JP7417430B2 - A colored dispersion, an ink composition using the same, a method for improving dispersion stability using the same, and a method for printing hydrophobic fibers. - Google Patents
A colored dispersion, an ink composition using the same, a method for improving dispersion stability using the same, and a method for printing hydrophobic fibers. Download PDFInfo
- Publication number
- JP7417430B2 JP7417430B2 JP2020008879A JP2020008879A JP7417430B2 JP 7417430 B2 JP7417430 B2 JP 7417430B2 JP 2020008879 A JP2020008879 A JP 2020008879A JP 2020008879 A JP2020008879 A JP 2020008879A JP 7417430 B2 JP7417430 B2 JP 7417430B2
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- JP
- Japan
- Prior art keywords
- colored dispersion
- parts
- dye
- examples
- fibers
- 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.)
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- 239000006185 dispersion Substances 0.000 title claims description 125
- 239000000835 fiber Substances 0.000 title claims description 83
- 230000002209 hydrophobic effect Effects 0.000 title claims description 31
- 238000000034 method Methods 0.000 title description 59
- 238000007639 printing Methods 0.000 title description 31
- 239000000203 mixture Substances 0.000 title description 23
- -1 polyoxyethylene Polymers 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 71
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 50
- 239000002270 dispersing agent Substances 0.000 claims description 46
- 239000001045 blue dye Substances 0.000 claims description 27
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 26
- 239000001043 yellow dye Substances 0.000 claims description 26
- 238000010521 absorption reaction Methods 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 229920000728 polyester Polymers 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 230000003595 spectral effect Effects 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000975 dye Substances 0.000 description 82
- 239000000976 ink Substances 0.000 description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- 238000000859 sublimation Methods 0.000 description 35
- 230000008022 sublimation Effects 0.000 description 35
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
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- 239000002609 medium Substances 0.000 description 29
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- 239000000123 paper Substances 0.000 description 21
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- 239000000839 emulsion Substances 0.000 description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 239000004753 textile Substances 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 11
- 238000004040 coloring Methods 0.000 description 10
- 238000007641 inkjet printing Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 239000000986 disperse dye Substances 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 7
- DQYSALLXMHVJAV-UHFFFAOYSA-M 3-heptyl-2-[(3-heptyl-4-methyl-1,3-thiazol-3-ium-2-yl)methylidene]-4-methyl-1,3-thiazole;iodide Chemical compound [I-].CCCCCCCN1C(C)=CS\C1=C\C1=[N+](CCCCCCC)C(C)=CS1 DQYSALLXMHVJAV-UHFFFAOYSA-M 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 238000010186 staining Methods 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 229920006243 acrylic copolymer Polymers 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 6
- 235000013877 carbamide Nutrition 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000005562 fading Methods 0.000 description 6
- 239000010419 fine particle Substances 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 108010070880 sigma K Proteins 0.000 description 6
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- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
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- WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 description 4
- FDTLQXNAPKJJAM-UHFFFAOYSA-N 2-(3-hydroxyquinolin-2-yl)indene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=NC2=CC=CC=C2C=C1O FDTLQXNAPKJJAM-UHFFFAOYSA-N 0.000 description 4
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 4
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 4
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- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 4
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- JGHGKNIEYCBHJY-UHFFFAOYSA-L magnesium;5-chloro-2-methyl-1,2-thiazol-3-one;dichloride Chemical compound [Mg+2].[Cl-].[Cl-].CN1SC(Cl)=CC1=O JGHGKNIEYCBHJY-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- PDDANVVLWYOEPS-UHFFFAOYSA-N nitrous acid;n-propan-2-ylpropan-2-amine Chemical compound [O-]N=O.CC(C)[NH2+]C(C)C PDDANVVLWYOEPS-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 description 1
- 229960004321 pentaerithrityl tetranitrate Drugs 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- LQPLDXQVILYOOL-UHFFFAOYSA-I pentasodium;2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O LQPLDXQVILYOOL-UHFFFAOYSA-I 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HXHCOXPZCUFAJI-UHFFFAOYSA-N prop-2-enoic acid;styrene Chemical compound OC(=O)C=C.C=CC1=CC=CC=C1 HXHCOXPZCUFAJI-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- LROWVYNUWKVTCU-STWYSWDKSA-M sodium sorbate Chemical compound [Na+].C\C=C\C=C\C([O-])=O LROWVYNUWKVTCU-STWYSWDKSA-M 0.000 description 1
- 235000019250 sodium sorbate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- XNRNJIIJLOFJEK-UHFFFAOYSA-N sodium;1-oxidopyridine-2-thione Chemical compound [Na+].[O-]N1C=CC=CC1=S XNRNJIIJLOFJEK-UHFFFAOYSA-N 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- 229950006451 sorbitan laurate Drugs 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Coloring (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Description
(A)下記式(1)で表される化合物、(B)C.I.Disperse Blue 360、(C)分散剤、を含み、(A)と(B)の総含有量を100とした場合、(B)の含有量が10以上90以下であり、(C)分散剤がポリオキシエチレンアリールフェニルエーテル系分散剤、ポリオキシエチレンアリールフェニルエーテルサルフェート系分散剤、からなる群から選択されるいずれかを少なくとも含む着色分散液、およびこれらが付着した記録メディア及び疎水性繊維の捺染方法に関する。 (A) a compound represented by the following formula (1), (B) C.I. I. Disperse Blue 360 contains (C) a dispersant, and when the total content of (A) and (B) is 100, the content of (B) is 10 or more and 90 or less, and (C) the dispersant is A colored dispersion containing at least one selected from the group consisting of a polyoxyethylene arylphenyl ether dispersant and a polyoxyethylene arylphenyl ether sulfate dispersant, and printing of recording media and hydrophobic fibers to which these are attached. Regarding the method.
近年、インクジェットによる無製版印刷を行なう記録方法が提案され、布等を含めた繊維の捺染においてもインクジェット捺染が行われている。従来のスクリーン印刷等の捺染方法と比較して、インクジェット印刷による捺染は、無製版であること、省資源であること、省エネルギーであること、及び高精細表現が容易であること、等、様々な利点がある。ここでポリエステル繊維等の疎水性繊維布は、一般に水に不溶性の色材により染色される。従って、インクジェット記録方法により疎水性繊維を捺染するための水性インクとしては、一般に水不溶性色材を水中に分散し、分散安定性等の性能が良好な分散インクを用いる必要がある。ポリエステル繊維を代表とする疎水性繊維へのインクジェット捺染方式は、大きく分けると以下2つの方法に大別される。繊維へ直接インクを付与(プリント)した後、高温スチーミング等の熱処理によりインク中の染料を繊維に染着させるダイレクトプリント法と、中間記録媒体(専用の転写紙等)にインクを付与(プリント)した後、中間記録媒体のインク付与面と疎水性繊維を重ね合わせた後、熱により染料を中間記録媒体から繊維側へ転写させる昇華転写法である。 In recent years, a recording method that performs plateless printing using inkjet has been proposed, and inkjet printing is also used for printing fibers including cloth. Compared to conventional textile printing methods such as screen printing, inkjet printing has various advantages such as no plate making, resource saving, energy saving, and ease of high-definition expression. There are advantages. Here, hydrophobic fiber cloth such as polyester fiber is generally dyed with a water-insoluble coloring material. Therefore, as an aqueous ink for printing hydrophobic fibers by an inkjet recording method, it is generally necessary to use a dispersion ink in which a water-insoluble coloring material is dispersed in water and has good performance such as dispersion stability. Inkjet printing methods for hydrophobic fibers, typically polyester fibers, can be broadly divided into the following two methods. The direct printing method involves applying ink directly to the fibers (printing) and then dyeing the fibers with the dye in the ink through heat treatment such as high-temperature steaming. ), the ink-applied surface of the intermediate recording medium and the hydrophobic fiber are superimposed, and then the dye is transferred from the intermediate recording medium to the fiber side using heat. This is a sublimation transfer method.
上記のうち昇華転写法は、のぼり旗等の捺染加工に主に用いられ、インク中には熱処理によるポリエステルへの転写適性に優れた易昇華型の染料が用いられる。加工工程としては、
(1)プリント工程:インクジェットプリンタにより染料インクを中間記録媒体に付与する工程、
(2)転写工程:熱処理により染料を中間記録媒体から繊維中に転写・染着させる工程、
の2工程が含まれ、市販の転写紙が広く使用できる為、繊維の前処理は必要とせず、また洗浄工程も省略されている。
Among the above, the sublimation transfer method is mainly used for printing flags and the like, and the ink uses an easily sublimable dye that has excellent transferability to polyester by heat treatment. As for the processing process,
(1) Printing process: a process of applying dye ink to the intermediate recording medium using an inkjet printer,
(2) Transfer process: process of transferring and dyeing the dye from the intermediate recording medium into the fiber by heat treatment,
Since commercially available transfer paper can be widely used, pretreatment of the fibers is not required, and the washing step is also omitted.
昇華転写法に使用されているインクジェットインクは、主として水性インクが使用され、水不溶性である分散染料群及び油溶性染料群から選ばれる昇華性染料を、分散剤を用いて水中に微粒子分散安定化した染料分散液とし、これに、保湿剤(乾燥防止剤)として水溶性有機溶剤、表面張力調整剤として界面活性剤、その他添加剤(pH調整剤、防腐・防黴剤、消泡剤等)を用いて、粒度・粘度・表面張力・pH等の物理特性(物性)を最適化してインク化されている(特許文献1参照)。また、インクジェットプリントにおいて、プリントヘッドのノズルが配列されたプレートからインクを安定的に吐出できる事が重要であるが、水系インクにおいてはノズルプレート近傍でインク中の水分の蒸発によって引き起こされる吐出トラブルが起こり易い。上記吐出トラブルとしては、例えば、プレート上でインク組成物が付着乾燥した場合に、プリンタのクリーニング動作で速やかに除去する事ができずに、印刷中にインクの吐出不良(飛行曲がり等)を引き起こすことなどが挙げられる。こうした課題を解決するために、例えば、昇華性を有する染料を用いてブラックを表現する際、通常、複数の染料を組み合わせてブラックが表現される。これは単独の染料では黒色の色相としては十分ではなく、また濃度も低いことが多いためであり、複数の染料を組み合せることにより、良好なブラックの表現が可能となる。しかし、このような、昇華性を有する染料を複数組み合わせたブラックインクで布帛を染色した場合、布帛の種類により、光源の分光分布を変えた光を布帛に照射すると、布帛に表現された黒色の色相が異なる色に見える場合があった。例えば、蛍光灯のような長波長の光が少ない照明下では、良好な色を表現できていても、長波長の光が多い太陽光下では、赤みがかって見えたり、その逆に、太陽光の下では良好な色を表現できていても、蛍光灯の下では青みがかって見えることがあった。このように、照明光源による物の色の見え方に及ぼす特性を、一般に「演色性」といい、この演色性の影響による色相の変化が少ないブラックインクが求められていた。さらに、インクジェットインクには、良好な射出性も求められ、染料がインク中で不安定であったり、分散が不十分であったりすると、インクジェットヘッドにおける射出性が不安定になることも多く、特に、複数の染料を組み合せることにより、昇華性染料の種類と量が多くなるブラックインクでは、こうした吐出安定性やインクの保存安定性に問題があった。 The inkjet ink used in the sublimation transfer method is mainly a water-based ink, in which sublimable dyes selected from water-insoluble disperse dyes and oil-soluble dyes are dispersed and stabilized in fine particles in water using a dispersant. A water-soluble organic solvent is added as a humectant (anti-drying agent), a surfactant is used as a surface tension adjuster, and other additives (pH adjuster, preservative/antifungal agent, antifoaming agent, etc.) are added to this dye dispersion. The ink is made by optimizing the physical properties such as particle size, viscosity, surface tension, and pH using the ink (see Patent Document 1). In addition, in inkjet printing, it is important to be able to stably eject ink from the plate on which the print head nozzles are arranged, but with water-based ink, ejection problems can occur due to evaporation of water in the ink near the nozzle plate. It's easy to happen. The above-mentioned ejection troubles include, for example, when the ink composition adheres to and dries on the plate, it cannot be removed quickly by the printer's cleaning operation, resulting in ink ejection failure (curved flight, etc.) during printing. There are many things that can be mentioned. In order to solve these problems, for example, when expressing black using dyes having sublimation properties, black is usually expressed by combining a plurality of dyes. This is because a single dye alone is not sufficient as a black hue and often has a low density, so by combining multiple dyes, it is possible to express black well. However, when a fabric is dyed with a black ink that combines multiple sublimable dyes, the black color expressed on the fabric may change depending on the type of fabric when the fabric is irradiated with light with a different spectral distribution of the light source. In some cases, the hues appeared to be different colors. For example, under lighting with little long-wavelength light such as fluorescent lighting, good colors may be expressed, but under sunlight with a lot of long-wavelength light, the color may appear reddish, or vice versa. Even if the colors were good under fluorescent lighting, they sometimes appeared bluish under fluorescent lighting. As described above, the characteristics that affect the appearance of colors of objects due to the illumination light source are generally referred to as "color rendering properties," and there has been a demand for black ink that exhibits little change in hue due to the influence of this color rendering properties. Furthermore, inkjet inks are required to have good jetting properties, and if the dye is unstable or poorly dispersed in the ink, the jetting properties in the inkjet head often become unstable. However, black ink in which the types and amounts of sublimable dyes are increased by combining a plurality of dyes has problems in ejection stability and storage stability of the ink.
一方、昇華転写方式における疎水性繊維の捺染方法では、インクジェットプリンタにて昇華転写インクを中間記録媒体(専用の転写紙等)に付与(プリント)し、中間記録媒体のインク付与(プリント)面と被染色対象物(ポリエステル繊維等)を重ね合わせた物を、熱圧着ローラーや熱プレス機等による熱圧着方式によって昇華性染料を被染色対象物に転写させている。商業用印刷においては、インクジェット印刷はより高速化しておりインクジェット用インクにも高速化に対応したインクの設計が求められている。また、昇華転写インク用の中間記録媒体としては、シリカ等の無機微粒子でインク受容層が表面に形成されており、多量のインクを付与できるように比較的に坪量が大きいインクジェット用の専用紙が一般的に挙げられるが、近年ではより坪量の小さい転写紙やインク受容層が少ない転写紙が用いられており、少ないインク量で高い転写効率、高い染色濃度が強く求められている。それに加えて、昇華転写条件によって黒色の色相がぶれず、昇華速度が均一なブラックインクが求められている。特許文献2には、捺染用分散染料インクに用いるインクジェット用ブラックインクであって、グリコールエーテルを含む水溶性有機溶剤と、アセトンに溶解した溶液の紫外可視分光吸収において、ある特定の波長域に極大吸収波長を有する第1~4の分散染料を含有することを特長とするインクジェット用ブラックインクが記載されているが、ダイレクトプリント法における前処理したポリエステル繊維に直接付与するインクについては触れているが、昇華転写法で使用できる昇華性を有する染料に関わる技術検討まではされておらず、また、高濃度染色における均染性や染色性能については開示されていない。 On the other hand, in the sublimation transfer method for printing hydrophobic fibers, sublimation transfer ink is applied (printed) to an intermediate recording medium (such as a special transfer paper) using an inkjet printer, and the ink-applied (printed) surface of the intermediate recording medium and The objects to be dyed (polyester fibers, etc.) are stacked one on top of the other, and the sublimable dye is transferred onto the objects by a thermocompression method using a thermocompression roller, a heat press, or the like. In commercial printing, inkjet printing is becoming faster and there is a need for inkjet inks to be designed to accommodate higher speeds. In addition, as an intermediate recording medium for sublimation transfer ink, an ink-receiving layer is formed on the surface of inorganic fine particles such as silica, and special paper for inkjet printing has a relatively large basis weight so that a large amount of ink can be applied. However, in recent years, transfer papers with smaller basis weights and transfer papers with fewer ink-receiving layers have been used, and there is a strong demand for high transfer efficiency and high dye density with a small amount of ink. In addition, there is a need for a black ink that does not vary in black hue depending on sublimation transfer conditions and has a uniform sublimation speed. Patent Document 2 describes an inkjet black ink used as a disperse dye ink for textile printing, in which the ultraviolet-visible spectral absorption of a water-soluble organic solvent containing glycol ether and a solution dissolved in acetone has a maximum in a certain wavelength range. A black inkjet ink characterized by containing first to fourth disperse dyes having absorption wavelengths is described, but the ink directly applied to pretreated polyester fibers in a direct printing method is mentioned. , there has been no technical study related to dyes with sublimation properties that can be used in the sublimation transfer method, and there is no disclosure of level dyeing properties or dyeing performance in high-density dyeing.
昇華転写法に使用されているインクジェットインクは、主として水性インクが使用され、水不溶性である分散染料群及び油溶性染料群から選ばれる染料を、分散剤を用いて水中に微粒子分散安定化した染料分散液とし、これに、保湿剤(乾燥防止剤)として水溶性有機溶剤、表面張力調整剤として界面活性剤、その他添加剤(pH調整剤、防腐・防黴剤、消泡剤等)を用いて、粒度・粘度・表面張力・pH等の物理特性(物性)を最適化してインク化されている(特許文献1参照)。また、インクジェットプリントにおいて、プリントヘッドのノズルが配列されたプレートからインクを安定的に吐出できる事が重要であるが、水系インクにおいてはノズルプレート近傍でインク中の水分の蒸発によって引き起こされる吐出トラブルが起こり易い。上記吐出トラブルとしては、例えば、プレート上でインク組成物が付着乾燥した場合に、プリンタのクリーニング動作で速やかに除去する事ができずに、印刷中にインクの吐出不良(飛行曲がり等)を引き起こすことなどが挙げられる。インクジェットインクには、良好な射出性も求められ、染料がインク中で不安定であったり、分散が不十分であったりすると、インクジェットヘッドにおける射出性が不安定になるという問題がある。 The inkjet ink used in the sublimation transfer method is mainly a water-based ink, in which a dye selected from the water-insoluble disperse dye group and the oil-soluble dye group is stabilized by dispersing fine particles in water using a dispersant. A dispersion liquid is prepared, and a water-soluble organic solvent is used as a humectant (anti-drying agent), a surfactant is used as a surface tension adjuster, and other additives (pH adjuster, preservative/anti-mold agent, antifoaming agent, etc.) are used. Ink has been made by optimizing physical properties such as particle size, viscosity, surface tension, and pH (see Patent Document 1). In addition, in inkjet printing, it is important to be able to stably eject ink from the plate on which the print head nozzles are arranged, but with water-based ink, ejection problems can occur due to evaporation of water in the ink near the nozzle plate. It's easy to happen. The above-mentioned ejection troubles include, for example, when the ink composition adheres to and dries on the plate, it cannot be removed quickly by the printer's cleaning operation, resulting in ink ejection failure (curved flight, etc.) during printing. There are many things that can be mentioned. Inkjet inks are also required to have good jetting properties, and if the dye is unstable or poorly dispersed in the ink, there is a problem that the jetting properties in the inkjet head will become unstable.
本発明は、インクジェット捺染を用いた昇華転写染色において、演色性に優れた染色物を作製でき、昇華転写効率が高く、高濃度の染色物を得ることができる高品位な染色物を得ることができ、さらに保存安定性が良好なインクジェット捺染インク用分散液を提供することを目的とするものである。 The present invention makes it possible to produce dyed products with excellent color rendering properties in sublimation transfer dyeing using inkjet printing, and to obtain high-quality dyed products with high sublimation transfer efficiency and high density dyeing. It is an object of the present invention to provide an inkjet textile printing ink dispersion liquid which can be used as an inkjet textile ink and has good storage stability.
本発明者らは上記したような課題を解決すべく鋭意研究を重ねた結果、(A)下記式(1)で表される化合物、(B)C.I.Disperse Blue 360、(C)分散剤、を含み、(A)と(B)の総含有量を100とした場合、(B)の含有量が10以上90以下であり、(C)分散剤がポリオキシエチレンアリールフェニルエーテル系分散剤、ポリオキシエチレンアリールフェニルエーテルサルフェート系分散剤、からなる群から選択されるいずれかを少なくとも含む着色分散液が、上記課題を解決するものであることを見出し、本発明を完成させたものである。 The present inventors have conducted extensive research to solve the above-mentioned problems, and have found that (A) a compound represented by the following formula (1), (B) C.I. I. Disperse Blue 360 contains (C) a dispersant, and when the total content of (A) and (B) is 100, the content of (B) is 10 or more and 90 or less, and (C) the dispersant is It has been discovered that a colored dispersion solution containing at least one selected from the group consisting of a polyoxyethylene arylphenyl ether dispersant and a polyoxyethylene arylphenyl ether sulfate dispersant solves the above problems, This completes the present invention.
即ち本発明は、以下の1)~9)に関する。
1)
(A)下記式(1)で表される化合物、(B)C.I.Disperse Blue 360、(C)分散剤、を含み、(A)と(B)の総含有量を100とした場合、(B)の含有量が10以上90以下であり、(C)分散剤がポリオキシエチレンアリールフェニルエーテル系分散剤、ポリオキシエチレンアリールフェニルエーテルサルフェート系分散剤、からなる群から選択されるいずれかを少なくとも含む着色分散液。
That is, the present invention relates to the following 1) to 9).
1)
(A) a compound represented by the following formula (1), (B) C.I. I. Disperse Blue 360 contains (C) a dispersant, and when the total content of (A) and (B) is 100, the content of (B) is 10 or more and 90 or less, and (C) the dispersant is A colored dispersion containing at least one selected from the group consisting of a polyoxyethylene arylphenyl ether dispersant and a polyoxyethylene arylphenyl ether sulfate dispersant.
(式(1)中、R1は水素原子またはニトロ基を示す。R2、R3はそれぞれ独立に、C1~C4アルコキシ基またはフェニル基で置換されても良い、C1~C4アルキル基を示す。R4はハロゲン原子を示す。また、R2とR3は互いに連結して環を形成しても良い。)
2)
上記式(1)におけるR4が塩素原子または臭素原子である、1)に記載の着色分散液。
3)
上記式(1)におけるR1が水素原子、R2、R3がそれぞれ独立に、C1~C4アルコキシ基で置換されても良いC1~C4アルキル基、R4が塩素原子である、1)に記載の着色分散液。
4)
イエロー染料を1種と、アセトンに溶解した溶液の紫外可視分光吸収において、620nm以上700nm未満の波長域に極大吸収波長を有するブルー染料を1種と、アセトンに溶解した溶液の紫外可視分光吸収において、550nm以上620nm未満の波長域に極大吸収波長を有するブルー染料を1種と、をさらに含む1)~3)のいずれか一項に記載の着色分散液。
5)
さらに水溶性有機溶剤を含む1)~4)のいずれか一項に記載の着色分散液。
6)
1)~5)のいずれか一項に記載の着色分散液が付着した記録メディア。
7)
上記記録メディアが繊維である、6)に記載の記録メディア。
8)
上記繊維が、疎水性繊維である7)に記載の記録メディア。
9)
上記疎水性繊維が、ポリエステル又はポリエステルを含有する混紡繊維である、8)に記載の記録メディア。
(In formula (1), R 1 represents a hydrogen atom or a nitro group. R 2 and R 3 each independently represent a C1 to C4 alkyl group which may be substituted with a C1 to C4 alkoxy group or a phenyl group. (R 4 represents a halogen atom. R 2 and R 3 may be linked to each other to form a ring.)
2)
The colored dispersion according to 1), wherein R 4 in the above formula (1) is a chlorine atom or a bromine atom.
3)
In 1), R 1 in the above formula (1) is a hydrogen atom, R 2 and R 3 are each independently a C1 to C4 alkyl group which may be substituted with a C1 to C4 alkoxy group, and R 4 is a chlorine atom. Colored dispersions as described.
4)
In the ultraviolet-visible spectral absorption of a solution dissolved in acetone, one type of yellow dye has a maximum absorption wavelength in the wavelength range of 620 nm or more and less than 700 nm, and in the ultraviolet-visible spectral absorption of a solution dissolved in acetone. , and one kind of blue dye having a maximum absorption wavelength in a wavelength range of 550 nm or more and less than 620 nm, the colored dispersion according to any one of 1) to 3).
5)
The colored dispersion according to any one of 1) to 4), further comprising a water-soluble organic solvent.
6)
A recording medium to which the colored dispersion according to any one of 1) to 5) is attached.
7)
The recording medium according to 6), wherein the recording medium is a fiber.
8)
7) The recording medium according to 7), wherein the fiber is a hydrophobic fiber.
9)
8) The recording medium according to 8), wherein the hydrophobic fiber is polyester or a blended fiber containing polyester.
本発明により、保存安定性に優れ、インクジェット捺染を用いた昇華転写染色において、演色性の影響による色相の変化が少ない染色物を作製でき、昇華転写効率が高く、高濃度の染色物を得ることができる高品位な黒色の染色物を得ることができる着色分散液、およびインクが得られる。 ADVANTAGE OF THE INVENTION According to the present invention, it is possible to produce a dyed product that has excellent storage stability, has little change in hue due to the influence of color rendering properties in sublimation transfer dyeing using inkjet printing, has high sublimation transfer efficiency, and obtains a dyed product with high density. A colored dispersion and an ink that can produce high-quality black dyed products are obtained.
以下、本発明について詳細に説明する。本明細書においては実施例等を含めて、特に断りの無い限り「部」及び「%」は、いずれも質量基準である。また、含有量は、含有質量を表わす。また、本願明細書において、(A)と(B)の量関係を示す単位は%を表わす。また、本明細書において「C.I.」とは、「カラーインデックス」を意味する。 The present invention will be explained in detail below. In this specification, including Examples, unless otherwise specified, all "parts" and "%" are based on mass. Moreover, the content represents the contained mass. Further, in the present specification, the unit indicating the quantitative relationship between (A) and (B) is %. Moreover, in this specification, "C.I." means "color index."
本発明に係る着色分散液は、(A)下記式(1)で表される化合物、(B)C.I.Disperse Blue 360、(C)分散剤、を含み、(A)と(B)の総含有量を100とした場合、(B)の含有量が10以上90以下であり、(C)分散剤がポリオキシエチレンアリールフェニルエーテル系分散剤、ポリオキシエチレンアリールフェニルエーテルサルフェート系分散剤、からなる群から選択されるいずれかを少なくとも含む着色分散液である。 The colored dispersion according to the present invention comprises (A) a compound represented by the following formula (1), (B) C.I. I. Disperse Blue 360 contains (C) a dispersant, and when the total content of (A) and (B) is 100, the content of (B) is 10 or more and 90 or less, and (C) the dispersant is A colored dispersion containing at least one selected from the group consisting of a polyoxyethylene arylphenyl ether dispersant and a polyoxyethylene arylphenyl ether sulfate dispersant.
式(1)中、R1は水素原子またはニトロ基を示す。R2、R3はそれぞれ独立に、C1~C4アルコキシ基またはフェニル基で置換されても良い、C1~C4アルキル基を示す。R4はハロゲン原子を示す。また、R2とR3は互いに連結して環を形成しても良い。 In formula (1), R 1 represents a hydrogen atom or a nitro group. R 2 and R 3 each independently represent a C1-C4 alkyl group which may be substituted with a C1-C4 alkoxy group or a phenyl group. R 4 represents a halogen atom. Further, R 2 and R 3 may be connected to each other to form a ring.
上記C1~C4アルコキシ基またはフェニル基で置換されても良い、C1~C4アルキル基としては、C1~C4アルキル基、C1~C4アルコキシ基で置換されたC1~C4アルキル基、フェニル基で置換されたC1~C4アルキル基が挙げられる。 The above C1-C4 alkyl group which may be substituted with a C1-C4 alkoxy group or a phenyl group includes a C1-C4 alkyl group, a C1-C4 alkyl group substituted with a C1-C4 alkoxy group, and a C1-C4 alkyl group substituted with a phenyl group. and C1-C4 alkyl groups.
上記C1~C4アルキル基としては、例えば、メチル基、エチル基、n-プロピル基、n-ブチル基等の直鎖アルキル基、iso-プロピル基、sec-ブチル基、tert-ブチル基等の分鎖アルキル基、シクロブチル基等の環状アルキル基が挙げられる。 Examples of the above C1 to C4 alkyl groups include linear alkyl groups such as methyl group, ethyl group, n-propyl group, and n-butyl group, iso-propyl group, sec-butyl group, and tert-butyl group. Examples include cyclic alkyl groups such as chain alkyl groups and cyclobutyl groups.
上記C1~C4アルコキシ基で置換されたC1~C4アルキル基としては、例えば、メトキシメチル基、メトキシエチル基、メトキシプロピル基、メトキシブチル基、エトキシメチル基、エトキシエチル基、エトキシプロピル基、エトキシブチル基、ブトキシブチル基等が挙げられる。 Examples of the C1 to C4 alkyl group substituted with the C1 to C4 alkoxy group include methoxymethyl group, methoxyethyl group, methoxypropyl group, methoxybutyl group, ethoxymethyl group, ethoxyethyl group, ethoxypropyl group, and ethoxybutyl group. group, butoxybutyl group, and the like.
上記フェニル基で置換されたC1~C4アルキル基としては、例えば、ベンジル基、フェニルエチル基、フェニルプロピル基等が挙げられる。 Examples of the C1-C4 alkyl group substituted with the phenyl group include a benzyl group, a phenylethyl group, a phenylpropyl group, and the like.
上記ハロゲン原子としては、例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられ、塩素原子または臭素原子であることが好ましく、塩素原子であることがさらに好ましい。 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc., preferably a chlorine atom or a bromine atom, and more preferably a chlorine atom.
上記式(1)におけるR2とR3は互いに連結して環を形成しても良い。R2とR3は互いに連結して形成する環としては、例えば、ピペリジン環、ピペラジン環、モルホリン環等が挙げられ、ピペリジン環を形成することが好ましい。 R 2 and R 3 in the above formula (1) may be connected to each other to form a ring. Examples of the ring formed by connecting R 2 and R 3 to each other include a piperidine ring, a piperazine ring, a morpholine ring, etc., and it is preferable that they form a piperidine ring.
上記式(1)において、R1が水素原子、R2、R3がそれぞれ独立にC1~C4アルコキシ基で置換されても良いC1~C4アルキル基、R4が塩素原子の組合せが好ましく、R1が水素原子、R2、R3がそれぞれ独立にメトキシ基で置換されても良いエチル基、R4が塩素原子の組合せがさらに好ましく、R1が水素原子、R2、R3の両方がメトキシエチル基、R4が塩素原子の組合せ、R1が水素原子、R2、R3がそれぞれエチル基、R4が塩素原子の組合せ、R1が水素原子、R2、R3のいずれか一方がメトキシエチル基であり他方がエチル基、R4が塩素原子の組合せ、が極めて好ましい。 In the above formula (1), it is preferable that R 1 is a hydrogen atom, R 2 and R 3 are each independently a C1 to C4 alkyl group which may be substituted with a C1 to C4 alkoxy group, and R 4 is a chlorine atom; A more preferred combination is that 1 is a hydrogen atom, R 2 and R 3 are each independently an ethyl group which may be substituted with a methoxy group, and R 4 is a chlorine atom, R 1 is a hydrogen atom, and both R 2 and R 3 are A combination of a methoxyethyl group, R 4 is a chlorine atom, R 1 is a hydrogen atom, R 2 and R 3 are each an ethyl group, and R 4 is a chlorine atom, R 1 is a hydrogen atom, either R 2 or R 3 A combination in which one is a methoxyethyl group, the other is an ethyl group, and R 4 is a chlorine atom is extremely preferred.
また、上記以外として、R1が水素原子、R2、R3が互いに連結してモルホリン環を形成、R4が塩素原子の組合せ、R1が水素原子、R2、R3が互いに連結してピペリジン環を形成、R4が塩素原子の組合せ、R1が水素原子、R2、R3のいずれか一方がiso-プロピル基であり他方がエチル基、R4が塩素原子の組合せ、R1が水素原子、R2、R3がいずれもエチル基、R4が臭素原子の組合せ、R1が水素原子、R2、R3のいずれか一方がベンジル基であり他方がエチル基、R4が塩素原子の組合せ、であることも好ましい。 In addition to the above, R 1 is a hydrogen atom, R 2 and R 3 are connected to each other to form a morpholine ring, R 4 is a combination of chlorine atoms, R 1 is a hydrogen atom, and R 2 and R 3 are connected to each other to form a morpholine ring. to form a piperidine ring, R 4 is a combination of chlorine atoms, R 1 is a hydrogen atom, one of R 2 and R 3 is an iso-propyl group and the other is an ethyl group, R 4 is a chlorine atom, R 1 is a hydrogen atom, R 2 and R 3 are both ethyl groups, R 4 is a bromine atom, R 1 is a hydrogen atom, one of R 2 and R 3 is a benzyl group, and the other is an ethyl group, R It is also preferable that 4 is a combination of chlorine atoms.
上記式(1)で表される化合物は、例えば、下記式(2)で表される化合物を常法によりジアゾ化し、得られたジアゾ化合物と下記式(3)で表される化合物とを常法によりカップリング反応させることで得ることができる。下記式(2)及び(3)における、R1~R4は上記式(1)におけるものと同じである。 The compound represented by the above formula (1) can be obtained, for example, by diazotizing the compound represented by the following formula (2) using a conventional method, and then combining the obtained diazo compound with the compound represented by the following formula (3). It can be obtained by a coupling reaction using a method. In the following formulas (2) and (3), R 1 to R 4 are the same as in the above formula (1).
上記のようにして得られた上記式(1)で表される化合物は、必要に応じて、例えば、酸析、塩析、懸濁精製、及び晶析等公知の方法により精製することができる。 The compound represented by the above formula (1) obtained as above can be purified by known methods such as acid precipitation, salting out, suspension purification, and crystallization, if necessary. .
上記式(1)で表される化合物を含む上記着色分散液中、上記式(1)で表される化合物は、1種単独、あるいは2種以上を組合せて用いることが可能であり、2種以上を組合せて用いる場合、それらの質量比は任意に設定可能である。 In the colored dispersion containing the compound represented by the above formula (1), the compound represented by the above formula (1) can be used alone or in combination of two or more kinds, and two kinds of the compound represented by the above formula (1) can be used. When using a combination of the above, their mass ratio can be set arbitrarily.
分散染料は、その極大吸収波長から、ブルー系染料、シアン系染料、レッド系染料、イエロー系染料、オレンジ系染料等に分類される。ブラックの色調を得るためには、これら染料を混合して使用することが好ましい。極大吸収波長が異なる分散染料を組み合わせることで、短波長側から長波長側までのすべての領域において分光吸収の強度の分布が少なくなり、ブラックの色相を有した演色性の影響が少ないインクを作ることができる。上記着色分散液は、上記式(1)で表される化合物及びC.I.Disperse Blue 360に加え、イエロー系染料、ブルー系染料を含むことにより、良好なブラックの色相を有する着色分散液とすることができる。特に、上記式(1)で表される化合物及びC.I.Disperse Blue 360に加え、イエロー系染料を1種と、アセトンに溶解した溶液の紫外可視分光吸収において、620nm以上700nm未満の波長域に極大吸収波長を有するブルー系染料を1種と、を含むことが好ましい。 Disperse dyes are classified into blue dyes, cyan dyes, red dyes, yellow dyes, orange dyes, etc. based on their maximum absorption wavelengths. In order to obtain a black tone, it is preferable to use a mixture of these dyes. By combining disperse dyes with different maximum absorption wavelengths, the distribution of spectral absorption intensity is reduced in all regions from the short wavelength side to the long wavelength side, creating an ink with a black hue that is less affected by color rendering properties. be able to. The colored dispersion liquid contains a compound represented by the above formula (1) and C.I. I. By containing a yellow dye and a blue dye in addition to Disperse Blue 360, a colored dispersion having a good black hue can be obtained. In particular, the compound represented by the above formula (1) and C.I. I. In addition to Disperse Blue 360, it contains one type of yellow dye and one type of blue dye that has a maximum absorption wavelength in the wavelength range of 620 nm or more and less than 700 nm in the ultraviolet-visible spectral absorption of a solution dissolved in acetone. is preferred.
[イエロー系染料について]
上記イエロー系染料としては、一般的にイエロー系の色相を有する染料であれば特に限定はないが、水不溶性イエロー系染料であることが好ましく、水不溶性イエロー系染料のなかでも、分散染料系イエロー系染料または油溶性染料系イエロー系染料であることがさらに好ましく、C.I.Disperse Yellow系染料、C.I.Solvent Yellow系染料であることがより好ましい。C.I.Disperse Yellow系染料としては、例えば、C.I.Disperse Yellow 3、7、8、23、39、51、54、60、64、71、79、82、86等が挙げられる。C.I.Solvent Yellow系染料としては、例えば、C.I.Solvent Yellow 114、163等が挙げられる。これら染料は単独あるいは複数を組み合わせて用いることが可能である。上記イエロー系染料としては、C.I.Disperse Yellow 7、54、C.I.Solvent Yellow 114を用いることが好ましく、C.I.Disperse Yellow 54を用いることが特に好ましい。
[About yellow dye]
The above yellow dye is not particularly limited as long as it is a dye that generally has a yellow hue, but water-insoluble yellow dyes are preferred, and among water-insoluble yellow dyes, disperse dye yellow dyes are preferred. It is more preferable to use a C.I.-based dye or an oil-soluble dye-based yellow dye. I. Disperse Yellow dye, C.I. I. More preferably, it is a Solvent Yellow dye. C. I. Examples of the Disperse Yellow dye include C.I. I. Disperse Yellow 3, 7, 8, 23, 39, 51, 54, 60, 64, 71, 79, 82, 86 and the like. C. I. Examples of Solvent Yellow dyes include C.I. I. Examples include Solvent Yellow 114 and 163. These dyes can be used alone or in combination. As the yellow dye, C.I. I. Disperse Yellow 7, 54, C. I. It is preferable to use Solvent Yellow 114, C.I. I. Particular preference is given to using Disperse Yellow 54.
[ブルー系染料について]
上記ブルー系染料としては、一般的にブルー系の色相を有する染料であれば特に限定はないが、水不溶性ブルー系染料であることが好ましく、水不溶性ブルー系染料のなかでも、分散染料系ブルー系染料または油溶性染料系ブルー系染料であることがさらに好ましく、C.I.Disperse Blue系染料、C.I.Solvent Blue系染料であることがより好ましい。C.I.Disperse Blue系染料としては、例えば、C.I.Disperse Blue 3、5、19、26、26:1、35、55、56、58、60、64、64:1、72、72:1、81、81:1、91、95、108、131、141、145、334、359、336等が挙げられる。C.I.Solvent Blue系染料としては、例えば、C.I.Solvent Blue 3、36、63、83、105、111等が挙げられる。これら染料は単独あるいは複数を組み合わせて用いることが可能である。上記ブルー系染料としては、C.I.Disperse Blue 60、72、334、359であることが好ましく、C.I.Disperse Blue 359であることがさらに好ましい。該C.I.Disperse Blue 359は、上記、アセトンに溶解した溶液の紫外可視分光吸収において、620nm以上700nm未満の波長域に極大吸収波長を有するブルー系染料である。
[About blue dye]
The above-mentioned blue dye is not particularly limited as long as it is a dye that generally has a blue hue, but water-insoluble blue dyes are preferred, and among water-insoluble blue dyes, disperse dye blue It is more preferable to use a C.I.-based dye or an oil-soluble blue dye. I. Disperse Blue dye, C.I. I. More preferably, it is a Solvent Blue dye. C. I. Examples of the Disperse Blue dye include C.I. I. Disperse Blue 3, 5, 19, 26, 26:1, 35, 55, 56, 58, 60, 64, 64:1, 72, 72:1, 81, 81:1, 91, 95, 108, 131, 141, 145, 334, 359, 336 and the like. C. I. Examples of Solvent Blue dyes include C.I. I. Examples include Solvent Blue 3, 36, 63, 83, 105, and 111. These dyes can be used alone or in combination. The blue dye mentioned above is C.I. I. Disperse Blue 60, 72, 334, 359 is preferred; I. More preferably, it is Disperse Blue 359. The C. I. Disperse Blue 359 is a blue dye having a maximum absorption wavelength in a wavelength range of 620 nm or more and less than 700 nm in the ultraviolet-visible spectral absorption of a solution dissolved in acetone.
上記着色分散液における、上記式(1)で表される化合物とC.I.Disperse Blue 360と上記イエロー系染料と上記ブルー系染料、の合計の含有割合は、任意で設定することが可能であるが、着色分散液総質量に対し、いずれも質量基準(質量%)で通常1~20%、好ましくは2~15%、より好ましくは3~10%である。 In the colored dispersion, the compound represented by the above formula (1) and the C.I. I. The total content ratio of Disperse Blue 360, the above yellow dye, and the above blue dye can be set arbitrarily, but it is usually set on a mass basis (mass%) with respect to the total mass of the colored dispersion. It is 1 to 20%, preferably 2 to 15%, more preferably 3 to 10%.
[着色分散液に含んでも良いその他染料について]
上記着色分散液は、上記式(1)で表される化合物、C.I.Disperse Blue 360、上記イエロー系染料、上記ブルー系染料以外に、その他染料を含んでいても良い。該その他染料としては、例えば、乾熱処理に対する染色堅ろう度試験方法[JIS L 0879:2005](2010年 確認、平成17年1月20日 改定、 財団法人日本規格協会 発行)、「ISO 105-P01,Textiles-Tests for colour fastness-PartP01:Colour fastness to dry heat(excluding pressing)」における、感熱処理試験(C法)汚染(ポリエステル)の試験結果が、好ましくは3-4級以下、より好ましくは3級以下、の染料が挙げられる。そのような公知の染料のうち、C.I.番号を有する染料としては、例えば、以下の染料が挙げられる。
[About other dyes that may be included in the colored dispersion]
The colored dispersion liquid contains a compound represented by the above formula (1), C.I. I. In addition to Disperse Blue 360, the above-mentioned yellow dye, and the above-mentioned blue dye, other dyes may be included. Examples of such other dyes include, for example, dye fastness test method for dry heat treatment [JIS L 0879:2005] (confirmed in 2010, revised on January 20, 2005, published by Japan Standards Association), "ISO 105-P01" , Textiles-Tests for color fastness-PartP01: Color fastness to dry heat (excluding pressing)", the test result of heat-sensitive treatment test (Method C) contamination (polyester) is preferably grade 3-4 or lower, more preferably 3 Examples include dyes of grade or lower. Among such known dyes, C.I. I. Examples of dyes with numbers include the following dyes.
上記その他染料における、その他のイエロー系染料としては、例えば、C.I.Disperse Yellow系染料及びC.I.Solvent Yellow系染料で、上記イエロー系染料として例示したもの以外のものが挙げられる。これら染料は単独あるいは複数を組み合わせて用いることができる。 Examples of other yellow dyes in the above-mentioned other dyes include C.I. I. Disperse Yellow dye and C.I. I. Solvent yellow dyes other than those exemplified above as yellow dyes may be used. These dyes can be used alone or in combination.
上記その他染料における、その他のブルー系染料としては、例えば、C.I.Disperse Blue系染料及びC.I.Solvent Blue系染料で、上記ブルー系染料として例示したもの以外のものが挙げられる。これら染料は単独あるいは複数を組み合わせて用いることができる。 Among the other blue dyes mentioned above, examples of other blue dyes include C.I. I. Disperse Blue dye and C.I. I. Examples of Solvent Blue dyes include those other than those exemplified as the blue dyes above. These dyes can be used alone or in combination.
上記その他染料における、その他のオレンジ系染料としては、例えば、C.I.Disperse Orange 1、1:1、5、7、11、13、20、23、25、25:1、29、33、56、73、76、113、114、123、147;C.I.Solvent Orange 60、67等が挙げられる。これら染料は単独あるいは複数を組み合わせて用いることができる。 Examples of other orange dyes in the above-mentioned other dyes include C.I. I. Disperse Orange 1, 1:1, 5, 7, 11, 13, 20, 23, 25, 25:1, 29, 33, 56, 73, 76, 113, 114, 123, 147; C. I. Examples include Solvent Orange 60 and 67. These dyes can be used alone or in combination.
上記その他染料における、その他のブラウン系染料としては、例えば、C.I.Disperse Brown 1、3、22、26、27;等が挙げられる。これら染料は単独あるいは複数を組み合わせて用いることができる。 Other brown dyes among the above-mentioned other dyes include, for example, C.I. I. Disperse Brown 1, 3, 22, 26, 27; and the like. These dyes can be used alone or in combination.
上記その他染料における、その他のレッド系染料としては、例えば、C.I.Disperse Red 4、11、50、53、55、55:1、59、60、65、70、75、92、93、146、158、190、190:1、207、239、240、364;C.I.Solvent Red 146;C.I.Vat Red 41;等が挙げられる。これら染料は単独あるいは複数を組み合わせて用いることができる。 Among the other red dyes mentioned above, examples of other red dyes include C.I. I. Disperse Red 4, 11, 50, 53, 55, 55:1, 59, 60, 65, 70, 75, 92, 93, 146, 158, 190, 190:1, 207, 239, 240, 364; I. Solvent Red 146;C. I. Vat Red 41; and the like. These dyes can be used alone or in combination.
上記その他染料における、その他のバイオレット系染料としては、例えば、C.I.Disperse Violet 8、11、17、23、26、27、28、29、36、57、63;等が挙げられる。これら染料は単独あるいは複数を組み合わせて用いることができる。 Other violet dyes among the above other dyes include, for example, C.I. I. Disperse Violet 8, 11, 17, 23, 26, 27, 28, 29, 36, 57, 63; and the like. These dyes can be used alone or in combination.
上記各染料は、粉末状あるいは塊状の乾燥色材でも、ウエットケーキやスラリーでも良く、色材合成中や合成後に色材粒子の凝集を抑える目的として、界面活性剤等の分散剤が少量含有されたものであっても良い。市販の染料には、工業染色用、樹脂着色用、インキ用、トナー用、インクジェット用などのグレードがあり、製造方法、純度、粒径等がそれぞれ異なる。粉砕後の凝集性を抑えるには色材としてはより粒子の小さいものが好ましく、また分散安定性及びインクの吐出精度への影響からできるだけ不純物などの少ないものが好ましい。染料においてはブルー系染料を主体にイエロー系染料、オレンジ系染料及びレッド系染料を配合することでブラック用の色材として用いることができる。また色調調整の範囲内で他の水不溶性色材を少量含んでも良い。 Each of the above dyes may be a dry coloring material in the form of a powder or block, or a wet cake or slurry, and a small amount of a dispersant such as a surfactant may be contained in order to suppress the agglomeration of coloring material particles during or after coloring material synthesis. It may be something that Commercially available dyes include grades for industrial dyeing, resin coloring, ink, toner, and inkjet use, and each grade differs in manufacturing method, purity, particle size, etc. In order to suppress agglomeration after pulverization, it is preferable that the coloring material has smaller particles, and in view of the influence on dispersion stability and ink ejection accuracy, it is preferable that it contains as few impurities as possible. As for the dye, it can be used as a coloring material for black by blending a yellow dye, an orange dye, and a red dye mainly with a blue dye. Further, a small amount of other water-insoluble coloring materials may be included within the range of color tone adjustment.
上記着色分散液は、ポリオキシエチレンアリールフェニルエーテル系分散剤、ポリオキシエチレンアリールフェニルエーテルサルフェート系分散剤、からなる群から選択されるいずれか分散剤を含む。 The colored dispersion liquid contains any dispersant selected from the group consisting of a polyoxyethylene arylphenyl ether type dispersant and a polyoxyethylene arylphenyl ether sulfate type dispersant.
上記、ポリオキシエチレンアリールフェニルエーテル系分散剤、ポリオキシエチレンアリールフェニルエーテルサルフェート系分散剤としては、具体的には、ポリオキシエチレンモノスチリルフェニルエーテル、ポリオキシエチレンジスチリルフェニルエーテル、ポリオキシエチレントリスチリルフェニルエーテル、ポリオキシエチレンテトラスチリルフェニルエーテルなどのスチリルフェノール化合物、ポリオキシエチレンモノベンジルフェニルエーテル、ポリオキシエチレンジベンジルフェニルエーテル、ポリオキシエチレントリベンジルフェニルエーテルなどのベンジルフェノール化合物、ポリオキシエチレンクミルフェニルエーテルなどのクミルフェノール化合物、ポリオキシエチレンナフチルフェニルエーテル、ポリオキシエチレンビフェニルエーテル、ポリオキシエチレンフェノキシフェニルエーテル等が例示される。これらは、単独あるいは複数を組合せて使用できる。好ましくは、ポリオキシエチレンジスチリルフェニルエーテル、ポリオキシエチレントリスチリルフェニルエーテル、ポリオキシエチレンジベンジルフェニルエーテル、ポリオキシエチレントリベンジルフェニルエーテル、ポリオキシエチレンクミルフェニルエーテルである。ここで、ポリオキシエチレン基の繰り返し単位数bは、1~30の整数であり、好ましくは15~30の整数である。bが1以上の整数であると、水性溶媒や他の添加剤との相溶性に優れることとなり、30以下の整数であると、粘度が高くなりすぎないため好適である。これらはアリールフェノール化合物とも呼称される。 Specifically, the polyoxyethylene arylphenyl ether dispersants and polyoxyethylene arylphenyl ether sulfate dispersants mentioned above include polyoxyethylene monostyrylphenyl ether, polyoxyethylene distyrylphenyl ether, polyoxyethylene tristyrylphenyl ether, Styryl phenol compounds such as styryl phenyl ether and polyoxyethylene tetrastyrylphenyl ether, benzyl phenol compounds such as polyoxyethylene monobenzylphenyl ether, polyoxyethylene dibenzylphenyl ether, and polyoxyethylene tribenzylphenyl ether; Examples include cumylphenol compounds such as mylphenyl ether, polyoxyethylene naphthylphenyl ether, polyoxyethylene biphenyl ether, and polyoxyethylene phenoxyphenyl ether. These can be used alone or in combination. Preferred are polyoxyethylene distyrylphenyl ether, polyoxyethylene tristyrylphenyl ether, polyoxyethylene dibenzylphenyl ether, polyoxyethylene tribenzylphenyl ether, and polyoxyethylene cumylphenyl ether. Here, the number b of repeating units of the polyoxyethylene group is an integer of 1 to 30, preferably an integer of 15 to 30. When b is an integer of 1 or more, it has excellent compatibility with the aqueous solvent and other additives, and when it is an integer of 30 or less, the viscosity does not become too high, which is preferable. These are also called arylphenol compounds.
このようなアリールフェノール化合物としては、下記に記載されるものが例示される。スチリルフェノール化合物としては、例えば、第一工業製薬(株)製 ノイゲン EAシリーズ、東邦化学工業(株)製 TS-2000、TS-2600、SM-174N等の市販品を使用することができる。また、ベンジルフェノール化合物としては、例えば、花王(株)製 エマルゲン B-66等の市販品を使用でき、クミルフェノール化合物としては、例えば、日本乳化剤(株)製 ニューコール CMP系等の市販品を使用することができる。
ポリオキシエチレンアリールフェニルエーテル系分散剤としては、例えば、パイオニンD-6112、パイオニンD-6115、パイオニンD-6120、パイオニンD-6131、パイオニンD-6512、タケサーフD-6413、DTD-51、パイオニンD-6112、パイオニンD-6320(いずれも竹本油脂社製)、TS-1500、TS-2000、TS-2600、SM-174N(いずれも東邦化学社製)、エマルゲンA60、エマルゲンA90、エマルゲンA500(花王)等が挙げられ、これらは単独あるいは複数を組合せて用いることが可能である。ポリオキシエチレンアリールフェニルエーテルサルフェート系分散剤としては、例えば、SM-57、SM-130、SM-210(いずれも東邦化学社製)が挙げられ、これらは単独あるいは複数を組合せて用いることが可能である。
Examples of such arylphenol compounds include those described below. As the styrylphenol compound, commercially available products such as Noigen EA series manufactured by Daiichi Kogyo Seiyaku Co., Ltd. and TS-2000, TS-2600, and SM-174N manufactured by Toho Chemical Industry Co., Ltd. can be used. Further, as the benzylphenol compound, for example, a commercial product such as Emulgen B-66 manufactured by Kao Corporation can be used, and as the cumylphenol compound, for example, a commercial product such as Nucor CMP series manufactured by Nippon Nyukazai Co., Ltd. can be used. can be used.
Examples of polyoxyethylene arylphenyl ether dispersants include Pionin D-6112, Pionin D-6115, Pionin D-6120, Pionin D-6131, Pionin D-6512, Takesurf D-6413, DTD-51, and Pionin D. -6112, Pionin D-6320 (all manufactured by Takemoto Yushi Co., Ltd.), TS-1500, TS-2000, TS-2600, SM-174N (all manufactured by Toho Chemical Co., Ltd.), Emulgen A60, Emulgen A90, Emulgen A500 (Kao ), and these can be used alone or in combination. Examples of polyoxyethylene arylphenyl ether sulfate-based dispersants include SM-57, SM-130, and SM-210 (all manufactured by Toho Chemical Co., Ltd.), and these can be used alone or in combination. It is.
上記着色分散液は、上記ポリオキシエチレンアリールフェニルエーテル系分散剤及び上記ポリオキシエチレンアリールフェニルエーテルサルフェート系分散剤以外に、その他の分散剤をさらに含むことが可能である。 The colored dispersion liquid may further contain other dispersants in addition to the polyoxyethylene arylphenyl ether dispersant and the polyoxyethylene arylphenyl ether sulfate dispersant.
上記その他の分散剤としては、例えば、スチレン-(メタ)アクリル共重合体あるいは芳香族スルホン酸のホルマリン縮合物又はその塩を用いることが可能である。上記スチレン-(メタ)アクリル共重合体は、スチレン系モノマーと(メタ)アクリル系モノマーの共重合体である。なお本明細書において、「(メタ)アクリル」とは、「アクリル」及び/又は「メタクリル」の意味を表わす。これら共重合体の具体例としては、(α-メチル)スチレン-アクリル酸共重合体、(α-メチル)スチレン-アクリル酸-アクリル酸エステル共重合体、(α-メチル)スチレン-メタクリル酸共重合体、(α-メチル)スチレン-メタクリル酸-アクリル酸エステル共重合体、(α-メチル)スチレン-(無水)マレイン酸共重合体、アクリル酸エステル-(無水)マレイン酸共重合体、(α-メチル)スチレン-アクリル酸エステル-(無水)マレイン酸共重合体、アクリル酸エステル-アリルスルホン酸エステル共重合体、アクリル酸エステル-スチレンスルホン酸共重合体、(α-メチル)スチレン-メタクリルスルホン酸共重合体、ポリエステル-アクリル酸共重合体、ポリエステル-アクリル酸-アクリル酸エステル共重合体、ポリエステル-メタクリル酸共重合体、ポリエステル-メタクリル酸-アクリル酸共重合体エステル;等が挙げられる。これらの中では芳香族炭化水素基を含む化合物がスチレンのものが好ましい。なお、(α-メチル)スチレンとは、本明細書においてα-メチルスチレン、及びスチレンを含む意味として用いる。上記着色分散液においては、上記その他の分散剤が、スチレン-(メタ)アクリル共重合体、芳香族スルホン酸のホルマリン縮合物又はその塩、からなる群から選択される分散剤を少なくとも1種類を含むものが好ましい。上記着色分散液中、その他の分散剤の含有率は、通常1~36%、好ましくは1~30%、より好ましくは1~20%、さらに好ましくは1~15%である。 As the other dispersant mentioned above, it is possible to use, for example, a styrene-(meth)acrylic copolymer, a formalin condensate of aromatic sulfonic acid, or a salt thereof. The styrene-(meth)acrylic copolymer is a copolymer of a styrene monomer and a (meth)acrylic monomer. In this specification, "(meth)acrylic" means "acrylic" and/or "methacrylic". Specific examples of these copolymers include (α-methyl)styrene-acrylic acid copolymer, (α-methyl)styrene-acrylic acid-acrylic acid ester copolymer, and (α-methyl)styrene-methacrylic acid copolymer. Polymer, (α-methyl)styrene-methacrylic acid-acrylic ester copolymer, (α-methyl)styrene-(anhydrous) maleic acid copolymer, acrylic ester-(anhydrous) maleic acid copolymer, ( α-methyl)styrene-acrylic acid ester-(anhydrous)maleic acid copolymer, acrylic acid ester-allylsulfonic acid ester copolymer, acrylic acid ester-styrene sulfonic acid copolymer, (α-methyl)styrene-methacrylic Examples include sulfonic acid copolymer, polyester-acrylic acid copolymer, polyester-acrylic acid-acrylic acid ester copolymer, polyester-methacrylic acid copolymer, polyester-methacrylic acid-acrylic acid copolymer ester; . Among these, styrene compounds containing an aromatic hydrocarbon group are preferred. Note that (α-methyl)styrene is used herein to include α-methylstyrene and styrene. In the colored dispersion, the other dispersant includes at least one dispersant selected from the group consisting of styrene-(meth)acrylic copolymer, formalin condensate of aromatic sulfonic acid, or a salt thereof. Preferably. The content of other dispersants in the colored dispersion is usually 1 to 36%, preferably 1 to 30%, more preferably 1 to 20%, and still more preferably 1 to 15%.
上記その他の分散剤の具体例としては、JoncrylRTM 52J、57J、60J、63J、70J、JDX-6180、HPD-196、HPD96J、PDX-6137A、6610、JDX-6500、JDX-6639、PDX-6102B、PDX-6124、67、678、680、682、683、690(BASF製)等を挙げることができるが、これらに限定されるものではない。なお本明細書において上付きのRTMは登録商標を意味する。 Specific examples of the other dispersants mentioned above include Joncryl RTM 52J, 57J, 60J, 63J, 70J, JDX-6180, HPD-196, HPD96J, PDX-6137A, 6610, JDX-6500, JDX-6639, PDX-6102B. , PDX-6124, 67, 678, 680, 682, 683, 690 (manufactured by BASF), but are not limited to these. Note that in this specification, the superscript RTM means a registered trademark.
上記その他の分散剤は、重量平均分子量が、1,000~20,000である場合が好ましく、2,000~19,000が更に好ましく、5,000~17,000が特に好ましい。上記スチレン-アクリル酸系共重合体の重量平均分子量は、GPC(ゲルパーミッションクロマトグラフ)法で測定する。また、分散剤として用いられるスチレン-(メタ)アクリル共重合体の酸価は50~250mgKOH/gである場合が好ましく、100~250mgKOH/gがさらに好ましく、150~250mgKOH/gである場合が特に好ましい。酸価が小さくなりすぎると、水に対する樹脂の溶解性が悪くなり、特に着色剤が分散性染料の場合、分散安定化力が劣る傾向にあり、酸価が大きくなりすぎると水性媒体との親和性が強くなり、印字後の画像ににじみが発生し易い傾向があり好ましくない。樹脂の酸価は、樹脂1gを中和するのに要するKOHのmg数を表し、JIS-K3054に従って測定する。さらに、分散剤として用いられるスチレン-(メタ)アクリル共重合体のガラス転位温度は45℃~135℃である場合が好ましく、55℃~120℃がさらに好ましく、60~110℃が特に好ましい。 The weight average molecular weight of the other dispersants mentioned above is preferably from 1,000 to 20,000, more preferably from 2,000 to 19,000, and particularly preferably from 5,000 to 17,000. The weight average molecular weight of the styrene-acrylic acid copolymer is measured by GPC (gel permeation chromatography). Furthermore, the acid value of the styrene-(meth)acrylic copolymer used as a dispersant is preferably 50 to 250 mgKOH/g, more preferably 100 to 250 mgKOH/g, particularly 150 to 250 mgKOH/g. preferable. If the acid value becomes too low, the solubility of the resin in water will deteriorate, and especially if the colorant is a dispersive dye, the dispersion stabilizing power will tend to be poor, and if the acid value becomes too large, the compatibility with the aqueous medium will decrease. This is undesirable because it tends to make the printed image more prone to bleeding. The acid value of the resin represents the number of mg of KOH required to neutralize 1 g of the resin, and is measured according to JIS-K3054. Further, the glass transition temperature of the styrene-(meth)acrylic copolymer used as a dispersant is preferably 45°C to 135°C, more preferably 55°C to 120°C, particularly preferably 60°C to 110°C.
上記着色分散液における、好ましいその他の分散剤であるスチレン-(メタ)アクリル共重合体の具体例としては、Joncryl 67(重量平均分子量=12,500、酸価=213mgKOH/g)、678(重量平均分子量=8,500、酸価=215mgKOH/g)、682(重量平均分子量=1,700、酸価=230mgKOH/g)、683(重量平均分子量=4,900、酸価=215mgKOH/g)、690(重量平均分子量=16,500、酸価=240mgKOH/g)等が挙げられ、Joncryl 678であることがより好ましい。 Specific examples of styrene-(meth)acrylic copolymers which are other preferable dispersants in the colored dispersion include Joncryl 67 (weight average molecular weight = 12,500, acid value = 213 mgKOH/g), 678 (weight average molecular weight = 12,500, acid value = 213 mgKOH/g), Average molecular weight = 8,500, acid value = 215 mgKOH/g), 682 (weight average molecular weight = 1,700, acid value = 230 mgKOH/g), 683 (weight average molecular weight = 4,900, acid value = 215 mgKOH/g) , 690 (weight average molecular weight = 16,500, acid value = 240 mgKOH/g), and Joncryl 678 is more preferred.
上記着色分散液は、上記式(1)で表される化合物、Disperse Blue 360、任意で含む上記イエロー系染料、任意で含む上記ブルー系染料、及び上記その他染料の分散または溶解時に、上記分散剤に加え、2種類以上のスチレン-アクリル共重合体を使用して作製することが可能である。 The above-mentioned colored dispersion liquid includes the above-mentioned dispersant when dispersing or dissolving the compound represented by the above formula (1), Disperse Blue 360, the above-mentioned yellow dye optionally included, the above-mentioned blue dye optionally containing, and the above-mentioned other dyes. In addition to styrene-acrylic copolymers, two or more types of styrene-acrylic copolymers can be used.
上記式(1)で表される化合物、Disperse Blue 360、任意で含む上記イエロー系染料、任意で含む上記ブルー系染料、及びその他染料の分散は、例えば以下の方法で行うことができる。スチレン-アクリル共重合体を水溶性有機溶剤に投入し、温度を90-120℃に昇温してスチレン-アクリル共重合体溶解液を作製し、そこへアルカリ性化合物及び水を投入して、温度を下げて乳化(エマルション又はマイクロエマルション)液とし、作製されたエマルション液と上記式(1)で表される化合物、Disperse Blue 360、任意で含む上記イエロー系染料、任意で含む上記ブルー系染料、及びその他染料を混合、分散を行う。 Dispersion of the compound represented by the above formula (1), Disperse Blue 360, the optionally included yellow dye, the optionally included blue dye, and other dyes can be performed, for example, by the following method. The styrene-acrylic copolymer was added to a water-soluble organic solvent and the temperature was raised to 90-120°C to prepare a styrene-acrylic copolymer solution, and an alkaline compound and water were added thereto. to obtain an emulsified (emulsion or microemulsion) liquid, and the prepared emulsion liquid and the compound represented by the above formula (1), Disperse Blue 360, the optionally included yellow dye, the optionally included blue dye, Mix and disperse other dyes.
上記芳香族スルホン酸のホルマリン縮合物又はその塩は、芳香族スルホン酸とホルマリンの縮合反応によって得られる陰イオン性の界面活性剤である。「その塩」としては、ナトリウム塩、カリウム塩、リチウム塩等の塩が挙げられる。上記芳香族スルホン酸のホルマリン縮合物又はその塩は、芳香族スルホン酸のホルマリン縮合物又はその塩若しくはそれらの混合物(以下、特に断りのない限り「スルホン酸のホルマリン縮合物」と記載したときは、「その塩、もしくはそれらの混合物」も含む意味を有する)等が好ましい。例えば、クレオソート油スルホン酸、クレゾールスルホン酸、フェノールスルホン酸、β-ナフタレンスルホン酸、β-ナフトールスルホン酸、β-ナフタリンスルホン酸とβ-ナフトールスルホン酸、ベンゼンスルホン酸、クレゾールスルホン酸、2-ナフトール-6-スルホン酸、リグニンスルホン酸等のホルマリン縮合物が挙げられる。これらの中では、クレオソート油スルホン酸、β-ナフタレンスルホン酸、リグニンスルホン酸、メチルナフタレンスルホン酸の各ホルマリン縮合物が好ましい。これらは様々な商品名の市販品として入手することができる。その一例として、β-ナフタレンスルホン酸のホルマリン縮合物としてはデモールN、クレオソート油スルホン酸のホルマリン縮合物としてはデモールC;特殊芳香族スルホン酸のホルマリン縮合物としてはデモールSN-B(いずれも花王株式会社製);等が挙げられる。クレオソート油スルホン酸のホルマリン縮合物としては、ラベリンWシリーズ、メチルナフタレンスルホン酸のホルマリン縮合物としては、ラベリンANシリーズ(いずれも第一工業製薬株式会社製)、等が挙げられる。これらの中ではデモールN、ラベリンANシリーズ、ラベリンWシリーズが好ましく、デモールN、ラベリンWがより好ましく、ラベリンWがさらに好ましい。リグニンスルホン酸としては、例えばバニレックスN、バニレックスRN、バニレックスG、パールレックスDP(いずれも日本製紙株式会社製)等が挙げられる。これらの中ではバニレックスRN、バニレックスN、バニレックスGが好ましい。 The formalin condensate of aromatic sulfonic acid or its salt is an anionic surfactant obtained by a condensation reaction of aromatic sulfonic acid and formalin. Examples of "salts thereof" include salts such as sodium salts, potassium salts, and lithium salts. The above-mentioned formalin condensate of aromatic sulfonic acid or a salt thereof is a formalin condensate of aromatic sulfonic acid, a salt thereof, or a mixture thereof (hereinafter, unless otherwise specified, when described as "formalin condensate of sulfonic acid") , ``salts thereof, or mixtures thereof'') are preferred. For example, creosote oil sulfonic acid, cresol sulfonic acid, phenolsulfonic acid, β-naphthalene sulfonic acid, β-naphthol sulfonic acid, β-naphthalene sulfonic acid and β-naphthol sulfonic acid, benzene sulfonic acid, cresol sulfonic acid, 2- Examples include formalin condensates such as naphthol-6-sulfonic acid and ligninsulfonic acid. Among these, formalin condensates of creosote oil sulfonic acid, β-naphthalene sulfonic acid, lignin sulfonic acid, and methylnaphthalene sulfonic acid are preferred. These are commercially available under various trade names. For example, Demol N is a formalin condensate of β-naphthalene sulfonic acid, Demol C is a formalin condensate of creosote oil sulfonic acid, and Demol SN-B is a formalin condensate of special aromatic sulfonic acid (both are (manufactured by Kao Corporation); and the like. Examples of the formalin condensate of creosote oil sulfonic acid include the Lavelin W series, and examples of the formalin condensate of methylnaphthalene sulfonic acid include the Lavelin AN series (both manufactured by Daiichi Kogyo Seiyaku Co., Ltd.). Among these, Demol N, Lavelin AN series, and Lavelin W series are preferred, Demol N and Lavelin W are more preferred, and Lavelin W is even more preferred. Examples of the lignin sulfonic acid include Vanillex N, Vanillex RN, Vanillex G, and Pearlex DP (all manufactured by Nippon Paper Industries Co., Ltd.). Among these, Vanillex RN, Vanillex N, and Vanillex G are preferred.
上記着色分散液は、さらに水溶性有機溶剤を含むことができる。 The colored dispersion liquid may further contain a water-soluble organic solvent.
上記水溶性有機溶剤としては、例えば、グリコール系溶剤、多価アルコール類、ピロリドン類等を挙げることができる。グリコール系溶剤としては、グリセリン、ポリグリセリン(#310、#750、#800、)、ジグリセリン、トリグリセリン、テトラグリセリン、ペンタグリセリン、ヘキサグリセリン、ヘプタグリセリン、オクタグリセリン、ノナグリセリン、デカグリセリン、ウンデカグリセリン、ドデカグリセリン、トリデカグリセリン、テトラデカグリセリン等の化合物、及びこれらの混合物が挙げられる。多価アルコール類としては、例えばアルコール性水酸基を2~3個有するC2~C6多価アルコール及び、ジ又はトリC2~C3アルキレングリコール若しくは繰り返し単位が4以上で、分子量20,000程度以下のポリC2~C3アルキレングリコール、好ましくは液状のポリアルキレングリコール等が挙げられる。それらの具体例としてはエチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、ポリエチレングリコール、ポリプロピレングリコール、1,3-プロパンジオール、1,2-ブタンジオール、チオジグリコール、1,3-ブタンジオール、1,4-ブタンジオール、2,3-ブタンジオール、3-メチル-1,3-ブタンジオール、1,2-ペンタンジオール、1,5-ペンタンジオール、2-メチル-2,4-ペンタンジオール、3-メチル-1,5-ペンタンジオール、1,2-ヘキサンジオール、1,6-ヘキサンジオール、グリセリン、トリメチロールプロパン、1,3-ペンタンジオール、1,5-ペンタンジオール等の多価アルコール類、2-ピロリドン、N-メチル-2-ピロリドン等が挙げられ、グリセリン又はジグリセリンのいずれかを少なくとも含むことが好ましい。また、水に溶解して湿潤剤としての役割をする化合物等も、便宜上本発明では水溶性有機溶剤に含めるものとし、例えば尿素、エチレン尿素及び糖類等が挙げられる。保存安定性を考慮すると、着色剤が分散染料や油溶性染料である場合、それらの溶解度が小さい溶剤が好ましく、これらの中でも特にグリセリンと、グリセリン以外の溶剤(好ましくはグリセリン以外の多価アルコール)とを併用するのが好ましい。上記着色分散液の総質量中における、水溶性有機溶剤の総含有量は、5~50%であり、10~40%添加するのが好ましい。 Examples of the water-soluble organic solvent include glycol solvents, polyhydric alcohols, and pyrrolidones. Examples of glycol solvents include glycerin, polyglycerin (#310, #750, #800), diglycerin, triglycerin, tetraglycerin, pentaglycerin, hexaglycerin, heptaglycerin, octaglycerin, nonaglycerin, decaglycerin, and Examples include compounds such as decaglycerin, dodecaglycerin, tridecaglycerin, tetradecaglycerin, and mixtures thereof. Examples of polyhydric alcohols include C2-C6 polyhydric alcohols having 2 to 3 alcoholic hydroxyl groups, di- or tri-C2-C3 alkylene glycols, or polyC2 polyhydric alcohols having 4 or more repeating units and a molecular weight of about 20,000 or less. -C3 alkylene glycol, preferably liquid polyalkylene glycol. Specific examples thereof include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, 1,3-propanediol, 1,2-butanediol, thiodiglycol, 1,3-butanediol, 1 , 4-butanediol, 2,3-butanediol, 3-methyl-1,3-butanediol, 1,2-pentanediol, 1,5-pentanediol, 2-methyl-2,4-pentanediol, 3 - Polyhydric alcohols such as methyl-1,5-pentanediol, 1,2-hexanediol, 1,6-hexanediol, glycerin, trimethylolpropane, 1,3-pentanediol, 1,5-pentanediol, Examples include 2-pyrrolidone and N-methyl-2-pyrrolidone, and preferably contain at least either glycerin or diglycerin. Further, for convenience, compounds that dissolve in water and serve as wetting agents are included in the water-soluble organic solvent in the present invention, such as urea, ethylene urea, sugars, and the like. Considering storage stability, when the colorant is a disperse dye or an oil-soluble dye, a solvent in which the colorant has a low solubility is preferable, and among these, glycerin and a solvent other than glycerin (preferably a polyhydric alcohol other than glycerin) are preferable. It is preferable to use them together. The total content of the water-soluble organic solvent in the total mass of the colored dispersion is 5 to 50%, preferably 10 to 40%.
上記着色分散液は、さらに添加剤を含むことができる。 The colored dispersion liquid may further contain an additive.
上記添加剤としては、例えば、防腐剤、界面活性剤、pH調整剤、キレート試薬、防錆剤、水溶性紫外線吸収剤、水溶性高分子化合物、粘度調整剤、色素溶解剤、褪色防止剤、酸化防止剤、水等が挙げられる。 Examples of the additives include preservatives, surfactants, pH adjusters, chelating reagents, rust preventives, water-soluble ultraviolet absorbers, water-soluble polymer compounds, viscosity modifiers, dye solubilizers, anti-fading agents, Examples include antioxidants and water.
上記防腐剤としては、例えば、有機硫黄系、有機窒素硫黄系、有機ハロゲン系、ハロアリルスルホン系、ヨードプロパギル系、N-ハロアルキルチオ系、ニトリル系、ピリジン系、8-オキシキノリン系、ベンゾチアゾール系、イソチアゾリン系、ジチオール系、ピリジンオキシド系、ニトロプロパン系、有機スズ系、フェノール系、第4アンモニウム塩系、トリアジン系、チアジン系、アニリド系、アダマンタン系、ジチオカーバメイト系、ブロム化インダノン系、ベンジルブロムアセテート系、無機塩系等の化合物が挙げられる。有機ハロゲン系化合物の具体例としては、例えばペンタクロロフェノールナトリウムが挙げられ、ピリジンオキシド系化合物の具体例としては、例えば2-ピリジンチオール-1-オキサイドナトリウムが挙げられ、イソチアゾリン系化合物の具体例としては、例えば、1,2-ベンズイソチアゾリン-3-オン、2-n-オクチル-4-イソチアゾリン-3-オン、5-クロロ-2-メチル-4-イソチアゾリン-3-オン、5-クロロ-2-メチル-4-イソチアゾリン-3-オンマグネシウムクロライド、5-クロロ-2-メチル-4-イソチアゾリン-3-オンカルシウムクロライド、2-メチル-4-イソチアゾリン-3-オンカルシウムクロライド等が挙げられる。その他の防腐防黴剤の具体例として、無水酢酸ソーダ、ソルビン酸ソーダ又は安息香酸ナトリウム、アーチケミカル社製、商品名プロクセルRTMGXL(S)やプロクセルRTMXL-2(S)等が挙げられる。 Examples of the above-mentioned preservatives include organic sulfur-based, organic nitrogen-sulfur-based, organic halogen-based, haloallylsulfone-based, iodopropargyl-based, N-haloalkylthio-based, nitrile-based, pyridine-based, 8-oxyquinoline-based, benzo Thiazole series, isothiazoline series, dithiol series, pyridine oxide series, nitropropane series, organotin series, phenol series, quaternary ammonium salt series, triazine series, thiazine series, anilide series, adamantane series, dithiocarbamate series, brominated indanone series , benzyl bromoacetate type, and inorganic salt type compounds. Specific examples of organic halogen compounds include sodium pentachlorophenol, specific examples of pyridine oxide compounds include sodium 2-pyridinethiol-1-oxide, and specific examples of isothiazoline compounds include is, for example, 1,2-benzisothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one, 5-chloro-2 -Methyl-4-isothiazolin-3-one magnesium chloride, 5-chloro-2-methyl-4-isothiazolin-3-one calcium chloride, 2-methyl-4-isothiazolin-3-one calcium chloride, and the like. Specific examples of other preservatives and antifungal agents include anhydrous sodium acetate, sodium sorbate, or sodium benzoate, manufactured by Arch Chemical Co., Ltd., trade names Proxel RTM GXL (S) and Proxel RTM XL-2 (S).
上記界面活性剤としては、アニオン系、カチオン系、ノニオン系、シリコーン系等の公知の界面活性剤が挙げられる。アニオン界面活性剤としては、アルキルスルホン酸塩、アルキルカルボン酸塩、α-オレフィンスルホン酸塩、ポリオキシエチレンアルキルエーテル酢酸塩、N-アシルアミノ酸及びその塩、N-アシルメチルタウリン塩、アルキル硫酸塩ポリオキシアルキルエーテル硫酸塩、アルキル硫酸塩ポリオキシエチレンアルキルエーテル燐酸塩、ロジン酸石鹸、ヒマシ油硫酸エステル塩、ラウリルアルコール硫酸エステル塩、アルキルフェノール型燐酸エステル、アルキル型燐酸エステル、アルキルアリールスルホン酸塩、ジエチルスルホ琥珀酸塩、ジエチルヘキルシルスルホ琥珀酸塩、ジオクチルスルホ琥珀酸塩等が挙げられる。その市販品の具体例としては、例えば、いずれも第一工業製薬社製のハイテノールLA-10、LA-12、LA-16、ネオハイテノールECL-30S、ECL-45などが挙げられる。カチオン界面活性剤としては、2-ビニルピリジン誘導体、ポリ4-ビニルピリジン誘導体等が挙げられる。両性界面活性剤としては、ラウリルジメチルアミノ酢酸ベタイン、2-アルキル-N-カルボキシメチル-N-ヒドロキシエチルイミダゾリニウムベタイン、ヤシ油脂肪酸アミドプロピルジメチルアミノ酢酸ベタイン、ポリオクチルポリアミノエチルグリシン、イミダゾリン誘導体等が挙げられる。ノニオン界面活性剤としては、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンオクチルフェニルエーテル、ポリオキシエチレンドデシルフェニルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンアルキルエーテル等のエーテル系;ポリオキシエチレンオレイン酸エステル、ポリオキシエチレンジステアリン酸エステル、ソルビタンラウレート、ソルビタンモノステアレート、ソルビタンモノオレエート、ソルビタンセスキオレエート、ポリオキシエチレンモノオレエート、ポリオキシエチレンステアレート等のエステル系;2,4,7,9-テトラメチル-5-デシン-4,7-ジオール、3,6-ジメチル-4-オクチン-3,6-ジオール、3,5-ジメチル-1-ヘキシン-3-オール等のアセチレングリコール(アルコール)系;日信化学社製、商品名サーフィノール104、105、82、465、オルフィンSTG等;ポリグリコールエーテル系(例えばSIGMA-ALDRICH社製のTergitol 15-S-7等);等が挙げられる。 Examples of the surfactant include known surfactants such as anionic, cationic, nonionic, and silicone surfactants. Examples of anionic surfactants include alkyl sulfonates, alkyl carboxylates, α-olefin sulfonates, polyoxyethylene alkyl ether acetates, N-acylamino acids and their salts, N-acylmethyl taurine salts, and alkyl sulfates. Polyoxyalkyl ether sulfate, alkyl sulfate polyoxyethylene alkyl ether phosphate, rosin acid soap, castor oil sulfate, lauryl alcohol sulfate, alkylphenol type phosphate, alkyl type phosphate, alkylaryl sulfonate, Examples include diethyl sulfosuccinate, diethylhexyl sulfosuccinate, dioctyl sulfosuccinate, and the like. Specific examples of commercially available products include Hitenol LA-10, LA-12, LA-16, Neo Hitenol ECL-30S, and ECL-45, all manufactured by Daiichi Kogyo Seiyaku Co., Ltd. Examples of the cationic surfactant include 2-vinylpyridine derivatives and poly-4-vinylpyridine derivatives. Examples of amphoteric surfactants include lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, coconut oil fatty acid amidopropyldimethylaminoacetic acid betaine, polyoctylpolyaminoethylglycine, imidazoline derivatives, etc. can be mentioned. Examples of nonionic surfactants include ethers such as polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene dodecylphenyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, and polyoxyethylene alkyl ether; Ester systems such as polyoxyethylene oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, polyoxyethylene monooleate, polyoxyethylene stearate; 2,4,7,9-tetramethyl-5-decyne-4,7-diol, 3,6-dimethyl-4-octyne-3,6-diol, 3,5-dimethyl-1-hexyn-3-ol Acetylene glycol (alcohol) type products such as Nissin Kagaku Co., Ltd., trade name Surfynol 104, 105, 82, 465, Olfine STG, etc.; Polyglycol ether type (e.g. Tergitol 15-S-7, manufactured by SIGMA-ALDRICH Co., Ltd.) ); etc.
上記シリコーン系界面活性剤としては、例えば、ポリエーテル変性シロキサン、ポリエーテル変性ポリジメチルシロキサン等が挙げられる。市販品の具体例としては、例えば、いずれもビックケミー社製の、BYK-347(ポリエーテル変性シロキサン);BYK-345、BYK-348(ポリエーテル変性ポリジメチルシロキサン)等が挙げられる。フッ素系界面活性剤としては、例えば、パーフルオロアルキルスルホン酸化合物、パーフルオロアルキルカルボン酸系化合物、パーフルオロアルキルリン酸エステル化合物、パーフルオロアルキルエチレンオキサイド付加物、及びパーフルオロアルキルエーテル基を側鎖に有するポリオキシアルキレンエーテルポリマー化合物等が挙げられる。市販品の具体例としては、例えば、Zonyl TBS、FSP、FSA、FSN-100、FSN、FSO-100、FSO、FS-300、Capstone FS-30、FS-31(DuPont社製);PF-151N、PF-154N(オムノバ社製)等が挙げられる。 Examples of the silicone surfactant include polyether-modified siloxane, polyether-modified polydimethylsiloxane, and the like. Specific examples of commercially available products include BYK-347 (polyether-modified siloxane); BYK-345 and BYK-348 (polyether-modified polydimethylsiloxane), both manufactured by BYK Chemie. Examples of fluorine-based surfactants include perfluoroalkyl sulfonic acid compounds, perfluoroalkyl carboxylic acid compounds, perfluoroalkyl phosphate compounds, perfluoroalkyl ethylene oxide adducts, and perfluoroalkyl ether groups in side chains. Examples include polyoxyalkylene ether polymer compounds. Specific examples of commercially available products include, for example, Zonyl TBS, FSP, FSA, FSN-100, FSN, FSO-100, FSO, FS-300, Capstone FS-30, FS-31 (manufactured by DuPont); PF-151N , PF-154N (manufactured by Omnova), etc.
上記pH調整剤としては、調製される上記着色分散液に悪影響を及ぼさずに、溶液のpHをおおよそ5~11の範囲に制御できるものであれば任意の物質を使用することができる。その具体例としては、例えば、ジエタノールアミン、トリエタノールアミン、N-メチルジエタノールアミン等のアルカノールアミン;水酸化リチウム、水酸化ナトリウム、水酸化カリウム等のアルカリ金属の水酸化物;水酸化アンモニウム(アンモニア水);、炭酸リチウム、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩;酢酸カリウム等の有機酸のアルカリ金属塩;ケイ酸ナトリウム、リン酸二ナトリウム等の無機塩基等が挙げられ、トリエタノールアミンが好ましい。 As the pH adjuster, any substance can be used as long as it can control the pH of the solution within the range of approximately 5 to 11 without adversely affecting the colored dispersion being prepared. Specific examples include alkanolamines such as diethanolamine, triethanolamine, and N-methyldiethanolamine; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; ammonium hydroxide (aqueous ammonia); ; carbonates of alkali metals such as lithium carbonate, sodium carbonate, sodium bicarbonate, potassium carbonate; alkali metal salts of organic acids such as potassium acetate; inorganic bases such as sodium silicate and disodium phosphate; Triethanolamine is preferred.
上記キレート試薬の具体例としては、例えば、エチレンジアミン四酢酸ナトリウム、ニトリロ三酢酸ナトリウム、ヒドロキシエチルエチレンジアミン三酢酸ナトリウム、ジエチレントリアミン五酢酸ナトリウム、ウラシル二酢酸ナトリウム等があげられる。 Specific examples of the above-mentioned chelating reagents include sodium ethylenediaminetetraacetate, sodium nitrilotriacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, and sodium uracildiacetate.
上記防錆剤としては、例えば、酸性亜硫酸塩、チオ硫酸ナトリウム、チオグルコール酸アンモニウム、ジイソプロピルアンモニウムナイトライト、四硝酸ペンタエリスリトール又はジシクロヘキシルアンモニウムナイトライト等があげられる。 Examples of the rust preventive include acidic sulfite, sodium thiosulfate, ammonium thioglycolate, diisopropylammonium nitrite, pentaerythritol tetranitrate, and dicyclohexylammonium nitrite.
上記水溶性紫外線吸収剤としては、例えばスルホン化したベンゾフェノン系化合物、ベンゾトリアゾ-ル系化合物、サリチル酸系化合物、桂皮酸系化合物、トリアジン系化合物が挙げられる。 Examples of the water-soluble ultraviolet absorbers include sulfonated benzophenone compounds, benzotriazole compounds, salicylic acid compounds, cinnamic acid compounds, and triazine compounds.
上記水溶性高分子化合物としては、ポリビニルアルコール、セルロース誘導体、ポリアミン又はポリイミン等があげられる。 Examples of the water-soluble polymer compound include polyvinyl alcohol, cellulose derivatives, polyamines, and polyimines.
上記粘度調整剤としては、水溶性有機溶剤の他に、水溶性高分子化合物が挙げられ、例えば、ポリビニルアルコール、セルロース誘導体、ポリアミン、ポリイミン等が挙げられる。 Examples of the viscosity modifier include water-soluble polymer compounds in addition to water-soluble organic solvents, such as polyvinyl alcohol, cellulose derivatives, polyamines, and polyimines.
上記色素溶解剤としては、例えば、尿素、ε-カプロラクタム、エチレンカーボネート等が挙げられる。 Examples of the dye dissolving agent include urea, ε-caprolactam, and ethylene carbonate.
上記褪色防止剤は、画像の保存性を向上させる目的で使用される。褪色防止剤としては、各種の有機系及び金属錯体系の褪色防止剤を使用することができる。有機系としては、ハイドロキノン類、アルコキシフェノール類、ジアルコキシフェノール類、フェノール類、アニリン類、アミン類、インダン類、クロマン類、アルコキシアニリン類、及びヘテロ環類等が挙げられる。金属錯体系としては、ニッケル錯体、亜鉛錯体等が挙げられる。 The above-mentioned anti-fading agent is used for the purpose of improving the storage stability of images. As the anti-fading agent, various organic and metal complex anti-fading agents can be used. Examples of the organic type include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indanes, chromans, alkoxyanilines, and heterocycles. Examples of metal complex systems include nickel complexes and zinc complexes.
上記酸化防止剤としては、例えば、各種の有機系及び金属錯体系の褪色防止剤を使用することができる。前記有機系の褪色防止剤の例としては、ハイドロキノン類、アルコキシフェノール類、ジアルコキシフェノール類、フェノール類、アニリン類、アミン類、インダン類、クロマン類、アルコキシアニリン類、複素環類等が挙げられる。 As the antioxidant, for example, various organic and metal complex anti-fading agents can be used. Examples of the organic anti-fading agents include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indanes, chromans, alkoxyanilines, heterocycles, etc. .
上記着色分散液は、水を含むことができる。用いうる水は、イオン交換水、蒸留水等の不純物が少ないものが好ましい。また、上記着色分散液に対してメンブランフィルター等を用いた精密濾過を行うことができる。上記着色分散液をインクジェット捺染インク用として使用するときは、ノズルの目詰まり等を防止する目的で、精密濾過を行うことが好ましい。精密濾過に使用するフィルターの孔径は通常1μm~0.1μm、好ましくは0.8μm~0.1μmである。 The colored dispersion liquid may contain water. The water that can be used is preferably one containing few impurities, such as ion-exchanged water or distilled water. Further, the colored dispersion liquid may be subjected to precision filtration using a membrane filter or the like. When the colored dispersion is used as an inkjet textile ink, it is preferable to perform precision filtration in order to prevent nozzle clogging. The pore size of the filter used for precision filtration is usually 1 μm to 0.1 μm, preferably 0.8 μm to 0.1 μm.
上記着色分散液において、上記添加剤として、防腐剤、界面活性剤、pH調整剤からなる群から選択されるいずれか少なくとも1つを含むことが好ましい。 The colored dispersion preferably contains at least one selected from the group consisting of preservatives, surfactants, and pH adjusters as the additive.
上記着色分散液は、さらに、樹脂エマルションを含んでいても良い。 The colored dispersion liquid may further contain a resin emulsion.
上記樹脂エマルションとしては、例えば、アクリル樹脂、エポキシ樹脂、ウレタン樹脂、スチレンブタジエン樹脂、ポリエーテル樹脂、ポリアミド樹脂、不飽和ポリエステル樹脂、フェノール樹脂、シリコーン樹脂、フッ素樹脂、ポリビニル樹脂(例:塩化ビニル、酢酸ビニル、ポリビニルアルコール等)、アルキド樹脂、ポリエステル樹脂、又はアミノ材料(メラニン樹脂、ユリア樹脂、尿素樹脂、メラニンホルムアルデヒド樹脂等)から形成されたエマルションがある。また、それらエマルションは2種以上の樹脂から構成されていても良い。さらに2種以上の樹脂がコア/シェル構造を形成した形態の複合樹脂であっても良い。それら樹脂エマルションの中でも上記着色分散液に使用するには、ウレタン樹脂が好ましい。 Examples of the resin emulsions include acrylic resins, epoxy resins, urethane resins, styrene-butadiene resins, polyether resins, polyamide resins, unsaturated polyester resins, phenolic resins, silicone resins, fluororesins, polyvinyl resins (e.g. vinyl chloride, There are emulsions formed from vinyl acetate, polyvinyl alcohol, etc.), alkyd resins, polyester resins, or amino materials (melanin resins, urea resins, urea resins, melanin formaldehyde resins, etc.). Further, these emulsions may be composed of two or more kinds of resins. Furthermore, it may be a composite resin in which two or more resins form a core/shell structure. Among these resin emulsions, urethane resins are preferred for use in the colored dispersion.
上記ウレタン樹脂は、ラテックス(エマルション)の形で販売されていることも多く、その多くは固形分が30~60%での乳化液である。その具体例としては、例えば、パーマリンUA-150、200、310、368、3945、ユーコートUX-320(以上、三洋化成株式会社製)、ハイドランWLS-201、210、HW-312Bのラテックス(以上、DIC株式会社製)、スーパーフレックス150、170、470(以上、第一工業製薬株式会社製)、等が挙げられる。これらのうち、ポリカーボネート系ウレタン樹脂としては、例えば、パーマリンUA-310、3945、ユーコートUX-320、等が挙げられる。これらのうち、ポリエーテル系ウレタン樹脂としては、例えば、パーマリンUA-150、200、ユーコートUX-340、等が挙げられる。これらウレタン樹脂は単独で使用することも、併用することもできる。 The above-mentioned urethane resin is often sold in the form of latex (emulsion), and most of these are emulsions with a solid content of 30 to 60%. Specific examples include Permarine UA-150, 200, 310, 368, 3945, Ucoat UX-320 (manufactured by Sanyo Chemical Co., Ltd.), Hydran WLS-201, 210, HW-312B latex (all of the above, (manufactured by DIC Corporation), Superflex 150, 170, 470 (manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), and the like. Among these, examples of polycarbonate-based urethane resins include Permarin UA-310, 3945, and Ucoat UX-320. Among these, examples of the polyether urethane resin include Permarin UA-150, UA-200, Ucoat UX-340, and the like. These urethane resins can be used alone or in combination.
上記ウレタン樹脂のエマルションは、SP値(溶解度パラメータ)が8~24(cal/cm3)1/2である場合が好ましく、8~17(cal/cm3)1/2がさらに好ましく、8~11が特に好ましい。なお、ウレタン樹脂のSP値はFedors法によって計算される。また、ウレタン樹脂エマルション中の樹脂が酸性基を有していた場合、この酸性基を中和してエマルションを作製している場合には中和前の樹脂のSP値を用いる。 The urethane resin emulsion preferably has an SP value (solubility parameter) of 8 to 24 (cal/cm 3 ) 1/2 , more preferably 8 to 17 (cal/cm 3 ) 1/2, and more preferably 8 to 24 (cal/cm 3 ) 1/2 . 11 is particularly preferred. Note that the SP value of the urethane resin is calculated by the Fedors method. Furthermore, if the resin in the urethane resin emulsion has acidic groups and the emulsion is prepared by neutralizing these acidic groups, the SP value of the resin before neutralization is used.
上記ウレタン樹脂エマルションが、カルボン酸、スルホン酸、水酸基等の酸性基を有する場合、それら酸性基は、アルカリ塩化されていても良い。アルカリ塩化は、例えば以下方法で行うことが可能である。酸性基を有するウレタン樹脂エマルションを水に投入し撹拌して水溶液を調製し、該水溶液にアルカリ性化合物を加え、pHを6.0~12.0に調整した液を作製する方法などが挙げられる。 When the urethane resin emulsion has acidic groups such as carboxylic acid, sulfonic acid, and hydroxyl groups, these acidic groups may be converted into alkali salts. Alkali chlorination can be carried out, for example, by the following method. Examples include a method in which a urethane resin emulsion having an acidic group is poured into water and stirred to prepare an aqueous solution, and an alkaline compound is added to the aqueous solution to prepare a liquid whose pH is adjusted to 6.0 to 12.0.
上記アルカリ性化合物としては、例えば、水酸化リチウム、水酸化ナトリウム及び水酸化カリウム等のアルカリ金属の水酸化物、水酸化ベリリウム、水酸化マグネシウム、水酸化カルシウム及び水酸化ストロンチウム等のアルカリ土類金属の水酸化物やトリエチルアミン等が挙げられる。これらアルカリ性化合物は任意の1種類のみを使用しても良く、あるいは、2種類以上を組み合わせて使用しても良い。 Examples of the alkaline compounds include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as beryllium hydroxide, magnesium hydroxide, calcium hydroxide, and strontium hydroxide. Examples include hydroxide and triethylamine. These alkaline compounds may be used alone or in combination of two or more.
上記式(1)で表される化合物は、粉末状あるいは塊状の乾燥色材でも、ウエットケーキやスラリーでも良く、化合物合成中や合成後に粒子の凝集を抑える目的として、界面活性剤等の分散剤が少量含有されたものであっても良い。 The compound represented by the above formula (1) may be a dry coloring material in the form of a powder or block, or a wet cake or slurry, and a dispersant such as a surfactant may be used to suppress particle aggregation during or after compound synthesis. It may also contain a small amount of.
上記着色分散液と、該着色分散液と異なる色相を有する着色分散液と、を含む着色分散液セットも本願発明に含まれる。また、上記式(1)表される化合物とDisperse Blue 360、あるいは、上記着色分散液の少なくともいずれかが付着した記録メディア、上記着色分散液あるいは上記着色分散液セットを用いた捺染方法も本願発明に含まれる。 A colored dispersion set including the above colored dispersion and a colored dispersion having a hue different from the colored dispersion is also included in the present invention. The present invention also includes a recording medium to which the compound represented by the above formula (1) and Disperse Blue 360 or at least one of the above-mentioned colored dispersion is attached, and a printing method using the above-mentioned colored dispersion or the above-mentioned colored dispersion set. include.
上記着色分散液を調製する方法としては、例えば、上記各構成要素を混合する方法等が挙げられる。各構成要素を混合する順番は特に制限されない。 Examples of the method for preparing the above-mentioned colored dispersion include a method of mixing the above-mentioned constituent elements. The order in which the components are mixed is not particularly limited.
上記着色分散液は、高速での吐出応答性の点から、25℃における粘度が、E型粘度計にて測定した場合の値が、通常3~20mPa・s程度であることが好ましい。また、表面張力は、プレート法にて測定した場合の値が、通常20~45mN/mの範囲が好ましい。これら各値は、使用するプリンタの吐出量、応答速度、着色分散液滴飛行特性などを考慮し、適切な値になるように調整することが好ましい。 The colored dispersion liquid preferably has a viscosity at 25° C. of usually about 3 to 20 mPa·s when measured with an E-type viscometer from the viewpoint of high-speed discharge response. Further, the surface tension is preferably in the range of usually 20 to 45 mN/m when measured by a plate method. It is preferable that each of these values is adjusted to an appropriate value, taking into consideration the ejection amount, response speed, flight characteristics of colored dispersed droplets, etc. of the printer used.
上記疎水性繊維の捺染方法は、2つの種類に大別される。1つ目の方法は、ダイレクトプリント又はダイレクト捺染等と呼称される方法であり、前記着色分散液の液滴を、インクジェット方式のプリンタにより疎水性繊維に付着させることにより、文字及び絵柄等の画像情報を疎水性繊維に形成する工程Aと、前記工程Aにより付着させた着色分散液の液滴中の昇華性染料を熱により繊維に固着させる工程Bと、繊維中に残存する未固着の昇華性染料を洗浄する工程Cと、の3工程を少なくとも含む、疎水性繊維の捺染方法である。工程Bは、一般的には公知のスチーミング又はベーキングによって行われる。スチーミングとしては、例えば高温スチーマーで通常170~180℃、通常10分程度;また、高圧スチーマーで通常120~130℃、通常20分程度;それぞれ疎水性繊維を処理する方法により、昇華性染料を繊維に染着する(湿熱固着とも呼称される)方法が挙げられる。ベーキング(サーモゾル)としては、例えば通常190℃~210℃、通常60秒~120秒程度、疎水性繊維を処理する方法により、昇華性染料を繊維に染着する(乾熱固着とも呼称される)方法が挙げられる。工程Cは、得られた繊維を、温水、及び必要に応じて水により洗浄する工程である。洗浄に使用する温水や水は、界面活性剤を含んでもよい。洗浄後の繊維を、通常50~120℃で、5~30分乾燥することも好ましく行われる。2つ目の方法は、昇華転写プリント、昇華転写捺染等と呼称される方法であり、上記着色分散液または上記着色分散液セットの液滴を、インクジェット方式のプリンタにより中間記録媒体に付着させることにより、文字及び絵柄等の記録画像を得た後、該中間記録媒体における、着色分散液の液滴の付着面に疎水性繊維を接触させ、熱処理することにより、中間記録媒体に記録された文字、絵柄等の記録画像を疎水性繊維に転写する、疎水性繊維の捺染方法である。中間記録媒体としては、中間記録媒体に付着した着色分散液中の昇華性染料が、その表面で凝集せず、且つ疎水性繊維へ記録画像の転写を行うときに、染料の昇華を妨害しないものが好ましい。そのような中間記録媒体の一例としては、シリカ等の無機微粒子で着色分散液受容層が表面に形成されている紙が挙げられ、インクジェット用の専用紙等を用いることができる。中間記録媒体から疎水性繊維へ、記録画像を転写するときの熱処理としては、通常190~200℃程度での乾熱処理が挙げられる。 The above-mentioned printing methods for hydrophobic fibers are roughly divided into two types. The first method is called direct printing or direct textile printing, in which droplets of the colored dispersion liquid are attached to hydrophobic fibers using an inkjet printer to create images such as letters and designs. Step A of forming information on hydrophobic fibers, Step B of fixing the sublimable dye in the droplets of the colored dispersion deposited in step A to the fibers by heat, and sublimation of unfixed dyes remaining in the fibers. This is a method for printing hydrophobic fibers, which includes at least three steps: a step C of washing a hydrophobic dye; Step B is generally performed by known steaming or baking. For example, steaming can be carried out using a high-temperature steamer, usually at 170 to 180 degrees Celsius, usually for about 10 minutes; or using a high-pressure steamer, usually at 120 to 130 degrees Celsius, usually for about 20 minutes; An example is a method of dyeing fibers (also called wet heat fixation). Baking (thermosol) involves dyeing the fibers with a sublimable dye using a method that treats hydrophobic fibers, for example, usually at 190°C to 210°C, usually for about 60 to 120 seconds (also called dry heat fixation). There are several methods. Step C is a step of washing the obtained fibers with warm water and, if necessary, with water. The hot water or water used for cleaning may contain a surfactant. It is also preferable to dry the washed fibers usually at 50 to 120°C for 5 to 30 minutes. The second method is a method called sublimation transfer printing, sublimation transfer printing, etc., in which droplets of the colored dispersion liquid or a set of colored dispersion liquids are attached to an intermediate recording medium using an inkjet printer. After obtaining recorded images such as characters and patterns, hydrophobic fibers are brought into contact with the surface of the intermediate recording medium on which the droplets of the colored dispersion are attached and heat-treated to produce the characters recorded on the intermediate recording medium. This is a printing method for hydrophobic fibers in which a recorded image such as a pattern is transferred onto hydrophobic fibers. The intermediate recording medium is one in which the sublimable dye in the colored dispersion adhering to the intermediate recording medium does not aggregate on its surface, and does not interfere with the sublimation of the dye when transferring the recorded image to the hydrophobic fiber. is preferred. An example of such an intermediate recording medium is paper on the surface of which a colored dispersion receiving layer is formed of inorganic fine particles such as silica, and special paper for inkjet use can be used. The heat treatment used when transferring the recorded image from the intermediate recording medium to the hydrophobic fibers usually includes dry heat treatment at about 190 to 200°C.
上記捺染方法は、にじみ等を防止する目的で、繊維の前処理工程をさらに含んでもよい。この前処理工程としては、1種類以上の糊材、アルカリ性物質、還元防止剤及びヒドロトロピー剤を少なくとも含む水溶液を、着色分散液を付着させる前の繊維に付与する工程が挙げられる。前処理を施す工程としては、糊剤、アルカリ性物質、還元防止剤及びヒドロトロピー剤を含む前処理剤の水溶液を前処理液として用い、繊維を前処理液に含浸させて付与するのが好ましい。上記糊剤としては、グアー、ローカストビーン等の天然ガム類、澱粉類、アルギン酸ソーダ、ふのり等の海藻類、ペクチン酸等の植物皮類、メチル繊維素、エチル繊維素、ヒドロキシエチルセルロース、カルボキシメチルセルロース等の繊維素誘導体、カルボキシメチル澱粉等の加工澱粉、ポリビニルアルコール、ポリアクリル酸エステル等の合成糊等があげられる。好ましくはアルギン酸ソーダがあげられる。 The above-mentioned textile printing method may further include a fiber pretreatment step for the purpose of preventing bleeding and the like. This pretreatment step includes a step of applying an aqueous solution containing at least one type of glue, an alkaline substance, a reduction inhibitor, and a hydrotropic agent to the fibers before the colored dispersion is attached. In the step of applying the pretreatment, it is preferable to use an aqueous solution of a pretreatment agent containing a sizing agent, an alkaline substance, an antireduction agent, and a hydrotropy agent as a pretreatment liquid, and to apply the fibers by impregnating them with the pretreatment liquid. Examples of the above-mentioned thickening agents include natural gums such as guar and locust bean, starches, sodium alginate, seaweeds such as funori, plant skins such as pectic acid, methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, etc. Examples include cellulose derivatives, modified starches such as carboxymethyl starch, and synthetic glues such as polyvinyl alcohol and polyacrylic acid esters. Preferred is sodium alginate.
上記アルカリ性物質としては、例えば無機酸または有機酸のアルカリ金属塩、アルカリ土類金属の塩、並びに加熱した際にアルカリを遊離する化合物が挙げられ、無機又は有機の、アルカリ金属水酸化物及びアルカリ金属塩が好ましく、ナトリウム化合物及びカリウム化合物等が挙げられる。具体例としては、例えば水酸化ナトリウム、水酸化カルシウム等のアルカリ金属水酸化物、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム、リン酸二水素ナトリウム、リン酸水素二ナトリウム、リン酸ナトリウム等の無機化合物のアルカリ金属塩、蟻酸ナトリウム、トリクロル酢酸ナトリウム等の有機化合物のアルカリ金属塩;等が挙げられる。好ましくは、炭酸水素ナトリウムが挙げられる。上記還元防止剤としては、メタニトロベンゼンスルホン酸ナトリウムが好ましい。上記ヒドロトロピー剤としては、尿素、ジメチル尿素等の尿素類等があり、好ましくは尿素が挙げられる。上記糊剤、アルカリ性物質、還元防止剤、及びヒドロトロピー剤は、いずれも単一の化合物を使用してもよいし、それぞれ複数の化合物を併用してもよい。前処理液の総質量中における各前処理剤の混合比率は、例えば、いずれも質量基準で、糊剤が0.5~5%、炭酸水素ナトリウムが0.5~5%、メタニトロベンゼンスルホン酸ナトリウムが0~5%、尿素が1~20%、残部が水である。前処理剤のセルロース系繊維への付与は、たとえばパディング法が挙げられる。パディングの絞り率は40~90%程度が好ましく、より好ましくは60~80%程度である。 Examples of the alkaline substances include alkali metal salts of inorganic or organic acids, salts of alkaline earth metals, and compounds that liberate alkalis when heated; inorganic or organic alkali metal hydroxides and alkali Metal salts are preferred, including sodium compounds and potassium compounds. Specific examples include alkali metal hydroxides such as sodium hydroxide and calcium hydroxide, and inorganic compounds such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium dihydrogen phosphate, disodium hydrogen phosphate, and sodium phosphate. and alkali metal salts of organic compounds such as sodium formate and sodium trichloroacetate. Preferred is sodium hydrogen carbonate. As the above-mentioned reduction inhibitor, sodium metanitrobenzenesulfonate is preferable. Examples of the hydrotropic agent include ureas such as urea and dimethylurea, and preferably urea. A single compound may be used for each of the above-mentioned thickening agent, alkaline substance, reduction inhibitor, and hydrotropic agent, or a plurality of compounds may be used in combination. The mixing ratio of each pretreatment agent in the total mass of the pretreatment liquid is, for example, 0.5 to 5% of sizing agent, 0.5 to 5% of sodium bicarbonate, and 0.5 to 5% of metanitrobenzenesulfonic acid, all based on mass. Sodium is 0-5%, urea is 1-20%, and the balance is water. The pretreatment agent may be applied to the cellulose fibers by, for example, a padding method. The aperture ratio of the padding is preferably about 40 to 90%, more preferably about 60 to 80%.
上記記録メディアは、着色分散液受容層を有するものと、有さないものとに大別される。前記インクジェット記録方法に用いる記録メディアとしては、これらのいずれも好ましい。具体的な記録メディアとしては、例えば、紙、フィルム、繊維や布(ポリエステル、セルロース、ナイロン、羊毛等)、皮革、カラーフィルター用基材等が挙げられる。着色分散液受容層は、着色分散液を吸収してその乾燥を早める等の作用を目的として、記録メディアに設置される。着色分散液受容層は、例えば前記の記録メディアにカチオン系ポリマーを含浸又は塗工する方法;着色分散液中の色素を吸収できる無機微粒子を、ポリビニルアルコールやポリビニルピロリドン等の親水性ポリマーと共に、記録メディアの表面に塗工する方法;等により設置される。前記着色分散液中の色素を吸収し得る無機微粒子としては、多孔質シリカ、アルミナゾル、及び特殊セラミックス等が挙げられる。このような着色分散液受容層を有する記録メディアは、通常インクジェット専用紙、インクジェット専用フィルム、光沢紙、光沢フィルム等と呼ばれる。市販されているインクジェット専用紙としては、例えば、キヤノン株式会社製、商品名プロフェッショナルフォトペーパー等が挙げられる。また、着色分散液受容層を有さない紙としては普通紙等が挙げられる。市販されている普通紙としては、例えば、プレーンペーパーコピー(PPC)用紙等が挙げられる。 The above-mentioned recording media are roughly divided into those having a colored dispersion receiving layer and those not having a colored dispersion receiving layer. Any of these are preferable as a recording medium used in the inkjet recording method. Specific recording media include, for example, paper, film, fibers and cloth (polyester, cellulose, nylon, wool, etc.), leather, color filter substrates, and the like. The colored dispersion receiving layer is installed on the recording medium for the purpose of absorbing the colored dispersion and hastening its drying. The colored dispersion-receiving layer can be formed, for example, by impregnating or coating the recording medium with a cationic polymer; inorganic fine particles that can absorb the dye in the colored dispersion are used together with a hydrophilic polymer such as polyvinyl alcohol or polyvinylpyrrolidone for recording. It is installed by coating the surface of the media; etc. Examples of the inorganic fine particles that can absorb the dye in the colored dispersion include porous silica, alumina sol, and special ceramics. A recording medium having such a colored dispersion receiving layer is usually called inkjet paper, inkjet film, glossy paper, glossy film, or the like. Commercially available inkjet paper includes, for example, Professional Photo Paper manufactured by Canon Inc. and the like. Examples of paper without a colored dispersion receiving layer include plain paper and the like. Commercially available plain paper includes, for example, plain paper copy (PPC) paper.
上記着色分散液は、上記記録メディアのうち繊維に対しても極めて好適に記録を行うことができる。繊維の種類は特に制限されないが、疎水性繊維が好ましい。疎水性繊維としては、例えば、ポリエステル繊維、ナイロン繊維、トリアセテート繊維、ジアセテート繊維、ポリアミド繊維、及びこれらの繊維を2種類以上用いた混紡繊維等が挙げられる。また、これらの繊維とレーヨン等の再生繊維;及び、これらの繊維と、木綿、絹、及び羊毛等の天然繊維との混紡繊維も、本明細書においては疎水性繊維に含まれ、ポリエステル繊維又はポリエステル繊維を含有する混紡繊維であることが好ましい。
繊維の中には、着色分散液受容層を有するものも知られており、そのような繊維も好適に使用することができる。着色分散液受容層を有する繊維は公知の方法で調製することも、また、市販品として入手することもできる。着色分散液受容層の材質や構造等は特に限定されず、目的等に応じて適宜使用することができる。
The above-mentioned colored dispersion liquid can perform recording very suitably even on fibers among the above-mentioned recording media. The type of fiber is not particularly limited, but hydrophobic fibers are preferred. Examples of the hydrophobic fibers include polyester fibers, nylon fibers, triacetate fibers, diacetate fibers, polyamide fibers, and blended fibers using two or more of these fibers. In addition, blended fibers of these fibers and recycled fibers such as rayon; and blended fibers of these fibers and natural fibers such as cotton, silk, and wool are also included in the hydrophobic fibers in this specification, and polyester fibers or Preferably, it is a blended fiber containing polyester fiber.
Some fibers are known to have a colored dispersion receiving layer, and such fibers can also be suitably used. Fibers having a colored dispersion-receiving layer can be prepared by known methods or can be obtained commercially. The material and structure of the colored dispersion receiving layer are not particularly limited, and can be used as appropriate depending on the purpose.
上記着色分散液を、記録メディアに付着させる方法は特に制限されず、公知の全ての方法(例えば各種の筆記具、及びインクジェット記録等)を使用することができる。記録メディアとして繊維を使用するときは、サイズプレス法、コーテイング法等を含む表面塗工染色方法、又は内添染色方法等も使用できる。また、前記の化合物は昇華性を有するため、昇華転写染色方法も好ましく使用できる。 The method for attaching the colored dispersion liquid to the recording medium is not particularly limited, and all known methods (for example, various writing instruments, inkjet recording, etc.) can be used. When using fibers as a recording medium, a surface coating dyeing method including a size press method, a coating method, or an internal dyeing method can also be used. Further, since the above-mentioned compound has sublimation property, a sublimation transfer dyeing method can also be preferably used.
上記疎水性繊維の具体例としては、例えば、ポリエステル繊維、ナイロン繊維、トリアセテート繊維、ジアセテート繊維、ポリアミド繊維、及びこれらの繊維を2種類以上用いた混紡繊維等が挙げられる。また、これらとレーヨン等の再生繊維、木綿、絹、羊毛等の天然繊維との混紡繊維も、本明細書においては疎水性繊維に含まれる。これらの疎水性繊維としては、着色分散液受容層(滲み防止層)を有するものも知られており、そのような疎水性繊維も同様に含まれる。着色分散液受容層の形成方法は公知技術であり、着色分散液受容層を有する繊維も市販品として入手が可能である。着色分散液受容層の材質や構造等は、特に限定されず、目的等に応じて適宜使用することができる。上記疎水性繊維の捺染方法により得られる、染色された疎水性繊維も本願発明に含まれる。 Specific examples of the hydrophobic fibers include polyester fibers, nylon fibers, triacetate fibers, diacetate fibers, polyamide fibers, and blended fibers using two or more of these fibers. In addition, blended fibers of these with recycled fibers such as rayon, and natural fibers such as cotton, silk, and wool are also included in the hydrophobic fibers in this specification. Among these hydrophobic fibers, those having a colored dispersion receiving layer (bleeding prevention layer) are also known, and such hydrophobic fibers are also included. The method for forming the colored dispersion receiving layer is a known technique, and fibers having the colored dispersion receiving layer are also available as commercial products. The material and structure of the colored dispersion receiving layer are not particularly limited, and can be used as appropriate depending on the purpose. Dyed hydrophobic fibers obtained by the above hydrophobic fiber printing method are also included in the present invention.
上記着色分散液は、各種分野において使用することができるが、筆記用水性インク、水性印刷インク、情報記録インク、捺染等に好適であり、インクジェット捺染用インクとして用いることが特に好ましい。 The above-mentioned colored dispersion can be used in various fields, but is suitable for aqueous writing inks, aqueous printing inks, information recording inks, textile printing, etc., and is particularly preferably used as an ink for inkjet textile printing.
本発明の着色分散液は、長期間保存後の固体析出、物性変化、色変化等もなく、保存安定性に優れる。また、インクジェットプリンタヘッドへの初期充填性が良好であり、連続印刷安定性も良好である。更に、印刷後の用紙上の画像の滲みが無く鮮明な画像を得ることが可能である。これらに加え、本発明の着色分散液で染色した染色物は、染色濃度が高く、且つ均染性、耐光性に優れ、高品位な黒色の色相を有する。更に、イエロー、オレンジ、マゼンタ、シアン染料等をそれぞれ含む着色分散液と併用することにより、各種堅牢性に優れ、保存性の優れたフルカラーのインクジェット捺染が可能である。このように、本発明の着色分散液は、吐出安定性に極めて優れることから、特にインクジェット捺染インク用として好適である。特に、染色濃度の値が、下記染色濃度評価において1.39以上の数値であり、下記染色性評価において染色部分と白地部分の境界部に黄色の滲みや汚染が見られず、境界部が鮮明に再現され、下記演色性評価1において60%dutyの色差が2.1未満の数値であり、かつ、下記演色性評価2において60%dutyの色差が2.6未満の数値である場合、染色濃度が高く、染色性且つ演色性に優れた黒色となり、より良好な黒色捺染物が得られるため、着色分散液としてより優れる。 The colored dispersion of the present invention has excellent storage stability without solid precipitation, physical property changes, color changes, etc. after long-term storage. In addition, the initial filling property into the inkjet printer head is good, and the continuous printing stability is also good. Furthermore, it is possible to obtain a clear image without blurring of the image on the paper after printing. In addition to these, the dyed product dyed with the colored dispersion of the present invention has a high dyeing density, excellent level dyeing properties and light fastness, and has a high-quality black hue. Further, by using the dyes in combination with colored dispersions containing yellow, orange, magenta, cyan dyes, etc., it is possible to perform full-color inkjet printing with excellent fastness and storage stability. As described above, the colored dispersion of the present invention has extremely excellent ejection stability, and is therefore particularly suitable for use in inkjet textile printing inks. In particular, the staining density value is 1.39 or higher in the staining density evaluation below, and in the staining evaluation below, there is no yellow bleeding or staining at the boundary between the dyed area and the white background area, and the boundary area is clear. If the color difference at 60% duty is less than 2.1 in color rendering evaluation 1 below, and the color difference at 60% duty is less than 2.6 in color rendering evaluation 2 below, dyeing It has a high concentration, produces a black color with excellent dyeing properties and color rendering properties, and produces a better black printed product, making it more excellent as a colored dispersion.
以下、実施例により本発明をさらに詳細に説明するが、本発明は、実施例により限定されるものではない。実施例において特に断りがない限り、「部」は質量部を、「%」は質量%をそれぞれ意味する。
[調製例1]
[B360分散液の調製]
昇華性染料としてC.I.Disperse Blue 360 30部、上記Joncryl 678のエマルション液 60部、プロクセルGXL 0.2部、サーフィノール104PG50 0.4部、イオン交換水 24部からなる混合物を、0.2mm径ガラスビーズを用いてサンドミルにて、冷却下、約15時間分散化処理を行った。得られた液にイオン交換水 60部、Joncryl 678のエマルション液 30部を加えて染料含有量を15%に調整した後、ガラス繊維濾紙GC-50(ADVANTEC社製、フィルターの孔径0.5μm)で濾過することによりB360分散液を得た。
[調製例2]
[B359分散液の調製]
表1に記載の昇華染料に変更した以外は、調製例1と同様にしてB359分散液を得た。
[調製例3]
[Y54分散液の調製]
表1に記載の昇華染料に変更した以外は、調製例1と同様にしてY54分散液を得た。
[調製例4]
[Or25分散液の調製]
表1に記載の昇華染料に変更した以外は、調製例1と同様にしてOr25分散液を得た。
[調製例5]
[Or60分散液の調製]
表1に記載の昇華染料に変更した以外は、調製例1と同様にしてOr60分散液を得た。
[調製例6]
[Bw27分散液の調製]
表1に記載の昇華染料に変更した以外は、調製例1と同様にしてBw27分散液を得た。
[調製例7]
[R60分散液の調製]
表1に記載の昇華染料に変更した以外は、調製例1と同様にしてR60分散液を得た。
EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited by the Examples. In the examples, unless otherwise specified, "part" means part by mass, and "%" means % by mass.
[Preparation example 1]
[Preparation of B360 dispersion]
C. as a sublimable dye. I. A mixture consisting of 30 parts of Disperse Blue 360, 60 parts of the above Joncryl 678 emulsion, 0.2 parts of Proxel GXL, 0.4 parts of Surfynol 104PG50, and 24 parts of ion-exchanged water was sand milled using 0.2 mm diameter glass beads. The dispersion treatment was carried out for about 15 hours under cooling. After adjusting the dye content to 15% by adding 60 parts of ion-exchanged water and 30 parts of Joncryl 678 emulsion liquid to the obtained liquid, glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size 0.5 μm) was added. A B360 dispersion was obtained by filtration.
[Preparation example 2]
[Preparation of B359 dispersion]
A B359 dispersion was obtained in the same manner as in Preparation Example 1, except that the sublimation dye shown in Table 1 was used.
[Preparation example 3]
[Preparation of Y54 dispersion]
A Y54 dispersion was obtained in the same manner as in Preparation Example 1, except that the sublimation dye shown in Table 1 was used.
[Preparation example 4]
[Preparation of Or25 dispersion]
An Or25 dispersion was obtained in the same manner as in Preparation Example 1, except that the sublimation dye shown in Table 1 was used.
[Preparation example 5]
[Preparation of Or60 dispersion]
An Or60 dispersion was obtained in the same manner as in Preparation Example 1, except that the sublimation dye shown in Table 1 was used.
[Preparation example 6]
[Preparation of Bw27 dispersion]
A Bw27 dispersion was obtained in the same manner as in Preparation Example 1, except that the sublimation dye shown in Table 1 was used.
[Preparation Example 7]
[Preparation of R60 dispersion]
An R60 dispersion was obtained in the same manner as in Preparation Example 1, except that the sublimation dye shown in Table 1 was used.
[調製例8]
(工程1)下記式(13)で表される化合物の合成
DMF30部中に、m-クロロアニリン6.4部、炭酸カリウム13.8部、パラトルエンスルホン酸2-メトキシエチル8.0部を加えて、110℃に加熱し、6時間反応させた。60℃に冷却し、得られた反応液に水100部を加え、トルエン50部で3回抽出を行った。得られた有機層を1%塩酸水100部で3回、水100部で1回洗浄した後、エバポレーターにて、トルエンを留去し、油状物5.5部を得た。
次にDMF30部中に、得られた油状物5.5部、炭酸カリウム4.4部、ヨードエタン7.0部を加えて、110℃に加熱し、6時間反応させた。60℃に冷却し、得られた反応液に水100部を加え、トルエン50部で3回抽出を行った。得られた有機層を水100部で2回洗浄した後、エバポレーターにて、トルエンを留去し、下記式(13)で表される化合物5.5部を得た。
[Preparation example 8]
(Step 1) Synthesis of a compound represented by the following formula (13) In 30 parts of DMF, 6.4 parts of m-chloroaniline, 13.8 parts of potassium carbonate, and 8.0 parts of 2-methoxyethyl p-toluenesulfonate were added. In addition, the mixture was heated to 110°C and reacted for 6 hours. After cooling to 60° C., 100 parts of water was added to the resulting reaction solution, and extraction was performed three times with 50 parts of toluene. After washing the obtained organic layer three times with 100 parts of 1% hydrochloric acid water and once with 100 parts of water, toluene was distilled off using an evaporator to obtain 5.5 parts of an oily substance.
Next, 5.5 parts of the obtained oil, 4.4 parts of potassium carbonate, and 7.0 parts of iodoethane were added to 30 parts of DMF, heated to 110°C, and reacted for 6 hours. After cooling to 60° C., 100 parts of water was added to the resulting reaction solution, and extraction was performed three times with 50 parts of toluene. After washing the obtained organic layer twice with 100 parts of water, toluene was distilled off using an evaporator to obtain 5.5 parts of a compound represented by the following formula (13).
(工程2)下記式(14)で表される化合物の合成
氷水50部中に、p-ニトロアニリン8.2部、35%塩酸18.8部を加えて、0~10℃にて30分撹拌した。同温度にて、40%亜硝酸ナトリウム10.9部を添加し、1時間撹拌した。得られた反応液に式(13)の化合物10部を加え、pH2.0~pH2.5、0~10℃で2時間、pH3.0~pH3.5、0~10℃で2時間反応を実施した。反応終了後、濾過し、水洗することで、式(14)で表される化合物9.3部を得た。
(Step 2) Synthesis of a compound represented by the following formula (14) 8.2 parts of p-nitroaniline and 18.8 parts of 35% hydrochloric acid were added to 50 parts of ice water, and the mixture was heated at 0 to 10°C for 30 minutes. Stirred. At the same temperature, 10.9 parts of 40% sodium nitrite was added and stirred for 1 hour. 10 parts of the compound of formula (13) was added to the obtained reaction solution, and the reaction was carried out at pH 2.0 to pH 2.5, 0 to 10°C for 2 hours, and at pH 3.0 to pH 3.5, 0 to 10°C for 2 hours. carried out. After the reaction was completed, 9.3 parts of the compound represented by formula (14) was obtained by filtering and washing with water.
[調製例9]
(工程1)下記式(9)で表される化合物の合成
DMF30部中に、m-クロロアニリン6.4部、炭酸カリウム13.8部、ヨードエタン18.7部を加えて、100℃に加熱し、6時間反応させた。60℃に冷却し、得られた反応液に水100部を加え、トルエン50部で3回抽出を行った。得られた有機層を水100部で3回水洗した後、エバポレーターにて、トルエンを留去、乾燥することにより、下記式(9)で表される化合物10部を得た。
[Preparation example 9]
(Step 1) Synthesis of a compound represented by the following formula (9) 6.4 parts of m-chloroaniline, 13.8 parts of potassium carbonate, and 18.7 parts of iodoethane were added to 30 parts of DMF and heated to 100°C. and allowed to react for 6 hours. After cooling to 60° C., 100 parts of water was added to the resulting reaction solution, and extraction was performed three times with 50 parts of toluene. After washing the obtained organic layer three times with 100 parts of water, toluene was distilled off and dried using an evaporator to obtain 10 parts of a compound represented by the following formula (9).
(工程2)下記式(10)で表される化合物の合成
氷水50部中に、p-ニトロアニリン8.2部、35%塩酸18.8部を加えて、0~10℃にて30分撹拌した。同温度にて、40%亜硝酸ナトリウム10.9部を添加し、1時間撹拌した。得られた反応液に式(9)の化合物10部を加え、pH2.0~pH2.5、0~10℃で2時間、pH3.0~pH3.5、0~10℃で2時間反応を実施した。反応終了後、濾過し、水洗することで、式(10)で表される化合物15.0部を得た。
(Step 2) Synthesis of a compound represented by the following formula (10) 8.2 parts of p-nitroaniline and 18.8 parts of 35% hydrochloric acid were added to 50 parts of ice water, and the mixture was heated at 0 to 10°C for 30 minutes. Stirred. At the same temperature, 10.9 parts of 40% sodium nitrite was added and stirred for 1 hour. 10 parts of the compound of formula (9) was added to the obtained reaction solution, and the reaction was carried out at pH 2.0 to pH 2.5, 0 to 10°C for 2 hours, and at pH 3.0 to pH 3.5, 0 to 10°C for 2 hours. carried out. After the reaction was completed, 15.0 parts of the compound represented by formula (10) was obtained by filtering and washing with water.
[調製例10]
(工程1)下記式(11)で表される化合物の合成
DMF30部中に、m-ブロモアニリン8.6部、炭酸カリウム13.8部、ヨードエタン18.7部を加えて、100℃に加熱し、6時間反応させた。60℃に冷却し、得られた反応液に水100部を加え、トルエン50部で3回抽出を行った。得られた有機層を水100部で3回水洗した後、エバポレーターにて、トルエンを留去、乾燥することにより、下記式(11)で表される化合物11部を得た。
[Preparation example 10]
(Step 1) Synthesis of a compound represented by the following formula (11) 8.6 parts of m-bromoaniline, 13.8 parts of potassium carbonate, and 18.7 parts of iodoethane were added to 30 parts of DMF and heated to 100°C. and allowed to react for 6 hours. After cooling to 60° C., 100 parts of water was added to the resulting reaction solution, and extraction was performed three times with 50 parts of toluene. After washing the obtained organic layer three times with 100 parts of water, toluene was distilled off and dried using an evaporator to obtain 11 parts of a compound represented by the following formula (11).
(工程2)下記式(12)で表される化合物の合成
氷水50部中に、p-ニトロアニリン8.2部、35%塩酸18.8部を加えて、0~10℃にて30分撹拌した。同温度にて、40%亜硝酸ナトリウム10.9部を添加し、1時間撹拌した。得られた反応液に式(11)の化合物11部を加え、pH2.0~pH2.5、0~10℃で2時間、pH3.0~pH3.5、0~10℃で2時間反応を実施した。反応終了後、濾過し、水洗することで、式(12)で表される化合物14.0部を得た。
(Step 2) Synthesis of a compound represented by the following formula (12) 8.2 parts of p-nitroaniline and 18.8 parts of 35% hydrochloric acid were added to 50 parts of ice water, and the mixture was heated at 0 to 10°C for 30 minutes. Stirred. At the same temperature, 10.9 parts of 40% sodium nitrite was added and stirred for 1 hour. 11 parts of the compound of formula (11) was added to the obtained reaction solution, and the reaction was carried out at pH 2.0 to pH 2.5, 0 to 10°C for 2 hours, and at pH 3.0 to pH 3.5, 0 to 10°C for 2 hours. carried out. After the reaction was completed, 14.0 parts of the compound represented by formula (12) was obtained by filtering and washing with water.
[調製例11]
(工程1)下記式(21)で表される化合物の合成
アセトン30部中に、m-クロロアニリン12.7部、トリエチルアミン10.6部を加えて、30分撹拌した。この液に40℃以下で塩化ベンゾイル14.8部を滴下し、30~40℃で1時間反応した。反応液を氷水700部に滴下し、濾過、水洗することで、式(21)の化合物34.6部をウエットケーキとして得た。得たウエットケーキを乾燥し、式(21)の化合物22.6部を得た。
[Preparation example 11]
(Step 1) Synthesis of compound represented by the following formula (21) 12.7 parts of m-chloroaniline and 10.6 parts of triethylamine were added to 30 parts of acetone and stirred for 30 minutes. 14.8 parts of benzoyl chloride was added dropwise to this liquid at 40°C or below, and the mixture was reacted at 30 to 40°C for 1 hour. The reaction solution was added dropwise to 700 parts of ice water, filtered, and washed with water to obtain 34.6 parts of the compound of formula (21) as a wet cake. The obtained wet cake was dried to obtain 22.6 parts of the compound of formula (21).
(工程2)下記式(22)で表される化合物の合成
脱水THF90部中に、式(21)の化合物22.6部を加えて、30分撹拌した。この液に30℃以下でボラン-THF錯体(0.93mol/l)140部を1時間かけて滴下し、30~40℃で1時間、50~60℃で4時間反応した。反応液に水30部を1時間かけて滴下し、1時間撹拌した。この反応液を濃縮することで、式(22)の化合物21.2部を得た。
(Step 2) Synthesis of a compound represented by the following formula (22) 22.6 parts of the compound represented by the formula (21) was added to 90 parts of dehydrated THF and stirred for 30 minutes. To this liquid, 140 parts of borane-THF complex (0.93 mol/l) was added dropwise at 30°C or below over 1 hour, and the mixture was reacted at 30 to 40°C for 1 hour and at 50 to 60°C for 4 hours. 30 parts of water was added dropwise to the reaction solution over 1 hour, and the mixture was stirred for 1 hour. By concentrating this reaction solution, 21.2 parts of the compound of formula (22) was obtained.
(工程3)下記式(23)で表される化合物の合成
DMF70部中に、式(22)の化合物21.2部、炭酸カリウム22.7部、ヨードエタン34.7部を加えて、100℃に加熱し、6時間反応させた。60℃に冷却し、得られた反応液に水250部を加え、トルエン200部で3回抽出を行った。得られた有機層を水200部で3回水洗した後、エバポレーターにて、トルエンを留去、乾燥することにより、下記式(23)で表される化合物24.7部を得た。
(Step 3) Synthesis of compound represented by the following formula (23) 21.2 parts of the compound of formula (22), 22.7 parts of potassium carbonate, and 34.7 parts of iodoethane were added to 70 parts of DMF, and the mixture was heated to 100°C. The mixture was heated to a temperature of 100.degree. and reacted for 6 hours. After cooling to 60° C., 250 parts of water was added to the resulting reaction solution, and extraction was performed three times with 200 parts of toluene. After washing the obtained organic layer three times with 200 parts of water, toluene was distilled off and dried using an evaporator to obtain 24.7 parts of a compound represented by the following formula (23).
(工程4)下記式(24)で表される化合物の合成
氷水50部中に、p-ニトロアニリン8.2部、35%塩酸18.8部を加えて、0~10℃にて30分撹拌した。同温度にて、40%亜硝酸ナトリウム10.9部を添加し、1時間撹拌した。得られた反応液に式(23)の化合物12.3部を加え、pH2.0~pH2.5、0~10℃で2時間、pH3.0~pH3.5、0~10℃で2時間反応を実施した。反応終了後、濾過し、水洗することで、式(24)で表される化合物14.7部を得た。
(Step 4) Synthesis of compound represented by the following formula (24) 8.2 parts of p-nitroaniline and 18.8 parts of 35% hydrochloric acid were added to 50 parts of ice water, and the mixture was heated at 0 to 10°C for 30 minutes. Stirred. At the same temperature, 10.9 parts of 40% sodium nitrite was added and stirred for 1 hour. 12.3 parts of the compound of formula (23) was added to the obtained reaction solution, and the mixture was heated at pH 2.0 to pH 2.5 and 0 to 10°C for 2 hours, and then at pH 3.0 to pH 3.5 and 0 to 10°C for 2 hours. The reaction was carried out. After the reaction was completed, 14.7 parts of the compound represented by formula (24) was obtained by filtering and washing with water.
[実施例1]
[着色分散液1の調製]
上記式(1)で表される化合物である、上記式(14)で表される化合物 7.22部及び上記式(10)で表される化合物 1.5部、C.I.Disperse Blue 360を6.28部、TS-1500を4.5部、SM-57を4.5部、プロクセルGXL 0.2部、サーフィノール104PG50 0.4部、イオン交換水 75.4部からなる混合物を、0.2mm径ガラスビーズを用いてサンドミルにて、冷却下、約15時間分散化処理を行った。染料含有量は15%である。ガラス繊維濾紙GC-50(ADVANTEC社製、フィルターの孔径0.5μm)で濾過することにより着色分散液1を得た。
[実施例2~12、比較例1~5]
[着色分散液2~17の調製]
上記式(1)で表される化合物の種類及び添加量、分散剤の種類及び添加量を表2に記載の通りに変更した以外は実施例1と同様にして、着色分散液2~17を得た。
下記表2中の略号は、それぞれ以下を表わす。
B360:C.I.Disperse Blue 360
B359:C.I.Disperse Blue 359
Y54:C.I.Disperse Yellow 54
TS-1500:ポリオキシエチレンアリールフェニルエーテル系分散剤(東邦化学工業株式会社製)
SM-57:ポリオキシエチレンアリールフェニルエーテルサルフェート系分散剤(東邦化学工業株式会社製)
JC678:ジョンクリル 678 (BASFジャパン株式会社製)
[Example 1]
[Preparation of colored dispersion 1]
7.22 parts of the compound represented by the above formula (14), which is the compound represented by the above formula (1), and 1.5 parts of the compound represented by the above formula (10), C.I. I. From 6.28 parts of Disperse Blue 360, 4.5 parts of TS-1500, 4.5 parts of SM-57, 0.2 parts of Proxel GXL, 0.4 parts of Surfynol 104PG50, and 75.4 parts of ion exchange water. The mixture was subjected to a dispersion treatment using 0.2 mm diameter glass beads in a sand mill for about 15 hours under cooling. The dye content is 15%. Colored dispersion 1 was obtained by filtration through glass fiber filter paper GC-50 (manufactured by ADVANTEC, filter pore size 0.5 μm).
[Examples 2 to 12, Comparative Examples 1 to 5]
[Preparation of colored dispersions 2 to 17]
Colored dispersions 2 to 17 were prepared in the same manner as in Example 1, except that the type and amount of the compound represented by the above formula (1) and the type and amount of the dispersant were changed as shown in Table 2. Obtained.
The abbreviations in Table 2 below represent the following, respectively.
B360:C. I. Disperse Blue 360
B359:C. I. Disperse Blue 359
Y54:C. I. Disperse Yellow 54
TS-1500: Polyoxyethylene arylphenyl ether dispersant (manufactured by Toho Chemical Industry Co., Ltd.)
SM-57: Polyoxyethylene arylphenyl ether sulfate dispersant (manufactured by Toho Chemical Industry Co., Ltd.)
JC678: Jonkryl 678 (manufactured by BASF Japan Co., Ltd.)
[インクの調製]
[実施例13]
上記実施例1で得た着色分散液1を43部、上記調製例2で得たB359分散液を6部、上記調製例3で得たY54分散液を6部、を混合し、ここへ、グリセリンを15部、プロピレングリコールを10部、プロクセルGXL(ロンザ社製)を0.1部、BYK-348(ビックケミージャパン製)を0.8部、TEA-80(純正化学株式会社製)を0.1部、メトキシグリコールを10.0部、イオン交換水14.0部を加えて撹拌した後、5μmのフィルターにより濾過して、実施例13のインク1を得た。調製に用いた各分散液の組成について下記表2に記載した。
[実施例14~24、比較例2~8]
着色分散液の種類及び添加量を表3に記載の通りに変更した以外は実施例13と同様にして、インク2~16を得た。
[Preparation of ink]
[Example 13]
43 parts of the colored dispersion 1 obtained in the above Example 1, 6 parts of the B359 dispersion obtained in the above Preparation Example 2, and 6 parts of the Y54 dispersion obtained in the above Preparation Example 3 were mixed, and hereto, 15 parts of glycerin, 10 parts of propylene glycol, 0.1 part of Proxel GXL (manufactured by Lonza), 0.8 part of BYK-348 (manufactured by BYK Chemie Japan), and TEA-80 (manufactured by Junsei Kagaku Co., Ltd.). After adding and stirring 0.1 part of methoxy glycol, 10.0 parts of methoxy glycol, and 14.0 parts of ion-exchanged water, the mixture was filtered through a 5 μm filter to obtain Ink 1 of Example 13. The composition of each dispersion used in the preparation is listed in Table 2 below.
[Examples 14 to 24, Comparative Examples 2 to 8]
Inks 2 to 16 were obtained in the same manner as in Example 13, except that the type and amount of the colored dispersion liquid added were changed as shown in Table 3.
上記のようにして調製した各着色分散液、インクを用いて、以下の各評価試験を行った。結果を上記表2中、及び3中に示す。 The following evaluation tests were conducted using each of the colored dispersions and inks prepared as described above. The results are shown in Tables 2 and 3 above.
[着色分散液で印刷した中間記録媒体とそれを用いた昇華転写捺染]
調製した各インクを、インクジェットプリンタ(EPSON株式会社製、商品名PX-504A)に充填し、中間記録媒体としてTRANSJET Eco II 8385(95g/m2)を用いて、100%Dutyあるいは25%Dutyの単色ベタ画像を印刷した中間記録媒体をそれぞれ得た。得られた各中間記録媒体のインク付着面とポリエステル布(帝人トロピカル)とを重ね合わせた後、卓上自動平プレス機(アサヒ繊維機械株式会社製:AF-65TEN)を用いて200℃×30秒の条件にて熱処理することによって、昇華転写染色方法により染色された染色物をそれぞれ得た。得られた各染色物について、下記の評価を行った。
[Intermediate recording medium printed with colored dispersion and sublimation transfer printing using it]
Each of the prepared inks was filled into an inkjet printer (manufactured by EPSON Corporation, trade name PX-504A) and printed at 100% duty or 25% duty using TRANSJET Eco II 8385 (95 g/m 2 ) as an intermediate recording medium. Intermediate recording media on which monochrome solid images were printed were obtained. After overlapping the ink-attached surface of each intermediate recording medium obtained with a polyester cloth (Teijin Tropical), it was heated at 200°C for 30 seconds using a tabletop automatic flat press (AF-65TEN, manufactured by Asahi Textile Machinery Co., Ltd.). By heat-treating under the following conditions, dyed products dyed by the sublimation transfer dyeing method were obtained. Each of the obtained dyed products was evaluated as follows.
[演色性1:D65光源とF2光源の色差]
分光測色計「eXact(X-rite社製)」を用いて、200℃×30秒の条件にて熱処理することによって、昇華転写染色方法により染色された25%Dutyの単色ベタの各染色物の色相L*a*b*を測定した。測色は視野角2°、ステータスIの条件を使用して、D65光源とF2光源における各L*a*b*の値を得た。得られた各光源のL*a*b*の値から色差△ED65-F2を下記(式1)から求め、以下の評価基準に従って評価した。
評価結果を上記表3に示す。
△ED65-F2=[(L*
D65-L*
F2)2+(a*
D65-a*
F2)2+(b*
D65-b*
F2)2]1/2 (式1)
[評価基準]
A:色差△ED65-F2が1.0以上4.5未満。
B:色差△ED65-F2が4.5以上5.0未満。
C:色差△ED65-F2が5.0以上。
[演色性2:D65光源とA光源の色差]
分光測色計「eXact(X-rite社製)」を用いて、200℃×30秒の条件にて熱処理することによって、昇華転写染色方法により染色された25%Dutyの単色ベタの各染色物の色相L*a*b*を測定した。測色は視野角2°、ステータスIの条件を使用して、D65光源とA光源における各L*a*b*の値を得た。得られた各光源のL*a*b*の値から色差△ED65-Aを下記(式2)から求め、以下の評価基準に従って評価した。
評価結果を上記表3に示す。
△ED65-A=[(L*
D65-L*
A)2+(a*
D65-a*
A)2+(b*
D65-b*
A)2]1/2 (式2)
[評価基準]
A:色差△ED65-Aが1.0以上3.5未満。
B:色差△ED65-Aが3.5以上4.0未満。
C:色差△ED65-Aが4.0以上。
[発色性:シグマK/S値]
分光測色計「eXact(X-rite社製)」を用いて、200℃×30秒の条件にて熱処理することによって、昇華転写染色方法により染色された100%Dutyの単色ベタの各染色物の染色濃度を測定した。測色はD65光源、視野角2°、ステータスIの条件で行った。各染色布の400~700nmにおける反射率Rラムダを測色し、Kubelka-Munkの式:K/S=(1-Rラムダ)2/2RラムダによりK/S値を算出した。そして、各波長におけるK/S値の合計であるシグマK/S値を算出し、以下の基準で染色濃度を評価した。シグマK/S値が大きい方が、染色濃度が高いことを示すため、品質が優れる。
評価結果を上記表3に示す。
[評価基準]
A:シグマK/S値が470以上
B:シグマK/S値が450以上470未満
C:シグマK/S値が430以上450未満
[Color rendering property 1: Color difference between D65 light source and F2 light source]
Each monochromatic solid dyed product with a duty of 25% was dyed by the sublimation transfer dyeing method using a spectrophotometer “eXact (manufactured by X-rite)” and heat-treated at 200°C for 30 seconds. The hue L*a*b* was measured. The colorimetry was performed using conditions of a viewing angle of 2° and status I, and the values of L * a * b * were obtained for the D65 light source and the F2 light source. The color difference ΔE D65-F2 was determined from the obtained value of L * a * b * of each light source using the following (Formula 1), and evaluated according to the following evaluation criteria.
The evaluation results are shown in Table 3 above.
△E D65-F2 = [(L * D65 - L * F2 ) 2 + (a * D65 - a * F2 ) 2 + (b * D65 - b * F2 ) 2 ] 1/2 (Formula 1)
[Evaluation criteria]
A: Color difference ΔE D65-F2 is 1.0 or more and less than 4.5.
B: Color difference ΔE D65-F2 is 4.5 or more and less than 5.0.
C: Color difference △E D65-F2 is 5.0 or more.
[Color rendering property 2: Color difference between D65 light source and A light source]
Each monochromatic solid dyed product with a duty of 25% was dyed by the sublimation transfer dyeing method using a spectrophotometer “eXact (manufactured by X-rite)” and heat-treated at 200°C for 30 seconds. The hue L*a*b* was measured. Color measurement was performed using conditions of a viewing angle of 2° and status I, and the values of each L * a * b * were obtained for the D65 light source and the A light source. The color difference ΔE D65-A was determined from the obtained value of L * a * b * of each light source using the following (Formula 2), and evaluated according to the following evaluation criteria.
The evaluation results are shown in Table 3 above.
△E D65-A = [(L * D65 - L * A ) 2 + (a * D65 - a * A ) 2 + (b * D65 - b * A ) 2 ] 1/2 (Formula 2)
[Evaluation criteria]
A: Color difference ΔE D65-A is 1.0 or more and less than 3.5.
B: Color difference ΔE D65-A is 3.5 or more and less than 4.0.
C: Color difference ΔE D65-A is 4.0 or more.
[Color development: Sigma K/S value]
100% duty single color solid dyed items dyed by sublimation transfer dyeing method by heat treatment at 200°C x 30 seconds using spectrophotometer “eXact (manufactured by X-rite)” The staining density was measured. Colorimetry was performed under the conditions of a D65 light source, a viewing angle of 2°, and status I. The reflectance R lambda of each dyed cloth at 400 to 700 nm was measured, and the K/S value was calculated using the Kubelka-Munk formula: K/S=(1-R lambda)2/2R lambda. Then, the sigma K/S value, which is the sum of the K/S values at each wavelength, was calculated, and the staining density was evaluated based on the following criteria. The larger the sigma K/S value, the higher the staining density, and therefore the better the quality.
The evaluation results are shown in Table 3 above.
[Evaluation criteria]
A: Sigma K/S value is 470 or more B: Sigma K/S value is 450 or more and less than 470 C: Sigma K/S value is 430 or more and less than 450
[再分散性]
上記各実施例、及び比較例の着色分散液、インクをそれぞれガラスシャーレの上に25μLの滴下のせ、60℃の恒温恒湿機で1時間乾燥させた。
乾燥後、室温で10mLのイオン交換水を滴下し、再分散するか否かを目視にて観察し、下記4段階の基準で評価した。
残渣が無くあるいは少なく再分散するインクほど、乾燥後の目詰まりを解消し易いため優れている。A、B又はCの場合、再分散性は良好と、Dの場合、不良と評価した。
評価結果を上記表2、3に示す。
[評価基準]
A:残渣無く、全てが再分散した。
B:残渣が少し残るが、ほとんどが再分散している。
C:残渣は多く残るが、多少再分散している。
D:まったく再分散しない。
[Redispersibility]
25 μL of each of the colored dispersions and inks of the above Examples and Comparative Examples were placed dropwise on a glass petri dish, and dried in a constant temperature and humidity machine at 60° C. for 1 hour.
After drying, 10 mL of ion-exchanged water was added dropwise at room temperature, and whether re-dispersion occurred was visually observed and evaluated using the following 4-level criteria.
An ink that can be redispersed without or with less residue is better because it is easier to eliminate clogging after drying. In the case of A, B or C, the redispersibility was evaluated as good, and in the case of D, it was evaluated as poor.
The evaluation results are shown in Tables 2 and 3 above.
[Evaluation criteria]
A: Everything was redispersed without any residue.
B: Some residue remains, but most of it has been redispersed.
C: A lot of residue remains, but it has been redispersed to some extent.
D: Not redispersed at all.
[粒度変化]
60℃で5日間保存した各着色分散液中の粒子のメディアン径(D50、数平均粒子径)をMICRO TRAC UPA EX150(マイクロトラックベル株式会社製)を用いて測定した。以下の基準で評価した。A又はB又はCの場合、保存安定性は良好と、Dの場合、不良と評価した。
評価結果を上記表2に示す。
[評価基準]
A:D50が140nm未満
B:D50が140nm以上160nm未満
C:D50が160nm以上170nm未満
D:D50が170nm以上
[Particle size change]
The median diameter (D50, number average particle diameter) of particles in each colored dispersion that was stored at 60° C. for 5 days was measured using MICRO TRAC UPA EX150 (manufactured by Micro Track Bell Co., Ltd.). Evaluation was made based on the following criteria. In the case of A, B, or C, the storage stability was evaluated as good, and in the case of D, it was evaluated as poor.
The evaluation results are shown in Table 2 above.
[Evaluation criteria]
A: D50 is less than 140 nm B: D50 is 140 nm or more and less than 160 nm C: D50 is 160 nm or more and less than 170 nm D: D50 is 170 nm or more
上記表2及び3の結果から明らかなように、実施例1~12の着色分散液は比較例1~5の着色分散液に対し、粒度変化が小さく保存安定性が良好であった。また、実施例1~12の着色分散液を用いた実施例13~24のインクは、比較例1~5の着色分散液を用いた比較例6~9に比べ、粒度変化が小さく保存安定性が良好で、なおかつ演色性と発色性も高く、高品位の黒色を示していることが分かる。また、本発明に係る式(1)で表される染料を含む着色分散液は、再分散性及び射出性に優れ、転写効率が高く、染色濃度が高い優れた色調の染色物が得られることから、各種記録用インク、特にインクジェット捺染用インクとして極めて有用であることを示している。 As is clear from the results in Tables 2 and 3 above, the colored dispersions of Examples 1 to 12 had smaller particle size changes and better storage stability than the colored dispersions of Comparative Examples 1 to 5. In addition, the inks of Examples 13 to 24 using the colored dispersions of Examples 1 to 12 had smaller particle size changes and had better storage stability than Comparative Examples 6 to 9, which used the colored dispersions of Comparative Examples 1 to 5. It can be seen that the color is good, the color rendering property and the color development are also high, and a high quality black color is exhibited. In addition, the colored dispersion containing the dye represented by formula (1) according to the present invention has excellent redispersibility and injection properties, has high transfer efficiency, and can provide dyed products with high dye density and excellent tone. This shows that the ink is extremely useful as various recording inks, especially inkjet textile inks.
本発明の着色分散液は、保存安定性が良好で、昇華転写効率が高く、高い染色濃度が得られる。また、演色性にも優れる染色物を得ることがき、各種捺染用インク、特にインクジェット捺染用インクとして要求される印刷適性を保つ事ができるため、とりわけ昇華転写用インクジェット捺染用ブラックインクとして極めて有用である。 The colored dispersion of the present invention has good storage stability, high sublimation transfer efficiency, and high dye density. In addition, it is possible to obtain dyed products with excellent color rendering properties, and it is possible to maintain the printability required for various textile printing inks, especially inkjet textile printing inks, so it is extremely useful as a black ink for sublimation transfer inkjet textile printing. be.
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JP2015010212A (en) | 2013-07-01 | 2015-01-19 | セイコーエプソン株式会社 | Ink for sublimation transfer |
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JP2019188368A (en) | 2018-04-27 | 2019-10-31 | 日信化学工業株式会社 | Dispersant, dispersion and ink composition, and method for producing the same |
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