JPS6228818B2 - - Google Patents
Info
- Publication number
- JPS6228818B2 JPS6228818B2 JP53104498A JP10449878A JPS6228818B2 JP S6228818 B2 JPS6228818 B2 JP S6228818B2 JP 53104498 A JP53104498 A JP 53104498A JP 10449878 A JP10449878 A JP 10449878A JP S6228818 B2 JPS6228818 B2 JP S6228818B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- amino
- nitro
- phenyl
- thiophene
- 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 β-cyanoethoxy group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 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
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- NCCMCRFYSZRBBG-UHFFFAOYSA-N ethyl 5-amino-4-cyano-3-methylthiophene-2-carboxylate Chemical compound CCOC(=O)C=1SC(N)=C(C#N)C=1C NCCMCRFYSZRBBG-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- CFBYBPOBHYGXNZ-UHFFFAOYSA-N 2-amino-4-methyl-5-nitrothiophene-3-carbonitrile Chemical compound CC1=C([N+]([O-])=O)SC(N)=C1C#N CFBYBPOBHYGXNZ-UHFFFAOYSA-N 0.000 description 1
- VVLPOLLOKMOHOP-UHFFFAOYSA-N 2-amino-4-methylthiophene-3-carbonitrile Chemical compound CC1=CSC(N)=C1C#N VVLPOLLOKMOHOP-UHFFFAOYSA-N 0.000 description 1
- RMSVWOYCWFNSCM-UHFFFAOYSA-N 2-amino-4-phenylthiophene-3-carbonitrile Chemical compound N#CC1=C(N)SC=C1C1=CC=CC=C1 RMSVWOYCWFNSCM-UHFFFAOYSA-N 0.000 description 1
- CFKZMYPOJOKAAD-UHFFFAOYSA-N 2-amino-5-nitrothiophene-3-carbonitrile Chemical compound NC=1SC([N+]([O-])=O)=CC=1C#N CFKZMYPOJOKAAD-UHFFFAOYSA-N 0.000 description 1
- XVGHZFWFGXDIOU-UHFFFAOYSA-N 2-aminothiophene-3-carbonitrile Chemical compound NC=1SC=CC=1C#N XVGHZFWFGXDIOU-UHFFFAOYSA-N 0.000 description 1
- DZRZHFOFVWAKGT-UHFFFAOYSA-N 3,5-dinitrothiophen-2-amine Chemical compound NC=1SC([N+]([O-])=O)=CC=1[N+]([O-])=O DZRZHFOFVWAKGT-UHFFFAOYSA-N 0.000 description 1
- KDILIMALWBUMCY-UHFFFAOYSA-N 4-methyl-3,5-dinitrothiophen-2-amine Chemical compound CC1=C([N+]([O-])=O)SC(N)=C1[N+]([O-])=O KDILIMALWBUMCY-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 239000000987 azo dye Substances 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- MKJQYFVTEPGXIE-UHFFFAOYSA-N ethyl 2-aminothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1N MKJQYFVTEPGXIE-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OVLUSSXPOANNKZ-UHFFFAOYSA-N methyl 2-amino-5-nitrothiophene-3-carboxylate Chemical compound COC(=O)C=1C=C([N+]([O-])=O)SC=1N OVLUSSXPOANNKZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000001047 purple dye Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3691—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and sulfur as heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
Description
本発明は、一般式
で表わされる新規化合物に関する。この式中Ｄは
チオフエン系又はベンゾイソチアゾール系の残
基、Ｂは場合により塩素原子、臭素原子、C1〜
C4−アルコキシ基、β−シアノエトキシ基、メ
チル基、エチル基もしくはC1〜C4−アルカノイ
ルアミノ基により置換されたフエニル基、R1及
びR2は水素原子、アリル基、フエニル基又はC1
〜C4−アルキル基（これらは場合により水酸
基、シアン基、C1〜C4−アルコキシカルボニル
基もしくはC1〜C4−アルカノイルオキシ基によ
り置換されている）を意味する。
残基Ｄの置換基は、たとえばC1〜C4−アルキ
ル基、C1〜C4−アルコキシ基、塩素原子、臭素
原子、シアン基、ニトロ基、C2〜C4−アルキル
メルカプト基、フエニルメルカプト基、C1〜C4
−アルキルスルホニル基、C1〜C4−アルコキシ
カルボニルエチル−メルカプト基、C1〜C4−ア
ルコキシカルボニル基、カルバモイル基、スルフ
アモイル基、あるいは塩素原子、臭素原子、ニト
ロ基、シアン基、メチル基もしくはメトキシ基に
より置換されていてもよいフエニルアゾ基であ
る。
個々のジアゾ成分Ｄ−NH2の例は下記のもので
ある。２−アミノ−３−シアノ−チオフエン、２
−アミノ−３−エトキシカルボニル−チオフエ
ン、２−アミノ−３−シアノ−４−メチル−チオ
フエン、２−アミノ−３−シアノ−４−フエニル
−チオフエン、２−アミノ−３−シアノ−４−メ
チル−５−エトキシカルボニル−チオフエン、２
−アミノ−３−シアノ−５−ニトロ−チオフエ
ン、２−アミノ−３−シアノ−４−メチル−５−
ニトロ−チオフエン、２−アミノ−３・５−ジニ
トロ−チオフエン、２−アミノ−３−メトキシカ
ルボニル−５−ニトロ−チオフエン、２−アミノ
−３・５−ジニトロ−４−メチル−チオフエン、
２−アミノ−３−エトキシカルボニル−４−フエ
ニル−５−アゾフエニル−チオフエン、２−アミ
ノ−３−メトキシカルボニル−５−アゾフエニル
−チオフエン、２−アミノ−３−メトキシカルボ
ニル−４−フエニル−５−アゾ−ｐ−クロルフエ
ニル−チオフエン、２−アミノ−３−メトキシカ
ルボニル−４−フエニル−５−アゾ−２・４−ジ
クロルフエニル−チオフエン、２−アミノ−３−
ニトロ−４−アゾフエニル−チオフエン、２−ア
ミノ−３−ニトロ−４−メチル−５−アゾフエニ
ル−チオフエン、３−アミノ−ベンゾイソチアゾ
ール−２・１、３−アミノ−５−ニトロ−ベンゾ
イソチアゾール−２・１、３−アミノ−５−ニト
ロ−７−ブロム−ベンゾイソチアゾール−２・
１、３−アミノ−５−ニトロ−７−クロル−ベン
ゾイソチアゾール−２・１、３−アミノ−５−ニ
トロ−７−シアノ−ベンゾイソチアゾール−２・
１、３−アミノ−５−ジエチルアミノスルホニル
−ベンゾイソチアゾール−２・１、３−アミノ−
５・７−ジニトロ−ベンゾイソチアゾール−２・
１、３−アミノ−５−クロル−ベンゾイソチアゾ
ール−２・１、３−アミノ−５・７−ジクロル−
ベンゾイソチアゾール−２・１、７−ニトロ−４
−アミノ−ベンゾイソチアゾール−１・２、７−
ニトロ−４−アミノ−５−ブロム−ベンゾイソチ
アゾール−１・２、７−ニトロ−４−アミノ−５
−クロル−ベンゾイソチアゾール−１・２、７−
ニトロ−４−アミノ−５−シアノ−ベンゾイソチ
アゾール−１・２。
特に好ましいＲは、フエニル基、C1〜C4−ア
ルコキシフエニル基、クロルフエニル基、C1〜
C4−アルカノイルアミノフエニル基又はβ２−
シアノエトキシフエニル基である。
R1及びR2は同一でも異なつてもよく、水素原
子のほか、１〜４個の炭素原子を有するアルキル
基、アリル基、場合によりシアノ基もしくは水酸
基により置換されたアルキル基、フエニル基、な
らびにアルカノイルオキシアルキル基又はアルコ
キシカルボニルアルキル基である。
個々のR1及びR2は例の下記のものである。ア
ルキル基としてメチル、エチル、プロピレ、ブチ
ル、ヒドロキシアルキル基としてβ−ヒドロキシ
エチルもしくは−プロピル、γ−ヒドロキシプロ
ピル、β−C1〜C4−アルコキシカルボニルエチ
ル、ならびに−CH2CH2CN、−CH2CH＝CH2、−
C6H5、−CH2−CH2−Ｏ−Ｂ、−（CH2）3−Ｏ−
Ｂ、
The present invention is based on the general formula This invention relates to a novel compound represented by In this formula, D is a thiophene-based or benzisothiazole-based residue, B is a chlorine atom, a bromine atom, or a C 1 -
C 4 -alkoxy group, β-cyanoethoxy group, methyl group, ethyl group or phenyl group substituted with C 1 -C 4 -alkanoylamino group, R 1 and R 2 are hydrogen atoms, allyl group, phenyl group or C 1
~ C4 -alkyl group, which is optionally substituted by a hydroxyl group, a cyanogen group, a C1- C4 -alkoxycarbonyl group or a C1 - C4 -alkanoyloxy group. Substituents for the residue D are, for example, C1 - C4 -alkyl groups, C1 - C4 -alkoxy groups, chlorine atoms, bromine atoms, cyanogen groups, nitro groups, C2 - C4 -alkylmercapto groups, enylmercapto group, C1 - C4
-alkylsulfonyl group, C1 - C4 -alkoxycarbonylethyl-mercapto group, C1 - C4 -alkoxycarbonyl group, carbamoyl group, sulfamoyl group, or chlorine atom, bromine atom, nitro group, cyan group, methyl group, or It is a phenylazo group which may be substituted with a methoxy group. Examples of individual diazo components D- NH2 are as follows. 2-Amino-3-cyano-thiophene, 2
-amino-3-ethoxycarbonyl-thiophene, 2-amino-3-cyano-4-methyl-thiophene, 2-amino-3-cyano-4-phenyl-thiophene, 2-amino-3-cyano-4-methyl- 5-ethoxycarbonyl-thiophene, 2
-amino-3-cyano-5-nitro-thiophene, 2-amino-3-cyano-4-methyl-5-
Nitro-thiophene, 2-amino-3,5-dinitro-thiophene, 2-amino-3-methoxycarbonyl-5-nitro-thiophene, 2-amino-3,5-dinitro-4-methyl-thiophene,
2-amino-3-ethoxycarbonyl-4-phenyl-5-azophenyl-thiophene, 2-amino-3-methoxycarbonyl-5-azophenyl-thiophene, 2-amino-3-methoxycarbonyl-4-phenyl-5-azo -p-chlorophenyl-thiophene, 2-amino-3-methoxycarbonyl-4-phenyl-5-azo-2,4-dichlorophenyl-thiophene, 2-amino-3-
Nitro-4-azophenyl-thiophene, 2-amino-3-nitro-4-methyl-5-azophenyl-thiophene, 3-amino-benzisothiazole-2.1, 3-amino-5-nitro-benzisothiazole- 2.1,3-amino-5-nitro-7-bromo-benziisothiazole-2.
1,3-amino-5-nitro-7-chloro-benzisothiazole-2・1,3-amino-5-nitro-7-cyano-benzisothiazole-2・
1,3-amino-5-diethylaminosulfonyl-benzisothiazole-2,1,3-amino-
5,7-dinitro-benziisothiazole-2.
1,3-amino-5-chloro-benzisothiazole-2,1,3-amino-5,7-dichloro-
Benziisothiazole-2.1,7-nitro-4
-Amino-benziisothiazole-1,2,7-
Nitro-4-amino-5-bromo-benzisothiazole-1,2,7-nitro-4-amino-5
-Chloro-benziisothiazole-1,2,7-
Nitro-4-amino-5-cyano-benziisothiazole-1.2. Particularly preferred R is a phenyl group, a C 1 -C 4 -alkoxyphenyl group, a chlorophenyl group, a C 1 -
C 4 -alkanoylaminophenyl group or β2-
It is a cyanoethoxyphenyl group. R 1 and R 2 may be the same or different, and in addition to a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an allyl group, an alkyl group optionally substituted with a cyano group or a hydroxyl group, a phenyl group, It is an alkanoyloxyalkyl group or an alkoxycarbonylalkyl group. The individual R 1 and R 2 are as follows in the example. Methyl, ethyl, propylene, butyl as alkyl groups, β-hydroxyethyl or -propyl, γ-hydroxypropyl, β-C 1 -C 4 -alkoxycarbonylethyl as hydroxyalkyl groups, and -CH 2 CH 2 CN, -CH 2 CH=CH 2 , -
C 6 H 5 , -CH 2 -CH 2 -O-B, -(CH 2 ) 3 -O-
B,
【式】（式中のＢはC1〜C4−
アルカノイル基を意味する）。
R1及びR2として好ましいものは、水素原子、
メチル基、エチル基、プロピル基、ブチル基、ア
リル基、ベンジル基、β−エトキシカルボニルエ
チル基、β−シアノエチル基、β−ヒドロキシエ
チル基、β−アセトキシエチル基又はフエニル基
である。
一般式の化合物は、次式
Ｄ−NH2
のアミンのジアゾニウム化合物を、次式
のカツプリング成分と反応させることにより製造
できる。製造の詳細は実施例に示され、例中の部
及び％は特に指示しない限り重量に関する。
式の染料は合成繊維上に黄色ないし緑色の染
色を与える。この染色は良好な堅牢性を有し、特
に光−、湿潤−及び熱堅牢性が優れている。その
ほかこの染料は濃色である。一部は天然繊維たと
えば木綿にも適しており、たとえばドイツ特許
1796811号明細書に記載の方法によつて染色でき
る。
実施例 １
２−アミノ−３−シアノ−４−メチル−５−エ
トキシカルボニルチオフエン10.5部を氷酢酸100
部及び85％燐酸100部の混合物に溶解し、０〜５
℃でニトロシル硫酸（N2O312.8％）14.8部を用い
てジアゾ化する。２時間撹拌したのち過剰のジア
ゾ化剤を尿素の添加により分解し、氷酢酸50ml中
の２−ジエチルアミノ−４−フエニル−チアゾリ
ウムヒドロクロリード14.6部の溶液を添加する。
反応混合物を氷上に注ぎ、紫色の染料を吸引過
し、水洗する。収量は20.6部である。
同様にして実施例２〜12の染料が製造される。[Formula] (B in the formula means a C 1 -C 4 -alkanoyl group). Preferred R 1 and R 2 are hydrogen atoms,
A methyl group, an ethyl group, a propyl group, a butyl group, an allyl group, a benzyl group, a β-ethoxycarbonylethyl group, a β-cyanoethyl group, a β-hydroxyethyl group, a β-acetoxyethyl group, or a phenyl group. The compound of the general formula is a diazonium compound of the amine of the following formula D- NH2 , and the compound of the following formula is It can be produced by reacting with a coupling component of Preparation details are given in the examples, in which parts and percentages relate to weight unless otherwise indicated. The formula dye provides a yellow to green dyeing on synthetic fibers. The dyeings have good fastness properties, in particular light, wet and heat fastnesses. Additionally, this dye has a deep color. Some are also suitable for natural fibers, e.g. cotton, e.g. German patent
It can be dyed by the method described in No. 1796811. Example 1 10.5 parts of 2-amino-3-cyano-4-methyl-5-ethoxycarbonylthiophene was dissolved in 100 parts of glacial acetic acid.
Dissolved in a mixture of 100 parts and 85% phosphoric acid, 0 to 5 parts
Diazotize with 14.8 parts of nitrosyl sulfate (N 2 O 3 12.8%) at °C. After stirring for 2 hours, the excess diazotizing agent is destroyed by the addition of urea and a solution of 14.6 parts of 2-diethylamino-4-phenyl-thiazolium hydrochloride in 50 ml of glacial acetic acid is added.
The reaction mixture is poured onto ice, the purple dye is filtered off with suction and washed with water. Yield is 20.6 parts. The dyes of Examples 2 to 12 are produced in a similar manner.
【表】【table】
【表】【table】
【表】
実施例 13
４−アミノ−７−ニトロ−１・２−ベンゾイソ
チアゾール9.8部を、０〜５℃で98％硫酸70部及
びニトロシル硫酸（36.5％）20部からの混合物に
加え、４時間撹拌したのち過剰のジアゾ化剤を尿
素の添加により分解する。他方、２−（Ｎ・Ｎ−
ジアリル）−アミノ−４−（4′−メトキシフエニル
チアゾール）17部をジメチルホルムアミド80部に
溶解し、氷800部及び水に溶解した乳化剤２部か
らの混合物に加える。この乳化液に前記のジアゾ
溶液を10分間に加え、15時間撹拌したのち青色の
アゾ染料を吸引過し、水で中性になるまで洗つ
て乾燥する。収量は16部である。λnax値：622n
ｍ。
実施例13と同様にして下記表に示す染料が製造
される。表中の括弧内の数値はλnax値（ｎｍ）
である。[Table] Example 13 9.8 parts of 4-amino-7-nitro-1,2-benziisothiazole are added to a mixture of 70 parts of 98% sulfuric acid and 20 parts of nitrosyl sulfuric acid (36.5%) at 0-5°C, After stirring for 4 hours, excess diazotizing agent is decomposed by addition of urea. On the other hand, 2-(N・N-
17 parts of diallyl)-amino-4-(4'-methoxyphenylthiazole) are dissolved in 80 parts of dimethylformamide and added to a mixture of 800 parts of ice and 2 parts of emulsifier dissolved in water. The above diazo solution was added to this emulsion for 10 minutes, and after stirring for 15 hours, the blue azo dye was filtered off by suction, washed with water until neutral, and dried. Yield is 16 parts. λ nax value: 622n
m. The dyes shown in the table below are produced in the same manner as in Example 13. The numbers in parentheses in the table are λ nax values (nm)
It is.
【表】【table】
Claims (1)
ル系の残基、Ｒは塩素原子、臭素原子、C1〜C4
−アルコキシ基、β−シアノエトキシ基、メチル
基、エチル基もしくはC1〜C4−アルカノイルア
ミノ基により置換されていてもよいフエニル基、
R1及びR2は水素原子、アリル基、又は水酸基、
シアン基、C1〜C4−アルコキシカルボニル基も
しくはC1〜C4−アルカノイルオキシ基により置
換されていてもよいC1〜C4−アルキル基又はフ
エニル基を意味する）で表わされるアゾ染料。 ２ Ｄがシアン基、ニトロ基、C1〜C8−アルコ
キシカルボニル基、メチル基、フエニル基もしく
はフエニルアゾ基（塩素原子、臭素原子もしくは
ニトロ基により置換されていてもよい）により置
換されたチエニル基、又は塩素原子、臭素原子、
ニトロ基もしくはシアン基により置換されたベン
ゾイソチアゾリル−２・１基又はベンゾイソチア
ゾリル−１・２基であることを特徴とする、特許
請求の範囲第１項に記載の染料。 ３ 次式 Ｄ−NH2 のアミンのジアゾニウム化合物を、次式 （これらの式中の記号は後記の意味を有する）の
カツプリング成分と反応させることを特徴とす
る、一般式 （式中Ｄはチオフエン系又はベンゾイソチアゾー
ル系の残基、Ｒは塩素原子、臭素原子、C1〜C4
−アルコキシ基、β−シアノエトキシ基、メチル
基、エチル基もしくはC1〜C4−アルカノイルア
ミノ基により置換されていてもよいフエニル基、
R1及びR2は水素原子、アリル基、又は水酸基、
シアン基、C1〜C4−アルコキシカルボニル基も
しくはC1〜C4−アルカノイルオキシ基により置
換されていてもよいC1〜C4−アルキル基又はフ
エニル基を意味する）で表わされるアゾ染料の製
法。[Claims] 1. General formula (In the formula, D is a thiophene-based or benzisothiazole-based residue, R is a chlorine atom, a bromine atom, C 1 to C 4
- a phenyl group optionally substituted with an alkoxy group, a β-cyanoethoxy group, a methyl group, an ethyl group or a C1 - C4 -alkanoylamino group,
R 1 and R 2 are hydrogen atoms, allyl groups, or hydroxyl groups,
cyan group, a C1 - C4 -alkyl group or a phenyl group which may be substituted by a C1 - C4 -alkoxycarbonyl group or a C1- C4 -alkanoyloxy group. 2 A thienyl group in which D is substituted with a cyan group, a nitro group, a C1 - C8 -alkoxycarbonyl group, a methyl group, a phenyl group or a phenylazo group (which may be substituted with a chlorine atom, a bromine atom or a nitro group) , or chlorine atom, bromine atom,
The dye according to claim 1, which is a benzisothiazolyl-2.1 group or a benzisothiazolyl-1.2 group substituted with a nitro group or a cyan group. 3 The amine diazonium compound of the following formula D-NH 2 is (The symbols in these formulas have the meanings given below) (In the formula, D is a thiophene-based or benzisothiazole-based residue, R is a chlorine atom, a bromine atom, C 1 to C 4
- a phenyl group optionally substituted with an alkoxy group, a β-cyanoethoxy group, a methyl group, an ethyl group or a C1 - C4 -alkanoylamino group,
R 1 and R 2 are hydrogen atoms, allyl groups, or hydroxyl groups,
cyan group, C1 - C4 -alkoxycarbonyl group or C1 - C4 -alkanoyloxy group, meaning a C1 - C4 -alkyl group or phenyl group); Manufacturing method.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772738885 DE2738885A1 (en) | 1977-08-29 | 1977-08-29 | AZO DYES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5446226A JPS5446226A (en) | 1979-04-12 |
| JPS6228818B2 true JPS6228818B2 (en) | 1987-06-23 |
Family
ID=6017579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10449878A Granted JPS5446226A (en) | 1977-08-29 | 1978-08-29 | Novel azo dyestuff |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5446226A (en) |
| CH (1) | CH634864A5 (en) |
| DE (1) | DE2738885A1 (en) |
| FR (1) | FR2401960A1 (en) |
| GB (1) | GB2004561B (en) |
| IT (1) | IT1097943B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63315602A (en) * | 1987-06-12 | 1988-12-23 | 美津濃株式会社 | Pad |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2816507A1 (en) * | 1978-04-15 | 1979-10-25 | Basf Ag | ACID AZO DYES WITH THIAZOLE COUPLING COMPONENTS |
| DE2910806A1 (en) * | 1979-03-20 | 1980-10-02 | Basf Ag | THIAZOL SERIES DYES |
| DE3427201A1 (en) * | 1984-07-24 | 1986-01-30 | Basf Ag, 6700 Ludwigshafen | HETEROCYCLIC AZO DYES |
| GB8704727D0 (en) * | 1987-02-27 | 1987-08-05 | Ici Plc | Aromatic disazo compound |
| DE3833442A1 (en) * | 1988-10-01 | 1990-04-12 | Basf Ag | THIOPHENAZO DYES WITH A CLUTCH COMPONENT FROM THE THIAZOL SERIES |
| US5132412A (en) * | 1988-10-01 | 1992-07-21 | Basf Aktiengesellschaft | Thiazoleazo dyes having a diazo component from the isothiazole or thiadiazole series |
| US5216139A (en) * | 1988-10-01 | 1993-06-01 | Basf Aktiengesellschaft | Thiopheneazo dye based on a coupling component of the thiazole series |
| DE3910289A1 (en) * | 1989-03-30 | 1990-10-04 | Basf Ag | AZO DYES WITH A DIAZO COMPONENT FROM THE AMINOBENZISOTHIAZOLE SERIES |
| DE3910408A1 (en) * | 1989-03-31 | 1990-10-04 | Basf Ag | AZO DYES WHOSE DIAZO AND CLUTCH COMPONENT COMES FROM THE THIAZOLE SERIES |
| DE3917455A1 (en) * | 1989-05-30 | 1990-12-06 | Basf Ag | BENZISOTHIAZOLAZO DYES WITH A CLUTCH COMPONENT FROM THE THIAZOLE OR PYRIDINE RANGE |
| JP2008248211A (en) * | 2007-03-30 | 2008-10-16 | Fujifilm Corp | Azo pigment and azo compound |
| JP2008248212A (en) * | 2007-03-30 | 2008-10-16 | Fujifilm Corp | Azo pigment and azo compound |
| US10926276B2 (en) | 2015-12-09 | 2021-02-23 | Joseph A. McDonnell | Dual sprayer and foam sprayer attachment |
| US10272457B2 (en) | 2015-12-09 | 2019-04-30 | Joseph A. McDonnell | Dual sprayer, and dual sprayer with dual chamber bottle |
| USD821541S1 (en) | 2015-12-30 | 2018-06-26 | Joseph A. McDonnell | Dual sprayer |
| USD944924S1 (en) | 2018-05-08 | 2022-03-01 | For Life Products, Llc | Dual sprayer with screw connection and foam sprayer attachment |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3770719A (en) * | 1967-12-07 | 1973-11-06 | Eastman Kodak Co | 2-amino-4-(azoyl)-azo-thiazole compounds and quaternary derivative thereof |
| US3816391A (en) * | 1971-12-01 | 1974-06-11 | Eastman Kodak Co | 2-amino-4-aryl-5-(2-cyano-4,6-dinitro-phenylazo)thiazole compounds |
-
1977
- 1977-08-29 DE DE19772738885 patent/DE2738885A1/en active Granted
-
1978
- 1978-08-10 IT IT26691/78A patent/IT1097943B/en active
- 1978-08-17 FR FR7823988A patent/FR2401960A1/en active Granted
- 1978-08-23 CH CH893978A patent/CH634864A5/en not_active IP Right Cessation
- 1978-08-25 GB GB7834704A patent/GB2004561B/en not_active Expired
- 1978-08-29 JP JP10449878A patent/JPS5446226A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63315602A (en) * | 1987-06-12 | 1988-12-23 | 美津濃株式会社 | Pad |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2738885C2 (en) | 1988-07-21 |
| DE2738885A1 (en) | 1979-03-22 |
| FR2401960A1 (en) | 1979-03-30 |
| IT1097943B (en) | 1985-08-31 |
| CH634864A5 (en) | 1983-02-28 |
| JPS5446226A (en) | 1979-04-12 |
| FR2401960B3 (en) | 1981-03-27 |
| IT7826691A0 (en) | 1978-08-10 |
| GB2004561A (en) | 1979-04-04 |
| GB2004561B (en) | 1982-04-21 |
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