JPS62185759A - Reactive azo dye - Google Patents
Reactive azo dyeInfo
- Publication number
- JPS62185759A JPS62185759A JP62024934A JP2493487A JPS62185759A JP S62185759 A JPS62185759 A JP S62185759A JP 62024934 A JP62024934 A JP 62024934A JP 2493487 A JP2493487 A JP 2493487A JP S62185759 A JPS62185759 A JP S62185759A
- Authority
- JP
- Japan
- Prior art keywords
- group
- dye
- alkyl group
- amino
- sulfonic acid
- 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.)
- Pending
Links
- 239000000987 azo dye Substances 0.000 title claims description 8
- 239000000975 dye Substances 0.000 claims description 36
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 18
- -1 N-methylanilino group Chemical group 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 2
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 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 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- MWCADZVQNIHFGT-UHFFFAOYSA-N 1-anilinopropan-2-ol Chemical compound CC(O)CNC1=CC=CC=C1 MWCADZVQNIHFGT-UHFFFAOYSA-N 0.000 description 1
- OMQCGHBXGJBBOL-UHFFFAOYSA-N 2-amino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=CC=C1S(O)(=O)=O OMQCGHBXGJBBOL-UHFFFAOYSA-N 0.000 description 1
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 1
- ZCGVPUAAMCMLTM-UHFFFAOYSA-N 2-amino-5-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C=C1S(O)(=O)=O ZCGVPUAAMCMLTM-UHFFFAOYSA-N 0.000 description 1
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- OUXLUOBFBNGHCD-UHFFFAOYSA-N 6-amino-6-chlorocyclohexa-2,4-diene-1-sulfonic acid Chemical compound NC1(Cl)C=CC=CC1S(O)(=O)=O OUXLUOBFBNGHCD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical class OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LAMTXWQPHWUMLX-UHFFFAOYSA-N n-butan-2-ylaniline Chemical compound CCC(C)NC1=CC=CC=C1 LAMTXWQPHWUMLX-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 description 1
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
- D06P1/382—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group directly attached to heterocyclic group
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
本発明は、新規なモノクロルトリアジン系の反応性モノ
アゾ染料、ならびにこの染料化合物を含有する液状染料
調製物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel reactive monoazo dyes based on monochlorotriazine and to liquid dye preparations containing this dye compound.
英国特許８３４３０４号明細書には、トリアジ／残基中
にＮ−メチルアニリノ基を有するモノクロルトリアジン
系の反応性モノアゾ染料が記載されている。GB 834304 describes reactive monoazo dyes based on monochlorotriazine having an N-methylanilino group in the triazide/residue.
本発明は、次式
（ａｌはＣ，％ Ｃ４−アルキル基、Ｃ２〜Ｃ４−アル
コキシ基、塩素原子又は臭素原子、Ｒ２は置換基を有し
うるＣ２〜Ｃ４−アルキル基、Ｒ３は水素原子、０１〜
Ｃ４−アルキル基、ａｔ〜Ｃ４−アルコキシ基、塩素原
子又は臭素原子を意味する）で表わされる反応性アゾ染
料又はその塩である。The present invention is based on the following formula (al is C,% C4-alkyl group, C2-C4-alkoxy group, chlorine atom or bromine atom, R2 is C2-C4-alkyl group which may have a substituent, R3 is hydrogen atom, 01～
C4-alkyl group, at-C4-alkoxy group, chlorine atom or bromine atom) or a salt thereof.
式ＩにおいてＲ１は、例えばメチル基、エチル基、プロ
ピル基、イソプロピル基、ブチル基、イソブチル基、二
級ブチル基、メトキシ基、エトキシ基、プロポキシ基、
インプロポキシ基、ブトキシ基、イソブトキシ基、二級
ブトキシ基、塩素原子又は臭素原子である。In formula I, R1 is, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a secondary butyl group, a methoxy group, an ethoxy group, a propoxy group,
They are an inpropoxy group, a butoxy group, an isobutoxy group, a secondary butoxy group, a chlorine atom, or a bromine atom.
Ｒ２の例は、エチル基、プロピル基、イソプロピル基、
ブチル基、イソブチル基又は二級ブチル基である。０２
〜Ｃ４−アルキル基は、水酸基又は０１〜Ｃ４−アルコ
キシ基により置換されてもよい。その例は次の基である
。２−ヒドロキシエチル、２−ヒドロキシプロピル、６
−ヒドロキシプロピル、２−ヒドロキシブチル、２−メ
トキシエチル、２−エトキシエチル、２−メトキシプロ
ピル又は２−エトキシエチル。Examples of R2 are ethyl group, propyl group, isopropyl group,
It is a butyl group, an isobutyl group or a secondary butyl group. 02
The ~C4-alkyl group may be substituted by a hydroxyl group or a 01-C4-alkoxy group. An example is the following group: 2-hydroxyethyl, 2-hydroxypropyl, 6
-Hydroxypropyl, 2-hydroxybutyl, 2-methoxyethyl, 2-ethoxyethyl, 2-methoxypropyl or 2-ethoxyethyl.
Ｒ３の例は、水素原子、メチル基、エチル基、プロピル
基、インプロピル基、ブチル基、インブチル基、二級ブ
チル基、メトキシ基、エトキシ基、プロポキシ基、イン
プロポキシ基、ブトキシ基、インブトキシ基、二級ブト
キシ基、塩素原子又は臭素原子である。Examples of R3 are a hydrogen atom, a methyl group, an ethyl group, a propyl group, an inpropyl group, a butyl group, an inbutyl group, a secondary butyl group, a methoxy group, an ethoxy group, a propoxy group, an inpropoxy group, a butoxy group, an inbutoxy group. group, secondary butoxy group, chlorine atom or bromine atom.
式■の反応性アゾ染料の塩としては、例えばアルカリ金
属塩特にリチウム、ナトリウム又はカリウムの塩、アル
カリ土類金属塩特にマグネシウム塩又はテトラアルキル
アンモニウム塩が用いられる。As salts of the reactive azo dyes of the formula (1), for example alkali metal salts, especially lithium, sodium or potassium salts, alkaline earth metal salts, especially magnesium salts or tetraalkylammonium salts are used.
次式
（Ｒ１はメチル基、エチル基、メトキシ基、エトキシ基
又は塩素原子、Ｒ２はＣ２〜Ｃ４−アルキル基を意味す
る）の反応性アゾ染料が好ましい。Reactive azo dyes of the following formula (R1 means methyl group, ethyl group, methoxy group, ethoxy group or chlorine atom, R2 means C2-C4-alkyl group) are preferred.
特に好ましいものは、式ＵにおいてＲ１がアゾ基に対す
るｐ−位に存在するメチル基、メトキシ基、エトキシ基
又は塩素原子であり、そしてＲ２がエチル基である反応
性アゾ染料である。Particularly preferred are reactive azo dyes of the formula U in which R1 is a methyl, methoxy, ethoxy or chlorine atom in the p-position relative to the azo group and R2 is an ethyl group.
本発明の染料は既知の方法により得られる。The dyes of the invention are obtained by known methods.
例えば置換アニリン−スルホン酸をジアゾ化し、これを
１−ヒドロキシ−８−アミノナフタリン−５，６（又は
４．６ ）−ジスルホン酸とシアヌールクロリド及び対
応するアニリン誘導体との反応により得られた縮合生成
物をカップリングさせる。For example, the condensation obtained by diazotizing a substituted aniline-sulfonic acid and reacting it with 1-hydroxy-8-aminonaphthalene-5,6 (or 4.6)-disulfonic acid, cyanuric chloride and the corresponding aniline derivative Coupling the products.
適当に置換されたアニリンスルホ／酸の例は次のもので
ある。２−アミノ−５−メチルペンゾールスルホン酸、
６−アミノ−６−メチルペンゾールスルホン酸、３−ア
ミノ−４−メチルペンゾールスルホン酸、４−アミノ−
５−メチルペンゾールスルホン酸、２−７ミノー５−二
チルペンゾールスルホン酸、３−アミノ−６−エチルペ
ンゾールスルホン酸、６〜７ミ／−４−エチルペンゾー
ルスルホン酸、４−７ミ／−５−エチルペンゾールスル
ホン酸、２−アミノ−５−メトキシペンゾールスルホン
酸、６−アミノ−４−メトキシペンゾールスルホン酸、
３−アミノ−６−メトキシペンゾールスルホン酸、２−
−アミノ−５−エトキシペンゾールスルホン酸、３−ア
ミノ−６−エトキシペンゾールスルホン酸、２−アミノ
−５−クロルベンゾールスルホン酸、４−アミノ−５−
１０ルベンゾールスルホン酸、６−アミノ−４−クロル
ベンソー／ｌ／ ス／Ｌ／ ホン酸、６−アミノ−６−
クロルベンゾールスルホン酸、２−アミノ−４−クロル
ベンゾールスルホン酸、２−アミノ−５−ブロムペンゾ
ールスルホン酸又は４−アミノ−５−ブロムペンゾール
スルホン酸。Examples of suitably substituted aniline sulfo/acids are: 2-amino-5-methylpenzole sulfonic acid,
6-amino-6-methylpenzole sulfonic acid, 3-amino-4-methylpenzole sulfonic acid, 4-amino-
5-methylpenzole sulfonic acid, 2-7 mino-5-ditylpenzole sulfonic acid, 3-amino-6-ethylpenzole sulfonic acid, 6-7 min/-4-ethylpenzole sulfonic acid, 4-7 Mi/-5-ethylpenzole sulfonic acid, 2-amino-5-methoxypenzole sulfonic acid, 6-amino-4-methoxypenzole sulfonic acid,
3-Amino-6-methoxypenzole sulfonic acid, 2-
-Amino-5-ethoxypenzole sulfonic acid, 3-amino-6-ethoxypenzole sulfonic acid, 2-amino-5-chlorobenzole sulfonic acid, 4-amino-5-
10 Rubenzole sulfonic acid, 6-amino-4-chlorobenzoic acid/l/S/L/phonic acid, 6-amino-6-
Chlorbenzole sulfonic acid, 2-amino-4-chlorobenzole sulfonic acid, 2-amino-5-brompenzole sulfonic acid or 4-amino-5-brompenzole sulfonic acid.
縮合反応用の適当なアニリン誘導体としては例えば次の
ものが用いられる。Ｎ−エチルアニリン、Ｎ−プロピル
アニリン、Ｎ−イソプロピルアニリン、Ｎ−ブチルアニ
リン、Ｎ−インブチルアニリン、Ｎ−二級ブチルアニリ
ン、Ｎ −エチル−〇−１■ｌ−又はｐ−トルイジン、
Ｎ−プロピル−〇−１ｍ−又はｐ−トルイジン、Ｎ−ブ
チル−０−１ｍ−又はｐ−トルイジン、Ｎ−エチル−ｏ
−、ｍ−又ハｐ −クロルアニリン、Ｎ −７”ロビ
ルーｏ−ｌｍ−又はｐ−クロルアニリン、Ｎ−ブチル−
０−１ｍ−又はｐ−クロルアニリン、Ｎ−エチル−〇−
１ｍ−又はｐ−アニシジン、Ｎ−エチル−０−１ｍ−又
はｐ−フェネチジン、Ｎ−（２−ヒドロキシエチル）−
アニリン、Ｎ−（２−ヒドロキシプロピル）−アニリン
、Ｎ−（２−ヒドロキシブチル）−ア＝ ！Ｊ ７又ハ
Ｎ −（２−メトキシエチル）−７＝リ ン。As suitable aniline derivatives for the condensation reaction, the following can be used, for example. N-ethylaniline, N-propylaniline, N-isopropylaniline, N-butylaniline, N-inbutylaniline, N-secondary butylaniline, N-ethyl-〇-1■l- or p-toluidine,
N-propyl-0-1m- or p-toluidine, N-butyl-0-1m- or p-toluidine, N-ethyl-o
-, m- or p-chloroaniline, N-7'' lobi-olm- or p-chloroaniline, N-butyl-
0-1m- or p-chloroaniline, N-ethyl-〇-
1m- or p-anisidine, N-ethyl-0-1m- or p-phenetidine, N-(2-hydroxyethyl)-
Aniline, N-(2-hydroxypropyl)-aniline, N-(2-hydroxybutyl)-a=! J 7mataN-(2-methoxyethyl)-7=phosphorus.
新規染料は、セルロース含有材料特に木綿の型であると
きに水溶性が優れている。これは結晶化安定な液状染料
調製物の製造に好適である。The new dye has excellent water solubility when in the form of cellulose-containing materials, especially cotton. This is suitable for producing crystallization-stable liquid dye preparations.
不発明の液状染料調製物は、式Ｉの反応性アゾ染料を５
〜６５重量％好ましくは１６〜２４ｆｆｉｆ％の量で含
有する。そのほかこれは、普通の助剤例えば緩衝物質、
水保持剤及び殺菌剤又はヒドロトロピー剤を含有しうる
。The liquid dye preparation of the invention comprises a reactive azo dye of formula I
It contains in an amount of ~65% by weight, preferably 16-24ffif%. In addition, it includes the usual auxiliaries, such as buffer substances,
It may contain water retaining agents and bactericidal or hydrotropic agents.
下記実施例中の部及び％は重量に関する。Parts and percentages in the examples below relate to weight.
実施例１
１−アミノ−８−ヒドロキシナフタリン−３，６−ジス
ルホン酸、シアヌールクロリド及びＮ−エチルアニリン
からの二次縮合生成物５５部の水性懸濁液に、０〜５℃
で２−アミノ−５−メチルペンゾールスルホン酸１８．
７部の塩酸性ジアゾ化懸濁液を添加し、炭酸ナトリウム
を用いてｐＨを５．５にする。ｐＨ５，５で６時間攪拌
したのちカップリングが終了する。次いで中性溶液から
、室温で塩化ナトリウム２００部の添加により染料を塩
析し、濾過して乾燥する。次式の染料が得られ、これは
木綿を一般、良好な堅牢性を有する透明な帯青赤色色調
に染色する。Example 1 An aqueous suspension of 55 parts of a secondary condensation product from 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid, cyanuric chloride and N-ethylaniline is added at 0-5°C.
2-Amino-5-methylpenzole sulfonic acid 18.
7 parts of the hydrochloric acidic diazotization suspension are added and the pH is brought to 5.5 using sodium carbonate. Coupling is completed after stirring at pH 5.5 for 6 hours. The dye is then salted out from the neutral solution at room temperature by adding 200 parts of sodium chloride, filtered and dried. A dyestuff of the following formula is obtained, which generally dyes cotton in clear bluish-red tones with good fastness properties.
実施例２
２−アミノ−５−メトキシ−ペンゾールスルホン酸２０
．５部を塩酸性でジアゾ化し、このジアゾ化懸濁液を０
〜５℃で、１−アミノ−８−ヒドロキシナフタリン−３
，６−ジスルホン酸、シアヌールクロリド及びＮ−エチ
ルアニリ／からの二次縮合生成物５５部の水性懸濁液に
添加する。次いで炭酸ナトリウムを添加してｐＨを５．
５となし、カップリングが終了するまで６時間保持する
。食塩２００部の添加により次式の染料を沈殿させ、濾
過して乾燥する。このものは木綿上に良好な堅牢性を有
する帯青赤色の ４濃厚な染色を与えろ。Example 2 2-amino-5-methoxy-penzole sulfonic acid 20
．． 5 parts were diazotized with hydrochloric acid, and this diazotized suspension was reduced to 0.
At ~5°C, 1-amino-8-hydroxynaphthalene-3
, 6-disulfonic acid, cyanuric chloride and N-ethylanili/ to an aqueous suspension of 55 parts. Sodium carbonate was then added to bring the pH to 5.
5 and hold for 6 hours until coupling is complete. A dye of the following formula is precipitated by addition of 200 parts of common salt, filtered and dried. This gives a deep bluish-red dyeing with good fastness on cotton.
実施例１及び２と同様にして第１表に示す染料が得られ
る。 ５第 １
表
（′］
Ｃ２Ｈ。The dyes shown in Table 1 are obtained in the same manner as in Examples 1 and 2. 5th 1st
Table ('] C2H.
２Ｈ５ ０３Ｈ ２Ｈ５ ２Ｈ５ Ｃ２Ｈ。2H5 03H 2H5 2H5 C2H.
ｃ３Ｈｔ（ｎ） ｃ４Ｈｏ（ｎ） １ 。c3Ht(n) c4Ho(n) 1.
２Ｈ５ Ｃ２Ｈ。2H5 C2H.
同様にして第２表に示す次式の染料が得られる。In the same way, dyes of the following formula shown in Table 2 are obtained.
ｒｌ
ｏ３Ｈ
ｏ３Ｈ
ｏ３Ｈ
Ｃ３Ｈフ（ｎ）
実施例２７
純粋染料を２５％含有する次式
の染料の水で湿った食塩含有プレスケーキ３０部を、水
７０部に溶解する（温度は２０〜２５℃）。次いでこの
染料溶液を２０〜２５℃の温度及び８．０のｐＨで、残
留塩素含量が０．１％以下になるまで電気透析する。脱
塩した染料溶液は８．５％の純粋染料含量を有し、これ
をＮａ２ＨＰＯ４２％（純粋染料に対し）の添加により
ｐＨを７５にする。次いで回転蒸発器により濃縮して、
溶液中の純粋染料の含量を２４％に高める。得られた染
料溶液は貯蔵安定で、６週間後も染料の沈殿を示さない
。rl o3H o3H o3H C3Hfu(n) Example 27 30 parts of a water-moist salt-containing presscake of a dye of the following formula containing 25% pure dye is dissolved in 70 parts of water (temperature 20-25°C). . The dye solution is then electrodialyzed at a temperature of 20 DEG -25 DEG C. and a pH of 8.0 until the residual chlorine content is below 0.1%. The desalted dye solution has a pure dye content of 8.5% and is brought to a pH of 75 by addition of 42% Na2HPO (relative to pure dye). It is then concentrated using a rotary evaporator.
The content of pure dye in the solution is increased to 24%. The dye solution obtained is storage stable and shows no dye precipitation even after 6 weeks.
実施例２８
純粋染料を６４％含有する次式
］
の染料の水で湿った食塩含有プレスケーキ４０部を、水
６０部に溶解する（温度は４０°Ｃ）。Example 28 40 parts of a water-moist salt-containing presscake of a dye of the following formula containing 64% pure dye are dissolved in 60 parts of water (temperature 40° C.).
次いでこの染料溶液を４０℃の温度及び８．０のｐＨで
、残留塩素含量が０．１％以下になるまで電気透析する
。脱塩した染料溶液の純粋染料含量は１６％、ｐＨ価は
８．０である。得られた染料溶液は貯蔵安定で、６週間
後も染料の沈殿を示さない。The dye solution is then electrodialyzed at a temperature of 40° C. and a pH of 8.0 until the residual chlorine content is below 0.1%. The pure dye content of the desalted dye solution is 16% and the pH value is 8.0. The dye solution obtained is storage stable and shows no dye precipitation even after 6 weeks.
実施例２９
純粋染料を４０％含有する次式
の染料の水で湿った食塩含有プレスケーキ４０部を、水
６０部に溶解しく温度は４５〜５０°Ｃ）、水酸化リチ
ウムを用いてｐＨを７．５にする。この染料溶液は純粋
染料を１６％含有し、貯蔵安定で６週間後も染料の沈殿
を示さない。Example 29 40 parts of a water-moist salt-containing presscake of a dye of the following formula containing 40% pure dye was dissolved in 60 parts of water (at a temperature of 45-50°C) and adjusted to pH using lithium hydroxide. Set it to 7.5. This dye solution contains 16% pure dye and is storage stable and shows no dye precipitation even after 6 weeks.
Claims (1)
４−アルコキシ基、塩素原子又は臭素原子、Ｒ＾２は置
換基を有しうるＣ＿２〜Ｃ＿４−アルキル基、Ｒ＾３は
水素原子、Ｃ＿１〜Ｃ＿４−アルキル基、Ｃ＿１〜Ｃ＿
４−アルコキシ基、塩素原子又は臭素原子を意味する）
で表わされる反応性アゾ染料又はその塩。 ２、次式 ▲数式、化学式、表等があります▼（II） （Ｒ＾１はメチル基、エチル基、メトキシ基、エトキシ
基又は塩素原子、Ｒ＾２はＣ＿２〜Ｃ＿４−アルキル基
を意味する）で表わされる特許請求の範囲第１項に記載
のアゾ染料。 ３、次式 ▲数式、化学式、表等があります▼（ I ） （Ｒ＾１はＣ＿１〜Ｃ＿４−アルキル基、Ｃ＿１〜Ｃ＿
４−アルコキシ基、塩素原子又は臭素原子、Ｒ＾２は置
換基を有しうるＣ＿２〜Ｃ＿４−アルキル基、Ｒ＾３は
水素原子、Ｃ＿１〜Ｃ＿４−アルキル基、Ｃ＿１〜Ｃ＿
４−アルコキシ基、塩素原子又は臭素原子を意味する）
で表わされる反応性アゾ染料又はその塩を３〜３５重量
％含有することを特徴とする、液状染料調製物。[Claims] 1. The following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) (R^1 is a C_1-C_4-alkyl group, C_1-C_
4-alkoxy group, chlorine atom or bromine atom, R^2 is a C_2-C_4-alkyl group that may have a substituent, R^3 is a hydrogen atom, C_1-C_4-alkyl group, C_1-C_
4-alkoxy group, chlorine atom or bromine atom)
A reactive azo dye or a salt thereof. 2. The following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) (R^1 means methyl group, ethyl group, methoxy group, ethoxy group or chlorine atom, R^2 means C_2-C_4-alkyl group ) The azo dye according to claim 1, which is represented by: 3. The following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) (R^1 is C_1-C_4-alkyl group, C_1-C_
4-alkoxy group, chlorine atom or bromine atom, R^2 is a C_2-C_4-alkyl group that may have a substituent, R^3 is a hydrogen atom, C_1-C_4-alkyl group, C_1-C_
4-alkoxy group, chlorine atom or bromine atom)
1. A liquid dye preparation containing 3 to 35% by weight of a reactive azo dye or a salt thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3603790.7 | 1986-02-07 | ||
| DE3603790 | 1986-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62185759A true JPS62185759A (en) | 1987-08-14 |
Family
ID=6293585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62024934A Pending JPS62185759A (en) | 1986-02-07 | 1987-02-06 | Reactive azo dye |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS62185759A (en) |
| CH (1) | CH669389A5 (en) |
| GB (1) | GB2186585A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4902786A (en) * | 1986-07-17 | 1990-02-20 | Hoechst Aktiengesellschaft | Phenylazonaphthol or naphthylazonaphthol compounds containing a fibre-reactive aminophenylamino-substituted halogen-s-triazinylamino group and a fibre-reactive group of the vinylsulfone series, suitable as dyestuffs |
| GB9204905D0 (en) * | 1992-03-06 | 1992-04-22 | Ici Plc | Compositions and compounds |
| BR9303283A (en) * | 1992-08-14 | 1994-03-08 | Sandoz Ag | COMPOUNDS AND THEIR SALTS, OR A MIXTURE OF SUCH COMPOUNDS OR SALTS; PROCESS FOR ITS PREPARATION, AND PROCESS FOR DYING OR STAMPING OF AN ORGANIC SUBSTRATE |
| CH685762A5 (en) * | 1992-09-17 | 1995-09-29 | Sandoz Ag | A fiber-reactive monoazo dyes. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB834304A (en) * | 1957-04-23 | 1960-05-04 | Ici Ltd | New monoazo dyestuffs containing triazine radicals |
| CH641197A5 (en) * | 1977-12-23 | 1984-02-15 | Sandoz Ag | REACTIVE MONOAZO DYES AND METHOD FOR THE PRODUCTION THEREOF. |
| DE2901546A1 (en) * | 1979-01-16 | 1980-07-24 | Bayer Ag | REACTIVE DYES |
| CH657144A5 (en) * | 1983-05-04 | 1986-08-15 | Ciba Geigy Ag | METHOD FOR CONVERTING HEAVY-SOLUBLE SALTS OF ANIONIC DYES AND OPTICAL BRIGHTENER INTO EASILY SOLUBLE SALTS BY MEANS OF EXCHANGING CATIONS. |
-
1987
- 1987-01-09 CH CH5287A patent/CH669389A5/de not_active IP Right Cessation
- 1987-02-06 JP JP62024934A patent/JPS62185759A/en active Pending
- 1987-02-06 GB GB08702731A patent/GB2186585A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CH669389A5 (en) | 1989-03-15 |
| GB2186585A (en) | 1987-08-19 |
| GB8702731D0 (en) | 1987-03-11 |
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