EP2024452A2 - Pigment autodispersant au carbonyle et jet d'encre le comprenant - Google Patents

Pigment autodispersant au carbonyle et jet d'encre le comprenant

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Publication number
EP2024452A2
EP2024452A2 EP07795784A EP07795784A EP2024452A2 EP 2024452 A2 EP2024452 A2 EP 2024452A2 EP 07795784 A EP07795784 A EP 07795784A EP 07795784 A EP07795784 A EP 07795784A EP 2024452 A2 EP2024452 A2 EP 2024452A2
Authority
EP
European Patent Office
Prior art keywords
pigment
group
groups
covalently bound
pigment particles
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.)
Withdrawn
Application number
EP07795784A
Other languages
German (de)
English (en)
Inventor
Richard Douglas Bauer
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP2024452A2 publication Critical patent/EP2024452A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/42—Ionic groups, e.g. free acid
    • C09B68/425—Anionic groups
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing 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
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
    • 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
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
    • C09B68/446—Amines or polyamines, e.g. aminopropyl, 1,3,4,-triamino-pentyl or polyethylene imine
    • 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
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/46—Aromatic cyclic groups
    • C09B68/467—Heteroaromatic groups
    • C09B68/4673—5-Membered rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/44—Carbon
    • C09C1/48—Carbon black
    • C09C1/56—Treatment of carbon black ; Purification
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/10—Treatment with macromolecular organic compounds
    • 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
    • C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
    • C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant

Definitions

  • the present invention relates generally to self-dispersing pigments and to use thereof in inkjet ink. More particularly, it is directed to a self-dispersing pigment having covalently bound stabilizing groups that enable formation of a stable dispersion of the pigment in a liquid and in addition, at least one covalently bound external reactive carbonyl group.
  • This pigment is particularly useful in reactive inkjet ink formulations.
  • InkJet printing is a non-impact printing process in which droplets of ink are deposited on various media to form the desired image. The droplets are ejected from a printhead in response to electrical signals generated by a microprocessor. Inks used are subject to rigorous demands including, for example, good dispersion stability, ejection stability, and good fixation to media.
  • InkJet printers offer low cost, high quality printing and have become a popular alternative to other types of printers such as laser printers. However, inkjet printers have been unable to match the speed of laser printers and the durability of the laser printed images. InkJet prints with increased durability would be highly advantageous.
  • Using a reactive inkjet ink set comprising at least two inks can increase the durability of inkjet prints.
  • the first ink contains species having at least one reactive carbonyl group; and the second ink contains species having at least one reactive amine group.
  • the present invention pertains to a self-dispersing pigment comprising pigment particles having (a) covalently bound stabilizing groups that enable formation of a stable dispersion of the pigment in a liquid and (b) covalently bound species containing at least one external reactive carbonyl group.
  • This invention further provides an inkjet ink comprising a liquid vehicle and pigment comprising pigment particles having covalently bound stabilizing groups that enable formation of a stable dispersion of the pigment in a liquid and covalently bound species containing at least one external reactive carbonyl group.
  • This invention also provides an inkjet ink set comprising at least a first ink and a second ink wherein, a) the first ink comprises a liquid vehicle and pigment comprising pigment particles having covalently bound stabilizing groups that enable formation of a stable dispersion of the pigment in a liquid and covalently bound species containing at least one external reactive carbonyl group; and b) the second ink comprises a liquid vehicle and species having at least one reactive amine group.
  • FIG. 1 shows, in schematic, examples of seven synthetic routes that can be used to produce carbonyl group containing self-dispersing carbon black or organic pigment particles, useful in the practice of this invention (with the resulting pigment particles being designated as particles 11-17, respectively).
  • FIG. 2 shows the preparation of the diazotized precursor used in the reaction producing carbonyl self-dispersing pigment particle 11 of FIG.1.
  • FIG. 3 shows the preparation of the diazotized precursor used in the reaction producing carbonyl self-dispersing pigment particle 12 of FIG. 1 and alternative alkylation reagents to prepare analogs of carbonyl self-dispersing pigment particle 12.
  • FIG. 4 shows the preparation of the amine precursor used in the reaction producing carbonyl self-dispersing pigment particle 13 of FIG. 1.
  • FIG. 5 shows the preparation of the beta-keto amide precursors used in the s producing carbonyl self-dispersing pigment particles 15 and 16 of FIG. 1.
  • FIG. 6 shows the preparation of the diketone precursor used in the reaction producing carbonyl self-dispersing pigment particle 17 of FIG. 1.
  • FIG. 7 illustrates three additional synthetic routes that can be used to form carbonyl self-dispersing carbon black or organic pigment particles, useful in the practice of this invention.
  • FIG. 8 shows examples of three other reactions that produce carbonyl self- dispersing carbon black or organic pigment particles, useful in the practice of this invention.
  • FIG. 9 shows examples of two further reactions that can be used to produce carbonyl self-dispersing carbon black or organic pigment particles useful in the practice of this invention by attaching carbonyl groups to the D groups.
  • FIG. 10 shows an example of another synthetic route to carbonyl self- dispersing carbon black or organic pigments, useful in the practice of this invention.
  • FIGS. 11-12 show examples of a synthetic route to produce carbonyl self- dispersing inorganic pigments, useful in the practice of this invention.
  • This invention provides a carbonyl self-dispersing pigment, i.e., a pigment with pigment particles containing covalently bound stabilizing groups that enable formation of a stable dispersion of the pigment in a liquid and covalently bound species containing at least one external reactive carbonyl group.
  • a pigment particle contains a sufficient number of covalently bound stabilizing groups to enable the particles to form a stable dispersion in a liquid and contains at least one covalently bound external reactive carbonyl group.
  • the pigment particle contains two or more external reactive carbonyl groups.
  • the carbonyl self-dispersing pigment is particularly useful in an inkjet set ink when another ink in the ink set contains species having reactive amine groups.
  • self-dispersing means a pigment having stabilizing groups covalently attached to the surface of the pigment particles such that the pigment particles form a stable dispersion in a liquid in the absence of any other dispersion agents.
  • the covalently bound stabilizing groups that enable the formation of a stable dispersion of the pigment in a liquid are designated herein as "D” groups, i.e., dispersing groups.
  • novel self-dispersing pigments are also provided with reactive carbonyl group(s), so that they can participate in desired crosslinking reactions.
  • reactive carbonyl groups that are effective at crosslinking are not effective at dispersing and therefore the covalently bound dispersing group(s) and covalently bound reactive carbonyl group(s) on the instant self-dispersing pigment are typically separate and distinct species.
  • Self-dispersing pigments with covalently bound dispersing groups are well known in the art, but self-dispersing pigments with both covalently bound dispersing groups and reactive carbonyl groups are novel and unique.
  • the carbonyl groups are "external” groups in the sense that a) they are not part of the pigment molecular formula but are attached substantially only to the pigment molecules at the surface of a pigment particle, and b) they are terminal groups at the outer end, i.e., the end not covalently bound to the pigment particle, of the entity that is covalently bound to the pigment particle.
  • the carbonyl groups are described as "reactive” because they are capable of reacting with, i.e., crosslinking with, reactive amine groups. The reactivity of these carbonyl groups is increased as a result of their position at the outer end of the entity that is covalently bound to the pigment particle.
  • Various alkyl or aryl groups or hydrogen can be attached to the carbonyl group to form ketones or aldehydes. Reactivity of the carbonyl group is expected to be highest when a methyl group or hydrogen is attached to the carbonyl group.
  • the species containing the external reactive carbonyl groups can be covalently bound to the pigment particle or can be part of the covalently bound stabilizing groups. The species containing the external reactive carbonyl groups can be covalently bound directly to the pigment particle, attached to other groups that are covalently bound to the pigment particle, or appended to a polymer chain that is covalently bound to the pigment particle.
  • the pigment particles can be carbon black particles, organic colored pigment particles, or inorganic pigment particles.
  • Representative commercial pigments in dry form include the following:
  • Representative commercial pigments available in the form of a water-wet presscake include: Heucophthal® Blue BT-585-P, Toluidine Red Y (C.I. Pigment Red 3), Quindo® Magenta (Pigment Red 122), Magenta RV-6831 presscake (Mobay Chemical, Harmon Division, Haledon, NJ.), Sunfast.RTM. Magenta 122 (Sun Chemical Corp., Cincinnati, OH), Indo® Brilliant Scarlet (Pigment Red 123, C.I. No. 71145), Toluidine Red B (CI. Pigment Red 3), Watchung® Red B (C.I.
  • Pigment Red 48 Permanent Rubine F6B13-1731 (Pigment Red 184), Hansa® Yellow (Pigment Yellow 98), Dalamar® Yellow YT-839-P (Pigment Yellow 74, C.I. No. 11741, Sunbrite.® Yellow 17 (Sun Chemical Corp, Cincinnati, Ohio), Toluidine Yellow G (CI. Pigment Yellow 1), Pigment Scarlet (Cl Pigment Red 60), Auric Brown (CI. Pigment Brown 6), etc. Black pigments, such as carbon black, generally are not available in the form of aqueous presscakes.
  • the liquid vehicle carrier of inkjet ink can be aqueous or organic.
  • aqueous liquid or "aqueous vehicle” refers to water or a mixture of water and at least one water-soluble organic solvent (co-solvent). Selection of a suitable mixture depends on requirements of the specific application, such as desired surface tension and viscosity, the selected colorant, drying time of the ink, and the type of substrate onto which the ink will be printed. If a mixture of water and a water-soluble solvent is used, the aqueous vehicle typically will contain about 30% to about 95% water with the balance (i.e., about 70% to about 5%) being the water-soluble solvent. Preferred compositions contain about 60% to about 95% water, based on the total weight of the aqueous vehicle.
  • Organic liquid or “organic vehicle” refers to a liquid or vehicle that is substantially nonaqueous and is comprised of organic solvent or mixtures of such solvents.
  • solvents can be polar and/or nonpolar.
  • polar solvents include alcohols, esters, ketones and ethers, particularly mono- and di- alkyl ethers of glycols and polyglycols such as monomethyl ethers of mono-, di- and tri-propylene glycols and the mono-n-butyl ethers of ethylene, diethylene and triethylene glycols.
  • nonpolar solvents include aliphatic and aromatic hydrocarbons having at least six carton atoms and mixtures thereof including refinery distillation products and by-products.
  • an organic vehicle will have no more than about 10%, and preferably no more than about 5%, by weight of water based on the total weight of the nonaqueous vehicle.
  • the covalently bound stabilizing groups for aqueous liquids can be carboxylate, amine, sulfonate, sulfinate, phosphate, amine, quatemized amine, or ethoxylate oligomer groups, or covalently bound polymers containing these stabilizing groups.
  • These covalently bound groups need to be present in sufficient quantity to allow the pigment particles to form a stabile dispersion as prepared or by neutralizing acidic groups with base to form anions or neutralizing basic groups with acid to form cations.
  • Inorganic oxide particles can be stabilized to form dispersions by adsorbed cations or anions or by covalently bound anionic or cationic groups for aqueous liquids or they can be stabilized to be dispersible in organic liquid.
  • covalently bound stabilizing groups includes these adsorbed cations or anions as well as the covalently bound anionic or cationic groups.
  • stabilizing groups compatible with organic liquids are used.
  • the stabilizing groups in organic liquid can also be organic solvent compatible salts of bonded acid or basic groups.
  • Self-dispersing carbon black particle dispersions stabilized by carboxylate groups created by oxidation of the surface of those particles are disclosed in a number of patents.
  • Self-dispersing carbon black prepared by ozonation and grinding of carbon black in a media mill is disclosed in US 6,852,156.
  • Processes to prepare a carbon black dispersion by treatment of carbon black with ultrasonic energy and hydrogen peroxide or with heat and a monopersulfate are disclosed in US 6,723,161 and US 2004/0103822.
  • a series of patents, US 5,718,746, US 5,846,307, US 5,861,447, US 6,468,342 and US 6,480,753 disclose the preparation of stable dispersions using hypohalite reagents to oxidize carbon black.
  • US 6,831,194 discloses the surface modification of carbon particles by reacting them with cyclic anhydrides and AlCl 3 catalyst and the formation of a stable aqueous dispersion.
  • US 6,660,075 discloses the surface modification of carbon particles with reagents containing double and triple bonds activated by carbonyl groups, e.g., maleic anhydride.
  • carbonyl groups e.g., maleic anhydride.
  • a variety of groups that can stabilize the particles in aqueous environments (anionic and cationic groups) or organic environments can be covalently bound to the particles using this chemistry.
  • US 6,758,891 discloses the reaction of carbon particles with organic compounds of the general formula to functionalize them with carboxylates, sulfonates, amines, or quaternary groups for dispersion stability in aqueous environments or organic groups which will stabilize a dispersion of the particles in an organic environment.
  • US2001/0036994 describes carbon black particles modified with organic groups which are bound via a sulfide or polysulfide linkage by reacting those particles with compounds of the general formula R 1 -S x -R 2 .
  • US 5,922,118, US 5,900,029, US 5,851,280, US 5,895,522, US 5,885,335, US 5,851 ,280; and US 5,837,045 disclose methods for attaching organic stabilizing groups to carbon black via a diazonium reaction wherein the organic stabilizing group is part of the diazonium salt.
  • the stabilizing groups include carboxylates, sulfonates, amines, and quaternary amines that would stabilize a dispersion of the particles in an aqueous medium and organic groups that would stabilize the particles in an organic medium.
  • US 6,398,858, US 6,494,943 and
  • US 6,506,245 describe similar methods for attaching stabilizing groups to colored organic pigments.
  • US 5,713,988, US 6,336,965, and US 6,432,194 describe carbon blacks functionalized with diazonium salts containing non-ionic stabilizing groups (and optionally ionic groups) for stabilizing the pigments in organic or aqueous vehicles.
  • Carbon black particles can be modified by the addition of radicals containing groups that will stabilize a dispersion of the particles in aqueous or organic vehicles. Such dispersions can be suitable for inkjet.
  • An example of a preferred radical forming reagent with hydrophilic groups is 4,4'-Azobis(4- cyanopentanecarboxylic acid).
  • Azo radical forming compounds that would impart aqueous dispersability would include:
  • JP 11323222A discloses carbon particles functionalized with hydroperoxide compounds of the general formula A 1 -O-O-H, where Ai is a substituted linear, branched, or cyclic hydrocarbons group that can contain hydrophilic or hydrophobic groups.
  • JP 11335586A describes carbon particles functionalized with peroxyester compounds of the general formula where Ai and A 2 are the same or different substituted linear, branched, or cyclic hydrocarbons groups that can contain hydrophilic or hydrophobic groups.
  • JP 11335587A describes carbon particles functionalized with peroxyester compounds of the general formula A]-O-O-A 2 , where Ai and A 2 are different substituted linear, branched, or cyclic hydrocarbons groups that can contain hydrophilic or hydrophobic groups.
  • the preparation starts with a pigment modified for water dispersibility to which is attached groups with vinyl unsaturation.
  • a wide range of monomers is disclosed for grafting to these unsaturated sites to form polymer chains.
  • Carbonyl self-dispersing organic and carbon black pigments can be prepared in a variety of ways. Species containing at least one external reactive carbonyl group can be covalently bonded to self-dispersing pigment particles suitable for inkjet ink use. The addition of the stabilizing groups prior to covalently bonding the species containing at least one external reactive carbonyl group can be advantageous in that the proper pigment particle size can be achieved and assured before the addition of the carbonyl groups.
  • the stabilizing groups and the species containing at least one external reactive carbonyl group can be covalently bonded to the pigment particles in a single process.
  • the species containing at least one external reactive carbonyl group can be a ketone, beta diketone, beta keto ester group, their imine and enamine forms and their aldehyde analogs.
  • the imine and enamine forms can be in equilibrium with the carbonyl when amines are present in solution with the carbonyl.
  • R is a Ci to Ci o alkyl group or an aryl group for the imine and R is H for the aldehyde analog and wherein R 1 is a Ci to C 10 alkyl group or an aryl group.
  • -C C(NR l R 2 )R wherein R is a Ci to C ]0 alkyl group or an aryl group for the enamine and R is H for the aldehyde analog and wherein R 1 and R 2 are the same or different Ci to Cio alkyl groups or an aryl groups.
  • X is CH 2 for the beta diketone and X is O or NH for the beta keto ester, wherein R 1 is a Ci to Cio alkyl group or an aryl group and wherein R is a Cj to Cio alkyl group or an aryl group for the ketones and R is H for the aldehyde analogs.
  • R 1 and R 2 are the same or different Ci to Cio alkyl groups or an aryl groups and wherein R is a Ci to Cio alkyl group or an aryl group for the enamine form analogs of the above diketone and ester and R is H for the aldehyde analogs.
  • the species containing at least one external reactive carbonyl group also includes ketone and aldehyde groups activated by an electron withdrawing group (EWD).
  • the EWD can be a CN group, a SO group, a SO 2 group, a SO 3 group, a SO 2 NH group, a PO group, a PO 3 group, or a PO 2 NH group.
  • the point of attachment of these species to the pigment particle or to an entity covalently bonded to the pigment particle species can be either through the alpha carbon between the reactive carbonyl and the EWD or through the EWD, valency permitting.
  • the various species are depicted as follows:
  • EWD is a CN, SO, SO 2 , SO 3 , SO 2 NH, PO, PO 3 OrPO 2 NH group, wherein R 1 is a Ci to Cio alkyl group or an aryl group and wherein R is a Ci to Cio alkyl group or an aryl group for the activated ketone and R is H for the activated aldehyde.
  • the species can also be a ketal, acetal, cyclic ketal, or cyclic acetal group.
  • the ketals and acetals are stable in neutral or slightly alkaline solution but revert to the reactive ketone or aldehyde in the presence of acid.
  • the various species are depicted as follows:
  • R 1 is a Ci to Cio alkyl group or an aryl group and wherein R is a Ci to Cio alkyl group or an aryl group for the ketal and R is H for the acetal.
  • R is a Ci to Qo alkyl group or an aryl group for the cyclic ketal and R is H for the cyclic acetal.
  • R be a methyl group or H.
  • the species containing at least One external reactive carbonyl group is selected from the group consisting of ketone, aldehyde, beta diketone, beta keto ester, imine and enamine forms of ketone, aldehyde, beta diketone, and beta keto ester, ketal, acetal, cyclic ketal, cyclic acetal, ketone activated with an electron withdrawing group, aldehyde activated with an electron withdrawing group, and combinations thereof.
  • ketone or aldehyde groups include all of these groups.
  • FIG. 1 illustrated in FIG. 1 are seven examples of reactions of a carbon black pigment or organic pigment particle, identified by reference numeral 10, with diazotized reagents that produce the desired carbonyl self-dispersing carbon black pigment or organic pigment particles, which are identified by reference numerals 11-17.
  • the carbon black or organic pigment particle 10 as shown has been surface functionalized to contain D groups to enable the formation of stable dispersions in an aqueous vehicle.
  • the dispersing D groups can be introduced by any of the methods described above that would be appropriate for a given pigment.
  • the covalent attachment of reactive ketone or aldehyde groups to the pigment particle surface is carried out with the diazotized reagents.
  • the diazotized precursor used in the reaction producing carbonyl self- dispersing pigment particle 11 would be prepared as shown in FIG. 2 using para- aminoacetophenone, a commercially available compound which can be diazotized with sodium nitrite in aqueous HCl. The diazotized precursor is then reacted with dispersed pigment particles as shown in FIG. 1 to provide the desired carbonyl self-dispersing pigment particles.
  • the amino ketones used to prepare the diazotized precursors used in the reaction producing carbonyl self-dispersing pigment particles 12 or 14 can be made using a synthetic strategy analogous with that described by Ho well and Liu, Thermochimica Acta, 243, (1994), 169-192 as shown in FIG. 3 for pigment particle 12.
  • the chloro group on p-chloro nitrobenzene is displaced with the methylacetoacetate anion, followed by reduction of the nitro group and hydrolysis and decarboxylation to yield the amine which can be diazotized with sodium nitrite in aqueous HCl.
  • the diazotized precursor is then reacted with dispersed pigment particles as shown in FIG.
  • the amine precursor used in the reaction producing carbonyl self-dispersing pigment particle 13 can be prepared by a synthetic route analogous to one described by Wang, et. al., Dyes and Pigments, 41 (1999), 35-39 as shown in FIG. 4.
  • the sodium salt of the commercially available sulfinic acid can be reacted with chloro acetone, followed by cleavage of the acetyl group form the amine and then diazotization.
  • the amine precursor is then reacted with dispersed pigment particles as shown in FIG. 1 to provide the desired carbonyl self-dispersing pigment particles.
  • the beta-keto amide precursors used in the reactions producing carbonyl self-dispersing pigment particles 15 and 16 can be prepared by reacting p- nitrobenzyl amine in the case of 15 or p-nitroaniline in the case of 16 with diketene or with 2,2,6-trimethyl-4H-l,3-dioxin-4-one as shown in FIG. 5. The nitro groups are then reduced to amines as shown and each is diazotized with sodium nitrite in aqueous HCl. The beta-keto amide precursors are reacted with dispersed pigment particles as shown in FIG. 1 to provide the desired carbonyl self-dispersed pigment particles with reactive beta-ketone groups.
  • the diketone precursor used in the reaction producing carbonyl self- dispersing pigment particle 17 can be prepared as shown in FIG. 6 by starting with the sulfate ester of a blocked vinyl sulfone that is reacted with acetyl acetone anion. This is followed by cleaving the acetyl group protecting the amine. The resulting amine can be diazotized with sodium nitrite in aqueous HCl. The diketone precursor is then reacted with dispersed pigment particles to provide the desired carbonyl self-dispersing pigment particles with reactive beta-diketone groups.
  • FIG. 7 Three examples of another route for producing self-dispersing carbon black or organic pigment particles with reactive carbonyl groups are illustrated in FIG. 7.
  • the carbon black pigment or organic pigment particle 20 has been surface functional ized to contain D groups to enable the formation of stable dispersions in an aqueous vehicle.
  • the dispersing D groups can be introduced by any of the methods described above that would be appropriate for a given pigment.
  • Reagents containing carbonyl groups and activated double bonds would be reacted with the pigment particle 20 to produce carbonyl self-dispersing pigment particles 21, 22 and 23.
  • the ketone precursor to particle 22 can be prepared by reaction between diketene and phthalimide.
  • the ketone reagent precursors for particles 22 and 23 are commercially available.
  • FIG. S Three examples of still another route for producing self-dispersing carbon black or organic pigment particles with reactive carbonyl groups are illustrated in FIG. S.
  • the carbon black or organic pigment particle 30 has been surface functionalized to contain D groups. Reagents that are capable of fragmenting into radicals and contain reactive carbonyl groups would be reacted with the pigment particle 30 to produce carbonyl self-dispersing pigment particles 31, 32 and 33.
  • the preparation of the azo ketone precursors for 31, 32, and 33 is described in Tetrahedron, VoI 36, 1753 (1980) and Tetrahedron Letters, VoI 28, pp4255-4258, 1987.
  • Carbonyl self-dispersing pigments can be prepared by the appropriate reactions on the stabilizing groups or other groups that have already been attached to the pigment surface.
  • DTMM (4,6-dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholiniurn chloride
  • the reaction to form the activated ester can be done in the presence of the amine.
  • This chemistry would be well suited for appending reagents containing ketones or aldehydes with amine groups to the D groups of carboxylated pigments directly in the aqueous phase as illustrated in FIG. 9.
  • the carboxylated dispersed pigment particle 40 is reacted with DMTMM to form the activated ester 41.
  • a reagent containing aldehyde or ketone is then reacted with the activated ester to produce carbonyl self-dispersing pigment particles 42 and 43.
  • US 6,723,783 discloses carbon particles that have been reacted with diazotized 2-(4-aminophenylsulfonyl) ethyl hydrogen sulfate to yield self- dispersing carbon black pigment or organic pigment particles that can be further reacted with amine containing reagents while in the aqueous phase. These pigment particles are reacted with polyamine species to prepare polymer modified particles. For the purposes of the instant invention, these pigment particles can be reacted with amine or other nucleophilic reagents containing carbonyls to form carbonyl self-dispersing carbon black pigments or organic pigments. As illustrated in FIG. 10, the carbon black pigment or organic pigment particle 50 can have separate dispersing groups, e.
  • the reaction with diazotized 2-(4-aminophenylsulfonyl) ethyl hydrogen sulfate yields the self-dispersing pigment particle 51.
  • the precursor nucleophiles are commercially available materials.
  • Their reaction with pigment particle 51 yields carbonyl self-dispersing carbon black pigment or organic pigment particle 52, 53, and 54.
  • Carbonyl self-dispersing inorganic pigments are another embodiment of the instant invention.
  • Oxide pigments are preferred, e.g., TiO2 or iron oxide.
  • the pigments may also bear one or more metal oxide surface coatings.
  • metal oxide coatings include silica, alumina, alumina-silica and zirconia.
  • the surfaces of these oxide particles contain hydroxyl groups that allow them to be functionalized with siloxane reagents containing reactive ketone groups.
  • Examples of five reactions of different siloxane reagents with an oxide pigment particle that produce carbonyl self-dispersing oxide pigment are illustrated in FIG. 11.
  • the oxide particle 60 is reacted with the respective siloxane to produce carbonyl self-dispersing oxide pigments 61-65.
  • FIG. 12 illustrates synthetic routes to the five siloxane reagents used in the reactions shown in FIG. 11.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Ink Jet (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)

Abstract

La présente invention concerne des pigments possédant des groupes stabilisateurs liés par covalence qui permettent la formation d'une dispersion stable du pigment dans un liquide ainsi que des espèces liées par covalence qui comprennent au moins un groupe carbonyle réactif externe. De tels pigments sont particulièrement utiles dans des formulations d'encre réactives pour jet d'encre.
EP07795784A 2006-06-05 2007-06-05 Pigment autodispersant au carbonyle et jet d'encre le comprenant Withdrawn EP2024452A2 (fr)

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JP5586876B2 (ja) * 2009-05-29 2014-09-10 キヤノン株式会社 インクセット、インクジェット記録方法
JP6860330B2 (ja) * 2015-12-28 2021-04-14 キヤノン株式会社 自己分散顔料の製造方法、インクの製造方法、及びインクジェット記録方法

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JP3612704B2 (ja) * 2000-04-18 2005-01-19 セイコーエプソン株式会社 インクジェット記録用インクセット、その記録方法及び記録装置並びに記録物
US6585815B2 (en) * 2000-06-21 2003-07-01 Canon Kabushiki Kaisha Ink set, ink-jet printing method using such ink set, recording unit, ink cartridge and ink-jet printing apparatus
US6540344B2 (en) * 2000-06-21 2003-04-01 Canon Kabushiki Kaisha Ink-jet ink, ink set, method for ink-jet printing, ink-jet printing apparatus, ink-jet printing unit and ink cartridge
US6547381B2 (en) * 2000-06-23 2003-04-15 Canon Kabushiki Kaisha Ink, image recording process, ink cartridge, recording unit, ink set, crust-preventing method and image forming apparatus
US6979365B2 (en) * 2003-03-06 2005-12-27 Kao Corporation Ink set
JP4517591B2 (ja) * 2003-06-05 2010-08-04 富士ゼロックス株式会社 インクジェット用インクセット、及びインクジェット記録方法
US7638561B2 (en) * 2004-06-22 2009-12-29 Rohm And Haas Company Aqueous inkjet ink composition
US20060139426A1 (en) * 2004-12-28 2006-06-29 Fuji Xerox Co., Ltd. Ink, ink set, processing solution, recording method, recording medium, ink tank, and recording device
JP4803356B2 (ja) * 2005-08-15 2011-10-26 セイコーエプソン株式会社 インクセット及びこれを用いた記録方法、記録物
US7655708B2 (en) * 2005-08-18 2010-02-02 Eastman Kodak Company Polymeric black pigment dispersions and ink jet ink compositions
US7550039B2 (en) * 2005-12-08 2009-06-23 Eastman Kodak Company Aqueous inkjet ink composition

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