JPH0354677B2 - - Google Patents
Info
- Publication number
- JPH0354677B2 JPH0354677B2 JP58205879A JP20587983A JPH0354677B2 JP H0354677 B2 JPH0354677 B2 JP H0354677B2 JP 58205879 A JP58205879 A JP 58205879A JP 20587983 A JP20587983 A JP 20587983A JP H0354677 B2 JPH0354677 B2 JP H0354677B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- aminophenol
- parts
- carbamoyl
- 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.)
- Expired - Lifetime
Links
- -1 1-pyridyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 229910052804 chromium Inorganic materials 0.000 claims description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 6
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NHIRTPYVBADBSR-UHFFFAOYSA-J [Na+].[Cr+3].Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O Chemical compound [Na+].[Cr+3].Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O.Oc1ccccc1C([O-])=O NHIRTPYVBADBSR-UHFFFAOYSA-J 0.000 description 2
- 150000001844 chromium Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OMLRRXLWJXURTK-UHFFFAOYSA-N 1-(3-amino-4-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=C(O)C(N)=C1 OMLRRXLWJXURTK-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QQDKXJSYZGJGKJ-UHFFFAOYSA-N 2-amino-3,4,6-trichlorophenol Chemical compound NC1=C(O)C(Cl)=CC(Cl)=C1Cl QQDKXJSYZGJGKJ-UHFFFAOYSA-N 0.000 description 1
- BVWRRBXBWWYODP-UHFFFAOYSA-N 2-amino-3,5-dichlorophenol Chemical compound NC1=C(O)C=C(Cl)C=C1Cl BVWRRBXBWWYODP-UHFFFAOYSA-N 0.000 description 1
- JSHJJLQJRLNBBA-UHFFFAOYSA-N 2-amino-3-chlorophenol Chemical compound NC1=C(O)C=CC=C1Cl JSHJJLQJRLNBBA-UHFFFAOYSA-N 0.000 description 1
- JEASLLCHQHBBGM-UHFFFAOYSA-N 2-amino-4,5-dimethylphenol Chemical compound CC1=CC(N)=C(O)C=C1C JEASLLCHQHBBGM-UHFFFAOYSA-N 0.000 description 1
- WASQBNCGNUTVNI-UHFFFAOYSA-N 2-amino-4,6-dichlorophenol Chemical compound NC1=CC(Cl)=CC(Cl)=C1O WASQBNCGNUTVNI-UHFFFAOYSA-N 0.000 description 1
- BESJCRMQEYZHPM-UHFFFAOYSA-N 2-amino-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N)=C1 BESJCRMQEYZHPM-UHFFFAOYSA-N 0.000 description 1
- OVFOSMHDFYXTCQ-UHFFFAOYSA-N 2-amino-4-bromo-5-methylphenol Chemical compound CC1=CC(O)=C(N)C=C1Br OVFOSMHDFYXTCQ-UHFFFAOYSA-N 0.000 description 1
- JHRIPENGTGSNPJ-UHFFFAOYSA-N 2-amino-4-bromophenol Chemical compound NC1=CC(Br)=CC=C1O JHRIPENGTGSNPJ-UHFFFAOYSA-N 0.000 description 1
- ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-UHFFFAOYSA-N 0.000 description 1
- MHAFRUMLQZZSIN-UHFFFAOYSA-N 2-amino-4-chloro-6-nitrophenol Chemical compound NC1=CC(Cl)=CC([N+]([O-])=O)=C1O MHAFRUMLQZZSIN-UHFFFAOYSA-N 0.000 description 1
- JRCVKCSFJNERAW-UHFFFAOYSA-N 2-amino-4-iodophenol Chemical compound NC1=CC(I)=CC=C1O JRCVKCSFJNERAW-UHFFFAOYSA-N 0.000 description 1
- TUADYTFWZPZZTP-UHFFFAOYSA-N 2-amino-4-methoxyphenol Chemical compound COC1=CC=C(O)C(N)=C1 TUADYTFWZPZZTP-UHFFFAOYSA-N 0.000 description 1
- WZSBYBXNPKFJTA-UHFFFAOYSA-N 2-amino-4-methyl-5-nitrophenol Chemical compound CC1=CC(N)=C(O)C=C1[N+]([O-])=O WZSBYBXNPKFJTA-UHFFFAOYSA-N 0.000 description 1
- RPJUVNYXHUCRMG-UHFFFAOYSA-N 2-amino-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N)=C1 RPJUVNYXHUCRMG-UHFFFAOYSA-N 0.000 description 1
- DRQWUAAWZFIVTF-UHFFFAOYSA-N 2-amino-5-bromophenol Chemical compound NC1=CC=C(Br)C=C1O DRQWUAAWZFIVTF-UHFFFAOYSA-N 0.000 description 1
- SLCFPRSRXASEMX-UHFFFAOYSA-N 2-amino-6-bromo-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC(Br)=C1O SLCFPRSRXASEMX-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
- WQYXEJHVUOSIKM-UHFFFAOYSA-N 2-chloro-n-(2-hydroxynaphthalen-1-yl)acetamide Chemical compound C1=CC=CC2=C(NC(=O)CCl)C(O)=CC=C21 WQYXEJHVUOSIKM-UHFFFAOYSA-N 0.000 description 1
- KHFJTHCIQARPKD-UHFFFAOYSA-N 3-amino-4-hydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C(N)=C1 KHFJTHCIQARPKD-UHFFFAOYSA-N 0.000 description 1
- AVQFHKYAVVQYQO-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1O AVQFHKYAVVQYQO-UHFFFAOYSA-N 0.000 description 1
- ZEWCASRNRWXXSO-UHFFFAOYSA-N 3-amino-4-hydroxybenzonitrile Chemical compound NC1=CC(C#N)=CC=C1O ZEWCASRNRWXXSO-UHFFFAOYSA-N 0.000 description 1
- XIENPRDEHTZGHA-UHFFFAOYSA-N 3-amino-n-ethyl-4-hydroxybenzamide Chemical compound CCNC(=O)C1=CC=C(O)C(N)=C1 XIENPRDEHTZGHA-UHFFFAOYSA-N 0.000 description 1
- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
- KVHHMYZBFBSVDI-UHFFFAOYSA-N 8-aminonaphthalen-2-ol Chemical compound C1=C(O)C=C2C(N)=CC=CC2=C1 KVHHMYZBFBSVDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- VNQABZCSYCTZMS-UHFFFAOYSA-N Orthoform Chemical compound COC(=O)C1=CC=C(O)C(N)=C1 VNQABZCSYCTZMS-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- LJOCHRXHBJRUQD-UHFFFAOYSA-N [2-[(6-hydroxynaphthalen-1-yl)amino]-2-oxoethyl]-trimethylazanium;chloride Chemical compound [Cl-].OC1=CC=C2C(NC(=O)C[N+](C)(C)C)=CC=CC2=C1 LJOCHRXHBJRUQD-UHFFFAOYSA-N 0.000 description 1
- MVEJTHAGYPGJIN-UHFFFAOYSA-N [4-[(7-hydroxynaphthalen-1-yl)amino]-4-oxobutyl]-trimethylazanium;chloride Chemical compound [Cl-].C1=C(O)C=C2C(NC(=O)CCC[N+](C)(C)C)=CC=CC2=C1 MVEJTHAGYPGJIN-UHFFFAOYSA-N 0.000 description 1
- MMYIGCBKXDMDPH-UHFFFAOYSA-N [Br-].C[N+]1(CCCCC1)CCCC(NC1=CC=CC2=CC=C(C=C12)O)=O Chemical compound [Br-].C[N+]1(CCCCC1)CCCC(NC1=CC=CC2=CC=C(C=C12)O)=O MMYIGCBKXDMDPH-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- JKMOZJBQVXKDEQ-UHFFFAOYSA-N benzyl-[2-[(7-hydroxynaphthalen-1-yl)amino]-2-oxoethyl]-dimethylazanium;chloride Chemical compound [Cl-].C=1C=CC2=CC=C(O)C=C2C=1NC(=O)C[N+](C)(C)CC1=CC=CC=C1 JKMOZJBQVXKDEQ-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- UTGYUQOMNFRPBV-UHFFFAOYSA-N ethyl-[2-[(7-hydroxynaphthalen-1-yl)amino]-2-oxoethyl]-dimethylazanium;iodide Chemical compound [I-].C1=C(O)C=C2C(NC(=O)C[N+](C)(C)CC)=CC=CC2=C1 UTGYUQOMNFRPBV-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- ISWNAMNOYHCTSB-UHFFFAOYSA-N methanamine;hydrobromide Chemical compound [Br-].[NH3+]C ISWNAMNOYHCTSB-UHFFFAOYSA-N 0.000 description 1
- SJLXLRKVEXAMOH-UHFFFAOYSA-N n-(6-hydroxynaphthalen-1-yl)-2-pyridin-1-ium-1-ylacetamide;chloride Chemical compound [Cl-].C=1C=CC2=CC(O)=CC=C2C=1NC(=O)C[N+]1=CC=CC=C1 SJLXLRKVEXAMOH-UHFFFAOYSA-N 0.000 description 1
- SSSPBOHEMCUHQS-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)-2-(4-methylmorpholin-4-ium-4-yl)acetamide;chloride Chemical compound [Cl-].C=1C=CC2=CC=C(O)C=C2C=1NC(=O)C[N+]1(C)CCOCC1 SSSPBOHEMCUHQS-UHFFFAOYSA-N 0.000 description 1
- SDOAYPGSKGTTHR-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)-2-pyridin-1-ium-1-ylacetamide;chloride Chemical compound [Cl-].C12=CC(O)=CC=C2C=CC=C1NC(=O)C[N+]1=CC=CC=C1 SDOAYPGSKGTTHR-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- PAAGUICURVYPSN-UHFFFAOYSA-N triethyl-[2-[(7-hydroxynaphthalen-1-yl)amino]-2-oxoethyl]azanium;chloride Chemical compound [Cl-].C1=C(O)C=C2C(NC(=O)C[N+](CC)(CC)CC)=CC=CC2=C1 PAAGUICURVYPSN-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Developing Agents For Electrophotography (AREA)
Description
本発明は金属錯塩化合物に関するものである。
さらに詳細には、本発明は下記一般式(1)
（式中、Ｒは炭素数１〜10のアルキル基、炭素数
１〜４のアルコキシル基、炭素数２〜５のアルコ
キシカルボニル基、アミノカルボニル基、炭素数
２〜５のアルキルアミノカルボニル基、炭素数１
〜３のアルキルスルホニル基、アミノスルホニル
基、炭素数２〜５のアシルアミノ基、ニトロ基、
シアノ基、ハロゲン原子を表わし、ｍは１〜３の
整数であり、ｍが２以上の場合、Ｒは互いに相違
した置換基であることもでき、Ｙは炭素数１〜４
のアルキレン基を表わし、Ｚは炭素数１〜４のア
ルキル基またはベンジル基で置換された４級アン
モニウム基、１−ピリジル基、Ｎ−メチルモルホ
リノ基、Ｎ−メチルピペリジノ基を表わし、Ｍは
クロム原子あるいはコバルト原子を表わし、X
はアニオンを表わす。但し、−NHCO−Ｙ−Ｚ基
はナフタレン環におけるアゾ基の置換位置を１−
位とした場合に５−位あるいは８−位に置換して
いるものとする。）で表わされる新規な２：１型
金属錯塩化合物である。
一般式(1)で表わされる新規な金属錯塩化合物は
種々の用途に於て有用であるが、特に電子写真現
像剤の電荷制御作用に優れており、本発明の金属
錯塩化合物を含有する電子写真現像剤は極めて安
定した帯電特性を示す。その他、本発明の金属錯
塩化合物は、天然繊維、合成繊維およびプラスチ
ツクの染着色に用いても高い堅牢性を有し有用で
ある。
本発明の金属錯塩化合物は、下記一般式(2)
（式中、Ｒ、ｍは前に定義した通りである。）で
表わされるジアゾ成分を常法によりジアゾ化し、
このジアゾ化合物を、下記一般式(3)
（式中、Ｘ
、Ｙ、Ｚは前に定義した通りであ
る。）で表わされるカツプリング成分と常法に従
いカツプリングすることにより、下記一般式(4)
（式中、Ｒ、ｍ、Ｘ
、Ｙ、Ｚは前に定義した通
りである。）で表わ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あるいは有機溶
媒中、常法によりクロム化付与剤あるいはコバル
ト化付与剤で加熱処理することにより、高収率で
得ることができる。本発明で用いられる上記一般
式(2)で表わされるジアゾ成分としては、例えば３
−クロロ−２−アミノフエノール、４−クロロ−
２−アミノフエノール、４−ブロム−２−アミノ
フエノール、５−ブロム−２−アミノフエノー
ル、４−ヨード−２−アミノフエノール、３，５
−ジクロロ−２−アミノフエノール、４，６−ジ
クロロ−２−アミノフエノール、３，４，６−ト
リクロロ−２−アミノフエノール、４−ニトロ−
２−アミノフエノール、５−ニトロ−２−アミノ
フエノール、６−クロロ−４−ニトロ−２−アミ
ノフエノール、４−クロロ−５−ニトロ−２−ア
ミノフエノール、４−クロロ−６−ニトロ−２−
アミノフエノール、６−ブロム−４−ニトロ−２
−アミノフエノール、４−メチル−２−アミノフ
エノール、４−ｔ−ブチル−２−アミノフエノー
ル、４−ｔ−オクチル−２−アミノフエノール、
４，５−ジメチル−２−アミノフエノール、４−
メトキシ−２−アミノフエノール、４−メチル−
５−ニトロ−２−アミノフエノール、４−ブロム
−５−メチル−２−アミノフエノール、４−シア
ノ−２−アミノフエノール、４−アセチル−２−
アミノフエノール、４−メトキシカルボニル−２
−アミノフエノール、４−アミノカルボニル−２
−アミノフエノール、４−エチルアミノカルボニ
ル−２−アミノフエノール、４−アミノスルホニ
ル−２−アミノフエノール、４−ブロピルスルホ
ニル−２−アミノフエノール等があげられる。
また一般式(3)で表わされるカツプリング成分と
しては、Ｎ，Ｎ，Ｎ−トリメチル−Ｎ−〔N′−
（７−ヒドロキシ−１−ナフチル）カルバモイル〕
メチルアンモニウムクロリド、Ｎ，Ｎ，Ｎ−トリ
メチル−Ｎ−〔N′−（６−ヒドロキシ−１−ナフ
チル）カルバモイル〕メチルアンモニウム クロ
リド、Ｎ，Ｎ，Ｎ−トリエチル−Ｎ−〔N′−（７
−ヒドロキシ−１−ナフチル）カルバモイル〕メ
チルアンモニウム クロリド、Ｎ，Ｎ−ジメチル
−Ｎ−エチル−Ｎ−〔N′−（７−ヒドロキシ−１
−ナフチル）カルバモイル〕メチルアンモニウム
ヨージド、Ｎ，Ｎ−ジメチル−Ｎ−ｎ−ブチル
−Ｎ−〔N′−（７−ヒドロキシ−１−ナフチル）
カルバモイル〕メチルアンモニウム プロミド、
Ｎ，Ｎ−ジメチル−Ｎ−ｎ−ブチル−Ｎ−〔N′−
（６−ヒドロキシ−１−ナフチル）カルバモイル〕
メチルアンモニウム クロリド、Ｎ，Ｎ，Ｎ−ト
リメチル−Ｎ−〔N′−（７−ヒドロキシ−１−ナ
フチル）カルバモイル〕プロピルアンモニウム
クロリド、Ｎ，Ｎ，Ｎ−トリメチル−Ｎ−〔N′−
（６−ヒドロキシ−１−ナフチル）カルバモイル〕
プロピルアンモニウムクロリド、Ｎ，Ｎ−ジメチ
ル−Ｎ−ベンジル−Ｎ−〔N′−（７−ヒドロキシ
−１−ナフチル）カルバモイル〕メチルアンモニ
ウム クロリド、Ｎ−メチル−Ｎ−〔N′−（７−
ヒドロキシ−１−ナフチル）カルバモイル〕プロ
ピルピペリジニウム ブロミド、Ｎ−メチル−Ｎ
−〔N′−（７−ヒドロキシ−１−ナフチル）カル
バモイル〕メチルモルホリニウム クロリド、Ｎ
−〔N′−（７−ヒドロキシ−１−ナフチル）カル
バモイル〕メチルピリジニウム クロリド、Ｎ−
〔N′−（６−ヒドロキシ−１−ナフチル）カルバ
モイル〕メチルピリジニウム クロリド等があげ
られる。
以下、実施例により本発明を詳細に説明する。
実施例中、部とは重量部を表わす。
実施例 １
14.4部の４−クロロ−２−アミノフエノールを
26部の濃塩酸および水400部と共にかきまぜた後、
氷冷し０〜５℃とし、亜硝酸ナトリウム6.9部を
加え、同温度で２時間かきまぜてジアゾ化した。
このジアゾ化物を０〜５℃で水300部、10部の水
酸化ナトリウムおよび29.3部のＮ，Ｎ，Ｎ−トリ
メチル−Ｎ−〔N′−（７−ヒドロキシ−１−ナフ
チル）カルバモイル〕メチルアンモニウム クロ
リドの混合液に注入しカツプリング反応を行つた
後、次の構造式を有するモノアゾ化合物を単離し
た。
このモノアゾ化合物を120部のエチレングリコ
ールに溶解し、17.4部のクロムサリチル酸ナトリ
ウムを加え85〜90℃で４時間かきまぜクロム化を
行つた後、30℃まで冷却し、塩酸を加えコンゴレ
ツド酸性として常温で生成物を単離し、50〜60℃
減圧乾燥して下記式、
で示される黒青色微粉末のクロム錯塩化合物45部
を得た。このクロム錯塩化合物の最大吸収波長を
ジメチルホルムアミド溶媒中で測定すると581n
ｍであつた。この錯塩化合物をスチレン−エチル
ヘキシルメタアクリレート共重合物、およびカー
ボンブラツクより成る電子写真現像剤を使用し
て、きわめて鮮明な画像を得ることができた。
なお本実施例で用いられるカツプリング成分
は、８−アミノ−２−ナフトールを氷酢酸中、酢
酸ナトリウムを脱酸剤に使用してクロロ酢酸クロ
リドによりクロロアセチル化し、８−クロロアセ
チルアミノ−２−ナフトールを合成、単離した８
−クロロアセチルアミノ−２−ナフトールをアセ
トンに溶解し、これにガス状のトリメチルアミン
を吹込むことにより得られた。
実施例 ２
実施例１と同様にして得た下記構造、
で表わされるモノアゾ染料53.8部を200部のメチ
ルセロソルブに溶解し18.2部のクロムサリチル酸
ナトリウムを加え100〜105℃で２時間かきまぜク
ロム化を行つた後、20℃まで冷却し、以下実施例
１と同様に処理し下記式、
で示される黒色粉末のクロム錯塩化合物51.2部を
得た。
このクロム錯塩化合物をジメチルホルムアミド
溶媒で最大吸収波長を測定すると594nｍであつ
た。
本実施例に使用したカツプリング成分は、５−
クロロアセチルアミノ−２−ナフトールをピリジ
ン中で加熱することにより容易に得られた。
実施例 ３〜32
実施例１〜２に準じて対称型２：１金属錯塩化
合物を得た。これら化合物の構造、、最大吸収波
長（ジメチルホルムアミド中）、外観を次表にま
とめた。
The present invention relates to metal complex compounds.
More specifically, the present invention is based on the following general formula (1) (In the formula, R is an alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, an aminocarbonyl group, an alkylaminocarbonyl group having 2 to 5 carbon atoms, a carbon Number 1
-3 alkylsulfonyl group, aminosulfonyl group, acylamino group having 2 to 5 carbon atoms, nitro group,
It represents a cyano group or a halogen atom, m is an integer of 1 to 3, and when m is 2 or more, R can be different substituents, and Y has 1 to 4 carbon atoms.
represents an alkylene group, Z represents an alkyl group having 1 to 4 carbon atoms or a quaternary ammonium group substituted with a benzyl group, 1-pyridyl group, N-methylmorpholino group, N-methylpiperidino group, M is a chromium atom Or represent a cobalt atom, X
represents an anion. However, the -NHCO-Y-Z group changes the substitution position of the azo group on the naphthalene ring to 1-
When substituted at the 5- or 8-position, it is assumed that the substitution is made at the 5- or 8-position. ) is a novel 2:1 type metal complex salt compound. The novel metal complex salt compound represented by the general formula (1) is useful in various uses, but it is particularly excellent in the charge control effect of electrophotographic developers, and is suitable for electrophotography containing the metal complex salt compound of the present invention. The developer exhibits extremely stable charging characteristics. In addition, the metal complex compound of the present invention has high fastness and is useful for dyeing natural fibers, synthetic fibers, and plastics. The metal complex salt compound of the present invention has the following general formula (2): (wherein R and m are as defined above) is diazotized by a conventional method,
This diazo compound is expressed by the following general formula (3) (In the formula, X, Y, and Z are as defined above.) By coupling with the coupling component represented by (In the formula, R, m, It can be obtained in high yield by heat treatment with a cobaltization agent or a cobaltization imparting agent. The diazo component represented by the above general formula (2) used in the present invention includes, for example, 3
-chloro-2-aminophenol, 4-chloro-
2-aminophenol, 4-bromo-2-aminophenol, 5-bromo-2-aminophenol, 4-iodo-2-aminophenol, 3,5
-dichloro-2-aminophenol, 4,6-dichloro-2-aminophenol, 3,4,6-trichloro-2-aminophenol, 4-nitro-
2-aminophenol, 5-nitro-2-aminophenol, 6-chloro-4-nitro-2-aminophenol, 4-chloro-5-nitro-2-aminophenol, 4-chloro-6-nitro-2-
Aminophenol, 6-bromo-4-nitro-2
-aminophenol, 4-methyl-2-aminophenol, 4-t-butyl-2-aminophenol, 4-t-octyl-2-aminophenol,
4,5-dimethyl-2-aminophenol, 4-
Methoxy-2-aminophenol, 4-methyl-
5-nitro-2-aminophenol, 4-bromo-5-methyl-2-aminophenol, 4-cyano-2-aminophenol, 4-acetyl-2-
Aminophenol, 4-methoxycarbonyl-2
-aminophenol, 4-aminocarbonyl-2
-aminophenol, 4-ethylaminocarbonyl-2-aminophenol, 4-aminosulfonyl-2-aminophenol, 4-bropylsulfonyl-2-aminophenol, and the like. In addition, as a coupling component represented by general formula (3), N,N,N-trimethyl-N-[N'-
(7-hydroxy-1-naphthyl)carbamoyl]
Methylammonium chloride, N,N,N-trimethyl-N-[N'-(6-hydroxy-1-naphthyl)carbamoyl]methylammonium chloride, N,N,N-triethyl-N-[N'-(7
-hydroxy-1-naphthyl)carbamoyl]methylammonium chloride, N,N-dimethyl-N-ethyl-N-[N'-(7-hydroxy-1
-naphthyl)carbamoyl]methylammonium iodide, N,N-dimethyl-N-n-butyl-N-[N'-(7-hydroxy-1-naphthyl)
Carbamoyl] methylammonium bromide,
N,N-dimethyl-N-n-butyl-N-[N'-
(6-hydroxy-1-naphthyl)carbamoyl]
Methylammonium chloride, N,N,N-trimethyl-N-[N'-(7-hydroxy-1-naphthyl)carbamoyl]propylammonium
Chloride, N,N,N-trimethyl-N-[N'-
(6-hydroxy-1-naphthyl)carbamoyl]
Propylammonium chloride, N,N-dimethyl-N-benzyl-N-[N'-(7-hydroxy-1-naphthyl)carbamoyl]methylammonium chloride, N-methyl-N-[N'-(7-
Hydroxy-1-naphthyl)carbamoyl]propylpiperidinium bromide, N-methyl-N
-[N'-(7-hydroxy-1-naphthyl)carbamoyl]methylmorpholinium chloride, N
-[N'-(7-hydroxy-1-naphthyl)carbamoyl]methylpyridinium chloride, N-
Examples include [N'-(6-hydroxy-1-naphthyl)carbamoyl]methylpyridinium chloride. Hereinafter, the present invention will be explained in detail with reference to Examples.
In the examples, parts represent parts by weight. Example 1 14.4 parts of 4-chloro-2-aminophenol
After stirring with 26 parts of concentrated hydrochloric acid and 400 parts of water,
The mixture was cooled with ice to 0 to 5°C, 6.9 parts of sodium nitrite was added, and the mixture was stirred at the same temperature for 2 hours to form diazotization.
This diazotide was mixed at 0 to 5°C with 300 parts of water, 10 parts of sodium hydroxide and 29.3 parts of N,N,N-trimethyl-N-[N'-(7-hydroxy-1-naphthyl)carbamoyl]methylammonium. After injecting into a chloride mixture and performing a coupling reaction, a monoazo compound having the following structural formula was isolated. This monoazo compound was dissolved in 120 parts of ethylene glycol, 17.4 parts of sodium chromium salicylate was added, and the mixture was stirred at 85-90°C for 4 hours to perform chromation. After that, it was cooled to 30°C, and hydrochloric acid was added to make it a Congoled acid. Isolate the product and store at 50-60℃
Dry under reduced pressure and use the following formula, 45 parts of a chromium complex salt compound as a black-blue fine powder was obtained. When the maximum absorption wavelength of this chromium complex salt compound was measured in dimethylformamide solvent, it was 581n.
It was m. By using this complex salt compound in an electrophotographic developer consisting of styrene-ethylhexyl methacrylate copolymer and carbon black, extremely clear images could be obtained. The coupling component used in this example was obtained by chloroacetylating 8-amino-2-naphthol with chloroacetic acid chloride in glacial acetic acid using sodium acetate as a deoxidizing agent. synthesized and isolated 8
It was obtained by dissolving -chloroacetylamino-2-naphthol in acetone and blowing gaseous trimethylamine into the solution. Example 2 The following structure obtained in the same manner as Example 1, 53.8 parts of the monoazo dye represented by was dissolved in 200 parts of methyl cellosolve, 18.2 parts of sodium chromium salicylate was added, and the mixture was stirred at 100 to 105°C for 2 hours to perform chromation, and then cooled to 20°C. Processed in the same way, the following formula, 51.2 parts of a black powder chromium complex salt compound represented by was obtained. When the maximum absorption wavelength of this chromium complex salt compound was measured using dimethylformamide solvent, it was 594 nm. The coupling component used in this example was 5-
It was easily obtained by heating chloroacetylamino-2-naphthol in pyridine. Examples 3-32 Symmetrical 2:1 metal complex compounds were obtained according to Examples 1-2. The structure, maximum absorption wavelength (in dimethylformamide), and appearance of these compounds are summarized in the table below.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
Claims (1)
１〜４のアルコキシ基、炭素数２〜５のアルコキ
シカルボニル基、アミノカルボニル基、炭素数２
〜５のアルキルアミノカルボニル基、炭素数１〜
３のアルキルスルホニル基、アミノスルホニル
基、炭素数２〜５のアシルアミノ基、ニトロ基、
シアノ基、ハロゲン原子を表わし、ｍは１〜３の
整数であり、ｍが２以上の場合、Ｒは互いに相違
した置換基であることもでき、Ｙは炭素数１〜４
のアルキレン基を表わし、Ｚは炭素数１〜４のア
ルキル基またはベンジル基で置換された４級アン
モニウム基、１−ピリジル基、Ｎ−メチルモルホ
リノ基、Ｎ−メチルピペリジノ基を表わし、Ｍは
クロム原子あるいはコバルト原子を表わし、X
はアニオンを表わす。但し、−NHCO−Ｙ−Ｚ基
はナフタレン環におけるアゾ基の置換位置を１−
位とした場合に５−位あるいは８−位に置換して
いるものとする。）で表わされる対称型２：１金
属錯塩化合物。[Claims] 1 The following general formula (1) (In the formula, R is an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, an aminocarbonyl group, or a carbon number 2
~5 alkylaminocarbonyl group, carbon number 1~
3 alkylsulfonyl group, aminosulfonyl group, acylamino group having 2 to 5 carbon atoms, nitro group,
It represents a cyano group or a halogen atom, m is an integer of 1 to 3, and when m is 2 or more, R can be different substituents, and Y has 1 to 4 carbon atoms.
represents an alkylene group, Z represents an alkyl group having 1 to 4 carbon atoms or a quaternary ammonium group substituted with a benzyl group, 1-pyridyl group, N-methylmorpholino group, N-methylpiperidino group, M is a chromium atom Or represent a cobalt atom, X
represents an anion. However, the -NHCO-Y-Z group changes the substitution position of the azo group on the naphthalene ring to 1-
When substituted at the 5- or 8-position, it is assumed that the substitution is made at the 5- or 8-position. ) A symmetrical 2:1 metal complex compound represented by
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58205879A JPS6097990A (en) | 1983-11-04 | 1983-11-04 | Metal complex salt compound |
| DE8484112827T DE3482119D1 (en) | 1983-11-04 | 1984-10-24 | METAL COMPLEXES. |
| EP84112827A EP0141377B1 (en) | 1983-11-04 | 1984-10-24 | Metal complexes |
| US06/668,323 US4563409A (en) | 1983-11-04 | 1984-11-05 | Azo moiety containing metal complexes in toners |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58205879A JPS6097990A (en) | 1983-11-04 | 1983-11-04 | Metal complex salt compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6097990A JPS6097990A (en) | 1985-05-31 |
| JPH0354677B2 true JPH0354677B2 (en) | 1991-08-20 |
Family
ID=16514240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58205879A Granted JPS6097990A (en) | 1983-11-04 | 1983-11-04 | Metal complex salt compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6097990A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2727959A1 (en) | 2008-07-30 | 2010-02-04 | Sk Energy, Co., Ltd. | Novel coordination complexes and process of producing polycarbonate by copolymerization of carbon dioxide and epoxide using the same as catalyst |
-
1983
- 1983-11-04 JP JP58205879A patent/JPS6097990A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6097990A (en) | 1985-05-31 |
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