WO2001030917A1 - Disazodyestuffs for ink jet printing - Google Patents
Disazodyestuffs for ink jet printing Download PDFInfo
- Publication number
- WO2001030917A1 WO2001030917A1 PCT/GB2000/004083 GB0004083W WO0130917A1 WO 2001030917 A1 WO2001030917 A1 WO 2001030917A1 GB 0004083 W GB0004083 W GB 0004083W WO 0130917 A1 WO0130917 A1 WO 0130917A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- optionally substituted
- alkyl
- compound according
- ink
- group
- Prior art date
Links
- 0 *c(cc(c(*)c1)[N+]([O-])=O)c1N Chemical compound *c(cc(c(*)c1)[N+]([O-])=O)c1N 0.000 description 2
- SFOYMLOIPNALBM-DVQJGIKISA-N Nc(cc1)cc(S(O)(=O)=O)c1/N=N/c(cc(c(/N=N/c(c(O)c(cc(cc1)Nc(cc2)cc(S(O)(=O)=O)c2N)c1c1)c1S(O)(=O)=O)c1)OCCO)c1OCCO Chemical compound Nc(cc1)cc(S(O)(=O)=O)c1/N=N/c(cc(c(/N=N/c(c(O)c(cc(cc1)Nc(cc2)cc(S(O)(=O)=O)c2N)c1c1)c1S(O)(=O)=O)c1)OCCO)c1OCCO SFOYMLOIPNALBM-DVQJGIKISA-N 0.000 description 1
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
- n is 0; L 1 and L 2 are H; and R 3 and R 4 are each independently H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, or R 3 and R 4 together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring.
- n is 1 ; L 1 and L 2 are H; and R 3 and R 4 are each independently H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, or R 3 and R 4 together with the N atom to which they are attached form an optionally substituted 5- or 6-membered ring.
- n is 1 ;
- L and L 2 are H;
- R 3 is H, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl; and
- R 4 is an acyl group.
- Preferred acyl groups represented by R 4 are of the formula -COR 5 , -SOR 5 or -
- R 1 or R 2 is an optionally substituted alkoxy group it is preferably an optionally substituted C 1-4 -alkoxy group, more preferably a C 1-4 -alkoxy or a C 1-4 -alkoxy-OH group.
- R 1 and R 2 are preferably each independently optionally substituted C 1-4 -alkyl or optionally substituted C 1-4 -alkoxy, provided that at least one of R 1 and R 2 carries an -OH group, more preferably optionally substituted C ⁇ -alkoxy, especially C ⁇ -alkoxy-OH.
- one of R and R 2 is -OC 1-4 -alkyl-OH and the other is -OC 1-4 - alkyl or -OC 1-4 -alkyl-OH.
- R 3 and R 4 are each independently selected from optionally substituted C 1-4 -alkyl and optionally substituted phenyl, or R 3 and R 4 together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6- membered ring. It is especially preferred that R 3 and R 4 are each independently selected from C 1-4 -alkyl, C ⁇ -alkyl-OH, phenyl and phenyl carrying a carboxy and/or sulpho group, or R 3 and R 4 together with the nitrogen to which they are attached form an optionally substituted morpholino or piperidino ring.
- R 3 is preferably selected from optionally substituted C ⁇ -alkyl and optionally substituted phenyl. It is especially preferred that when R 4 is acyl that R 3 is selected from C 1-4 -alkyl, C 1-4 -alkyl-OH, phenyl and phenyl carrying a carboxy and/or sulpho group. It is especially preferred that the group of formula -NR 3 R 4 is in the para position with respect to the azo linkage because this gives particularly good optical density.
- the dyes of Formulae (1 ) may be prepared by diazotising a compound of the Formula (2) to give a diazonium salt and coupling the resultant diazonium salt with a 1- hydroxy-3-sulphonaphthalene 1-hydroxy-3,6-disulphonaphthalene, in each case carrying an NL 1 L 2 substituent at the 7-position:
- the diazotisation is preferably performed at room temperature or below.
- the diazotisation is performed in water, preferably at a pH below 7.
- Dilute mineral acid e.g. HCI or H 2 S0 4 , may be used to achieve the desired acidic conditions.
- the dyes may be converted into a desired salt using known techniques.
- an alkali metal salt of a dye may be converted into the ammonium or substituted ammonia salt by dissolving an alkali metal salt of the dye in water, acidifying with a mineral acid and adjusting the pH of the solution to pH 9 to 9.5 with ammonia or the amine and removing the alkali metal cations by dialysis or by use of an ion exchange resin.
- amines which may be used to form such salts include methylamine, dimethylamine, trimethylamine, ethylamine, n-propylamine, iso-propylamine, n- butylamine, iso-butylamine, sec-butylamine, tert-butylamine, piperidine, pyridine, morpholine, allylamine, diethylamine, triethylamine and mixtures thereof. It is not essential that the dyes are completely in the form of the ammonium salt or substituted ammonium salt and mixed alkali metal and either ammonium salt or substituted ammonium salt are effective, especially those in which at least 50% of the cations are ammonium or substituted ammonium ions. Still further salts are those with the counter ions described in US 5,830,265, claim
- the dyes of Formula (1 ) may exist in tautome c forms other than those shown in this specification. These tautomers are included within the scope of the present claims.
- a preferred ink comprises:
- the number of parts of component (a) is preferably from 0.1 to 20, more preferably from 0.5 to 15, and especially from 1 to 5 parts.
- the number of parts of component (b) is preferably from 99.9 to 80, more preferably from 99.5 to 85, especially from 99 to 95 parts.
- component (a) When the medium is a liquid, preferably component (a) is completely dissolved in component (b).
- component (a) has a solubility in component (b) at 20°C of at least 10%. This allows the preparation of liquid dye concentrates which may be used to prepare inks and reduces the chance of the dye precipitating if evaporation of the liquid medium occurs during storage.
- Preferred liquid media include water, a mixture of water and an organic solvent and an organic solvent free from water.
- the weight ratio of water to organic solvent 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 organic solvent present in the mixture of water and organic solvent is a water-miscible organic solvent or a mixture of such solvents.
- Preferred water- miscible organic solvents include C ⁇ -alkanols, preferably methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, n-pentanol, cyclopentanol and cyclohexanol; linear amides, preferably dimethylformamide or dimethylacetamide; ketones and ketone-alcohols, preferably acetone, methyl ether ketone, cyclohexanone and diacetone alcohol; water-miscible ethers, preferably tetrahydrofuran and dioxane; diols, preferably diols having from 2 to 12 carbon atoms, for example pentane-1 ,5-diol, ethylene glycol
- the liquid medium comprises water and 2 or more, especially from 2 to 8, water-soluble organic solvents.
- water-soluble organic solvents are cyclic amides, especially 2- pyrrolidone, N-methyl-pyrrolidone and N-ethyl-pyrrolidone; diols, especially 1 ,5-pentane diol, ethyleneglycol, thiodiglycol, diethyleneglycol and triethyleneglycol; and mono- C ⁇ -alkyl and C ⁇ -alkyl ethers of diols, more preferably mono- C 1-4 -alkyl ethers of diols having 2 to 12 carbon atoms, especially 2-methoxy-2-ethoxy-2-ethoxyethanol.
- Examples of further suitable ink media comprising a mixture of water and one or more organic solvents are described in US 4,963,189, US 4,703,113, US 4,626,284 and EP 4,251 , 50A.
- Preferred water-immiscible solvents include, for example, aliphatic hydrocarbons; esters, preferably ethyl acetate; chlorinated hydrocarbons, preferably CH 2 CI 2 ; and ethers, preferably diethyl ether; and mixtures thereof.
- the organic solvent free from water may be a single organic solvent or a mixture of two or more organic solvents. It is preferred that when the medium is an organic solvent free from water it is a mixture of 2 to 5 different organic solvents. This allows a medium to be selected which gives good control over the drying characteristics and storage stability of the ink.
- Ink media comprising an organic solvent free from water are particularly useful where fast drying times are required and particularly when printing onto hydrophobic and non-absorbent substrates, for example plastics, metal and glass.
- Preferred low melting solid media have a melting point in the range from 60°C to 125°C.
- Suitable low melting point solids include long chain fatty acids or alcohols, preferably those with C 18 . 24 chains, and sulphonamides.
- the dye of Formula (1 ) may be dissolved in the low melting point solid or may be finely dispersed in it.
- Preferred black colorants include C.I. Food Black 2, C.I. Direct Black 19,
- a still further aspect of the present invention provides an ink jet printer cartridge, optionally refillable, comprising a chamber and an ink, wherein the ink is present in the chamber and the ink is as defined in the second aspect of the present invention.
- step 4 The product from step 2 was added to the product of step 1. Pyridine (5ml) was then added and the mixture allowed to self warm before stirring for a further 16hrs at room temperature. The product was then filtered off and washed with lithium chloride solution (500ml, 10%). The product was, filtered-off, pulled dry on the filter and used without further purification. Step 4
- Example 1 The method of Example 1 was repeated except that in step 4, 2R-Acid (22.26g) was used in place of Gamma acid.
- Example 3 The product from Example 3 was dissolved in water (11) and lithium hydroxide (80g) added. The solution was heated to 70-75°C until thin layer chromotography showed the hydrolysis to be complete (approx. 3hrs). The pH was adjusted to 8 and the solution cooled to 50°C. Lithium chloride (20% w/v) was then added slowly and the product isolated (hot) by filtration and washed with lithium chloride solution (11, 25%). The resultant product was dissolved in water (400ml) and purified by dialysis. Evaporation of the water at 70°C gave 11.87g of the title product having a lambda maximum of 604nm.
- step 3(53.1g) was dissolved in water (300ml) by adjusting the pH of the solution to 9 with lithium hydroxide (2M). Sodium nitrite (6.9g) was added and the solution added to a mixture of water (50ml) and hydrochloric acid (20ml). After stirring at room temperature for 1 hr excess nitrous acid was destroyed by the addition of sulphamic acid.
- step 2 The product from step 2 (25.8g) was added to a mixture of water (400ml) and hydrochloric acid (30ml) and cooled to 0-10°C. Sodium nitrite (7.59g) was slowly added and the solution further stirred for 1 hr before destroying excess nitrous acid by the addition of sulphamic acid. A solution of sodium N,N-diethylmetanilate (30g) in water (200ml) was added to the diazonium salt solution and the pH adjusted to 4-5 by careful addition of sodium hydroxide (2M). After stirring for 2hrs the pH was raised to 7 before stirring overnight at room temperature. The resulting suspension was adjusted to pH 1 with hydrochloric acid and the product isolated by filtration and washed with brine (20%w/v, 500ml).
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)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT00971556T ATE264374T1 (en) | 1999-10-29 | 2000-10-23 | DISAZO DYES FOR INKJET PRINTING |
EP00971556A EP1228149B1 (en) | 1999-10-29 | 2000-10-23 | Disazo dyestuffs for ink jet printing |
JP2001533904A JP2003513136A (en) | 1999-10-29 | 2000-10-23 | Diazo dyes for ink jet printing |
AU10395/01A AU1039501A (en) | 1999-10-29 | 2000-10-23 | Disazodyestuffs for ink jet printing |
DE60009940T DE60009940D1 (en) | 1999-10-29 | 2000-10-23 | DISAZO DYES FOR INK JET PRINTING |
US10/089,174 US6746526B1 (en) | 1999-10-29 | 2000-10-23 | Disazodyestuffs for ink jet printing |
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9925519.2 | 1999-10-29 | ||
GBGB9925521.8A GB9925521D0 (en) | 1999-10-29 | 1999-10-29 | Compounds |
GBGB9925522.6A GB9925522D0 (en) | 1999-10-29 | 1999-10-29 | Compounds |
GBGB9925519.2A GB9925519D0 (en) | 1999-10-29 | 1999-10-29 | Compounds |
GB9925522.6 | 1999-10-29 | ||
GBGB9925518.4A GB9925518D0 (en) | 1999-10-29 | 1999-10-29 | Compounds |
GB9925521.8 | 1999-10-29 | ||
GB9925518.4 | 1999-10-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001030917A1 true WO2001030917A1 (en) | 2001-05-03 |
Family
ID=27451926
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2000/004083 WO2001030917A1 (en) | 1999-10-29 | 2000-10-23 | Disazodyestuffs for ink jet printing |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1228149B1 (en) |
JP (1) | JP2003513136A (en) |
AT (1) | ATE264374T1 (en) |
AU (1) | AU1039501A (en) |
DE (1) | DE60009940D1 (en) |
WO (1) | WO2001030917A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006522196A (en) * | 2003-03-06 | 2006-09-28 | フジフィルム・イメイジング・カラランツ・リミテッド | Magenta metal chelate dye and its use in ink jet printers |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1527141B1 (en) * | 2002-07-27 | 2010-01-27 | FUJIFILM Imaging Colorants Limited | Processes, compositions and compounds |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0347803A2 (en) * | 1988-06-20 | 1989-12-27 | Orient Chemical Industries, Ltd. | Aqueous ink composition |
EP0611811A1 (en) * | 1991-11-07 | 1994-08-24 | Mitsubishi Kasei Corporation | Recording fluid |
EP0859033A1 (en) * | 1997-02-13 | 1998-08-19 | Ilford Ag | Dyes for ink jet printing |
WO2000050515A1 (en) * | 1999-02-25 | 2000-08-31 | Mitsubishi Chemical Corporation | Disazo dye, recording fluid containing the same, ink-jet recording fluid, and ink-jet recording method |
-
2000
- 2000-10-23 JP JP2001533904A patent/JP2003513136A/en active Pending
- 2000-10-23 AU AU10395/01A patent/AU1039501A/en not_active Abandoned
- 2000-10-23 DE DE60009940T patent/DE60009940D1/en not_active Expired - Lifetime
- 2000-10-23 EP EP00971556A patent/EP1228149B1/en not_active Expired - Lifetime
- 2000-10-23 AT AT00971556T patent/ATE264374T1/en not_active IP Right Cessation
- 2000-10-23 WO PCT/GB2000/004083 patent/WO2001030917A1/en active IP Right Grant
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0347803A2 (en) * | 1988-06-20 | 1989-12-27 | Orient Chemical Industries, Ltd. | Aqueous ink composition |
EP0611811A1 (en) * | 1991-11-07 | 1994-08-24 | Mitsubishi Kasei Corporation | Recording fluid |
EP0859033A1 (en) * | 1997-02-13 | 1998-08-19 | Ilford Ag | Dyes for ink jet printing |
WO2000050515A1 (en) * | 1999-02-25 | 2000-08-31 | Mitsubishi Chemical Corporation | Disazo dye, recording fluid containing the same, ink-jet recording fluid, and ink-jet recording method |
JP2000309721A (en) * | 1999-02-25 | 2000-11-07 | Mitsubishi Chemicals Corp | Disazo dye, recording fluid using same, ink-jet recording fluid, and ink-jet recording process |
Non-Patent Citations (1)
Title |
---|
DATABASE WPI Week 0057, Derwent World Patents Index; AN 2000-601817[57], "New disazodye for use in ink-jet recording inks" * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006522196A (en) * | 2003-03-06 | 2006-09-28 | フジフィルム・イメイジング・カラランツ・リミテッド | Magenta metal chelate dye and its use in ink jet printers |
Also Published As
Publication number | Publication date |
---|---|
ATE264374T1 (en) | 2004-04-15 |
EP1228149A1 (en) | 2002-08-07 |
EP1228149B1 (en) | 2004-04-14 |
JP2003513136A (en) | 2003-04-08 |
DE60009940D1 (en) | 2004-05-19 |
AU1039501A (en) | 2001-05-08 |
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