JPS6247461B2 - - Google Patents
Info
- Publication number
- JPS6247461B2 JPS6247461B2 JP56008992A JP899281A JPS6247461B2 JP S6247461 B2 JPS6247461 B2 JP S6247461B2 JP 56008992 A JP56008992 A JP 56008992A JP 899281 A JP899281 A JP 899281A JP S6247461 B2 JPS6247461 B2 JP S6247461B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- parts
- resistance
- absorption wavelength
- fiber
- 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
- 238000000034 method Methods 0.000 claims description 13
- 239000011368 organic material Substances 0.000 claims description 6
- 238000004040 coloring Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 description 52
- 239000000835 fiber Substances 0.000 description 42
- 238000000859 sublimation Methods 0.000 description 29
- 230000008022 sublimation Effects 0.000 description 29
- 239000000975 dye Substances 0.000 description 27
- 238000010521 absorption reaction Methods 0.000 description 26
- 238000004043 dyeing Methods 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LOZJNNNVLREXGU-UHFFFAOYSA-N 3-amino-4,5,6,7-tetrachloroisoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(N)=NC2=O LOZJNNNVLREXGU-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- CUVAUYUUVFGQAI-UHFFFAOYSA-N 3,3,4,5,6,7-hexachloro-2h-isoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)NC(Cl)(Cl)C2=C1Cl CUVAUYUUVFGQAI-UHFFFAOYSA-N 0.000 description 7
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical group NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 5
- 229920002994 synthetic fiber Polymers 0.000 description 5
- 239000012209 synthetic fiber Substances 0.000 description 5
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- 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 4
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical group C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- FLROJJGKUKLCAE-UHFFFAOYSA-N 3-amino-2-methylphenol Chemical compound CC1=C(N)C=CC=C1O FLROJJGKUKLCAE-UHFFFAOYSA-N 0.000 description 3
- JSWVCUXQICMATE-UHFFFAOYSA-N 4-amino-2,5-dimethylphenol Chemical compound CC1=CC(O)=C(C)C=C1N JSWVCUXQICMATE-UHFFFAOYSA-N 0.000 description 3
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 2
- WKOJOGYKEWTXHX-UHFFFAOYSA-N 2-amino-6-iodophenol Chemical compound NC1=CC=CC(I)=C1O WKOJOGYKEWTXHX-UHFFFAOYSA-N 0.000 description 2
- AACMNEWXGKOJJK-UHFFFAOYSA-N 2-amino-6-nitrophenol Chemical compound NC1=CC=CC([N+]([O-])=O)=C1O AACMNEWXGKOJJK-UHFFFAOYSA-N 0.000 description 2
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- 229940018563 3-aminophenol Drugs 0.000 description 2
- ZWWOYERTGZZDMF-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3,3-dimethoxy-2h-isoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(OC)(OC)NC2=O ZWWOYERTGZZDMF-UHFFFAOYSA-N 0.000 description 2
- ABJQKDJOYSQVFX-UHFFFAOYSA-N 4-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=C(O)C2=C1 ABJQKDJOYSQVFX-UHFFFAOYSA-N 0.000 description 2
- DVECBUWKXMPCAA-UHFFFAOYSA-N 5-amino-2,3-dimethylphenol Chemical compound CC1=CC(N)=CC(O)=C1C DVECBUWKXMPCAA-UHFFFAOYSA-N 0.000 description 2
- WSUYONLKFXZZRV-UHFFFAOYSA-N 7-aminonaphthalen-2-ol Chemical compound C1=CC(O)=CC2=CC(N)=CC=C21 WSUYONLKFXZZRV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 alkylbenzene sulfonates Chemical class 0.000 description 2
- SBXKRBZKPQBLOD-UHFFFAOYSA-N aminohydroquinone Chemical compound NC1=CC(O)=CC=C1O SBXKRBZKPQBLOD-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- MGCQJHPUHOKHLO-UHFFFAOYSA-N 2,3,3,4,5,6-hexachloroisoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C2C(Cl)(Cl)N(Cl)C(=O)C2=C1 MGCQJHPUHOKHLO-UHFFFAOYSA-N 0.000 description 1
- GQKCXAPXDGFMKF-UHFFFAOYSA-N 2-amino-3,5-dimethylphenol Chemical compound CC1=CC(C)=C(N)C(O)=C1 GQKCXAPXDGFMKF-UHFFFAOYSA-N 0.000 description 1
- CAMQCQPKZNSFND-UHFFFAOYSA-N 2-amino-3,6-dimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1N CAMQCQPKZNSFND-UHFFFAOYSA-N 0.000 description 1
- VMFLCURUMAEIAO-UHFFFAOYSA-N 2-amino-3-iodophenol Chemical compound NC1=C(O)C=CC=C1I VMFLCURUMAEIAO-UHFFFAOYSA-N 0.000 description 1
- FEDLEBCVFZMHBP-UHFFFAOYSA-N 2-amino-3-methylphenol Chemical compound CC1=CC=CC(O)=C1N FEDLEBCVFZMHBP-UHFFFAOYSA-N 0.000 description 1
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 description 1
- QDGJHZNOQSIFAT-UHFFFAOYSA-N 2-amino-4-chloro-5-methylphenol Chemical compound CC1=CC(O)=C(N)C=C1Cl QDGJHZNOQSIFAT-UHFFFAOYSA-N 0.000 description 1
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-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
- FZCQMIRJCGWWCL-UHFFFAOYSA-N 2-amino-5-chlorophenol Chemical compound NC1=CC=C(Cl)C=C1O FZCQMIRJCGWWCL-UHFFFAOYSA-N 0.000 description 1
- NXBSMRUIIBNDSL-UHFFFAOYSA-N 2-amino-5-iodophenol Chemical compound NC1=CC=C(I)C=C1O NXBSMRUIIBNDSL-UHFFFAOYSA-N 0.000 description 1
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 description 1
- ALQKEYVDQYGZDN-UHFFFAOYSA-N 2-amino-6-methylphenol Chemical compound CC1=CC=CC(N)=C1O ALQKEYVDQYGZDN-UHFFFAOYSA-N 0.000 description 1
- XSBKXUJEVYHSNO-UHFFFAOYSA-N 3-amino-2,6-dimethylphenol Chemical compound CC1=CC=C(N)C(C)=C1O XSBKXUJEVYHSNO-UHFFFAOYSA-N 0.000 description 1
- BOAJMGPOMJTXHH-UHFFFAOYSA-N 3-amino-4,5-dimethylphenol Chemical compound CC1=CC(O)=CC(N)=C1C BOAJMGPOMJTXHH-UHFFFAOYSA-N 0.000 description 1
- FWUALUHYKLDYAN-UHFFFAOYSA-N 3-amino-4-chlorophenol Chemical compound NC1=CC(O)=CC=C1Cl FWUALUHYKLDYAN-UHFFFAOYSA-N 0.000 description 1
- NUNAWQZKZVVELQ-UHFFFAOYSA-N 3-amino-4-methylphenol Chemical compound CC1=CC=C(O)C=C1N NUNAWQZKZVVELQ-UHFFFAOYSA-N 0.000 description 1
- MOJYWQKYSWDYHR-UHFFFAOYSA-N 3-amino-5-iodophenol Chemical compound NC1=CC(O)=CC(I)=C1 MOJYWQKYSWDYHR-UHFFFAOYSA-N 0.000 description 1
- AXQBFCIPQJXBJR-UHFFFAOYSA-N 3-amino-6-chloro-2-methylphenol Chemical compound CC1=C(N)C=CC(Cl)=C1O AXQBFCIPQJXBJR-UHFFFAOYSA-N 0.000 description 1
- ZHVPTERSBUMMHK-UHFFFAOYSA-N 3-aminonaphthalen-2-ol Chemical compound C1=CC=C2C=C(O)C(N)=CC2=C1 ZHVPTERSBUMMHK-UHFFFAOYSA-N 0.000 description 1
- OMVFXCQLSCPJNR-UHFFFAOYSA-N 4-amino-2,6-dimethylphenol Chemical compound CC1=CC(N)=CC(C)=C1O OMVFXCQLSCPJNR-UHFFFAOYSA-N 0.000 description 1
- QPVZPORQYZKIRM-UHFFFAOYSA-N 4-amino-2-chloro-5-methylphenol Chemical compound CC1=CC(O)=C(Cl)C=C1N QPVZPORQYZKIRM-UHFFFAOYSA-N 0.000 description 1
- ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 description 1
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 description 1
- PNLPXABQLXSICH-UHFFFAOYSA-N 4-amino-3-chlorophenol Chemical compound NC1=CC=C(O)C=C1Cl PNLPXABQLXSICH-UHFFFAOYSA-N 0.000 description 1
- LVXHSULEIVXXMO-UHFFFAOYSA-N 4-amino-3-iodophenol Chemical compound NC1=CC=C(O)C=C1I LVXHSULEIVXXMO-UHFFFAOYSA-N 0.000 description 1
- IQXUIDYRTHQTET-UHFFFAOYSA-N 4-amino-3-nitrophenol Chemical compound NC1=CC=C(O)C=C1[N+]([O-])=O IQXUIDYRTHQTET-UHFFFAOYSA-N 0.000 description 1
- HZVWUBNSJFILOV-UHFFFAOYSA-N 4-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=CC(O)=CC2=C1 HZVWUBNSJFILOV-UHFFFAOYSA-N 0.000 description 1
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 description 1
- ASWULCVCLWLUTM-UHFFFAOYSA-N 5-amino-2-chloro-4-methylphenol Chemical compound CC1=CC(Cl)=C(O)C=C1N ASWULCVCLWLUTM-UHFFFAOYSA-N 0.000 description 1
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 1
- QSTYUPADMXCCRV-UHFFFAOYSA-N 5-amino-2-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C(O)=C1 QSTYUPADMXCCRV-UHFFFAOYSA-N 0.000 description 1
- WDQMXRWYXILWPT-UHFFFAOYSA-N 5-amino-4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=C(N)C=C1O WDQMXRWYXILWPT-UHFFFAOYSA-N 0.000 description 1
- FSBRKZMSECKELY-UHFFFAOYSA-N 5-aminonaphthalen-2-ol Chemical compound OC1=CC=C2C(N)=CC=CC2=C1 FSBRKZMSECKELY-UHFFFAOYSA-N 0.000 description 1
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
- SERBLGFKBWPCJD-UHFFFAOYSA-N 6-aminonaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(N)=CC=C21 SERBLGFKBWPCJD-UHFFFAOYSA-N 0.000 description 1
- ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 1
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-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
- 239000004952 Polyamide Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical class OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Landscapes
- Coloring (AREA)
Description
【発明の詳細な説明】
本発明は一般的に云えば有機材料の着色方法に
関し、更に詳しく云えば、新規な染料による有機
材料、特にポリエステル系繊維等の如き疎水性合
成繊維の染色方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates generally to a method for coloring organic materials, and more particularly to a method for dyeing organic materials, particularly hydrophobic synthetic fibers such as polyester fibers, with novel dyes.
従来、ポリエステル系繊維の如き疎水性繊維を
染色するための染料は種々開発され、且つ広く使
用されているが、このような染料は、疎水性の繊
維を染色するものであるため、その分子量は比較
的低いものであり、且つ結晶性も低いものであ
る。そのために、必然的に染色布の耐昇華性が低
く、染色布の種々の熱処理時に種々の問題が生じ
る。又、同様な理由で、染色後染料が繊維の表面
に移行し易く、乾及び湿時の摩擦堅牢度や耐光性
が不十分である。 Conventionally, various dyes for dyeing hydrophobic fibers such as polyester fibers have been developed and are widely used, but since these dyes dye hydrophobic fibers, their molecular weight is It has a relatively low crystallinity. Therefore, the sublimation resistance of the dyed fabric is inevitably low, and various problems occur during various heat treatments of the dyed fabric. Furthermore, for the same reason, the dye tends to migrate to the surface of the fiber after dyeing, resulting in insufficient dry and wet rubbing fastness and light resistance.
このような欠点を解決する一つの考え方とし
て、分子量が高く、且つ結晶性の良好な、すなわ
ち熱に対して安定な染料を使用するという方法が
考えられるが、この場合は染料の染色性や染色速
度が激減するという新たな問題が生じる。 One way to solve these drawbacks is to use a dye that has a high molecular weight and good crystallinity, that is, is stable against heat. A new problem arises: the speed is drastically reduced.
本発明者は上述の如き従来技術の欠点を解決す
べく鋭意研究の結果、染料の化学構造中に、ある
特定の構造を組込むことにより、分子量が比較的
高く、且つ結晶性の良好な染料でも良好な染色性
を有することを知見して本発明を完成した。 As a result of intensive research to solve the above-mentioned drawbacks of the prior art, the present inventor has found that by incorporating a certain structure into the chemical structure of the dye, even dyes with relatively high molecular weight and good crystallinity can be produced. The present invention was completed based on the finding that it has good dyeability.
すなわち、本発明は、下記一般式(1)で表わされ
る染料を使用することを特徴とする有機材料の着
色方法である。 That is, the present invention is a method for coloring an organic material, which is characterized by using a dye represented by the following general formula (1).
但し、式中のR1は、水酸基を有するベンゼン
環又はナフタレン環である。 However, R 1 in the formula is a benzene ring or naphthalene ring having a hydroxyl group.
本発明を詳細に説明すると、上記下記一般式(1)
で表わされる染料は、３・３−ジメトキシ−４・
５・６・７−テトラクロルイソインドリン−１−
オン、３−イミノ−４・５・６・７−テトラクロ
ルイソインドリン−１−オン又は３・３・４・
５・６・７−ヘキサクロロイソインドリン−１−
オン（以下単に中間体Ａという）と、水酸基を有
している芳香族アミン（以下単に中間体Ｂとい
う）とを約１：１のモル比で反応させて得られる
ものであり、その反応方法は従来公知の方法に準
じて行うことができる。 To explain the present invention in detail, the following general formula (1)
The dye represented by 3,3-dimethoxy-4,
5,6,7-tetrachloroisoindoline-1-
one, 3-imino-4,5,6,7-tetrachloroisoindolin-1-one or 3,3,4,
5,6,7-hexachloroisoindoline-1-
(hereinafter simply referred to as intermediate A) and an aromatic amine having a hydroxyl group (hereinafter simply referred to as intermediate B) in a molar ratio of approximately 1:1. can be carried out according to conventionally known methods.
上記方法における中間体はいずれも公知である
が、それらの組合せからなる前記一般式(1)で表わ
される染料は新規である。 All of the intermediates in the above method are known, but the dye represented by the general formula (1) consisting of a combination thereof is new.
上記の中間体Ｂは、アミノフエノール類又はア
ミノナフトール類であり、公知のものはいずれも
使用でき、代表例を挙げれば、例えば、
Ｏ−アミノフエノール
ｍ−アミノフエノール、
ｐ−アミノフエノール；
３−、４−、５−又は６−アミノ−ｏ−クレゾ
ール、
２−、４−又は６−アミノ−ｍ−クレゾール；
２−又は３−アミノ−ｐ−クレゾール；
アミノヒドロキノン；
２−アミノチモール；
５−又は６−アミノ−ｏ−３−キシレノール、
３−又は５−アミノ−ｏ−４−キシレノール、
５−アミノ−ｍ−２−キシレノール、
５−又は６−アミノ−ｍ−４−キシレノール、
４−アミノ−ｍ−５−キシレノール、
３−、５−又は６−アミノ−ｐ−２−キシレノ
ール；
２−、４−、５−、６−、７−又は８−アミノ
−１−ナフトール、
１−、３−、４−、５−、６−、７−又は８−
アミノ−２−ナフトール；
４−、５−又は６−クロロ−３−アミノ−ｏ−
クレゾール、
３−又は４−クロロ−５−アミノ−ｏ−クレゾ
ール、
６−クロロ−４−アミノ−ｍ−クレゾール、
２−又は４−クロロ−６−アミノ−ｍ−クレゾ
ール、
５−又は６−クロロ−３−アミノ−ｐ−クレゾ
ール、
３−、４−又は５−クロロ−２−アミノフエノ
ール、
２−又は４−クロロ−３−アミノフエノール、
２−又は３−クロロ−４−アミノフエノール；
４−ヒドロキシ−３−アミノアセトフエノン；
２−、４−又は５−ヒドロキシ−２−アミノジ
フエニル、
２−又は６−ヒドロキシ−３−アミノジフエニ
ル、
2′−又は4′−ヒドロキシ−４−アミノジフエニ
ル、
4′−ヒドロキシ−２−アミノジフエニルアミ
ン、
4′−ヒドロキシ−４−アミノジフエニルアミ
ン；
３−、４−、５−又は６−ヨード−ｏ−アミノ
フエノール、
５−ヨード−ｍ−アミノフエノール、
２−又は３−ヨード−ｐ−アミノフエノール；
３−、４−、５−又は６−ニトロ−ｏ−アミノ
フエノール、
４−、５−又は６−ニトロ−ｍ−アミノフエノ
ール、
２−又は３−ニトロ−ｐ−アミノフエノール、
４−ニトロ−ｏ−アミノフエノール等を使用す
ることができる。 The above-mentioned intermediate B is aminophenols or aminonaphthols, and any known ones can be used. Typical examples include: O-aminophenol, m-aminophenol, p-aminophenol; 3- , 4-, 5- or 6-amino-o-cresol, 2-, 4- or 6-amino-m-cresol; 2- or 3-amino-p-cresol; aminohydroquinone; 2-aminothymol; 5- or 6-amino-o-3-xylenol, 3- or 5-amino-o-4-xylenol, 5-amino-m-2-xylenol, 5- or 6-amino-m-4-xylenol, 4-amino -m-5-xylenol, 3-, 5- or 6-amino-p-2-xylenol; 2-, 4-, 5-, 6-, 7- or 8-amino-1-naphthol, 1-, 3 -, 4-, 5-, 6-, 7- or 8-
Amino-2-naphthol; 4-, 5- or 6-chloro-3-amino-o-
Cresol, 3- or 4-chloro-5-amino-o-cresol, 6-chloro-4-amino-m-cresol, 2- or 4-chloro-6-amino-m-cresol, 5- or 6-chloro -3-amino-p-cresol, 3-, 4- or 5-chloro-2-aminophenol, 2- or 4-chloro-3-aminophenol, 2- or 3-chloro-4-aminophenol; Hydroxy-3-aminoacetophenone; 2-, 4- or 5-hydroxy-2-aminodiphenyl, 2- or 6-hydroxy-3-aminodiphenyl, 2'- or 4'-hydroxy-4-aminodiphenyl, 4'- Hydroxy-2-aminodiphenylamine, 4'-hydroxy-4-aminodiphenylamine; 3-, 4-, 5- or 6-iodo-o-aminophenol, 5-iodo-m-aminophenol, 2- or 3-iodo-p-aminophenol; 3-, 4-, 5- or 6-nitro-o-aminophenol, 4-, 5- or 6-nitro-m-aminophenol, 2- or 3-nitro- p-aminophenol, 4-nitro-o-aminophenol, etc. can be used.
本発明方法に従つて合成繊維、例えば、ポリエ
ステル系繊維、セルロースエステル系繊維、その
他合成繊維材料を染色するには、前記一般式(1)で
表わされる染料の単独又は２種以上を混合して、
常法により水性媒質中に分散させた染色浴、或い
は捺染糊を調製し、それ自体公知の方法で浸染又
は捺染を行う。 In order to dye synthetic fibers such as polyester fibers, cellulose ester fibers, and other synthetic fiber materials according to the method of the present invention, dyes represented by the general formula (1) may be used alone or in combination of two or more. ,
A dyeing bath or printing paste dispersed in an aqueous medium is prepared in a conventional manner, and dyeing or printing is carried out in a manner known per se.
しかして、この染色浴又は捺染糊を調製するに
当つては、分散剤として、例えば、ナフタリンス
ルホン酸とホルムアルデヒドとの縮合物、オキシ
ナフタリンスルホン酸とクレゾールとホルムアル
デヒドとの縮合物、高級アルコールの硫酸エステ
ル又は高級アルキルベンゼンスルホン酸塩等が使
用される。又、必要に応じてキヤリヤーが使用さ
れる。キヤリヤーとしては、例えば、フエニルフ
エノール類、クロルベンゼン類、ヒドロキシ安息
酸エステル類、ベンゼンジカルボン酸エステル
類、フエニルメチルカルビトール類、低級アルキ
ルナフタリン類等が挙げられる。 Therefore, in preparing this dyeing bath or printing paste, as a dispersant, for example, a condensate of naphthalene sulfonic acid and formaldehyde, a condensate of oxynaphthalene sulfonic acid, cresol, and formaldehyde, a sulfuric acid of higher alcohol, etc. Esters or higher alkylbenzene sulfonates are used. Also, a carrier is used if necessary. Examples of the carrier include phenylphenols, chlorobenzenes, hydroxybenzoates, benzenedicarboxylates, phenylmethyl carbitols, and lower alkylnaphthalenes.
かくして、例えば、浸洗の場合、所要の染色濃
度に応じた前記一般式(1)で表わされる染料を微細
に分散させた染色浴を仕立て、高温染色を行う場
合は、120乃至130℃の間で60乃至120分間染色を
行つた後、常法によりソーピングを行う。この場
合染浴には特にキヤリヤーを必要としない。 Thus, for example, in the case of immersion washing, a dyeing bath in which the dye represented by the general formula (1) is finely dispersed is prepared according to the required dyeing concentration, and in the case of high-temperature dyeing, the dyeing bath is prepared at a temperature between 120 and 130°C. After staining for 60 to 120 minutes, soaping is performed in a conventional manner. In this case, no particular carrier is required for the dyebath.
又、キヤリヤー染色を行う場合は、染浴に前記
キヤリヤーを適宜量添加した染浴を仕立て、80乃
至100℃の間で60乃至120分間染色を行つた後、常
法によりソーピング処理を行う。 When carrier dyeing is carried out, a suitable amount of the above-mentioned carrier is added to the dye bath to prepare a dye bath, dyeing is carried out at 80 to 100° C. for 60 to 120 minutes, and then soaping treatment is carried out by a conventional method.
本発明方法が適用される合成繊維としては、例
えば、ポリエステル系繊維、ポリエステルエーテ
ル繊維アセテート繊維、トリアセテート繊維等の
セルロースエステル系繊維、更にポリアミド系繊
維等が挙げられるが、これらの繊維又はこれらの
繊維と他種の繊維とを混紡又は混織した繊維製品
にも本発明方法を適用することができる。 Examples of synthetic fibers to which the method of the present invention is applied include cellulose ester fibers such as polyester fibers, polyester ether fibers, acetate fibers, and triacetate fibers, as well as polyamide fibers. The method of the present invention can also be applied to textile products made by blending or blending fibers with other types of fibers.
本発明の方法によれば、上記合成繊維を耐光
性、耐昇華性及びその他の堅牢性に優れた鮮明な
色調に染色することができ、特にポリエステル系
繊維においては、耐光性及び耐昇華性が良好な染
色物を得ることができる。しかも本発明の染料は
高温染色及びキヤリヤー染色の何れにおいても優
れた染着性を示すので工業的に極めて有利であ
る。 According to the method of the present invention, the synthetic fibers described above can be dyed into vivid colors with excellent light fastness, sublimation resistance, and other fastness properties. In particular, polyester fibers have excellent light fastness and sublimation resistance. A good dyed product can be obtained. Moreover, the dye of the present invention exhibits excellent dyeing properties in both high-temperature dyeing and carrier dyeing, and is therefore extremely advantageous industrially.
上記本発明において使用する染料は比較的高い
分子量と結晶性を有するのにも係らず、上記の如
き優れた染色性を有するのは驚くべきことであ
る。 Although the dye used in the present invention has a relatively high molecular weight and crystallinity, it is surprising that it has the above-mentioned excellent dyeing properties.
本発明方法における染料は上述の如き疎水性繊
維だけではなく、他の各種の有機材料、例えば、
合成樹脂、合成塗料、印刷インキ等の着色にも有
用であり、それぞれの分野での常法に従つて有機
材料を着色すれば、優れた鮮明性、透明性、耐光
性等の着色物を得ることができる。 The dye used in the method of the present invention is not limited to the above-mentioned hydrophobic fibers, but also various other organic materials, such as
It is also useful for coloring synthetic resins, synthetic paints, printing inks, etc. If organic materials are colored according to the conventional methods in each field, colored products with excellent clarity, transparency, and light resistance can be obtained. be able to.
次に本発明方法の詳細を以下の実施例により更
に具体的に説明する。 Next, the details of the method of the present invention will be explained more specifically with reference to the following examples.
尚、実施例中、部又は％とあるのは重量基準で
ある。 In the examples, parts or % are based on weight.
実施例 １
下記構造式の染料１部を
オキシナフタリンスルホン酸とクレゾールのホル
ムアルデヒドとの縮合物２部及びナフタリンスル
ホン酸とホルムアルデヒドとの縮合物２部を含む
水3000部中に微細に分散させ、この浴にポリエス
テル系繊維100部を浸漬し130℃で60分間処理す
る。処理後水洗し、高級アルコール硫酸エステル
４部を含む水3000部中で90℃で20分間ソーピング
処理し、ついで水洗、乾燥することにより耐光性
及び耐昇華性に優れた濃色の鮮明な黄色の染色物
が得られた。この染色物の最大吸収波長は385n
ｍであつた。Example 1 One part of the dye of the following structural formula was Finely dispersed in 3,000 parts of water containing 2 parts of a condensate of oxynaphthalene sulfonic acid and cresol with formaldehyde and 2 parts of a condensate of naphthalene sulfonic acid and formaldehyde, 100 parts of polyester fibers were immersed in this bath. Process for 60 min at °C. After treatment, it is washed with water, soaped in 3000 parts of water containing 4 parts of higher alcohol sulfate ester at 90℃ for 20 minutes, then washed with water and dried to produce a deep, vivid yellow color with excellent light resistance and sublimation resistance. A dyed product was obtained. The maximum absorption wavelength of this dye is 385n
It was m.
耐光堅牢度（JIS、L.1044（1959））
フエードメーター ６乃至７級
昇華堅牢度（180℃×30秒）
アイロンテスター ３乃至４級
尚、上記の染料は、３−イミノ−４・５・６・
７−テトラクロルイソインドリン−１−オン28.4
部と２−アミノ−４−ニトロフエノール15.4部と
を284部のブチルセロソルブ中に加え、155乃至
160℃で３時間反応を行い、放冷後、生成した黄
色結晶を濾別し、メタノールで洗浄し、更に水洗
し、乾燥して得られたものである（収量40部）。Light fastness (JIS, L.1044 (1959)) Fade meter 6th to 7th grade Sublimation fastness (180℃ x 30 seconds) Iron tester 3rd to 4th grade The above dyes are 3-imino-4.5・６・
7-Tetrachloroisoindolin-1-one 28.4
and 15.4 parts of 2-amino-4-nitrophenol were added to 284 parts of butyl cellosolve, and 155 to 15.4 parts of butyl cellosolve were added.
The reaction was carried out at 160°C for 3 hours, and after cooling, the yellow crystals formed were filtered off, washed with methanol, further washed with water, and dried (yield: 40 parts).
実施例 ２
下記構造式の染料１部を
ナフタリンスルホン酸とホルムアルデヒドとの縮
合物３部及び高級アルコール硫酸エステル４部を
含む水3000部中に分散させ、この浴にポリエステ
ル繊維100部を浸漬し、100℃で90分処理する。Example 2 One part of the dye of the following structural formula was It is dispersed in 3,000 parts of water containing 3 parts of a condensate of naphthalene sulfonic acid and formaldehyde and 4 parts of higher alcohol sulfate, and 100 parts of polyester fibers are immersed in this bath and treated at 100°C for 90 minutes.
処理後実施例１と同様にソーピング処理するこ
とによつて堅牢な濃色の黄色の染色物が得られ
た。この染色物の最大吸収波長は396nｍであつ
た。 After treatment, soaping treatment was carried out in the same manner as in Example 1 to obtain a strong, deep yellow dyed product. The maximum absorption wavelength of this dyed material was 396 nm.
耐光堅牢度 ６乃至７級
耐昇華堅牢度 ４級
尚、上記の染料は、３・3′・４・５・６・７−
ヘキサクロルイソインドリン−１−オン34.0部と
２−アミノ−４−メチルフエノール12.3部とを
340部のオルソジクロルベンゼン中に加え、120乃
至125℃で５時間撹拌し、反応させると赤黄色の
結晶が析出する。この反応混合物を室温まで冷却
し、生成物を濾別し、メタノールと水で洗浄し、
乾燥して得られたものである（収量38.5部）。Light fastness: 6 to 7 class Sublimation fastness: 4 class In addition, the above dyes are 3, 3', 4, 5, 6, 7-
34.0 parts of hexachloroisoindolin-1-one and 12.3 parts of 2-amino-4-methylphenol.
The mixture was added to 340 parts of orthodichlorobenzene, stirred at 120 to 125°C for 5 hours, and reacted to precipitate red-yellow crystals. The reaction mixture was cooled to room temperature, the product was filtered off, washed with methanol and water,
It was obtained by drying (yield: 38.5 parts).
実施例 ３
下記構造の染料１部を
オキシナフタリンスルホン酸とクレゾールとホル
ムアルデヒドとの縮合物２部及びナフタリンスル
ホン酸とホルムアルデヒドとの縮合物３部とを含
む水3000部中に分散させ、この浴にトリクロルベ
ンゼン３部を添加後ポリエステル繊維100部を浸
漬し、100℃で90分処理する。処理後水洗し、実
施例１と同様にソーピング処理することにより堅
牢な濃褐色の染色物が得られた。この染色物の最
大吸収波長は410nｍであつた。Example 3 One part of the dye with the following structure After dispersing 2 parts of a condensate of oxynaphthalene sulfonic acid, cresol, and formaldehyde in 3000 parts of water containing 3 parts of a condensation product of naphthalene sulfonic acid and formaldehyde, and adding 3 parts of trichlorobenzene to this bath, 100 parts of polyester fiber was obtained. Soak the parts and treat at 100℃ for 90 minutes. After the treatment, the dyed product was washed with water and subjected to soaping treatment in the same manner as in Example 1 to obtain a strong dark brown dyed product. The maximum absorption wavelength of this dyed material was 410 nm.
耐堅牢度 ６乃至７級
耐華堅牢度 ４乃至５級
尚、上記の染料は、３−イミノ−４・５・６・
７−テトラクロルイソインドリン−１−オン28.4
部と１−アミノ−５−ナフトール15.9部とを426
部の氷酢酸中に加え、撹拌しながら昇温し、110
乃至115℃で２時間反応させた後冷却し、生成物
を湧別し、メタノール及び水で洗浄し、乾燥して
得たものである（収量40部）。Colorfastness: 6th to 7th class Colorfastness: 4th to 5th class The above dyes are 3-imino-4, 5, 6,
7-Tetrachloroisoindolin-1-one 28.4
426 parts and 15.9 parts of 1-amino-5-naphthol.
of glacial acetic acid, and heated to 110% while stirring.
After reacting for 2 hours at 115°C to 115°C, the product was cooled, separated by distillation, washed with methanol and water, and dried (yield: 40 parts).
実施例 ４乃至26
下記第１表の中間体Ａ及び中間体Ｂを使用し、
実施例１乃至３と同様にして得た各種の染料を使
用し、ポリエステル繊維を使用したところ、下記
第１表の結果を得た。Examples 4 to 26 Using Intermediate A and Intermediate B in Table 1 below,
When various dyes obtained in the same manner as in Examples 1 to 3 were used and polyester fibers were used, the results shown in Table 1 below were obtained.
第１表
実施例 ４
中間体Ａ ３−イミノ−４・５・６・７−テトラ
クロルイソインドリン−１−オン
中間体Ｂ ｏ−アミノフエノール
繊維上の色調 黄 色
最大吸収波長 390nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 ５
中間体Ａ ３−イミノ−４・５・６・７−テトラ
クロルイソインドリン−１−オン
中間体Ｂ ｍ−アミノフエノール
繊維上の色調 黄 色
最大吸収波長 380nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 ６
中間体Ａ ３−イミノ−４・５・６・７−テトラ
クロルイソインドリン−１−オン
中間体Ｂ ｐ−アミノフエノール
繊維上の色調 黄 色
最大吸収波長 395nｍ
耐光性 ７乃至８
耐昇華性 ４乃至５
実施例 ７
中間体Ａ ３−イミノ−４・５・６・７−テトラ
クロルイソインドリン−１−オン
中間体Ｂ ８−アミノ−２−ナフトール
繊維上の色調 黄 色
最大吸収波長 405nｍ
耐光性 ５乃至６
耐昇華性 ４乃至５
実施例 ８
中間体Ａ ３−イミノ−４・５・６・７−テトラ
クロルイソインドリン−１−オン
中間体Ｂ １−アミノ−５−ナフトール
繊維上の色調 褐 色
最大吸収波長 412nｍ
耐光性 ５乃至６
耐昇華性 ４乃至５
実施例 ９
中間体Ａ ３−イミノ−４・５・６・７−テトラ
クロルイソインドリン−１−オン
中間体Ｂ ４−アミノ−１−ナフトール
繊維上の色調 褐黄色
最大吸収波長 390nｍ
耐光性 ５乃至６
耐昇華性 ４乃至５
実施例 10
中間体Ａ ３−イミノ−４・５・６・７−テトラ
クロルイソインドリン−１−オン
中間体Ｂ ３−アミノ−ｏ−クレゾール
繊維上の色調 黄 色
最大吸収波長 397nｍ
耐光性 ５乃至６
耐昇華性 ４乃至５
実施例 11
中間体Ａ ３−イミノ−４・５・６・７−テトラ
クロルイソインドリン−１−オン
中間体Ｂ アミノ−ｏ−クレゾール
繊維上の色調 黄 色
最大吸収波長 380nｍ
耐光性 ５乃至６
耐昇華性 ４乃至５
実施例 12
中間体Ａ ３・３・４・５・６・７−ヘキサクロ
ルイソインドリン−１−オン
中間体Ｂ アミノハイドロキノン
繊維上の色調 黄 色
最大吸収波長 385nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 13
中間体Ａ ３・３・４・５・６・７−ヘキサクロ
ルイソインドリン−１−オン
中間体Ｂ ２−アミノチモール
繊維上の色調 赤黄色
最大吸収波長 390nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 14
中間体Ａ ３・３・４・５・６・７−ヘキサクロ
ルイソインドリン−１−オン
中間体Ｂ ５−アミノ−ｏ−３−キシレノール
繊維上の色調 赤黄色
最大吸収波長 385nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 15
中間体Ａ ３・３・４・５・６・７−ヘキサクロ
ルイソインドリン−１−オン
中間体Ｂ ６−アミノ−ｏ−３−キシレノール
繊維上の色調 赤黄色
最大吸収波長 392nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 16
中間体Ａ ３・３・４・５・６・７−ヘキサクロ
ルイソインドリン−１−オン
中間体Ｂ ３−アミノ−ｏ−４−キシレノール
繊維上の色調 赤黄色
最大吸収波長 390nｍ
耐光性 ７
耐昇華性 ４乃至５
実施例 17
中間体Ａ ３・３・４・５・６・７−ヘキサクロ
ルイソインドリン−１−オン
中間体Ｂ ５−アミノ−ｏ−４−キシレノール
繊維上の色調 赤黄色
最大吸収波長 387nｍ
耐光性 ７
耐昇華性 ４乃至５
実施例 18
中間体Ａ ３・３・４・５・６・７−ヘキサクロ
ルイソインドリン−１−オン
中間体Ｂ ５−アミノ−ｍ−２−キシレノール
繊維上の色調 赤黄色
最大吸収波長 388nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 19
中間体Ａ ３・３・４・５・６・７−ヘキサクロ
ルイソインドリン−１−オン
中間体Ｂ ３−ヨードーｏ−アミノフエノール
繊維上の色調 黄 色
最大吸収波長 381nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 20
中間体Ａ ３・３・４・５・６・７−ヘキサクロ
ルイソインドリン−１−オン
中間体Ｂ ４−ヨード−ｏ−アミノフエノール
繊維上の色調 黄 色
最大吸収波長 380nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 21
中間体Ａ ３・３−ジメトキシ−４・５・６・７
−テトラクロルイソインドリン−１−オン
中間体Ｂ ５−ヨード−ｏ−アミノフエノール
繊維上の色調 黄 色
最大吸収波長 382nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 22
中間体Ａ ３・３−ジメトキシ−４・５・６・７
−テトラクロルイソインドリン−１−オン
中間体Ｂ ６−ヨード−ｏ−アミノフエノール
繊維上の色調 黄 色
最大吸収波長 385nｍ
耐光性 ６乃至７
耐昇華性 ４乃至５
実施例 23
中間体Ａ ３・３−ジメトキシ−４・５・６・７
−テトラクロルイソインドリン−１−オン
中間体Ｂ ３−ニトロ−ｏ−アミノフエノール
繊維上の色調 黄褐色
最大吸収波長 388nｍ
耐光性 ５乃至６
耐昇華性 ４乃至５
実施例 24
中間体Ａ ３・３−ジメトキシ−４・５・６・７
−テトラクロルイソインドリン−１−オン
中間体Ｂ ６−ニトロ−ｏ−アミノフエノール
最大吸収波長 393nｍ
繊維上の色調 黄褐色
耐光性 ５乃至６
耐昇華性 ４乃至５
実施例 25
中間体Ａ ３・３−ジメトキシ−４・５・６・７
−テトラクロルイソインドリン−１−オン
中間体Ｂ ２−アミノ−１−ナフトール
繊維上の色調 黄褐色
最大吸収波長 405nｍ
耐光性 ５乃至６
耐昇華性 ４乃至５
実施例 26
中間体Ａ ３・３−ジメトキシ−４・５・６・７
−テトラクロルイソインドリン−１−オン
中間体Ｂ ７−アミノ−２−ナフトール
繊維上の色調 黄褐色
最大吸収波長 400nｍ
耐光性 ５乃至６
耐昇華性 ４乃至５ Table 1 Example 4 Intermediate A 3-Imino-4,5,6,7-tetrachloroisoindolin-1-one Intermediate B o-aminophenol Color tone on fiber Yellow Maximum absorption wavelength 390 nm Light resistance 6 to 7 Sublimation resistance 4 to 5 Example 5 Intermediate A 3-imino-4,5,6,7-tetrachloroisoindolin-1-one Intermediate B m-aminophenol Color tone on fiber Yellow Maximum color absorption wavelength 380 nm Light resistance 6 to 7 Sublimation resistance 4 to 5 Example 6 Intermediate A 3-imino-4,5,6,7-tetrachloroisoindolin-1-one Intermediate B p-Aminophenol Color tone on fiber Yellow Maximum absorption wavelength 395 nm Light resistance 7-8 Sublimation resistance 4-5 Example 7 Intermediate A 3-imino-4,5,6,7-tetrachloroisoindolin-1-one Intermediate B 8-amino-2- Color tone on naphthol fiber Yellow Maximum absorption wavelength 405 nm Light resistance 5 to 6 Sublimation resistance 4 to 5 Example 8 Intermediate A 3-imino-4,5,6,7-tetrachloroisoindolin-1-one intermediate B Color tone on 1-amino-5-naphthol fiber Brown Color maximum absorption wavelength 412 nm Light resistance 5 to 6 Sublimation resistance 4 to 5 Example 9 Intermediate A 3-imino-4,5,6,7-tetrachloroiso Indolin-1-one intermediate B Color tone on 4-amino-1-naphthol fiber Brown-yellow maximum absorption wavelength 390 nm Light resistance 5 to 6 Sublimation resistance 4 to 5 Example 10 Intermediate A 3-imino-4.5. 6,7-Tetrachloroisoindolin-1-one Intermediate B Color tone on 3-amino-o-cresol fiber Yellow Maximum absorption wavelength 397 nm Light resistance 5 to 6 Sublimation resistance 4 to 5 Example 11 Intermediate A 3 -Imino-4,5,6,7-tetrachloroisoindolin-1-one intermediate B Color tone on amino-o-cresol fiber Yellow Maximum color absorption wavelength 380 nm Light resistance 5 to 6 Sublimation resistance 4 to 5 Examples 12 Intermediate A 3,3,4,5,6,7-hexachloroisoindolin-1-one Intermediate B Color tone on aminohydroquinone fiber Yellow Maximum color absorption wavelength 385 nm Light resistance 6 to 7 Sublimation resistance 4 to 5 Example 13 Intermediate A 3,3,4,5,6,7-hexachloroisoindolin-1-one Intermediate B 2-Aminothymol Color tone on fiber Red-yellow Maximum absorption wavelength 390 nm Light resistance 6 to 7 Sublimation resistance Properties 4 to 5 Example 14 Intermediate A 3,3,4,5,6,7-hexachloroisoindolin-1-one Intermediate B 5-amino-o-3-xylenol Color tone on fiber Red-yellow maximum absorption Wavelength 385 nm Light resistance 6 to 7 Sublimation resistance 4 to 5 Example 15 Intermediate A 3.3.4.5.6.7-hexachloroisoindolin-1-one Intermediate B 6-amino-o-3- Color tone on xylenol fiber Red yellow Maximum absorption wavelength 392 nm Light resistance 6 to 7 Sublimation resistance 4 to 5 Example 16 Intermediate A 3, 3, 4, 5, 6, 7-hexachloroisoindolin-1-one intermediate B Color tone on 3-amino-o-4-xylenol fiber Red yellow Maximum absorption wavelength 390 nm Light resistance 7 Sublimation resistance 4 to 5 Example 17 Intermediate A 3,3,4,5,6,7-hexachloroiso Indolin-1-one intermediate B 5-amino-o-4-xylenol Color tone on fiber Red yellow Maximum absorption wavelength 387 nm Light resistance 7 Sublimation resistance 4 to 5 Example 18 Intermediate A 3.3.4.5. 6,7-hexachloroisoindolin-1-one intermediate B 5-amino-m-2-xylenol Color tone on fiber Red-yellow Maximum absorption wavelength 388 nm Light resistance 6 to 7 Sublimation resistance 4 to 5 Example 19 Intermediate A 3,3,4,5,6,7-hexachloroisoindolin-1-one intermediate B 3-Iodo-o-aminophenol Color tone on fiber Yellow Maximum color absorption wavelength 381 nm Light resistance 6 to 7 Sublimation resistance 4 to 5 Example 20 Intermediate A 3,3,4,5,6,7-hexachloroisoindolin-1-one Intermediate B 4-iodo-o-aminophenol Color tone on fiber Yellow Maximum color absorption wavelength 380 nm Light resistance Properties 6 to 7 Sublimation resistance 4 to 5 Example 21 Intermediate A 3,3-dimethoxy-4,5,6,7
-Tetrachloroisoindolin-1-one Intermediate B 5-Iodo-o-aminophenol Color tone on fiber Yellow Maximum color absorption wavelength 382 nm Light resistance 6 to 7 Sublimation resistance 4 to 5 Example 22 Intermediate A 3 and 3 -Dimethoxy-4, 5, 6, 7
-Tetrachloroisoindolin-1-one Intermediate B 6-iodo-o-aminophenol Color tone on fiber Yellow Maximum color absorption wavelength 385 nm Light resistance 6 to 7 Sublimation resistance 4 to 5 Example 23 Intermediate A 3 and 3 -Dimethoxy-4, 5, 6, 7
-Tetrachloroisoindolin-1-one Intermediate B 3-Nitro-o-aminophenol Color tone on fiber Yellow-brown maximum absorption wavelength 388 nm Light resistance 5 to 6 Sublimation resistance 4 to 5 Example 24 Intermediate A 3 and 3 -Dimethoxy-4, 5, 6, 7
-Tetrachloroisoindolin-1-one Intermediate B 6-nitro-o-aminophenol Maximum absorption wavelength 393 nm Color tone on fiber Yellow-brown light resistance 5 to 6 Sublimation resistance 4 to 5 Example 25 Intermediate A 3 and 3 -Dimethoxy-4, 5, 6, 7
-Tetrachloroisoindolin-1-one Intermediate B Color tone on 2-amino-1-naphthol fiber Yellow-brown maximum absorption wavelength 405 nm Light resistance 5 to 6 Sublimation resistance 4 to 5 Example 26 Intermediate A 3.3- Dimethoxy-4, 5, 6, 7
-Tetrachloroisoindolin-1-one intermediate B Color tone on 7-amino-2-naphthol fiber Yellow-brown maximum absorption wavelength 400 nm Light resistance 5 to 6 Sublimation resistance 4 to 5
Claims (1)
とを特徴とする有機材料の着色方法。 （但し、式中のR1は、水酸基を有するベンゼン環
又はナフタレン環である。）[Scope of Claims] 1. A method for coloring organic materials, characterized by using a dye represented by the following general formula (1). (However, R 1 in the formula is a benzene ring or naphthalene ring having a hydroxyl group.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56008992A JPS57123264A (en) | 1981-01-26 | 1981-01-26 | Coloring method of organic material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56008992A JPS57123264A (en) | 1981-01-26 | 1981-01-26 | Coloring method of organic material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57123264A JPS57123264A (en) | 1982-07-31 |
| JPS6247461B2 true JPS6247461B2 (en) | 1987-10-08 |
Family
ID=11708178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56008992A Granted JPS57123264A (en) | 1981-01-26 | 1981-01-26 | Coloring method of organic material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57123264A (en) |
-
1981
- 1981-01-26 JP JP56008992A patent/JPS57123264A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57123264A (en) | 1982-07-31 |
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