JPH037768A - Organometallic complex salt compound - Google Patents
Organometallic complex salt compoundInfo
- Publication number
- JPH037768A JPH037768A JP14212089A JP14212089A JPH037768A JP H037768 A JPH037768 A JP H037768A JP 14212089 A JP14212089 A JP 14212089A JP 14212089 A JP14212089 A JP 14212089A JP H037768 A JPH037768 A JP H037768A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- parts
- water
- compound
- group
- 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
- -1 salt compound Chemical class 0.000 title claims abstract description 24
- 125000002524 organometallic group Chemical group 0.000 title description 6
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 5
- 229910052742 iron Inorganic materials 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 3
- 239000011734 sodium Substances 0.000 claims abstract description 3
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims abstract description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 7
- 239000011651 chromium Substances 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000011591 potassium Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- GSOLWAFGMNOBSY-UHFFFAOYSA-N cobalt Chemical group [Co][Co][Co][Co][Co][Co][Co][Co] GSOLWAFGMNOBSY-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
- 239000000203 mixture Substances 0.000 abstract description 14
- 239000003795 chemical substances by application Substances 0.000 abstract description 12
- 239000003960 organic solvent Substances 0.000 abstract description 6
- 235000017281 sodium acetate Nutrition 0.000 abstract description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract description 5
- 238000005859 coupling reaction Methods 0.000 abstract description 5
- 239000001632 sodium acetate Substances 0.000 abstract description 5
- 230000008878 coupling Effects 0.000 abstract description 3
- 238000010168 coupling process Methods 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- LPUBRQWGZPPVBS-UHFFFAOYSA-N 3-butoxypropan-1-amine Chemical compound CCCCOCCCN LPUBRQWGZPPVBS-UHFFFAOYSA-N 0.000 description 2
- ASGAOGZVKDPMHV-UHFFFAOYSA-N 3-ethylhexan-1-amine Chemical compound CCCC(CC)CCN ASGAOGZVKDPMHV-UHFFFAOYSA-N 0.000 description 2
- BOTGCZBEERTTDQ-UHFFFAOYSA-N 4-Methoxy-1-naphthol Chemical compound C1=CC=C2C(OC)=CC=C(O)C2=C1 BOTGCZBEERTTDQ-UHFFFAOYSA-N 0.000 description 2
- XYHQAQRXVQZBQV-UHFFFAOYSA-N 4-ethoxynaphthalen-1-ol Chemical compound C1=CC=C2C(OCC)=CC=C(O)C2=C1 XYHQAQRXVQZBQV-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 1
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 1
- XGRZWVWRMKAQNU-UHFFFAOYSA-K 2-carboxyphenolate;chromium(3+) Chemical compound [Cr+3].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O XGRZWVWRMKAQNU-UHFFFAOYSA-K 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- VHYUNSUGCNKWSO-UHFFFAOYSA-N 3-propan-2-yloxypropan-1-amine Chemical compound CC(C)OCCCN VHYUNSUGCNKWSO-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- SUCPNTQKGBIXHL-UHFFFAOYSA-N 4-phenylmethoxynaphthalen-1-ol Chemical compound C12=CC=CC=C2C(O)=CC=C1OCC1=CC=CC=C1 SUCPNTQKGBIXHL-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical group [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- LCPUDZUWZDSKMX-UHFFFAOYSA-K azane;hydrogen sulfate;iron(3+);sulfate;dodecahydrate Chemical compound [NH4+].O.O.O.O.O.O.O.O.O.O.O.O.[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O LCPUDZUWZDSKMX-UHFFFAOYSA-K 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 229910000335 cobalt(II) sulfate Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000012943 hotmelt Substances 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
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100000150 mutagenicity / genotoxicity testing Toxicity 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Landscapes
- Developing Agents For Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、特に電子写真、静電記録等の静電潜像を現象
するのに使用されるトナー用の荷電調整剤として有用な
有機金属錯塩に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to an organometallic complex useful as a charge control agent for toners used in particular to develop electrostatic latent images in electrophotography, electrostatic recording, etc. .
従来の技術
静電潜像現象用トナーにおいては、結着用樹脂のみでは
、摩擦帯電性を制御することが困難であり、その改良を
目的として染料、顔料等を添加することが、広（行われ
ている。今日、この分野で実用化されている染料、顔料
類は、トナーに正荷電を付与するニグロシン系染料及び
負荷電を付与する有機金属錯体染料等である。Conventional technology In toners for electrostatic latent image phenomenon, it is difficult to control triboelectricity with only a binder resin, and it is widely used to add dyes, pigments, etc. for the purpose of improving this. Dyes and pigments that have been put to practical use in this field today include nigrosine dyes that impart a positive charge to the toner and organometallic complex dyes that impart a negative charge.
発明が解決しようとする課題
電子写真、静電記録媒体の多機能化、高速化が進んだの
に伴い、より優れた耐久安定性、環境安定性、解像力及
びコントラスト性を持ち、かぶりの小さいトナーを調製
する為の荷電調整剤の開発が求められている。即ち、本
発明の目的は、温度、湿度等の環境に影響されず、長期
の使用に耐え、画像の解像力と再現性に優れ、さらに高
濃度であり、かぶりのない画像を与えるトナーを調製す
る為の荷電調整剤を提供するにある。Problems to be Solved by the Invention As electrophotography and electrostatic recording media have become more multifunctional and faster, toners with better durability, environmental stability, resolution and contrast, and less fogging have been developed. There is a need for the development of charge control agents for the preparation of That is, an object of the present invention is to prepare a toner that is not affected by environments such as temperature and humidity, can withstand long-term use, has excellent image resolution and reproducibility, has high density, and provides images without fogging. To provide a charge control agent for
課題を解決するための手段
前記問題点を改良すべく鋭意研究を行った結果、本発明
に至った。即ち、本発明は式（１）〔式（１）中、Ｒ１
およびＲ２は、水素原子、ニトロ基、メチル基、クロル
原子、スルホン酸アミド基又はメチルスルホン基より選
ばれた原子又は基を、Ｒはメチル基、エチル基又はフェ
ニルメチル基を、Ｍはクロム、コバルト又は鉄原子をＸ
は水素、ナトリウム、カリウム、アンモニウム又は有機
アミン塩をそれぞれ表す〕
で表される有機金属錯塩化合物を提供する。Means for Solving the Problems As a result of extensive research aimed at improving the above-mentioned problems, the present invention has been achieved. That is, the present invention provides formula (1) [in formula (1), R1
and R2 is an atom or group selected from a hydrogen atom, a nitro group, a methyl group, a chloro atom, a sulfonic acid amide group, or a methylsulfone group; R is a methyl group, an ethyl group, or a phenylmethyl group; M is chromium; Cobalt or iron atom
represents hydrogen, sodium, potassium, ammonium, or an organic amine salt, respectively] An organometallic complex salt compound represented by the following is provided.
式（１）の化合物はこれを荷電調整剤として使用した場
合、前記問題点を完全に解決することができるものであ
り新規な構造の有機金属塩錯体化合物である。The compound of formula (1) can completely solve the above problems when used as a charge control agent, and is an organometallic salt complex compound with a novel structure.
分子中にスルホン基を含まず、クロム、コバルト又は鉄
を結合金属とする、２；１型金属錯体化合物は、例えば
特開昭５８−１８５６５３、特開昭６１−１０１５５８
、特開昭６３−２８１１７０等に示されているが、それ
らはいずれもカップラーとして、ベータナフトール又は
ペータナフ）−ル誘導体を使用したものである。一方ア
ルファナフトールをカップラーとした錯体化合物につい
てはその具体例を見出すことが出来ない。Type 2:1 metal complex compounds which do not contain a sulfone group in the molecule and have chromium, cobalt or iron as a binding metal are disclosed in, for example, JP-A-58-185653 and JP-A-61-101558.
, JP-A-63-281170, etc., all of which use beta-naphthol or petanaphthol derivatives as couplers. On the other hand, no specific example of a complex compound using alpha-naphthol as a coupler can be found.
これは、例えばＤｙｅｓ ａｎｄ Ｐｉｇｍｅｎｔ ９
（１９８８）１５３−１６３頁「Ｄｉｅ １３ｅｅｉ
ｎｆｌｕｓｓｃｍｇ ｄｅｓ Ｏ／ＰＶｅｒｈＭＩｔｎ
ｉｓｓｅｓ ｂｅｉ Ａｚｏ ｋｕｐｐｌｕｎｇｅｎ
ｍｉｔ １−Ｎａｐｈｔｈｏｌ ｉｎＮｉｃｈｔｗＷｂ
ｒｉｇｅｎ Ｍｃｄｉｅｎ Ｊ に記載があるように
、水中でのカップリング反応においては主に１−ナフト
ールの４−位が優先し、２−位へのカップリング反応が
おこりにくいことによると考えられる。This is for example Dyes and Pigment 9
(1988) pp. 153-163 “Die 13eei
nflusscmg des O/PVerhMITn
isses bei Azo kupplungen
mit 1-Naphthol inNichtwWb
This is believed to be because, as described in rigen Mcdien J, the 4-position of 1-naphthol takes precedence in the coupling reaction in water, and the coupling reaction to the 2-position is difficult to occur.
式（１）においてＭがコバルトの場合、本発明の調
化合物は鮮明な青色〜緑色の色相を示し、２；１型コバ
ルト錯体で可視部の長波長帯に吸収を持つという特異性
のある化合物である。そのような化合物は耐光性が優れ
ておりポリアミド、ポリイミド等の染色用の色素として
も十分用途を持つものである。When M in formula (1) is cobalt, the compound of the present invention exhibits a clear blue to green hue, and is a 2: type 1 cobalt complex having absorption in the long wavelength band of the visible region. It is. Such compounds have excellent light resistance and can be used as dyes for dyeing polyamides, polyimides, etc.
本発明の金属錯体化合物（１）は次の式〔式（２）中、
Ｒ１，Ｒ２は前記の通りである。〕で表される化合物を
水中で常法によりジアゾ化し、得られたジアゾ化物と次
の式
〔式（３）中、Ｒは前記の通りである。〕で表されるカ
ップリング成分とを水中或は水とＤＭＦ 、アセトン等
の有機溶媒との混合液中でカップリングすることにより
次の式（３）〔式（３）中、Ｒ＋、Ｒ２およびＲは前記
の通りである。〕
で表されるモノアゾ化合物を合成し、次にこのモノアゾ
化合物を水中或は水と有機溶媒との混合液中で、金属付
与剤と必要に応じ酢酸ナトリウム、酢酸カリウム等の存
在下ｐＨ値３〜９で、温度６０〜１００℃で反応させる
ことにより得ることができる。The metal complex compound (1) of the present invention has the following formula [in formula (2),
R1 and R2 are as described above. ] The compound represented by the above is diazotized in water by a conventional method, and the resulting diazotized product is combined with the following formula [In formula (3), R is as described above. ] in water or a mixture of water and an organic solvent such as DMF or acetone to form the following formula (3) [In formula (3), R+, R2 and R is as described above. ] A monoazo compound represented by is synthesized, and then this monoazo compound is heated to pH 3 in water or a mixture of water and an organic solvent in the presence of a metallizing agent and, if necessary, sodium acetate, potassium acetate, etc. ~9 and can be obtained by reacting at a temperature of 60 to 100°C.
式（２）で表される化合物の具体例としては、５ニトロ
−２−アミンフェノール、４−ニトロ２−アミノフェノ
ール、４，６−ジニトロ−２アミンフエノール、４−ク
ロロ−２−アミンフェノール、４−メチル−６−ニトロ
−２−７６＝
ミノフェノール、４−メチル−２−アミンフェノール、
５−メチル−２−アミンフェノール、２−アミンフェノ
ール、４−スルファモイル−２−アミンフェノール、４
−メチルスルホニル２−アミンフェノール等を挙げるこ
とができる。Specific examples of the compound represented by formula (2) include 5-nitro-2-aminephenol, 4-nitro-2-aminophenol, 4,6-dinitro-2-aminephenol, 4-chloro-2-aminephenol, 4-methyl-6-nitro-2-76=minophenol, 4-methyl-2-aminephenol,
5-methyl-2-aminephenol, 2-aminephenol, 4-sulfamoyl-2-aminephenol, 4
-methylsulfonyl 2-amine phenol and the like.
また前記式（３）で表されるカップリング成分の具体例
としては、４−メトキシ−１−ナフトール、４−エトキ
シ−１−ナフトール、４−フェニルメトキシ−１−ナフ
トール等を挙げることができる。（尚、４−エトキシ−
１−ナフトールはり、Ｒ，Ｐ、に記載のある、ヒドロ−
α−ナフトキノンとエタノールとの反応により合成する
ことができる。）
式（Ｉ）の生成に使用する金属付与剤の例としては通常
良く知られている硫酸クロム（ｍ）、サリチル酸クロム
、塩化クロム（ｍ）、塩化コバルト（ｎ）、硫酸コバル
ト（ＩＩ）、ギ酸クロム（ＩＩＩ）、塩化鉄（ｍ）、鉄
ミョウバン等を挙げることができる。Specific examples of the coupling component represented by the formula (3) include 4-methoxy-1-naphthol, 4-ethoxy-1-naphthol, 4-phenylmethoxy-1-naphthol, and the like. (In addition, 4-ethoxy-
1-naphthol beam, hydro-
It can be synthesized by reaction of α-naphthoquinone and ethanol. ) Examples of metallizing agents used in the production of formula (I) include the well-known chromium (m) sulfate, chromium salicylate, chromium (m) chloride, cobalt (n) chloride, cobalt (II) sulfate, Examples include chromium (III) formate, iron (m) chloride, iron alum, and the like.
このようにして得られた式（Ｉ）の有機金属錯体の水或
は水と有機溶媒中の溶液或は分散液に、アンモニア、或
は有機アミンを反応させ、アンモニア或は有機アミン塩
とすることもできる。The thus obtained solution or dispersion of the organometallic complex of formula (I) in water or water and an organic solvent is reacted with ammonia or an organic amine to form an ammonia or organic amine salt. You can also do that.
ここでアミンとしては、例えばメチルアミン、エチルア
ミン、ジメチルアミン、エタノールアミン、ブチルアミ
ン、ヘキシルアミン、２−エチルヘキシルアミン、３−
ブトキシプロピルアミン、３−イソプロポキシプロビル
アミン等を挙げることができる。Examples of the amine include methylamine, ethylamine, dimethylamine, ethanolamine, butylamine, hexylamine, 2-ethylhexylamine, 3-ethylhexylamine, and 3-ethylhexylamine.
Examples include butoxypropylamine, 3-isopropoxypropylamine, and the like.
本発明式（１）で表される金属錯体化合物は、熱及び貯
蔵安定性が高く、帯電性に優れており、かさ比重が小さ
く表面積が大きいのでトナー用荷電調節剤として好適で
ある。The metal complex compound represented by formula (1) of the present invention has high thermal and storage stability, excellent chargeability, and has a small bulk specific gravity and a large surface area, so it is suitable as a charge control agent for toner.
また（１）の化合物は一般に変異原性試験において陰性
を示し、更に衝撃及び熱に対しても安定であり、分解し
たり燃焼することはない。（１）を含むトナーは、負極
性に帯電し、低湿下においても、鮮明で、かつ安定な画
像を与える。Furthermore, the compound (1) generally shows negative results in mutagenicity tests, is stable against impact and heat, and does not decompose or burn. A toner containing (1) is negatively charged and provides a clear and stable image even under low humidity.
本発明の式（１）の金属錯体を含むトナーを製造するに
あたっては、着色材として公知のカーボンブラック、フ
タロシアニンブルー、鉄黒等が使用でき、又結着樹脂と
しては、公知のアクリル酸エステル類、オレフィン類、
スチレン類等の単重合体が使用できる。これらの結着樹
脂は金属錯体１部に対し通常１０〜１００００部使用さ
れる。さらに二成分現象剤として用いる場合は、キャリ
ア粉、例えば公知の鉄粉、フェライト、ガラスピーズ等
と混合して使用できる。In producing the toner containing the metal complex of formula (1) of the present invention, known carbon black, phthalocyanine blue, iron black, etc. can be used as the colorant, and known acrylic esters can be used as the binder resin. , olefins,
Single polymers such as styrenes can be used. These binder resins are usually used in an amount of 10 to 10,000 parts per 1 part of the metal complex. Furthermore, when used as a two-component phenomenon agent, it can be mixed with carrier powder such as known iron powder, ferrite, glass beads, etc.
また本発明の金属錯体化合物は耐光性、耐熱性、耐水性
に優れ、かつ鮮明度が高いので、各種の樹脂の着色剤、
塗料としても使用することができる。In addition, the metal complex compound of the present invention has excellent light resistance, heat resistance, water resistance, and high clarity, so it can be used as a coloring agent for various resins.
It can also be used as a paint.
実施例
以下実施例にしたがって本発明を説明するが部とは重量
部を表す。EXAMPLES The present invention will be described below with reference to Examples, where parts are by weight.
実施例１゜
４．６−シニトロー２−アミンフェノール４゜０部を１
０部のアセトンに溶かし、３５％塩酸５部と亜硝酸ナト
リウム１．５部を含む氷中８０部９
中に注ぎ、３時間撹拌を行いジアゾ化を完結せしめ、黄
色結晶を含む反応液を得た。このジアゾニウム塩を含む
反応液に、４−メトキシ−１ナフトール３．５部をアセ
トン１５部に溶解した溶液を注入し、１０％炭酸ナトリ
ウム水溶液を注加し、ｐＨを９〜１０とし、０〜５℃で
５時間撹拌して、カップリングを完結させ、式（４）で
表される物見が濃紺色でアセトン中、緑青色を呈するモ
ノアゾ化合物７．２部を含む反応液を得た。Example 1 4.0 parts of 4.6-sinitro-2-aminephenol was added to 1
The mixture was dissolved in 0 parts of acetone, poured into 80 parts of ice containing 5 parts of 35% hydrochloric acid and 1.5 parts of sodium nitrite, and stirred for 3 hours to complete diazotization, yielding a reaction solution containing yellow crystals. Ta. A solution prepared by dissolving 3.5 parts of 4-methoxy-1-naphthol in 15 parts of acetone was poured into the reaction solution containing this diazonium salt, and a 10% aqueous sodium carbonate solution was added to adjust the pH to 9-10. The mixture was stirred at 5° C. for 5 hours to complete the coupling, and a reaction solution containing 7.2 parts of a monoazo compound represented by formula (4), which was dark blue in appearance and exhibited a green-blue color in acetone, was obtained.
次いでこの反応液に酢酸ナトリウム３水和物８．０部と
塩化コバルト６水和物２．８部とを加え８５〜９０℃に
昇温し、３時間反応させ７．８部の結晶を得た。この結
晶は外観が黒色であり、その構造は式（５）
で表される化合物７．６部をえた。Next, 8.0 parts of sodium acetate trihydrate and 2.8 parts of cobalt chloride hexahydrate were added to this reaction solution, the temperature was raised to 85-90°C, and the mixture was reacted for 3 hours to obtain 7.8 parts of crystals. Ta. This crystal had a black appearance and contained 7.6 parts of a compound whose structure was represented by formula (5).
更に同様にしてえた式（４）の化合物を含む反応液にＩ
）ＭＦ ５０部、硫酸クロム（ＩＩＤ ２．２部及び酢
酸ナトリウム１０部を加え昇温し、９０°Ｃで５時間反
応させ式（７）
で表され、アセトン溶液でλｍａｘ ６１０ ｎｍ
を示し減色は暗緑色であった。Furthermore, I was added to the reaction solution containing the compound of formula (4) obtained in the same manner
) 50 parts of MF, 2.2 parts of chromium sulfate (IID) and 10 parts of sodium acetate were added, heated, and reacted at 90°C for 5 hours.
The reduced color was dark green.
を加えｐＨを５〜７に調整しつつ温度８０℃で７時間撹
拌し式（６）
の化合物８．１部を得た。（７）のアセトン中のλｍａ
ｘは５２４ ｎｍと６７８ ｎｍであり、減色は暗線で
あった。The mixture was stirred at a temperature of 80° C. for 7 hours while adjusting the pH to 5 to 7 to obtain 8.1 parts of the compound of formula (6). (7) λma in acetone
x was 524 nm and 678 nm, and the color reduction was a dark line.
実施例２．
２−アミノ−５−二トロフェノール３．１ 部を水６０
部中に４８％苛性ソーダで加熱溶解し、氷を加え液温を
１０℃とし、亜硝酸ソーダ１．５部及び３５％塩酸８部
でジアゾ化を行った。４−メトキシーエ＝ナフトール３
．５部を４８％苛性ソーダで水５０部中に溶解した水溶
液を氷で１０℃とし、前記ジアゾニウム化合物を含む反
応液の中に注ぎ込んだ。温度１５℃以下に保ちつつ、１
０％苛性ソーダ水溶液でｐＨを１１．５〜１２に調整し
つつ一晩撹拌し、式（８）で表される外観が黒紺色の化
合物を含む反応液を得た。次にこの反応液に酢酸ナトリ
ウム６０部と塩化コバル） ＣＯＣｌ２・６Ｈ２０２，
８部を加え、ｐＨを６〜″７に保ちつつ温度を８００Ｇ
とし、この温度で１０時間撹拌した。生成物を濾過し、
乾燥粉砕すると暗青色粉体６．９部を得た。これは式（
９）
で表される金属錯塩であり、アセトン中で鮮明な青色を
呈しそのλｍａｘは６３５ ｎｍであった。Example 2. 3.1 parts of 2-amino-5-nitrophenol to 60 parts of water
The mixture was heated and dissolved in 48% caustic soda, ice was added to bring the temperature to 10°C, and diazotization was performed with 1.5 parts of sodium nitrite and 8 parts of 35% hydrochloric acid. 4-methoxye-naphthol 3
．． An aqueous solution of 5 parts of 48% caustic soda dissolved in 50 parts of water was heated to 10°C with ice and poured into the reaction solution containing the diazonium compound. While keeping the temperature below 15℃,
The mixture was stirred overnight while adjusting the pH to 11.5 to 12 with a 0% aqueous sodium hydroxide solution to obtain a reaction solution containing a compound represented by formula (8) with a dark blue appearance. Next, 60 parts of sodium acetate and cobal chloride (COCl2.6H202) were added to this reaction solution.
Add 8 parts and raise the temperature to 800G while maintaining the pH between 6 and 7.
The mixture was stirred at this temperature for 10 hours. filter the product;
Dry grinding yielded 6.9 parts of a dark blue powder. This is the formula (
9) It is a metal complex salt represented by the following, exhibits a clear blue color in acetone, and has a λmax of 635 nm.
同様にしてえた式（８）の化合物を含む反応液に酢酸ナ
トリウム７部、塩化クロムＣｒＣＩａ・６Ｈ２０３，２
部を加え昇温し９０〜９５℃で６時間反応させた。戸別
、乾燥、乾燥し黒色の粉体７，０部３
４
で表され、アセトンに青色に溶解しλｍａｘは６２５ｎ
ｍであった。To the reaction solution containing the compound of formula (8) obtained in the same manner, 7 parts of sodium acetate, chromium chloride CrCIa.6H203,2
The mixture was heated to 90 to 95°C for 6 hours. House-to-house, dried, dried black powder expressed as 7,0 parts 3 4, dissolved in acetone in blue color, λmax is 625n
It was m.
また同様にしてえた式（８）の化合物を含む反応液と水
中で塩化第二鉄とｐＨを６〜７に保ちつつ８０°Ｃで５
時間反応させると式（工１）
で表される化合物が得られ、その外観は黒青色でアセト
ンには赤色に溶解した。In addition, a reaction solution containing the compound of formula (8) obtained in the same manner and ferric chloride in water were heated at 80°C while keeping the pH at 6 to 7.
When reacted for a period of time, a compound represented by the formula (Step 1) was obtained, which had a black-blue appearance and dissolved red in acetone.
同様にして得た式（１２）の化合物を含む反応液に実施
例１で述べた方法で無機金属塩類を反応せしめ、次に示
す式（１３）、式（１４）及び式（１５）で表されるア
セトン中、褐色に溶解する錯塩化合物７．８部を得た。A similarly obtained reaction solution containing the compound of formula (12) was reacted with an inorganic metal salt by the method described in Example 1, and the results were expressed by the following formulas (13), (14), and (15). 7.8 parts of a complex salt compound dissolved in brown color in acetone was obtained.
実施例３゜
２−アミノ−４−メチルフェノール２．５部を通常の方
法でジアゾ化し、えられた反応液に４＝フェニルメトキ
シ−１−ナフトール５．０ 部のアセトン溶液を注加し
、苛性ソーダでｐＨを１１〜１２に維持し、−晩撹拌し
た。式（１２）混合液に溶解し、液温３０’Ｃに保ち、
この中に 瞥３−ブトキシプロピルアミン２．５部を加
え、生成物を反応液より晶出させ、式（１７）で表され
る化合物を得た。Example 3 2.5 parts of 2-amino-4-methylphenol was diazotized in a conventional manner, and an acetone solution of 5.0 parts of 4=phenylmethoxy-1-naphthol was added to the resulting reaction solution. The pH was maintained at 11-12 with caustic soda and stirred overnight. Dissolve in the mixture of formula (12) and keep the liquid temperature at 30'C,
2.5 parts of 3-butoxypropylamine was added to this, and the product was crystallized from the reaction solution to obtain a compound represented by formula (17).
の錯塩化合物を得た。そのアセトン中の減色はそれぞれ
紫色、褐色、赤青色であった。A complex salt compound of was obtained. The reduced colors in acetone were purple, brown, and reddish-blue, respectively.
実施例４゜
実施例２において式（９）の金属錯体の合成法と同様な
方法で生成した式（１６）
実施例１．２．３の方法に従って合成した金属錯体化合
物を以下に示す。Example 4 A metal complex compound of formula (16) produced in the same manner as the method for synthesizing the metal complex of formula (9) in Example 2 is shown below.
の化合物の１０部を水１８０部とＤＭＦ ２０部の１７
−
１８−
二３
応用例１゜
上記混合物を１７０℃で混練（ｈｏｔ ｍｅｌｔ ｋｎ
ｅａ−ｄｉｎｇ ） Ｌ、微粉砕し、分級により１５μ
ｍの粒径のものを採取した。10 parts of the compound in 180 parts of water and 20 parts of DMF
- 18- 23 Application example 1゜The above mixture was kneaded at 170°C (hot melt kn)
ea-ding) L, finely pulverized and classified to 15μ
A particle with a particle size of m was collected.
また別に下記構造
の金属錯体を荷電調整剤とする比較用のトナーを調製し
た。それぞれのトナー１部とキャリアとしての鉄粉９部
を混合し、両トナーの帯電量２４
をプローオフテスト（１３１ｏｗ−ｏｆｆ ｔｅｓｔ
）によって比較し次の結果を得た。Separately, a comparative toner was prepared using a metal complex having the following structure as a charge control agent. 1 part of each toner and 9 parts of iron powder as a carrier were mixed, and the charge amount of both toners was tested by a 131ow-off test.
) and obtained the following results.
帯電量μＣ／ｇ
式（７）を荷電調整剤とするトナー −２１，７５
式（４３） −１１゜００また
式（７）を荷電調整剤とするトナーについては複写によ
り、高品質の画像が得られ、繰返しテストによっても画
像は安定でありかぶりは認められなかった。Charge amount μC/g Toner using formula (7) as a charge control agent -21,75
Formula (43) -11°00 Furthermore, high-quality images were obtained by copying with the toner containing Formula (7) as a charge control agent, and the images were stable and no fogging was observed even after repeated tests.
式（７）の化合物は有機溶媒に溶は鮮明な青色を呈する
。ポリアミド、ポリエステル等の樹脂の着色剤として使
用すると、耐光性、耐水性に富む鮮明な青色に着色でき
た。The compound of formula (7) exhibits a clear blue color when dissolved in an organic solvent. When used as a coloring agent for resins such as polyamide and polyester, it could be colored a bright blue color with excellent light and water resistance.
応用例２゜
ポリエステル樹脂 ９４部
カーボンブランク ４部
式（１７）の化合物 ２部
応用例１と同様な方法により粒径１５μｍ以下のトナー
を得、帯電量の測定と連続複写テストを行った。また同
時に式（４４）
により、高い再現性と解像力に浸れたトナーを調製する
ことができる。Application Example 2 Polyester resin 94 parts Carbon blank 4 parts Compound of formula (17) 2 parts A toner having a particle size of 15 μm or less was obtained in the same manner as in Application Example 1, and the amount of charge was measured and a continuous copying test was conducted. At the same time, a toner with high reproducibility and resolution can be prepared using formula (44).
Claims (1)
ロ基、メチル基、クロル原子、スルホン酸アミド基又は
メチルスルホン基より選ばれた原子又は基を、Ｒはメチ
ル基、エチル基又はフェニルメチル基を、Ｍはクロム、
コバルト又は鉄原子を、Ｘは水素、ナトリウム、カリウ
ム、アンモニウム又は有機アミン塩をそれぞれ表す〕 で表される金属錯塩化合物[Claims] 1. Formula ▲ Numerical formula, chemical formula, table, etc. ▼ (1) [In formula (1), R_1 and R_2 are a hydrogen atom, a nitro group, a methyl group, a chlorine atom, a sulfonic acid amide group or an atom or group selected from methylsulfone group, R is methyl group, ethyl group or phenylmethyl group, M is chromium,
Cobalt or iron atom, X represents hydrogen, sodium, potassium, ammonium or organic amine salt respectively] Metal complex salt compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1142120A JP2554280B2 (en) | 1989-06-06 | 1989-06-06 | Organometallic complex compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1142120A JP2554280B2 (en) | 1989-06-06 | 1989-06-06 | Organometallic complex compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH037768A true JPH037768A (en) | 1991-01-14 |
| JP2554280B2 JP2554280B2 (en) | 1996-11-13 |
Family
ID=15307868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1142120A Expired - Fee Related JP2554280B2 (en) | 1989-06-06 | 1989-06-06 | Organometallic complex compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2554280B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5571457A (en) * | 1994-08-31 | 1996-11-05 | Eastman Kodak Company | Biasable transfer compositions and members having extended electrical life |
| WO2019189209A1 (en) * | 2018-03-27 | 2019-10-03 | 保土谷化学工業株式会社 | Complex salt compound, dye composition, coloring agent and coloring method for anodized aluminum, and method for producing said compound |
-
1989
- 1989-06-06 JP JP1142120A patent/JP2554280B2/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5571457A (en) * | 1994-08-31 | 1996-11-05 | Eastman Kodak Company | Biasable transfer compositions and members having extended electrical life |
| WO2019189209A1 (en) * | 2018-03-27 | 2019-10-03 | 保土谷化学工業株式会社 | Complex salt compound, dye composition, coloring agent and coloring method for anodized aluminum, and method for producing said compound |
| CN111971347A (en) * | 2018-03-27 | 2020-11-20 | 保土谷化学工业株式会社 | Complex salt compound, dye composition, coloring agent for anodized aluminum, coloring method, and method for producing complex salt compound |
| JPWO2019189209A1 (en) * | 2018-03-27 | 2021-03-25 | 保土谷化学工業株式会社 | Complex salt compounds, dye compositions, colorants and coloring methods for anodized aluminum, and methods for producing the compounds. |
| CN111971347B (en) * | 2018-03-27 | 2023-03-24 | 保土谷化学工业株式会社 | Complex salt compound, dye composition, coloring agent for anodized aluminum, coloring method, and method for producing complex salt compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2554280B2 (en) | 1996-11-13 |
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