JPS6261617B2 - - Google Patents
Info
- Publication number
- JPS6261617B2 JPS6261617B2 JP54096863A JP9686379A JPS6261617B2 JP S6261617 B2 JPS6261617 B2 JP S6261617B2 JP 54096863 A JP54096863 A JP 54096863A JP 9686379 A JP9686379 A JP 9686379A JP S6261617 B2 JPS6261617 B2 JP S6261617B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- dye
- general formula
- chlorine
- dyeing
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
- C09B29/0834—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -O-
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
本発明の対像は一般式(1)
（式中Ｘは塩素−又は臭素−原子を、R1はC1
−C4−アルキル基を、R2はメチル−又はエチル
−基を示す。）
で表わされる新規マリンブル−色分散染料、その
製造法及びこれを含有する染料調製物並びにこれ
を用いて合成繊維材料を染色又は捺染する方法で
ある。
ベルギー特許第634032号明細書中に一般式(2)
（式中Ｘは塩素−又は臭素−原子を、R1はC1
−C4アルキル基を、R2はメチル−又はエチル−
基を示す。）
で表わされる染料が記載されている。
本発明による染料はアセチルアミノ基の代りに
プロピオニルアミノ基を含有することでこの公知
の染料と相違することが明白である。したがつて
一般式(1)で表わされる本発明による染料が対応す
る、上述の一般式(2)で表わされる、アセチルアミ
ノ基を有する公知染料と対比して有利に相違する
ことは予期されなかつたことである。
しかし驚くべきことに次のことが見い出され
た。すなわち上記一般式(1)で表わされる新規染料
は前記一般式(2)で表わされる類似染料に比して巻
き体上に得られる染色が明らかにより小さい摩耗
性を示しかつ全く沈着を示さない点で優れてい
る。
合成繊維材料の染色又は捺染に、特にポリエス
テル繊維の染色又は捺染に適する本発明による染
料は良好な耐光性及び耐廃ガス性を有する。更に
この染料は極めて良好なカラービルドアツプ性及
び小さい還元感度を示しかつ染色に際しての温度
変化に対するその感受性が小さい。本発明による
染料は急速染色法に及びポリエステル−羊毛−混
合織物中のポリエステル部分の染色に適してい
る。
また本発明による新規染料は有機溶剤から上述
の繊維材料を染色するのに適し、また通常の染色
組成物の形で使用しうる。
本発明による染料の製造は公知方法で２，４−
ジニトロ−６−クロルアニリンの又は２，４−ジ
ニトロ−６−ブロムアニリンのジアゾ化物と一般
式(3)
（式中R1及びR2は上述の意味を有する。）
で表わされるカツプリング成分とを酸性、水性溶
液の形でカツプリングして行われる。
本発明による染料及び場合によりその他の分散
染料を含む染料調製物の製造は本発明による新規
染料を分散剤、たとえばリグニンスルホネートと
湿式粉砕して行われる。
例 １
２，４−ジニトロ−６−クロルアニリン217.5
重量部を96％硫酸1000重量部中に導入し、撹拌下
溶解する。次いで40％ニトロシル硫酸320重量部
を加え、この際外部冷却器で温度を30−35℃に保
つ。次いで２時間30−35℃で撹拌する。この時間
の経過後ジアゾ化は終了する。得られたジアゾニ
ウム塩溶液を60分以内で水4000重量部、氷6000重
量部、氷酢酸1000重量部及び２−エチルアミノ−
４−プロピオニルアミノ−１−β−メトキシエト
キシベンゾール280重量部から成る撹拌された混
合物に添加する。その際温度は＋５℃を超えては
ならない。これは更に氷を加えて達成される。３
時間撹拌し、形成された染料を取し、酸が除去
されるまで水洗する。乾燥後染料410重量部が得
られる。これは理論値の83％の収率に相当する。
得られた染料は式
に相当する。λmax×598
この染料を含む染色組成物はポリエステル繊維
上に濃いマリンブルー色の染色を与える。
同様に次表に記載された、一般式(1)
（式中Ｘ，R1及びR2は上述の意味を有する。）
で表わされる新規染料を製造する。これらは同様
にポリエステル繊維材料上に濃いマリンブル−色
染色を生じる。
The counterpart of the present invention is the general formula (1) (In the formula, X is a chlorine or bromine atom, R 1 is C 1
-C4 -alkyl group, and R2 represents methyl or ethyl group. ) A novel marine blue color disperse dye, a method for producing the same, a dye preparation containing the same, and a method for dyeing or printing synthetic fiber materials using the same. General formula (2) in the specification of Belgian patent No. 634032 (In the formula, X is a chlorine or bromine atom, R 1 is C 1
-C4 alkyl group, R2 is methyl- or ethyl-
Indicates the group. ) are listed. It is clear that the dye according to the invention differs from this known dye by containing a propionylamino group instead of an acetylamino group. Therefore, it was not expected that the dye according to the present invention represented by the general formula (1) would be advantageously different from the corresponding known dye having an acetylamino group represented by the above-mentioned general formula (2). That's what happened. However, surprisingly, the following was discovered. In other words, the new dye represented by the above general formula (1) shows that the dyeing obtained on the roll is clearly less abrasive and shows no deposits compared to the similar dye represented by the above general formula (2). Excellent. The dyes according to the invention, which are suitable for dyeing or printing synthetic fiber materials, in particular for dyeing or printing polyester fibers, have good light fastness and waste gas resistance. Furthermore, this dye exhibits very good color build-up properties and low reduction sensitivity and its sensitivity to temperature changes during dyeing is low. The dyes according to the invention are suitable for rapid dyeing processes and for dyeing polyester parts in polyester-wool blend fabrics. The novel dyes according to the invention are also suitable for dyeing the above-mentioned textile materials from organic solvents and can be used in the form of customary dyeing compositions. The dye according to the invention can be prepared by known methods such as 2,4-
Diazotized product of dinitro-6-chloroaniline or 2,4-dinitro-6-bromoaniline and general formula (3) (In the formula, R 1 and R 2 have the above-mentioned meanings.) This is carried out by coupling a coupling component represented by the following in the form of an acidic, aqueous solution. The preparation of dye preparations containing the dyes according to the invention and optionally other disperse dyes is carried out by wet grinding the novel dyes according to the invention with dispersants, for example ligninsulfonates. Example 1 2,4-dinitro-6-chloroaniline 217.5
Part by weight was introduced into 1000 parts by weight of 96% sulfuric acid and dissolved under stirring. Then 320 parts by weight of 40% nitrosyl sulfuric acid are added, maintaining the temperature at 30-35°C with an external cooler. Then stir for 2 hours at 30-35°C. After this time has elapsed, diazotization is complete. The obtained diazonium salt solution was mixed with 4000 parts by weight of water, 6000 parts by weight of ice, 1000 parts by weight of glacial acetic acid and 2-ethylamino-
Add to a stirred mixture consisting of 280 parts by weight of 4-propionylamino-1-β-methoxyethoxybenzole. The temperature must not exceed +5°C. This is accomplished by adding more ice. 3
Stir for an hour and remove the dye formed and wash with water until the acid is removed. After drying, 410 parts by weight of dye are obtained. This corresponds to a yield of 83% of theory.
The resulting dye has the formula corresponds to λmax×598 A dyeing composition containing this dye gives a deep marine blue dyeing on polyester fibers. General formula (1) also listed in the table below (In the formula, X, R 1 and R 2 have the above meanings.)
A new dye represented by is produced. These likewise produce deep marine blue dyeings on polyester fiber materials.
【表】【table】
【表】
＼
C２H５
【table】 \
C 2 H 5
Claims (1)
−C4−アルキル基を、R2はメチル−又はエチル
−基を示す。） で表わされる染料。 ２ 一般式(1) （式中Ｘは塩素−又は臭素−原子を、R1はC1
−C4−アルキル基を、R2はメチル−又はエチル
−基を示す。） で表わされる染料の少なくとも１種を単独で又は
これとその他の分散染料との混合物として含有す
る染料調製物。 ３ ２，４−ジニトロ−６−クロルアニリンの又
は２，４−ジニトロ−６−ブロムアニリンのジア
ゾ化物を一般式(3) （式中R1はC1−C4−アルキル基を、R2はメチ
ル−又はエチル−基を示す。） で表わされるカツプリング成分とカツプリングし
て一般式(1) （式中Ｘは塩素−又は臭素−原子を示し、R1
及びR2は上述の意味を有する。） で表わされる染料を製造する方法。[Claims] 1 General formula (1) (In the formula, X is a chlorine or bromine atom, R 1 is C 1
-C4 -alkyl group, and R2 represents methyl or ethyl group. ) A dye represented by 2 General formula (1) (In the formula, X is a chlorine or bromine atom, R 1 is C 1
-C4 -alkyl group, and R2 represents methyl or ethyl group. ) A dye preparation containing at least one dye represented by the following formula alone or in a mixture with other disperse dyes. 3 A diazotized product of 2,4-dinitro-6-chloroaniline or 2,4-dinitro-6-bromoaniline with the general formula (3) (In the formula, R 1 represents a C 1 -C 4 -alkyl group, and R 2 represents a methyl or ethyl group.) When coupled with a coupling component represented by the general formula (1), (In the formula, X represents a chlorine or bromine atom, and R 1
and R 2 have the meanings given above. ) A method for producing a dye represented by
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2833854A DE2833854C2 (en) | 1978-08-02 | 1978-08-02 | New navy blue disperse dyes, processes for their production and their use for dyeing or printing synthetic fiber materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5523190A JPS5523190A (en) | 1980-02-19 |
| JPS6261617B2 true JPS6261617B2 (en) | 1987-12-22 |
Family
ID=6046016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9686379A Granted JPS5523190A (en) | 1978-08-02 | 1979-07-31 | Novel marine blue disperse dystuff * production thereof * dyestuff preparation containing said dyestuff and dyeing or printing synthetic fiber material using said preparation |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5523190A (en) |
| BE (1) | BE878039A (en) |
| BR (1) | BR7904927A (en) |
| CH (1) | CH642988A5 (en) |
| DE (1) | DE2833854C2 (en) |
| FR (1) | FR2432537B1 (en) |
| GB (1) | GB2027733B (en) |
| IT (1) | IT1165279B (en) |
| MX (1) | MX150602A (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3121320A1 (en) * | 1981-05-29 | 1982-12-16 | Hoechst Ag, 6000 Frankfurt | NEW COLOR PRESENTATIONS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR COLORING AND PRINTING SYNTHETIC FIBER MATERIALS |
| DE3133355A1 (en) * | 1981-08-22 | 1983-03-10 | Hoechst Ag, 6000 Frankfurt | NEW NAVY BLUE DISPERSION DYES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR COLORING OR PRINTING SYNTHETIC FIBER MATERIALS |
| US4494957A (en) * | 1982-05-17 | 1985-01-22 | Research Association Of Synethtic Dyestuffs | Dye compositions for polyester fibers |
| DE3222013A1 (en) * | 1982-06-11 | 1983-12-15 | Hoechst Ag, 6230 Frankfurt | METHOD FOR PRODUCING NUCLEAR-SUBSTITUTED N-ALKYLANILINES |
| DE3539771A1 (en) * | 1985-11-09 | 1987-05-14 | Cassella Ag | MIXTURES OF BLUE DISPERSION DYES AND THEIR USE FOR DYING POLYESTER |
| DE3834530A1 (en) * | 1988-10-11 | 1990-04-12 | Cassella Ag | COLOR-RESISTANT MONOAZO DYE, THEIR PRODUCTION AND USE |
| DE3908445A1 (en) * | 1989-03-15 | 1990-09-20 | Cassella Ag | DYE MIXTURE |
| JPH04286577A (en) * | 1991-03-13 | 1992-10-12 | Kanebo Ltd | Package transfer device |
| JPH04115859U (en) * | 1991-03-26 | 1992-10-15 | 株式会社豊田自動織機製作所 | Pezgu tray separation device |
| JPH0623967U (en) * | 1992-08-05 | 1994-03-29 | 村田機械株式会社 | Tray with sideways pegs |
| JP3048093B2 (en) * | 1992-09-11 | 2000-06-05 | 鐘紡株式会社 | Package transfer device |
-
1978
- 1978-08-02 DE DE2833854A patent/DE2833854C2/en not_active Expired
-
1979
- 1979-07-30 CH CH702379A patent/CH642988A5/en not_active IP Right Cessation
- 1979-07-31 IT IT24818/79A patent/IT1165279B/en active
- 1979-07-31 JP JP9686379A patent/JPS5523190A/en active Granted
- 1979-08-01 MX MX178744A patent/MX150602A/en unknown
- 1979-08-01 BR BR7904927A patent/BR7904927A/en not_active IP Right Cessation
- 1979-08-01 GB GB7926762A patent/GB2027733B/en not_active Expired
- 1979-08-02 BE BE0/196572A patent/BE878039A/en not_active IP Right Cessation
- 1979-08-02 FR FR7919842A patent/FR2432537B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| MX150602A (en) | 1984-06-06 |
| DE2833854C2 (en) | 1980-09-04 |
| BR7904927A (en) | 1980-05-06 |
| IT1165279B (en) | 1987-04-22 |
| FR2432537B1 (en) | 1986-07-04 |
| IT7924818A0 (en) | 1979-07-31 |
| FR2432537A1 (en) | 1980-02-29 |
| GB2027733A (en) | 1980-02-27 |
| CH642988A5 (en) | 1984-05-15 |
| JPS5523190A (en) | 1980-02-19 |
| GB2027733B (en) | 1982-11-03 |
| BE878039A (en) | 1980-02-04 |
| DE2833854B1 (en) | 1980-01-03 |
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