WO2002070609A1 - Ink jet printing composition comprising a dye containing hydrazine or hydrazide - Google Patents
Ink jet printing composition comprising a dye containing hydrazine or hydrazide Download PDFInfo
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- WO2002070609A1 WO2002070609A1 PCT/GB2002/000810 GB0200810W WO02070609A1 WO 2002070609 A1 WO2002070609 A1 WO 2002070609A1 GB 0200810 W GB0200810 W GB 0200810W WO 02070609 A1 WO02070609 A1 WO 02070609A1
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- Prior art keywords
- formula
- compound
- groups
- optionally substituted
- hydrazide
- Prior art date
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- 0 C*C(C=C[C@]1N=CC(c(c(O)c(c(*)cc(S(O)(=O)=O)c2)c2c2)c2S(O)(=O)=O)=C)=CC1S(O)(=O)=O Chemical compound C*C(C=C[C@]1N=CC(c(c(O)c(c(*)cc(S(O)(=O)=O)c2)c2c2)c2S(O)(=O)=O)=C)=CC1S(O)(=O)=O 0.000 description 2
- TXZFHNVNJBPRDS-JEAZKISVSA-N CC(CC=C1C(O)=O)C=C1/N=N/c(c(S(O)(=O)=O)cc1c2c(Nc3nc(NNC(c(cc4)ccc4C(NNc4nc(Nc(cc(cc5cc6S(O)(=O)=O)S(O)(=O)=O)c5c(O)c6/N=N/c(cccc5)c5C(O)=O)nc(O)n4)=O)=O)nc(O)n3)cc(S(O)(=O)=O)c1)c2O Chemical compound CC(CC=C1C(O)=O)C=C1/N=N/c(c(S(O)(=O)=O)cc1c2c(Nc3nc(NNC(c(cc4)ccc4C(NNc4nc(Nc(cc(cc5cc6S(O)(=O)=O)S(O)(=O)=O)c5c(O)c6/N=N/c(cccc5)c5C(O)=O)nc(O)n4)=O)=O)nc(O)n3)cc(S(O)(=O)=O)c1)c2O TXZFHNVNJBPRDS-JEAZKISVSA-N 0.000 description 1
Classifications
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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
- 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
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
Definitions
- This invention relates to dyes, to inks and to their use in ink jet printing ("UP").
- UP is a non-impact printing technique in which droplets of ink are ejected through a fine nozzle onto a substrate without bringing the nozzle into contact with the substrate.
- the inks are often required to dry quickly when applied to a substrate to prevent smudging, but they should not form a crust over the tip of an ink jet nozzle because this will stop the printer from working.
- the inks should also be stable to storage over time without decomposing or forming a precipitate which could block the fine nozzle.
- liquid medium comprises water and an organic solvent, an organic solvent free from water, or a low melting point solid.
- the compound is red, orange, yellow, green, blue, indigo, violet or black.
- the compound comprises from 1 to 8 groups selected from hydrazine and hydrazide groups, more preferably 1 , 2, 3 or 4, especially 1 or 2, more especially 2 groups selected from hydrazine and hydrazide groups.
- the compound may contain both hydrazine and hydrazide groups.
- the hydrazine and hydrazide groups preferably comprise a group of the Formula
- Preferred hydrazine and hydrazide groups of Formula (2) are of Formula (2a) or (2b) as follows:
- Q 1 and Q 2 are each independently H, optionally substituted alkyl or optionally substituted aryl, or Q 1 and Q 2 together with the nitrogen atoms to which they are attached form an optionally substituted 5- or 6- membered ring;
- Q 3 together with the nitrogen atom to which it is attached forms an optionally substituted 5- or 6- membered ring; and Q 4 is H, optionally substituted alkyl or optionally substituted aryl.
- p is 1 or 2, more preferably 1.
- Examples of hydrazine groups of Formula (2a) include those listed later in this specification in Table 2, Examples 17, 20, 23, 25, 26, 27, 28, 29, 31 , 33, 34, 35 and 37.
- Examples of hydrazide groups of Formula (2a) include those listed later in this specification in Table 2, Examples 8, 9, 10, 11 , 12, 13, 14, 15, 16, 18, 19, 24, 30, 32 and 38. Examples of hydrazine groups of Formula (2b) include those listed in Table 5,
- Example 134 and Table 1 , Example 36.
- Examples of hydrazide groups of Formula (2b) include the group listed in Table 5, Example 127.
- Q 1 , Q 2 and Q 4 are each independently H or C ⁇ -alkyl, more preferably H.
- the compound further comprises one or two triazine groups.
- at least one (more preferably all) of the hydrazine and hydrazide groups is located in the compound such that it is connected directly to a triazine ring by one covalent bond.
- the compound further comprises one or more water solubilising groups. Preferred water-solubilising groups are sulpho, carboxy and phosphato.
- the compound has at least one carboxy group, more preferably 1 to 8 carboxy groups, especially 1 to 4 carboxy groups. In one embodiment the compound has at least as many carboxy groups as sulpho groups.
- the compound may be in free acid form or in the form of a salt with a cation or mixture of cations.
- Preferred cations include alkali metals, especially lithium, sodium and potassium, and ammonium and substituted ammonium (e.g. tetramethylammonium or ethylammonium).
- the compound is free from fibre reactive groups, e.g. free from halotriazine groups, because such groups are not needed in the compounds.
- halotriazine groups may hydrolyse when stored in an ink to release acid and reduce storage stability of the ink.
- composition comprises a compound which:
- the compound is preferably of Formula (3) or a salt thereof:
- each D independently is a chromophoric group; n is at least one; R 1 is H or a substituent; and L is an organic group of valency n; provided that:
- the compound comprises one or more hydrazide or hydrazine group, preferably of Formula (2), more preferably of Formula (2a) or (2b), as hereinbefore defined; and (ii) the compound is free from groups of Formula (1) and salts thereof, as hereinbefore defined.
- the hydrazine and hydrazide group preferably forms part of L and/or R 1 .
- the hydrazine or hydrazide group is attached directly to the triazine ring shown in Formula (3).
- n is 1 , 2, 3 or 4, more preferably 1 , 2 or 3, especially 1 or 2.
- Each D independently is preferably an azo (especially mono azo or disazo), formazan, metallised azo, methine, azamethine, xanthene, triphenyl methane, phthalocyanine or anthraquinone chromophore or a combination thereof.
- Preferred azo chromophores represented by D are of the Formula (4):
- Ar is optionally substituted aryl
- Y is optionally substituted arylene
- Z is O, S, a hydrazine group, a hydrazide group or NR 2 ;
- R 2 is H, optionally substituted alkyl, optionally substituted aryl or optionally substituted acyl; provided that the group of Formula (4) is free from groups of Formula (1 ) and salts thereof.
- Ar is preferably optionally substituted phenyl, optionally substituted naphthyl or optionally substituted benzthiazolyl.
- Y is preferably optionally substituted phenylene or optionally substituted naphthylene.
- each Ar has a substituent at the 2-position relative to the azo group shown in Formula (4).
- this 2-substituent is -SO 3 H or -CO 2 H.
- R 1 is H, OH, a chromophoric group, halo, optionally substituted alkyl, -NR 3 R 4 , -N(Q 1 )-N(Q 2 )R 2 , -OR 2 or -SR 2 ; wherein: each R 2 , Q 1 and Q 2 independently is as hereinbefore defined; each R 3 and R 4 independently is H, optionally substituted alkyl, optionally substituted aryl or optionally substituted acyl, 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.
- R 1 Preferred halo groups represented by R 1 include F and Cl.
- R 1 is -NR 3 R 4 it is preferred that each R 3 and R 4 independently is H, optionally substituted alkyl, optionally substituted aryl or optionally substituted heterocyclyl, 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.
- R 1 groups are OH, Cl, -NR 3 R 4 and -N(Q )-N(Q 2 )R 2 wherein R 2 , R 3 , R 4 , Q 1 and Q 2 are as hereinbefore defined.
- groups represented by R 1 include -NHCH 2 CHOHCH 2 OH,
- L is preferably an organic linking group (especially a divalent organic linking group) comprising a sulphur, oxygen or nitrogen atom at one or both ends, more preferably an amino group of formula -NR 2 - or a hydrazine or hydrazide group at one or both ends.
- Preferably L comprises from 2 to 20, more preferably from 2 to 10 carbon atoms.
- L is preferably of the formula -X 1 -(L 1 -X 2 ) m - wherein: m is O or l ;
- L is an optionally substituted, optionally interrupted alkylene group or an optionally substituted arylene group; and X 1 and X 2 are each independently of the formula -NR 2 - or a hydrazine or hydrazide group.
- L 1 is an optionally substituted, optionally interrupted alkylene group, it is preferably optionally substituted, optionally interrupted C ⁇ -alkylene.
- L 1 is preferably -CO-C,. 20 -alkylene-CO- or -C.,.
- L 1 When L 1 is interrupted, it preferably contains 1 to 5 interrupting groups, more preferably one or two interrupting groups.
- the interrupting groups may be part way along the alkylene group (e.g. -CH 2 COCH 2 ) or at the end of the alkylene group (e.g. -CO(CH 2 ) 2 CO).
- L 1 is an optionally substituted arylene group
- the optional substituents are as previously described.
- the arylene group is unsubstituted, and is a phenylene group, especially 1 ,4-phenylene.
- Examples of suitable groups represented by L include:
- R 1 , R 2 , R 3 , R 4 , Q 1 , Q 2 or Q 4 is optionally substituted, alkyl, it is preferably C,_ 2 o-alkyl, more preferably C ⁇ . 10 -alkyl, especially C ⁇ -alkyl, more especially C ⁇ -alkyl, each of which is optionally substituted and optionally interrupted.
- the optional substituents are preferably selected from C ⁇ -alkoxy, halo (preferably F or Cl) C,. 6 -hydroxy alkoxy, -OH, -CO 2 H, -SO 3 H, -PO 3 H 2 , -CN, optionally substituted phenyl, a 5- or 6- membered heterocyclic group and optionally substituted amino.
- Preferred 5- or 6-membered rings and heterocyclic groups include furanyl, pyranyl, pyridyl, pyridinium, tetrahydrofuranyl, thiophenyl and carboxymethyl thiophenyl.
- R 2 , R 3 , R 4 , Q ⁇ Q 2 or Q 4 is optionally substituted aryl it is preferably optionally substituted phenyl, naphthyl, thiazolyl, pyridyl, furanyl or pyranyl, more preferably optionally substituted phenyl.
- the optional substituents are preferably selected from halo (preferably F or Cl), OH, -CN, -CO 2 H, -SO 3 H, -PO 3 H 2 , -NO 2 , -NH 2 , -COC ⁇ -alkyl, -NHCOC M -alkyl, -(C 1 . 6 -alkylene)O(C 1 ⁇ -alkylene)OC M -alkyl, -(C 2 ⁇ - alkylene)OC 2 . 6 -alkyleneOH, -SO 2 NH 2 , -SO 2 NHC M -alkyl, C ⁇ -alkyl and C ⁇ -alkyl substituted by OH, -CO 2 H or -SO 3 H.
- halo preferably F or Cl
- R 1 , R 2 , R 3 , R 4 , Q 1 , Q 2 or Q 4 is alkyl substituted by an optionally substituted phenyl group, it is preferably an aralkyl group of the formula : wherein: each R 6 independently is C M -alkyl, C 1 . 4 -alkoxy, halo, -OH, -NH 2 , -CO 2 H, -SO 3 H, or -PO 3 H 2 ; and a is 0 to 5.
- a is 0, 1 or 2.
- Especially preferred aralkyl groups are benzyl and 2-phenylethyl, each of which is optionally substituted by -CO 2 H, -OH or -SO 3 H.
- R 3 and R 4 together with the nitrogen to which they are attached form an optionally substituted ring it is preferably an optionally substituted 5- or 6- membered ring, more preferably a piperazinyl, piperidinyl or morpholinyl ring.
- the optional substituents are preferably selected from -OH, -CO 2 H, -SO 3 H, -C ⁇ -alkoxy, -C ⁇ -alkyl and -C ⁇ -alkyl substituted by -OH, -CO 2 H or -SO 3 H.
- R 2 , R 3 , R 4 , Q 1 , Q 2 and Q 4 are preferably each independently H or C ⁇ -alkyl.
- Preferred compounds are of Formula (3) are of Formula (3a), (3b), (3c) or (3d):
- the compound comprises a single group of Formula (1) or a salt thereof the compound is preferably of Formula (5) or a salt thereof:
- D is H or chromophoric group
- Ar, L and R 1 are as hereinbefore defined; provided that: (i) the compound comprises one or more hydrazine or hydrazide groups, preferably of Formula (2), more preferably of Formula (2a) or (2b), as hereinbefore defined; (ii) the compound has a single group of Formula (1) or salt thereof, as hereinbefore defined.
- the hydrazine or hydrazide group preferably forms part of -L-D and/or R 1 , preferably being attached directly to the triazine ring shown in Formula (5).
- L is preferably a divalent organic linking group, more preferably a divalent organic linking group comprising a sulphur, oxygen or nitrogen atom at each end, especially an amino group of formula -NR 4 or a group of Formula (2a) at one or both ends.
- L contains from 2 to 20 carbon atoms more preferably 2 to 10 carbon atoms.
- compounds of Formula (5) L is preferably of the formula:
- m is O or ;
- L 1 is as hereinbefore defined; and X 3 and X 4 are each independently O, S, of the formula -NR 4 or Formula (2) (especially (2a)) as hereinbefore defined.
- Z 2 is O, S or NR 4 ;
- R 4 is H, optionally substituted alkyl, optionally substituted aryl or optionally substituted acyl; and Ar, L 1 , R 1 , Q 2 , Q 3 , Q 4 and D are as hereinbefore defined and preferred; provided that the compounds of Formula (5a), (5b), (5c) and (5d) comprise a single group of Formula (1) or salt thereof.
- Preferred optionally substituted alkyl, optionally substituted aryl and optionally substituted acyl groups represented by R 4 in compounds of Formula (5) are as hereinbefore described.
- D is H, an azo (especially mono azo or disazo), formazan, metallised azo, methine, azamethine, xanthene, triphenyl methane, phthalocyanine or anthraquinone chromophore or a combination thereof.
- R 1 is H, OH, halo, optionally substituted alkyl, -NR 3 R 4 , -N(Q 1 )-N(Q 2 )R 2 , -OR 2 , -SR 2 or of Formula (2b) as hereinbefore defined wherein p is 0; wherein R 2 , R 3 , R 4 , Q 1 and Q 2 are as hereinbefore defined.
- D is preferably H or an azo (especially mono azo or disazo), formazan, xanthine, methine, azomethine, metallised azo, phthalocyanine or anthraquinone chromophore.
- Preferred azo chromophores represented by D are of the Formula (6) or a salt thereof:
- m is 0 or 1 and Ar independently is as hereinbefore defined, provided that D is not and does not comprise a group of Formula (1) as hereinbefore defined.
- At least one of the hydrazine or hydrazide groups forms part of an in chain link between the group of Formula (1) and a chromophoric group other than a group of Formula (1).
- at least one of the hydrazine or hydrazide groups are not part of an in chain link between the group of Formula (1) and a chromophoric group other than a group of Formula (1).
- the compound of the present invention comprises two or more groups of the Formula (1 ) or salts thereof the compound is preferably of Formula (7) or a salt thereof:
- the compound comprises one or more hydrazine or hydrazide groups, preferably of Formula (2), more preferably of Formula (2a) or (2b), as hereinbefore defined.
- the hydrazine or hydrazide group preferably forms part of -L and/or R 1 , preferably being attached directly to the triazine ring shown in Formula (7).
- preferred compounds of Formula (7) are of the Formula (7a), (7b), (7c) or
- n 2 or more.
- n is preferably 2, 3 or 4, more preferably 2 or 3, especially 2.
- this chromophoric group is preferably H or an azo (especially mono azo or disazo), formazan, xanthine, methine, azomethine,
- L5 metallised azo, phthalocyanine or anthraquinone chromophore are of the Formula (6) as previously defined.
- Ar is phenyl or naphthyl having 0, 1 , 2 or 3 substituents selected from the group consisting of carboxy, sulpho and C ⁇ -alkyl; and R 1 is H or C ⁇ -alkyl.
- the compounds may exist in tautomeric forms other than those shown in this specification, for example the hydrazo tautomer. These tautomers are included within the
- component (b) is completely dissolved in component (a).
- component (b) has a solubility in component (a) at 20°C of at least 10%. This allows the
- 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
- L5 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, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol and thiodiglycol and oligo- and poly-alkyleneglycols, preferably diethylene glycol, triethylene glycol,
- triols preferably glycerol and 1 ,2,6-hexanetriol
- mono-C M -alkyl ethers of diols preferably mono-C ⁇ -alkyl ethers of diols having 2 to 12 carbon atoms, especially 2-methoxyethanol, 2-(2-methoxyethoxy)ethanol, 2-(2-ethoxyethoxy)-ethanol, 2-[2-(2-methoxyethoxy)ethoxy]ethanol, 2-[2-(2-ethoxyethoxy)- ethoxyj-ethanol and ethyleneglycol monoallylether; cyclic amides, preferably 2-pyrrolidone,
- the liquid medium comprises water and 2 or more, especially from 2 to 8, water- miscible organic solvents.
- Especially preferred water-soluble miscible organic solvents are cyclic amides, i o 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 M -alkyl ethers of diols, more preferably mono- C ⁇ -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
- the solvent preferably has a boiling point of from 30° to 200°C, more preferably of from 40° to 150°C, especially from 50 to 125°C.
- the organic solvent may be water-immiscible, water-miscible or a mixture of such solvents.
- Preferred water- miscible organic solvents are any of the hereinbefore described water-miscible organic solvents and mixtures thereof.
- 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 liquid medium comprises a water-immiscible organic solvent
- a polar solvent is included because this enhances solubility of the dye in the liquid medium.
- polar solvents include C ⁇ -alcohols.
- the liquid medium is an organic solvent free from water it comprises a ketone (especially methyl ethyl ketone) &/or an alcohol (especially a C,. 4 -alkanol, more especially ethanol or propanol).
- 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.
- Liquid 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
- Suitable low melting point solids include long chain fatty acids or alcohols, preferably those with C 18 . 24 chains, and sulphonamides.
- the compounds defined in the first aspect of the invention may be dissolved in the low melting point solid or may be finely dispersed in it.
- the composition may also contain additional components conventionally used in ink jet printing inks, for example viscosity and surface tension modifiers, corrosion inhibitors, biocides, kogation reducing additives and surfactants which may be ionic or non-ionic.
- the composition may be used as a concentrate to make ink jet printing inks or, more preferably, the composition is an ink, especially an ink jet printing ink.
- compositions may be, and preferably are, purified to remove undesirable impurities. Conventional techniques may be employed for purifying the compounds, for example ultrafiltration, reverse osmosis and/or dialysis.
- compositions of the present invention preferably have a total concentration of divalent and trivalent metal ions of less that 500 ppm, more preferably less than 100 ppm, especially less than 20 ppm, where ppm refers to parts per million by weight.
- composition of the present invention have been filtered through a filter having a mean pore size below 10 ⁇ m, more preferably below 2 ⁇ m, especially below 1 ⁇ m.
- a filter having a mean pore size below 10 ⁇ m, more preferably below 2 ⁇ m, especially below 1 ⁇ m.
- the preferences described above in relation to the preferred compounds to be included in the compositions according to the first aspect of the present invention also apply to the compounds per se according to the second aspect of the present invention.
- the preferences for the compounds of the second aspect of the present invention are as hereinbefore described for the compounds used as component (b) according to the first aspect of the present invention (especially preferred are the compounds of Formulae (3), (5) and (7)) provided that the compound is in all cases free from halotriazine groups.
- the compounds of the invention may be prepared by methods analogous to those used in the field of ink jet printing except that at least one of the starting materials is selected which contains a hydrazine and/or hydrazide group and which is (i) either free from groups of Formula (1) or salts thereof; (ii) comprises a single group of Formula (1) or a salt thereof; or (iii) comprises two or more groups of Formula (1) or salts thereof in the compound.
- known compounds having labile groups and one group of Formula (1) e.g. reactive dyes as disclosed in the Colour Index International, may be condensed with hydrazine or hydrazide compounds at pH below 7.
- the Examples described later in this specification illustrate more specifically the reaction conditions which may be employed to make compounds of the invention.
- a third aspect of the invention provides a process for the coloration of a substrate comprising applying thereto by means of an ink jet printer a composition according to the first aspect of the present invention or a compound according to the second aspect of the present invention.
- the ink jet printer preferably applies the composition to the substrate in the form of droplets which are ejected through a small orifice onto the substrate.
- Preferred ink jet printers are piezoelectric ink jet printers and thermal ink jet printers.
- thermal ink jet printers programmed pulses of heat are applied to the composition in a reservoir by means of a resistor adjacent to the orifice, thereby causing the composition to be ejected in the form of small droplets directed towards the substrate during relative movement between the substrate and the orifice.
- the oscillation of a small crystal causes ejection of the composition from the orifice.
- the substrate is preferably paper, plastic, a textile, metal or glass, more preferably paper, an overhead projector slide, especially paper, more especially a porous paper.
- Preferred papers are plain or treated papers (especially porous papers) which may have an acid, alkaline or neutral character.
- Examples of commercially available treated papers include HP Premium Coated Paper, HP Photopaper (all available from Hewlett Packard Inc.), Stylus Pro 720 dpi Coated Paper, Epson Premium Glossy Photopaper. Epson Photo Quality Gloss Film, Epson Photo Quality Glossy Paper (available from Seiko Epson Corp.), Canon HR 101 High Resolution Paper, Canon GP 201 Glossy Paper, Canon HG 101 High Gloss Film (all available from Canon Inc.), Wiggins Conqueror Paper (available from Wiggins Teape Ltd), Xerox Acid Paper and Xerox Alkaline Paper, Xerox Acid Paper (available from Xerox).
- Preferred porous papers comprise;
- the binder resin preferably comprises polyvinylalcohol, polyvinyl pyrrolidone or a mixture thereof.
- porous papers arises because these papers, in combination with the compounds and compositions of the present invention, lead to prints having particularly good light-fastness properties.
- porous papers arises because these papers, in combination with the compounds and compositions of the present invention, lead to prints having particularly good light-fastness properties.
- a fourth aspect of the present invention provides a substrate, preferably a paper, a slide or a textile material printed with a composition according to the first aspect of the present invention, by a compound according to the second aspect of the present invention, or by means of a process according to the third aspect of the present invention.
- an ink jet printer cartridge comprising a chamber and ink, wherein the ink is present in the chamber and the ink comprises a composition according to the first aspect of the present invention or a compound according to the second aspect of the invention.
- an ink jet printer containing an ink jet printer cartridge, wherein the ink jet printer cartridge is as defined in the fifth aspect of the present invention.
- Example 1 The invention is further illustrated by way of the following examples in which all parts and percentages are by weight unless otherwise stated.
- Example 1
- stage (a) (40g) was stirred in de-ionised water (350ml) along with H 2 NNHCONH 2 (14.1g) at ⁇ 30°C, whilst the pH was maintained at -8.5 using 2N sodium hydroxide. Progress of the reaction was found to be satisfactory by HPLC after -10 hours reaction time.
- the product was then cooled to room temperature and isolated by addition to Methylated Spirits 74 OP (-2.5I), and filtered through GF/A filter paper then pulled 'fairly dry.
- the resultant solid was re-dissolved in de-ionised water ( ⁇ 300ml) and dialysed to low conductivity using visking tubing.
- the resultant solution was filtered through GF/A, then GF/F filter paper and finally through Nylon 0.45 microns.
- the resultant solution was evaporated to dryness under reduced pressure, giving the title product as a magenta solid (32.4g).
- Example 1 The method of Example 1 was repeated except that in place of H 2 NCH 2 CHOHCH 2 OH there was used an equimolar amount of H 2 NCH 2 CH 2 SO 3 H.
- Example 1 The method of Example 1 was repeated except that in place of H 2 NCH 2 CHOHCH 2 OH there was used an equimolar amount of HN(CH 2 CO 2 H)(H 2 PO 3 H 2 ) and in place of H 2 NNHCONH 2 there was used H 2 NNHCOCONH 2 .
- Example 3 The compound from Example 3 was made up into an ink according to the formulation shown below. For comparison purposes a compound lacking the hydrazo (-NH-NH-) group, shown below as Comparative Dye (X), was made into an identical ink:
- the ink formulation had a pH8 and the following components (all parts by weight) Component Amount
- Table 1 shows that compounds of the invention have higher light fastness (lower ⁇ E) than Comparative Dye (X).
- Oxamic hydrazide (1 part) was added to a solution of the dichorotriazine Opart) and the pH of the mixture raised to 8.5 with 2M sodium hydroxide solution. The temperature was allowed to rise to 20-25°C and the mixture stirred at pH 8.5/20-25°C for 2.5 hours.
- Stage c ' 1 ,4-diazabicyclo[2.2.2]octane (0.01parts) was added to a solution of the monochlorotraizine in water (1 part in 10) and the pH was raised to 10.5-11.0 with 2M sodium hydroxide solution. The mixture was heated to 80-85°C and held there until the hydrolysis was complete. Sodium chloride was added to 10% w/v and the pH brought to 7 with concentrated hydrochloric acid. The mixture was cooled to 60°C, the product was filtered off and washed with 15%w/v sodium chloride solution.
- the wet product was dissolved in dilute sodium hydroxide solution and dialysed in visking tubing to low ' conductivity.
- the dialysed solution was screened through a 0.7 ⁇ m filter and the solution evaporated to dryness at 50°C to give the title compound.
- the resultant compound had a ⁇ max at 553 nm.
- Example 7 The method of Example 7 was repeated except that in step (b), in place of oxamic hydrazide there was used an equimolar amount of the hydrazine specified in Table 2, column 2.
- the resultant compound was of Formula (A1) wherein R 1 and -L-D are as specified in Table 2.
- Example 7 The method of Example 7 was repeated except that in stage (b) place of oxamic hydrazide there was used an equivalent amount of the hydrazine compound specified in Table 3, column 2, and stage (c) was replaced by condensation of the product of stage (b) (1 part) in water (10 parts) at 85°C with the nucleophile (3 parts) listed in Table 3, column 3.
- the resultant compound was of the Formula (A1) wherein R and -L-D are as specified in Table 3. • Table 3
- Example 7 The method of Example 7 was represented except that in stage (a) place of 2- carboxy aniline the compound specified in Table 5, column 3 was used in an equimolar amount; and in stage (b) in place of oxamic acid there was used an equimolar amount of the hydrazine in Table 5, column 6.
- Example 7 The method of Example 7 was repeated except that in stage (a) in place of 2- carboxy aniline the compound specified in Table 6, column 2 was used in an equimolar amount; in stage (b) in place of oxamic acid there was used an equimolar amount of the hydrazine in Table 6, column 7; and stage (c) was replaced by condensation of the product of stage (b) (1 part) in water (10 parts) at 85°C with the nucleophile listed in Table 6, column 5.
- Example 7 The compound from Example 7 was made up into an ink according to the formulation shown below.
- a compound lacking the hydrazo (- NH-NH-) group shown below as Comparative Dye (X), was made into an analogous ink:
- the ink Formulation had a pH8 and the following components (all parts by weight):
- Oxalic acid dihydrazide (2.74 parts) was added and the pH of the mixture raised to 8.5 with 2M sodium hydroxide solution. The temperature was allowed to rise to 20-25°C and the mixture stirred at pH 8.5/20-25°C for 2.5 hours. 1 ,4-diazabicyclo[2.2.2]octane (0.2g) was added and the pH was raised to 10.5-11.0 with 2 sodium hydroxide solution. The mixture was heated to 80-85°C and held there until the hydrolysis was complete. Sodium chloride was added to 10% w/v and the pH brought to 7 with concentrated hydrochloric acid. The mixture was cooled to 60°C, the product was filtered off and washed with 15%w/v sodium chloride solution. The wet product was dissolved in dilute sodium hydroxide solution and dialysed in visking tubing to low conductivity. The dialysed solution was screened through a 0.7 ⁇ m filter and the solution evaporated to dryness at 50°C to give the title compound.
- Example 144 to 148 The method of Example 143 was repeated except that in place of the component(s) listed in Table 8, column 2, there was used an equimolar amount of the component(s) listed in column 3.
- the resultant compound was of Formula (B1) wherein Ar and L 1 are as shown in Table 8.
- the title compound was prepared as described in Example 143 except that in place of oxalic acid dihydrazide there was used an equimolar amount of pterephthaloyl dihydrazide and the hydrolysation step was omitted.
- the resultant compound had a ⁇ max at 548nm.
- Example 143 The method of Example 143 was repeated except that (i) oxalic acid dihydrazide was replaced by an equimolar amount of [(CH ⁇ CONHNHJ;, and the hydrolysation step was replaced by condensation of the resultant chlorotriazine compound (1 part) with the amine indicated in Table 10, column 2 below (3 parts) in water at 80°C for 4 hours.
- 2-Napthylamine-1-sulphonic acid (67.84g) was added to water (500ml) and cooled to 0-5°C. Concentrated HCI (150ml) was then added followed by 2N NaNO 2 (150ml). The solution was stirred for 1 hour at 0-5°C and excess NaNO 2 was destroyed by addition of sulphamic acid.
- stage (i) above 86.5g was dissolved in water (800ml). Cyanuric chloride (19.36g) was dissolved in acetone (200ml) and added to ice/water (300g). To this was added the solution of the product of stage (i) allowing the pH to fall. The resulting solution was stirred for 2 hours at 0-5°C. The pH was then raised to 7.0 by addition of 2N NaOH solution and the solution was allowed to self warm to room temperature. This gave a dichorotriazine compound.
- Adipic dihydrazide (0.5 parts) was added to a solution of the dichlorotriazine product from stage (ii) (1 part) in water (10 parts) and the pH of the mixture raised to 8.5 with 2M sodium hydroxide solution. The temperature was allowed to rise to 20-25°C and the mixture stirred at pH 8.5/20-25°C for 2.5 hours to give the title product.
- Example 161 to 166 The resultant compounds were of Formula (E) wherein R 4 and L 1 are as described in Table 11 below. These compounds were prepared by condensing 3 parts of the nucleophile listed in column 2 of Table 11 with 1 part of the product of Example 160 in water (10 parts) at 85°C for 4 hours.
- Example 160 The method of Example 160 was repeated except that in place of [(CHz ⁇ CONHNHJz there was used an equimolar amount of (oxalyl dihydrazide) 2 .
- the resultant chlorotriazine compound (1 part) in water (10 parts) was condensed with H 2 NCH 2 CHOHCH 2 OH (2 parts) at 80°C for 4 hours to give the compound of Formula (E) wherein R 4 is HNCH 2 CHOHCH 2 OH and L is -COCO- having ⁇ max at 542 nm.
- Example 168 The method of Example 168 was repeated except that in place of [(CH 2 ) 2 CONHNH 2 ] 2 there was used on equimolar amount of [(CH 2 )CONHNH 2 ] 2 .
- the resultant compound had a ⁇ max at 545nm.
- Example 160 The method of Example 160 was repeated except that in place of
- Cystine (2.74 parts) was added and the pH of the mixture raised to 8.5 with 2M sodium hydroxide solution. The temperature was allowed to rise to 20-25°C and the mixture stirred at pH 8.5/20-25°C for 2.5 hours. Octanoic hydrazide (15 parts) was added and the pH was raised to 10.5-11.0 with 2M sodium hydroxide solution. The mixture was
- Example 173 The method of Example 171 was repeated except that in place of octanoic hydrazide there was used an equimolar amount of ethanoic hydrazide. The resultant compound had a ⁇ max at 545nm.
- Example 173
- Example 173 The method of Example 173 was repeated except that in place of omithine there was used an equimolar amount of 1 ,3-diamino-2-hydroxy propane and in place of benzoyl hydrazide there was used an equimolar amount of ethanoyl hydrazide.
- the resultant compound had a ⁇ max at 551 nm.
- Example 143 The compound from Example 143 and Comparative Dye (X) were made up into an ink according to the general formulation described in Example 142 above.
- the inks were placed in a Canon 4300 ink jet printer and printed onto the papers indicated in Table 12 below. After drying, the light-fastness of the prints were measured by the general method described in Example 142 above and the results are shown in Table 12 below:
- Table 12 shows that Compound from Example 143 has higher light-fastness (lower ⁇ E) than Comparative Dye (X).
- stage (a) 29. Og, 0.05 moles was suspended in water (800mls) and dissolved by the addition of sodium hydroxide (2M) to pH7. The mixture was then cooled to ⁇ 5°C and a slurry of cyanuric chloride (10.2g, 0.055 moles) in water (50mls) and calsolene oil (0.1g) was added. The resultant mixture was stirred at below 5°C for 2 hours maintaining the pH of the mixture at between pH 6.5 and 7.0 by the addition of sodium hydroxide solution (2M) as required.
- 2M sodium hydroxide solution
- Pterepthaloyl hydrazide (from Aldrich) (4.8g (0.0275 moles) was added to the product of stage (a) and the pH of the mixture raised to pH 8.5 using sodium hydroxide solution (2M). The temperature of the reaction mixture was allowed to rise to 20-25°C and then the mixture was stirred at pH 8.5 at 20-25°C for 2.5 hours.
- the mixture was then cooled to 60°C and the product filtered and washed with 15% w/v sodium chloride solution.
- the resultant wet product was subsequently dissolved in dilute sodium hydroxide solution and dialysed in visking tubing to low conductivity.
- the dialysed solution was screened through a 0.7 ⁇ m filter and the solution evaporated to dryness at 50°C to give Compound (A3) having a ⁇ max at 551 nm.
- Compound (B2) was prepared by the method described in Example 178 except that in place of 4-methyl-2-sulphoaniline there was used 2-carboxyaniline and in place of pterephthaloyl hydrazide there was used isophthaloyl hydrazide.
- Compound (C1) was prepared by the method described in Example 178 except that in place of 4-methyl-2-sulphoaniline there was used 2-carboxy aniline.
- Compound (D1) was prepared according to the method of Example 178 except that in place of pterephthaloyl hydrazide there was used isophthaloyl hydrazide.
- Example 182 Compound (E1 )
- Compound (E1) was prepared according to the method of Example 178 except that in place of 4-methyl-2-sulphoaniline there was used 4-methyl-2-carboxyaniline to give Compound (E1) having a ⁇ max at 550nm.
- Table 13 shows that Compounds (B2) and (C1) have higher light-fastness (lower
- the inks described in Tables 14 to 22 may be prepared wherein the compound described in the first column is the compound described in the above examples.
- Numbers quoted in the second column onwards refer to the number of parts of the relevant ingredient and all parts are by weight.
- the inks may be applied to paper by thermal or piezo ink jet printing.
- NMP N-methyl pyrollidone
- MIBK methylisobutyl ketone
- TBT tertiary butanol
- TDG thiodiglycol
- Proxel XL-2 biocide from Avecia Inc.
- DGM diethylene glycol monobutyl ether
- TEG triethylene glycol monobutyl ether
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0319749A GB2389588B (en) | 2001-03-03 | 2002-02-27 | Ink jet printing composition comprising a dye containing hydrazide groups |
US10/469,309 US7141106B2 (en) | 2001-03-03 | 2002-02-27 | Ink jet printing composition comprising a dye containing hydrazine or hydrazide |
Applications Claiming Priority (18)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0105321A GB0105321D0 (en) | 2001-03-03 | 2001-03-03 | Composition |
GB0105321.4 | 2001-03-03 | ||
GB0105325A GB0105325D0 (en) | 2001-03-03 | 2001-03-03 | Composition |
GB0105328A GB0105328D0 (en) | 2001-03-03 | 2001-03-03 | Composition |
GB0105324.8 | 2001-03-03 | ||
GB0105325.5 | 2001-03-03 | ||
GB0105324A GB0105324D0 (en) | 2001-03-03 | 2001-03-03 | Compounds and inks |
GB0105328.9 | 2001-03-03 | ||
GB0106007A GB0106007D0 (en) | 2001-03-12 | 2001-03-12 | Composition |
GB0106007.8 | 2001-03-12 | ||
US30416201P | 2001-03-21 | 2001-03-21 | |
US81330001A | 2001-03-21 | 2001-03-21 | |
US30417601P | 2001-03-21 | 2001-03-21 | |
US30416101P | 2001-03-21 | 2001-03-21 | |
US60/304,162 | 2001-03-21 | ||
US60/304,176 | 2001-03-21 | ||
US09/813,300 | 2001-03-21 | ||
US60/304,161 | 2001-03-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002070609A1 true WO2002070609A1 (en) | 2002-09-12 |
WO2002070609A8 WO2002070609A8 (en) | 2004-04-08 |
Family
ID=27576264
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2002/000810 WO2002070609A1 (en) | 2001-03-03 | 2002-02-27 | Ink jet printing composition comprising a dye containing hydrazine or hydrazide |
Country Status (2)
Country | Link |
---|---|
GB (1) | GB2389588B (en) |
WO (1) | WO2002070609A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6712462B2 (en) | 2001-05-14 | 2004-03-30 | Seiko Epson Corporation | Ink set and ink jet recording method |
US6779881B2 (en) | 2001-09-13 | 2004-08-24 | Seiko Epson Corporation | Ink, ink set, and ink jet recording method |
US7476260B2 (en) | 2004-04-08 | 2009-01-13 | Ciba Specialty Chemicals Corp. | Disulfide dyes, composition comprising them and method of dyeing hair |
CN107475724A (en) * | 2017-07-06 | 2017-12-15 | 广东石油化工学院 | Nitrogenous organic phosphorous acids corrosion inhibiter and synthetic method |
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GB751997A (en) * | 1953-03-30 | 1956-07-04 | Gen Aniline & Film Corp | Triazine dyes for cotton containing carbamyl hydrazide and its imido and thio analogues |
GB921250A (en) * | 1960-02-13 | 1963-03-20 | Basf Ag | New dyes of the tetrazaporphin series |
GB924258A (en) * | 1960-02-13 | 1963-04-24 | Basf Ag | Dyes of the anthraquinone, perylene tetracarboxylic acid diimide, pyrene-quinone and perinaphthalene tetracarboxylic acid diimide series |
GB929097A (en) * | 1960-02-13 | 1963-06-19 | Basf Ag | New monoazo dyes containing hydrazinyl substituted triazine residues |
GB941009A (en) * | 1961-02-16 | 1963-11-06 | Basf Ag | Dyes containing hydrazino groups |
GB962017A (en) * | 1961-03-24 | 1964-06-24 | Durand & Huguenin Ag | New water-soluble leuco-sulphuric acid ester salts of vat dyestuffs of the anthraquinone series and a process of the anthraquinone series and a process of making same |
US4420627A (en) * | 1981-12-18 | 1983-12-13 | Polaroid Corporation | Hydrazine dyes |
US4742160A (en) * | 1983-11-14 | 1988-05-03 | Sandoz Ltd. | Sulfo group-containing basic azo compounds having a central 1,3,5-triazine ring and two terminal 1-hydroxynaphthyl-2 groups and 1:1 and 1:2 metal complexes therof |
EP0312004A2 (en) * | 1987-10-13 | 1989-04-19 | Hoechst Aktiengesellschaft | Use of colouring agents in recording fluids |
US5495003A (en) * | 1993-01-30 | 1996-02-27 | Sandoz Ltd. | 2,2'-disulfo-4,4'-substituted triazinylaminophenyl disazostilbenes |
Family Cites Families (3)
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BE639274A (en) * | 1962-10-30 | |||
DE2751137A1 (en) * | 1977-11-16 | 1979-05-17 | Bayer Ag | REACTIVE COLORS |
JPH01198750A (en) * | 1988-02-03 | 1989-08-10 | Konica Corp | Processing method for silver halide color photographic sensitive material |
-
2002
- 2002-02-27 WO PCT/GB2002/000810 patent/WO2002070609A1/en not_active Application Discontinuation
- 2002-02-27 GB GB0319749A patent/GB2389588B/en not_active Expired - Fee Related
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB751997A (en) * | 1953-03-30 | 1956-07-04 | Gen Aniline & Film Corp | Triazine dyes for cotton containing carbamyl hydrazide and its imido and thio analogues |
GB921250A (en) * | 1960-02-13 | 1963-03-20 | Basf Ag | New dyes of the tetrazaporphin series |
GB924258A (en) * | 1960-02-13 | 1963-04-24 | Basf Ag | Dyes of the anthraquinone, perylene tetracarboxylic acid diimide, pyrene-quinone and perinaphthalene tetracarboxylic acid diimide series |
GB929097A (en) * | 1960-02-13 | 1963-06-19 | Basf Ag | New monoazo dyes containing hydrazinyl substituted triazine residues |
GB941009A (en) * | 1961-02-16 | 1963-11-06 | Basf Ag | Dyes containing hydrazino groups |
GB962017A (en) * | 1961-03-24 | 1964-06-24 | Durand & Huguenin Ag | New water-soluble leuco-sulphuric acid ester salts of vat dyestuffs of the anthraquinone series and a process of the anthraquinone series and a process of making same |
US4420627A (en) * | 1981-12-18 | 1983-12-13 | Polaroid Corporation | Hydrazine dyes |
US4742160A (en) * | 1983-11-14 | 1988-05-03 | Sandoz Ltd. | Sulfo group-containing basic azo compounds having a central 1,3,5-triazine ring and two terminal 1-hydroxynaphthyl-2 groups and 1:1 and 1:2 metal complexes therof |
EP0312004A2 (en) * | 1987-10-13 | 1989-04-19 | Hoechst Aktiengesellschaft | Use of colouring agents in recording fluids |
US5495003A (en) * | 1993-01-30 | 1996-02-27 | Sandoz Ltd. | 2,2'-disulfo-4,4'-substituted triazinylaminophenyl disazostilbenes |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6712462B2 (en) | 2001-05-14 | 2004-03-30 | Seiko Epson Corporation | Ink set and ink jet recording method |
US6779881B2 (en) | 2001-09-13 | 2004-08-24 | Seiko Epson Corporation | Ink, ink set, and ink jet recording method |
US7476260B2 (en) | 2004-04-08 | 2009-01-13 | Ciba Specialty Chemicals Corp. | Disulfide dyes, composition comprising them and method of dyeing hair |
EP2075036A1 (en) * | 2004-04-08 | 2009-07-01 | Ciba Holding Inc. | Disulfid dyes, composition comprising them and method of dyeing hair |
CN107475724A (en) * | 2017-07-06 | 2017-12-15 | 广东石油化工学院 | Nitrogenous organic phosphorous acids corrosion inhibiter and synthetic method |
Also Published As
Publication number | Publication date |
---|---|
GB2389588A (en) | 2003-12-17 |
GB2389588B (en) | 2005-03-23 |
WO2002070609A8 (en) | 2004-04-08 |
GB0319749D0 (en) | 2003-09-24 |
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