A (en) * 1995-07-13 1999-02-09 Zeneca Limited Stabilised dye composition
US5891230A (en) * 1996-10-10 1999-04-06 Zeneca Limited Bisazo ink-jet dyes
GB2318358A (en) * 1996-10-11 1998-04-22 Zeneca Ltd Disazo dyes based on 7-(optionally substituted amino)-3-sulphonaphth-1-ol coupling component and their use in inkjet inks
GB2318357B (en) * 1996-10-11 2000-12-20 Zeneca Ltd Bisazo ink-jet dyes
GB2318122A (en) * 1996-10-11 1998-04-15 Zeneca Ltd Disazo dyes based on 7-(optionally substituted amino)-3-sulphonaphth-1-ol coupling component and their use in inkjet inks
US5843218A (en) * 1996-10-11 1998-12-01 Zeneca Limited Bisazo inkjet dyes
GB2318357A (en) * 1996-10-11 1998-04-22 Zeneca Ltd Disazo dyes based on 7-(optionally substituted amino)-3-sulphonaphth-1-ol coupling component and their use in inkjet inks
US5882392A (en) * 1996-10-11 1999-03-16 Zeneca Limited Bisazo inkjet dyes
US5882391A (en) * 1996-10-11 1999-03-16 Zeneca Limited Bisazo inkjet dyes
GB2318358B (en) * 1996-10-11 2001-04-25 Zeneca Ltd Bisazo ink-jet dyes
US5888286A (en) * 1996-10-11 1999-03-30 Zeneca Limited Bisazo ink-jet dyes
GB2318124A (en) * 1996-10-11 1998-04-15 Zeneca Ltd Disazo dyes based on 7-(optionally substituted amino)-3-sulphonaphth-1-ol coupling component and their use in inkjet inks
GB2318122B (en) * 1996-10-11 2001-02-07 Zeneca Ltd Bisazo ink-jet dyes
WO1998023690A1 (fr) * 1996-11-27 1998-06-04 Eastman Chemical Company Procede de preparation de compositions polymeres absorbant la lumiere
GB2346151A (en) * 1997-09-09 2000-08-02 Avecia Ltd Water soluble disazo dyestuffs as well as inks for ink jet recording method containing them
WO1999013008A1 (fr) * 1997-09-09 1999-03-18 Avecia Limited Colorants disazoiques solubles dans l'eau et encres pour procede d'impression par jets d'encre contenant ces colorants
GB2346151B (en) * 1997-09-09 2002-04-10 Avecia Ltd Water soluble disazo dyestuffs as well as inks for ink jet recording method containing them

Also Published As

Publication number Publication date
GB2306968B (en) 1998-08-05
GB2306968A (en) 1997-05-14
GB9704404D0 (en) 1997-04-23
AU3703595A (en) 1996-05-23

Similar Documents

Publication Publication Date Title
US5177195A (en) Disazo dyes
JP3628325B2 (ja) アゾ化合物
JPH05311087A (ja) インク、基質をプリントする方法、染料、プリントされたペーパー又はオーバーヘッドプロジェクタースライド及び染料組成物
WO1996013553A1 (fr) Colorant disaro
EP0759956B1 (fr) Compose disazo
GB2289473A (en) Disazo compound
EP0572419B1 (fr) Colorants disazo anioniques
US5423906A (en) Trisazo dyes, inks comprising same and their use in ink jet printing
US5969114A (en) Azo compound
EP1257601A1 (fr) Colorants, encres et leur utilisation en impression a jet d'encre
US6517620B1 (en) Mono-azo dyes and inks for ink-jet printing
EP0888406B1 (fr) Composes azo
WO1995017471A1 (fr) Compose disazo
US5254675A (en) Anionic disazo dyes
US6344076B1 (en) Monoazo dyes and inks containing them
GB2251625A (en) Disazo compounds
JPH11279469A (ja) 水性インク組成物及び着色体
GB2330841A (en) Di- & tri-azinylamino monoazo dyes for use in ink jet inks
HK1003838B (en) Azo compound
GB2317183A (en) (Indanyl-azo)-(triazinylamino)-naphthol-sulphonic acids, free of fibre-reactive groups, as colourants for ink jet inks
WO1999013008A1 (fr) Colorants disazoiques solubles dans l'eau et encres pour procede d'impression par jets d'encre contenant ces colorants

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AM AT AU BB BG BR BY CA CH CN CZ DE DK EE ES FI GB GE HU IS JP KE KG KP KR KZ LK LR LT LU LV MD MG MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TT UA UG US UZ VN

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase