JPS5945701B2 - 4,4↑Water-soluble azo dye derived from 1-diaminobenzanilide - Google Patents
4,4↑Water-soluble azo dye derived from 1-diaminobenzanilideInfo
- Publication number
- JPS5945701B2 JPS5945701B2 JP6931283A JP6931283A JPS5945701B2 JP S5945701 B2 JPS5945701 B2 JP S5945701B2 JP 6931283 A JP6931283 A JP 6931283A JP 6931283 A JP6931283 A JP 6931283A JP S5945701 B2 JPS5945701 B2 JP S5945701B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- water
- azo dye
- diaminobenzanilide
- soluble azo
- 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
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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/64—Higher polyazo dyes, e.g. of the types
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
- C09B35/467—D being derived from diaminodiaryl linked through CON<, SO2N<, CSN<
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Polymerization Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は、亜麻、再生セルロース繊維、麻、大麻、黄麻
のような綿及び再生セルロース繊維や、さらには天然及
び合成ポリアミド系繊維並びにこれらの繊維の配合物、
皮革及びその他の類似材料を直接染色するのに適した一
連の新規なスルホン化アゾ染料に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to cotton and regenerated cellulose fibers such as flax, regenerated cellulose fibers, hemp, hemp, jute, as well as natural and synthetic polyamide fibers and blends of these fibers,
A series of new sulfonated azo dyes suitable for direct dyeing of leather and other similar materials.
本発明の目的は、次の一般式１）
を有する水溶性アゾ染料の製造法を提供することである
。An object of the present invention is to provide a method for producing a water-soluble azo dye having the following general formula 1).
上記の直接染料は、ベンジジン系の従来の直接染料の適
用特性と類似の特性を示すが、しかしそれらの製造の過
程で何らの特別の毒物学上の危険を伴なわない。The above-mentioned direct dyes exhibit application properties similar to those of conventional direct dyes of the benzidine series, but do not involve any special toxicological risks in the process of their preparation.
事実、本発明の染料の構造と類似の構造を有する染料を
製造するために利用されるベンジジン及びその誘導体は
、その発がん性作用のために危険な化合物であつて、そ
の結果、これらの使用及び製造は厳格な衛生上及び安全
上の基準値を要求する。In fact, benzidine and its derivatives utilized to produce dyes with a structure similar to that of the dyes of the present invention are dangerous compounds due to their carcinogenic effects and, as a result, their use and Manufacturing requires strict hygiene and safety standards.
一般式（１）を有する直接染料は、業界で既知の方法に
類似の方法により製造し得る。Direct dyes having general formula (1) can be produced by methods analogous to those known in the industry.
これらの染料は、セルロース系繊維及び含窒素系繊維並
びに皮革を緑から褐色までの暗色系の色に染色させる。These dyes dye cellulosic fibers, nitrogen-containing fibers, and leather in dark colors ranging from green to brown.
一般式（１）の染料の朱色作業は、直接ベンジジン系染
料に使用される場合と同じ方法に従つて、即ち、適量の
染料及び５〜２０％（繊維の重量に関して）の無水Ｎａ
，ｓＯ４又はＮａＣｌを含有する水浴中で一般に５０〜
１００℃の間の温度で行なわれる。The vermilion operation of the dye of general formula (1) follows the same method as used for direct benzidine dyes, i.e. with an appropriate amount of dye and 5-20% (with respect to the weight of the fiber) anhydrous Na.
, sO4 or NaCl in a water bath containing generally 50~
It is carried out at temperatures between 100°C.
下記の例は、本発明を例示するために示すものであつて
、それを制限するものではない。The following examples are given to illustrate the invention without limiting it.
「部」は、特に示していなければ、重量として表わされ
ているものと理解されたい。"Parts" are to be understood as being expressed as weight, unless otherwise indicated.
例１ ジアゾ−モノアゾ体を下記のように製造した。Example 1 The diazo-monoazo compound was prepared as follows.
１００部の水と５２部の２０よＢｅ２（３２．１４重量
（Ｆ６）塩酸中に懸濁させた２２．７部の４，４′−ジ
アミノベンズアニリドを１００部の氷で冷却した後、こ
れにＯ〜５℃において、１４部のＮａＮＯ２を６０部の
水に溶解してなる溶液を滴下することによつてテトラゾ
化した。After cooling with 100 parts of ice, 22.7 parts of 4,4'-diaminobenzanilide suspended in 100 parts of water and 52 parts of 20-Be2 (32.14 weight (F6) hydrochloric acid) Tetrazotization was carried out by dropping a solution of 14 parts of NaNO2 in 60 parts of water at 0 to 5°C.
６０分間攪拌した後、過剰の亜硝酸スルフアミン酸によ
り除去した。After stirring for 60 minutes, it was removed with excess nitrous sulfamic acid.
１５部のサリチル酸を１５０部の水と１４．６部の３６
のＢｅ”（３０．３０重量％）ＮａＯＨ中に溶解した。15 parts of salicylic acid, 150 parts of water and 14.6 parts of 36
Be” (30.30% by weight) was dissolved in NaOH.
５部のＮａ２ＣＯ，（２０％溶液（部／容量）として）
を加え且つ５０部の氷で０〜２．℃に冷却して得られた
溶液を上記のテトラゾ体と素早く混合した（約２１分間
）。5 parts Na2CO, (as a 20% solution (parts/volume))
and 50 parts of ice for 0 to 2. The resulting solution was cooled to 0.degree. C. and quickly mixed with the above tetrazo compound (about 21 minutes).
１５部のＮａ，ＣＯ，を２０％溶液（部／容量）として
１時間で加えた。15 parts of Na, CO, as a 20% solution (parts/volume) were added over 1 hour.
温度は０〜２℃であり、ＰＨ値は約９であつた。最後に
、これを完全にカツプリングさせるために２時間攪拌し
た。例２
４５部の水と５２部の２０プＢｅ′（３２．１４重量（
ｆｌ））ＨＣＩに懸濁させた２０．４部の４，４′ジア
ミノベンズアニリドを２００部の氷で冷却しした後、こ
れに０〜５℃において１２．５部のＮａＮＯ２を５０部
の水に溶解してなる溶液を滴下することによりテトラゾ
化した。The temperature was 0-2°C and the pH value was about 9. Finally, it was stirred for 2 hours to ensure complete coupling. Example 2 45 parts of water and 52 parts of 20% Be' (32.14 wt.
fl)) 20.4 parts of 4,4' diaminobenzanilide suspended in HCI are cooled with 200 parts of ice and then 12.5 parts of NaNO2 are added to 50 parts of water at 0-5°C. Tetrazotization was carried out by dropping a solution obtained by dissolving in .
これを１〜１．５のＰＨ値で１時間攪拌した。過剰の亜
硝酸をスルフアミン酸により除去した。１３．５部のサ
リチル酸を１８０部の水と６．５部のＮａ２ｃＯ３に溶
解したが、ＰＨ値は７．５であつた。This was stirred for 1 hour at a pH value of 1-1.5. Excess nitrous acid was removed with sulfamic acid. 13.5 parts of salicylic acid was dissolved in 180 parts of water and 6.5 parts of Na2cO3, and the pH value was 7.5.
１００部の氷を添加した後、全体を前記のテトラゾ体上
に細い流れとして注いだ。After adding 100 parts of ice, the whole was poured in a thin stream onto the tetrazo.
ＰＨ値を２９部のＮａ２ｃＯ３により９〜９．５とした
。攪拌をＯ〜５℃で３時間行ない、そして２７０部の４
０℃の水に溶解した１７．２部の１−ナフチルアミノ−
６／７ースルホン酸と９．３部の３６チＢｅ゛（３０．
３０重量（：ｆｌ））ＨａＯＨとからなり且つ１００部
の氷で冷却した溶液を混合した。これを一夜攪拌した。
翌朝、ＰＨ値を４２部の２００Ｂｅ゛（３２．１４重量
％）ＨＣＩにより２．５とした。１５分間攪拌した後、
ＰＨ値を２２．５部の３６。The pH value was adjusted to 9-9.5 with 29 parts of Na2cO3. Stirring was carried out for 3 hours at 0-5°C and 270 parts of 4
17.2 parts of 1-naphthylamino- dissolved in water at 0°C
6/7-sulfonic acid and 9.3 parts of 36%
A solution consisting of 30 parts by weight (: fl) HaOH and cooled with 100 parts of ice was mixed. This was stirred overnight.
The next morning, the pH value was adjusted to 2.5 with 42 parts of 200Be' (32.14% by weight) HCI. After stirring for 15 minutes,
PH value 22.5 parts 36.
Ｂｅ” （３０．３０重量％）ＮａＯＨにより８．５に
上昇させてカツプリングを完了させた。この反応物に２
００部の氷と６０部の６０せＢｅ゛（７８．５重量％）
Ｈ２ＳＯ４を添加し、そして１１．５部のＮａＮＯ２を
５０部の水に溶解してなる溶液を表面下に徐々に導入す
ることによりジアゾ化した。攪拌を翌日まで行ない、そ
して過剰の亜硝酸をスルフアミン酸により除去し、次い
で下記のようにして製造した懸濁液を混合した。１６．
３部のｍ−フエニレンジアミンを３３０部の水に溶解し
、少量の２０ンＢｅ”（３２．１４重量知ＨＣＩにより
５〜５．５のＰＨ値とした。Coupling was completed by increasing Be” (30.30% by weight) to 8.5 with NaOH.
00 parts of ice and 60 parts of 60 Be (78.5% by weight)
Diazotization was carried out by adding H2SO4 and slowly introducing a solution of 11.5 parts NaNO2 in 50 parts water subsurface. Stirring was continued until the next day and excess nitrous acid was removed with sulfamic acid and the suspension prepared as described below was mixed. 16.
3 parts of m-phenylenediamine were dissolved in 330 parts of water and brought to a pH value of 5-5.5 with a small amount of 20 N Be'' (32.14 gw HCl).
２７０部の氷と７．２部の亜硝酸ナトリウムを添加した
。270 parts of ice and 7.2 parts of sodium nitrite were added.
次いで２６．１部の水で希釈した２６．１部の２０。Ｂ
ｅ”（３２．１４重量％）ＨＣＩを表面下に３時間で導
入した。この混合物をコンゴーレツド点まで弱酸性にし
た。攪拌を室温で翌朝まで行なつた。反応物を１３５部
の岩塩により１７％で塩析し、沈澱した染料を真空ろ過
し、十分に圧搾した。このケークを４００部の９０℃の
水に懸濁させ、均質化し、次いで３００部の氷で冷却し
た。カツプリング体を１２０部の３６却Ｂｅ”（３０．
３０重量％）ＮａＯＨにより７．５のＰＨ値となし、翌
日まで攪拌し続けた。Then 26.1 parts of 20 diluted with 26.1 parts of water. B
e” (32.14 wt. %) HCl was introduced subsurface over 3 hours. The mixture was made slightly acidic to the Congo Red point. Stirring was continued at room temperature until the next morning. The reactants were mixed with 135 parts of rock salt to %, the precipitated dye was vacuum filtered and thoroughly pressed. The cake was suspended in 400 parts of 90° C. water, homogenized and then cooled with 300 parts of ice. Part 36 of "Be" (30.
The pH value was adjusted to 7.5 with NaOH (30% by weight) and stirring was continued until the next day.
これを７０℃に加熱し、９０部の岩塩により３％（部／
容量）で塩析した。真空ろ過し、十分に圧搾した。これ
を８０℃で乾燥した。このようにして得られた染料はセ
ルロース系繊維を良好な安定特性を有する褐色の色相に
染色した。得られた染料の可視光での吸収極大波長は３
８２ｍμ（ＰＨ９の水溶液で測定）であつた。This was heated to 70°C and added with 90 parts of rock salt to 3% (parts/parts)
salting out). Vacuum filtered and thoroughly pressed. This was dried at 80°C. The dye thus obtained dyes cellulosic fibers in a brown hue with good stability properties. The absorption maximum wavelength of the obtained dye in visible light is 3
It was 82 mμ (measured with an aqueous solution of pH 9).
Claims (1)
ラゾ化した４，４′−ジアミノベンズアニリドをアルカ
リ性媒質中でサリチル酸とカップリングさせ、得られた
ジアゾ−モノアゾ体を実質上アルカリ性媒質中で前記Ａ
の意味を有するカップリング要素とカップリングさせる
ことを特徴とするスルホン化アゾ染料の製造法。[Claims] 1. In producing a sulfonated azo dye having the following general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ where A = ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ In producing a sulfonated azo dye, tetrazotized 4 , 4'-diaminobenzanilide is coupled with salicylic acid in an alkaline medium, and the resulting diazo-monoazo compound is coupled with the above-mentioned A in a substantially alkaline medium.
1. A method for producing a sulfonated azo dye, which comprises coupling with a coupling element having the following meaning.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2038174A IT1007324B (en) | 1974-02-11 | 1974-02-11 | WATER-SOLUBLE AZO DYES DERIVED FROM 4.4 DIAMINOBENZANILIDE |
| IT20381A/74 | 1974-02-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58194956A JPS58194956A (en) | 1983-11-14 |
| JPS5945701B2 true JPS5945701B2 (en) | 1984-11-08 |
Family
ID=11166217
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1639375A Expired JPS5839181B2 (en) | 1974-02-11 | 1975-02-10 | 4,4'- diaminobenzanilide |
| JP6931283A Expired JPS5945701B2 (en) | 1974-02-11 | 1983-04-21 | 4,4↑Water-soluble azo dye derived from 1-diaminobenzanilide |
| JP6931183A Expired JPS5945700B2 (en) | 1974-02-11 | 1983-04-21 | 4,4↑Water-soluble azo dye derived from 1-diaminobenzanilide |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1639375A Expired JPS5839181B2 (en) | 1974-02-11 | 1975-02-10 | 4,4'- diaminobenzanilide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6931183A Expired JPS5945700B2 (en) | 1974-02-11 | 1983-04-21 | 4,4↑Water-soluble azo dye derived from 1-diaminobenzanilide |
Country Status (10)
| Country | Link |
|---|---|
| JP (3) | JPS5839181B2 (en) |
| BE (1) | BE825409A (en) |
| CA (1) | CA1037029A (en) |
| CH (1) | CH624424A5 (en) |
| DE (1) | DE2505188C2 (en) |
| ES (1) | ES434567A1 (en) |
| FR (1) | FR2260607B1 (en) |
| GB (1) | GB1486542A (en) |
| IT (1) | IT1007324B (en) |
| NL (1) | NL7501419A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61203497U (en) * | 1985-06-10 | 1986-12-20 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05217083A (en) * | 1992-02-03 | 1993-08-27 | Adobitsuku:Kk | Alarm device with infrared-ray detector |
| JP5022744B2 (en) | 2007-03-13 | 2012-09-12 | 本田技研工業株式会社 | Vehicle assembly equipment |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH212995A (en) * | 1938-10-05 | 1940-12-31 | Geigy Ag J R | Process for the preparation of a hexakisazo dye. |
| US2204230A (en) * | 1939-03-29 | 1940-06-11 | Du Pont | Azo dyes |
| DE849287C (en) * | 1949-07-20 | 1952-09-15 | Ciba Geigy | Process for the preparation of trisazo dyes |
| CH313297A (en) * | 1953-01-30 | 1956-03-31 | Geigy Ag J R | Process for the production of a brown leather dye |
| BE795378A (en) * | 1972-02-15 | 1973-08-13 | Sandoz Sa | NEW POLYAZOIC DYES AND THEIR PREPARATION |
-
1974
- 1974-02-11 IT IT2038174A patent/IT1007324B/en active
-
1975
- 1975-02-06 NL NL7501419A patent/NL7501419A/en not_active Application Discontinuation
- 1975-02-07 GB GB535575A patent/GB1486542A/en not_active Expired
- 1975-02-07 DE DE19752505188 patent/DE2505188C2/en not_active Expired
- 1975-02-08 ES ES434567A patent/ES434567A1/en not_active Expired
- 1975-02-10 FR FR7504026A patent/FR2260607B1/fr not_active Expired
- 1975-02-10 CH CH166375A patent/CH624424A5/en not_active IP Right Cessation
- 1975-02-10 CA CA219,678A patent/CA1037029A/en not_active Expired
- 1975-02-10 JP JP1639375A patent/JPS5839181B2/en not_active Expired
- 1975-02-11 BE BE153254A patent/BE825409A/en not_active IP Right Cessation
-
1983
- 1983-04-21 JP JP6931283A patent/JPS5945701B2/en not_active Expired
- 1983-04-21 JP JP6931183A patent/JPS5945700B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61203497U (en) * | 1985-06-10 | 1986-12-20 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2505188A1 (en) | 1975-08-14 |
| CA1037029A (en) | 1978-08-22 |
| JPS5945700B2 (en) | 1984-11-08 |
| ES434567A1 (en) | 1976-12-01 |
| FR2260607A1 (en) | 1975-09-05 |
| JPS58194955A (en) | 1983-11-14 |
| CH624424A5 (en) | 1981-07-31 |
| NL7501419A (en) | 1975-08-13 |
| JPS58194956A (en) | 1983-11-14 |
| GB1486542A (en) | 1977-09-21 |
| JPS5839181B2 (en) | 1983-08-27 |
| IT1007324B (en) | 1976-10-30 |
| DE2505188C2 (en) | 1984-02-16 |
| FR2260607B1 (en) | 1977-04-15 |
| JPS50110424A (en) | 1975-08-30 |
| BE825409A (en) | 1975-08-11 |
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