# US 2008/0187665 A1 · Phase change inks containing colorant compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2008/0187665 A1 - Document ID: US20080187665A1 - Status: Published application - Kind: A1 - Application number: 11/702,875 - Filed: 2007-02-06 - Published: 2008-08-07 - Earliest claimed: 2007-02-06 - Assignees: Xerox Corporation - Inventors: Jeffrey H. Banning - Web page: https://patentgrep.com/patent/US20080187665A1 ## CPC - C09B 11/24: Phthaleins containing amino groups {; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes} - C09B 11/02: derived from diarylmethanes - C09B 69/103: {containing a diaryl- or triarylmethane dye} - C09D 11/34: Hot-melt inks - C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P) - 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 (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) ## Abstract Phase change inks comprising a carrier and a colorant of the formula wherein R1, R2, R3, R4, R5, R6, R, Y, CA, A-, m and n each, independently of the others are as defined herein. ## Claims ### Claim 1 A phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula wherein R1, R2, R3, and R4 each, independently of the others, is (i) a hydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) an arylalkyl group, or (v) an alkylaryl group, wherein R1 and R2 can be joined together to form a ring, wherein R3 and R4 can be joined together to form a ring, and wherein R1, R2, R3, and R4 can each be joined to a phenyl ring in the central structure; wherein a and b each, independently of the others, is an integer which is 0, 1, 2, or 3, wherein each R5, and R6 independently of the other, is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylaryl group, (v) a halogen atom, (vi) an ester group, (vii) an amide group, (viii) a sulfone group, (ix) an amine group or ammonium group, (x) a nitrile group, (xi) a nitro group, (xii) a hydroxy group, (xiii) a cyano group, (xiv) a pyridine or pyridinium group, (xv) an ether group, (xvi) an aldehyde group, (xvii) a ketone group, (xviii) a carbonyl group, (xix) a thiocarbonyl group, (xx) a sulfate group, (xxi) a sulfide group, (xxii) a sulfoxide group, (xxiii) a phosphine or phosphonium group, (xxiv) a phosphate group, (xxv) a mercapto group, (xxvi) a nitroso group, (xxvii) an acyl group, (xxviii) an acid anhydride group, (xxix) an azide group, (xxx) an azo group, (xxxi) a cyanato group, (xxxii) an isocyanato group, (xxxiii) a thiocyanato group, (xxxiv) an isothiocyanato group, (xxxv) a urethane group, (xxxvi) a urea group, or (xxxvii) hydrogen, wherein R5 and R6 can each be joined to a phenyl ring in the central structure, wherein R8, R9, and R10 each, independently of the other, is (i) a hydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) an arylalkyl group, or (v) an alkylaryl group; wherein A is an anion; wherein CA is either a hydrogen atom or a cation; wherein R is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylaryl group, (v) an alkoxy group, (vi) an acetate group, or (vii) a co-polymer of maleic anhydride; wherein n is an integer which is about 1 to about 1,000; and wherein m is an integer which is about 1 to about 1,000. ### Claim 2 (depends on 1) A phase change ink composition according to claim 1, wherein the phase change ink carrier comprises a monoamide, a tetra-amide, or a mixture thereof. ### Claim 3 (depends on 1) A phase change ink composition according to claim 1, wherein the phase change ink carrier comprises (a) stearyl stearamide, (b) a dimer acid based tetra-amide that is the reaction product of dimer acid, ethylene diamine, and stearic acid, or (c) mixtures thereof. ### Claim 4 (depends on 1) A phase change ink composition according to claim 1, wherein the phase change ink carrier comprises an isocyanate-derived material, a urethane isocyanate-derived material, a urea isocyanate-derived material, a urethane/urea isocyanate-derived material, or mixtures thereof. ### Claim 5 (depends on 1) A phase change ink composition according to claim 1, wherein the phase change ink carrier comprises a mixture of one or more amides and one or more isocyanate-derived materials. ### Claim 6 (depends on 1) A phase change ink composition according to claim 1, wherein the phase change ink carrier comprises one or more materials selected from paraffins, microcrystalline waxes, polyethylene waxes, ester waxes, amide waxes, fatty acids, fatty alcohols, fatty amides, sulfonamide materials, tall oil rosins, rosin esters, ethylene/vinyl acetate copolymers, ethylene/acrylic acid copolymers, ethylene/vinyl acetate/acrylic acid copolymers, copolymers of acrylic acid with polyamides, ionomers, and mixtures thereof. ### Claim 7 (depends on 1) A phase change ink composition according to claim 1, wherein the phase change ink carrier is present in the ink in an amount of at least about 0.1 percent by weight of the ink and wherein the phase change ink carrier is present in the ink in an amount of no more than about 99 percent by weight of the ink. ### Claim 8 (depends on 1) A phase change ink composition according to claim 1, wherein the ink further contains an antioxidant. ### Claim 9 (depends on 8) A phase change ink composition according to claim 8, wherein the antioxidant is present in the ink in an amount of at least about 0.01 percent by weight of the ink, and wherein the antioxidant is present in the ink in an amount of no more than about 20 percent by weight of the ink. ### Claim 10 (depends on 1) A phase change ink composition according to claim 1, wherein the ink further contains a viscosity modifier. ### Claim 11 (depends on 10) A phase change ink composition according to claim 10, wherein the viscosity modifier is present in the ink in an amount of at least about 0.1 percent by weight of the ink and wherein the viscosity modifier is present in the ink in an amount of no more than about 99 percent by weight of the ink. ### Claim 12 (depends on 1) A phase change ink composition according to claim 1, wherein the colorant is present in the ink in an amount of at least about 0.1 percent by weight of the ink. ### Claim 13 (depends on 1) A phase change ink composition according to claim 1, wherein the colorant is present in the ink in an amount of no more than about 20 percent by weight of the ink. ### Claim 14 (depends on 1) A phase change ink composition according to claim 1, wherein the ink has a melting point of no lower than about 50° C. and wherein the ink has a melting point of no higher than about 160° C. ### Claim 15 (depends on 1) A phase change ink composition according to claim 1, wherein the ink has a melt viscosity at a temperature of about 140° C. of no more than about 30 centipoise. ### Claim 16 (depends on 1) A phase change ink composition according to claim 1, wherein the ink has a melt viscosity at a temperature of about 140° C. of no less than about 1 centipoise. ### Claim 17 (depends on 1) A phase change ink composition according to claim 1, wherein a and b are each zero. ### Claim 18 (depends on 1) A phase change ink composition according to claim 1, wherein ### Claim 19 (depends on 1) A phase change ink composition according to claim 1, wherein A- is an organic dianion of the formula A1-R11-A2 wherein A1 and A2 each, independently of the other, are anions and wherein R11 is (i) an alkylene group, (ii) an arylene group, (iii) an arylalkylene group, or (iv) an alkylarylene group. ### Claim 20 (depends on 1) A phase change ink composition according to claim 1, wherein at least one of R1, R2, R3, and R4 is an alkyl group. ### Claim 21 (depends on 20) A phase change ink composition according to claim 20, wherein the alkyl group is a linear alkyl group. ### Claim 22 (depends on 20) A phase change ink composition according to claim 20, wherein the alkyl group is a branched alkyl group. ### Claim 23 (depends on 20) A phase change ink composition according to claim 20, wherein the alkyl group is a saturated alkyl group. ### Claim 24 (depends on 20) A phase change ink composition according to claim 20, wherein the alkyl group is an unsaturated alkyl group. ### Claim 25 (depends on 20) A phase change ink composition according to claim 20, wherein the alkyl group is a cyclic alkyl group. ### Claim 26 (depends on 20) A phase change ink composition according to claim 20, wherein the alkyl group is a substituted alkyl group. ### Claim 27 (depends on 20) A phase change ink composition according to claim 20, wherein the alkyl group is an unsubstituted alkyl group. ### Claim 28 (depends on 1) A phase change ink composition according to claim 1, wherein at least one of R1, R2, R3, and R4 is an aryl group. ### Claim 29 (depends on 28) A phase change ink composition according to claim 28, wherein the aryl group is a substituted aryl group. ### Claim 30 (depends on 28) A phase change ink composition according to claim 28, wherein the aryl group is an unsubstituted aryl group. ### Claim 31 (depends on 1) A phase change ink composition according to claim 1, wherein R1 and R2 are joined together to form a ring. ### Claim 32 (depends on 1) A phase change ink composition according to claim 1, wherein R1 and R2 are joined together to form a ring and wherein R3 and R4 are joined together to form a ring. ### Claim 33 (depends on 1) A phase change ink composition according to claim 1, wherein at least one of R1, R2, R3, and R4 is joined to a phenyl ring in the central structure. ### Claim 34 (depends on 1) A phase change ink composition according to claim 1, wherein R is an alkyl group. ### Claim 35 (depends on 1) A phase change ink composition according to claim 1, wherein R is an aryl group. ### Claim 36 (depends on 1) A phase change ink composition according to claim 1, wherein R is an alkylaryl group. ### Claim 37 (depends on 1) A phase change ink composition according to claim 1, wherein R is an arylalkyl group. ### Claim 38 (depends on 1) A phase change ink composition according to claim 1, wherein R has from about 1 to about 100 carbon atoms. ### Claim 39 (depends on 1) A phase change ink composition according to claim 1, wherein R has from about 18 to about 33 carbon atoms. ### Claim 40 (depends on 1) A phase change ink composition according to claim 1, wherein R is C6H5. ### Claim 41 (depends on 1) A phase change ink composition according to claim 1, wherein R is CH2CH2. ### Claim 42 (depends on 1) A phase change ink composition according to claim 1, wherein the colorant is of the formula wherein n is about 1 to about 1,000 and wherein m is about 1 to about 1,000. ### Claim 43 (depends on 1) A phase change ink composition according to claim 1, wherein the colorant is of the formula wherein n is about 1 to about 1,000 and wherein m is about 1 to about 1,000. ### Claim 44 (depends on 1) A phase change ink composition according to claim 1, wherein the colorant is of the formula wherein R30 and R31 each, independently of the other, is an alkyl group, an aryl group, an alkylaryl group, or an arylalkyl group; and wherein n is about 1 to about 1,000, m is about 1 to about 1,000, p is about 1 to about 1,000, and s is about 1 to about 1,000. ### Claim 45 (depends on 1) A phase change ink composition according to claim 1, wherein the colorant is of the formula wherein R30 and R31 each, independently of the other, is an alkyl group, an aryl group, an alkylaryl group, or an arylalkyl group; and wherein n is about 1 to about 1,000, m is about 1 to about 1,000, p is about 1 to about 1,000, and s is about 1 to about 1,000. ### Claim 46 (depends on 1) A phase change ink composition according to claim 1, wherein the colorant is of the formula wherein R30 and R31 each, independently of the other, is an alkyl group, an aryl group, an alkylaryl group, or an arylalkyl group; and wherein n is about 1 to about 1,000, m is about 1 to about 1,000, p is about 1 to about 1,000, and s is about 1 to about 1,000. ### Claim 47 A process which comprises (1) incorporating into an ink jet printing apparatus a phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula wherein R1, R2, R3, and R4 each, independently of the others, is (i) a hydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) an arylalkyl group, or (v) an alkylaryl group, wherein R1 and R2 can be joined together to form a ring, wherein R, and R, can be joined together to form a ring, and wherein R1, R2, R3, and R4 can each be joined to a phenyl ring in the central structure; wherein a and b each, independently of the others, is an integer which is 0, 1, 2, or 3, wherein each R5, and R6 independently of the other, is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylaryl group, (v) a halogen atom, (vi) an ester group, (vii) an amide group, (viii) a sulfone group, (ix) an amine group or ammonium group, (x) a nitrile group, (xi) a nitro group, (xii) a hydroxy group, (xiii) a cyano group, (xiv) a pyridine or pyridinium group, (xv) an ether group, (xvi) an aldehyde group, (xvii) a ketone group, (xviii) a carbonyl group, (xix) a thiocarbonyl group, (xx) a sulfate group, (xxi) a sulfide group, (xxii) a sulfoxide group, (xxiii) a phosphine or phosphonium group, (xxiv) a phosphate group, (xxv) a mercapto group, (xxvi) a nitroso group, (xxvii) an acyl group, (xxviii) an acid anhydride group, (xxix) an azide group, (xxx) an azo group, (xxxi) a cyanato group, (xxxii) an isocyanato group, (xxxiii) a thiocyanato group, (xxxiv) an isothiocyanato group, (xxxv) a urethane group, (xxxvi) a urea group, or (xxxvii) hydrogen, wherein R5 and R6 can each be joined to a phenyl ring in the central structure, wherein R8, R9, and R10 each, independently of the other, is (i) a hydrogen atom, (ii) an alkyl group, (iii) an aryl group, (iv) an arylalkyl group, or (v) an alkylaryl group; wherein A is an anion; wherein CA is either a hydrogen atom or a cation; wherein R is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylaryl group, (v) an alkoxy group, (vi) an acetate group, or (vii) a co-polymer of maleic anhydride; wherein n is an integer which is about 1 to about 1,000; and wherein m is an integer which is about 1 to about 1,000; (2) melting the ink; and (3) causing droplets of the melted ink to be ejected in an imagewise pattern onto a substrate. ### Claim 48 (depends on 47) A process according to claim 47, wherein the printing apparatus employs a piezoelectric printing process wherein droplets of the ink are caused to be ejected in imagewise pattern by oscillations of piezoelectric vibrating elements. ### Claim 49 (depends on 47) A process according to claim 47, wherein the substrate is a final recording sheet and droplets of the melted ink are ejected in an imagewise pattern directly onto the final recording sheet. ### Claim 50 (depends on 47) A process according to claim 47, wherein the substrate is an intermediate transfer member and droplets of the melted ink are ejected in an imagewise pattern onto the intermediate transfer member followed by transfer of the imagewise pattern from the intermediate transfer member to a final recording sheet. ### Claim 51 (depends on 50) A process according to claim 50, wherein the intermediate transfer member is heated to a temperature above that of the final recording sheet and below that of the melted ink in the printing apparatus.