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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58205879A JPS6097990A (ja) | 1983-11-04 | 1983-11-04 | 金属錯塩化合物 |
| DE8484112827T DE3482119D1 (de) | 1983-11-04 | 1984-10-24 | Metallkomplexe. |
| 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 (ja) | 1983-11-04 | 1983-11-04 | 金属錯塩化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6097990A JPS6097990A (ja) | 1985-05-31 |
| JPH0354677B2 true JPH0354677B2 (enrdf_load_stackoverflow) | 1991-08-20 |
Family
ID=16514240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58205879A Granted JPS6097990A (ja) | 1983-11-04 | 1983-11-04 | 金属錯塩化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6097990A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2307477A4 (en) | 2008-07-30 | 2014-12-10 | Sk Innovation Co Ltd | NOVEL COORDINATION COMPLEXES AND METHOD FOR THE PRODUCTION OF POLYCARBONATES BY COPOLYMERIZATION OF CARBON DIOXIDE AND EPOXYDIDE THEREOF AS A CATALYST |
-
1983
- 1983-11-04 JP JP58205879A patent/JPS6097990A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6097990A (ja) | 1985-05-31 |
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