JPH0316983B2 - - Google Patents
Info
- Publication number
- JPH0316983B2 JPH0316983B2 JP7936083A JP7936083A JPH0316983B2 JP H0316983 B2 JPH0316983 B2 JP H0316983B2 JP 7936083 A JP7936083 A JP 7936083A JP 7936083 A JP7936083 A JP 7936083A JP H0316983 B2 JPH0316983 B2 JP H0316983B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- alkoxy
- hydrogen atom
- same meaning
- 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
- -1 monoazo compound Chemical class 0.000 claims description 63
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000000835 fiber Substances 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 238000004043 dyeing Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 230000002209 hydrophobic effect Effects 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 239000004744 fabric Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 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 3
- 238000003756 stirring Methods 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- AZRKRYOJEUTHER-UHFFFAOYSA-N 2-amino-5-formyl-4-methylthiophene-3-carbonitrile Chemical compound CC1=C(C=O)SC(N)=C1C#N AZRKRYOJEUTHER-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
- 229920002907 Guar gum Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 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
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- DJACTCNGCHPGOI-UHFFFAOYSA-N butyl 2-cyanoacetate Chemical compound CCCCOC(=O)CC#N DJACTCNGCHPGOI-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920006239 diacetate fiber Polymers 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 1
- FPUKYOSOAAPHTN-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1 FPUKYOSOAAPHTN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
Landscapes
- Coloring (AREA)
Description
本発明は疎水性繊維特にポリエステル繊維に良
好な染着性を示すモノアゾ化合物に関する。更に
詳しくは式（）
〔式（）においてＫは
The present invention relates to a monoazo compound that exhibits good dyeability on hydrophobic fibers, particularly polyester fibers. For more details, please refer to the expression () [In formula (), K is
【式】基
（但しＷは水素原子、クロル原子、ブロム原子、
C1〜4のアルキル基、C1〜4のアルコキシ基、又は
C2〜7のアルコキシアルコキシ基を、Ｖは水素原
子、クロル原子、ブロム原子、C1〜3のアルキル
基、C1〜3のアルコキシ基、水酸基、又は−
NHCOR3基（但しR3は水素原子、C1〜6のアルキ
ル基又はフエニル基を表わす。）を、R1，R2は
各々独立に水素原子、アリル基、アリール基、シ
クロヘキシル基、アラルキル基、C1〜6のアルキル
基、[Formula] Group (where W is a hydrogen atom, a chlorine atom, a bromine atom,
C 1-4 alkyl group, C 1-4 alkoxy group, or
A C 2-7 alkoxyalkoxy group, V is a hydrogen atom, a chlorine atom, a bromine atom, a C 1-3 alkyl group, a C 1-3 alkoxy group, a hydroxyl group, or -
NHCOR 3 group (wherein R 3 represents a hydrogen atom, a C 1-6 alkyl group, or a phenyl group), R 1 and R 2 are each independently a hydrogen atom, an allyl group, an aryl group, a cyclohexyl group, an aralkyl group. , C 1-6 alkyl group,
【式】基（但しR4はC1〜4のア
ルキル基又はアリル基を表わす。）又は水酸基、
C1〜4のアルコキシ基、C2〜7のアルコキシアルコキ
シ基、アリールオキシ基、アリルオキシ基、シア
ノ基、C1〜3のアルカノイルオキシ基、アリーロイ
ルオキシ基、（C1〜4−アルコキシ）カルボニル基、
（C2〜7−アルコキシアルコキシ）カルボニル基、
アラルキルオキシカルボニル基、（C1〜6−アルコ
キシ）カルボニルオキシ基、シクロヘキシルオキ
シ基又はハロゲン原子により置換されたC1〜6のア
ルキル基を表わす。）；[Formula] group (wherein R 4 represents a C 1-4 alkyl group or allyl group) or a hydroxyl group,
C1-4 alkoxy group, C2-7 alkoxyalkoxy group, aryloxy group, allyloxy group, cyano group, C1-3 alkanoyloxy group, aryloyloxy group, ( C1-4 -alkoxy)carbonyl basis,
( C2-7 -alkoxyalkoxy)carbonyl group,
It represents an aralkyloxycarbonyl group, a ( C1-6 -alkoxy)carbonyloxy group, a cyclohexyloxy group, or a C1-6 alkyl group substituted with a halogen atom. );
【式】基
（但しR5は水素原子、C1〜3のアルキル基又は−
NHCOR3基（但しR3は前記と同じ意味を表わ
す。）を、R6、R7及びR8は水素原子又はメチル基
を表わし、R1は前記と同じ意味を表わす。）；
[Formula] Group (where R 5 is a hydrogen atom, a C 1-3 alkyl group, or -
NHCOR 3 group (R 3 has the same meaning as above), R 6 , R 7 and R 8 each represent a hydrogen atom or a methyl group, and R 1 has the same meaning as above. );
【式】基（但しR1，R2は前記と同 じ意味を表わす。）；[Formula] Group (however, R 1 and R 2 have the same meanings as above);
【式】基（但し
R1，R2及びR6は前記と同じ意味を表わす。）を表
わし、Ｘはニトロ基、シアノ基、（C1〜4−アルコ
キシ）カルボニル基、−CONHR3基（但しR3は前
記と同じ意味を表わす。）又は−COR3基（但し
R3は前記と同じ意味を表わす。）を、Ｙは水素原
子、C1〜4のアルキル基又はフエニル基を、Ｒはシ
アノ基、（C1〜6−アルコキシ）カルボニル基、
（C2〜9−アルコキシアルコキシ）カルボニル基、
（C3〜4−アルケニルオキシ）カルボニル基、−
CONHR3基（但しR3は前記と同じ意味を表わ
す。）又は−COR3基（但しR3は前記と同じ意味
を表わす。）を表わす。〕
で表わされる水不溶性モノアゾ化合物及びこれを
単独で又は２種以上混合して用いることを特徴と
する疎水性繊維の染色又は捺染法に関する。
本発明のモノアゾ化合物は以下のようにして合
成される。
まず式（）
（式（）において、Ｒ，Ｘ，及びＹは前記と
同じ意味を表わす。）で示されるアミン類を公知
の方法でジアゾ化して得たジアゾニウム塩を式
（）Ｈ−Ｋ （）
（式（）においてＫは前記と同じ意味を表わ
す。）で示されるカツプリング成分と常法により
カツプリングすることによつて式（）の化合物
が得られる。
又次のように合成してもよい。
式（）
（式（）においてＸ及びＹは前記と同じ意味
を表わす。）で示されるアミン類を公知の方法で
ジアゾ化して得たジアゾニウム塩を式（）で示
されるカツプリング成分にカツプリングすること
によつて得られる式（）
のモノアゾ化合物に式（）
（式（）においてＲは前記と同じ意味を表わ
す。）で示される活性メチレン化合物を反応させ
て式（）で示されるモノアゾ化合物が得られ
る。
本発明において用いられるジアゾ成分（）
においてＲ，Ｘ及びＹの具体例は次の通りであ
る。
Ｒ：シアノ基；メトキシカルボニル基、エトキシ
カルボニル基、プロポキシカルボニル基、ブトキ
シカルボニル基、ペンチルオキシカルボニル基、
ヘキシルオキシカルボニル基のようなアルコキシ
カルボニル基；メトキシメトキシカルボニル基、
メトキシエトキシカルボニル基、メトキシプロポ
キシカルボニル基、エトキシエトキシカルボニル
基、ｎ−ブトキシエトキシカルボニル基、ヘキシ
ルオキシエトキシカルボニル基、ヘキシルオキシ
プロポキシカルボニル基、ヘキシルオキシメトキ
シカルボニル基等のアルコキシアルコキシカルボ
ニル基；アリロキシカルボニル基、２−ブテニル
オキシカルボニル基、２−メチルアリロキシカル
ボニル基のようなアルケニルオキシカルボニル
基；カルバモイル基、−CONHCH3基、−
CONHC2H5基、−CONHC4H9（ｎ）基、−
CONHC5H11基、−CONHC6H13基、
[Formula] represents a group (wherein R 1 , R 2 and R 6 have the same meanings as above), and X is a nitro group, a cyano group, a (C 1-4 -alkoxy)carbonyl group, -CONHR 3 group ( (However, R 3 has the same meaning as above.) or -COR 3 groups (However, R 3 has the same meaning as above.)
R 3 has the same meaning as above. ), Y is a hydrogen atom, a C 1-4 alkyl group or a phenyl group, R is a cyano group, a (C 1-6 -alkoxy) carbonyl group,
( C2-9 -alkoxyalkoxy)carbonyl group,
( C3-4 -alkenyloxy)carbonyl group, -
It represents 3 CONHR groups (where R 3 has the same meaning as above) or 3 -COR groups (where R 3 has the same meaning as above). ] The present invention relates to a water-insoluble monoazo compound represented by the following and a method for dyeing or printing hydrophobic fibers, which is characterized by using the water-insoluble monoazo compound either alone or in a mixture of two or more thereof. The monoazo compound of the present invention is synthesized as follows. First, the expression () (In formula (), R, ), K represents the same meaning as above.) A compound of formula () can be obtained by coupling with a coupling component represented by ) by a conventional method. Alternatively, it may be synthesized as follows. formula() (In formula (), X and Y represent the same meanings as above.) By coupling a diazonium salt obtained by diazotizing an amine represented by formula () by a known method to a coupling component represented by formula (). The resulting formula () For the monoazo compound of formula () (In formula (), R represents the same meaning as above.) A monoazo compound represented by formula () is obtained by reacting an active methylene compound represented by formula (). Diazo component () used in the present invention Specific examples of R, X and Y are as follows. R: cyano group; methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group,
Alkoxycarbonyl group such as hexyloxycarbonyl group; methoxymethoxycarbonyl group,
Alkoxyalkoxycarbonyl groups such as methoxyethoxycarbonyl group, methoxypropoxycarbonyl group, ethoxyethoxycarbonyl group, n-butoxyethoxycarbonyl group, hexyloxyethoxycarbonyl group, hexyloxypropoxycarbonyl group, hexyloxymethoxycarbonyl group; aryloxycarbonyl group , 2-butenyloxycarbonyl group, alkenyloxycarbonyl group such as 2-methylallyloxycarbonyl group; carbamoyl group, -CONHCH 3 group, -
CONHC 2 H 5 groups, -CONHC 4 H 9 (n) groups, -
CONHC 5 H 11 groups, -CONHC 6 H 13 groups,
【式】基等のＮ−置換又は非置換
のカルバモイル基；ホルミル基、アセチル基、プ
ロピオニル基、ブチリル基、ヘペタイル基等のア
シル基；[Formula] N-substituted or unsubstituted carbamoyl groups such as groups; acyl groups such as formyl groups, acetyl groups, propionyl groups, butyryl groups, hepetyl groups;
【式】基
Ｘ：ニトロ基；シアノ基；メトキシカルボニル
基、エトキシカルボニル基、ｎ−プロポキシカル
ボニル基、iso−プロポキシカルボニル基、ｎ−
ブトキシカルボニル基等のアルコキシカルボニル
基；カルバモイル基、−CONHCH3基、−
CONHC2H5基、−CONHC4H9（ｎ）基、−
CONHC5H11基、−CONHC6H13基、
[Formula] Group X: Nitro group; Cyano group; Methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, iso-propoxycarbonyl group, n-
Alkoxycarbonyl group such as butoxycarbonyl group; carbamoyl group, -CONHCH 3 group, -
CONHC 2 H 5 groups, -CONHC 4 H 9 (n) groups, -
CONHC 5 H 11 groups, -CONHC 6 H 13 groups,
【式】基等の置換又は非置換のカ
ルバモイル基；ホルミル基、アセチル基、プロピ
オニル基、ブチリル基、ヘプタイル基等のアシル
基；[Formula] substituted or unsubstituted carbamoyl group such as a group; acyl group such as formyl group, acetyl group, propionyl group, butyryl group, heptyl group;
【式】基
Ｙ：水素原子；メチル基、エチル基、ｎ−プロピ
ル基、iso−プロピル基、ｎ−ブチル基等のアル
キル基；フエニル基
又カツプリング成分として用いられる式（ａ
〜ｄ）の化合物
においてＶ，Ｗ，R1，R2，R5，R6，R7，及びR8
の具体例は次の通りである。
Ｖ：水素原子；クロル原子、ブロム原子；メチル
基、エチル基、ｎ−プロピル基等のアルキル基；
メトキシ基、エトキシ基、ブトキシ基、ｎ−プロ
ポキシ基等のアルコキシ基；水酸基；ホルミルア
ミノ基、アセチルアミノ基、プロピオニルアミノ
基、ブチリルアミノ基、ヘキサノイルアミノ基、
ヘペタノイルアミノ基、ベンゾイルアミノ基等の
アシルアミノ基
Ｗ：水素原子；クロル原子、ブロム原子；メチル
基、エチル基、ｎ−又はiso−プロピル基、ｎ−
ブチル基等のアルキル基；メトキシ基、エトキシ
基、プロポキシ基、ブトキシ基等のアルコキシ
基；β−メトキシエトキシ基、β−エトキシエト
キシ基、δ−メトキシブトキシ基、γ−メトキシ
プロポキシ基等のアルコキシアルコキシ基
R1，R2：水素原子；アリル基、フエニル基、ナ
フチル基等のアリール基；シクロヘキシル基；ベ
ンジル基、フエネチル基等のアラルキル基；メチ
ル基、エチル基、ｎ−又はiso−プロピル基、ブ
チル基、ペンチル基、ヘキシル基等のアルキル
基；[Formula] Group Y: Hydrogen atom; Alkyl group such as methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group; Phenyl group Formula (a
~d) Compound V, W, R 1 , R 2 , R 5 , R 6 , R 7 , and R 8
A specific example is as follows. V: hydrogen atom; chlorine atom, bromine atom; alkyl group such as methyl group, ethyl group, n-propyl group;
Alkoxy groups such as methoxy group, ethoxy group, butoxy group, n-propoxy group; hydroxyl group; formylamino group, acetylamino group, propionylamino group, butyrylamino group, hexanoylamino group,
Acylamino group such as hepetanoylamino group or benzoylamino group W: hydrogen atom; chlorine atom, bromine atom; methyl group, ethyl group, n- or iso-propyl group, n-
Alkyl groups such as butyl; alkoxy groups such as methoxy, ethoxy, propoxy, butoxy; alkoxyalkoxy such as β-methoxyethoxy, β-ethoxyethoxy, δ-methoxybutoxy, and γ-methoxypropoxy Groups R1 , R2 : hydrogen atom; aryl group such as allyl group, phenyl group, naphthyl group; cyclohexyl group; aralkyl group such as benzyl group, phenethyl group; methyl group, ethyl group, n- or iso-propyl group, Alkyl groups such as butyl group, pentyl group, hexyl group;
【式】【formula】
【式】【formula】
【式】【formula】
【式】ヒドロキ
シエチル基、メトキシエチル基、メトキシプロピ
ル基、エトキシエチル基、ｎ−ブトキシエチル
基、（β−メトキシ）エトキシエチル基、（β−エ
トキシ）エトキシエチル基、（γ−メトキシ）プ
ロポキシエチル基、フエノキシエチル基、アリル
オキシエチル基、シアノエチル基、アセチルオキ
シエチル基、プロプオニルオキシエチル基、ベン
ゾイルオキシエチル基、エトキシカルボニルメチ
ル基、メトキシカルボニルエチル基、エトキシカ
ルボニルエチル基、メトキシエトキシカルボニル
エチル基、エトキシエトキシカルボニルエチル
基、ベンジルオキシカルボニルエチル基、メトキ
シカルボニルオキシエチル基、エトキシカルボニ
ルオキシエチル基、シクロヘキシルオキシエチル
基、β−クロロエチル基、β−ブロムエチル基等
の置換アルキル基
R5：水素原子、メチル基、エチル基、ｎ−プロ
ピル基等のアルキル基；ホルミルアミノ基、アセ
チルアミノ基、プロピオニルアミノ基、ブチリル
アミノ基、ヘプタノイルアミノ基、ベンゾイルア
ミノ基、等のアシルアミノ基
R6：水素原子；メチル基
R7：水素原子；メチル基
R8：水素原子；メチル基
前記（）で表わされる化合物において特にす
ぐれた効果の得られるものは次の式（）
で表わされる化合物である。
式（）においてR′，R′1，R′2，X′，Y′，
V′及びW′は各々の次のものを表わす。
R′：−CN、−COOCH3、−COOC2H5、−
COOC4H9（ｎ）、−CONHCH3、−CONHC2H5、−
COCH3、−CONH2
X′：NO2、−CN、−COOCH3、
[Formula] Hydroxyethyl group, methoxyethyl group, methoxypropyl group, ethoxyethyl group, n-butoxyethyl group, (β-methoxy)ethoxyethyl group, (β-ethoxy)ethoxyethyl group, (γ-methoxy)propoxyethyl group group, phenoxyethyl group, allyloxyethyl group, cyanoethyl group, acetyloxyethyl group, proponyloxyethyl group, benzoyloxyethyl group, ethoxycarbonylmethyl group, methoxycarbonylethyl group, ethoxycarbonylethyl group, methoxyethoxycarbonylethyl group , ethoxyethoxycarbonylethyl group, benzyloxycarbonylethyl group, methoxycarbonyloxyethyl group, ethoxycarbonyloxyethyl group, cyclohexyloxyethyl group, β-chloroethyl group, β-bromoethyl group and other substituted alkyl groups R 5 : hydrogen atom, Alkyl group such as methyl group, ethyl group, n-propyl group; Acylamino group such as formylamino group, acetylamino group, propionylamino group, butyrylamino group, heptanoylamino group, benzoylamino group, etc. R 6 : Hydrogen atom; methyl Group R 7 : Hydrogen atom; Methyl group R 8 : Hydrogen atom; Methyl group Among the compounds represented by the above (), those having particularly excellent effects are those represented by the following formula () It is a compound represented by In equation (), R′, R′ 1 , R′ 2 , X′, Y′,
V' and W' represent each of the following: R′: −CN, −COOCH 3 , −COOC 2 H 5 , −
COOC 4 H 9 (n), -CONHCH 3 , -CONHC 2 H 5 , -
COCH 3 , −CONH 2 X′:NO 2 , −CN, −COOCH 3 ,
【式】、−COCH3 Y′：−Ｈ、−CH3、[Formula], -COCH 3 Y': -H, -CH 3 ,
【式】
V′：−Ｈ、−CH3、−NHCOCH3、
[Formula] V': -H, -CH 3 , -NHCOCH 3 ,
【式】
W′：−Ｈ、−Cl、−CH3、−OCH3、−C2H4OCH3
R′1，R′2：−Ｈ、−CH3、−C2H5、−C2H4OCH3、
−C2H4OC2H5、−C2H4CN、−C2H4OCH2CH＝
CH2、−C2H4OCOCH3、
[Formula] W′: −H, −Cl, −CH 3 , −OCH 3 , −C 2 H 4 OCH 3 R′ 1 , R′ 2 : −H, −CH 3 , −C 2 H 5 , −C 2H4OCH3 , _
−C 2 H 4 OC 2 H 5 , −C 2 H 4 CN, −C 2 H 4 OCH 2 CH=
CH 2 , −C 2 H 4 OCOCH 3 ,
【式】、−
C2H4OC2H4OC2H5、−C2H4COOCH3、−
C2H4COOC2H5、[Formula], − C 2 H 4 OC 2 H 4 OC 2 H 5 , − C 2 H 4 COOCH 3 , −
C 2 H 4 COOC 2 H 5 ,
【式】【formula】
【式】
本発明のモノアゾ化合物は疎水性繊維とりわけ
ポリエステル繊維の染色に適しておりその他ジア
セテート繊維、トリアセテート繊維、ポリアミド
繊維あるいはこれらと他の繊維との混合繊維の染
色又は捺染に供してすぐれた効果がえられる。
得られた染色物はいずれも青色〜緑色の色相を
呈し鮮明度にすぐれている。又湿潤堅牢度その他
の堅牢度が良好であつた。
本発明のモノアゾ染料を用いて疎水性繊維を染
色或いは、捺染を行うには前記式（）で示され
るモノアゾ化合物に、適当な分散剤例えばナフタ
レンスルホン酸のホリマリン縮合物或いはリグニ
ンスルホン酸等のアニオン分散剤、又はエチレン
オキサイドとプロピレンオキサイドのブロツク共
重合物、アルキルフエノールのエチレンオキサイ
ド付加物等のノニオン活性剤と少量の水を加えボ
ールミル或いは、サンドミル等を用いて充分に湿
式粉砕して、微細に分散したものが用いられる。
染色は高温染色、キヤリヤー染色、サーモゾル染
色、捺染等の公知の方法によつて行われる。
以下に、実施例を挙げて本発明を具体的に説明
する。実施例中、部及び％とあるのは夫々重量部
及び重量％を示すものとする。
実施例 １
式
で示される化合物4.5部を５℃以下に冷却した96
％硫酸12部にゆつくりと加える。この溶液に酢酸
５とプロピオン酸１の割合から成る混酸20部を10
℃以下で加える。つぎに、43％ニトロシル硫酸
6.3部を加えて、５℃以下で２時間撹拌し、ジア
ゾ化する。
Ｎ，Ｎ−ジエチル−ｍ−トルイジン3.2部とス
ルフアミン酸0.2部を含む10℃硫酸水溶液100部
に、先に得たジアゾ化液を滴下する。このカツプ
リング液に砕氷を加えて０℃以下に保持する。間
もなく暗青色の結晶が析出してくる。この反応液
を60℃で更に１時間かきまぜた後ロ過する。湯
洗、乾燥して次式で示される暗青色結晶5.8部を
得た。
このモノアゾ化合物のλmaxは75％アセトン水
溶液中で660nmであつた。このモノアゾ化合物の
構造はマススペクトル及び元素分析で確認した。
MASSスペクトルM+：394
元素分析
再結晶品（１，４−ジオキサンによる）の実測値
（％）
Ｃ Ｈ Ｎ
57.15 4.61 21.81
計算値（C19H18N6O2S）（％）
Ｃ Ｈ Ｎ
57.87 4.57 21.32
上記モノアゾ化合物15部をデモールＮ（花王ア
トラス製分散剤）40部とデモールＣ（花王アトラ
ス製分散剤）30部と共に水を加えてスラリーと
し、ボールミルを用いて湿式粉砕し、次いでスプ
レードライヤーで乾燥して分散化した染料を得
る。
この分散化した染料２部を水3000部に加えて分
散液とし、次いで酢酸と酢酸ソーダで染浴のPHを
５としテトロン布100部を浸潰し加圧下130℃とし
て、１時間染色する。次いで還元的にソーピング
し、次いで水洗する。明るい青色の染布が得られ
た。後加工を施した後の水堅牢度及びその他の堅
牢度が良好であつた。
実施例 ２〜30
実施例１と同様な方法で次表の化合物を製造し
ポリエステル布の染色を行つた。表中のＸ，Ｙ，
Ｗ，Ｖ，Ｒ，R1，R2は次式における置換基を意
味する。
[Formula] The monoazo compound of the present invention is suitable for dyeing hydrophobic fibers, especially polyester fibers, and is also excellent for dyeing or printing diacetate fibers, triacetate fibers, polyamide fibers, or mixed fibers with these and other fibers. You can get the effect. All of the obtained dyed products exhibit a blue to green hue and have excellent clarity. In addition, the wet fastness and other fastness properties were good. In order to dye or print hydrophobic fibers using the monoazo dye of the present invention, a suitable dispersant such as a polymarine condensate of naphthalenesulfonic acid or an anion such as ligninsulfonic acid is added to the monoazo compound represented by the above formula (). Add a dispersant or a nonionic activator such as a block copolymer of ethylene oxide and propylene oxide, or an ethylene oxide adduct of alkyl phenol, and a small amount of water, and thoroughly wet-pulverize using a ball mill or sand mill to make a fine powder. A dispersed version is used.
Dyeing is carried out by known methods such as high temperature dyeing, carrier dyeing, thermosol dyeing, and textile printing. The present invention will be specifically described below with reference to Examples. In the examples, parts and % indicate parts by weight and % by weight, respectively. Example 1 Formula 96 when 4.5 parts of the compound shown was cooled to below 5°C.
Slowly add to 12 parts of % sulfuric acid. Add 20 parts of a mixed acid consisting of 5 parts acetic acid and 1 part propionic acid to this solution.
Add at below ℃. Next, 43% nitrosyl sulfate
Add 6.3 parts and stir at below 5°C for 2 hours to diazotize. The previously obtained diazotized solution is added dropwise to 100 parts of a 10°C aqueous sulfuric acid solution containing 3.2 parts of N,N-diethyl-m-toluidine and 0.2 parts of sulfamic acid. Crushed ice is added to this coupling liquid to maintain the temperature below 0°C. Dark blue crystals will soon begin to precipitate. The reaction solution was stirred for an additional hour at 60°C and then filtered. After washing with hot water and drying, 5.8 parts of dark blue crystals represented by the following formula were obtained. The λmax of this monoazo compound was 660 nm in a 75% acetone aqueous solution. The structure of this monoazo compound was confirmed by mass spectrometry and elemental analysis. MASS spectrum M + : 394 Elemental analysis Actual value of recrystallized product (with 1,4-dioxane) (%) C H N 57.15 4.61 21.81 Calculated value (C 19 H 18 N 6 O 2 S) (%) C H N 57.87 4.57 21.32 15 parts of the above monoazo compound was mixed with 40 parts of Demol N (dispersant manufactured by Kao Atlas) and 30 parts of Demol C (dispersant manufactured by Kao Atlas) to form a slurry, wet-pulverized using a ball mill, and then sprayed. Dry with a dryer to obtain a dispersed dye. Two parts of the dispersed dye are added to 3000 parts of water to form a dispersion, and then the pH of the dye bath is adjusted to 5 with acetic acid and sodium acetate, and 100 parts of Tetron cloth is immersed and dyed at 130° C. under pressure for 1 hour. It is then reductively soaped and then washed with water. A bright blue dyed fabric was obtained. The water fastness and other fastness properties after post-processing were good. Examples 2 to 30 The compounds shown in the following table were produced in the same manner as in Example 1, and polyester cloth was dyed. X, Y, in the table
W, V, R, R 1 and R 2 mean substituents in the following formula.
【表】【table】
【表】
＼
CH３
CH３
／
29 〃 〃 〃 −NHCHO −COOCH２OC
２H５ −CH
〃 〃 665
＼
C２H５
30 〃 〃 〃 〃 −CONHCH３
−H
〃 645
実施例 31
２−アミノ−３−シアノ−４−メチル−５−ホ
ルミルチオフエン3.3部を５℃以下に冷却した96
％硫酸12.4部に徐々に加えて溶解させた。この溶
液に酢酸５、プロピオン酸１の割合から成る混酸
30部を10℃以下で加える。次いで43％ニトロシル
硫酸6.2部を加えて５℃以下で２時間撹拌しジア
ゾ化する。
３−（Ｎ，Ｎ−ジエチル）アミノ−アセトアニリ
ド4.1部とスルフアミン酸0.2部を含む10％硫酸水
溶液100部に先に得たジアゾ化液を滴下する。こ
の際、砕氷を適宜加えて反応液を０℃以下に保
つ。間もなく、暗青色の結晶が析出してくる。更
にこの反応液を60℃で１時間かきまぜた後、ロ過
する。湯洗、乾燥して次式で示される暗青色結晶
4.7を得た。
このモノアゾ化合物1.8部を１，４−ジオキサ
ン15部に加えて溶解させた。この溶液にシアノ酢
酸ブチルエステル1.5部ピペリジン0.1部及び酢酸
0.1部を加えて25〜30℃で１訊時間撹拌する。薄
層クロマトグラフイーにて反応の終了を確認し
て、メタノール15部を徐々に加えて結晶を析出さ
せる。結晶をロ取、水洗、乾燥して次式で示され
る暗青色の結晶2.5部を得た。
このモノアゾ化合物のλmaxは75％アセトン水
溶液中で635nmであつた。このモノアゾ化合物の
構造はマススペクトル及び元素分析で確認した。
mp：198−205℃
MASSスペクトルM+；506
元素分析
再結晶品（１，４−ジオキサンによる）の実測値
（％）
Ｃ Ｈ Ｎ
61.95 6.03 16.25
計算値（C26H30N6O3S）（％）
Ｃ Ｈ Ｎ
61.66 5.93 16.60
かくして得たモノアゾ化合物を実施例１の方法
に従い染色を行つて各種堅牢度の優れた青色のポ
リエステル染色物を得た。
実施例 32〜62
実施例31と同様な方法により下記のモノアゾ化
合物を製造しポリエステル布の染色を行つた。表
中のＸ，Ｙ，Ｗ，Ｖ，Ｒ，R1，R2は次式におけ
る置換表を意味する。
【table】
\
CH3
CH3
/
29 〃 〃 〃 −NHCHO −COOCH 2 OC
2 H 5 -CH
〃 〃 665
\
C 2 H 5
30 〃 〃 〃 〃 −CONHCH ３
−H
〃 645
Example 31 3.3 parts of 2-amino-3-cyano-4-methyl-5-formylthiophene was cooled to below 5°C96
It was gradually added to 12.4 parts of % sulfuric acid and dissolved. Add to this solution a mixed acid consisting of 5 parts acetic acid and 1 part propionic acid.
Add 30 parts at below 10°C. Next, 6.2 parts of 43% nitrosyl sulfuric acid was added and stirred for 2 hours at 5° C. or lower to diazotize. The previously obtained diazotized solution is added dropwise to 100 parts of a 10% aqueous sulfuric acid solution containing 4.1 parts of 3-(N,N-diethyl)amino-acetanilide and 0.2 parts of sulfamic acid. At this time, crushed ice is appropriately added to keep the reaction solution at 0° C. or lower. Soon, dark blue crystals begin to precipitate. The reaction solution was further stirred at 60°C for 1 hour, and then filtered. After washing with hot water and drying, a dark blue crystal shown by the following formula is obtained.
Got 4.7. 1.8 parts of this monoazo compound was added and dissolved in 15 parts of 1,4-dioxane. Add 1.5 parts of cyanoacetic acid butyl ester, 0.1 part of piperidine, and acetic acid to this solution.
Add 0.1 part and stir at 25-30°C for 1 hour. After confirming the completion of the reaction by thin layer chromatography, 15 parts of methanol is gradually added to precipitate crystals. The crystals were collected, washed with water, and dried to obtain 2.5 parts of dark blue crystals represented by the following formula. The λmax of this monoazo compound was 635 nm in a 75% acetone aqueous solution. The structure of this monoazo compound was confirmed by mass spectrometry and elemental analysis. mp: 198-205℃ MASS spectrum M + ; 506 Elemental analysis Actual value of recrystallized product (in 1,4-dioxane) (%) C H N 61.95 6.03 16.25 Calculated value (C 26 H 30 N 6 O 3 S) (%) C H N 61.66 5.93 16.60 The monoazo compound thus obtained was dyed according to the method of Example 1 to obtain various blue dyed polyester products with excellent fastness. Examples 32 to 62 The following monoazo compounds were produced in the same manner as in Example 31, and polyester cloth was dyed. X, Y, W, V, R, R 1 and R 2 in the table mean a substitution table in the following formula.
【表】【table】
【表】【table】
【表】【table】
【表】
／
61 −CH
〃 631
＼
C２H５
62 −C２H５ −C２H４COOC
４H９−n 〃 649
実施例 63
実施例31で得た分散化した染料４部、セルパー
ルSM−100（商品名：安達糊料製グアガム系糊
剤）60部、塩素酸ソーダ0.5部、酒石酸0.2部、イ
ンプルーバ−880（商品名：横浜ポリマー研究所製
均染剤）2.0部を微湯温33.3部に加えホモミキサ
ーにて充分にかきまぜる。この色糊をポリエステ
ル布に印捺し中間乾燥後175℃で５分間過熱蒸気
によるHTスチーミングを行い次いで脱糊、還元
洗浄し水洗乾燥する。青色の染布を得た。このも
のの各種堅牢度は良好であつた。
実施例 64
実施例１とほヾ同様な操作により調製したジア
ゾ化液を１−Ｎ−シアノエチル−ナフチルアミン
6.6部とスルフアミン酸0.2部を含む10％硫酸水溶
液100部に徐々に滴下する。このカツプリング液
に時々砕氷を加えて０℃以下に保持する。まもな
く暗青色の結晶が析出してくる。更にこの反応液
を60℃で１時間かきまぜた後ロ過する。湯洗乾燥
して次式で示される暗青色結晶5.9部を得た。こ
のモノアゾ化合物のλmax（75％アセトン）であ
つた。このモノアゾ化合物の構造はマススペクト
ルで確認した。
mp：190−195℃
MASSスペクトル：M+：427
実施例 65〜102
実施例１，31又は64とほゞ同様な方法により下記
のモノアゾ化合物を製造し、ポリエステル布の染
色を行つた。
表中のＸ，Ｙ，Ｒ及びＫは次式（）における
置換基を意味する。
【table】 /
61 −CH
〃 631
\
C 2 H 5
62 −C 2 H 5 −C 2 H 4 COOC
4 H 9 −n 〃 649
Example 63 4 parts of the dispersed dye obtained in Example 31, 60 parts of Celpar SM-100 (trade name: guar gum-based glue manufactured by Adachi Paste Co., Ltd.), 0.5 parts of sodium chlorate, 0.2 parts of tartaric acid, Improver 880 ( Add 2.0 parts (product name: Leveling agent manufactured by Yokohama Polymer Research Institute) to 33.3 parts of lukewarm water and stir thoroughly using a homomixer. This colored paste is printed on a polyester cloth, and after intermediate drying, it is subjected to HT steaming using superheated steam at 175°C for 5 minutes, followed by descaling, reduction washing, washing with water, and drying. A blue dyed cloth was obtained. The various fastness properties of this product were good. Example 64 A diazotized solution prepared by almost the same procedure as in Example 1 was added to 1-N-cyanoethyl-naphthylamine.
Gradually add dropwise to 100 parts of a 10% aqueous sulfuric acid solution containing 6.6 parts of sulfamic acid and 0.2 parts of sulfamic acid. This coupling liquid is maintained at below 0°C by occasionally adding crushed ice. Soon, dark blue crystals begin to precipitate. This reaction solution was further stirred at 60°C for 1 hour and then filtered. After washing with hot water and drying, 5.9 parts of dark blue crystals represented by the following formula were obtained. This was the λmax (75% acetone) of this monoazo compound. The structure of this monoazo compound was confirmed by mass spectrometry. mp: 190-195°C MASS spectrum: M + : 427 Examples 65 to 102 The following monoazo compounds were produced in substantially the same manner as in Examples 1, 31 or 64, and polyester cloth was dyed. X, Y, R and K in the table mean substituents in the following formula ().
【表】【table】
【表】【table】
【表】【table】
Claims (1)
子、C1〜C4のアルキル基、C1〜4のアルコキシ基、
又はC2〜7のアルコキシアルコキシ基を、Ｖは水素
原子、クロル原子、ブロム原子、C1〜3のアルキル
基、C1〜3のアルコキシ基、水酸基、又は−
NHCOR3基（但しR3は水素原子、C1〜6のアルキ
ル基又はフエニル基を表わす。）を、R1，R2は
各々独立に水素原子、アリル基、アリール基、シ
クロヘキシル基、アラルキル基、C1〜6のアルキル
基、【式】基（但しR4はC1〜4のア ルキル基又はアリル基を表わす。）又は水酸基、
C1〜4のアルコキシ基、C2〜7のアルコキシアルコキ
シ基、アリールオキシ基、アリルオキシ基、シア
ノ基、C1〜3のアルカノイルオキシ基、アリーロイ
ルオキシ基、（C1〜4−アルコキシ）カルボニル基、
（C2〜7−アルコキシアルコキシ）カルボニル基、
アラルキルオキシカルボニル基、（C1〜6−アルコ
キシ）カルボニルオキシ基、シクロヘキシルオキ
シ基又はハロゲン原子により置換されたC1〜6のア
ルキル基を表わす。）【式】基 （但しR5は水素原子、C1〜3のアルキル基又は−
NHCOR3基（但しR3は前記と同じ意味を表わ
す。）を、R6、R7及びR8は水素原子又はメチル基
を表わし、R1は前記と同じ意味を表わす。）
【式】基（但しR1，R2は前記と同じ 意味を表わす。）【式】基（但しR1， R2及びR6は前記と同じ意味を表わす。）を表わ
し、Ｘはニトロ基、シアノ基、（C1〜4−アルコキ
シ）カルボニル基、−CONHR3基（但しR3は前記
と同じ意味を表わす。）又は−COR3基（但しR3
は前記と同じ意味を表わす。）を、Ｙは水素原子、
C1〜4のアルキル基又はフエニル基を、Ｒはシアノ
基、（C1〜6−アルコキシ）カルボニル基、（C2〜9−
アルコキシアルコキシ）カルボニル基、（C3〜4−
アルケニルオキシ）カルボニル基、−CONHR3基
（但しR3は前記と同じ意味を表わす。）又は−
COR3基（但しR3は前記と同じ意味を表わす。）
を表わす。〕 で表わされる水不溶性モノアゾ化合物。 ２ 式（） 〔式（）においてＫは【式】基 （但しＷは水素原子、クロル原子、ブロム原子、
C1〜4のアルキル基、C1〜4のアルコキシ基、又は
C2〜7のアルコキシアルコキシ基を、Ｖは水素原
子、クロル原子、ブロム原子、C1〜3のアルキル
基、C1〜3のアルコキシ基、水酸基又は−
NHCOR3基（但しR3は水素原子、C1〜6のアルキ
ル基又はフエニル基を表わす。）を、R1，R2は
各々独立に水素原子、アリル基、アリール基、シ
クロヘキシル基、アラルキル基、C1〜6のアルキル
基、【式】基（但しR4はC1〜4のア ルキル基又はアリル基を表わす。）又は水酸基、
C1〜4のアルコキシ基、C2〜7のアルコキシアルコキ
シ基、アリールオキシ基、アリルオキシ基、シア
ノ基、C1〜3−アルカノイルオキシ基、アリーロイ
ルオキシ基、（C1〜4−アルコキシ）カルボニル基、
（C2〜7−アルコキシアルコキシ）カルボニル基、
アラルキルオキシカルボニル基、（C1〜6−アルコ
キシ）カルボニルオキシ基、シクロヘキシルオキ
シ基又はハロゲン原子により置換されたC1〜6のア
ルキル基を表わす。）【式】基 （但しR5は水素原子、C1〜3のアルキル基又は−
NHCOR3基（但しR3は前記と同じ意味を表わ
す。）をR6、R7及びR8は水素原子又はメチル基を
表わし、R1は前記と同じ意味を表わす。）；
【式】基（但しR1，R2は前記と同じ 意味を表わす。）；【式】基（但し R1，R2及びR6は前記と同じ意味を表わす。）を表
わしＸはニトロ基、シアノ基、（C1〜4−アルコキ
シ）カルボニル基、−CONHR3基（但しR3は前記
と同じ意味を表わす。）又は−COR3基（但しR3
は前記と同じ意味を表わす。）を、Ｙは水素原子、
C1〜4のアルキル基又はフエニル基を、Ｒはシアノ
基、（C1〜6−アルコキシ）カルボニル基、（C2〜9−
アルコキシアルコキシ）カルボニル基、（C3〜4−
アルケニルオキシ）カルボニル基、−CONHR3基
（但しR3は前記と同じ意味を表わす。）又は−
COR3基（但しR3は前記と同じ意味を表わす。）
を表わす。〕 で表わされる水不溶性モノアゾ化合物を単独で又
は２種以上混合して用いることを特徴とする疎水
性繊維の染色又は捺染法。[Claims] 1. Formula (1) () [In formula (), K is [Formula] group (where W is a hydrogen atom, a chlorine atom, a bromine atom, a C 1 to C 4 alkyl group, a C 1 to 4 alkoxy group,
or a C2-7 alkoxyalkoxy group, where V is a hydrogen atom, a chloro atom, a bromine atom, a C1-3 alkyl group, a C1-3 alkoxy group, a hydroxyl group, or -
NHCOR 3 group (wherein R 3 represents a hydrogen atom, a C 1-6 alkyl group, or a phenyl group), R 1 and R 2 are each independently a hydrogen atom, an allyl group, an aryl group, a cyclohexyl group, an aralkyl group. , a C 1-6 alkyl group, a [Formula] group (wherein R 4 represents a C 1-4 alkyl group or an allyl group), or a hydroxyl group,
C1-4 alkoxy group, C2-7 alkoxyalkoxy group, aryloxy group, allyloxy group, cyano group, C1-3 alkanoyloxy group, aryloyloxy group, ( C1-4 -alkoxy)carbonyl basis,
( C2-7 -alkoxyalkoxy)carbonyl group,
It represents an aralkyloxycarbonyl group, a ( C1-6 -alkoxy)carbonyloxy group, a cyclohexyloxy group, or a C1-6 alkyl group substituted with a halogen atom. ) [Formula] Group (where R 5 is a hydrogen atom, a C 1-3 alkyl group, or -
NHCOR 3 group (R 3 has the same meaning as above), R 6 , R 7 and R 8 each represent a hydrogen atom or a methyl group, and R 1 has the same meaning as above. )
[Formula] represents a group (however, R 1 and R 2 have the same meanings as above) [Formula] represents a group (however, R 1 , R 2 and R 6 have the same meanings as above), and X is a nitro group , cyano group, (C 1-4 -alkoxy)carbonyl group, -CONHR 3 group (however, R 3 represents the same meaning as above) or -COR 3 group (however, R 3
has the same meaning as above. ), Y is a hydrogen atom,
C 1-4 alkyl group or phenyl group, R is cyano group, (C 1-6 -alkoxy)carbonyl group, (C 2-9 -
alkoxyalkoxy) carbonyl group, (C 3-4 −
alkenyloxy) carbonyl group, -CONHR 3 group (however, R 3 represents the same meaning as above), or -
COR 3 groups (However, R 3 has the same meaning as above.)
represents. ] A water-insoluble monoazo compound represented by 2 formula () [In formula (), K is [formula] group (however, W is a hydrogen atom, a chlorine atom, a bromine atom,
C 1-4 alkyl group, C 1-4 alkoxy group, or
A C 2-7 alkoxyalkoxy group, V is a hydrogen atom, a chlorine atom, a bromine atom, a C 1-3 alkyl group, a C 1-3 alkoxy group, a hydroxyl group, or -
NHCOR 3 group (wherein R 3 represents a hydrogen atom, a C 1-6 alkyl group, or a phenyl group), R 1 and R 2 are each independently a hydrogen atom, an allyl group, an aryl group, a cyclohexyl group, an aralkyl group. , a C 1-6 alkyl group, a [Formula] group (wherein R 4 represents a C 1-4 alkyl group or an allyl group), or a hydroxyl group,
C1-4 alkoxy group, C2-7 alkoxyalkoxy group, aryloxy group, allyloxy group, cyano group, C1-3 -alkanoyloxy group, aryloyloxy group, ( C1-4 -alkoxy)carbonyl basis,
( C2-7 -alkoxyalkoxy)carbonyl group,
It represents an aralkyloxycarbonyl group, a ( C1-6 -alkoxy)carbonyloxy group, a cyclohexyloxy group, or a C1-6 alkyl group substituted with a halogen atom. ) [Formula] Group (where R 5 is a hydrogen atom, a C 1-3 alkyl group, or -
NHCOR 3 group (R 3 has the same meaning as above), R 6 , R 7 and R 8 each represent a hydrogen atom or a methyl group, and R 1 has the same meaning as above. );
[Formula] represents a group (wherein R 1 and R 2 have the same meanings as above); [Formula] represents a group (however, R 1 , R 2 and R 6 have the same meanings as above); X is a nitro group , cyano group, (C 1-4 -alkoxy)carbonyl group, -CONHR 3 group (however, R 3 represents the same meaning as above) or -COR 3 group (however, R 3
has the same meaning as above. ), Y is a hydrogen atom,
C 1-4 alkyl group or phenyl group, R is cyano group, (C 1-6 -alkoxy)carbonyl group, (C 2-9 -
alkoxyalkoxy) carbonyl group, (C 3-4 −
alkenyloxy) carbonyl group, -CONHR 3 group (however, R 3 represents the same meaning as above), or -
COR 3 groups (However, R 3 has the same meaning as above.)
represents. ] A method for dyeing or printing hydrophobic fibers, characterized in that a water-insoluble monoazo compound represented by the following is used alone or in a mixture of two or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7936083A JPS59204658A (en) | 1983-05-09 | 1983-05-09 | Water-insoluble monoazo compound and method for dyeing or printing hydrophobic fiber using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7936083A JPS59204658A (en) | 1983-05-09 | 1983-05-09 | Water-insoluble monoazo compound and method for dyeing or printing hydrophobic fiber using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59204658A JPS59204658A (en) | 1984-11-20 |
| JPH0316983B2 true JPH0316983B2 (en) | 1991-03-06 |
Family
ID=13687724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7936083A Granted JPS59204658A (en) | 1983-05-09 | 1983-05-09 | Water-insoluble monoazo compound and method for dyeing or printing hydrophobic fiber using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59204658A (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3427200A1 (en) * | 1984-07-24 | 1986-01-30 | Basf Ag, 6700 Ludwigshafen | METHINE DYES |
| CH664762A5 (en) * | 1984-08-30 | 1988-03-31 | Sandoz Ag | THIOPHENIC AZO DYES. |
| US5206375A (en) * | 1985-03-02 | 1993-04-27 | Basf Aktiengesellschaft | Thiophene derivatives |
| IN167384B (en) * | 1985-05-14 | 1990-10-20 | Basf Ag | |
| US5283326A (en) * | 1985-05-14 | 1994-02-01 | Sandoz Ag | Dyes containing thiophene radicals |
| DE3734586A1 (en) * | 1987-10-13 | 1989-05-03 | Basf Ag | NAVY BLUE AND BLACK DYE MIXTURES |
| DE3818404A1 (en) * | 1988-05-31 | 1989-12-07 | Basf Ag | METHOD FOR TRANSMITTING AZO DYES |
| DE3902005A1 (en) * | 1989-01-25 | 1990-07-26 | Basf Ag | THIOPHENAZO DYES WITH A CLUTCH COMPONENT BASED ON M-PHENYLENE DIAMINE |
| DE4132074A1 (en) * | 1991-09-26 | 1993-04-01 | Basf Ag | AZO DYES WITH A CHINOLINE SERIES CLUTCH COMPONENT |
| TW324021B (en) * | 1994-03-08 | 1998-01-01 | Daistar Japan Kk | Mono-azo dyestuff |
| US6069276A (en) * | 1999-03-05 | 2000-05-30 | Milliken & Company | Oxyalkylene-substituted m-amidoaniline intermediate |
-
1983
- 1983-05-09 JP JP7936083A patent/JPS59204658A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59204658A (en) | 1984-11-20 |
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