JPS62195053A - Pigment dispersant - Google Patents
Pigment dispersantInfo
- Publication number
- JPS62195053A JPS62195053A JP61035267A JP3526786A JPS62195053A JP S62195053 A JPS62195053 A JP S62195053A JP 61035267 A JP61035267 A JP 61035267A JP 3526786 A JP3526786 A JP 3526786A JP S62195053 A JPS62195053 A JP S62195053A
- Authority
- JP
- Japan
- Prior art keywords
- rosin
- pigment
- parts
- series
- dispersant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 118
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 59
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 51
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims abstract description 51
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims abstract description 51
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 5
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 claims description 4
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical class C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 claims description 3
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical class C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 claims description 3
- XQGDNRFLRLSUFQ-UHFFFAOYSA-N 2H-pyranthren-1-one Chemical class C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 XQGDNRFLRLSUFQ-UHFFFAOYSA-N 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 150000005125 dioxazines Chemical class 0.000 claims description 2
- AWIZFKXFPHTRHN-UHFFFAOYSA-N naphtho[2,3-f]quinoline Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 AWIZFKXFPHTRHN-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 18
- 238000006243 chemical reaction Methods 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 17
- 238000004040 coloring Methods 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 5
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 abstract description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract description 2
- 229910005948 SO2Cl Inorganic materials 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 31
- 238000004519 manufacturing process Methods 0.000 description 31
- 239000006185 dispersion Substances 0.000 description 24
- 239000003973 paint Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000002687 nonaqueous vehicle Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- 239000012860 organic pigment Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229920000180 alkyd Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000011941 Tilia x europaea Nutrition 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000001023 inorganic pigment Substances 0.000 description 3
- 239000004571 lime Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000019239 indanthrene blue RS Nutrition 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- SMNNDVUKAKPGDD-UHFFFAOYSA-N 2-butylbenzoic acid Chemical group CCCCC1=CC=CC=C1C(O)=O SMNNDVUKAKPGDD-UHFFFAOYSA-N 0.000 description 1
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 101150050192 PIGM gene Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 flavanthrone series Chemical class 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔発明の目的〕
（産業上の利用分野）
本発明は使用適性、特に非集合性、流動性に優れた非水
系顔料分散液等を提供する顔料分散剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Object of the Invention] (Industrial Field of Application) The present invention relates to a pigment dispersant that provides a non-aqueous pigment dispersion etc. that is suitable for use, particularly excellent in non-agglomeration and fluidity.
（従来の技術）
一般に各種コーティングまたはインキ組成物中において
鮮明な色網と高い着色力を発揮する実用上有用な顔料は
微細な粒子からなっている。しかしながら顔料の微細な
粒子は、オフセントインキ、グラビアインキおよび塗料
のような非水性ビヒクルに分散する場合、安定な分散体
を得ることが難しく、製造作業上および得られる製品の
価値に重要な影響を及ぼす種々の問題を引き起こすこと
が知られている。(Prior Art) Practically useful pigments that exhibit clear color networks and high tinting power in various coating or ink compositions generally consist of fine particles. However, fine particles of pigments make it difficult to obtain stable dispersions when dispersed in non-aqueous vehicles such as offset inks, gravure inks and paints, which has an important impact on manufacturing operations and the value of the resulting products. It is known to cause various problems.
例えば、微細な粒子からなる顔料を含む分散体は往々に
して高粘度を示し製品の分散機からの取出し。For example, dispersions containing pigments consisting of fine particles often exhibit high viscosities that make it difficult to remove the product from the disperser.
輸送が困難となるばかりでなく、更に悪い場合は貯蔵中
にゲル化を起し使用困難となることがある。また異種の
顔料を混合して使用する場合、′＃：集による色分れや
、沈降などの現象により展色物において色むらや著しい
着色力の低下となって現われることがある。さらに展色
物の塗膜表面に関しては光沢の低下、レヘリング不良等
の状態不良を生ずることがある。Not only is transportation difficult, but in worse cases, gelation may occur during storage, making it difficult to use. In addition, when different types of pigments are mixed and used, phenomena such as color separation and sedimentation may appear in the developed product as color unevenness and a significant decrease in coloring power. Furthermore, the surface of the paint film of the developed product may suffer from poor conditions such as reduced gloss and poor leveling.
また、顔料の分散とは直接関係しないが一部の有機顔料
では顔料の結晶状態の変化を伴う現象がある。Further, although not directly related to pigment dispersion, some organic pigments experience a phenomenon that involves a change in the crystalline state of the pigment.
すなわちオフセットインキ、グラビアインキおよび塗料
等の非水性ビヒクル中でエネルギー的に不安定な顔料の
結晶粒子がその大きさ、形態を変化させて安定状態に移
行するため展色物において著しい色相の変化１着色力の
減少、粗粒子の発生等により商品価値を損うことがある
。In other words, in non-aqueous vehicles such as offset inks, gravure inks, and paints, pigment crystal particles, which are energetically unstable, change their size and shape and shift to a stable state, resulting in a significant change in hue in the color spread1. Product value may be impaired due to a decrease in coloring power, generation of coarse particles, etc.
以上のような種々の問題点を解決するためにこれまでも
銅フタロシアニンおよびキナクリドン系顔料を中心とし
て数多くの提案がされている。In order to solve the various problems mentioned above, many proposals have been made so far, centering on copper phthalocyanine and quinacridone pigments.
その内容を技術的手法から分類すると大きく次のような
２つに分けられる。The content can be broadly divided into the following two categories based on technical methods.
第１法はＵＳＰ３３７０９７１およびＵＳＰ２９６５５
１１号公報に見られるように酸化ケイ素、酸化アルミニ
ウムおよび第３級ブチル安息香酸のように無色の化合物
で顔料粒子表面を被覆するものである。Act 1 is USP 3370971 and USP 29655
As seen in Publication No. 11, the surface of pigment particles is coated with a colorless compound such as silicon oxide, aluminum oxide, and tertiary butylbenzoic acid.
第２法は特公昭４１−２４６６号公報およびＵＳＰ ２
８５５４．０３号公報に代表されるように有機顔料を母
体骨格とし側鎖にスルフォン基、スルフォンアミド基、
アミノメチル基、フタルイミドメチル基等の置換基を導
入して得られる化合物を混合する方法である。The second law is published in Japanese Patent Publication No. 41-2466 and USP 2.
As typified by Publication No. 8554.03, the base skeleton is an organic pigment, and the side chain has a sulfone group, a sulfonamide group,
This is a method of mixing compounds obtained by introducing substituents such as aminomethyl groups and phthalimidomethyl groups.
第２の方法は第１の方法に比べ非水性ビヒクル中での顔
料の非集合性、結晶安定性等に関する効果が著しく大き
くまた顔料組成物の製造の容易さから判断しても非常に
有利な方法であるが、それぞれの化合物の効果は使用す
るビヒクルの組成に大きく影響され、全てのビヒクルに
有効な化合物は見出されていない。とくにオフセントイ
ンキに対して効果のある化合物はほとんど知られていな
い。Compared to the first method, the second method has a significantly greater effect on pigment disaggregation, crystal stability, etc. in a non-aqueous vehicle, and is also very advantageous judging from the ease of manufacturing the pigment composition. However, the effectiveness of each compound is greatly influenced by the composition of the vehicle used, and no compound has been found that is effective in all vehicles. In particular, few compounds are known that are effective against off-center inks.
（発明が解決しようとする問題点）
本発明は、オフセソインキ、グラビアインキおよび塗料
等の非水系分散液、とくにオフセットインキでの使用適
性に有効な化合物を顔料分散剤として使用するものであ
る。(Problems to be Solved by the Invention) The present invention uses, as a pigment dispersant, a compound that is effective for use in non-aqueous dispersions such as offset inks, gravure inks, and paints, particularly in offset inks.
（本題を解決するための手段）
本発明は、カルボキシル基またはアミノ基と反応し得る
官能基を有する有機色素または有機色素誘導体と、カル
ボキシル基またはアミノ基を有するロジンまたはロジン
誘導体（以下、ロジン類と総称する）とが反応してなる
顔料分散剤である。(Means for Solving the Problem) The present invention provides an organic dye or an organic dye derivative having a functional group capable of reacting with a carboxyl group or an amino group, and a rosin or rosin derivative (hereinafter referred to as rosin) having a carboxyl group or an amino group. It is a pigment dispersant formed by reacting with (collectively referred to as).
本発明において、有機色素は例えばアントラキノン系、
アゾ系、キナクリドン系、ジオキサジン系。In the present invention, organic dyes include, for example, anthraquinone,
Azo series, quinacridone series, dioxazine series.
アントラピリジン系、アンサンスロン系、インダンスロ
ン系、フラバンスロン系、ピランスロン系、ペリノン系
、ペリレン系およびチオインジゴ系等であり、ロジン類
は例えばロジンアミン、ロジン（ガムロジン、ウッドロ
ジン、トール油ロジン）、マレイン化ロジン、不均化ロ
ジン、重合ロジン、水添ロジン、酸化ロジンおよびロジ
ン変性フェノール樹脂等である。These include anthrapyridine series, anthanthrone series, indanthrone series, flavanthrone series, pyranthrone series, perinone series, perylene series, and thioindigo series, and rosins include rosin amines, rosins (gum rosin, wood rosin, tall oil rosin), maleic rosins, etc. These include oxidized rosin, disproportionated rosin, polymerized rosin, hydrogenated rosin, oxidized rosin, and rosin-modified phenolic resin.
本発明における顔料分散剤の作用機構は明らかではない
が、実施例で示すようにオフセットインキ。Although the mechanism of action of the pigment dispersant in the present invention is not clear, it can be used in offset inks as shown in Examples.
グラビアインキおよび塗料等の非水性ビヒクルの中で、
とくに従来、効果の大きい化合物がほとんどなかったオ
フセットインキに対しても著しい効果を示すことから顔
料分散剤に化学結合しているロジン類とオフセントイン
キに含まれるロジン変性樹脂等との間に相互作用が生じ
ていると推定できる。In non-aqueous vehicles such as gravure inks and paints,
In particular, it shows a remarkable effect even on offset inks, for which there have been few highly effective compounds, so there is a mutual interaction between rosins chemically bonded to pigment dispersants and rosin-modified resins contained in offset inks. It can be assumed that this effect is occurring.
従って本発明において、カルボキシル基またはアミノ基
と反応し得る官能基は９例えば−３ＯｉＣＡ 。Therefore, in the present invention, the functional group that can react with a carboxyl group or an amino group is 9, for example -3OiCA.
−ＣｏＣＩｌ、−ＣＨユＣＩ！、および−ＣＨユＮ Ｈ
ＣＯＣＨ。-CoCIl, -CHYUCI! , and -CH YuN H
COCH.
ＣＺ等であるが、有機色素とロジン類とが化学結合し得
れば、その結合基の種類は本質的にその効果に大きく影
響することはない。CZ, etc., but as long as the organic dye and the rosin can be chemically bonded, the type of the bonding group essentially does not greatly affect the effect.
本発明の顔料分散剤の製造方法は常法により有機色素に
カルボキシル基またはアミノ基と反応し得る置換基を導
入した後に、水、アルコール、アセトン、ジオキサンお
よびＮ、Ｎ−ジメチルホルムアミド等の反応溶媒中で、
場合によってはアルカリ触媒を添加してロジン類と反応
させ、溶媒を除去するのが、一般的であるが、アゾ系の
ような有機色素においてはジアゾ成分または力・７プラ
一成分にロジン類を化学反応させた後にカップリングす
る方法が工業的に有利である。The method for producing the pigment dispersant of the present invention involves introducing a substituent capable of reacting with a carboxyl group or an amino group into an organic pigment by a conventional method, and then using a reaction solvent such as water, alcohol, acetone, dioxane, and N,N-dimethylformamide. Inside,
In some cases, it is common to add an alkali catalyst to react with rosin and remove the solvent, but in the case of organic dyes such as azo, rosin is added to the diazo component or the rosin component. A method of coupling after a chemical reaction is industrially advantageous.
本発明で得られる顔料分散剤は、一般に市販されている
すべての顔料に優れた分散効果を発揮する。The pigment dispersant obtained in the present invention exhibits an excellent dispersion effect on all pigments that are generally commercially available.
例えば可溶性および不溶性アゾ顔料、縮合アゾ顔料６一
等のアゾ系顔料、フタロシアニン系顔料、キナクリドン
系顔料、イソインドリノン系顔料、ペリレン・ペリノン
系顔料、ジオキサジン系顔料、建染染料系顔料、塩基性
染料系顔料等の有機顔料およびカーボンブランク、酸化
チタン、黄鉛、カドミウムエロー、カドミウムレッド、
弁柄、鉄黒、亜鉛華、紺青。For example, soluble and insoluble azo pigments, azo pigments such as condensed azo pigments 6, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, perylene/perinone pigments, dioxazine pigments, vat dye pigments, basic Organic pigments such as dye pigments, carbon blanks, titanium oxide, yellow lead, cadmium yellow, cadmium red,
Bengara, iron black, zinc oxide, dark blue.
群青等の無機顔料に用いることができる。It can be used for inorganic pigments such as ultramarine blue.
本発明で得られる顔料分散剤の顔料に対する配合は、顔
料１００重量部に対し、０．３〜３０重量部が好ましい
。０．３重量部より少ないと本発明で得られる顔料分散
剤の効果が得られず、また、３０重量部より多く用いて
も用いた分の効果が得られない。The content of the pigment dispersant obtained in the present invention in the pigment is preferably 0.3 to 30 parts by weight per 100 parts by weight of the pigment. If it is less than 0.3 parts by weight, the effect of the pigment dispersant obtained in the present invention cannot be obtained, and even if it is used in an amount greater than 30 parts by weight, the effect of the amount used cannot be obtained.
本発明にかかわる分散剤の使用方法としては９例えば次
のような方法がある。There are 9 methods for using the dispersant according to the present invention, for example, as follows.
■、顔料と分散剤を予め混合して得られる顔料組成物を
非水系ビヒクルに添加して分散する。(2) A pigment composition obtained by pre-mixing a pigment and a dispersant is added to a non-aqueous vehicle and dispersed.
２、非水系ビヒクルに顔料と分散剤を別々に添加して分
解する。2. Pigment and dispersant are added separately to a non-aqueous vehicle and decomposed.
３、非水系ビヒクルに顔料と分散剤を予め別々に分散し
得られた分散体を混合する。3. The pigment and the dispersant are separately dispersed in advance in a non-aqueous vehicle, and the resulting dispersion is mixed.
この場合分散剤を溶剤のみで分散しても良い。In this case, the dispersant may be dispersed using only a solvent.
４、非水系ビヒクルに顔料を分散した後、得られた分散
体に分散剤を添加する。4. After dispersing the pigment in a non-aqueous vehicle, a dispersant is added to the resulting dispersion.
等の４つの方法があり、これらのいずれによっても目的
とする効果が得られる。There are four methods, and any of these methods can achieve the desired effect.
上記１で示した顔料組成物の調整法としては、顔料粉末
と本発明に関わる分散剤の粉末を単に混合しても充分目
的とする効果が得られるが、ニーダ−。As a method for preparing the pigment composition shown in 1 above, the desired effect can be obtained by simply mixing the pigment powder and the powder of the dispersant related to the present invention, but a kneader is used.
ロール、アトライター、スーパーミル、各種粉砕機等に
より機械的に混合するか、顔料の水または有機溶媒によ
るサスペンション系に本発明に係わる分散剤を含む溶液
を添加し、顔料表面に分散剤を沈着させるか、硫酸等の
強い溶解力をもつ溶媒に有機顔料と分散剤を共溶解して
水等の貧溶媒により共沈させる等の緊密な混合法を行え
ば更に良好な結果を得ることができる。The dispersant is deposited on the surface of the pigment by mechanically mixing with a roll, attritor, super mill, various types of pulverizers, etc., or by adding a solution containing the dispersant according to the present invention to a pigment suspension system of water or an organic solvent. Better results can be obtained by using an intimate mixing method, such as co-dissolving the organic pigment and dispersant in a solvent with strong dissolving power such as sulfuric acid, and co-precipitating with a poor solvent such as water. .
また、上記２〜４で示した。顔料と分散剤との使用にお
いては、非水系ビヒクルまたは溶剤中への顔料あるいは
分散剤の分散、これらの混合等に分散機械としてディシ
ルバー、ハイスピードミキサー、ホモミキサー、ニーダ
−、ロールミル、サンドミル。Further, as shown in 2 to 4 above. When using pigments and dispersants, dispersion machines such as dispersion machines, high-speed mixers, homo mixers, kneaders, roll mills, and sand mills are used for dispersing pigments or dispersants in non-aqueous vehicles or solvents, and mixing them.
アトライター等を使用することにより顔料の良好な分散
ができる。Good dispersion of the pigment can be achieved by using an attritor or the like.
（作 用）
本発明の顔料分散剤の作用機構は明らかではないが、非
水性ビヒクル中で非集合性、流動性などに著しい効果が
認められるのは、顔料粒子の表面に吸着した顔料分散剤
と非水性ビヒクルに含まれる樹脂成分との間に相互作用
が生じ、結果的に顔料粒子の表面に樹脂吸着層が形成さ
れるためと推定できる。(Function) Although the mechanism of action of the pigment dispersant of the present invention is not clear, it is the pigment dispersant adsorbed on the surface of pigment particles that has a remarkable effect on non-aggregation, fluidity, etc. in a non-aqueous vehicle. It is presumed that this is because an interaction occurs between the pigment particles and the resin component contained in the non-aqueous vehicle, resulting in the formation of a resin adsorption layer on the surface of the pigment particles.
以下に本発明の顔料分散剤の合成法の概略を製造例とし
て述べる。例中「部」、「％」とは「重量部」、「重量
％」をそれぞれ示す。The outline of the method for synthesizing the pigment dispersant of the present invention will be described below as a production example. In the examples, "parts" and "%" refer to "parts by weight" and "% by weight," respectively.
〔製造例１〕 クロルスルホン酸５００部に、キナクリドン（Ｃ。[Manufacture example 1] Quinacridone (C.
１、Ｐｉｇｍｅｎｔ Ｖｉｏｌｅｔ １９ ） ６２
部を２０〜３０℃で熔解して７０℃で２時間攪拌する。1, Pigment Violet 19) 62
The mixture was melted at 20-30°C and stirred at 70°C for 2 hours.
反応液を５０００部の氷水に注入してろ過、水洗したペ
ーストをメタノール１０００部に溶解したロジンアミン
（商品名二ロジンアミンＤ、バーキュレス社製）８６部
に加えて６０℃で３時間攪拌する。The reaction solution was poured into 5,000 parts of ice water, filtered, and washed with water. The paste was added to 86 parts of rosin amine (trade name: Dirosin amine D, manufactured by Vercules) dissolved in 1,000 parts of methanol, and stirred at 60° C. for 3 hours.
次に１％の酢酸水溶液２０００部を加えて、ろ過。Next, 2000 parts of 1% acetic acid aqueous solution was added and filtered.
水洗、乾燥して顔料分散剤（ａ）１２５部を得た。It was washed with water and dried to obtain 125 parts of pigment dispersant (a).
〔製造例２〕
９８％硫酸５００部にキナクリドン（Ｃ０１，Ｐｉｇｍ
ｅｎｔ Ｖｉｏｌｅｔ １９ ） ６２部、パラホルム
アルデヒド１７部およびα−クロルアセトアミド５６部
を１０〜２０°ＣＴ：溶解して３０℃で２時間攪拌する
。反応液を４０００部の氷水に注入してろ過、水洗後メ
タノール１０００部とキシレン１０００部を使用して洗
浄したペーストをキシレン５００部に溶解した水添ロジ
ン（商品名：ステベライトレジン、バーキュレス社製）
６７部に加え炭酸ナトリウム１０部を加えて１３０℃で
５時間攪拌する。反応液を冷却しメタノール１５００部
を加えてろ過し、メタノールｌｏ。[Production Example 2] Quinacridone (C01, Pigm
62 parts of ent Violet 19), 17 parts of paraformaldehyde and 56 parts of α-chloroacetamide were dissolved at 10-20°C and stirred at 30°C for 2 hours. The reaction solution was poured into 4,000 parts of ice water, filtered, washed with water, and washed with 1,000 parts of methanol and 1,000 parts of xylene.The paste was dissolved in 500 parts of xylene to make hydrogenated rosin (trade name: Stevelite Resin, manufactured by Vercules). )
In addition to 67 parts, 10 parts of sodium carbonate was added, and the mixture was stirred at 130°C for 5 hours. The reaction solution was cooled, 1500 parts of methanol was added and filtered, and methanol was added.
０部、水３０００部で洗浄後乾燥して顔料分散剤（ｂ）
１２３部を得た。Pigment dispersant (b) after washing with 0 parts and 3000 parts of water and drying.
123 copies were obtained.
〔製造例３〕
クロルスルホン酸８３０部に、９８％硫酸２５０部、パ
ラホルムアルデヒド１８６部およびキナクリドン（Ｃ，
１，Ｐｉｇｍｅｎｔ Ｖｉｏｌｅｔ １９ ） ６２部
を加えて８０℃に加熱する。食塩１９２部を１２時間を
要して除々に加えて冷却する。反応液を５ｏｏｏ部の氷
水に注入してろ過、水洗後メタノール１０００部とキ９
１２１０００部を使用して洗浄し、クロルメチル化キナ
クリドンのキシレンペーストを得る。このペーストをキ
シレン５００部に溶解したロジン（商品名：白菊ロジン
、２川化学工業製）６６部に加え製造例２と同一の方法
で処理し、顔料分散剤（ｃ）１１３部を得た。[Production Example 3] 830 parts of chlorosulfonic acid, 250 parts of 98% sulfuric acid, 186 parts of paraformaldehyde and quinacridone (C,
1. Add 62 parts of Pigment Violet 19) and heat to 80°C. 192 parts of common salt was gradually added over 12 hours and cooled. The reaction solution was poured into 500 parts of ice water, filtered, washed with water, and mixed with 1000 parts of methanol.
A xylene paste of chloromethylated quinacridone is obtained by washing using 121,000 parts. This paste was added to 66 parts of rosin (trade name: Shiragiku Rosin, manufactured by Futagawa Chemical Industry Co., Ltd.) dissolved in 500 parts of xylene and treated in the same manner as in Production Example 2 to obtain 113 parts of pigment dispersant (c).
〔製造例４〕
トルエン２０００部にβ−オキシナフトエ酸ナトリウム
２１０部とロジンアミン（商品名：ロジンアミンＤ、バ
ーキュレス社製）２８５部を溶解し、三塩化リン６９部
を加えて８０℃で５時間攪拌する。[Production Example 4] 210 parts of sodium β-oxynaphthoate and 285 parts of rosin amine (trade name: Rosin amine D, manufactured by Vercules) were dissolved in 2000 parts of toluene, 69 parts of phosphorus trichloride was added, and the mixture was stirred at 80°C for 5 hours. do.
水２０００部を加えて水酸化ナトリウムにより弱アルカ
リ性として水蒸気蒸留を行い、トルエンを除去する。次
いでろ過、水洗、乾燥して得たロジン誘導体をエタノー
ル２０００部に熔解し、６Ｂ酸１７８部を常法によりジ
アゾ化したジアゾニウム液１０００部に加えてカップリ
ングし水酸化ナトリウムを加えてＰ Ｈ８〜１０に調整
する。塩化カルシウム５３部を加えてろ過、水洗、乾燥
して顔料分散剤（ｄ）６０６部を得た。Add 2,000 parts of water, make the mixture weakly alkaline with sodium hydroxide, and perform steam distillation to remove toluene. Next, the rosin derivative obtained by filtration, water washing, and drying was dissolved in 2000 parts of ethanol, and 178 parts of 6B acid was added to 1000 parts of diazonium solution diazotized by a conventional method for coupling, and sodium hydroxide was added to give a pH of 8~. Adjust to 10. 53 parts of calcium chloride was added, filtered, washed with water, and dried to obtain 606 parts of pigment dispersant (d).
〔製造例５〕
ジオキサン５００部に４−デヒドロアビエチルアミンス
ルホニル−アセトアセトアニリド４６部を熔解し、４，
４−ジクロルベンジジン１３部を常法によりジアゾ化し
たジアゾニウム液１００部に加えてカップリングする。[Production Example 5] 46 parts of 4-dehydroabiethylaminesulfonyl-acetoacetanilide was dissolved in 500 parts of dioxane, and 4,
13 parts of 4-dichlorobenzidine are added to 100 parts of a diazonium solution diazotized by a conventional method for coupling.
水２０００部を加えてろ過、水洗、乾燥して顔料分散剤
（ｅ）５８部を得た。2000 parts of water was added, filtered, washed with water, and dried to obtain 58 parts of pigment dispersant (e).
〔製造例６〕
製造例１のキナクリドン６２部の代りにジオキサジンバ
イオレット （Ｃ，Ｉ、Ｐｉｇｍｅｎｔ Ｖｉｏｌｅｔ
２３ ） ５９部を使用してクロルスルホン化の反
応温度を４０℃に、ロジンアミンの使用量を８６部に変
更して同様の反応を行い顔料分散剤（ｆ）１２２部を得
た。[Production Example 6] Dioxazine violet (C, I, Pigment Violet) was used instead of 62 parts of quinacridone in Production Example 1.
23) Using 59 parts, the reaction temperature for chlorosulfonation was changed to 40°C, and the amount of rosin amine used was changed to 86 parts, and the same reaction was carried out to obtain 122 parts of pigment dispersant (f).
〔製造例７〕
製造例１のキナクリドン６２部の代りにペリノン（Ｃ，
Ｔ、Ｐｉｇｍｅｎｔ Ｏｒａｎｇｅ ４３ ） ６２部
を使用してロジンアミンの使用量を６６部に変更し同様
の反応を行うと顔料分散剤（ｇ）１００部が得られた。[Production Example 7] Perinone (C,
When the same reaction was carried out using 62 parts of Pigment Orange 43) and changing the amount of rosin amine used to 66 parts, 100 parts of pigment dispersant (g) was obtained.
〔製造例８〕
製造例２のキナクリドン６２部の代りにフラバンスロン
（Ｃ，Ｔ、Ｐｉｇｍｅｎｔ Ｙｅｌｌｏｗ ２４ ）
８２部、水添ロジン６７部の代りに重合ロジン（商品名
：ボリペ−ルレジン、バーキュレス社製）６６部を使用
して同様の反応を行うと顔料分散剤（ｈ）１３２部が得
られた。[Production Example 8] Flavanthrone (C, T, Pigment Yellow 24) instead of 62 parts of quinacridone in Production Example 2
When the same reaction was carried out using 66 parts of polymerized rosin (trade name: Volipale Resin, manufactured by Vercules) instead of 82 parts and 67 parts of hydrogenated rosin, 132 parts of pigment dispersant (h) were obtained.
〔製造例９〕
製造例２のキナクリドン６２部の代りにペリレン（Ｃ，
Ｔ、Ｐｉｇｍｅｎｔ Ｒｅｄ １７８ ） ７５部、水
添ロジン６７部の代りに不均化ロジン（商品名：ロンデ
スＲ２荒川化学製）６６部を使用して同様の反応を行う
と顔料分散剤（ｉ）１３４部が得られた。[Production Example 9] Perylene (C,
Pigment Red 178) and 66 parts of disproportionated rosin (trade name: LONDES R2 manufactured by Arakawa Chemical Co., Ltd.) instead of 75 parts of hydrogenated rosin and 66 parts of Pigment Red 178) were used to carry out the same reaction, resulting in pigment dispersant (i) 134 part was obtained.
〔製造例１０〕
製造例２のキナクリドン６２部の代りにアントラピリミ
ジン（Ｃ，１，Ｐｉｇｍｅｎｔ Ｙｅｌｌｏｔｎ １０
８） ４８部、水添ロジンの代りにマレイン化ロジン（
商品名；マルキードＮｏ ３０Ａ、２川化学製）２５
部を使用して同様の反応を行うと顔料分散剤（ｊ）６８
部が得られた〔製造例１１〕
製造例２のキナクリドン６２部の代りにアンサンスロン
（Ｃ，１，Ｐｉｇｍｅｎｔ Ｒｅｄ １６８ ） ４６
部、水添ロジンの代りに酸化ロジン（商品名：セレミク
、荒用化学製）３１部を使用して同様の反応を行うと顔
料骨散剤（ｋ）６９部が得られた。[Production Example 10] Instead of 62 parts of quinacridone in Production Example 2, anthrapyrimidine (C, 1, Pigment Yellow 10
8) 48 parts, maleated rosin (instead of hydrogenated rosin)
Product name: Marquido No 30A, manufactured by Futagawa Chemical Co., Ltd.) 25
Pigment dispersant (j) 68
[Production Example 11] Anthanthrone (C, 1, Pigment Red 168) 46 parts was obtained in place of 62 parts of quinacridone in Production Example 2.
When the same reaction was carried out using 31 parts of oxidized rosin (trade name: Selemik, manufactured by Arayo Kagaku) in place of the hydrogenated rosin, 69 parts of pigment agglomerate (k) were obtained.
〔製造例１２〕
製造例２のキナクリドン６２部の代りにインダンスロン
（Ｃ，１，Ｐｉｇｍｅｎｔ Ｂｌｕｅ ６０ ） ４４
部、水添ロジンの代りにロジン変性フェノール樹脂（商
品名：ペンタリン８０２＾、パーキュレス社ｉ！り５０
部を使用して同様の反応を行うと顔料分散剤（１）７０
部が得られた。[Production Example 12] Indanthrone (C, 1, Pigment Blue 60) 44 instead of 62 parts of quinacridone in Production Example 2
In place of hydrogenated rosin, use rosin-modified phenolic resin (product name: Pentaline 802^, Percules i!ri 50).
Pigment dispersant (1) when the same reaction is carried out using 70 parts
part was obtained.
〔製造例１３〕
製造例２のキナクリドン６２部の代りにビランスロン（
Ｃ，１，Ｐｉｇｍｅｎｔ Ｒｅｄ ２１６ ） ６４部
を使用して同様の反応を行うと顔料分散剤（ｍ）９１部
が得られた。[Production Example 13] Instead of 62 parts of quinacridone in Production Example 2, vilanthrone (
When the same reaction was carried out using 64 parts of C,1, Pigment Red 216), 91 parts of pigment dispersant (m) were obtained.
〔製造例１４〕
製造例１のキナクリドン６２部の代りにチオインジゴ（
Ｃ，１，Ｖａｔ Ｒｅｄ ４１） ４１部を使用して、
ロジンアミンの使用量を４３部に変更し同様の反応を行
うと顔料分散剤（ｎ）６１部が得られた。[Production Example 14] Thioindigo (
C, 1, Vat Red 41) Using 41 copies,
When the same reaction was carried out with the amount of rosin amine used changed to 43 parts, 61 parts of pigment dispersant (n) were obtained.
〔製造例１５〕
製造例１のキナクリドン６２部の代りに１．２−ジヒド
ロキシアントラキノン４８部を使用して同様＝１４−
の反応を行うと顔料分散剤（０）１１２部が得られた。[Production Example 15] When 48 parts of 1,2-dihydroxyanthraquinone was used in place of 62 parts of quinacridone in Production Example 1, the same reaction as 14- was carried out to obtain 112 parts of pigment dispersant (0).
以下に実施例、比較例を挙げて説明する。例中「部」、
「％」とは「重量部」、「重量％」をそれぞれ示す。Examples and comparative examples will be described below. In the example, "part",
"%" refers to "parts by weight" and "% by weight", respectively.
なお、アルファベントで示す各化合物は製造例に表示し
たものと対応する。In addition, each compound shown by alphabento corresponds to that shown in the production example.
実施例１
０ジン変性フエノール樹脂系オフセソトインキフエスに
顔斜方が２０％となるようにＣ０Ｉ、Ｐｉｇｍｅｎｔ
Ｒｅｄ５７：１単独（比較例）を分散した後、顔料分散
剤（ｄ）をＣ，１，Ｐｉｇｍｅｎｔ Ｒｅｄ ５１：
１に対して１０／９０になるように添加してオフセット
インキを調製し、その流動性をスプレッドメーターによ
り測定した。結果は表１のとおりで５本発明によるもの
が比較例よりも優れている。Example 1 C0I and Pigment were added to the O-Zin-modified phenolic resin offset ink FES so that the facial oblique area was 20%.
After dispersing Red 57:1 alone (comparative example), the pigment dispersant (d) was added to C,1, Pigment Red 51:
An offset ink was prepared by adding 1 to 10/90, and its fluidity was measured using a spread meter. The results are shown in Table 1, and 5 samples according to the present invention are superior to the comparative example.
また該オフセットインキで印刷した印刷物の色調の鮮明
性３着色力および光沢に関する効果においても（憂れて
いた。Furthermore, the effects regarding color clarity, color strength, and gloss of printed matter printed with the offset ink were also poor.
また顔料分散剤（ｄ）を予めＣ，１，Ｐｉｇｍｅｎｔ
Ｒｅｄ ５７：１に対して１０％となるように添加した
顔料組成物をその含有量が２０％となるように分散して
調製したオフセントインキも同等の効果が得られた。In addition, the pigment dispersant (d) is preliminarily mixed with C, 1, Pigment.
Similar effects were obtained with an off-cent ink prepared by dispersing a pigment composition added to Red 57:1 in an amount of 10% to a content of 20%.
実施例２〜１５
０ジン変性フエノール樹脂系オフセントインキフエスに
顔斜方が２０％（無機顔料のときは６０％）となるよう
に各種顔料単独（比較例）を分散あるいは各種顔料を分
散させた後、製造例１〜９で示した各種顔料分散剤を添
加してオフセットインキを調製し、その流動性を調べた
結果は表１のとおりで２本発明によるものが流動性に優
れている。Examples 2 to 15 Dispersing various pigments alone (comparative examples) or dispersing various pigments in zero-gin modified phenolic resin offset ink so that the face obliqueness is 20% (60% in the case of inorganic pigments) After that, various pigment dispersants shown in Production Examples 1 to 9 were added to prepare offset inks, and the fluidity of the inks was examined. The results are shown in Table 1. 2. The ink according to the present invention has excellent fluidity. There is.
また、該オフセットインキで印刷した印刷物の色調の鮮
明性９着色力および光沢に関する効果においても優れた
結果が得られた。In addition, excellent results were obtained in terms of color clarity, coloring strength, and gloss of printed matter printed with the offset ink.
（以下余白）
表 １
オフセットインキの流動性（スプレッドメータ）実施例
１６
グラビア用ライムロジンワニスにＣ，１，Ｐｉｇｍｅｎ
ｔ Ｒｅｄ ４９を顔斜方が１０％になるように配合し
、サンドミルにより分散を行い、顔料分散液を得た（比
較例）。(Margin below) Table 1 Fluidity of offset ink (spread meter) Example 16 C, 1, Pigmen in lime rosin varnish for gravure
t Red 49 was blended so that the face obliqueness was 10%, and dispersion was performed using a sand mill to obtain a pigment dispersion (comparative example).
得られた顔料分散液に顔料分散剤（ｄ）をＣ，１，Ｐｉ
ｇｍｅｎｔ Ｒｅｄ ４９に対して１０％になるように
配合し。Pigment dispersant (d) was added to the obtained pigment dispersion by C,1,Pi
gment Red 49 at a concentration of 10%.
ディシルバーで均一に攪拌してグラビアインキを調製し
、その粘度をＢＭ型粘度計により測定した。A gravure ink was prepared by stirring uniformly with a disc silver, and its viscosity was measured with a BM type viscometer.
結果は表２のとうりで本発明によるものが比較例よりも
優れている。The results are shown in Table 2, and the one according to the present invention is superior to the comparative example.
また、該グラビアインキで印刷した印刷物の色調の鮮明
性９着色力および光沢に関する効果においても優れてい
た。Furthermore, the printed matter printed with the gravure ink was excellent in terms of color clarity, coloring strength, and gloss.
また顔料分散剤（ｄ）を予めグラビア用ライムロジンワ
ニスにサンドミルで分散して得た分散液をＣ８１、Ｐｉ
ｇｍｅｎｔ Ｒｅｄ ４９と顔料分散剤（（１）との重
量比が９：１になるように添加しても同等の効果が得ら
れた。In addition, a dispersion obtained by dispersing the pigment dispersant (d) in lime rosin varnish for gravure using a sand mill was used as C81, Pi.
The same effect was obtained even when the weight ratio of gment Red 49 and pigment dispersant ((1) was 9:1.
実施例１７〜２９
グラビア用ライムロジンワニスに顔斜方が１０％（無機
顔料のときは２５％）となるように各種顔料単独（比較
例）を分散あるいは各種顔料を分散させたのち製造例１
〜９で示した各種顔料分散剤を添加してグラビアインキ
を調製し、その粘度を調べた結果は表２のとおりで本発
明によるものが流動性に優れている。Examples 17-29 After dispersing various pigments alone (comparative example) or dispersing various pigments in lime rosin varnish for gravure so that the face obliqueness is 10% (25% in the case of inorganic pigments), Production Example 1
Gravure inks were prepared by adding the various pigment dispersants shown in 9 to 9, and the viscosity thereof was examined. The results are shown in Table 2, and the ink according to the present invention has excellent fluidity.
また、該グラビアインキで印刷した印刷物の色調の鮮明
性１着色力および光沢に関する効果においても優れた結
果が得られた。Furthermore, excellent results were obtained in terms of color clarity, coloring power, and gloss of printed matter printed with the gravure ink.
（以下余白）
＝１０−
表 ２
グラビアインキの粘度 （ＢＭ型粘度計）実施例３０
焼付は塗料用アルキッド樹脂ワニスにＣ０１，Ｉ’ｉｇ
ｍｅｎｔ Ｖｉｏｌｅｔ １９を顔料骨が６％になるよ
うに配合し。(Margins below) = 10 - Table 2 Viscosity of gravure ink (BM type viscometer) Example 30 Baking was performed on alkyd resin varnish for paints with C01, I'ig
ment Violet 19 is blended so that the pigment bone content is 6%.
ボールミルで分散を行い、顔料分散液を得た（比較例）
。また顔料分散剤（ａ）をキシレン中にアトライターに
より分散し、顔料分散剤（ａ）の濃厚キシレン分散液を
調製した。Dispersion was performed using a ball mill to obtain a pigment dispersion (comparative example)
. Further, the pigment dispersant (a) was dispersed in xylene using an attritor to prepare a concentrated xylene dispersion of the pigment dispersant (a).
次に上記顔料分散液と顔料分散剤（ａ）のキシレン分散
液をＣ，１，Ｐｉｇｍｅｎｔ Ｖｉｏｌｅｔ １９と顔
料分散剤（ａ）の重量比が９：１になるようにディシル
バーにて均一に混合して塗料を調製し、その粘度をＢＭ
型粘度計により測定した。結果は表３のとうりで１本発
明によるものが比較例よりも優れている。Next, the above pigment dispersion and the xylene dispersion of pigment dispersant (a) were uniformly mixed in a dissilver so that the weight ratio of C,1, Pigment Violet 19 and pigment dispersant (a) was 9:1. Prepare the paint and adjust its viscosity to BM
Measured using a type viscometer. The results are shown in Table 3, and the one according to the present invention is superior to the comparative example.
また、該塗料で塗装した塗装物の色調の鮮明性。Also, the clarity of the color tone of the painted object painted with the paint.
着色力および光沢に関する効果においても優れていた。It was also excellent in terms of tinting strength and gloss.
また上記顔料分散液に顔料分散剤（ａ）の粉末を顔料に
対して１０％となるように添加してディシルバーで均一
混合しても同等の効果が得られた。The same effect was also obtained by adding powder of pigment dispersant (a) to the pigment dispersion liquid in an amount of 10% based on the amount of pigment and uniformly mixing the mixture with a disilver.
実施例３１〜４５
焼付は塗料用アルキッド樹脂ワニスに顔料骨が６−２１
＝
％となるように各種顔料単独（比較例）を分散あるいは
各種顔料を分散したのち製造例１〜９で示した各化合物
を添加して塗料を調製し、その粘度を測定した。結果は
表３のとおりで本発明によるものが比較例よりも優れて
いる。Examples 31-45 Baking was performed using alkyd resin varnish for paint with pigment bones 6-21
After dispersing various pigments alone (comparative examples) or dispersing various pigments so that the amount of paint was %, each compound shown in Production Examples 1 to 9 was added to prepare a paint, and its viscosity was measured. The results are shown in Table 3, and the one according to the present invention is superior to the comparative example.
また、該塗料で塗装した塗装物の色調の鮮明性。Also, the clarity of the color tone of the painted object painted with the paint.
着色力および光沢に関する効果においても優れていた。It was also excellent in terms of tinting strength and gloss.
また分散安定性については用途上、とくに問題となる色
分かれ安定性について実施例をもって説明する。Regarding dispersion stability, color separation stability, which is a particular problem in terms of use, will be explained using examples.
表３の実施例に示される塗料をアルキッド樹脂ワニスで
予め調製した酸化チタンのベース塗料で顔料と酸化チタ
ンの比率が１；１０になるようにカットし淡色塗料を得
る。The paints shown in the examples in Table 3 are cut with a titanium oxide base paint prepared in advance using an alkyd resin varnish so that the ratio of pigment to titanium oxide is 1:10 to obtain a light-colored paint.
淡色塗料をさらにキシレンで希釈しフォードカップＮ０
０４で２０秒（２５℃）にｍ製し、試験管に注入してガ
ラス壁面の変化を観察した結果を表４に示す。いずれも
本発明によるものが優れた結果を示す。Ford Cup N0 by further diluting the light colored paint with xylene
04 for 20 seconds (25° C.), injected into a test tube, and observed for changes in the glass wall surface. Table 4 shows the results. In both cases, the method according to the present invention shows excellent results.
（以下余白）
＝２２−
表３
アルキッド焼付は塗料の粘度（ＢＭ型粘度計）判定
◎ 全く均一
〇 僅かに白いスジが認められる
△ 白い縞模様状態
× 白が完全に分離
〔発明の効果〕
本発明により２次にあげる効果が確認された。(Left below) =22- Table 3 Alkyd baking is determined by paint viscosity (BM type viscometer)
◎ Completely uniform 〇 Slight white streaks observed △ White striped pattern × White completely separated [Effects of the Invention] The second effect of the present invention was confirmed.
（１）オフセットインキ、グラビアインキおよび塗料な
どの非水系顔料分散液において本発明の顔料分散剤を添
加すると非集合性、流動性などの使用通性が著しく向上
する。(1) When the pigment dispersant of the present invention is added to nonaqueous pigment dispersions such as offset inks, gravure inks, and paints, usability such as non-aggregation properties and fluidity is significantly improved.
（２）該分散液による印刷物または塗装物は顔料分散剤
を添加しない場合に比較して色調の鮮明性９着色力およ
び光沢が優れている。(2) Printed matter or painted matter produced using the dispersion has superior color clarity, tinting strength, and gloss compared to those produced without the addition of a pigment dispersant.
Claims (1)
を有する有機色素または有機色素誘導体と、カルボキシ
ル基またはアミノ基を有するロジンまたはロジン誘導体
とを反応させてなることを特徴とする顔料分散剤。 ２、有機色素がアントラキノン系、アゾ系、キナクリド
ン系、ジオキサジン系、アントラピリジン系、アンサン
スロン系、インダンスロン系、フラバンスロン系、ピラ
ンスロン系、ペリノン系、ペリレン系およびチオインジ
ゴ系から選ばれる色素である特許請求の範囲第１項記載
の顔料分散剤。 ３、ロジンまたはロジン誘導体がロジン、ロジンアミン
、マレイン化ロジン、不均化ロジン、重合ロジン、水添
ロジン、酸化ロジンおよびロジン変性フェノール樹脂か
ら選ばれる１種である特許請求の範囲第１項または第２
項記載の顔料分散剤。[Claims] 1. It is characterized by reacting an organic dye or an organic dye derivative having a functional group capable of reacting with a carboxyl group or an amino group with a rosin or a rosin derivative having a carboxyl group or an amino group. Pigment dispersant. 2. The organic dye is a dye selected from anthraquinone series, azo series, quinacridone series, dioxazine series, anthrapyridine series, anthanthrone series, indanthrone series, flavanthrone series, pyranthrone series, perinone series, perylene series and thioindigo series. A pigment dispersant according to claim 1. 3. Claim 1 or 3, wherein the rosin or rosin derivative is one selected from rosin, rosin amine, maleated rosin, disproportionated rosin, polymerized rosin, hydrogenated rosin, oxidized rosin, and rosin-modified phenolic resin. 2
Pigment dispersant as described in section.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61035267A JPH0657805B2 (en) | 1986-02-21 | 1986-02-21 | Pigment dispersant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61035267A JPH0657805B2 (en) | 1986-02-21 | 1986-02-21 | Pigment dispersant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62195053A true JPS62195053A (en) | 1987-08-27 |
| JPH0657805B2 JPH0657805B2 (en) | 1994-08-03 |
Family
ID=12437023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61035267A Expired - Lifetime JPH0657805B2 (en) | 1986-02-21 | 1986-02-21 | Pigment dispersant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0657805B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01259998A (en) * | 1988-04-12 | 1989-10-17 | Daito Kako Kk | Solid correcting agent |
| WO2016136134A1 (en) * | 2015-02-24 | 2016-09-01 | セイコーエプソン株式会社 | Inkjet ink composition, inkjet recording method and ink set |
| WO2016136133A1 (en) * | 2015-02-24 | 2016-09-01 | セイコーエプソン株式会社 | Ink jet ink composition and ink jet recording method |
-
1986
- 1986-02-21 JP JP61035267A patent/JPH0657805B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01259998A (en) * | 1988-04-12 | 1989-10-17 | Daito Kako Kk | Solid correcting agent |
| WO2016136134A1 (en) * | 2015-02-24 | 2016-09-01 | セイコーエプソン株式会社 | Inkjet ink composition, inkjet recording method and ink set |
| WO2016136133A1 (en) * | 2015-02-24 | 2016-09-01 | セイコーエプソン株式会社 | Ink jet ink composition and ink jet recording method |
| JP2016155909A (en) * | 2015-02-24 | 2016-09-01 | セイコーエプソン株式会社 | Inkjet ink composition and inkjet recording method |
| JP2016155910A (en) * | 2015-02-24 | 2016-09-01 | セイコーエプソン株式会社 | Inkjet ink composition, inkjet recording method, and ink set |
| US11718100B2 (en) | 2015-02-24 | 2023-08-08 | Seiko Epson Corporation | Ink jet ink composition, ink jet recording method, and ink set |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0657805B2 (en) | 1994-08-03 |
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