JPH0147499B2 - - Google Patents
Info
- Publication number
- JPH0147499B2 JPH0147499B2 JP55147680A JP14768080A JPH0147499B2 JP H0147499 B2 JPH0147499 B2 JP H0147499B2 JP 55147680 A JP55147680 A JP 55147680A JP 14768080 A JP14768080 A JP 14768080A JP H0147499 B2 JPH0147499 B2 JP H0147499B2
- Authority
- JP
- Japan
- Prior art keywords
- nitro
- chlorine
- substituted
- following formula
- dye
- 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
Links
- 239000000975 dye Substances 0.000 claims description 32
- 229920000728 polyester Polymers 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- -1 methoxy, ethoxy Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 239000011550 stock solution Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 239000004594 Masterbatch (MB) Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical class C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- MLKMMRIRZHOWMH-UHFFFAOYSA-N 14,15,17,18-tetrachloro-2,11-diazapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1(20),3,5,7,9,11,13,15,17-nonaen-19-one Chemical compound C1=C(Cl)C(Cl)=C2C(Cl)=C(Cl)C(=O)C3=C2C1=NC1=C(C=CC=C2)C2=CN13 MLKMMRIRZHOWMH-UHFFFAOYSA-N 0.000 description 1
- XOEDMTWJHKZQNT-UHFFFAOYSA-N 17,18-dichloro-2,11-diazapentacyclo[10.7.1.02,10.04,9.016,20]icosa-1(20),3,5,7,9,11,13,15,17-nonaen-19-one Chemical compound C1=CC=CC2=CN3C(C(=O)C(Cl)=C4Cl)=C5C4=CC=CC5=NC3=C21 XOEDMTWJHKZQNT-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- QGXQXRTVKOXDDC-UHFFFAOYSA-N 3,4,5-trichlorophthalic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1C(O)=O QGXQXRTVKOXDDC-UHFFFAOYSA-N 0.000 description 1
- YUDBKSANIWMLCU-UHFFFAOYSA-N 3,4-dichlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=C1C(O)=O YUDBKSANIWMLCU-UHFFFAOYSA-N 0.000 description 1
- FLKHCKPUJWBHCW-UHFFFAOYSA-N 3,6-dichlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1C(O)=O FLKHCKPUJWBHCW-UHFFFAOYSA-N 0.000 description 1
- UERPUZBSSSAZJE-UHFFFAOYSA-N 3-chlorophthalic anhydride Chemical compound ClC1=CC=CC2=C1C(=O)OC2=O UERPUZBSSSAZJE-UHFFFAOYSA-N 0.000 description 1
- GAIPRQZXSYSCRD-UHFFFAOYSA-N 4,5-dichloro-2-benzofuran-1,3-dione Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1Cl GAIPRQZXSYSCRD-UHFFFAOYSA-N 0.000 description 1
- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-N sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonic acid Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Artificial Filaments (AREA)
- Polyesters Or Polycarbonates (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH9590/79A CH650523A5 (de) | 1979-10-25 | 1979-10-25 | Phthaloperinon-farbstoffe. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5667369A JPS5667369A (en) | 1981-06-06 |
| JPH0147499B2 true JPH0147499B2 (en, 2012) | 1989-10-13 |
Family
ID=4353559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14768080A Granted JPS5667369A (en) | 1979-10-25 | 1980-10-23 | Phthaloperinone compound |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4417014A (en, 2012) |
| JP (1) | JPS5667369A (en, 2012) |
| BR (1) | BR8006857A (en, 2012) |
| CH (1) | CH650523A5 (en, 2012) |
| DE (1) | DE3038899A1 (en, 2012) |
| ES (1) | ES8202048A1 (en, 2012) |
| FR (1) | FR2467871B1 (en, 2012) |
| GB (1) | GB2062665B (en, 2012) |
| HK (1) | HK29886A (en, 2012) |
| IT (1) | IT1128336B (en, 2012) |
| KE (1) | KE3612A (en, 2012) |
| MY (1) | MY8600531A (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4027607A1 (de) * | 1990-08-31 | 1992-03-05 | Bayer Ag | Heterocyclische verbindungen |
| EP0639624A1 (de) * | 1993-08-19 | 1995-02-22 | Bayer Ag | Phthaloperinonfarbstoffe |
| DE4417746A1 (de) * | 1994-05-20 | 1995-11-23 | Bayer Ag | Neue Farbstoffe zum Massefärben von Kunststoffen |
| DE19548453A1 (de) * | 1995-12-22 | 1997-06-26 | Bayer Ag | Verfahren zur Herstellung polycyclischer Verbindungen |
| WO2010121943A2 (en) * | 2009-04-22 | 2010-10-28 | Dystar Colours Deutschland Gmbh | Dyes for polymer coloration, their preparation and their use |
| TW201510117A (zh) * | 2013-06-28 | 2015-03-16 | Nippon Kayaku Kk | 紫外線硬化型硬質塗敷樹脂組合物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1166701A (fr) | 1957-02-08 | 1958-11-14 | Cfmc | Procédé de teinture des fibres synthétiques à base de polyesters |
| FR1467734A (fr) * | 1965-02-09 | 1967-01-27 | Basf Ag | Nouveaux colorants de la phtalopérinone et procédé pour leur préparation |
| DE1282817B (de) | 1965-02-09 | 1968-11-14 | Basf Ag | Verfahren zur Herstellung von Phthaloperinonfarbstoffen |
| FR1472645A (en, 2012) * | 1965-03-26 | 1967-05-24 | ||
| DE1569664C3 (de) * | 1967-01-18 | 1975-12-04 | Basf Ag, 6700 Ludwigshafen | Phthaloperinonfarbstoffe und Verfahren zu ihrer Herstellung |
| FR1581420A (en, 2012) | 1967-09-21 | 1969-09-12 | ||
| CA970907A (en) | 1970-07-10 | 1975-07-15 | Rutger Neeff | Exhaust process for the dyeing of synthetic fibre materials |
| US3909442A (en) | 1974-01-07 | 1975-09-30 | American Cyanamid Co | Solubilized orange dye (dialkylsulfonamide derivative) |
| DE2424542A1 (de) * | 1974-05-21 | 1975-12-11 | Bayer Ag | Polycyclische farbstoffe |
| DE2447228A1 (de) * | 1974-10-03 | 1976-04-22 | Hoechst Ag | Perinon-verbindungen, verfahren zu deren herstellung und ihre verwendung als farbmittel |
-
1979
- 1979-10-25 CH CH9590/79A patent/CH650523A5/de not_active IP Right Cessation
-
1980
- 1980-10-15 DE DE19803038899 patent/DE3038899A1/de not_active Withdrawn
- 1980-10-21 GB GB8033855A patent/GB2062665B/en not_active Expired
- 1980-10-22 IT IT49967/80A patent/IT1128336B/it active
- 1980-10-23 JP JP14768080A patent/JPS5667369A/ja active Granted
- 1980-10-24 FR FR8022829A patent/FR2467871B1/fr not_active Expired
- 1980-10-24 BR BR8006857A patent/BR8006857A/pt unknown
- 1980-10-24 ES ES496264A patent/ES8202048A1/es not_active Expired
-
1982
- 1982-08-18 US US06/409,112 patent/US4417014A/en not_active Expired - Lifetime
-
1986
- 1986-03-06 KE KE3612A patent/KE3612A/xx unknown
- 1986-04-24 HK HK298/86A patent/HK29886A/xx unknown
- 1986-12-30 MY MY531/86A patent/MY8600531A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT8049967A0 (it) | 1980-10-22 |
| MY8600531A (en) | 1986-12-31 |
| FR2467871A1 (fr) | 1981-04-30 |
| FR2467871B1 (fr) | 1985-10-18 |
| ES496264A0 (es) | 1982-01-16 |
| GB2062665B (en) | 1983-05-18 |
| GB2062665A (en) | 1981-05-28 |
| DE3038899A1 (de) | 1981-05-07 |
| JPS5667369A (en) | 1981-06-06 |
| IT1128336B (it) | 1986-05-28 |
| CH650523A5 (de) | 1985-07-31 |
| BR8006857A (pt) | 1981-04-28 |
| HK29886A (en) | 1986-05-02 |
| ES8202048A1 (es) | 1982-01-16 |
| KE3612A (en) | 1986-03-27 |
| US4417014A (en) | 1983-11-22 |
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