COLORED DISPERSION, RECORDING MEDIUM, AND HYDROPHOBIC FIBER PRINTING METHOD

Abstract

A colored dispersion that contains (A) a dye derivative, (B) a water-insoluble dye, (C) a dispersant, and water. The (A) component contains an anthraquinone-based compound represented by formula (a1), the (C) component contains a polyoxyethylene aryl phenyl ether and a polyoxyethylene aryl phenyl ether sulfate, and the mass ratio ((B)/(A)) of the (B) component with respect to the (A) component satisfies the relationship 400>(B)/(A)>3.125. A recording medium having the colored dispersion adhered thereto and a hydrophobic fiber printing method using the colored dispersion. In formula (a1), each of R.sup.a1-R.sup.a5 is a hydrogen atom, and X.sup.a1 is a group represented by formula (a4). In formula (a4), Z.sup.a3 is an optionally-substituted amino group

##STR00001##

Claims

1. A colored dispersion liquid, comprising: (A) a dye derivative, (B) a water-insoluble dye, (C) a dispersant, and water, wherein the dye derivative (A) comprises an anthraquinone-based compound represented by the following formula (a1): ##STR00012## wherein R.sup.a1 to R.sup.a each independently represents a hydrogen atom, a C1 to C4 alkyl group which may have a substituent, a cyclic alkyl group which may have a substituent, an aryl group which may have a substituent, or a halogen atom; n.sup.1 and n.sup.2 each independently represents an integer of 1 to 4, when n.sup.1 represents an integer of 2 to 4, R.sup.a3 in the number of n.sup.1 may be the same as or different from each other, when n.sup.2 represents an integer of 2 to 4, R.sup.a5 in the number of n.sup.2 may be the same as or different from each other, and X.sup.a1 represents a group represented by any one of the following formulas (a2) to (a5): ##STR00013## wherein Z.sup.a1 represents an aliphatic hydrocarbon group which may have a substituent or an aromatic hydrocarbon group which may have a substituent, Z.sup.a2 represents an amino group which may have a substituent or an alkoxy group which may have a substituent, Z.sup.a3 represents an amino group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, a pyridinooxy group, or a halogen atom, and Z.sup.a4 represents a C1 to C4 alkyl group, wherein the dye derivative (A) does not simultaneously comprise a compound represented by the formula (a1) wherein X.sup.a1 represents a group represented by the formula (a4) and a compound represented by the formula (a1) wherein X.sup.a1 represents a group represented by the formula (a5), wherein the dispersant (C) comprises a polyoxyethylene arylphenyl ether and a polyoxyethylene arylphenyl ether sulfate, and wherein a mass ratio ((B)/(A)) of the water-insoluble dye (B) to the dye derivative (A) satisfies a relation of 400>(B)/(A)>3.125.

2. The colored dispersion liquid according to claim 1, wherein the mass ratio ((B)/(A)) of the water-insoluble dye (B) to the dye derivative (A) satisfies a relation of 400>(B)/(A)>19.

3. The colored dispersion liquid according to claim 1, wherein the anthraquinone-based compound represented by the formula (a1) comprises a compound represented by the following formula (a1-1): ##STR00014## wherein X.sup.a2 represents a hydrogen atom, a phenyl group, a n-butyl group, or a 3-ethoxypropyl group.

4. The colored dispersion liquid according to claim 1, wherein the water-insoluble dye (B) is a disperse dye.

5. The colored dispersion liquid according to claim 4, wherein the disperse dye is a disperse dye having an anthraquinone skeleton.

6. The colored dispersion liquid according to claim 5, wherein the disperse dye having an anthraquinone skeleton is a disperse dye represented by the following formula (b1): ##STR00015## wherein R.sup.b1 represents a hydrogen atom or substituent, p represents an integer of 0 to 6, and when p represents an integer of 2 to 6, R.sup.b1 in the number of p may be the same as or different from each other.

7. The colored dispersion liquid according to claim 6, wherein the disperse dye represented by the formula (b1) is C.I. Disperse Red 60.

8. A recording medium, comprising the colored dispersion liquid according to claim 1 adhered thereto.

9. The recording medium according to claim 8, wherein the recording medium is a hydrophobic fiber.

10. A method for textile printing of a hydrophobic fiber, comprising: printing by adhering a droplet of the colored dispersion liquid according to claim 1 to an intermediate recording medium to obtain a recorded image, and transferring the recorded image to the hydrophobic fiber by contacting a hydrophobic fiber with a surface of the intermediate recording medium on which the colored dispersion liquid is adhered, followed by heat treatment.

Description

EXAMPLES

[0104] In the following, the present invention is explained in more detail by way of the Examples; however, the present invention is not limited to these Examples. Unless otherwise indicated in the Examples, “part(s)” and “%” mean part(s) by mass and % by mass, respectively. Note that all of the aqueous dispersion liquids and magenta inks in the Examples are included in the colored dispersion liquids described above.

Synthesis Example 1: Synthesis of Anthraquinone-Based Compound H

[0105] Chlorosulfonic acid (28 parts) was cooled to 5° C. or less in an ice bath, Kayaset Red B (manufactured by Nippon Kayaku Co., Ltd., C.I. Disperse Red 60) (10 parts) was mixed at 10° C. or less, and the mixture was reacted while stirring at 30° C. for 20 hours. The resulting reaction solution was poured into iced water to precipitate crystals. The obtained crystals were filtered off, and then washed with pure water to obtain a reddish brown wet cake. Then, n-butylamine (11 parts) was mixed to water (25 parts), and the total amount of the wet cake was added at 30° C. The reaction was carried out under stirring at the same temperature for 20 hours, and the obtained reaction solution was poured into iced water to precipitate crystals. The obtained crystals were filtered off, washed with cold pure water, and then dried at 80° C., thereby obtaining an anthraquinone-based compound H (13 parts) represented by the following formula (a1-1-1).

##STR00010##

Synthesis Example 2: Synthesis of Anthraquinone-Based Compound I

[0106] Chlorosulfonic acid (28 parts) was cooled to 5° C. or less in an ice bath, Kayaset Red B (manufactured by Nippon Kayaku Co., Ltd., C.I. Disperse Red 60) (10 parts) was mixed at 10° C. or less, and the mixture was reacted while stirring at 30° C. for 20 hours. The resulting reaction solution was poured into iced water to precipitate crystals. The obtained crystals were filtered off, and then washed with pure water to obtain a reddish brown wet cake. Then, water (30 parts) and a 25% ammonia water (30 parts) were mixed, and the total amount of the wet cake was added at 30° C. The reaction was carried out under stirring at the same temperature for 20 hours, and the obtained reaction solution was poured into iced water to precipitate crystals. The obtained crystals were filtered off, washed with cold pure water, and then dried at 80° C., thereby obtaining an anthraquinone-based compound I (11.4 parts) represented by the following formula (a1-1-2).

##STR00011##

Examples 1 to 9: Preparation of Aqueous Dispersion Liquids 1 to 9

[0107] Glass beads with a diameter of 0.2 mm were added to mixtures each obtained by mixing the respective components to be added first described in Tables 1 to 2 below, and the mixtures were subjected to a dispersion treatment in a sand mill for about 15 hours under water cooling. To the obtained liquids, components to be added later described in Tables 1 to 2 were added to adjust dye contents to 15%, and then the obtained mixtures were filtered through a glass fiber filter paper GC-50 (pore diameter of the filter: 0.5 μm manufactured by Advantec Ltd.), thereby obtaining aqueous dispersion liquids 1 to 9.

Comparative Examples 1 to 4: Preparation of Aqueous Dispersions 10 to 13

[0108] Glass beads with a diameter of 0.2 mm were added to mixtures each obtained by mixing the respective components to be added first described in Table 3, and then the mixtures were subjected to a dispersion treatment in a sand mill for about 15 hours under water cooling. To the obtained liquids, components to be added later described in Table 3 were added to adjust the dye contents to 15%, and then filtered through a glass fiber filter paper GC-50 (ADVANTEC Co., Ltd., pore diameter of the filter: 0.5 μm) to obtain aqueous dispersions 10 to 13.

TABLE-US-00001 TABLE 1 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Aqueous Aqueous Aqueous Aqueous Aqueous Aqueous dispersion dispersion dispersion dispersion dispersion dispersion liquid 1 liquid 2 liquid 3 liquid 4 liquid 5 liquid 6 Components DR92 (A) 0.1 0.2 0.4 0.6 1 6 to be added DR60 (B) 20 20 20 20 20 20 first TS-2000 (C) 6 6 6 6 6 6 SM-57 (C) 8.6 8.6 8.6 8.6 8.6 8.6 Proxel GXL 0.13 0.13 0.13 0.13 0.13 0.13 Surfynol 0.27 0.27 0.27 0.27 0.27 0.27 104PG50 Ion-exchanged 53.8 53.7 53.5 53.3 52.9 47.9 water Components Ion-exchanged 44.4 44.4 44.4 44.4 44.4 44.4 to be added water later (B)/(A) 200 100 50 33.33 20 3.33

TABLE-US-00002 TABLE 2 Example 7 Example 8 Example 9 Aqueous Aqueous Aqueous dispersion dispersion dispersion liquid 7 liquid 8 liquid 9 Components Anthraquinone- 0.4 to be based compound added first H (A) Anthraquinone- 0.4 based compound I (A) DR146 (A) 0.4 DR60 (B) 20 20 20 TS-2000 (C) 6 6 6 SM-57 (C) 8.6 8.6 8.6 Proxel GXL 0.13 0.13 0.13 Surfynol 0.27 0.27 0.27 104PG50 Ion-exchanged 53.5 53.5 53.5 water Components Ion-exchanged 44.4 44.4 44.4 to be water added later (B)/(A) 50 50 50

TABLE-US-00003 TABLE 3 Comparative Comparative Comparative Comparative Example 1 Example 2 Example 3 Example 4 Aqueous Aqueous Aqueous Aqueous dispersion dispersion dispersion dispersion liquid 10 liquid 11 liquid 12 liquid 13 Components DR92 (A) 0.05 6.5 to be Anthraquinone- 0.4 added first based compound A DR60 (B) 20 20 20 20 TS-2000 (C) 6 6 6 6 SM-57 (C) 8.6 8.6 8.6 8.6 Proxel GXL 0.13 0.13 0.13 0.13 Surfynol 104PG50 0.27 0.27 0.27 0.27 Ion-exchanged 53.9 53.5 53.85 47.4 water Components Ion-exchanged 44.4 44.4 44.4 44.4 to be water added later (B)/(A) — — 400 3.08

[0109] In Tables 1 to 3, notations (A), (B), and (C) after the end of the component names indicate that the components are component (A), component (B), and component (C), respectively. Further, in Tables 1 to 3, numerical values of the respective components refer to the number of parts added. Furthermore, in Tables 1 to 3, values indicated to the second decimal places as the values of ratios (B)/(A) are values obtained by rounding up the third decimal places.

[0110] Abbreviations and the like in Tables 1 to 3 have the following meanings.

DR92: C.I. Disperse Red 92

DR146: C.I. Disperse Red 146

[0111] Anthraquinone-based compound A: Compound described as a dye derivative b in the PCT International Publication No. WO2017/038747

DR60: C.I. Disperse Red 60

[0112] TS-2000: Polyoxyethylene styrylphenyl ether (manufactured by Toho Chemical Industry Co., Ltd.)
SM-57: Polyoxyethylene styrylphenyl ether sulfate (manufactured by Toho Chemical Industry Co., Ltd.)
Proxel GXL: preservative antifungal agent (manufactured by Lonza)
Surfynol 104PG50: Surfynol 104 (acetylene glycol surfactant, manufactured by Air Products Japan Co., Ltd.) diluted with propylene glycol to 50% concentration

Examples 10 to 18: Preparation of Magenta Inks 1 to 9

[0113] Aqueous dispersion liquids 1 to 9 obtained in Examples 1 to 9 and the respective components described in Tables 4 to 5 below were mixed and stirred for 30 minutes, and then each of the resulting mixtures was filtered through a glass fiber filter paper GC-50 (manufactured by Advantec Ltd., pore diameter of the filter: 0.5 μm) to obtain magenta inks 1 to 9.

Comparative Examples 5 to 8: Preparation of Magenta Inks 10 to 13

[0114] Aqueous dispersion liquids 10 to 13 obtained in Comparative Examples 1 to 4 and each of the components described in Table 6 below were mixed and stirred for 30 minutes, and then filtered through a glass fiber filter paper GC-50 (manufactured by Advantec Ltd., pore diameter: 0.5 μm) to prepare magenta inks 10 to 13.

TABLE-US-00004 TABLE 4 Example 10 Example 11 Example 12 Example 13 Example 14 Example 15 Magenta Magenta Magenta Magenta Magenta Magenta ink 1 ink 2 ink 3 ink 4 ink 5 ink 6 Aqueous dispersion 50 liquid 1 Aqueous dispersion 50 liquid 2 Aqueous dispersion 50 liquid 3 Aqueous dispersion 50 liquid 4 Aqueous dispersion 50 liquid 5 Aqueous dispersion 50 liquid 6 Other Glycerin 15 15 15 15 15 15 components Propylene 10 10 10 10 10 10 glycol Methyl 5 5 5 5 5 5 triglycol BYK-348 0.8 0.8 0.8 0.8 0.8 0.8 TEA-80 0.1 0.1 0.1 0.1 0.1 0.1 Proxel GXL 0.1 0.1 0.1 0.1 0.1 0.1 Ion- Balance Balance Balance Balance Balance Balance exchanged water Total 100 100 100 100 100 100

TABLE-US-00005 TABLE 5 Example 16 Example 17 Example 18 Magenta Magenta Magenta ink 7 ink 8 ink 9 Aqueous dispersion 50 liquid 7 Aqueous dispersion 50 liquid 8 Aqueous dispersion 50 liquid 9 Other Glycerin 15 15 15 components Propylene 10 10 10 glycol Methyl 5 5 5 triglycol BYK-348 0.8 0.8 0.8 TEA-80 0.1 0.1 0.1 Proxel GXL 0.1 0.1 0.1 Ion- Balance Balance Balance exchanged water Total 100 100 100

TABLE-US-00006 TABLE 6 Comparative Comparative Comparative Comparative Example 5 Example 6 Example 7 Example 8 Magenta Magenta Magenta Magenta ink 10 ink 11 ink 12 ink 13 Aqueous dispersion 50 liquid 10 Aqueous dispersion 50 liquid 11 Aqueous dispersion 50 liquid 12 Aqueous dispersion 50 liquid 13 Other Glycerin 15 15 15 15 components Propylene 10 10 10 10 glycol Methyl 5 5 5 5 triglycol BYK-348 0.8 0.8 0.8 0.8 TEA-80 0.1 0.1 0.1 0.1 Proxel GXL 0.1 0.1 0.1 0.1 Ion- Balance Balance Balance Balance exchanged water Total 100 100 100 100

[0115] In Tables 4 to 6, numerical values of the respective components indicate the number of parts added. Abbreviations and the like in Tables 4 to 6 have the following meanings.

BYK-348: Polyether-modified polydimethylsiloxane (manufactured by Byk-Chemie GmnbH)
TEA-80: Triethanolamine (manufactured by Oxalis Chemicals Ltd.)
Proxel GXL: Preservative antifunagal agent (manufactured by Lonza)

<Evaluation>

[0116] Using each ink prepared as described above, the following evaluation tests were performed. Results are indicated in Tables 7 to 9 below.

[Viscosity Change Test]

[0117] With respect to each of the magenta inks, the viscosity at initial stage and the viscosity after storage for three days at 70° C. were measured using an E-type viscometer (TV-200, manufactured by Toki Sangyo Co., Ltd.) calibrated by a standard solution JS10 for viscometer calibration (manufactured by Nippon Grease Co., Ltd.) under condition of 25° C., at a rotational speed of 50 rpm. The viscosity change rate was calculated from the viscosity at the initial stage and the viscosity after the storage, and evaluated based on the following criteria. A or B represents a good evaluation, and C represents a poor evaluation.

—Evaluation Criteria—

[0118] A: The absolute value of change rate is less than 5%.
B: The absolute value of change rate is 5% or more and less than 15%.
C: The absolute value of change rate is 15% or more.

[Particle Size Change Test]

[0119] With respect to each of the magenta inks, the median diameter (D50, number average particle diameter) at initial stage and the median diameter after storage for three days at 70° C. were measured using a MICROTRAC UPA EX150 (manufactured by Microtrac BEL Corp.). The particle diameter change rate was calculated from the particle diameter at the initial stage and the particle diameter after the storage, and evaluated based on the following criteria. A or B represents a good evaluation and C or D represents a poor evaluation

—Evaluation Criteria—

[0120] A: The absolute change rate is less than 10%.
B: The absolute change rate is 10% or more and less than 20%.
C: The absolute change rate is 20% or more and less than 50%.
D: The change rate is 50% or more.

[Confirmation of Sedimentation Property]

[0121] With respect to each of the magenta inks stored for three days at 70° C., the presence or absence of sedimentation was visually confirmed and evaluated based on the following criteria. A or B represents a good evaluation, and C represents a poor evaluation.

—Evaluation Criteria—

[0122] A: No sedimentation is confirmed.
B: Slight sedimentation is confirmed.
C: The sedimentation is confirmed to a considerable extent.

[Confirmation of Filterability]

[0123] 10 mL of each of the magenta inks stored for three days at 70° C. was filtered through a filter having a pore size of 0.8 μm (manufactured by ADVANTEC Co., Ltd., DISMIC) and evaluated based on the following criteria. A or B represents a good evaluation, and C represents a poor evaluation.

—Evaluation Criteria—

[0124] A: All of the 10 mL of ink can pass through and there is little filtration resistance.
B: All of the 10 mL of ink can pass, but there is filtration resistance.
C: Filter clogging occurs and all of the 10 mL of ink cannot pass through.

TABLE-US-00007 TABLE 7 Example Example Example Example Example Example 10 11 12 13 14 15 Viscosity Change rate [%] 9 6 3 5 6 14 change test Evaluation B B A B B B Particle size Change rate [%] 8 2 7 9 13 17 change test Evaluation A A A A B B Sedimentation Evaluation A A A A B B property Filterability Evaluation A A A B B B

TABLE-US-00008 TABLE 8 Example Example Example 16 17 18 Viscosity Change rate [%] 7 7 6 change test Evaluation B B B Particle size Change rate [%] 9 8 9 change test Evaluation A A A Sedimentation Evaluation A A A property Filterability Evaluation A A A

TABLE-US-00009 TABLE 9 Comparative Comparative Comparative Comparative Example 5 Example 6 Example 7 Example 8 Viscosity Change rate [%] 6 3 −11 37 change test Evaluation B A B C Particle size Change rate [%] 50 13 21 18 change test Evaluation D B C B Sedimentation Evaluation C C B B property Filterability Evaluation B B B B

[0125] As is apparent from the results of Tables 7 to 9, all of the magenta inks of Examples 10 to 18 prepared using the aqueous dispersions of Examples 1 to 9 showed no significant change in viscosity or particle diameter after the storage at high temperature, or no sedimentation, exhibiting excellent storage stability. On the other hand, the magenta inks of Comparative Examples 5 to 8 prepared using the aqueous dispersions of Comparative Examples 1 to 4 were inferior in storage stability to the magenta inks of Examples 10 to 18.