WO2023281936A1 - Water-insoluble pigment composition - Google Patents
Water-insoluble pigment composition Download PDFInfo
- Publication number
- WO2023281936A1 WO2023281936A1 PCT/JP2022/021893 JP2022021893W WO2023281936A1 WO 2023281936 A1 WO2023281936 A1 WO 2023281936A1 JP 2022021893 W JP2022021893 W JP 2022021893W WO 2023281936 A1 WO2023281936 A1 WO 2023281936A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- water
- phycocyanin
- insoluble
- carrageenan
- resins
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 87
- 239000000049 pigment Substances 0.000 title claims abstract description 44
- 108010053210 Phycocyanin Proteins 0.000 claims abstract description 83
- 239000000679 carrageenan Substances 0.000 claims abstract description 44
- 229920001525 carrageenan Polymers 0.000 claims abstract description 44
- 229940113118 carrageenan Drugs 0.000 claims abstract description 44
- 235000010418 carrageenan Nutrition 0.000 claims abstract description 32
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims abstract description 32
- 239000000975 dye Substances 0.000 claims description 44
- 239000000976 ink Substances 0.000 claims description 36
- 239000002537 cosmetic Substances 0.000 claims description 30
- 241000192700 Cyanobacteria Species 0.000 claims description 20
- 238000007639 printing Methods 0.000 claims description 14
- 239000003973 paint Substances 0.000 claims description 10
- 229920003023 plastic Polymers 0.000 claims description 7
- 239000004033 plastic Substances 0.000 claims description 7
- 240000002900 Arthrospira platensis Species 0.000 claims description 6
- 235000016425 Arthrospira platensis Nutrition 0.000 claims description 6
- 239000003086 colorant Substances 0.000 claims description 6
- 229940082787 spirulina Drugs 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 32
- 229920005989 resin Polymers 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- 239000007864 aqueous solution Substances 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 238000007645 offset printing Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000011161 development Methods 0.000 description 9
- 230000018109 developmental process Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229920005992 thermoplastic resin Polymers 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- -1 for example Chemical compound 0.000 description 4
- 239000012760 heat stabilizer Substances 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 3
- NNMALANKTSRILL-ZUTFDUMMSA-N 3-[(2z,5z)-2-[[3-(2-carboxyethyl)-5-[(z)-[(3z,4r)-3-ethylidene-4-methyl-5-oxopyrrolidin-2-ylidene]methyl]-4-methyl-1h-pyrrol-2-yl]methylidene]-5-[(4-ethyl-3-methyl-5-oxopyrrol-2-yl)methylidene]-4-methylpyrrol-3-yl]propanoic acid Chemical compound O=C1C(CC)=C(C)C(\C=C/2C(=C(CCC(O)=O)C(=C/C3=C(C(C)=C(\C=C/4\C(\[C@@H](C)C(=O)N\4)=C/C)N3)CCC(O)=O)/N\2)C)=N1 NNMALANKTSRILL-ZUTFDUMMSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 241000195493 Cryptophyta Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- INPDFIMLLXXDOQ-UHFFFAOYSA-N Phycocyanobilin Natural products CCC1=C(C)C(=CC2=NC(=C/c3[nH]c(C=C/4C(C(C(N4)=O)C)=CC)c(C)c3CCC(=O)O)C(=C2C)CCC(=O)O)NC1=O INPDFIMLLXXDOQ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002156 adsorbate Substances 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 3
- 239000001055 blue pigment Substances 0.000 description 3
- 239000008406 cosmetic ingredient Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 108010072011 phycocyanobilin Proteins 0.000 description 3
- 229920006122 polyamide resin Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 241001495180 Arthrospira Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000206572 Rhodophyta Species 0.000 description 2
- 241000192584 Synechocystis Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- ZNOZWUKQPJXOIG-XSBHQQIPSA-L [(2r,3s,4r,5r,6s)-6-[[(1r,3s,4r,5r,8s)-3,4-dihydroxy-2,6-dioxabicyclo[3.2.1]octan-8-yl]oxy]-4-[[(1r,3r,4r,5r,8s)-8-[(2s,3r,4r,5r,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-sulfonatooxyoxan-2-yl]oxy-4-hydroxy-2,6-dioxabicyclo[3.2.1]octan-3-yl]oxy]-5-hydroxy-2-( Chemical compound O[C@@H]1[C@@H](O)[C@@H](OS([O-])(=O)=O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H]2OC[C@H]1O[C@H](O[C@H]1[C@H]([C@@H](CO)O[C@@H](O[C@@H]3[C@@H]4OC[C@H]3O[C@H](O)[C@@H]4O)[C@@H]1O)OS([O-])(=O)=O)[C@@H]2O ZNOZWUKQPJXOIG-XSBHQQIPSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 210000000987 immune system Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003002 pH adjusting agent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 2
- 229940038773 trisodium citrate Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- IBZYPBGPOGJMBF-UHFFFAOYSA-N 3,6 anhydrogalactose Natural products CCC=CCC1C(CC(=O)NC(C(C)CC)C(O)=O)CCC1=O IBZYPBGPOGJMBF-UHFFFAOYSA-N 0.000 description 1
- WZYRMLAWNVOIEX-BGPJRJDNSA-N 3,6-anhydro-D-galactose Chemical compound O=C[C@H](O)[C@H]1OC[C@@H](O)[C@@H]1O WZYRMLAWNVOIEX-BGPJRJDNSA-N 0.000 description 1
- DCQFFOLNJVGHLW-UHFFFAOYSA-N 4'-Me ether-Punctatin+ Natural products O1C(O)C(O)C2OCC1C2O DCQFFOLNJVGHLW-UHFFFAOYSA-N 0.000 description 1
- 241001237961 Amanita rubescens Species 0.000 description 1
- 241000192542 Anabaena Species 0.000 description 1
- 241000192660 Aphanizomenon Species 0.000 description 1
- 241000192705 Aphanothece Species 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 241000192656 Nostoc Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000179979 Pleurocapsa Species 0.000 description 1
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 241000192707 Synechococcus Species 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 241000157473 Tolypothrix Species 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940061720 alpha hydroxy acid Drugs 0.000 description 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
- 150000004716 alpha keto acids Chemical class 0.000 description 1
- YNCDEEFMDXHURQ-UHFFFAOYSA-N aluminum;ethyl 3-oxobutanoate Chemical compound [Al].CCOC(=O)CC(C)=O YNCDEEFMDXHURQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003255 anti-acne Effects 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000003926 antimycobacterial agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000013040 bath agent Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000000038 blue colorant Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- WZYRMLAWNVOIEX-UHFFFAOYSA-N cinnamtannin B-2 Natural products O=CC(O)C1OCC(O)C1O WZYRMLAWNVOIEX-UHFFFAOYSA-N 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 239000000118 hair dye Substances 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
- 230000003054 hormonal effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002065 hypopigmenting effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 239000003410 keratolytic agent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000006247 magnetic powder Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000011252 protective cream Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000001062 red colorant Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000001060 yellow colorant Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
Definitions
- the present invention relates to a water-insoluble dye composition.
- Phycocyanin an algae pigment
- Phycocyanin pigments are protein-binding pigments and are known to be extractable from blue-green algae such as Spirulina.
- Phycocyanin is a pigment that exhibits a vivid blue color, and there are high expectations in the market as a sustainable pigment.
- phycocyanin is a protein-bound pigment, so it is water-soluble, and has the problem of elution in water and the resulting color fading.
- Patent Document 1 studies have been reported on improving the thermal stability of phycocyanin, but studies on making phycocyanin non-water-soluble have not yet been reported. For this reason, phycocyanin has been used only in very limited applications.
- An object of the present invention is to provide a water-insoluble pigment composition in which phycocyanin is water-insoluble.
- a water-insoluble pigment composition comprising a complex of phycocyanin and carrageenan.
- the water-insoluble pigment composition according to [1], wherein the composition ratio of the phycocyanin and the carrageenan in the water-insoluble pigment composition is 100:1 to 100:75 by weight.
- the water-insoluble dye composition is a composition for foods, cosmetics, pharmaceuticals, stationery, writing parts, printing inks, inkjet inks, paints, plastic colorants, or toners [1] to [4] ]
- the water-insoluble dye composition according to any one of the above.
- the water-insoluble pigment composition of the present invention is a composite of phycocyanin and carrageenan.
- water-insoluble means that the solubility in water at 25° C. is less than 1% by mass.
- the water-insoluble pigment composition of the present invention has a vivid blue color and does not dissolve phycocyanin into water. It is presumed that the reason why phycocyanin does not dissolve in water is that the chemical bond with carrageenan inhibits the dissolution of phycocyanin in water. Therefore, in the water-insoluble pigment composition of the present invention, phycocyanin and carrageenan are presumed to be chemically bonded. More specifically, it is presumed that the NH group of phycocyanobilin in phycocyanin and/or the basic amino group in phycocyanin are chemically bonded to the sulfate group in carrageenan. That is, the term "complexed" as used herein means a state in which phycocyanin and carrageenan are chemically bonded.
- composition ratio of phycocyanin and carrageenan (phycocyanin: carrageenan) in the water-insoluble pigment composition of the present invention is preferably 100: 1 to 100: 100, more preferably 100: 1 to 100: 75. is more preferred, 100:3 to 100:75 is even more preferred, and 100:3 to 100:50 is particularly preferred.
- 100: 1 to 100: 100 is preferably 100: 1 to 100: 100, more preferably 100: 1 to 100: 75. is more preferred, 100:3 to 100:75 is even more preferred, and 100:3 to 100:50 is particularly preferred.
- the average particle size of the water-insoluble dye composition is not particularly limited, it is preferably 0.01 to 100 ⁇ m, more preferably 0.05 to 50 ⁇ m, from the viewpoint of color development and hiding properties during ink formation. is more preferable, and 0.1 to 20 ⁇ m is even more preferable.
- the average particle size of the water-insoluble dye composition is the arithmetic average value obtained by photographing particles with a transmission or scanning electron microscope or the like and measuring the longest diameter of 20 particles.
- Phycocyanin is a protein-bound pigment and has phycocyanobilin as its chromophore. Phycocyanin has a structure in which phycocyanobilin and protein are bound together.
- the origin of phycocyanin according to this embodiment is not particularly limited.
- phycocyanin derived from algae such as phycocyanin derived from cyanobacteria, phycocyanin derived from red algae, and phycocyanin derived from cryptophytes can be used.
- phycocyanin derived from blue-green algae is preferably used as phycocyanin from the viewpoint of being able to be collected in large amounts.
- Phycocyanin may be used individually by 1 type, and may be used in combination of 2 or more type.
- blue-green algae in phycocyanin derived from blue-green algae examples include the genus Spirulina, the genus Arthrospira, the genus Aphanizomenon, the genus Fisherella, the genus Anabaena, the genus Nostoc, and the genus Synechocystis. Synechocystis genus, Synechococcus genus, Tolypothrix genus, Aphanothece genus, Mastigoclaus genus, Pleurocapsa genus, and the like.
- cyanobacteria belonging to the genus Spirulina and the genus Arthrospira are preferable, and cyanobacteria belonging to the genus Spirulina are more preferable, because they are produced on an industrial scale and their safety has been confirmed.
- Phycocyanin can be prepared, for example, by suspending cyanobacteria in water or a buffer solution such as a phosphate buffer or a citrate buffer and extracting phycocyanin in the cyanobacteria.
- the blue-green algae used in preparing phycocyanin may be fresh blue-green algae or dried blue-green algae.
- raw blue-green algae may be dried according to a conventional method, or commercially available dried products may be used.
- the method for extracting phycocyanin is not particularly limited, and it can be extracted according to a conventional method.
- a method for extracting phycocyanin for example, the method described in JP-A-2006-230272 can be suitably used.
- An example of the extraction method is shown below.
- an extract is obtained by extracting phycocyanin in blue-green algae into an aqueous suspension.
- a calcium salt and a phosphate are reacted in the extract to produce calcium phosphate, and impurities of phycocyanin are adsorbed to the calcium phosphate to obtain an adsorbate.
- Phycocyanin is prepared by removing cyanobacterial residues and adsorbates from the extract.
- Phycocyanin can be prepared by the extraction method or the like described above. may Incidentally, as described in JP-A-11-299450, trehalose is used to improve thermal stability, and citric acid is used as a pH adjuster.
- Carrageenan is a natural high-molecular substance extracted and purified from red algae and seaweed, and is a polysaccharide having a molecular weight of 100,000 to 500,000 and mainly composed of galactose and 3,6-anhydrogalactose.
- carrageenan for example, ⁇ -carrageenan, ⁇ -carrageenan, ⁇ -carrageenan, ⁇ -carrageenan, ⁇ -carrageenan, ⁇ -carrageenan, ⁇ -carrageenan, ⁇ -carrageenan and the like are known. Structural differences between the types are classified according to the six-membered ring structure of the galactose skeleton and the conformations of the sulfate group and hydroxyl group present in the galactose skeleton.
- carrageenan can be used as the carrageenan according to the present embodiment, but it is preferably selected from at least one selected from the group consisting of ⁇ -carrageenan, ⁇ -carrageenan, and ⁇ -carrageenan. Among these, ⁇ -carrageenan is preferable from the viewpoint of having a large content of sulfate groups. Carrageenan may be used alone or in combination of two or more.
- the water-insoluble dye composition of the present invention contains organic pigments, inorganic pigments, dyes, pigments, etc., as necessary, in order to satisfy the desired desired hue within a range that does not impair the effects of the present invention. You may let
- the water-insoluble dye composition of the present invention may optionally contain other additives such as heat stabilizers and light stabilizers in order to further impart light resistance, heat resistance, etc., to the effect of the present invention.
- a heat stabilizer for example, a phenol-based antioxidant, a phosphorus-based heat stabilizer, a sulfite-silicone heat stabilizer, etc. can be used in the range of 0.001 to 1% by mass.
- light stabilizers examples include benzophenone-based UV absorbers, salicylic acid ester-based UV absorbers, triazine-based UV absorbers, benzotriazole-based UV absorbers, hindered amine-based light stabilizers, and the like, usually in an amount of 0.001 to 1% by mass. Can be used within range.
- the method for producing the water-insoluble pigment composition according to the present embodiment is not particularly limited, but the method of mixing phycocyanin and carrageenan in a solvent can produce a uniform water-insoluble pigment composition.
- the solvent may be an aqueous solvent, preferably water, but a mixture of water and a solvent such as ethanol, isopropanol, or acetone may also be used.
- a method for producing a water-insoluble dye composition by mixing each component in a solvent, for example, 1) prepare an aqueous solution or aqueous dispersion of carrageenan. 2) Meanwhile, phycocyanin is dissolved in water to prepare an aqueous solution of phycocyanin. 3) Mix the above two liquids to prepare a water-insoluble dye composition. 4) A method of filtering and drying the mixed liquid containing the obtained water-insoluble dye composition, and the like.
- Phycocyanin, carrageenan and water can be mixed in any order.
- an aqueous dispersion or aqueous solution of carrageenan may be mixed with an aqueous solution of phycocyanin, or vice versa.
- the solid content concentration of the aqueous solution of phycocyanin is not particularly limited as long as the composition ratio of phycocyanin and carrageenan in the water-insoluble pigment composition is within the range described above.
- the solid content concentration of the aqueous solution of phycocyanin may be appropriately set in consideration of handling, productivity, etc., but it is preferably 0.1 to 40% by mass, more preferably 1 to 30% by mass, based on the total amount of the aqueous solution. is preferably
- the solid content concentration of the carrageenan aqueous solution or aqueous dispersion is also not particularly limited as long as the composition ratio of phycocyanin and carrageenan in the water-insoluble pigment composition is within the range described above.
- the solid content concentration of the carrageenan aqueous solution or aqueous dispersion may be appropriately set in consideration of handling, productivity, etc., but it should be 0.01 to 10% by mass based on the total amount of the aqueous solution or aqueous dispersion. is preferred, preferably 0.1 to 7% by mass.
- Phycocyanin and carrageenan may be added in powder form and mixed.
- carrageenan powder may be added to an aqueous solution of phycocyanin and mixed, or phycocyanin powder may be added to an aqueous solution or dispersion of carrageenan and mixed.
- water may be added and mixed.
- the mixing temperature is not particularly limited, and the mixture may be mixed at room temperature or under heating. Considering the decomposition temperature of phycocyanin, the mixing temperature is preferably 10 to 60°C, more preferably 20 to 50°C.
- the mixing time is not particularly limited, and is preferably 10 minutes to 3 hours, more preferably 30 minutes to 2 hours.
- the pH range for mixing is not particularly limited, but if the pH of the phycocyanin aqueous solution is less than 4.2, phycocyanin may turn green and precipitate. 5 is more preferred, and 6.3 to 7.0 is even more preferred.
- the pH adjuster is not particularly limited, and examples thereof include hydrochloric acid, citric acid, acetic acid, lactic acid and the like.
- the mixed liquid containing the water-insoluble dye composition obtained as described above can be filtered and dried to obtain the water-insoluble dye composition.
- the mixed solution is filtered through a filter such as Nutsche, and the wet cake is repeatedly washed with water. Immediately after the start of washing with water, the filtrate is colored, but as the washing with water is repeated, the coloring of the filtrate gradually becomes lighter and finally becomes colorless and transparent. Since the wet cake remains colored even after the filtrate is no longer colored, it can be confirmed that phycocyanin and carrageenan are combined.
- the obtained water-insoluble wet cake of the water-insoluble dye composition can be dried by vacuum drying or the like to obtain a dry water-insoluble dye composition.
- the drying method and dryer are not limited as long as they are ordinary methods and ordinary devices.
- the water-insoluble dye composition of the present invention is a wet cake containing water or a dry composition, it can be used properly depending on the application.
- the wet cake can be used as it is, and when used for liquid agent dispersions, the water-based system can be replaced with a solvent-based system.
- the dry composition can be used as it is, or can be used after being redispersed in water, an organic solvent, a resin solution, or the like.
- phycocyanin which has been limited to food and cosmetic applications as a blue pigment, can be used as a coloring material equivalent to ordinary pigments in foods, cosmetics, pharmaceuticals, stationery, and writing parts. , printing inks, inkjet inks, paints, plastic colorants, or toners. Further, along with the insolubilization, it can be expected to improve properties such as heat resistance and light resistance.
- the uses of the water-insoluble dye composition of the present invention are not limited to the uses described above. An example of application is described below.
- the water-insoluble dye composition of the present invention can be used for printing inks and paints.
- the applications and compositions of printing inks and paints are described below, but are not limited to these.
- the water-insoluble dye composition of the present invention may be dispersed only in a thermoplastic resin, but it can also be dispersed in a printing ink vehicle or paint vehicle containing a thermoplastic resin as an essential component.
- thermoplastic resins include resins such as polyester resins, polyamide resins, styrene resins, acrylic resins, polyolefins, polyalkylene terephthalates, and polyvinyl chloride resins.
- Vehicles for lithographic offset printing inks include, for example, 20 to 50% by mass of resins such as rosin-modified phenolic resins, petroleum resins and alkyd resins, 0 to 30% by mass of animal and vegetable fats such as linseed oil, tung oil and soybean fat, n-paraffin, It can be produced using 10 to 60% by mass of solvents such as isoparaffins, naphthenes, ⁇ -olefins, and aromatics, and several mass% of additives such as solubilizers and gelling agents as raw materials.
- resins such as rosin-modified phenolic resins, petroleum resins and alkyd resins
- animal and vegetable fats such as linseed oil, tung oil and soybean fat, n-paraffin
- solvents such as isoparaffins, naphthenes, ⁇ -olefins, and aromatics
- additives such as solubilizers and gelling agents as raw materials.
- Vehicles for gravure printing inks and flexographic printing inks include, for example, rosins, maleic acid resins, polyamide resins, vinyl resins, cyclized rubbers, chlorinated rubbers, ethylene-vinyl acetate copolymer resins, urethane resins, polyester resins, alkyd resins, Manufactured using 10 to 50% by mass of one or more resins selected from nitrocellulose, cellulose acetate, etc., and 30 to 80% by mass of solvents such as alcohols, toluene, n-hexane, ethyl acetate, cellosolve, and butyl cellosolve as raw materials. be able to.
- solvents such as alcohols, toluene, n-hexane, ethyl acetate, cellosolve, and butyl cellosolve as raw materials.
- Vehicles for paints include, for example, alkyd resins, epoxy resins, acrylic resins, polyurethane resins, polyester resins, melamine resins, urea resins, water-soluble resins, etc., in an amount of 20 to 80% by mass, hydrocarbons, alcohols, ketones, It can be produced using a raw material containing 10 to 60% by mass of a solvent such as water.
- the content of the water-insoluble dye composition in the printing ink or paint is not particularly limited, and may be set appropriately according to the purpose.
- the content of the water-insoluble dye composition in printing inks and paints is usually 1 to 50% by mass, preferably 10 to 25% by mass.
- the water-insoluble dye composition of the present invention can be used for cosmetics.
- the cosmetics may be any kind of cosmetics as long as they can express the effects of the water-insoluble pigment composition of the present invention.
- the dosage form of cosmetics is not particularly limited, and may be lotions, cream gels, sprays, and the like. More specifically, cosmetics include skin care cosmetics such as face wash, makeup remover, lotion, serum, pack, protective milky lotion, protective cream, whitening cosmetics, UV protection cosmetics, foundation, white powder, makeup base, lipstick. , makeup cosmetics such as eye makeup, blusher, nail enamel, hair care cosmetics such as shampoo, hair rinse, hair treatment, hair styling agent, permanent waving agent, hair dye, and hair restorer, body cleansing cosmetics, deodorant cosmetics, bath agents and other body care cosmetics.
- skin care cosmetics such as face wash, makeup remover, lotion, serum, pack, protective milky lotion, protective cream, whitening cosmetics, UV protection cosmetics, foundation, white powder, makeup base, lipstick.
- makeup cosmetics such as eye makeup, blusher, nail enamel, hair care cosmetics such as shampoo,
- the content of the water-insoluble dye composition in cosmetics is not particularly limited, and may be appropriately set according to the type of cosmetics.
- the content of the water-insoluble dye composition in cosmetics is usually 0.1 to 99% by mass, and in general cosmetics, it is preferably 0.1 to 10% by mass.
- the content of the water-insoluble dye composition in makeup cosmetics intended for coloring is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, and even more preferably 20 to 60% by mass. If the content of the water-insoluble dye composition is within the above range, there is a tendency that functions such as colorability can be effectively exhibited and functions required for cosmetics can be maintained.
- Cosmetics in addition to the water-insoluble dye composition of the present invention, may contain carriers, pigments, oils, sterols, amino acids, moisturizing agents, powders, colorants, and pH adjusters that are acceptable as cosmetic ingredients, depending on the type of cosmetics.
- fragrances essential oils
- active cosmetic ingredients vitamins, essential fatty acids, sphingolipids, self-tanning agents, excipients, fillers, emulsifiers, antioxidants, surfactants, chelating agents, gelling agents, thickeners, emollients agents, humectants, humectants, minerals, viscosity modifiers, rheology modifiers, keratolytic agents, retinoids, hormonal compounds, alpha hydroxy acids, alpha keto acids, antimycobacterial agents, antifungal agents, antibacterial agents, antiviral agents , analgesic, anti-allergic, anti-histamine, anti-inflammatory, anti-irritant, antineoplastic, immune system booster, immune system suppressant, anti-acne, anesthetic, antiseptic, insect repellent, skin cooling compound, skin Protectants, skin penetration enhancers, exfoliants, lubricants, fragrances, dyes, bleaching agents, hypopigmenting agents, preservatives
- Cosmetics can be produced, for example, by mixing a water-insoluble pigment composition and other cosmetic ingredients.
- cosmetics containing a water-insoluble dye composition can be used in the same manner as ordinary cosmetics, depending on the type of cosmetics.
- the water-insoluble dye composition of the present invention can also be used for plastic coloring applications.
- thermoplastic resins (plastics) for thermoforming such as injection molding and press molding, such as polyolefins such as polyethylene and polypropylene, and polyvinyl chloride resins, are used.
- the water-insoluble dye composition can be kneaded into these resins by a conventionally known method.
- the water-insoluble dye composition of the present invention can also be used for toner applications.
- the toner for electrostatic charge image development for example, film forming thermoplastic resins such as polyester resins, polyamide resins, styrene resins, and acrylic resins, which are solid at room temperature, are used as dispersing resins.
- Electrostatic image developing toners produced using the water-insoluble dye composition of the present invention as a constituent component include one-component color magnetic toner containing a magnetic substance in the toner (color toner for magnetic one-component development), Non-magnetic one-component color toner (color toner for non-magnetic one-component development) containing no carrier, or color toner for two-component color developer mixed with carrier (color toner for two-component development).
- One-component color magnetic toners are composed of, for example, colorants, binder resins, magnetic powders, charge control agents (CCA), and other additives such as releasing agents. be.
- the content of the water-insoluble dye composition in the toner for electrostatic charge development is not particularly limited, but is preferably 0.5 to 25 parts by mass with respect to 100 parts by mass of the binder resin. From the viewpoint of making the charging performance more remarkable, it is more preferably 4 to 10 parts by mass with respect to 100 parts by mass of the binder resin.
- the binder resin used in the toner for electrostatic charge development is not particularly limited, and the resins exemplified as the above thermoplastic resins can be used. Synthetic resins, natural resins, natural rubbers, synthetic rubbers, synthetic waxes, etc. that exhibit adhesiveness under the application of heat or pressure can also be used.
- Example 1 ⁇ Preparation of water-insoluble dye composition> Linablue G1 (manufactured by DIC Lifetech Co., Ltd., 55% trehalose, 40% phycocyanin pigment, 5% trisodium citrate) 25 parts by weight (10 parts by weight phycocyanin pigment) and 100 parts by weight of water are added to a beaker and stirred at room temperature for 10 minutes. After stirring for 1 minute, an aqueous solution of phycocyanin was prepared.
- Linablue G1 manufactured by DIC Lifetech Co., Ltd., 55% trehalose, 40% phycocyanin pigment, 5% trisodium citrate
- the filtered solid matter was transferred to a beaker and vacuum-heated and dried at 50°C.
- the dried powder was ground in an agate mortar and passed through a sieve with an opening of 100 ⁇ m to obtain a blue powder as a water-insoluble dye composition.
- lithographic offset printing ink Using the obtained powder, a lithographic offset printing ink was prepared as follows.
- Examples 2-5) A blue powder as a water-insoluble pigment composition was obtained in the same manner as in Example 1, except that the amounts of phycocyanin pigment and ⁇ -carrageenan were changed to those shown in Table 1. Using the obtained powder, in the same manner as in Example 1, a lithographic offset printing ink and an ink development were prepared.
- Linablue G1 55% trehalose, 40% phycocyanin pigment, 5% trisodium citrate, manufactured by DIC Lifetech Co., Ltd.
- a dispersion liquid was dropped onto the filter paper, it was observed that the blue liquid spread uniformly concentrically around the dropped portion. This indicates that Linablue G1 was dissolved in water in the dispersion, and phycocyanin was soluble in water.
- the first circle-shaped blue colored portion is the powder insoluble in water, and the portion where the transparent liquid spreads concentrically after that is water, and the powders of Examples 1 to 5 are insoluble in water. Do you get it.
- Table 1 shows the results of the hue measurements of the printing ink developments.
- the water-insoluble pigment compositions of the present invention of Examples 1-5 were insoluble in water, but phycocyanin of Comparative Example 1 was water-soluble. Also, as shown in Table 1, the printing inks using the water-insoluble dye compositions of Examples 1 to 5 were found to have a vivid blue color. Among them, it was found that the printing inks using the water-insoluble dye compositions of Examples 1 to 4 had a particularly clear blue color.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Birds (AREA)
- General Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Provided is a water-insoluble pigment composition in which phycocyanin is made insoluble in water. The present invention is a water-insoluble pigment composition in which phycocyanin and carrageenan are composited.
Description
本発明は、非水溶性色素組成物に関する。
The present invention relates to a water-insoluble dye composition.
食品用色素として、多種多様の赤色色素、黄色色素、青色色素が存在するが、近年、発癌性等の問題から合成着色料が疑問視され、より安全性が高いと考えられている天然色素に対する期待が大きくなっている。しかし、天然色素には物性的に一長一短があり、特に色調的に鮮明な赤色・青色色素が少ないのが現状である。
There are a wide variety of red, yellow, and blue colorants for food, but in recent years, synthetic colorants have been questioned due to problems such as carcinogenicity. Expectations are high. However, natural pigments have both advantages and disadvantages in terms of physical properties, and the current situation is that red and blue pigments that are particularly vivid in color tone are scarce.
青色を呈する天然色素として藻類色素のフィコシアニン色素がある。フィコシアニン色素は蛋白質結合色素であり、藍藻類のスピルリナ等から抽出することができることが知られている。フィコシアニンは鮮明な青色を呈する色素であり、サステナブル色素として市場の期待も大きい。
Phycocyanin, an algae pigment, is a natural blue pigment. Phycocyanin pigments are protein-binding pigments and are known to be extractable from blue-green algae such as Spirulina. Phycocyanin is a pigment that exhibits a vivid blue color, and there are high expectations in the market as a sustainable pigment.
この市場の大きな期待から、近年、フィコシアニンに関する研究が数多く報告されている。例えば、フィコシアニンと、ヒドロキシ基を１つ以上含む多価カルボン酸と、特定の非イオン性乳化剤とを混合させることにより、フィコシアニンの熱的安定性を改善させた研究が報告されている（特許文献１参照）。
Due to the great expectations of this market, many studies on phycocyanin have been reported in recent years. For example, studies have been reported to improve the thermal stability of phycocyanin by mixing phycocyanin, a polycarboxylic acid containing one or more hydroxy groups, and a specific nonionic emulsifier (Patent Document 1).
しかしながら、フィコシアニンは、上述したように蛋白質結合色素であるために水溶性であり、水への溶出やそれに伴う色落ちの問題が生じやすいという問題があった。特許文献１のようにフィコシアニンの熱的安定性を改善した研究は報告されているものの、フィコシアニンを非水溶化した研究は未だ報告されていない。このためフィコシアニンは、ごく限られた用途でしか使用されていなかった。
However, as mentioned above, phycocyanin is a protein-bound pigment, so it is water-soluble, and has the problem of elution in water and the resulting color fading. As in Patent Document 1, studies have been reported on improving the thermal stability of phycocyanin, but studies on making phycocyanin non-water-soluble have not yet been reported. For this reason, phycocyanin has been used only in very limited applications.
本発明は、フィコシアニンが非水溶化された、非水溶性色素組成物を提供することを目的とする。
An object of the present invention is to provide a water-insoluble pigment composition in which phycocyanin is water-insoluble.
本発明者らは、上記課題を解決すべく鋭意研究した結果、フィコシアニンと、カラギーナンとを複合化することで、水中にフィコシアニンを溶出しなくなることを見出し、本発明を完成するに至った。
As a result of intensive research to solve the above problems, the present inventors found that phycocyanin does not elute into water by combining phycocyanin with carrageenan, and completed the present invention.
すなわち、本発明は、以下の態様を包含するものである。
［１］フィコシアニンと、カラギーナンとが複合化してなる、非水溶性色素組成物。
［２］上記非水溶性色素組成物における上記フィコシアニンと上記カラギーナンとの組成比が、質量比で、１００：１～１００：７５である、［１］に記載の非水溶性色素組成物。
［３］上記フィコシアニンが藍藻類由来のフィコシアニンである、［１］又は［２］に記載の非水溶性色素組成物。
［４］上記藍藻類がスピルリナ属の藍藻類である、［３］に記載の非水溶性色素組成物。
［５］上記非水溶性色素組成物は、食品、化粧品、医薬品、文具、筆記部、印刷インキ、インクジェットインキ、塗料、プラスチック着色剤、又はトナー用の組成物である、［１］～［４］のいずれかに記載の非水溶性色素組成物。 That is, the present invention includes the following aspects.
[1] A water-insoluble pigment composition comprising a complex of phycocyanin and carrageenan.
[2] The water-insoluble pigment composition according to [1], wherein the composition ratio of the phycocyanin and the carrageenan in the water-insoluble pigment composition is 100:1 to 100:75 by weight.
[3] The water-insoluble pigment composition according to [1] or [2], wherein the phycocyanin is derived from cyanobacteria.
[4] The water-insoluble dye composition according to [3], wherein the blue-green algae belong to the genus Spirulina.
[5] The water-insoluble dye composition is a composition for foods, cosmetics, pharmaceuticals, stationery, writing parts, printing inks, inkjet inks, paints, plastic colorants, or toners [1] to [4] ] The water-insoluble dye composition according to any one of the above.
［１］フィコシアニンと、カラギーナンとが複合化してなる、非水溶性色素組成物。
［２］上記非水溶性色素組成物における上記フィコシアニンと上記カラギーナンとの組成比が、質量比で、１００：１～１００：７５である、［１］に記載の非水溶性色素組成物。
［３］上記フィコシアニンが藍藻類由来のフィコシアニンである、［１］又は［２］に記載の非水溶性色素組成物。
［４］上記藍藻類がスピルリナ属の藍藻類である、［３］に記載の非水溶性色素組成物。
［５］上記非水溶性色素組成物は、食品、化粧品、医薬品、文具、筆記部、印刷インキ、インクジェットインキ、塗料、プラスチック着色剤、又はトナー用の組成物である、［１］～［４］のいずれかに記載の非水溶性色素組成物。 That is, the present invention includes the following aspects.
[1] A water-insoluble pigment composition comprising a complex of phycocyanin and carrageenan.
[2] The water-insoluble pigment composition according to [1], wherein the composition ratio of the phycocyanin and the carrageenan in the water-insoluble pigment composition is 100:1 to 100:75 by weight.
[3] The water-insoluble pigment composition according to [1] or [2], wherein the phycocyanin is derived from cyanobacteria.
[4] The water-insoluble dye composition according to [3], wherein the blue-green algae belong to the genus Spirulina.
[5] The water-insoluble dye composition is a composition for foods, cosmetics, pharmaceuticals, stationery, writing parts, printing inks, inkjet inks, paints, plastic colorants, or toners [1] to [4] ] The water-insoluble dye composition according to any one of the above.
本発明によれば、フィコシアニンが非水溶化された、非水溶性色素組成物を提供することができる。
According to the present invention, it is possible to provide a water-insoluble pigment composition in which phycocyanin is water-insoluble.
以下、本発明の非水溶性色素組成物について詳細に説明するが、以下に記載する構成要件の説明は、本発明の一実施態様としての一例であり、これらの内容に特定されるものではない。
Hereinafter, the water-insoluble dye composition of the present invention will be described in detail, but the description of the constituent elements described below is an example as one embodiment of the present invention, and is not limited to these contents. .
（非水溶性色素組成物）
本発明の非水溶性色素組成物は、フィコシアニンと、カラギーナンとが複合化してなる組成物である。なお、本明細書において「非水溶性」とは、２５℃における水への溶解性が１質量％未満であることをいう。 (Water-insoluble dye composition)
The water-insoluble pigment composition of the present invention is a composite of phycocyanin and carrageenan. As used herein, the term “water-insoluble” means that the solubility in water at 25° C. is less than 1% by mass.
本発明の非水溶性色素組成物は、フィコシアニンと、カラギーナンとが複合化してなる組成物である。なお、本明細書において「非水溶性」とは、２５℃における水への溶解性が１質量％未満であることをいう。 (Water-insoluble dye composition)
The water-insoluble pigment composition of the present invention is a composite of phycocyanin and carrageenan. As used herein, the term “water-insoluble” means that the solubility in water at 25° C. is less than 1% by mass.
フィコシアニンは水溶性であるが、本発明の非水溶性色素組成物は、鮮やかな青色を有すると共に、フィコシアニンの水への溶出がない。フィコシアニンの水への溶出がない理由として、カラギーナンとの化学結合によって水への溶出が阻害されているものと推定される。従って、本発明の非水溶性色素組成物は、フィコシアニンとカラギーナンとが化学結合により複合化されているものと推定される。より具体的には、フィコシアニン中のフィコシアノビリンのＮＨ基および／またはフィコシアニン中の塩基性アミノ基と、カラギーナン中の硫酸基との化学結合により複合化されているものと推定される。
すなわち、本明細書において「複合化」とは、フィコシアニンとカラギーナンとが化学結合している状態であることをいう。 Although phycocyanin is water-soluble, the water-insoluble pigment composition of the present invention has a vivid blue color and does not dissolve phycocyanin into water. It is presumed that the reason why phycocyanin does not dissolve in water is that the chemical bond with carrageenan inhibits the dissolution of phycocyanin in water. Therefore, in the water-insoluble pigment composition of the present invention, phycocyanin and carrageenan are presumed to be chemically bonded. More specifically, it is presumed that the NH group of phycocyanobilin in phycocyanin and/or the basic amino group in phycocyanin are chemically bonded to the sulfate group in carrageenan.
That is, the term "complexed" as used herein means a state in which phycocyanin and carrageenan are chemically bonded.
すなわち、本明細書において「複合化」とは、フィコシアニンとカラギーナンとが化学結合している状態であることをいう。 Although phycocyanin is water-soluble, the water-insoluble pigment composition of the present invention has a vivid blue color and does not dissolve phycocyanin into water. It is presumed that the reason why phycocyanin does not dissolve in water is that the chemical bond with carrageenan inhibits the dissolution of phycocyanin in water. Therefore, in the water-insoluble pigment composition of the present invention, phycocyanin and carrageenan are presumed to be chemically bonded. More specifically, it is presumed that the NH group of phycocyanobilin in phycocyanin and/or the basic amino group in phycocyanin are chemically bonded to the sulfate group in carrageenan.
That is, the term "complexed" as used herein means a state in which phycocyanin and carrageenan are chemically bonded.
本発明の非水溶性色素組成物におけるフィコシアニンとカラギーナンとの組成比（フィコシアニン：カラギーナン）は、質量比で、１００：１～１００：１００であることが好ましく、１００：１～１００：７５であることがより好ましく、１００：３～１００：７５であることが更に好ましく、１００：３～１００：５０であることが特に好ましい。上記範囲内であれば、フィコシアニンを効果的に非水溶化でき、かつ鮮明な青色を有する組成物が得られる傾向がある。
The composition ratio of phycocyanin and carrageenan (phycocyanin: carrageenan) in the water-insoluble pigment composition of the present invention is preferably 100: 1 to 100: 100, more preferably 100: 1 to 100: 75. is more preferred, 100:3 to 100:75 is even more preferred, and 100:3 to 100:50 is particularly preferred. Within the above range, there is a tendency to effectively solubilize phycocyanin and obtain a composition having a clear blue color.
非水溶性色素組成物の平均粒子径は、特に制限されないが、例えば、インキ化時の発色性や隠ぺい性の観点から０．０１～１００μｍであることが好ましく、０．０５～５０μｍであることがより好ましく、０．１～２０μｍであることが更に好ましい。
なお、非水溶性色素組成物の平均粒子径の値は、透過型又は走査型の電子顕微鏡等で粒子を撮影し、２０個の粒子についてその最長径を測長した算術平均値である。 Although the average particle size of the water-insoluble dye composition is not particularly limited, it is preferably 0.01 to 100 μm, more preferably 0.05 to 50 μm, from the viewpoint of color development and hiding properties during ink formation. is more preferable, and 0.1 to 20 μm is even more preferable.
The average particle size of the water-insoluble dye composition is the arithmetic average value obtained by photographing particles with a transmission or scanning electron microscope or the like and measuring the longest diameter of 20 particles.
なお、非水溶性色素組成物の平均粒子径の値は、透過型又は走査型の電子顕微鏡等で粒子を撮影し、２０個の粒子についてその最長径を測長した算術平均値である。 Although the average particle size of the water-insoluble dye composition is not particularly limited, it is preferably 0.01 to 100 μm, more preferably 0.05 to 50 μm, from the viewpoint of color development and hiding properties during ink formation. is more preferable, and 0.1 to 20 μm is even more preferable.
The average particle size of the water-insoluble dye composition is the arithmetic average value obtained by photographing particles with a transmission or scanning electron microscope or the like and measuring the longest diameter of 20 particles.
以下、非水溶性色素組成物の各成分について説明する。
Each component of the water-insoluble dye composition will be described below.
＜フィコシアニン＞
フィコシアニンは、蛋白質結合色素であり、発色団としてフィコシアノビリンを有する。フィコシアニンは、フィコシアノビリンとタンパクとが結合した構造を備える。 <Phycocyanin>
Phycocyanin is a protein-bound pigment and has phycocyanobilin as its chromophore. Phycocyanin has a structure in which phycocyanobilin and protein are bound together.
フィコシアニンは、蛋白質結合色素であり、発色団としてフィコシアノビリンを有する。フィコシアニンは、フィコシアノビリンとタンパクとが結合した構造を備える。 <Phycocyanin>
Phycocyanin is a protein-bound pigment and has phycocyanobilin as its chromophore. Phycocyanin has a structure in which phycocyanobilin and protein are bound together.
本実施形態に係るフィコシアニンの由来は特に制限されない。本実施形態に係るフィコシアニンは、例えば、藍藻類由来のフィコシアニン、紅藻類由来のフィコシアニン、クリプト藻由来のフィコシアニン等の藻類由来のフィコシアニン等を用いることができる。これらの中でも、フィコシアニンとしては、大量に採取できる観点から、藍藻類由来のフィコシアニンを用いるのが好ましい。フィコシアニンは１種を単独で使用してもよいし、２種以上を組み合わせて使用してもよい。
The origin of phycocyanin according to this embodiment is not particularly limited. As the phycocyanin according to the present embodiment, for example, phycocyanin derived from algae such as phycocyanin derived from cyanobacteria, phycocyanin derived from red algae, and phycocyanin derived from cryptophytes can be used. Among these, phycocyanin derived from blue-green algae is preferably used as phycocyanin from the viewpoint of being able to be collected in large amounts. Phycocyanin may be used individually by 1 type, and may be used in combination of 2 or more type.
藍藻類由来のフィコシアニンにおける藍藻類としては、例えば、スピルリナ（Ｓｐｉｒｕｌｉｎａ）属、アルスロスピラ（Ａｒｔｈｒｏｓｐｉｒａ）属、アファニゾメノン（Ａｐｈａｎｉｚｏｍｅｎｏｎ）属、フィッシェレラ（Ｆｉｓｈｅｒｅｌｌａ）属、アナベナ（Ａｎａｂａｅｎａ）属、ネンジュモ（Ｎｏｓｔｏｃ）属、シネコキスチス（Ｓｙｎｅｃｈｏｃｙｓｔｉｓ）属、シネココッカス（Ｓｙｎｅｃｈｏｃｏｃｃｕｓ）属、トリポスリクス（Ｔｏｌｙｐｏｔｈｒｉｘ）属、スイゼンジノリ（Ａｐｈａｎｏｔｈｅｃｅ）属、マスティゴクラディス（Ｍａｓｔｉｇｏｃｌａｕｓ）属、プルロカプサ（Ｐｌｅｕｒｏｃａｐｓａ）属等が挙げられる。これらの中でも、藍藻類としては、工業的規模で生産され、その安全性が確認されていることから、スピルリナ属及びアルスロスピラ属の藍藻類が好ましく、スピルリナ属の藍藻類がより好ましい。
Examples of blue-green algae in phycocyanin derived from blue-green algae include the genus Spirulina, the genus Arthrospira, the genus Aphanizomenon, the genus Fisherella, the genus Anabaena, the genus Nostoc, and the genus Synechocystis. Synechocystis genus, Synechococcus genus, Tolypothrix genus, Aphanothece genus, Mastigoclaus genus, Pleurocapsa genus, and the like. Among these, cyanobacteria belonging to the genus Spirulina and the genus Arthrospira are preferable, and cyanobacteria belonging to the genus Spirulina are more preferable, because they are produced on an industrial scale and their safety has been confirmed.
フィコシアニンは、例えば、藍藻類を水やリン酸緩衝液、クエン酸緩衝液等の緩衝液中に懸濁し、藍藻類中のフィコシアニンを抽出することにより調製することができる。
Phycocyanin can be prepared, for example, by suspending cyanobacteria in water or a buffer solution such as a phosphate buffer or a citrate buffer and extracting phycocyanin in the cyanobacteria.
フィコシアニンを調製する際の藍藻類は、生の藍藻類を用いてもよく、乾燥処理した藍藻類を用いてもよい。藍藻類の乾燥品としては、生の藍藻類を常法に従い乾燥品としてもよく、市販の乾燥品を用いてもよい。
The blue-green algae used in preparing phycocyanin may be fresh blue-green algae or dried blue-green algae. As the dried product of blue-green algae, raw blue-green algae may be dried according to a conventional method, or commercially available dried products may be used.
フィコシアニンの抽出方法は、特に制限されず、常法に従って抽出することができる。フィコシアニンの抽出方法は、例えば、特開２００６－２３０２７２号公報に記載の方法等を好適に用いることができる。以下に抽出方法の一例を示す。
The method for extracting phycocyanin is not particularly limited, and it can be extracted according to a conventional method. As a method for extracting phycocyanin, for example, the method described in JP-A-2006-230272 can be suitably used. An example of the extraction method is shown below.
まず、藍藻類中のフィコシアニンを水懸濁液中に抽出させた抽出液を得る。次いで、該抽出液中でカルシウム塩とリン酸塩とを反応させてリン酸カルシウムを生成させると共に該リン酸カルシウムにフィコシアニンの夾雑物を吸着させ吸着物を得る。該抽出液から藍藻類の残渣及び吸着物を除去し、フィコシアニンを調製する。
なお、該抽出液から藍藻類の残渣及び吸着物を除去する前に、抽出液にキレート剤を含有させるのがより好ましい。 First, an extract is obtained by extracting phycocyanin in blue-green algae into an aqueous suspension. Next, a calcium salt and a phosphate are reacted in the extract to produce calcium phosphate, and impurities of phycocyanin are adsorbed to the calcium phosphate to obtain an adsorbate. Phycocyanin is prepared by removing cyanobacterial residues and adsorbates from the extract.
In addition, it is more preferable to add a chelating agent to the extract before removing the residues and adsorbates of the blue-green algae from the extract.
なお、該抽出液から藍藻類の残渣及び吸着物を除去する前に、抽出液にキレート剤を含有させるのがより好ましい。 First, an extract is obtained by extracting phycocyanin in blue-green algae into an aqueous suspension. Next, a calcium salt and a phosphate are reacted in the extract to produce calcium phosphate, and impurities of phycocyanin are adsorbed to the calcium phosphate to obtain an adsorbate. Phycocyanin is prepared by removing cyanobacterial residues and adsorbates from the extract.
In addition, it is more preferable to add a chelating agent to the extract before removing the residues and adsorbates of the blue-green algae from the extract.
上記の例に示す抽出方法により、高純度であざやかな色調のフィコシアニンを調製することができる。
By the extraction method shown in the example above, it is possible to prepare phycocyanin with high purity and bright color.
フィコシアニンは、上記に示す抽出方法等により調製することができるが、市販品であるリナブルーＧ１（ＤＩＣライフテック（株）製、トレハロース５５％、フィコシアニン色素４０％、クエン酸三ナトリウム５％）を用いてもよい。なお、特開平１１－２９９４５０号公報に記載されているように、トレハロースは熱安定性を向上させるために用いられ、クエン酸はｐＨ調整剤として用いられている。
Phycocyanin can be prepared by the extraction method or the like described above. may Incidentally, as described in JP-A-11-299450, trehalose is used to improve thermal stability, and citric acid is used as a pH adjuster.
＜カラギーナン＞
カラギーナンとは、紅藻類海藻から抽出、精製される天然高分子物質で分子量が１０万～５０万のガラクトース、３、６アンヒドロガラクトースを主成分とする多糖類である。カラギーナンには様々な種類があり、例えば、κ－カラギーナン、λ－カラギーナン、ι－カラギーナン、μ－カラギーナン、ν－カラギーナン、θ－カラギーナン、ξ－カラギーナン、π－カラギーナン等が知られている。各種類の構造上の違いは、ガラクトース骨格の六員環構造と、ガラクトース骨格に存在する硫酸基及び水酸基の立体配座の違いによって分類される。 <Carrageenan>
Carrageenan is a natural high-molecular substance extracted and purified from red algae and seaweed, and is a polysaccharide having a molecular weight of 100,000 to 500,000 and mainly composed of galactose and 3,6-anhydrogalactose. There are various types of carrageenan, for example, κ-carrageenan, λ-carrageenan, ι-carrageenan, μ-carrageenan, ν-carrageenan, θ-carrageenan, ξ-carrageenan, π-carrageenan and the like are known. Structural differences between the types are classified according to the six-membered ring structure of the galactose skeleton and the conformations of the sulfate group and hydroxyl group present in the galactose skeleton.
カラギーナンとは、紅藻類海藻から抽出、精製される天然高分子物質で分子量が１０万～５０万のガラクトース、３、６アンヒドロガラクトースを主成分とする多糖類である。カラギーナンには様々な種類があり、例えば、κ－カラギーナン、λ－カラギーナン、ι－カラギーナン、μ－カラギーナン、ν－カラギーナン、θ－カラギーナン、ξ－カラギーナン、π－カラギーナン等が知られている。各種類の構造上の違いは、ガラクトース骨格の六員環構造と、ガラクトース骨格に存在する硫酸基及び水酸基の立体配座の違いによって分類される。 <Carrageenan>
Carrageenan is a natural high-molecular substance extracted and purified from red algae and seaweed, and is a polysaccharide having a molecular weight of 100,000 to 500,000 and mainly composed of galactose and 3,6-anhydrogalactose. There are various types of carrageenan, for example, κ-carrageenan, λ-carrageenan, ι-carrageenan, μ-carrageenan, ν-carrageenan, θ-carrageenan, ξ-carrageenan, π-carrageenan and the like are known. Structural differences between the types are classified according to the six-membered ring structure of the galactose skeleton and the conformations of the sulfate group and hydroxyl group present in the galactose skeleton.
本実施形態に係るカラギーナンは、いずれの種類のカラギーナンも用いることができるが、κ－カラギーナン、λ－カラギーナン、ι－カラギーナンからなる群から選択される少なくとも１種から選択されるのが好ましい。これらの中でも、硫酸基の含有量が多い観点からは、ι－カラギーナンが好ましい。カラギーナンは１種を単独で使用してもよいし、２種以上を組み合わせて使用してもよい。
Any type of carrageenan can be used as the carrageenan according to the present embodiment, but it is preferably selected from at least one selected from the group consisting of κ-carrageenan, λ-carrageenan, and ι-carrageenan. Among these, ι-carrageenan is preferable from the viewpoint of having a large content of sulfate groups. Carrageenan may be used alone or in combination of two or more.
＜その他の成分＞
本発明の非水溶性色素組成物は、必要に応じて、所望の要求される色相を満たすために、有機顔料、無機顔料、染料、色素等を、本発明の効果を損なわない範囲内で含有させてもよい。 <Other ingredients>
The water-insoluble dye composition of the present invention contains organic pigments, inorganic pigments, dyes, pigments, etc., as necessary, in order to satisfy the desired desired hue within a range that does not impair the effects of the present invention. You may let
本発明の非水溶性色素組成物は、必要に応じて、所望の要求される色相を満たすために、有機顔料、無機顔料、染料、色素等を、本発明の効果を損なわない範囲内で含有させてもよい。 <Other ingredients>
The water-insoluble dye composition of the present invention contains organic pigments, inorganic pigments, dyes, pigments, etc., as necessary, in order to satisfy the desired desired hue within a range that does not impair the effects of the present invention. You may let
本発明の非水溶性色素組成物は、必要に応じて、更に耐光性、耐熱性等を付与するために、熱安定化剤、光安定化剤等のその他の添加剤を、本発明の効果を損なわない範囲内で含有させてもよい。
熱安定化剤としては、例えばフェノール系酸化防止剤、リン系熱安定剤、サルファイトケイ熱安定剤等を、通常０．００１～１質量％の範囲内で使用することができる。光安定剤としては、例えばベンゾフェノン系紫外線吸収剤、サリチル酸エステル系紫外線吸収剤、トリアジン系紫外線吸収剤、ベンゾトリアゾール系紫外線吸収剤、ヒンダードアミン系光安定剤等を、通常０．００１～１質量％の範囲内で使用することができる。 The water-insoluble dye composition of the present invention may optionally contain other additives such as heat stabilizers and light stabilizers in order to further impart light resistance, heat resistance, etc., to the effect of the present invention. may be contained within a range that does not impair the
As the heat stabilizer, for example, a phenol-based antioxidant, a phosphorus-based heat stabilizer, a sulfite-silicone heat stabilizer, etc. can be used in the range of 0.001 to 1% by mass. Examples of light stabilizers include benzophenone-based UV absorbers, salicylic acid ester-based UV absorbers, triazine-based UV absorbers, benzotriazole-based UV absorbers, hindered amine-based light stabilizers, and the like, usually in an amount of 0.001 to 1% by mass. Can be used within range.
熱安定化剤としては、例えばフェノール系酸化防止剤、リン系熱安定剤、サルファイトケイ熱安定剤等を、通常０．００１～１質量％の範囲内で使用することができる。光安定剤としては、例えばベンゾフェノン系紫外線吸収剤、サリチル酸エステル系紫外線吸収剤、トリアジン系紫外線吸収剤、ベンゾトリアゾール系紫外線吸収剤、ヒンダードアミン系光安定剤等を、通常０．００１～１質量％の範囲内で使用することができる。 The water-insoluble dye composition of the present invention may optionally contain other additives such as heat stabilizers and light stabilizers in order to further impart light resistance, heat resistance, etc., to the effect of the present invention. may be contained within a range that does not impair the
As the heat stabilizer, for example, a phenol-based antioxidant, a phosphorus-based heat stabilizer, a sulfite-silicone heat stabilizer, etc. can be used in the range of 0.001 to 1% by mass. Examples of light stabilizers include benzophenone-based UV absorbers, salicylic acid ester-based UV absorbers, triazine-based UV absorbers, benzotriazole-based UV absorbers, hindered amine-based light stabilizers, and the like, usually in an amount of 0.001 to 1% by mass. Can be used within range.
（非水溶性色素組成物の製造方法）
本実施形態に係る非水溶性色素組成物を製造する方法としては、特に制限されないが、溶媒中でフィコシアニンとカラギーナンとを混合する方法が均一な非水溶性色素組成物を製造することができるため好ましい。溶媒は、水性溶媒であればよく、水を用いるのが好ましいが、エタノール、イソプロパノール、又はアセトン等の溶媒と水との混合液等を用いてもよい。 (Method for producing water-insoluble dye composition)
The method for producing the water-insoluble pigment composition according to the present embodiment is not particularly limited, but the method of mixing phycocyanin and carrageenan in a solvent can produce a uniform water-insoluble pigment composition. preferable. The solvent may be an aqueous solvent, preferably water, but a mixture of water and a solvent such as ethanol, isopropanol, or acetone may also be used.
本実施形態に係る非水溶性色素組成物を製造する方法としては、特に制限されないが、溶媒中でフィコシアニンとカラギーナンとを混合する方法が均一な非水溶性色素組成物を製造することができるため好ましい。溶媒は、水性溶媒であればよく、水を用いるのが好ましいが、エタノール、イソプロパノール、又はアセトン等の溶媒と水との混合液等を用いてもよい。 (Method for producing water-insoluble dye composition)
The method for producing the water-insoluble pigment composition according to the present embodiment is not particularly limited, but the method of mixing phycocyanin and carrageenan in a solvent can produce a uniform water-insoluble pigment composition. preferable. The solvent may be an aqueous solvent, preferably water, but a mixture of water and a solvent such as ethanol, isopropanol, or acetone may also be used.
溶媒中で各成分を混合する非水溶性色素組成物の製造方法としては、例えば、１）カラギーナンの水溶液又は水分散液を調製する。２）一方でフィコシアニンを水に溶解し、フィコシアニンの水溶液を調製する。３）上記２つの液を混合して、非水溶性色素組成物を調製する。４）得られた非水溶性色素組成物を含む混合液をろ過、乾燥する方法等が挙げられる。
As a method for producing a water-insoluble dye composition by mixing each component in a solvent, for example, 1) prepare an aqueous solution or aqueous dispersion of carrageenan. 2) Meanwhile, phycocyanin is dissolved in water to prepare an aqueous solution of phycocyanin. 3) Mix the above two liquids to prepare a water-insoluble dye composition. 4) A method of filtering and drying the mixed liquid containing the obtained water-insoluble dye composition, and the like.
フィコシアニン、カラギーナン及び水の混合順序は問わない。例えば、カラギーナンの水分散液又は水溶液にフィコシアニンの水溶液を混合してもよいし、その逆にフィコシアニンの水溶液にカラギーナンの水分散液又は水溶液を混合してもよい。また、これら２つの液を少量ずつ混合しながら調製してもよい。
Phycocyanin, carrageenan and water can be mixed in any order. For example, an aqueous dispersion or aqueous solution of carrageenan may be mixed with an aqueous solution of phycocyanin, or vice versa. Moreover, you may prepare, mixing these two liquids little by little.
フィコシアニンの水溶液の固形分濃度は、非水溶性色素組成物におけるフィコシアニンとカラギーナンの組成比が上述した範囲内であれば、特に制限されない。フィコシアニンの水溶液の固形分濃度は、取扱性、生産性等を考慮して適宜設定すればよいが、水溶液の総量に対して０．１～４０質量％であることが好ましく、１～３０質量％であることが好ましい。
The solid content concentration of the aqueous solution of phycocyanin is not particularly limited as long as the composition ratio of phycocyanin and carrageenan in the water-insoluble pigment composition is within the range described above. The solid content concentration of the aqueous solution of phycocyanin may be appropriately set in consideration of handling, productivity, etc., but it is preferably 0.1 to 40% by mass, more preferably 1 to 30% by mass, based on the total amount of the aqueous solution. is preferably
カラギーナンの水溶液又は水分散液の固形分濃度についても、非水溶性色素組成物におけるフィコシアニンとカラギーナンの組成比が上述した範囲内であれば、特に制限されない。カラギーナンの水溶液又は水分散液の固形分濃度は、取扱性、生産性等を考慮して適宜設定すればよいが、水溶液又は水分散液の総量に対して０．０１～１０質量％であることが好ましく、０．１～７質量％であることが好ましい。
The solid content concentration of the carrageenan aqueous solution or aqueous dispersion is also not particularly limited as long as the composition ratio of phycocyanin and carrageenan in the water-insoluble pigment composition is within the range described above. The solid content concentration of the carrageenan aqueous solution or aqueous dispersion may be appropriately set in consideration of handling, productivity, etc., but it should be 0.01 to 10% by mass based on the total amount of the aqueous solution or aqueous dispersion. is preferred, preferably 0.1 to 7% by mass.
なお、フィコシアニン及びカラギーナンは、粉末状のものを添加して混合してもよい。例えば、フィコシアニンの水溶液にカラギーナンの粉末を添加して混合してもよいし、カラギーナンの水溶液又は水分散液にフィコシアニンの粉末を添加して混合してもよい。また、フィコシアニン、カラギーナンの粉末を混合した後に水を添加して混合してもよい。
Phycocyanin and carrageenan may be added in powder form and mixed. For example, carrageenan powder may be added to an aqueous solution of phycocyanin and mixed, or phycocyanin powder may be added to an aqueous solution or dispersion of carrageenan and mixed. Moreover, after mixing powders of phycocyanin and carrageenan, water may be added and mixed.
混合温度は、特に制限されず、室温であっても、加熱して混合しても構わない。フィコシアニンの分解温度を考慮し、混合温度は、１０～６０℃が好ましく、２０～５０℃がより好ましい。
混合時間は、特に制限されず、１０分～３時間行うことが好ましく、３０分～２時間がより好ましい。 The mixing temperature is not particularly limited, and the mixture may be mixed at room temperature or under heating. Considering the decomposition temperature of phycocyanin, the mixing temperature is preferably 10 to 60°C, more preferably 20 to 50°C.
The mixing time is not particularly limited, and is preferably 10 minutes to 3 hours, more preferably 30 minutes to 2 hours.
混合時間は、特に制限されず、１０分～３時間行うことが好ましく、３０分～２時間がより好ましい。 The mixing temperature is not particularly limited, and the mixture may be mixed at room temperature or under heating. Considering the decomposition temperature of phycocyanin, the mixing temperature is preferably 10 to 60°C, more preferably 20 to 50°C.
The mixing time is not particularly limited, and is preferably 10 minutes to 3 hours, more preferably 30 minutes to 2 hours.
混合する際のｐＨの範囲は、特に制限されないが、フィコシアニン水溶液をｐＨ４．２以下にするとフィコシアニンが緑変し沈殿を生じ得るため、４．５～８．０が好ましく、５．５～７．５がより好ましく、６．３～７．０が更に好ましい。ｐＨを調整する場合、ｐＨ調整剤としては、特に制限されず、例えば、塩酸、クエン酸、酢酸、乳酸等が挙げられる。
The pH range for mixing is not particularly limited, but if the pH of the phycocyanin aqueous solution is less than 4.2, phycocyanin may turn green and precipitate. 5 is more preferred, and 6.3 to 7.0 is even more preferred. When adjusting the pH, the pH adjuster is not particularly limited, and examples thereof include hydrochloric acid, citric acid, acetic acid, lactic acid and the like.
上記のようにして得られた非水溶性色素組成物を含む混合液を、ろ過、乾燥し、非水溶性色素組成物を得ることができる。混合液をヌッチェ等のろ過器でろ過し、ウェットケーキの水洗を繰り返す。水洗開始直後には、ろ液は着色しているが、水洗を繰り返すにつれて徐々にろ液の着色が薄くなり、最終的に無色透明になる。ろ液に着色がなくなった後もウェットケーキが着色していることから、フィコシアニンとカラギーナンとが複合化されていることが確認できる。得られた非水溶性色素組成物の水含有ウェットケーキは、減圧乾燥等により乾燥し、ドライの非水溶性色素組成物を得ることができる。乾燥方法及び乾燥機は、通常の方法及び通常の装置であればいかなるものでも可能であり、限定されるものではない。
The mixed liquid containing the water-insoluble dye composition obtained as described above can be filtered and dried to obtain the water-insoluble dye composition. The mixed solution is filtered through a filter such as Nutsche, and the wet cake is repeatedly washed with water. Immediately after the start of washing with water, the filtrate is colored, but as the washing with water is repeated, the coloring of the filtrate gradually becomes lighter and finally becomes colorless and transparent. Since the wet cake remains colored even after the filtrate is no longer colored, it can be confirmed that phycocyanin and carrageenan are combined. The obtained water-insoluble wet cake of the water-insoluble dye composition can be dried by vacuum drying or the like to obtain a dry water-insoluble dye composition. The drying method and dryer are not limited as long as they are ordinary methods and ordinary devices.
本発明の非水溶性色素組成物は、上記の水が含有したウェットケーキであっても乾燥したドライの組成物であっても、用途によって使い分けが可能である。水系の分散液、インキに使用する場合は、ウェットケーキをそのまま使用することができ、液剤分散系の場合は、水系から溶剤系に置換して使用することができる。ドライの組成物は、そのままでも使用できるし、水、または有機溶媒、樹脂溶液等に再分散させて使用することもできる。
Whether the water-insoluble dye composition of the present invention is a wet cake containing water or a dry composition, it can be used properly depending on the application. When used for water-based dispersions and inks, the wet cake can be used as it is, and when used for liquid agent dispersions, the water-based system can be replaced with a solvent-based system. The dry composition can be used as it is, or can be used after being redispersed in water, an organic solvent, a resin solution, or the like.
上記の方法によって得られた非水溶性色素組成物により、青色色素として食品や化粧品用途に限定されていたフィコシアニンを、通常の顔料と同等の着色材として、食品、化粧品、医薬品、文具、筆記部、印刷インキ、インクジェットインキ、塗料、プラスチック着色剤、又はトナー等の用途に使用できる耐性まで向上させることができる。また、不溶化に伴い、耐熱性、耐光性等の特性向上も期待できる。なお、本発明の非水溶性色素組成物の用途は、上記の用途に限定されるものではない。下記に、用途の一例について説明する。
With the water-insoluble pigment composition obtained by the above method, phycocyanin, which has been limited to food and cosmetic applications as a blue pigment, can be used as a coloring material equivalent to ordinary pigments in foods, cosmetics, pharmaceuticals, stationery, and writing parts. , printing inks, inkjet inks, paints, plastic colorants, or toners. Further, along with the insolubilization, it can be expected to improve properties such as heat resistance and light resistance. The uses of the water-insoluble dye composition of the present invention are not limited to the uses described above. An example of application is described below.
＜印刷インキ、塗料用途＞
本発明の非水溶性色素組成物は、印刷インキ、塗料用途として用いることができる。下記に印刷インキ、塗料の用途、組成について説明するが、これらに限定されるものではない。また本発明の非水溶性色素組成物は、熱可塑性樹脂のみに分散させてもよいが、熱可塑性樹脂を必須成分として含有する印刷インキ用ビヒクルや塗料用ビヒクル等に分散させることもできる。 <For printing inks and paints>
The water-insoluble dye composition of the present invention can be used for printing inks and paints. The applications and compositions of printing inks and paints are described below, but are not limited to these. The water-insoluble dye composition of the present invention may be dispersed only in a thermoplastic resin, but it can also be dispersed in a printing ink vehicle or paint vehicle containing a thermoplastic resin as an essential component.
本発明の非水溶性色素組成物は、印刷インキ、塗料用途として用いることができる。下記に印刷インキ、塗料の用途、組成について説明するが、これらに限定されるものではない。また本発明の非水溶性色素組成物は、熱可塑性樹脂のみに分散させてもよいが、熱可塑性樹脂を必須成分として含有する印刷インキ用ビヒクルや塗料用ビヒクル等に分散させることもできる。 <For printing inks and paints>
The water-insoluble dye composition of the present invention can be used for printing inks and paints. The applications and compositions of printing inks and paints are described below, but are not limited to these. The water-insoluble dye composition of the present invention may be dispersed only in a thermoplastic resin, but it can also be dispersed in a printing ink vehicle or paint vehicle containing a thermoplastic resin as an essential component.
熱可塑性樹脂としては、例えば、ポリエステル樹脂、ポリアミド樹脂、スチレン樹脂、アクリル樹脂、ポリオレフィン、ポリアルキレンテレフタレート、ポリ塩化ビニル樹脂等の樹脂が挙げられる。
Examples of thermoplastic resins include resins such as polyester resins, polyamide resins, styrene resins, acrylic resins, polyolefins, polyalkylene terephthalates, and polyvinyl chloride resins.
平版オフセット印刷インキ用ビヒクルは、例えば、ロジン変性フェノール樹脂、石油樹脂、アルキッド樹脂等の樹脂２０～５０質量％、アマニ油、桐油、大豆脂等の動植物脂０～３０質量％、ｎ－パラフィン、イソパラフィン、ナフテン、α―オレフィン、アロマティック等の溶剤１０～６０質量％、その他可溶化剤、ゲル化剤等の添加剤、数質量％を原料に用いて製造することができる。
Vehicles for lithographic offset printing inks include, for example, 20 to 50% by mass of resins such as rosin-modified phenolic resins, petroleum resins and alkyd resins, 0 to 30% by mass of animal and vegetable fats such as linseed oil, tung oil and soybean fat, n-paraffin, It can be produced using 10 to 60% by mass of solvents such as isoparaffins, naphthenes, α-olefins, and aromatics, and several mass% of additives such as solubilizers and gelling agents as raw materials.
グラビア印刷インキ、フレキソ印刷インキ用ビヒクルは、例えばロジン類、マレイン酸樹脂、ポリアミド樹脂、ビニル樹脂、環化ゴム、塩化ゴム、エチレン－酢酸ビニル共重合体樹脂、ウレタン樹脂、ポリエステル樹脂、アルキド樹脂、ニトロセルロース、酢酸セルロース等から選ばれる一種以上の樹脂１０～５０質量％、アルコール類、トルエン、ｎ－ヘキサン、酢酸エチル、セロソルブ、酢酸ブチルセロソルブ等の溶剤３０～８０質量％を原料に用いて製造することができる。
Vehicles for gravure printing inks and flexographic printing inks include, for example, rosins, maleic acid resins, polyamide resins, vinyl resins, cyclized rubbers, chlorinated rubbers, ethylene-vinyl acetate copolymer resins, urethane resins, polyester resins, alkyd resins, Manufactured using 10 to 50% by mass of one or more resins selected from nitrocellulose, cellulose acetate, etc., and 30 to 80% by mass of solvents such as alcohols, toluene, n-hexane, ethyl acetate, cellosolve, and butyl cellosolve as raw materials. be able to.
塗料用のビヒクルは、例えばアルキド樹脂、エポキシ樹脂、アクリル樹脂、ポリウレタン樹脂、ポリエステル樹脂、メラミン樹脂、ユリア樹脂、水溶性樹脂等の樹脂２０～８０質量％、炭化水素類、アルコール類、ケトン類、水等の溶剤１０～６０質量％の原料を原料に用いて製造することができる。
Vehicles for paints include, for example, alkyd resins, epoxy resins, acrylic resins, polyurethane resins, polyester resins, melamine resins, urea resins, water-soluble resins, etc., in an amount of 20 to 80% by mass, hydrocarbons, alcohols, ketones, It can be produced using a raw material containing 10 to 60% by mass of a solvent such as water.
なお、印刷インキ、塗料中の非水溶性色素組成物の含有量は、特に制限されず、目的に応じて適宜設定すればよい。印刷インキ、塗料中の非水溶性色素組成物の含有量は、通常１～５０質量％であり、１０～２５質量％であることが好ましい。
The content of the water-insoluble dye composition in the printing ink or paint is not particularly limited, and may be set appropriately according to the purpose. The content of the water-insoluble dye composition in printing inks and paints is usually 1 to 50% by mass, preferably 10 to 25% by mass.
＜化粧品用途＞
本発明の非水溶性色素組成物は、化粧品用途として用いることができる。 <Cosmetics use>
The water-insoluble dye composition of the present invention can be used for cosmetics.
本発明の非水溶性色素組成物は、化粧品用途として用いることができる。 <Cosmetics use>
The water-insoluble dye composition of the present invention can be used for cosmetics.
化粧品は、本発明の非水溶性色素組成物の効果を発現することができる限り、いかなる種類の化粧品であってもよい。化粧品の剤形は、特に制限されず、ローション、クリームゲル、スプレー等であってもよい。化粧品は、より具体的には、洗顔料、メーク落とし、化粧水、美容液、パック、保護用乳液、保護用クリーム、美白化粧品、紫外線防止化粧品等のスキンケア化粧品、ファンデーション、白粉、化粧下地、口紅、アイメークアップ、頬紅、ネイルエナメル等のメークアップ化粧品、シャンプー、ヘアリンス、ヘアトリートメント、整髪剤、パーマネント・ウェーブ剤、染毛剤、育毛剤等のヘアケア化粧品、身体洗浄用化粧品、デオドラント化粧品、浴用剤等のボディケア化粧品等が挙げられる。
The cosmetics may be any kind of cosmetics as long as they can express the effects of the water-insoluble pigment composition of the present invention. The dosage form of cosmetics is not particularly limited, and may be lotions, cream gels, sprays, and the like. More specifically, cosmetics include skin care cosmetics such as face wash, makeup remover, lotion, serum, pack, protective milky lotion, protective cream, whitening cosmetics, UV protection cosmetics, foundation, white powder, makeup base, lipstick. , makeup cosmetics such as eye makeup, blusher, nail enamel, hair care cosmetics such as shampoo, hair rinse, hair treatment, hair styling agent, permanent waving agent, hair dye, and hair restorer, body cleansing cosmetics, deodorant cosmetics, bath agents and other body care cosmetics.
化粧品中の非水溶性色素組成物の含有量は、特に制限されず、化粧品の種類に応じて適宜設定すればよい。化粧品中の非水溶性色素組成物の含有量は、通常０．１～９９質量％であり、一般的な化粧品においては、０．１～１０質量％であることが好ましい。なお、着色が目的のメークアップ化粧品中の非水溶性色素組成物の含有量は、５～８０質量％が好ましく、１０～７０質量％がより好ましく、２０～６０質量％が更に好ましい。
非水溶性色素組成物の含有量が上記範囲内であれば、着色性等の機能を有効に発現することができ、かつ化粧品に要求される機能も保持することができる傾向がある。 The content of the water-insoluble dye composition in cosmetics is not particularly limited, and may be appropriately set according to the type of cosmetics. The content of the water-insoluble dye composition in cosmetics is usually 0.1 to 99% by mass, and in general cosmetics, it is preferably 0.1 to 10% by mass. The content of the water-insoluble dye composition in makeup cosmetics intended for coloring is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, and even more preferably 20 to 60% by mass.
If the content of the water-insoluble dye composition is within the above range, there is a tendency that functions such as colorability can be effectively exhibited and functions required for cosmetics can be maintained.
非水溶性色素組成物の含有量が上記範囲内であれば、着色性等の機能を有効に発現することができ、かつ化粧品に要求される機能も保持することができる傾向がある。 The content of the water-insoluble dye composition in cosmetics is not particularly limited, and may be appropriately set according to the type of cosmetics. The content of the water-insoluble dye composition in cosmetics is usually 0.1 to 99% by mass, and in general cosmetics, it is preferably 0.1 to 10% by mass. The content of the water-insoluble dye composition in makeup cosmetics intended for coloring is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, and even more preferably 20 to 60% by mass.
If the content of the water-insoluble dye composition is within the above range, there is a tendency that functions such as colorability can be effectively exhibited and functions required for cosmetics can be maintained.
化粧品は、化粧品の種類に応じて、本発明の非水溶性色素組成物の他、化粧品成分として許容可能な、担体、顔料、油、ステロール、アミノ酸、保湿剤、粉体、着色剤、ｐＨ調整剤、香料、精油、化粧品活性成分、ビタミン、必須脂肪酸、スフィンゴ脂質、セルフタンニング材、賦形剤、充填剤、乳化剤、酸化防止剤、界面活性剤、キレート剤、ゲル化剤、濃厚剤、エモリエント剤、湿潤剤、保湿剤、鉱物、粘度調整剤、流動調整剤、角質溶解剤、レチノイド、ホルモン化合物、アルファヒドロキシ酸、アルファケト酸、抗マイコバクテリア剤、抗真菌剤、抗菌剤、抗ウイルス剤、鎮痛剤、抗アレルギー剤、抗ヒスタミン剤、抗炎症剤、抗刺激剤、抗腫瘍剤、免疫系ブースト剤、免疫系抑制剤、抗アクネ剤、麻酔剤、消毒剤、防虫剤、皮膚冷却化合物、皮膚保護剤、皮膚浸透増強剤、剥脱剤（ｅｘｆｏｌｉａｎｔ）、潤滑剤、芳香剤、染色剤、脱色剤、色素沈着低下剤（ｈｙｐｏｐｉｇｍｅｎｔｉｎｇ ａｇｅｎｔ）、防腐剤、安定剤、医薬品、光安定化剤、及び球形粉末等を含むことができる。
Cosmetics, in addition to the water-insoluble dye composition of the present invention, may contain carriers, pigments, oils, sterols, amino acids, moisturizing agents, powders, colorants, and pH adjusters that are acceptable as cosmetic ingredients, depending on the type of cosmetics. agents, fragrances, essential oils, active cosmetic ingredients, vitamins, essential fatty acids, sphingolipids, self-tanning agents, excipients, fillers, emulsifiers, antioxidants, surfactants, chelating agents, gelling agents, thickeners, emollients agents, humectants, humectants, minerals, viscosity modifiers, rheology modifiers, keratolytic agents, retinoids, hormonal compounds, alpha hydroxy acids, alpha keto acids, antimycobacterial agents, antifungal agents, antibacterial agents, antiviral agents , analgesic, anti-allergic, anti-histamine, anti-inflammatory, anti-irritant, antineoplastic, immune system booster, immune system suppressant, anti-acne, anesthetic, antiseptic, insect repellent, skin cooling compound, skin Protectants, skin penetration enhancers, exfoliants, lubricants, fragrances, dyes, bleaching agents, hypopigmenting agents, preservatives, stabilizers, pharmaceuticals, light stabilizers, and globular Powders and the like can be included.
化粧品は、例えば、非水溶性色素組成物及びその他の化粧品成分を混合することによって製造することができる。また、非水溶性色素組成物を含む化粧品は、化粧品の種類等に応じて、通常の化粧品と同様に使用することができる。
Cosmetics can be produced, for example, by mixing a water-insoluble pigment composition and other cosmetic ingredients. In addition, cosmetics containing a water-insoluble dye composition can be used in the same manner as ordinary cosmetics, depending on the type of cosmetics.
＜プラスチック用途＞
本発明の非水溶性色素組成物は、プラスチック着色用途にも用いることができる。着色プラスチック成形品を得る場合には、例えばポリエチレン、ポリプロピレン等のポリオレフィンやポリ塩化ビニル樹脂等の、射出成形やプレス成形等の熱成形用の熱可塑性樹脂（プラスチック）が用いられるが、本発明の非水溶性色素組成物はこれらの樹脂に従来公知の方法で練り込んで用いることができる。 <Plastic applications>
The water-insoluble dye composition of the present invention can also be used for plastic coloring applications. In the case of obtaining colored plastic molded articles, thermoplastic resins (plastics) for thermoforming such as injection molding and press molding, such as polyolefins such as polyethylene and polypropylene, and polyvinyl chloride resins, are used. The water-insoluble dye composition can be kneaded into these resins by a conventionally known method.
本発明の非水溶性色素組成物は、プラスチック着色用途にも用いることができる。着色プラスチック成形品を得る場合には、例えばポリエチレン、ポリプロピレン等のポリオレフィンやポリ塩化ビニル樹脂等の、射出成形やプレス成形等の熱成形用の熱可塑性樹脂（プラスチック）が用いられるが、本発明の非水溶性色素組成物はこれらの樹脂に従来公知の方法で練り込んで用いることができる。 <Plastic applications>
The water-insoluble dye composition of the present invention can also be used for plastic coloring applications. In the case of obtaining colored plastic molded articles, thermoplastic resins (plastics) for thermoforming such as injection molding and press molding, such as polyolefins such as polyethylene and polypropylene, and polyvinyl chloride resins, are used. The water-insoluble dye composition can be kneaded into these resins by a conventionally known method.
＜トナー用途＞
本発明の非水溶性色素組成物は、トナー用途にも用いることができる。静電荷像現像用トナーの場合には、例えば、ポリエステル樹脂、ポリアミド樹脂、スチレン樹脂、アクリル樹脂等の常温で固形の成膜形成性の熱可塑性樹脂が分散用樹脂として用いられる。 <Toner application>
The water-insoluble dye composition of the present invention can also be used for toner applications. In the case of the toner for electrostatic charge image development, for example, film forming thermoplastic resins such as polyester resins, polyamide resins, styrene resins, and acrylic resins, which are solid at room temperature, are used as dispersing resins.
本発明の非水溶性色素組成物は、トナー用途にも用いることができる。静電荷像現像用トナーの場合には、例えば、ポリエステル樹脂、ポリアミド樹脂、スチレン樹脂、アクリル樹脂等の常温で固形の成膜形成性の熱可塑性樹脂が分散用樹脂として用いられる。 <Toner application>
The water-insoluble dye composition of the present invention can also be used for toner applications. In the case of the toner for electrostatic charge image development, for example, film forming thermoplastic resins such as polyester resins, polyamide resins, styrene resins, and acrylic resins, which are solid at room temperature, are used as dispersing resins.
本発明の非水溶性色素組成物を構成成分として製造される静電荷像現像用トナーは、トナー中に磁性体を含有する一成分色磁性トナー（磁性一成分現像用カラートナー）、磁性体を含有しない非磁性一成分色カラートナー（非磁性一成分現像用カラートナー）、又は、キャリアーを混合した二成分色現像剤用カラートナー（二成分現像用カラートナー）等が挙げられる。
Electrostatic image developing toners produced using the water-insoluble dye composition of the present invention as a constituent component include one-component color magnetic toner containing a magnetic substance in the toner (color toner for magnetic one-component development), Non-magnetic one-component color toner (color toner for non-magnetic one-component development) containing no carrier, or color toner for two-component color developer mixed with carrier (color toner for two-component development).
一成分色磁性トナーは、通常使用されているものと同様に、例えば、着色剤、結着樹脂、磁性粉、電荷制御剤（ＣＣＡ）や離型剤に代表されるその他添加剤等から構成される。
One-component color magnetic toners, like those commonly used, are composed of, for example, colorants, binder resins, magnetic powders, charge control agents (CCA), and other additives such as releasing agents. be.
静電荷現像用トナー中の非水溶性色素組成物の含有量は、特に制限されないが、結着樹脂１００質量部に対して０．５～２５質量部であるのが好ましく、着色剤自身の有する帯電性能を一層顕著ならしめる観点から、結着樹脂１００質量部に対して４～１０質量部であるのがより好ましい。
The content of the water-insoluble dye composition in the toner for electrostatic charge development is not particularly limited, but is preferably 0.5 to 25 parts by mass with respect to 100 parts by mass of the binder resin. From the viewpoint of making the charging performance more remarkable, it is more preferably 4 to 10 parts by mass with respect to 100 parts by mass of the binder resin.
静電荷現像用トナーに用いられる結着樹脂としては、特に制限されず、上記熱可塑性樹脂として例示した樹脂等を用いることができる。また、熱又は圧力の適用下で接着性を示す合成樹脂、天然樹脂、天然ゴム、合成ゴム、合成ワックス等を用いることができる。
The binder resin used in the toner for electrostatic charge development is not particularly limited, and the resins exemplified as the above thermoplastic resins can be used. Synthetic resins, natural resins, natural rubbers, synthetic rubbers, synthetic waxes, etc. that exhibit adhesiveness under the application of heat or pressure can also be used.
以下に実施例を挙げて本発明を更に詳述するが、本発明の範囲はこれらの実施例に限定されるものではない。
Although the present invention will be described in more detail with examples below, the scope of the present invention is not limited to these examples.
（実施例１）
＜水不溶性色素組成物の調製＞
ビーカーに、リナブルーＧ１（ＤＩＣライフテック株式会社製、トレハロース５５％、フィコシアニン色素４０％、クエン酸三ナトリウム５％）２５質量部（フィコシアニン色素１０質量部）、水１００質量部を加え、室温で１０分間攪拌し、フィコシアニンの水溶液を調製した。次いで、フィコシアニンの水溶液に粉末状のιーカラーギナン（東京化成工業株式会社製）０．５質量部を加え、室温（２０℃）で１時間攪拌し、反応溶液を調製した。攪拌をしているイソプロピルアルコール（東京化成工業株式会社製）に、反応溶液を１０分間かけて滴下した後、１５分間攪拌した。得られた固体をろ紙（ＡＤＶＡＮＴＥＣ社製、定性ろ紙Ｎｏ．１、７０ｍｍ）を用いた吸引ろ過で固液分離し、水で洗浄した。ろ別した固形物をビーカーに移し、５０℃で真空加熱乾燥した。乾燥後の粉末をメノー乳鉢ですりつぶした後、目開き１００μｍのふるいに通し、水不溶性色素組成物としての青色の粉体を得た。 (Example 1)
<Preparation of water-insoluble dye composition>
Linablue G1 (manufactured by DIC Lifetech Co., Ltd., 55% trehalose, 40% phycocyanin pigment, 5% trisodium citrate) 25 parts by weight (10 parts by weight phycocyanin pigment) and 100 parts by weight of water are added to a beaker and stirred at room temperature for 10 minutes. After stirring for 1 minute, an aqueous solution of phycocyanin was prepared. Next, 0.5 parts by mass of powdered ι-carrageenan (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the aqueous solution of phycocyanin, and the mixture was stirred at room temperature (20°C) for 1 hour to prepare a reaction solution. After the reaction solution was added dropwise to stirring isopropyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.) over 10 minutes, the mixture was stirred for 15 minutes. The resulting solid was subjected to solid-liquid separation by suction filtration using filter paper (manufactured by ADVANTEC, qualitative filter paper No. 1, 70 mm), and washed with water. The filtered solid matter was transferred to a beaker and vacuum-heated and dried at 50°C. The dried powder was ground in an agate mortar and passed through a sieve with an opening of 100 μm to obtain a blue powder as a water-insoluble dye composition.
＜水不溶性色素組成物の調製＞
ビーカーに、リナブルーＧ１（ＤＩＣライフテック株式会社製、トレハロース５５％、フィコシアニン色素４０％、クエン酸三ナトリウム５％）２５質量部（フィコシアニン色素１０質量部）、水１００質量部を加え、室温で１０分間攪拌し、フィコシアニンの水溶液を調製した。次いで、フィコシアニンの水溶液に粉末状のιーカラーギナン（東京化成工業株式会社製）０．５質量部を加え、室温（２０℃）で１時間攪拌し、反応溶液を調製した。攪拌をしているイソプロピルアルコール（東京化成工業株式会社製）に、反応溶液を１０分間かけて滴下した後、１５分間攪拌した。得られた固体をろ紙（ＡＤＶＡＮＴＥＣ社製、定性ろ紙Ｎｏ．１、７０ｍｍ）を用いた吸引ろ過で固液分離し、水で洗浄した。ろ別した固形物をビーカーに移し、５０℃で真空加熱乾燥した。乾燥後の粉末をメノー乳鉢ですりつぶした後、目開き１００μｍのふるいに通し、水不溶性色素組成物としての青色の粉体を得た。 (Example 1)
<Preparation of water-insoluble dye composition>
Linablue G1 (manufactured by DIC Lifetech Co., Ltd., 55% trehalose, 40% phycocyanin pigment, 5% trisodium citrate) 25 parts by weight (10 parts by weight phycocyanin pigment) and 100 parts by weight of water are added to a beaker and stirred at room temperature for 10 minutes. After stirring for 1 minute, an aqueous solution of phycocyanin was prepared. Next, 0.5 parts by mass of powdered ι-carrageenan (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the aqueous solution of phycocyanin, and the mixture was stirred at room temperature (20°C) for 1 hour to prepare a reaction solution. After the reaction solution was added dropwise to stirring isopropyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.) over 10 minutes, the mixture was stirred for 15 minutes. The resulting solid was subjected to solid-liquid separation by suction filtration using filter paper (manufactured by ADVANTEC, qualitative filter paper No. 1, 70 mm), and washed with water. The filtered solid matter was transferred to a beaker and vacuum-heated and dried at 50°C. The dried powder was ground in an agate mortar and passed through a sieve with an opening of 100 μm to obtain a blue powder as a water-insoluble dye composition.
＜平版オフセット印刷インキの調製＞
得られた粉体を用い、以下のようにして、平版オフセット印刷インキを調製した。 <Preparation of lithographic offset printing ink>
Using the obtained powder, a lithographic offset printing ink was prepared as follows.
得られた粉体を用い、以下のようにして、平版オフセット印刷インキを調製した。 <Preparation of lithographic offset printing ink>
Using the obtained powder, a lithographic offset printing ink was prepared as follows.
＜＜平版オフセット印刷インキ用樹脂ワニスの調製＞＞
ロジン変性フェノール樹脂（重量平均分子量４．５万）４４質量部、大豆油１５質量部を仕込み、窒素気流下で２２０℃に昇温して１．５時間加熱撹拌後、ＡＦソルベント７号（石油系溶剤：ＪＸＴＧエネルギー（株）製）３９．７質量部を加えて、３０分撹拌した後、１４０℃まで冷却した。
冷却後ＡＦソルベント７号で５０％希釈したアルミニウムエチルアセトアセテート・ジイソプロピレート溶液を１．０質量部加えて１６０℃に昇温し１．０時間加熱撹拌後、１４０℃まで冷却し、ＢＨＴ（本州化学（株）社製）０．３質量部を仕込み撹拌した後、平版オフセット印刷インキ用樹脂ワニスを得た。 <<Preparation of resin varnish for lithographic offset printing ink>>
44 parts by mass of rosin-modified phenolic resin (weight average molecular weight 45,000) and 15 parts by mass of soybean oil were charged, heated to 220 ° C. under a nitrogen stream, heated and stirred for 1.5 hours, and then AF Solvent No. 7 (petroleum System solvent: 39.7 parts by mass of JXTG Energy Co., Ltd. was added, stirred for 30 minutes, and then cooled to 140°C.
After cooling, 1.0 parts by mass of aluminum ethyl acetoacetate diisopropylate solution diluted 50% with AF Solvent No. 7 was added, the temperature was raised to 160 ° C., and after heating and stirring for 1.0 hours, cooled to 140 ° C., BHT ( Honshu Kagaku Co., Ltd.) was charged and stirred to obtain a resin varnish for lithographic offset printing ink.
ロジン変性フェノール樹脂（重量平均分子量４．５万）４４質量部、大豆油１５質量部を仕込み、窒素気流下で２２０℃に昇温して１．５時間加熱撹拌後、ＡＦソルベント７号（石油系溶剤：ＪＸＴＧエネルギー（株）製）３９．７質量部を加えて、３０分撹拌した後、１４０℃まで冷却した。
冷却後ＡＦソルベント７号で５０％希釈したアルミニウムエチルアセトアセテート・ジイソプロピレート溶液を１．０質量部加えて１６０℃に昇温し１．０時間加熱撹拌後、１４０℃まで冷却し、ＢＨＴ（本州化学（株）社製）０．３質量部を仕込み撹拌した後、平版オフセット印刷インキ用樹脂ワニスを得た。 <<Preparation of resin varnish for lithographic offset printing ink>>
44 parts by mass of rosin-modified phenolic resin (weight average molecular weight 45,000) and 15 parts by mass of soybean oil were charged, heated to 220 ° C. under a nitrogen stream, heated and stirred for 1.5 hours, and then AF Solvent No. 7 (petroleum System solvent: 39.7 parts by mass of JXTG Energy Co., Ltd. was added, stirred for 30 minutes, and then cooled to 140°C.
After cooling, 1.0 parts by mass of aluminum ethyl acetoacetate diisopropylate solution diluted 50% with AF Solvent No. 7 was added, the temperature was raised to 160 ° C., and after heating and stirring for 1.0 hours, cooled to 140 ° C., BHT ( Honshu Kagaku Co., Ltd.) was charged and stirred to obtain a resin varnish for lithographic offset printing ink.
＜＜平版オフセット印刷インキの調製＞＞
下記の配合割合で、３本ロールミルを用いて練肉し、平版オフセット印刷インキを得た。
〔平版オフセット印刷インキの配合量〕
平版オフセット印刷インキ用樹脂ワニス ６５部
水不溶性色素組成物 １６部
ＡＦソルベント７号 １９部 <<Preparation of lithographic offset printing ink>>
The blending ratio below was kneaded using a three-roll mill to obtain a lithographic offset printing ink.
[Combination amount of lithographic offset printing ink]
Resin varnish for lithographic offset printing ink 65 parts Water-insoluble pigment composition 16 parts AF Solvent No. 7 19 parts
下記の配合割合で、３本ロールミルを用いて練肉し、平版オフセット印刷インキを得た。
〔平版オフセット印刷インキの配合量〕
平版オフセット印刷インキ用樹脂ワニス ６５部
水不溶性色素組成物 １６部
ＡＦソルベント７号 １９部 <<Preparation of lithographic offset printing ink>>
The blending ratio below was kneaded using a three-roll mill to obtain a lithographic offset printing ink.
[Combination amount of lithographic offset printing ink]
Resin varnish for lithographic offset printing ink 65 parts Water-insoluble pigment composition 16 parts AF Solvent No. 7 19 parts
＜インキ展色物の調製＞
得られた平版オフセット印刷インキを、ヘラを用いてトップコート紙に展色した後、ドライヤーで乾燥し、インキ展色物を得た。 <Preparation of Ink Exhibit>
The resulting lithographic offset printing ink was spread on a topcoat paper using a spatula, and then dried with a drier to obtain an ink spread.
得られた平版オフセット印刷インキを、ヘラを用いてトップコート紙に展色した後、ドライヤーで乾燥し、インキ展色物を得た。 <Preparation of Ink Exhibit>
The resulting lithographic offset printing ink was spread on a topcoat paper using a spatula, and then dried with a drier to obtain an ink spread.
（実施例２～５）
フィコシアニン色素及びιーカラーギナンを表１に記載の配合量に変更した以外は、実施例１と同様の方法で、水不溶性色素組成物としての青色の粉体を得た。得られた粉体を用い、実施例１と同様の方法で、平版オフセット印刷インキ及びインキ展色物を調製した。 (Examples 2-5)
A blue powder as a water-insoluble pigment composition was obtained in the same manner as in Example 1, except that the amounts of phycocyanin pigment and ι-carrageenan were changed to those shown in Table 1. Using the obtained powder, in the same manner as in Example 1, a lithographic offset printing ink and an ink development were prepared.
フィコシアニン色素及びιーカラーギナンを表１に記載の配合量に変更した以外は、実施例１と同様の方法で、水不溶性色素組成物としての青色の粉体を得た。得られた粉体を用い、実施例１と同様の方法で、平版オフセット印刷インキ及びインキ展色物を調製した。 (Examples 2-5)
A blue powder as a water-insoluble pigment composition was obtained in the same manner as in Example 1, except that the amounts of phycocyanin pigment and ι-carrageenan were changed to those shown in Table 1. Using the obtained powder, in the same manner as in Example 1, a lithographic offset printing ink and an ink development were prepared.
（比較例１）
リナブルーＧ１（ＤＩＣライフテック株式会社製、トレハロース５５％、フィコシアニン色素４０％、クエン酸三ナトリウム５％）１質量部を、水１００質量部に添加し、５分間攪拌し、分散液を調製した。分散液をろ紙上に１滴滴下したところ、滴下部分を中心に同心円状に青色の液が均一に広がっていく様子が観察された。これは分散液において、リナブルーＧ１が水に溶解していることを示しており、フィコシアニンは水に可溶であった。 (Comparative example 1)
1 part by mass of Linablue G1 (55% trehalose, 40% phycocyanin pigment, 5% trisodium citrate, manufactured by DIC Lifetech Co., Ltd.) was added to 100 parts by mass of water and stirred for 5 minutes to prepare a dispersion. When one drop of the dispersion liquid was dropped onto the filter paper, it was observed that the blue liquid spread uniformly concentrically around the dropped portion. This indicates that Linablue G1 was dissolved in water in the dispersion, and phycocyanin was soluble in water.
リナブルーＧ１（ＤＩＣライフテック株式会社製、トレハロース５５％、フィコシアニン色素４０％、クエン酸三ナトリウム５％）１質量部を、水１００質量部に添加し、５分間攪拌し、分散液を調製した。分散液をろ紙上に１滴滴下したところ、滴下部分を中心に同心円状に青色の液が均一に広がっていく様子が観察された。これは分散液において、リナブルーＧ１が水に溶解していることを示しており、フィコシアニンは水に可溶であった。 (Comparative example 1)
1 part by mass of Linablue G1 (55% trehalose, 40% phycocyanin pigment, 5% trisodium citrate, manufactured by DIC Lifetech Co., Ltd.) was added to 100 parts by mass of water and stirred for 5 minutes to prepare a dispersion. When one drop of the dispersion liquid was dropped onto the filter paper, it was observed that the blue liquid spread uniformly concentrically around the dropped portion. This indicates that Linablue G1 was dissolved in water in the dispersion, and phycocyanin was soluble in water.
（評価及び測定）
実施例１～５の粉体について、下記の方法で水不溶性評価を行った。また、実施例１～５の粉体を用いた平版オフセットインキによるインキ展色物の色相を測定した。 (Evaluation and measurement)
The powders of Examples 1 to 5 were evaluated for water insolubility by the following method. Further, the hues of the ink-developed products obtained by using the lithographic offset inks using the powders of Examples 1 to 5 were measured.
実施例１～５の粉体について、下記の方法で水不溶性評価を行った。また、実施例１～５の粉体を用いた平版オフセットインキによるインキ展色物の色相を測定した。 (Evaluation and measurement)
The powders of Examples 1 to 5 were evaluated for water insolubility by the following method. Further, the hues of the ink-developed products obtained by using the lithographic offset inks using the powders of Examples 1 to 5 were measured.
＜水不溶性評価＞
実施例１～５の粉体１０ｍｇを水１．０ｇに添加し、５分間攪拌し、分散液を調製した。分散得液を濾紙上に１滴滴下したところ、滴下部分は円状に青く呈色し、その後同心円状に無色透明の液が広がっていく様子が観察された。初めに円状に青く呈色した部分は水に不溶化した粉体、その後同心円状に透明の液が広がった部分は水であり、実施例１～５の粉体は水に不溶であることが分かった。 <Water-insoluble evaluation>
10 mg of the powders of Examples 1 to 5 were added to 1.0 g of water and stirred for 5 minutes to prepare dispersions. When one drop of the dispersed liquid was dropped onto the filter paper, the dropped portion was circularly colored blue, and then it was observed that the colorless and transparent liquid spread concentrically. The first circle-shaped blue colored portion is the powder insoluble in water, and the portion where the transparent liquid spreads concentrically after that is water, and the powders of Examples 1 to 5 are insoluble in water. Do you get it.
実施例１～５の粉体１０ｍｇを水１．０ｇに添加し、５分間攪拌し、分散液を調製した。分散得液を濾紙上に１滴滴下したところ、滴下部分は円状に青く呈色し、その後同心円状に無色透明の液が広がっていく様子が観察された。初めに円状に青く呈色した部分は水に不溶化した粉体、その後同心円状に透明の液が広がった部分は水であり、実施例１～５の粉体は水に不溶であることが分かった。 <Water-insoluble evaluation>
10 mg of the powders of Examples 1 to 5 were added to 1.0 g of water and stirred for 5 minutes to prepare dispersions. When one drop of the dispersed liquid was dropped onto the filter paper, the dropped portion was circularly colored blue, and then it was observed that the colorless and transparent liquid spread concentrically. The first circle-shaped blue colored portion is the powder insoluble in water, and the portion where the transparent liquid spreads concentrically after that is water, and the powders of Examples 1 to 5 are insoluble in water. Do you get it.
＜印刷インキ展色物の色相の測定＞
分光測色計（Ｘ‐ｒｉｔｅ社製ＳｐｅｃｔｒｏＥｙｅ）を用い、観測光源Ｄ５０、観測視野２°の条件で、ＣＩＥＬＡＢ色空間で印刷インキ展色物の色相（Ｌ＊値、ａ＊値、ｂ＊値）を測定した。得られた測定値をもとに、下記式を用いて色相角ｈを算出した。 <Measurement of Hue of Printing Ink Exhibit>
Using a spectrophotometer (SpectroEye manufactured by X-rite), under the conditions of an observation light source of D50 and an observation field of view of 2°, the hue (L* value, a* value, b* value) of the printed ink exhibit in the CIELAB color space ) was measured. Based on the measured values obtained, the hue angle h was calculated using the following formula.
分光測色計（Ｘ‐ｒｉｔｅ社製ＳｐｅｃｔｒｏＥｙｅ）を用い、観測光源Ｄ５０、観測視野２°の条件で、ＣＩＥＬＡＢ色空間で印刷インキ展色物の色相（Ｌ＊値、ａ＊値、ｂ＊値）を測定した。得られた測定値をもとに、下記式を用いて色相角ｈを算出した。 <Measurement of Hue of Printing Ink Exhibit>
Using a spectrophotometer (SpectroEye manufactured by X-rite), under the conditions of an observation light source of D50 and an observation field of view of 2°, the hue (L* value, a* value, b* value) of the printed ink exhibit in the CIELAB color space ) was measured. Based on the measured values obtained, the hue angle h was calculated using the following formula.
印刷インキ展色物の色相の測定の結果を表１に示す。
Table 1 shows the results of the hue measurements of the printing ink developments.
実施例１～５の本発明の非水溶性色素組成物は、水に不溶性であったが、比較例１のフィコシアニンは水溶性であった。また、実施例１～５の非水溶性色素組成物を用いた印刷インキは、表１に示すように、鮮明な青色を有することが分かった。中でも、実施例１～４の非水溶性色素組成物を用いた印刷インキは、特に鮮明な青色を有することが分かった。
The water-insoluble pigment compositions of the present invention of Examples 1-5 were insoluble in water, but phycocyanin of Comparative Example 1 was water-soluble. Also, as shown in Table 1, the printing inks using the water-insoluble dye compositions of Examples 1 to 5 were found to have a vivid blue color. Among them, it was found that the printing inks using the water-insoluble dye compositions of Examples 1 to 4 had a particularly clear blue color.
Claims (5)
- フィコシアニンと、カラギーナンとが複合化してなる、非水溶性色素組成物。 A water-insoluble pigment composition composed of a complex of phycocyanin and carrageenan.
- 前記非水溶性色素組成物における前記フィコシアニンと前記カラギーナンとの組成比が、質量比で、１００：１～１００：７５である、請求項１に記載の非水溶性色素組成物。 The water-insoluble pigment composition according to claim 1, wherein the composition ratio of the phycocyanin and the carrageenan in the water-insoluble pigment composition is 100:1 to 100:75 in mass ratio.
- 前記フィコシアニンが藍藻類由来のフィコシアニンである、請求項１に記載の非水溶性色素組成物。 The water-insoluble pigment composition according to claim 1, wherein the phycocyanin is derived from blue-green algae.
- 前記藍藻類がスピルリナ属の藍藻類である、請求項３に記載の非水溶性色素組成物。 The water-insoluble pigment composition according to claim 3, wherein the blue-green algae belong to the genus Spirulina.
- 前記非水溶性色素組成物は、食品、化粧品、医薬品、文具、筆記部、印刷インキ、インクジェットインキ、塗料、プラスチック着色剤、又はトナー用の組成物である、請求項１～４のいずれか一項に記載の非水溶性色素組成物。
5. The water-insoluble pigment composition according to any one of claims 1 to 4, which is a composition for foods, cosmetics, pharmaceuticals, stationery, writing parts, printing inks, inkjet inks, paints, plastic colorants, or toners. The water-insoluble dye composition according to the item.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022578787A JPWO2023281936A1 (en) | 2021-07-06 | 2022-05-30 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021112070 | 2021-07-06 | ||
| JP2021-112070 | 2021-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2023281936A1 true WO2023281936A1 (en) | 2023-01-12 |
Family
ID=84800590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2022/021893 WO2023281936A1 (en) | 2021-07-06 | 2022-05-30 | Water-insoluble pigment composition |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPWO2023281936A1 (en) |
| WO (1) | WO2023281936A1 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS626691A (en) * | 1985-07-02 | 1987-01-13 | Dainippon Ink & Chem Inc | Phycocyanin pigment a from blue-green alga, production and use thereof |
| CN111067010A (en) * | 2019-12-16 | 2020-04-28 | 上海嘉萃生物科技有限公司 | Heat-resistant phycocyanin and preparation method thereof |
| EP3692803A1 (en) * | 2019-01-18 | 2020-08-12 | GNT Group B.V. | A composition comprising spirulina-extract |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4570005B2 (en) * | 2001-09-19 | 2010-10-27 | 株式会社リコー | Image recording substrate, image recording material, and image recording method thereof |
| JP2010215687A (en) * | 2009-03-13 | 2010-09-30 | Toyo Ink Mfg Co Ltd | Edible ink for inkjet and method for manufacturing the same |
| DE102019006869A1 (en) * | 2019-10-02 | 2021-04-08 | Merck Patent Gmbh | Interference pigments |
-
2022
- 2022-05-30 WO PCT/JP2022/021893 patent/WO2023281936A1/en active Application Filing
- 2022-05-30 JP JP2022578787A patent/JPWO2023281936A1/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS626691A (en) * | 1985-07-02 | 1987-01-13 | Dainippon Ink & Chem Inc | Phycocyanin pigment a from blue-green alga, production and use thereof |
| EP3692803A1 (en) * | 2019-01-18 | 2020-08-12 | GNT Group B.V. | A composition comprising spirulina-extract |
| CN111067010A (en) * | 2019-12-16 | 2020-04-28 | 上海嘉萃生物科技有限公司 | Heat-resistant phycocyanin and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| HADIYANTO H., CHRISTWARDANA MARCELINUS, SUZERY MEINY, SUTANTO HERI, NILAMSARI AYU MUNTI, YUNANDA ARGINO: "Effects of Carrageenan and Chitosan as Coating Materials on the Thermal Degradation of Microencapsulated Phycocyanin from Spirulina sp", INTERNATIONAL JOURNAL OF FOOD ENGINEERING, DE GRUYTER, 27 March 2019 (2019-03-27), pages 1 - 15, XP093005990, Retrieved from the Internet <URL:https://eprints2.undip.ac.id/id/eprint/203/1/turnitin_c3.pdf> [retrieved on 20221207], DOI: 10.1515/ijfe-2018-0290 * |
| LI YING; ZHANG ZHONG; ABBASPOURRAD ALIREZA: "Improved thermal stability of phycocyanin under acidic conditions by forming soluble complexes with polysaccharides", FOOD HYDROCOLLOIDS, ELSEVIER BV, NL, vol. 119, 23 April 2021 (2021-04-23), NL , XP086604844, ISSN: 0268-005X, DOI: 10.1016/j.foodhyd.2021.106852 * |
| ZHANG ZHONG, CHO SUE, DADMOHAMMADI YOUNAS, LI YING, ABBASPOURRAD ALIREZA: "Improvement of the storage stability of C-phycocyanin in beverages by high-pressure processing", FOOD HYDROCOLLOIDS, ELSEVIER BV, NL, vol. 110, 1 January 2021 (2021-01-01), NL , pages 106055, XP093022591, ISSN: 0268-005X, DOI: 10.1016/j.foodhyd.2020.106055 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2023281936A1 (en) | 2023-01-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2459847C2 (en) | Novel 2,9-dichloroquinacridone in plate-like form | |
| JP2019178334A (en) | Pigment mixture | |
| US8758732B2 (en) | Makeup composition comprising a black colour mixture of pigments | |
| DE3923953A1 (en) | DYE-CONTAINING PEARL NUT PIGMENT AND COSMETIC COMPOSITION HAVING A SAME THEREOF | |
| JP4620469B2 (en) | Optically variable pigment with asymmetric layer structure | |
| CN109651851A (en) | The inorganic-organic hybridization nano pigment and preparation method of natural botanical source and application | |
| JP7060177B2 (en) | Phycocyanin pigment composition | |
| WO2023281936A1 (en) | Water-insoluble pigment composition | |
| JPH1112493A (en) | Composite powder and composition containing the same | |
| JP2630428B2 (en) | Color pigments and cosmetics containing the same | |
| KR100993414B1 (en) | Method of Manufacturing Natural dye Stabilized and Natural dye manufactured by the same | |
| JPH04332766A (en) | Composite colored pearl-lustrous pigment and cosmetic containing the same | |
| JP7552925B2 (en) | Water-insoluble, oil-insoluble pigment composition | |
| JP7552924B2 (en) | Water-insoluble dye composition | |
| JP7552927B2 (en) | Water-insoluble dye composition | |
| JP6348690B2 (en) | Highly functional color material and manufacturing method thereof | |
| JPH0611871B2 (en) | Flake pigment with organic pigment and its manufacturing method | |
| JP2010513579A (en) | New rod shape C.I. I. Pigment Bio Red 37 | |
| JP3645472B2 (en) | Spherical composite powder and cosmetics containing the same | |
| US20230052291A1 (en) | Cellulose nanocrystal effect pigments for cosmetic applications | |
| JP2002332211A (en) | Colored spherical polyamide powder and cosmetic comprising the same | |
| WO2024135375A1 (en) | Water-insoluble pigment composition | |
| JP4443134B2 (en) | Coloring material | |
| JPH0454110A (en) | Color pigment and cosmetic containing the same pigment | |
| JPS63205370A (en) | Coloring material composition containing gypsum and production thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENP | Entry into the national phase |
Ref document number: 2022578787 Country of ref document: JP Kind code of ref document: A |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22837357 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 22837357 Country of ref document: EP Kind code of ref document: A1 |