JPH0420029B2 - - Google Patents
Info
- Publication number
- JPH0420029B2 JPH0420029B2 JP5611982A JP5611982A JPH0420029B2 JP H0420029 B2 JPH0420029 B2 JP H0420029B2 JP 5611982 A JP5611982 A JP 5611982A JP 5611982 A JP5611982 A JP 5611982A JP H0420029 B2 JPH0420029 B2 JP H0420029B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- group
- dyeing
- acid
- formula
- 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
- 238000004043 dyeing Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 239000000975 dye Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 239000010985 leather Substances 0.000 claims description 4
- 125000005521 carbonamide group Chemical group 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 description 17
- -1 disazo compound Chemical class 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000002657 fibrous material Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 229920003043 Cellulose fiber Polymers 0.000 description 7
- 239000003792 electrolyte Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000004753 textile Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 2
- 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 2
- 229920001007 Nylon 4 Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 235000009120 camo Nutrition 0.000 description 2
- 235000005607 chanvre indien Nutrition 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011487 hemp Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- XPKFTIYOZUJAGA-UHFFFAOYSA-N 2,5-diethoxyaniline Chemical compound CCOC1=CC=C(OCC)C(N)=C1 XPKFTIYOZUJAGA-UHFFFAOYSA-N 0.000 description 1
- XBPUVFXYMVKHHE-UHFFFAOYSA-N 4-ethenylsulfonyl-2,5-dimethoxyaniline Chemical compound COC1=CC(S(=O)(=O)C=C)=C(OC)C=C1N XBPUVFXYMVKHHE-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 206010033546 Pallor Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/513—Disazo or polyazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
【発明の詳細な説明】
本発明は、繊維反応性性質を有する水溶性アゾ
染料の工業的分野に在る。DETAILED DESCRIPTION OF THE INVENTION The present invention is in the industrial field of water-soluble azo dyes with fiber-reactive properties.
本発明により一般式(1)
を有する、新規な価値ある水溶性ジスアゾ化合物
が見い出された。上記式(1)中Ｍは水素原子又は金
属例えばアルカリ金属又はアルカリ土類金属例え
ばナトリウム、カリウム及びカルシウムの当量を
意味し、両方の式残量Ｘは相互に同一か又は相互
に異なつた意味を有しそして夫々Ｘはビニル基又
はβ−スルフアトエチル−基（Ｍが上記の意味を
有する式−CH2−CH2−OSO3Mに相当する）又
はβ−チオスルフアトエチル−基（Ｍが上記の意
味を有する式−CH2−CH2−Ｓ−SO3Mに相当す
る）を示しそしてＲは夫々エトキシ−殊にメトキ
シ基である。 According to the present invention, the general formula (1) A new and valuable water-soluble disazo compound has been discovered. In the above formula (1), M means a hydrogen atom or an equivalent of a metal such as an alkali metal or an alkaline earth metal such as sodium, potassium, and calcium, and the remaining amounts X in both formulas have the same or different meanings. and , respectively , (corresponding to the formula -CH 2 -CH 2 -S-SO 3 M) with the abovementioned meaning and R is in each case an ethoxy, especially methoxy, group.
本発明による新規なジスアゾ化合物は酸性形態
でもその塩の形態でも在ることができる。これは
塩特にアルカリー及びアルカリ土類金属塩の形態
であるのが好ましくそして又これらの塩の形態で
ヒドロキシー又はカルボンアミド基含有繊維又は
皮革の染色又は捺染に使用するのが好ましい。 The novel disazo compounds according to the invention can exist both in acidic form and in the form of their salts. It is preferably in the form of salts, especially alkali and alkaline earth metal salts, and is also preferably used in the form of these salts for dyeing or printing hydroxy- or carbonamide group-containing fibers or leather.
式(1)の新規化合物は式（遊離酸の形で記載し
て）
に相当する類似構造の公知染料に比較して驚くべ
き程特にその中間薄暮（Abendfarbe）色で優れ
ている。 The new compound of formula (1) has the formula (written in free acid form) Compared to known dyes of similar structure, it is surprisingly superior, especially in its mid-twilight color.
本発明の一般式(1)の上記ジスアゾ化合物は、先
づ一般式(2)
（式中Ｘは上記の意味を有する）の芳香族アミン
をジアゾ化しそして一般式(3)
（式中Ｍは上記の意味を有する）の化合物と強酸
性媒体好ましくは水性媒体中で殊に０乃至2.5の
PH−値でカツプリングし、次に形成された一般式
(4)
（式中Ｍ及びＸは上記の意味を有する）のこのモ
ノアゾ化合物を弱酸性乃至弱アルカリ性媒体好ま
しくは水性媒体中で殊に４乃至７のPH−値で一般
式(5)
（式中Ｒ及びＸは上記の意味を有する）の芳香族
アミンのジアゾ化物とカツプリングすることによ
り得られる。 The above-mentioned disazo compound of the general formula (1) of the present invention is first synthesized by the general formula (2). (wherein X has the above meaning) is diazotized and the aromatic amine of the general formula (3) (wherein M has the above-mentioned meaning) in a strongly acidic medium, preferably an aqueous medium, and especially 0 to 2.5
Coupling with PH− value, then the general formula formed
(Four) This monoazo compound (wherein M and It can be obtained by coupling with a diazotized aromatic amine (wherein R and X have the above meanings).
芳香族アミン(2)及び(5)のジアゾ化は通常の公知
方法で例えば塩酸水性媒体中で亜硝酸ナトリウム
により−５℃乃至＋15℃の温度で行われる。同様
に両カツプリング反応はそれ自体公知の方法で実
施される。第一段階のカツプリング反応は強酸性
範囲でそして殊に５乃至30℃の温度で行われる。
第二段階のカツプリング反応は殊に弱酸性乃至中
性範囲でそして殊に５乃至30℃の温度で行われ
る。 The diazotization of the aromatic amines (2) and (5) is carried out in customary known manner, for example with sodium nitrite in an aqueous hydrochloric medium at temperatures of -5 DEG C. to +15 DEG C. Both coupling reactions are likewise carried out in a manner known per se. The first stage coupling reaction is carried out in the strongly acidic range and in particular at temperatures of 5 to 30°C.
The second stage coupling reaction is carried out in particular in a weakly acidic to neutral range and in particular at a temperature of 5 to 30°C.
第二カツプリング反応の際のPH−範囲の調整の
ための酸結合剤として好ましくは弱無機又は有機
酸例えば炭酸、酢酸、硼酸、蓚酸のアルカリ−又
はアルカリ土類金属塩又は燐酸の酸性塩が使用さ
れる。特にこのために炭酸ナトリウム及び−カリ
ウム、酢酸ナトリウム、硼酸ナトリウム及び殊に
有利には炭酸水素ナトリウムが適する。 As acid binders for adjusting the pH range in the second coupling reaction, weak inorganic or organic acids such as alkali or alkaline earth metal salts of carbonic acid, acetic acid, boric acid, oxalic acid or acid salts of phosphoric acid are preferably used. be done. Particularly suitable for this purpose are sodium and potassium carbonate, sodium acetate, sodium borate and particularly preferably sodium hydrogen carbonate.
一般式(1)−式中Ｘがβ−スルフアトエチル基を
示す−の本発明による化合物は又、上記の方法で
一般式(2)及び(5)−式中但し両式残基Ｘの一方又は
両式残基Ｘがβ−ヒドロキシエチル基を示す−の
芳香族アミンの一方又は両方を式(3)の１−アミノ
−８−ナフトール−３，６−ジスルホン酸とカツ
プリングしそしてこの様にして製造した、一般式
(1)−式中但し両Ｘの一方又は両方がβ−ヒドロキ
シエチル基を示す−の構造を有するジスアゾ化合
物をそれ自体公知の方法で硫酸化剤例えば濃硫酸
又はクロルスルホン酸で式(1)に相当する本発明に
よるスルフアト化合物に変える様にして製造する
ことができる。 Compounds according to the invention of the general formula (1), in which X represents a β-sulfatoethyl group, can also be prepared by the above method in the general formulas (2) and (5), with the proviso that one or both of the residues X One or both of the aromatic amines of formula (3) in which both residues X represent a β-hydroxyethyl group are coupled with 1-amino-8-naphthol-3,6-disulfonic acid of formula (3), and in this way Manufactured, general formula
A disazo compound having the structure (1) - in which one or both of X's represents a β-hydroxyethyl group - is converted into the formula (1) using a sulfating agent such as concentrated sulfuric acid or chlorosulfonic acid by a method known per se. The sulfate compounds according to the invention corresponding to .
本発明による化合物はその合成混合物からその
製造後水溶性化合物に就て一般的に公知な方法に
より、例えば電解質例えば塩化ナトリウム又は塩
化カリウムによる反応媒体からの沈殿、引き続い
てのろ過により又は併し反応溶液自体の蒸発例え
ば噴霧乾燥により、単離することができる。本発
明による化合物の単離の前記方法が選択される場
合、反応溶液が多量の硫酸塩を含有する場合蒸発
前溶液中に存在する硫酸塩を硫酸カルシウムとし
て沈澱させそしてろ過による分離により除去する
ことが推奨される。多くの場合又式(1)のこの化合
物を含有する反応溶液を、場合により濃縮及び／
又は緩衝物質の添加後、直接液体調合物として染
色的用途に供給することが望ましい。 The compounds according to the invention can be obtained from the synthesis mixture by methods generally known for water-soluble compounds, for example by precipitation from the reaction medium with an electrolyte such as sodium chloride or potassium chloride, followed by filtration or by simultaneous reaction. It can be isolated by evaporation of the solution itself, for example by spray drying. If said method of isolation of compounds according to the invention is chosen, if the reaction solution contains large amounts of sulfate, the sulfate present in the solution before evaporation is precipitated as calcium sulfate and removed by separation by filtration. is recommended. In many cases, the reaction solution containing this compound of formula (1) is also optionally concentrated and/or
Alternatively, after addition of buffer substances, it may be desirable to supply the dye directly as a liquid preparation for dyeing applications.
本発明の新規化合物はヒドロキシー又はカルボ
ンアミド基含有繊維からなる材料又は皮革例えば
天然又は再生セルロース又は天然、再生又は合成
ポリアミドからなる繊維材料例えば木綿、***、
麻、ジユート、ビスコース人絹、羊毛、絹、ポリ
アミド−６、ポリアミド６，６、ポリアミド−11
及びポリアミド−４を染色又は捺染するための染
料特に繊維反応染料として特に適する。殊に該新
規化合物はセルロース繊維材料の染色又は捺染に
適する。 The novel compounds of the present invention are suitable for use in materials or leathers made of fibers containing hydroxyl or carbonamide groups, such as natural or regenerated cellulose or fiber materials made of natural, regenerated or synthetic polyamides, such as cotton, hemp,
Hemp, jute, viscose human silk, wool, silk, polyamide-6, polyamide 6,6, polyamide-11
It is particularly suitable as a dye, especially a fiber-reactive dye, for dyeing or printing polyamide-4 and polyamide-4. In particular, the novel compounds are suitable for dyeing or printing cellulose fiber materials.
該新規化合物は、上記の基体上で水溶性特に繊
維反応性染料に就て公知の及び通常の染色−及び
捺染法に類似して適用及び固着される。これは高
い着色力及び均染性及び非常に良好な堅牢性を有
する帯縁黒色染色及び捺染を与える。堅牢性のう
ち日光堅牢性、洗たく堅牢性、アルカリ性及び酸
性汗堅牢性、アイロン掛け−、ひだ付け−及び湯
通し堅牢性、溶剤−及びドライクリーニング堅牢
性、水及び海水堅牢性、塩素浴水堅牢性及び酸−
及びアルカリ堅牢性が殊に強調される。 The novel compounds are applied and fixed on the abovementioned substrates analogously to the known and customary dyeing and printing processes for water-soluble, in particular fiber-reactive dyes. This gives edge black dyeings and prints with high tinting strength and leveling properties and very good fastness properties. Fastness to sunlight, fastness to washing, fastness to alkaline and acid perspiration, fastness to ironing, pleating and blanching, fastness to solvents and dry cleaning, fastness to water and seawater, fastness to chlorine bath water and acid-
and alkali fastness are particularly emphasized.
それ改本発明は更に本発明による化合物を上記
の繊維材料又は皮革の染色又は捺染に使用するこ
と又は、本発明による化合物を染色及び捺染産業
の公知及び通常の方法に類似して繊維材料上に適
用しそして引き続いて固着する、上記繊維材料又
は皮革の染色又は捺染法に関する。例えばこの方
法は、セルロース繊維材料を場合により通常の染
色助剤を含有する水性浴中で吸尽法により長浴か
らアルカリ作用性剤の使用下特に60乃至105℃の
温度で処理する様にして実施され、その際繊維材
料は非常に良好な染色収率で染色される。 The invention furthermore provides the use of the compounds according to the invention for the dyeing or printing of textile materials or leather as defined above or the application of the compounds according to the invention to textile materials analogous to the known and customary methods of the dyeing and printing industry. It relates to a process for dyeing or printing textile materials or leather as described above, applying and subsequently fixing. For example, the process comprises treating the cellulosic fiber material by the exhaustion method in an aqueous bath, optionally containing customary dyeing aids, from a long bath with the use of alkaline-acting agents, especially at temperatures between 60 and 105°C. The fiber material is dyed with very good dyeing yields.
工業的に公知及び通常であるパジング法により
セルロース繊維材料上で同様に優れた染色収率で
染色が得られ、この方法は一−又は二相法で実施
することができるので、固着はアルカリ作用性剤
−これは染料の適用と同時又は該適用の後で繊維
材料上に適用する−を用いて又はパジングした繊
維材料を５分間乃至20時間室温又は60℃までの温
度で滞留させて又は蒸熱により又は乾燥による処
理により実施することができる。固着していない
染料分は容易に洗出できる。 Dyeings are obtained on cellulose fiber materials with equally good dyeing yields by the padding method, which is known and customary in industry, and which can be carried out in a one- or two-phase manner, so that fixation is dependent on the alkaline action. The padded textile material is treated with a sexing agent - which is applied on the textile material at the same time as or after the application of the dye - or by leaving the padded textile material for 5 minutes to 20 hours at room temperature or at temperatures up to 60°C or by steaming. It can be carried out by treatment by or by drying. Unfixed dye can be easily washed out.
本発明による化合物を捺染法で使用することは
公知及び通常の捺染−及び固着法（セルロース繊
維を染色するための）に類似して行われる。この
場合殊に一相法で捺染ペースト中に重炭酸ナトリ
ウム又は他の酸結合剤例えば重炭酸カリウム、炭
酸ナトリウム又は−カリウム、苛性ソーダ液、苛
性カリ液又はトリクロル酢酸ナトリウムを存在さ
せての捺染ペースト中でそして引き続いての101
乃至103℃での蒸熱により又は二相法で中性又は
弱酸性捺染ペーストによる捺染及び引き続いて
の、熱い電解質含有アルカリ性浴による固着又は
アルカリ性、電解質含有処理液によるオーバーパ
ジング及び引き続いての滞留、蒸熱又は乾燥処理
による固着を行う様にして該方法を実施すること
ができる。輪郭の良好な水準及びさえた白色下地
を有する着色力のよい捺染が得られる。捺染は固
着条件に関係なく一定した色調を示す。 The use of the compounds according to the invention in printing processes takes place analogously to known and customary printing and fixing processes (for dyeing cellulose fibers). In this case, in particular in a one-phase process in the printing paste in the presence of sodium bicarbonate or other acid binders such as potassium bicarbonate, sodium carbonate or -potassium, caustic soda, caustic potash or sodium trichloroacetate. And then 101
printing with neutral or weakly acidic printing pastes by steaming at up to 103° C. or in a two-phase process and subsequent fixation with hot electrolyte-containing alkaline baths or overpadding with alkaline, electrolyte-containing treatment liquids and subsequent retention; The method can be carried out in such a way that the fixation is carried out by steaming or drying treatment. A print with good tinting strength and a good level of outline and a uniform white base is obtained. The print exhibits a constant color tone regardless of fixing conditions.
ポリアミド−又はポリウレタン繊維の染色は通
常酸性環境から実施される。所望のPH−値を保つ
ために例えば染浴に酢酸又は酢酸及び酢酸アンモ
ニウムからなる緩衝剤を添加することができる。
染色の使用可能な均染性を達成する目的で通常の
均染剤の添加が推奨される。染色は沸とう温度で
も110乃至120℃でも実施することができる。染色
を仕上げるためにアンモニアによる後処理が有利
であることができる。 The dyeing of polyamide or polyurethane fibers is usually carried out from an acidic environment. To maintain the desired pH value, for example, acetic acid or a buffer consisting of acetic acid and ammonium acetate can be added to the dyebath.
In order to achieve usable leveling properties of the dyeing, the addition of conventional leveling agents is recommended. Dyeing can be carried out both at boiling temperature and at 110-120°C. Post-treatment with ammonia can be advantageous to finish the dyeing.
次の例により本発明を説明する。特記しない限
り、そこに記載の部は重量部であり、百分率の記
載は重量％に関する。容量部と重量部との関係は
リツトル対キログラムである。 The invention is illustrated by the following example. Unless otherwise stated, the parts mentioned therein are parts by weight and the percentages mentioned relate to % by weight. The relationship between parts by volume and parts by weight is liters to kilograms.
例 １
水200部中に４−β−スルフアトエチルスルホ
ニル−アニリン200部を含むPH5.0乃至5.5の水性
溶液に氷240部及び31％塩酸155部を加える。アニ
リン化合物を40％水性亜硝酸ナトリウム溶液94.5
容量部の添加により40分以内に０℃乃至５℃の温
度でジアゾ化する。なお１数時間５乃至８℃で引
き続き撹拌しそして小過剰の亜硝酸を小量のアミ
ドスルホン酸の添加により分解する。このジアゾ
ニウム塩溶液に１−アミノ−８−ヒドロキシ−ナ
フタリン−３，６−ジスルホン酸227部を撤入す
る。その後混合物のPH−値は約1.5である。16時
間15乃至19℃で引き続き撹拌し、次に炭酸ナトリ
ウム78部により6.3乃至6.8のPH−値に調整する。Example 1 To an aqueous solution of 200 parts of 4-β-sulfatoethylsulfonyl-aniline in 200 parts of water at pH 5.0 to 5.5 are added 240 parts of ice and 155 parts of 31% hydrochloric acid. Aniline compound in 40% aqueous sodium nitrite solution 94.5
Addition of parts by volume results in diazotization within 40 minutes at a temperature of 0°C to 5°C. Stirring is continued for several hours at 5-8 DEG C. and the small excess of nitrous acid is destroyed by addition of a small amount of amidosulfonic acid. 227 parts of 1-amino-8-hydroxy-naphthalene-3,6-disulfonic acid are introduced into the diazonium salt solution. The pH value of the mixture is then approximately 1.5. Stirring is continued for 16 hours at 15 DEG to 19 DEG C. and then a pH value of 6.3 to 6.8 is adjusted with 78 parts of sodium carbonate.
モノアゾ化合物のこの殆んど中性の懸濁液に次
に撹拌下ジアゾニウム塩溶液−これは常法で４−
β−スルフアトエチルスルホニル−２，５−ジメ
トキシ−アニリン243部から製造し、その後重炭
酸ナトリウムで5.3乃至5.8のPH−値に調整してあ
る−を加える。この反応混合物を数時間5.8乃至
6.3のPH−値及び15乃至18℃の温度で引き続き撹
拌する。けいそう土10部の添加後反応溶液を清澄
にしそしてろ液を減圧下60℃で蒸発乾固する。磨
砕後式
の化合物710部を含有する黒色の電解質含有（主
として塩化ナトリウム）粉末が得られる。この化
合物は染料としてすばらしく適しそしてアルカリ
性に作用する剤の存在下繊維反応性染料にとつて
通常な染色−及び捺染法によりセルロース繊維材
料を高い製造−及び使用堅牢性を有する帯縁黒色
色調で染色する。 This nearly neutral suspension of monoazo compound is then added with a stirred diazonium salt solution, which is prepared in a conventional manner.
Prepared from 243 parts of β-sulfatoethylsulfonyl-2,5-dimethoxy-aniline, which was then adjusted to a pH value of 5.3 to 5.8 with sodium bicarbonate, is added. This reaction mixture was heated for several hours.
Continue stirring at a pH value of 6.3 and a temperature of 15-18°C. After addition of 10 parts of diatomaceous earth, the reaction solution is clarified and the filtrate is evaporated to dryness under reduced pressure at 60°C. Post-grinding ceremony A black electrolyte-containing (mainly sodium chloride) powder is obtained containing 710 parts of the compound. This compound is excellently suited as a dye and can be used to dye cellulose fiber materials by the customary dyeing and printing processes for fiber-reactive dyes in the presence of alkaline-acting agents in a band-black tone with high production and use fastness. do.
例 ２
例１に記載した方法で実施するが、但しそこで
使用した４−β−スルフアトエチルスルホニルー
２，５−ジメトキシ−アニリンを４−ビニルスル
ホニル−２，５−ジメトキシ−アニリン173部に
換える。式
の化合物630部を含有する黒色、電解質含有粉末
が得られる。これは同様に非常に良好な染料性質
を有しそしてセルロース繊維材料上で高い製造−
及び使用堅牢性を有する帯縁黒色染色を与える。
例２のこのジスアゾ化合物の性質は例１のジスア
ゾ化合物のそれと実際上同一である。Example 2 The procedure described in Example 1 is carried out, except that the 4-β-sulfatoethylsulfonyl-2,5-dimethoxy-aniline used therein is replaced with 173 parts of 4-vinylsulfonyl-2,5-dimethoxy-aniline. exchange. formula A black, electrolyte-containing powder is obtained containing 630 parts of the compound. It also has very good dye properties and high production on cellulose fiber materials.
Gives a banded black dyeing with fastness and use fastness.
The properties of this disazo compound of Example 2 are virtually identical to those of the disazo compound of Example 1.
例 ３
水200部中に４−β−スルフアトエチルスルホ
ニル−アニリン200部を含むPH5.0乃至5.5のPHを
有する水性溶液に氷240部及び31％塩酸155部を加
え、アニリン化合物を40％水性亜硝酸ナトリウム
溶液94.5容量部の添加により40分以内に０℃乃至
５℃の温度でジアゾ化する。混合物をなお数時間
５乃至８℃で引き続き撹拌しそして小過剰の亜硝
酸を小量のアミドスルホン酸の添加により分解す
る。このジアゾニウム塩溶液に１−アミノ−８−
ヒドロキシ−ナフタリン−３，６−ジスルホン酸
227部を撒入し、その後混合物のPH−値は約1.5で
ある。なお16時間15乃至19℃で引き続き撹拌し、
次に炭酸ナトリウム78部により6.3乃至6.8のPH−
値に調整する。Example 3 To an aqueous solution containing 200 parts of 4-β-sulfatoethylsulfonyl-aniline in 200 parts of water and having a pH of 5.0 to 5.5, 240 parts of ice and 155 parts of 31% hydrochloric acid were added, and 40 parts of the aniline compound was added. Diazotization takes place within 40 minutes at a temperature of 0 DEG C. to 5 DEG C. by adding 94.5 parts by volume of % aqueous sodium nitrite solution. The mixture is continued to be stirred for several hours at 5-8° C. and the small excess of nitrous acid is destroyed by addition of a small amount of amidosulfonic acid. This diazonium salt solution contains 1-amino-8-
Hydroxy-naphthalene-3,6-disulfonic acid
227 parts are added, after which the pH value of the mixture is approximately 1.5. Continue stirring at 15 to 19°C for 16 hours.
Then add 78 parts of sodium carbonate to a pH of 6.3 to 6.8.
Adjust to value.
この様に得られる、モノアゾ化合物の殆んど中
性の懸濁液に撹拌下ジアゾニウム塩溶液−これは
常法で４−β−スルフアトエチルスルホニル−
２，５−ジエトキシ−アニリン266部から製造し、
その後重炭酸ナトリウムで5.5乃至5.8のPH−値に
調整してある−を加える。この反応混合物を数時
間5.3乃至6.3のPH−値及び15乃至18℃の温度で引
き続き撹拌する。けいそう土10部の添加後反応溶
液を清澄にしそしてろ液を減圧下60℃で蒸発乾固
する。生成物を磨砕し、
で示される化合物の電解質含有（主として塩化ナ
トリウム）黒色粉末が得られ、これは非常に良好
な染料特性を有しそしてアルカリ性に作用する剤
の存在下繊維反応性染料にとつて通常な染色−及
び捺染法によりセルロース繊維材料を高い製造−
及び使用堅牢性を有する帯縁黒色色調で染色す
る。 The almost neutral suspension of the monoazo compound thus obtained is added with a stirred diazonium salt solution to 4-β-sulfatoethylsulfonyl-
Produced from 266 parts of 2,5-diethoxy-aniline,
Then add sodium bicarbonate to a pH value of 5.5 to 5.8. The reaction mixture is subsequently stirred for several hours at a pH value of 5.3 to 6.3 and a temperature of 15 to 18 DEG C. After addition of 10 parts of diatomaceous earth, the reaction solution is clarified and the filtrate is evaporated to dryness under reduced pressure at 60°C. Grind the product; An electrolyte-containing (mainly sodium chloride) black powder of the compound of High-quality production of cellulose fiber materials using the printing method
Dyeing with a band edge black tone with fastness and use.
例 ４
水200g部中に４−β−スルフアトエチルスル
ホニル−アニリン200部を含むPH5.0乃至5.5のPH
を有する水溶液に氷240部及び31％塩酸155部を加
え、アニリン化合物を40％水性亜硝酸ナトリウム
溶液94.5容量部の添加により40分以内に０℃乃至
５℃の温度でジアゾ化する。混合物をなお数時間
５乃至８℃で引き続き撹拌しそして小過剰の亜硝
酸を小量のアミドスルホン酸の添加により分解す
る。このジアゾニウム塩溶液に１−アミノ−８−
ヒドロキシ−ナフタリン−３，６−ジスルホン酸
227部を撒入し、その後混合物のPH−値は約1.5で
ある。なお16時間15乃至19℃で引き続き撹拌し、
次に炭酸ナトリウム78部により6.3乃至6.8のPH−
値に調整する。Example 4 PH of 5.0 to 5.5 containing 200 parts of 4-β-sulfatoethylsulfonyl-aniline in 200 g of water
240 parts of ice and 155 parts of 31% hydrochloric acid are added to the aqueous solution containing 240 parts of ice and the aniline compound is diazotized within 40 minutes at a temperature of 0° C. to 5° C. by addition of 94.5 parts by volume of 40% aqueous sodium nitrite solution. The mixture is continued to be stirred for several hours at 5-8° C. and the small excess of nitrous acid is destroyed by addition of a small amount of amidosulfonic acid. This diazonium salt solution contains 1-amino-8-
Hydroxy-naphthalene-3,6-disulfonic acid
227 parts are added, after which the pH value of the mixture is approximately 1.5. Continue stirring at 15 to 19°C for 16 hours.
Then add 78 parts of sodium carbonate to a pH of 6.3 to 6.8.
Adjust to value.
この様に得られる、モノアゾ化合物の殆んど中
性の懸濁液に撹拌下ジアゾニウム塩溶液−これは
常法で４−ビニルスルホニル−2.5−ジエトキシ
−アニリン193部から製造し、その後重炭酸ナト
リウムで5.5乃至5.8のPH−値に調整してある。−
を加える。この反応混合物を数時間5.3乃至6.3の
PH−値及び15乃至18℃の温度で引き続き撹拌す
る。けいそう土10部の添加後反応溶液を清澄にし
そしてろ液を減圧下60℃で蒸発乾固する。生成物
を磨砕し、
で示される化合物の電解質含有（主として塩化ナ
トリウム）黒色粉末が得られ、これは非常に良好
な染料特性を有しそしてアルカリ性に作用する剤
の存在下繊維反応性染料にとつて通常な染色−及
び捺染法によりセルロース繊維材料を高い製造−
及び使用堅牢性を有する帯縁黒色色調で染色す
る。 To the almost neutral suspension of the monoazo compound thus obtained is added a stirred solution of the diazonium salt, which is prepared in the conventional manner from 193 parts of 4-vinylsulfonyl-2,5-diethoxy-aniline, followed by sodium bicarbonate. The pH value was adjusted to 5.5 to 5.8. −
Add. The reaction mixture was heated for several hours at 5.3 to 6.3
Continue stirring at a pH value of 15 to 18 DEG C. After addition of 10 parts of diatomaceous earth, the reaction solution is clarified and the filtrate is evaporated to dryness under reduced pressure at 60°C. Grind the product; An electrolyte-containing (mainly sodium chloride) black powder of the compound of High-quality production of cellulose fiber materials using the printing method
Dyeing with a band edge black tone with fastness and use.
Claims (1)
両方のＸは相互に同一か又は相互に異つておりそ
して夫々Ｘはビニル基、β−スルフアトエチル基
又はβ−チオスルフアトエチル基を意味し、そし
てＲはメトキシ−又はエトキシ基を示す） で示されるジスアゾ化合物。 ２ 一般式(1) （式中、Ｍは水素原子又は金属の当量を意味し、
両方のＸは相互に同一か又は相互に異つておりそ
して夫々Ｘはビニル基、β−スルフアトエチル基
又はβ−チオスルフアトエチル基を意味し、そし
てＲはメトキシ−又はエトキシ基を示す） で示されるジスアゾ化合物を染料として使用する
方法。 ３ ヒドロキシ−又はカルボンアミド基含有繊維
からなる材料又は皮革の染色又は捺染に使用す
る、特許請求の範囲第２項記載の方法。[Claims] 1 General formula (1) (In the formula, M means a hydrogen atom or a metal equivalent,
both X's are the same as each other or different from each other, and each X is a vinyl group, a β-sulfatoethyl group or a β-thiosulfatoethyl group, and R is a methoxy- or ethoxy group). Disazo compounds shown. 2 General formula (1) (In the formula, M means a hydrogen atom or a metal equivalent,
both X's are the same as each other or different from each other, and each X is a vinyl group, a β-sulfatoethyl group or a β-thiosulfatoethyl group, and R is a methoxy- or ethoxy group). A method of using the indicated disazo compounds as dyes. 3. The method according to claim 2, which is used for dyeing or printing materials or leather made of hydroxy- or carbonamide group-containing fibers.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3113989.2 | 1981-04-07 | ||
| DE19813113989 DE3113989A1 (en) | 1981-04-07 | 1981-04-07 | Water-soluble disazo compounds, preparation thereof and use thereof as dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5887155A JPS5887155A (en) | 1983-05-24 |
| JPH0420029B2 true JPH0420029B2 (en) | 1992-03-31 |
Family
ID=6129561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5611982A Granted JPS5887155A (en) | 1981-04-07 | 1982-04-06 | Water-soluble disazo compound, manufacture and use as dye |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5887155A (en) |
| DE (1) | DE3113989A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3801997A1 (en) * | 1988-01-23 | 1989-07-27 | Hoechst Ag | WATER-SOLUBLE DISAZO COMPOUNDS, METHOD FOR THEIR PRODUCTION AND THEIR USE AS DYES |
| US5989298A (en) * | 1997-04-07 | 1999-11-23 | Ciba Speciality Chemicals Corporation | Mixtures of reactive dyes and their use |
| DE59903513D1 (en) * | 1998-06-30 | 2003-01-09 | Ciba Sc Holding Ag | Mixtures of reactive dyes and their use |
| EP2739688A1 (en) | 2011-08-04 | 2014-06-11 | Huntsman Advanced Materials (Switzerland) GmbH | Mixtures of reactive dyes and their use |
| CN102516808B (en) * | 2011-10-28 | 2013-08-28 | 浙江瑞华化工有限公司 | Synthetic method of active black dye |
-
1981
- 1981-04-07 DE DE19813113989 patent/DE3113989A1/en not_active Withdrawn
-
1982
- 1982-04-06 JP JP5611982A patent/JPS5887155A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5887155A (en) | 1983-05-24 |
| DE3113989A1 (en) | 1982-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4171081B2 (en) | Reactive dye and method for producing the same | |
| JPH0124827B2 (en) | ||
| JPH0513993B2 (en) | ||
| JPH041031B2 (en) | ||
| JP2007119788A (en) | Mixture of black fiber-reactive azo dye and method of using mixture to dye hydroxy-and/or carboxyamido-containing fibrous material | |
| JPH0239545B2 (en) | ||
| JPH0126619B2 (en) | ||
| JPH0410508B2 (en) | ||
| JPS59120656A (en) | Reactive dye and manufacture | |
| JPH0124826B2 (en) | ||
| JPH029058B2 (en) | ||
| JPH0424392B2 (en) | ||
| JPS59115362A (en) | Water-soluble naphthylazonaphthol compound, manufacture and use as dye | |
| KR880001319B1 (en) | Processes for the preparation of anthraquinone compound | |
| JPH0420029B2 (en) | ||
| KR930009243B1 (en) | Process for the preparation of water soluble pyridone-monoazo compounds | |
| JP2667366B2 (en) | Water-soluble azo compound and use of the compound as dye | |
| JP3046113B2 (en) | Reactive dye, method for producing the same and method for dyeing the material | |
| JPS62164765A (en) | Monoazo compound and method for dyeing or printing fibrous material by using same | |
| EP0219080B1 (en) | Water soluble disazo compounds, process for their preparation and their use as dyestuffs | |
| JP2004504470A (en) | Fiber-reactive monoazo dyes, methods for their preparation and their use for dyeing hydroxy- and / or carboxamide-containing fibrous materials | |
| KR890001784B1 (en) | Process for the manufacture of monoazo compounds | |
| JP2000319537A (en) | Blue dye mixture containing fiber-reactive copper complex formazan dye | |
| JPH01167373A (en) | 2-hydroxy-pyrridone-azo compound, its production and use thereof as dye | |
| KR20030010596A (en) | Dye mixture of water-soluble fiber-reactive azo dyes, method for the production and use thereof |