JPH0334501B2 - - Google Patents

Info

Publication number: JPH0334501B2
Authority: JP; Japan
Prior art keywords: formula; parts; alkyl; substituted; alkoxy
Prior art date: 1982-09-02
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

Application number

JP15169582A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5943064A (ja

Inventor

Shinji Suzuki

Mitsuaki Tsunoda

Mitsuru Kurosawa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nippon Kayaku Co Ltd

Original Assignee

Nippon Kayaku Co Ltd

Priority date (The priority date 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 date listed.)

1982-09-02

Filing date

1982-09-02

Publication date

1991-05-22

1982-09-02 Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd

1982-09-02 Priority to JP15169582A priority Critical patent/JPS5943064A/ja

1984-03-09 Publication of JPS5943064A publication Critical patent/JPS5943064A/ja

1991-05-22 Publication of JPH0334501B2 publication Critical patent/JPH0334501B2/ja

Status Granted legal-status Critical Current

Links

-1 azo compound Chemical class 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 8
238000000034 method Methods 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 2
238000004040 coloring Methods 0.000 claims description 2
239000012024 dehydrating agents‎ Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000011368 organic material Substances 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000243 solution Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000975 dye Substances 0.000 description 7
238000004043 dyeing Methods 0.000 description 6
239000000835 fiber Substances 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
239000002270 dispersing agent Substances 0.000 description 5
229920000728 polyester Polymers 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
239000004743 Polypropylene Substances 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
229920001155 polypropylene Polymers 0.000 description 4
238000007639 printing Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 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
239000013078 crystal Substances 0.000 description 3
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000000465 moulding Methods 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
238000010018 discharge printing Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229920000620 organic polymer Polymers 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
239000002861 polymer material Substances 0.000 description 2
238000004513 sizing Methods 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000009987 spinning Methods 0.000 description 2
239000004753 textile Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical class N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 description 1
GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical group NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
NATVSFWWYVJTAZ-UHFFFAOYSA-N 2,4,6-trichloroaniline Chemical group NC1=C(Cl)C=C(Cl)C=C1Cl NATVSFWWYVJTAZ-UHFFFAOYSA-N 0.000 description 1
KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical group NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical group NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
KBJGBAOGDZOYIZ-UHFFFAOYSA-N 2,5-dimethoxy-4-[(4-nitrophenyl)diazenyl]aniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C=CC(=CC=2)[N+]([O-])=O)=C1OC KBJGBAOGDZOYIZ-UHFFFAOYSA-N 0.000 description 1
MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical group NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 1
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical group NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical group COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
PFRYFZZSECNQOL-UHFFFAOYSA-N 2-methyl-4-[(2-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(C)=CC(N=NC=2C(=CC=CC=2)C)=C1 PFRYFZZSECNQOL-UHFFFAOYSA-N 0.000 description 1
XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical group CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
AIMBUQYGNMOHHF-UHFFFAOYSA-N 2-phenyldiazenylaniline;hydrochloride Chemical compound Cl.NC1=CC=CC=C1N=NC1=CC=CC=C1 AIMBUQYGNMOHHF-UHFFFAOYSA-N 0.000 description 1
CTBWWPIIRKWDDL-UHFFFAOYSA-N 3-amino-n,n-diethylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC(N)=C1 CTBWWPIIRKWDDL-UHFFFAOYSA-N 0.000 description 1
APIVVDFBBPFBDZ-UHFFFAOYSA-N 3-amino-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(N)=C1 APIVVDFBBPFBDZ-UHFFFAOYSA-N 0.000 description 1
PGCYKJPSIKCLNX-UHFFFAOYSA-N 3-amino-n-ethylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=CC(N)=C1 PGCYKJPSIKCLNX-UHFFFAOYSA-N 0.000 description 1
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
WEZAHYDFZNTGKE-UHFFFAOYSA-N 3-ethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1 WEZAHYDFZNTGKE-UHFFFAOYSA-N 0.000 description 1
XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
UNBOSJFEZZJZLR-UHFFFAOYSA-N 4-(4-nitrophenylazo)aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 UNBOSJFEZZJZLR-UHFFFAOYSA-N 0.000 description 1
KNRCFYFPEMWZPT-UHFFFAOYSA-N 4-[(2-chlorophenyl)diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1Cl KNRCFYFPEMWZPT-UHFFFAOYSA-N 0.000 description 1
VDUXKWBSXPCZPG-UHFFFAOYSA-N 4-[(2-methylphenyl)diazenyl]aniline Chemical compound CC1=CC=CC=C1N=NC1=CC=C(N)C=C1 VDUXKWBSXPCZPG-UHFFFAOYSA-N 0.000 description 1
QBTQMGBZIHCFBT-UHFFFAOYSA-N 4-[(2-nitrophenyl)diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1[N+]([O-])=O QBTQMGBZIHCFBT-UHFFFAOYSA-N 0.000 description 1
KCOITMFSLVDOGO-UHFFFAOYSA-N 4-[(3-methylphenyl)diazenyl]aniline Chemical compound CC1=CC=CC(N=NC=2C=CC(N)=CC=2)=C1 KCOITMFSLVDOGO-UHFFFAOYSA-N 0.000 description 1
MDMDJAOEKAAIGH-UHFFFAOYSA-N 4-[(3-nitrophenyl)diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC([N+]([O-])=O)=C1 MDMDJAOEKAAIGH-UHFFFAOYSA-N 0.000 description 1
FSZLUNAODPMYOV-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]benzonitrile Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(C#N)C=C1 FSZLUNAODPMYOV-UHFFFAOYSA-N 0.000 description 1
NCKPQOUTAMSEAO-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]phenol Chemical compound Nc1ccc(cc1)N=Nc1ccc(O)cc1 NCKPQOUTAMSEAO-UHFFFAOYSA-N 0.000 description 1
YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical group COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 1
RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical group COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
DSBIJCMXAIKKKI-UHFFFAOYSA-N 5-nitro-o-toluidine Chemical group CC1=CC=C([N+]([O-])=O)C=C1N DSBIJCMXAIKKKI-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
229920002284 Cellulose triacetate Polymers 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
108010088249 Monogen Proteins 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
MKYWTNGRWMLQAX-UHFFFAOYSA-N NC(C1=CC=C(C=C1)OC)S(=O)(=O)C(C1=CC=C(C=C1)OC)N Chemical compound NC(C1=CC=C(C=C1)OC)S(=O)(=O)C(C1=CC=C(C=C1)OC)N MKYWTNGRWMLQAX-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
MRQIXHXHHPWVIL-ISLYRVAYSA-N Sudan I Chemical compound OC1=CC=C2C=CC=CC2=C1\N=N\C1=CC=CC=C1 MRQIXHXHHPWVIL-ISLYRVAYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
HUIYGGQINIVDNW-UHFFFAOYSA-N butyl anthranilate Chemical compound CCCCOC(=O)C1=CC=CC=C1N HUIYGGQINIVDNW-UHFFFAOYSA-N 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical group NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
229940052295 esters of aminobenzoic acid for local anesthesia Drugs 0.000 description 1
239000004744 fabric Substances 0.000 description 1
238000005562 fading Methods 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000007788 liquid Substances 0.000 description 1
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 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
UDQNZSNRUYGNCC-UHFFFAOYSA-N methyl 4-(anilinodiazenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N=NNC1=CC=CC=C1 UDQNZSNRUYGNCC-UHFFFAOYSA-N 0.000 description 1
LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
AZKDTTQQTKDXLH-UHFFFAOYSA-N napthalene-2-carbonitrile Natural products C1=CC=CC2=CC(C#N)=CC=C21 AZKDTTQQTKDXLH-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
238000012805 post-processing Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
NBFQYHKHPBMJJV-UHFFFAOYSA-N risocaine Chemical compound CCCOC(=O)C1=CC=C(N)C=C1 NBFQYHKHPBMJJV-UHFFFAOYSA-N 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000010025 steaming Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1

Landscapes

Coloring (AREA)

JP15169582A 1982-09-02 1982-09-02 アゾ化合物、その製法及びそれを用いる着色法 Granted JPS5943064A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP15169582A JPS5943064A (ja)	1982-09-02	1982-09-02	アゾ化合物、その製法及びそれを用いる着色法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP15169582A JPS5943064A (ja)	1982-09-02	1982-09-02	アゾ化合物、その製法及びそれを用いる着色法

Publications (2)

Publication Number	Publication Date
JPS5943064A JPS5943064A (ja)	1984-03-09
JPH0334501B2 true JPH0334501B2 (pl)	1991-05-22

Family

ID=15524238

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP15169582A Granted JPS5943064A (ja)	1982-09-02	1982-09-02	アゾ化合物、その製法及びそれを用いる着色法

Country Status (1)

Country	Link
JP (1)	JPS5943064A (pl)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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DE3634393A1 (de) *	1986-10-09	1988-04-14	Basf Ag	Solventfarbstoffe mit carbonsaeurefunktionen

1982
- 1982-09-02 JP JP15169582A patent/JPS5943064A/ja active Granted

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Publication number	Publication date
JPS5943064A (ja)	1984-03-09

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