# US 10,767,064 B2 · Ink jet inks having IR-absorbing dye > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,767,064 B2 - Document ID: US10767064B2 - Status: Granted - Kind: B2 - Application number: 16/343,804 - Filed: 2017-10-12 - Published: 2019-08-29 - Granted: 2020-09-08 - Earliest claimed: 2016-10-28 - Assignees: Agfa NV - Applicants: Agfa NV - Inventors: Johan Loccufier; Ellen Bertels - Web page: https://patentgrep.com/patent/US10767064B2 ## CPC - C09D 11/328: characterised by dyes - B41J 2/01: Ink jet - B41M 5/0023: {Digital printing methods characterised by the inks used (inks per se C09D11/00)} - C09B 23/086: {more than five >CH- groups} - C09B 67/0033: {Blends of pigments; Mixtured crystals; Solid solutions} - C09D 11/033: characterised by the solvent - C09D 11/037: characterised by the pigment - C09D 11/102: containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds - C09D 11/322: Pigment inks - B41J 11/00216: {using infrared [IR] radiation or microwaves} - 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) - B41J: TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS - B41M: PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING, (correction of typographical errors B41J; processes for applying transfer pictures or the like B44C1/16; fluid media for correction of typographical errors by coating C09D10/00; printing textiles D06P) - 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) ## Abstract An ink jet ink includes water, a water-soluble organic solvent, a resin, and an anionic heptamethine cyanine dye including a substituted or unsubstituted five or six membered ring in the heptamethine chain, the dye having a maximum absorption between 800 and 1200 nm to increase drying speed and improve image quality when dried with NIR or CIR dryers. ## Claims ### Claim 1 An ink jet ink comprising: water; a water-soluble organic solvent; a resin; and an anionic heptamethine cyanine dye including a substituted or unsubstituted five or six membered ring in a chain of the anionic heptamethine cyanine dye, the anionic heptamethine cyanine dye having a maximum absorption between 800 nm and 1200 nm and including a structural moiety according to formula I or formula II: wherein L1 and L2 independently represent a substituted or unsubstituted alkylene group; R1 is selected from the group consisting of a hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkaryl group, a substituted or unsubstituted aryl or heteroaryl group, a halogen, a hydroxyl, an alkoxy group, a thioether, a sulfoxide, a sulfone, a sulfonic acid or salt thereof, a carboxylic acid or salt thereof, an ester, an amide, and an amine; M represents a hydrogen or a counterion that compensates for a negative charge of the sulfonate group MO3S; R2 and R3 are independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkaryl group, and a substituted or unsubstituted aryl or heteroaryl group, and R2 and R3 may represent atoms necessary to form a substituted or unsubstituted five to eight membered ring; and R4 and R5 are independently selected from the group consisting of a hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkaryl group, a substituted or aryl or heteroaryl group, a halogen, a hydroxyl, an alkoxy group, a thioether, a sulfoxide, a sulfone, a sulfonic acid or salt thereof, a carboxylic acid or salt thereof, an ester, an amide, and an amine, and R4 and R5 may represent atoms necessary to form a substituted or unsubstituted five to eight membered ring. ### Claim 2 (depends on 1) The ink jet ink according to claim 1, wherein the anionic heptamethine cyanine dye includes a compound according to formula III: wherein R6 and R7 represent atoms necessary to form a five or six membered ring; R8 is selected from the group consisting of a hydrogen, a halogen, a thioether, and an alkoxy group; L3 represents a substituted or unsubstituted alkylene group; X is selected from the group consisting of a halogen, an amide, a carbamate, a sulphonamide, an alkoxy group, a thioether, and a sulfone; and Me is a methyl group. ### Claim 3 (depends on 2) The ink jet ink according to claim 2, wherein R6 and R7 represent an unsubstituted carbocyclic five or six membered ring, and X represents a halogen. ### Claim 4 (depends on 2) The ink jet ink according to claim 2, further comprising a colorant. ### Claim 5 (depends on 4) The ink jet ink according to claim 4, wherein the colorant is a pigment. ### Claim 6 (depends on 1) The ink jet ink according to claim 1, wherein the anionic heptamethine cyanine dye includes a compound having the formula IV: wherein R9 and R10 represent atoms necessary to form a five or six membered ring; R11 and R12 are independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkaryl group, and a substituted or unsubstituted aryl or heteroaryl group; R13 is selected from the group consisting of a hydrogen, a halogen, and an alkoxygroup; and L4 represents a substituted or unsubstituted alkylene group. ### Claim 7 (depends on 6) The ink jet ink according to claim 6, wherein R9 and R10 represent an unsubstituted carbocyclic five or six membered ring, and R13 represents hydrogen. ### Claim 8 (depends on 6) The ink jet ink according to claim 6, further comprising a colorant. ### Claim 9 (depends on 8) The ink jet ink according to claim 8, wherein the colorant is a pigment. ### Claim 10 (depends on 8) The ink jet ink according to claim 8, wherein the resin includes a polyurethane resin. ### Claim 11 (depends on 10) The ink jet ink according to claim 10, wherein the polyurethane resin is obtained by reacting a polyester polyol, a polyether diol, a polyol including an anionic group, and a polyisocyanate; and the polyester polyol is obtained by reacting an aromatic polycarboxylic acid and a polyol. ### Claim 12 (depends on 1) The ink jet ink according to claim 1, further comprising a colorant. ### Claim 13 (depends on 12) The ink jet ink according to claim 12, wherein the colorant is a pigment. ### Claim 14 (depends on 1) The ink jet ink according to claim 1, wherein the resin includes a polyurethane resin. ### Claim 15 (depends on 14) The ink jet ink according to claim 14, wherein the polyurethane resin is obtained by reacting a polyester polyol, a polyether diol, a polyol including an anionic group, and a polyisocyanate; and the polyester polyol is obtained by reacting an aromatic polycarboxylic acid and a polyol. ### Claim 16 (depends on 12) The ink jet ink according to claim 12, wherein the resin includes a polyurethane resin. ### Claim 17 (depends on 1) A method of ink jet recording comprising: providing a substrate; jetting on the substrate the ink jet ink according to claim 1; and heating the ink jetted on the substrate with a Near Infra Red heater or a Carbon Infra Red heater. ### Claim 18 (depends on 17) The method according to claim 17, wherein the ink jet ink includes a colorant. ### Claim 19 (depends on 17) The method according to claim 17, wherein the resin includes a polyurethane resin. ### Claim 20 (depends on 19) The method according to claim 19, wherein the polyurethane resin is obtained by reacting a polyester polyol, a polyether diol, a polyol including an anionic group, and a polyisocyanate; and the polyester polyol is obtained by reacting an aromatic polycarboxylic acid and a polyol.