DISPERSION, INK JET RECORDING METHOD, RECORDED MATERIAL, AND COMPOUND

Abstract

Provided are a dispersion, applications thereof, and a compound, the dispersion including: a colorant represented by the following Formula 1; and a medium. In Formula 1, L.sup.1 represents a methine chain consisting of 5 or 7 methine groups, a methine group at a center of the methine chain has a substituent represented by the following Formula A, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, and X's each independently represent an oxygen atom, a sulfur atom, or a selenium atom. In Formula A, SA represents a single bond, an alkylene group, an alkenylene group, or an alkynylene group, T.sup.A represents a hydrogen atom, a halogen atom, an alkyl group, or an aryl group, and * represents a binding site to the methine group at the center of the methine chain.

Claims

1. A dispersion comprising: a colorant represented by the following Formula 1; and a medium, ##STR00036## in Formula 1, L.sup.1 represents a methine chain consisting of 5 or 7 methine groups, a methine group at a center of the methine chain has a substituent represented by the following Formula A, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, and X's each independently represent an oxygen atom, a sulfur atom, or a selenium atom, and
*-S.sup.A-T.sup.AFormula A in Formula A, S.sup.A represents a single bond, an alkylene group, an alkenylene group, an alkynylene group, O, S, NR.sup.L1, C(O), C(O)O, C(O)NR.sup.L1, S(O).sub.2, OR.sup.L2, or a group including a combination of at least two thereof, R.sup.L1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, R.sup.L2 represents an alkylene group, an arylene group, or a divalent heterocyclic group, T.sup.A represents a halogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a cyano group, a hydroxy group, a formyl group, a carboxy group, a thiol group, a sulfo group, a phosphoryl group, a boryl group, a vinyl group, an ethynyl group, a trialkylsilyl group, or a trialkoxysilyl group, and * represents a binding site to the methine group at the center of the methine chain.

2. The dispersion according to claim 1, wherein the medium is a liquid.

3. The dispersion according to claim 1, wherein the medium is a liquid including water.

4. The dispersion according to claim 1, wherein the medium includes water and an organic solvent having a boiling point of 100 C. or higher under 101.325 kPa.

5. The dispersion according to claim 1, which is an ink composition.

6. The dispersion according to claim 1, which is an ink composition for ink jet recording.

7. An ink jet recording method comprising: a step of applying the dispersion according to claim 5 to a substrate.

8. A recorded material comprising: a substrate; and a near infrared absorbing image that is a dry material of the dispersion according to claim 5 and is disposed on the substrate.

9. A recorded material comprising: a substrate; and a near infrared absorbing image disposed on the substrate, wherein the near infrared absorbing image includes a colorant represented by the following Formula 1, and an absorption maximum of the near infrared absorbing image is in a range of 700 nm to 1,200 nm, ##STR00037## in Formula 1, L.sup.1 represents a methine chain consisting of 5 or 7 methine groups, a methine group at a center of the methine chain has a substituent represented by the following Formula A, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, and X's each independently represent an oxygen atom, a sulfur atom, or a selenium atom, and
*-S.sup.A-T.sup.AFormula A in Formula A, S.sup.A represents a single bond, an alkylene group, an alkenylene group, an alkynylene group, O, S, NR.sup.L1, C(O), C(O)O, C(O)NR.sup.L1, S(O).sub.2, OR.sup.L2, or a group including a combination of at least two thereof, R.sup.L1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, R.sup.L2 represents an alkylene group, an arylene group, or a divalent heterocyclic group, T.sup.A represents a halogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a cyano group, a hydroxy group, a formyl group, a carboxy group, a thiol group, a sulfo group, a phosphoryl group, a boryl group, a vinyl group, an ethynyl group, a trialkylsilyl group, or a trialkoxysilyl group, and * represents a binding site to the methine group at the center of the methine chain.

10. A compound represented by the following Formula 1, ##STR00038## in Formula 1, L.sup.1 represents a methine chain consisting of 5 or 7 methine groups, a methine group at a center of the methine chain has a substituent represented by the following Formula A, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, and X's each independently represent an oxygen atom, a sulfur atom, or a selenium atom, and
*-S.sup.A-T.sup.AFormula A in Formula A, S.sup.A represents a single bond, an alkylene group, an alkenylene group, an alkynylene group, O, S, NR.sup.L1, C(O), C(O)O, C(O)NR.sup.L1, S(O).sub.2, OR.sup.L2, or a group including a combination of at least two thereof, R.sup.L1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, R.sup.L2 represents an alkylene group, an arylene group, or a divalent heterocyclic group, T.sup.A represents a halogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a cyano group, a hydroxy group, a formyl group, a carboxy group, a thiol group, a sulfo group, a phosphoryl group, a boryl group, a vinyl group, an ethynyl group, a trialkylsilyl group, or a trialkoxysilyl group, and * represents a binding site to the methine group at the center of the methine chain.

11. The compound according to claim 10, wherein in Formula 1, at least one selected from the group consisting of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 is a hydrogen atom.

12. The compound according to claim 10, wherein the compound represented by Formula 1 is a compound represented by the following Formula 2, ##STR00039## in Formula 2, L represents a methine chain consisting of 5 or 7 methine groups, a methine group at a center of the methine chain has a substituent represented by the following Formula A, R.sup.5 and R.sup.7 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, R.sup.6 and R.sup.8 each independently represent an alkyl group, a halogen atom, an alkenyl group, an aryl group, a monovalent heterocyclic group, a nitro group, a cyano group, OR.sup.L3, C(O)R.sup.L3, C(O)OR.sup.L3, OC(O)R.sup.L3, N(R.sup.L3).sub.2, NHC(O)R.sup.L3, C(O)N(R.sup.L3).sub.2, NHC(O)OR.sup.L3, OC(O)N(R.sup.L3).sub.2, NHC(O)N(R.sup.L3).sub.2, SR.sup.L3, S(O).sub.2R.sup.L3, S(O).sub.2OR.sup.L3, NHS(O).sub.2R.sup.L3, or S(O).sub.2N(R.sup.L3).sub.2, R.sup.L3's each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a monovalent heterocyclic group, n's each independently represent an integer of 1 to 5, and X's each independently represent an oxygen atom, a sulfur atom, or a selenium atom, and
*-S.sup.A-T.sup.AFormula A in Formula A, S.sup.A represents a single bond, an alkylene group, an alkenylene group, an alkynylene group, O, S, NR.sup.L1, C(O), C(O)O, C(O)NR.sup.L1, S(O).sub.2, OR.sup.L2, or a group including a combination of at least two thereof, R.sup.L1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, R.sup.L2 represents an alkylene group, an arylene group, or a divalent heterocyclic group, T.sup.A represents a halogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a cyano group, a hydroxy group, a formyl group, a carboxy group, a thiol group, a sulfo group, a phosphoryl group, a boryl group, a vinyl group, an ethynyl group, a trialkylsilyl group, or a trialkoxysilyl group, and * represents a binding site to the methine group at the center of the methine chain.

13. The compound according to claim 12, wherein in Formula 2, at least one selected from the group consisting of R.sup.5, R.sup.6, R.sup.7, and R.sup.8 has a hydrogen-bonding group.

Description

EXAMPLES

[0503] Hereinafter, the present disclosure will be described in detail using Examples. Materials, used amounts, ratios, treatment details, treatment procedures, and the like shown in the following examples can be appropriately changed within a range not departing from the scope of the present disclosure. Accordingly, the scope of the present disclosure is not limited to the following specific examples. In the following Examples, unless specified otherwise, part(s) and % represent part(s) by mass and mass %.

[0504] Hereinafter, Compounds 1 to 115 according to Examples represent the same compounds as Compounds 1 to 115 shown in the specific examples of the specific colorant represented by Formula 1.

[0505] [Synthesis of Compound 1]

[0506] The compound 1 was synthesized according to the following scheme.

##STR00028##

[0507] 225.0 g of 3-aminoacetanilide, 594.0 g of methanol, 139.7 g of sodium cyanide, 1350 g of water, and 135.3 g of acetic acid (AcOH) were added to a flask, and the solution was stirred at 20 C. for 1 hour. By separating crystals precipitated in the reaction solution by filtration, 216.6 g of a compound 1-A was obtained.

[0508] 215.0 g of the compound 1-A, 3020 g of methanol, 178.2 g of diethyl malonate, and 214.6 g of sodium methoxide 28% methanol solution (SM-28) were added to a flask, and the solution was stirred at 65 C. for 6 hours.

[0509] By returning the temperature of the obtained reaction solution to 20 C. and separating crystals precipitated in the reaction solution by filtration, 198.0 g of a compound 1-B was obtained.

[0510] 195.0 g of the obtained compound 1-B, 975.0 g of water were added to a flask, 5% hydrochloric acid aqueous solution was added until the pH of the reaction solution was 2.0, and the solution was stirred at 20 C. for 1 hour.

[0511] By separating crystals precipitated in the reaction solution by filtration, 175.0 g of a compound 1-C was obtained.

[0512] 25.0 g of the obtained compound 1-C, 136.2 g of N,N-dimethylformamide, and 12.7 g of lithium acetate (LiOAc) were added to a flask, the solution was stirred at 20 C. for 10 minutes, 15.6 g of a compound 1-D was added, and the solution was stirred at 20 C. for 4 hours. 156.3 g of water was added to the obtained reaction solution, the solution was stirred at 20 C. for 1 hour, 247.5 g of methanol was added, and the solution was stirred at 20 C. for 1 hour.

[0513] By separating crystals precipitated in the reaction solution by filtration, 28.4 g of the compound 1 was obtained.

[0514] (Verification of Compound 1)

[0515] NMR spectrum of Compound 1: .sup.1H-NMR (heavy DMSO) 10.7 (2H, s), 10.0 (2H, s), 8.7 (2H, m), 7.9-7.6 (2H, m), 7.6-7.0 (10H, m), 6.9-6.7 (2H, m), 2.0 (6H, s)

[0516] It was verified from the NMR spectrum that the obtained compound 1 had the structure of the compound 1 as the above-described exemplary compound.

[0517] (Synthesis of Compounds 2 to 115)

[0518] Compounds 2 to 115 were obtained by performing the same synthesis as the synthesis of the compound 1, except that 3-aminoacetanilide and the compound 1-D were changed to compounds having the corresponding structures.

[0519] [Synthesis of Compound 2]

[0520] The compound 2 was synthesized according to the following scheme.

##STR00029##

[0521] 225.0 g of the compound 1-A, 1190 g of 2-propanol (IPA), and 850 g of 35% hydrochloric acid were added to a flask, and the solution was stirred at 65 C. for 12 hours.

[0522] By returning the temperature of the obtained reaction solution to 20 C. and separating crystals precipitated in the reaction solution by filtration, 199.0 g of a compound 2-A was obtained.

[0523] 195.0 g of the obtained compound 2-A, 733.0 g of N,N-dimethylacetamide, and 105.0 g triethylamine (Et.sub.3N) were added to a flask, 113.0 g of propionyl chloride (nPrCOCl) was added at 0 C., and the solution was stirred at room temperature for 1 hour.

4875 g of water was added to the obtained reaction solution, the solution was stirred for 30 minutes, and crystals precipitated in the reaction solution were separated by filtration. As a result, 223.0 g of a compound 2-B was obtained.

[0524] 200.0 g of the obtained compound 2-B, 2800 g of methanol, 434.3 g of diethyl malonate, and 523.2 g of sodium methoxide 28% methanol solution (SM-28) were added to a flask, and the solution was stirred at 65 C. for 4 hours.

[0525] The temperature of the obtained reaction solution was returned to 20 C., 9500 g of ethyl acetate was added, and the solution was stirred for 30 minutes. By separating crystals precipitated in the reaction solution by filtration, 248.5 g of a compound 2-C was obtained.

[0526] 200.0 g of the obtained compound 2-C and 1000 g of water (super pure water: SPW) were added to a flask, 5% hydrochloric acid aqueous solution was added until the pH of the reaction solution was 2.0, and the solution was stirred at 20 C. for 1 hour.

[0527] By separating crystals precipitated in the reaction solution by filtration, 182.0 g of a compound 2-D was obtained.

[0528] 25.0 g of the obtained compound 2-D, 136.2 g of N,N-dimethylformamide (DMF), and 11.4 g of lithium acetate (LiOAc) were added to a flask, the solution was stirred at 20 C. for 10 minutes, 14.1 g of the compound 1-D was added, and the solution was stirred at 20 C. for 4 hours. 156.3 g of water was added to the obtained reaction solution, the solution was stirred at 20 C. for 1 hour, 247.5 g of methanol was added, and the solution was stirred at 20 C. for 1 hour.

[0529] By separating crystals precipitated in the reaction solution by filtration, 28.1 g of the compound 2 was obtained.

[0530] Verification of Compound 2)

[0531] NMR spectrum of Compound 2: .sup.1H-NMR (heavy DMSO) 10.7 (2H, s), 9.9 (2H, s), 8.7 (2H, m), 7.9-7.6 (2H, m), 7.6-7.1 (10H, m), 6.9-6.7 (2H, m), 2.3 (4H, t, J=7.0 Hz), 1.6 (4H, m), 0.9 (6H, t, J=8.0 Hz)

[0532] It was verified from the NMR spectrum that the obtained compound 2 had the structure of the compound 2 as the above-described exemplary compound.

[0533] [Synthesis of Compound 3]

[0534] The compound 3 was synthesized according to the following scheme.

##STR00030##

[0535] 180.0 g of the compound 2-A, 676.8 g of N,N-dimethylacetamide (DMAc), and 97.1 g triethylamine (Et.sub.3N) were added to a flask, 134.9 g of benzoyl chloride (BzCl) was added at 0 C., and the solution was stirred at room temperature for 1 hour.

[0536] 4500 g of water was added to the obtained reaction solution, the solution was stirred for 30 minutes, and crystals precipitated in the reaction solution were separated by filtration. As a result, 235.2 g of a compound 3-A was obtained.

[0537] 200.0 g of the obtained compound 3-A, 2800 g of methanol (MeOH), 376.5 g of diethyl malonate (CH.sub.2(CO.sub.2Et).sub.2, and 453.5 g of sodium methoxide 28% methanol solution (SM-28) were added to a flask, and the solution was stirred at 65 C. for 4 hours.

[0538] The temperature of the obtained reaction solution was returned to 20 C., 9500 g of ethyl acetate was added, and the solution was stirred for 30 minutes. By separating crystals precipitated in the reaction solution by filtration, 238.2 g of a compound 3-B was obtained.

[0539] 200.0 g of the obtained compound 3-B, 1000 g of water were added to a flask, 5% hydrochloric acid aqueous solution was added until the pH of the reaction solution was 2.0, and the solution was stirred at 20 C. for 1 hour.

[0540] By separating crystals precipitated in the reaction solution by filtration, 183.5 g of a compound 3-C was obtained.

[0541] 25.0 g of the obtained compound 3-C, 136.2 g of N,N-dimethylformamide, and 10.2 g of lithium acetate were added to a flask, the solution was stirred at 20 C. for 10 minutes, 12.6 g of the compound 1-D was added, and the solution was stirred at 20 C. for 4 hours. 156.3 g of water was added to the obtained reaction solution, the solution was stirred at 20 C. for 1 hour, 247.5 g of methanol was added, and the solution was stirred at 20 C. for 1 hour.

[0542] By separating crystals precipitated in the reaction solution by filtration, 28.5 g of the compound 3 was obtained.

[0543] (Verification of Compound 3)

[0544] NMR spectrum of Compound 3: .sup.1H-NMR (heavy DMSO) 10.7 (2H, s), 10.3 (2H, s), 8.7 (2H, m), 8.0-7.9 (4H, m), 7.9-7.7 (4H, m), 7.7-7.5 (8H, m), 7.5-7.1 (6H, m), 7.0-6.8 (2H, m)

[0545] It was verified from the NMR spectrum that the obtained compound 3 had the structure of the compound 3 as the above-described exemplary compound.

[0546] [Synthesis of Compound 4]

[0547] The compound 4 was synthesized according to the following scheme.

##STR00031##

[0548] 190.0 g of the compound 2-A, 714.4 g of N,N-dimethylacetamide, and 102.5 g of triethylamine were added to a flask, 180.3 g of isonicotinoyl chloride hydrochloride was added at 0 C., and the solution was stirred at room temperature for 1 hour.

[0549] 4500 g of water was added to the obtained reaction solution, the solution was stirred for 30 minutes, and crystals precipitated in the reaction solution were separated by filtration. As a result, 235.2 g of a compound 4-A was obtained.

[0550] 200.0 g of the obtained compound 4-A, 2800 g of methanol, 375.0 g of diethyl malonate, and 451.7 g of sodium methoxide 28% methanol solution were added to a flask, and the solution was stirred at 65 C. for 4 hours.

[0551] The temperature of the obtained reaction solution was returned to 20 C., 9500 g of ethyl acetate was added, and the solution was stirred for 30 minutes. By separating crystals precipitated in the reaction solution by filtration, 243.0 g of a compound 4-B was obtained.

[0552] 200.0 g of the obtained compound 4-B, 1000 g of water were added to a flask, 5% hydrochloric acid aqueous solution was added until the pH of the reaction solution was 2.0, and the solution was stirred at 20 C. for 1 hour.

[0553] By separating crystals precipitated in the reaction solution by filtration, 168.5 g of a compound 4-C was obtained.

[0554] 25.0 g of the obtained compound 4-C, 136.2 g of N,N-dimethylformamide, and 10.2 g of lithium acetate were added to a flask, the solution was stirred at 20 C. for 10 minutes, 12.6 g of the compound 1-D was added, and the solution was stirred at 20 C. for 4 hours. 156.3 g of water was added to the obtained reaction solution, the solution was stirred at 20 C. for 1 hour, 247.5 g of methanol was added, and the solution was stirred at 20 C. for 1 hour.

[0555] By separating crystals precipitated in the reaction solution by filtration, 26.9 g of the compound 4 was obtained.

[0556] (Verification of Compound 4)

[0557] NMR spectrum of Compound 4: .sup.1H-NMR (heavy DMSO) 10.7 (2H, s), 10.3 (2H, s), 8.7 (2H, m), 8.0-7.9 (4H, m), 7.9-7.7 (4H, m), 7.7-7.5 (8H, m), 7.5-7.1 (6H, m), 7.0-6.8 (2H, m)

[0558] It was verified from the NMR spectrum that the obtained compound 4 had the structure of the compound 4 as the above-described exemplary compound.

[0559] [Synthesis of Compound 7]

[0560] The compound 7 was synthesized according to the following scheme.

##STR00032##

[0561] 170.0 g of the compound 2-A, 639.2 g of N,N-dimethylacetamide, and 97.1 g of triethylamine were added to a flask, 107.9 g of phenyl isocyanate (PhNCO) was added at 0 C., and the solution was stirred at room temperature for 1 hour.

[0562] 4500 g of water was added to the obtained reaction solution, the solution was stirred for 30 minutes, and crystals precipitated in the reaction solution were separated by filtration. As a result, 225.3 g of a compound 7-A was obtained.

[0563] 200.0 g of the obtained compound 7-A, 2800 g of methanol, 355.6 g of diethyl malonate, and 428.3 g of sodium methoxide 28% methanol solution were added to a flask, and the solution was stirred at 65 C. for 4 hours.

[0564] The temperature of the obtained reaction solution was returned to 20 C., 9500 g of ethyl acetate was added, and the solution was stirred for 30 minutes. By separating crystals precipitated in the reaction solution by filtration, 235.3 g of a compound 7-B was obtained.

[0565] 200.0 g of the obtained compound 7-B, 1000 g of water were added to a flask, 5% hydrochloric acid aqueous solution was added until the pH of the reaction solution was 2.0, and the solution was stirred at 20 C. for 1 hour.

[0566] By separating crystals precipitated in the reaction solution by filtration, 182.2 g of a compound 7-C was obtained.

[0567] 25.0 g of the obtained compound 7-C, 136.2 g of N,N-dimethylformamide, and 9.8 g of lithium acetate were added to a flask, the solution was stirred at 20 C. for 10 minutes, 12.1 g of the compound 1-D was added, and the solution was stirred at 20 C. for 4 hours. 156.3 g of water was added to the obtained reaction solution, the solution was stirred at 20 C. for 1 hour, 247.5 g of methanol was added, and the solution was stirred at 20 C. for 1 hour.

[0568] By separating crystals precipitated in the reaction solution by filtration, 27.3 g of the compound 7 was obtained.

[0569] (Verification of Compound 7)

[0570] NMR spectrum of Compound 7: .sup.1H-NMR (heavy DMSO) 10.7 (2H, s), 8.7-8.6 (6H, m), 7.9-7.7 (2H, m), 7.5-7.1 (18H, m), 7.0-6.9 (2H, m), 6.9-6.7 (2H, m)

[0571] It was verified from the NMR spectrum that the obtained compound 7 had the structure of the compound 7 as the above-described exemplary compound.

[0572] [Synthesis of Compound 11]

[0573] The compound 11 was synthesized according to the following scheme.

##STR00033##

[0574] 160.0 g of the compound 2-A, 601.6 g of N,N-dimethylacetamide, and 86.3 g of triethylamine were added to a flask, 135.2 g of 4-fluorobenzoyl chloride was added at 0 C., and the solution was stirred at room temperature for 1 hour.

[0575] 4000 g of water was added to the obtained reaction solution, the solution was stirred for 30 minutes, and crystals precipitated in the reaction solution were separated by filtration. As a result, 221.5 g of a compound 11-A was obtained.

[0576] 200.0 g of the obtained compound 11-A, 2800 g of methanol, 351.7 g of diethyl malonate, and 423.6 g of sodium methoxide 28% methanol solution were added to a flask, and the solution was stirred at 65 C. for 4 hours.

[0577] The temperature of the obtained reaction solution was returned to 20 C., 9500 g of ethyl acetate was added, and the solution was stirred for 30 minutes. By separating crystals precipitated in the reaction solution by filtration, 225.0 g of a compound 11-B was obtained.

[0578] 200.0 g of the obtained compound 11-B, 1000 g of water were added to a flask, 5% hydrochloric acid aqueous solution was added until the pH of the reaction solution was 2.0, and the solution was stirred at 20 C. for 1 hour.

[0579] By separating crystals precipitated in the reaction solution by filtration, 176.6 g of a compound 11-C was obtained.

[0580] 25.0 g of the obtained compound 11-C, 136.2 g of N,N-dimethylformamide, and 9.7 g of lithium acetate were added to a flask, the solution was stirred at 20 C. for 10 minutes, 11.9 g of the compound 1-D was added, and the solution was stirred at 20 C. for 4 hours. 156.3 g of water was added to the obtained reaction solution, the solution was stirred at 20 C. for 1 hour, 247.5 g of methanol was added, and the solution was stirred at 20 C. for 1 hour.

[0581] By separating crystals precipitated in the reaction solution by filtration, 26.7 g of the compound 11 was obtained.

[0582] (Verification of Compound 11)

[0583] NMR spectrum of Compound 11: .sup.1H-NMR (heavy DMSO) 10.7 (2H, s), 10.3 (2H, s), 8.7 (2H, m), 8.0 (4H, m), 7.9-7.7 (4H, m), 7.6-7.5 (2H, m), 7.5-7.1 (10H, m), 7.0-6.8 (2H, m)

[0584] It was verified from the NMR spectrum that the obtained compound 11 had the structure of the compound 11 as the above-described exemplary compound.

[0585] [Synthesis of Compound 37]

[0586] The compound 37 was synthesized according to the following scheme.

##STR00034##

[0587] The compound 1-C as an intermediate was obtained using the same synthesis method as that of the compound 1.

[0588] 25.0 g of the obtained compound 1-C, 136.2 g of N,N-dimethylformamide, and 12.6 g of lithium acetate were added to a flask, the solution was stirred at 20 C. for 10 minutes, 15.5 g of a compound 37-a was added, and the solution was stirred at 20 C. for 4 hours. 156.3 g of water was added to the obtained reaction solution, the solution was stirred at 20 C. for 1 hour, 247.5 g of methanol was added, and the solution was stirred at 20 C. for 1 hour.

[0589] By separating crystals precipitated in the reaction solution by filtration, 29.4 g of the compound 37 was obtained.

[0590] (Verification of Compound 37)

[0591] NMR spectrum of Compound 37: .sup.1H-NMR (heavy DMSO) 10.7 (2H, s), 10.0 (2H, s), 8.0-7.6 (2H, m), 7.6-7.1 (13H, m), 6.9-6.7 (2H, m), 2.0 (6H, s)

[0592] It was verified from the NMR spectrum that the obtained compound 37 had the structure of the compound 37 as the above-described exemplary compound.

Near Infrared Absorbing Dispersion: Preparation of Ink Composition

Example 1

[0593] The respective components described in the following composition were dispersed according to the following (dispersion method 1), (dispersion method 2), and (dispersion method 3) to obtain three ink compositions including the specific colorant.

[0594] Composition [0595] Specific colorant (compound 1): 0.5 parts by mass [0596] Super pure water (specific resistance value: 18 M.Math.cm or higher): 78.8 parts by mass [0597] Propylene glycol: 19.7 parts by mass [0598] OLFINE E1010: 1 part by mass

[0599] Here, OLFINE E1010 was an acetylenic glycol surfactant manufactured by Nissin Chemical Co., Ltd.

[0600] (Dispersion Method 1)

[0601] The respective components having the above-described composition was stirred at 25 C. (normal temperature) for 2 hours using a stirrer and a stirring bar to obtain an ink composition.

[0602] (Dispersion Method 2)

[0603] The respective components having the above-described composition was stirred at 25 C. (normal temperature) for 2 hours using a paint shaker to obtain an ink composition.

[0604] (Dispersion Method 3)

[0605] The respective components having the above-described composition was stirred at 25 C. (normal temperature) for 5 hours using a paint shaker to obtain an ink composition.

Examples 2 to 115

[0606] Three ink compositions according to each of Examples 2 to 115 were prepared using the same preparation method as that of the ink composition according to Example 1, except that the compound 1 used in the above-described composition was changed to each of the compounds 2 to 115.

Comparative Example 1

[0607] An ink composition according to Comparative Example 1 was prepared using the same method as described in Example 1 of JP2008-144004A. A colorant included in the ink composition according to Comparative Example 1 (a colorant (20) described in paragraph 0030 of JP2008-144004A) was the same as the colorant compound having the structure represented by Formula 1, except that the counter cation was Mg.sup.2+.

Comparative Example 2

[0608] An ink composition according to Comparative Example 2 was prepared using the same method as that of Ink I-1 described in Example of JP2002-294107A.

Comparative Example 3

[0609] An ink composition according to Comparative Example 3 was prepared under the same conditions as in Example 1, except that the following solid dispersed dye 1 was used instead of Compound 1. The following solid dispersed dye 1 was synthesized using the same method as described in JP1999-282136A (JP-H11-282136A).

Solid Dispersed Dye 1

[0610] ##STR00035##

[0611] <Preparation of Recorded Material>

[0612] Each of the ink compositions according to Examples 1 to 115 and Comparative Examples 1 to 3 obtained using the above-described method was charged into an ink tank of an ink jet recording device (DMP-2831, manufactured by Fujifilm Dimatix Inc.), and was applied from an ink jet head to OK Top Coat Paper (manufactured by Oji Paper Co., Ltd.) to record a solid image. As a result, each of recorded materials A-1 to A-115 and comparative recorded materials CA-1 to CA-3 was obtained.

[0613] Solid image refers to a surface image that is formed by applying an ink composition having a halftone dot rate of 100%.

[0614] <Evaluation>

[0615] [Measurement of Properties]

[0616] The following measurement and evaluation were obtained on the obtained ink compositions according to Examples 1 to 115, the ink compositions according to Comparative Examples 1 to 3, and the recorded materials A-1 to A-115 and the comparative recorded materials CA-1 to CA-3. The results of the measurement and evaluation are shown in Tables 5 to 9 below.

[0617] In the column Compound Used of Tables 5 to 9, the kind of the specific colorant included in the ink composition was shown using the reference numeral of the exemplary compound. In addition, the ink compositions according to Comparative Examples 1 to 3 did not include the specific colorant and were represented by - representing not including.

[0618] For the evaluation of the properties other than dispersibility, each of the ink compositions prepared using the dispersion method 2 was used.

[0619] [Dispersibility]

[0620] An ink composition was prepared using each of the dispersions prepared using the dispersion methods 1 to 3, the ink composition was charged into an ink tank of an ink jet recording device (DMP-2831, manufactured by Fujifilm Dimatix Inc.), and ink jettability was evaluated using the following method. The evaluation result was set as an index for dispersibility.

[0621] By observing an ink composition jetting portion of the ink jet head by visual inspection while jetting the ink composition from the ink jet head, the ink jettability was evaluated based on the following evaluation standards.

[0622] In the following description, Defective Nozzle Number Ratio (%) refers to a ratio of the number of defective nozzles to the number of all the nozzles.

[0623] Evaluation Standards of Ink Jettability

[0624] 1: the defective nozzle number ratio was lower than 10%

[0625] 2: the defective nozzle number ratio was 10% or higher

[0626] Evaluation Standards of Dispersibility

[0627] A: the ink jettability was 1 in all the dispersion methods

[0628] B: the ink jettability was 1 in two of the dispersion methods

[0629] C: the ink jettability was 1 in one of the dispersion methods

[0630] D: the ink jettability was 2 in all the dispersion methods

[0631] [Invisibility]

[0632] Invisibility was evaluated using the recorded materials A-1 to A-115 and the comparative recorded materials CA-1 to CA-3. Regarding invisibility, the optical density (OD) at 450 nm and the optical density at the absorption maximum were measured using a spectrophotometer UV-3100PC (manufactured by Shimadzu Corporation) including a 150 mm (p large integrating sphere attachment LISR-3100 (manufactured by Shimadzu Corporation) and were determined based on the following evaluation standards. The results are shown in Tables 5 to 9.

[0633] In a case where the evaluation result is A, B, or C, there is no problem in practice. A or B is preferable, and A is more preferable.

[0634] Evaluation Standards

[0635] A: Optical density at 450 nm/Optical density at Absorption Maximum was 1/10 (0.1) or lower

[0636] B: Optical density at 450 nm/Optical density at Absorption Maximum was higher than 1/10 and 1/7 (0.14) or lower

[0637] C: Optical density at 450 nm/Optical density at Absorption Maximum was higher than 1/7 and (0.2) or lower

[0638] D: Optical density at 450 nm/Optical density at Absorption Maximum was higher than

[0639] [Light Fastness]

[0640] Under the same conditions as those of the recorded materials A-1 to A-115 and the comparative recorded materials CA-1 to CA-3, three recorded materials were prepared using each of the ink compositions for ink jet recording such that the optical densities (OD; reflection densities) at the absorption maximum were 0.5, 1, and 1.5, respectively. By adjusting the jetting amount of the ink composition for ink jet recording, the optical density can be adjusted.

[0641] Each of the recorded materials was irradiated with xenon light (85000 lx) using a weather meter (ATLAS C. 165) for 6 days. The optical density of the recorded material at the absorption maximum was measured before and after the irradiation of xenon light, and (Optical Density after Irradiation)/(Optical Density before Irradiation)=Colorant Residue Rate was evaluated.

[0642] All the optical densities were measured using a spectrophotometer UV-3100PC (manufactured by Shimadzu Corporation) including a 150 mm large integrating sphere attachment LISR-3100.

[0643] In a case where the evaluation result is A, B, or C, there is no problem in practice. A or B is preferable, and A is more preferable.

[0644] Evaluation Standards

[0645] A: the colorant residue rate was 90% or higher at all the densities

[0646] B: the colorant residue rate was 75% or higher and lower than 90% at all the densities

[0647] C: the colorant residue rate was lower than 75% at at least one density but was 60% or higher at all the densities

[0648] D: the colorant residue rate was lower than 60% at at least one density

[0649] [Moist Heat Resistance]

[0650] Using the same method as the method of preparing the recorded material in the evaluation of light fastness, three recorded materials were prepared using each of the ink jet recording inks such that the optical densities (OD; reflection densities) at the absorption maximum were 0.5, 1, and 1.5, respectively.

[0651] Each of the recorded materials was left to stand in a box set to 60 C. and a humidity of 90% for 7 days. The optical density of the image after standing was measured, and (Optical Density after Standing)/(Optical Density before Standing)=Colorant Residue Rate was evaluated.

[0652] All the optical densities were measured using a spectrophotometer UV-3100PC (manufactured by Shimadzu Corporation) including a 150 mm large integrating sphere attachment LISR-3100.

[0653] In a case where the evaluation result is A, B, or C, there is no problem in practice. A or B is preferable, and A is more preferable.

[0654] Evaluation Standards

[0655] A: the colorant residue rate was 90% or higher at all the densities

[0656] B: the colorant residue rate was 75% or higher and lower than 90% at all the densities

[0657] C: The colorant residue rate was lower than 75% at at least one density but was 60% or higher at all the densities

[0658] D: The colorant residue rate was lower than 60% at at least one density

TABLE-US-00005 TABLE 5 Ink Recorded Material (Near Infrared Absorbing image) Specific Composition Light Moist Heat Colorant Dispersibility Invisibility Fastness Resistance Example 1 Compound 1 A A A A Example 2 Compound 2 A A A A Example 3 Compound 3 A A A A Example 4 Compound 4 A A A A Example 5 Compound 5 A A A A Example 6 Compound 6 A A A A Example 7 Compound 7 A A A A Example 8 Compound 8 A A A A Example 9 Compound 9 A A A A Example 10 Compound 10 A A A A Example 11 Compound 11 A A A A Example 12 Compound 12 A A A A Example 13 Compound 13 A A A A Example 14 Compound 14 A A A A Example 15 Compound 15 A A A A Example 16 Compound 16 A A A A Example 17 Compound 17 A A A A Example 18 Compound 18 A A A A Example 19 Compound 19 A A A A Example 20 Compound 20 A A A A Example 21 Compound 21 A A A A Example 22 Compound 22 A A A A Example 23 Compound 23 A A A A Example 24 Compound 24 A A A A Example 25 Compound 25 A A A A

TABLE-US-00006 TABLE 6 Ink Recorded Material (Near Infrared Absorbing image) Specific Composition Light Moist Heat Colorant Dispersibility Invisibility Fastness Resistance Example 26 Compound 26 A A A A Example 27 Compound 27 A A A A Example 28 Compound 28 A A A A Example 29 Compound 29 A A A A Example 30 Compound 30 A A A A Example 31 Compound 31 A A A A Example 32 Compound 32 A A A A Example 33 Compound 33 A A A A Example 34 Compound 34 A A A A Example 35 Compound 35 A A A A Example 36 Compound 36 A A A A Example 37 Compound 37 A A A A Example 38 Compound 38 A A A A Example 39 Compound 39 A A A A Example 40 Compound 40 A A A A Example 41 Compound 41 A A A A Example 42 Compound 42 A A A A Example 43 Compound 43 A A A A Example 44 Compound 44 A A A A Example 45 Compound 45 A A A A Example 46 Compound 46 A A A A Example 47 Compound 47 A A A A Example 48 Compound 48 A A A A Example 49 Compound 49 A A A A Example 50 Compound 50 A A A A

TABLE-US-00007 TABLE 7 Ink Recorded Material (Near Infrared Absorbing image) Specific Composition Light Moist Heat Colorant Dispersibility Invisibility Fastness Resistance Example 51 Compound 51 A A A A Example 52 Compound 52 A A A A Example 53 Compound 53 A A A A Example 54 Compound 54 A A A A Example 55 Compound 55 A A A A Example 56 Compound 56 A A A A Example 57 Compound 57 A A A A Example 58 Compound 58 A A A A Example 59 Compound 59 A A A A Example 60 Compound 60 A A A A Example 61 Compound 61 A A A A Example 62 Compound 62 A A A A Example 63 Compound 63 A A A A Example 64 Compound 64 A A A A Example 65 Compound 65 A A A A Example 66 Compound 66 A A A A Example 67 Compound 67 A A A A Example 68 Compound 68 A A A A Example 69 Compound 69 A A A A Example 70 Compound 70 A A A A Example 71 Compound 71 A A A A Example 72 Compound 72 A A A A Example 73 Compound 73 A A A A Example 74 Compound 74 A A A A Example 75 Compound 75 A A A A

TABLE-US-00008 TABLE 8 Ink Recorded Material (Near Infrared Absorbing image) Specific Composition Light Moist Heat Colorant Dispersibility Invisibility Fastness Resistance Example 76 Compound 76 A A A A Example 77 Compound 77 A A A A Example 78 Compound 78 A A A A Example 79 Compound 79 A A A A Example 80 Compound 80 A A A A Example 81 Compound 81 A A A A Example 82 Compound 82 A A A A Example 83 Compound 83 A A A A Example 84 Compound 84 A A A A Example 85 Compound 85 A A A A Example 86 Compound 86 A A A A Example 87 Compound 87 A A A A Example 88 Compound 88 A A A A Example 89 Compound 89 A A A A Example 90 Compound 90 A A A A Example 91 Compound 91 A A A A Example 92 Compound 92 A A A A Example 93 Compound 93 A A A A Example 94 Compound 94 A A A A Example 95 Compound 95 A A A A Example 96 Compound 96 A A A A Example 97 Compound 97 A A A A Example 98 Compound 98 A A A A Example 99 Compound 99 A A A A Example 100 Compound 100 A A A A

TABLE-US-00009 TABLE 9 Ink Recorded Material (Near Infrared Absorbing image) Specific Composition Light Moist Heat Colorant Dispersibility Invisibility Fastness Resistance Example 101 Compound 101 A A A A Example 102 Compound 102 A A A A Example 103 Compound 103 A A A A Example 104 Compound 104 A A A A Example 105 Compound 105 A A A A Example 106 Compound 106 A A A A Example 107 Compound 107 A A A A Example 108 Compound 108 A A A A Example 109 Compound 109 A A A A Example 110 Compound 110 A B B B Example 111 Compound 111 A A B C Example 112 Compound 112 A A A A Example 113 Compound 113 A A A A Example 114 Compound 114 A A A A Example 115 Compound 115 A A A A Comparative D A B B Example 1 Comparative D D C C Example 2 Comparative D D D D Example 3

[0659] It was found from the results of Tables 5 to 9 that, in the ink compositions (dispersions) according to Examples 1 to 115, the dispersibility of the specific colorant was excellent in all the three inks. In addition, the image in the recorded material as the dry material of each of the ink compositions according to Examples 1 to 115 was an image having absorption in the near infrared range, and invisibility was excellent. Further, it was verified that there was no problem in practice regarding the light fastness and moist heat resistance of the obtained image.

[0660] In the image obtained using the ink composition according to Comparative Example 1 including the colorant compound having a structure similar to Formula 1 and having absorption in the near infrared range, invisibility, light fastness, and moist heat resistance were excellent, but the colorant compound in which the counter cation was a lithium ion was included. Therefore, it can be seen that it was difficult to disperse the colorant as the ink composition.

Preparation of Resin Kneaded Material

Example 116

[0661] 0.02 g of the compound 1 and 10 g of a polyethylene terephthalate resin (Tg: 60 C.) were set to a twin screw kneader and were kneaded at 120 C. at 200 rpm for 5 minutes to prepare a resin kneaded material (the dispersion according to the embodiment of the present disclosure).

[0662] In the absorption spectrum of the obtained resin kneaded material, the absorption maximum was 800 nm or higher, Optical density at 450 nm/Optical density at Absorption Maximum was 1/10 (0.1) or lower, and near infrared absorption properties and invisibility were excellent.

[0663] The disclosure of Japanese Patent Application No. 2018-027438 filed on Feb. 19, 2018 is incorporated herein in its entirety.

[0664] All publications, patent applications, and technical standards mentioned in the present disclosure are herein incorporated by reference to the same extent as if each individual publication, patent application, or technical standard was specifically and individually indicated to be incorporated by reference.