JPS5887155A - Water-soluble disazo compound, manufacture and use as dye - Google Patents

Water-soluble disazo compound, manufacture and use as dye

Info

Publication number
JPS5887155A
JPS5887155A JP5611982A JP5611982A JPS5887155A JP S5887155 A JPS5887155 A JP S5887155A JP 5611982 A JP5611982 A JP 5611982A JP 5611982 A JP5611982 A JP 5611982A JP S5887155 A JPS5887155 A JP S5887155A
Authority
JP
Japan
Prior art keywords
group
general formula
compound
formula
sulfatoethyl
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.)
Granted
Application number
JP5611982A
Other languages
Japanese (ja)
Other versions
JPH0420029B2 (en
Inventor
ヨハン・ウエングヘ−フエル
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of JPS5887155A publication Critical patent/JPS5887155A/en
Publication of JPH0420029B2 publication Critical patent/JPH0420029B2/ja
Granted legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44Reactive 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
    • C09B62/503Reactive 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
    • C09B62/507Azo dyes
    • C09B62/513Disazo or polyazo dyes

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  • 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、権維反j心性注負を肩する水浴江アゾ染桐の
工9.的分封に仕る。
DETAILED DESCRIPTION OF THE INVENTION The present invention is a water bathing method for dyeing paulownia wood that takes care of power, power, and rebellion.9. Serve the target.

本発明により一般式(1) をMする、耕規なIlfl]1111tりる水浴性ジス
アゾ化合物を児甫した。上記式(L)中Mは水系原子又
は金属例えはアルカリ金−又はアルカリ土類金−Vすえ
Vゴナトリウム、カリウム及びカルシウムの当t (l
−意味し、円方の弐外り基Xは相互に同一か又は相互に
異なった意味を有しそして夫々Xはビー ル4 又Ir
eβ−スルファトエチルー基(Md;上記の意味?を勺
する式−〇H,−(J−一080.M IIこ相当1−
る)又はI−チオスルファトエチル−基(Mが上記の怠
体?南すゐ式−0H2−0鳥−8−田、Hに相当する)
を示し七してR龜大々エトキシ−8,A4 V(−メト
キシ基てりる。
According to the present invention, a water bathable disazo compound having the general formula (1) has been produced. In the above formula (L), M is an aqueous atom or a metal such as alkali gold or alkaline earth gold, V, gonaium, potassium, and calcium.
- meaning, the two outer radicals X of the circle have mutually the same or mutually different meanings, and each X is beer 4 or Ir
eβ-sulfatoethyl group (Md; the formula -〇H, -(J-1080.M II corresponding to 1-
) or an I-thiosulfatoethyl group (M corresponds to the above-mentioned lazy body?nansui-0H2-0tori-8-da, H)
Indicates 7 and R ethoxy-8,A4 V(-methoxy group).

妙「或ン!ジスアソ°化* r:!!7JtまIff 
’+王ル態でもその場の)θ悪でも仕ることがでさる。
Myo: “Aru! Jisuaso°* r:!!7Jt MaIf
Even if you are in a + royal state, you can serve even if you are in the situation) θ evil.

これは虫打にアルカリ−及びアルカリ土−iA K M
 JMのル態で必るのが好丑しくそして又これらの塩の
庇Jl!Aでヒドロキン−又はカルボン1ミド−、!1
!:ざ南繊紺又は皮革の染色又は鉱泉に便用するのが好
lしい。
This is alkaline and alkaline earth for insect attack - iA K M
It's a must with JM's style, and these salt eaves Jl! A is hydroquine or carboxylamide,! 1
! : It is preferable to use it for dyeing Zanan textile navy blue or leather or for mineral springs.

式(1)の肪規化合切は式(#:離改の形でifd載し
て) C馬−080,H 更に不党明は一般式(1)の上にジスアゾ化合物の製法
に関する。これは、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M、味を肩する)の化名゛吻と弱酸性
媒悴好ましくは水1生媒体中で体VcO乃至2.5のp
H−値でカップリンクし、次に一般式(4)(式中M及
びX)ゴ上記の意味金山する)のこのモノアゾ化は吻?
弱酸・註乃芋弱アルカリ性媒体好ましくは水注媒捧中で
休に4乃至7のpI−i−値で一般式(5) (式中R及びXは上記の意味を有する)のジアゾ化した
芳香族アミンとカップリングすることを特徴としている
The aliphatic compound of formula (1) is expressed by the formula (#: written in the form of ``ifd'') C-080,H.Furthermore, the non-conformity is related to the method for producing the disazo compound above the general formula (1). This is achieved by first diazotizing the aromatic amine of the general formula (2) (wherein X has the above meaning), and then converting it into the chemical name of the general formula (3) (wherein M is the above M, representing the taste).゛The body VcO to 2.5 p in a weakly acidic medium, preferably water.
This monoazotization of the general formula (4) (in which M and
The diazotization of the general formula (5) (wherein R and It is characterized by coupling with aromatic amines.

芳査秩アミン(2)及び(5)のジアゾ化に地元の公知
方法でνUえは墳准水丘妹体中で胆硝醒ナトリウムによ
り−50乃至+19Cの温度で行われる。同様Vこ円カ
ップリン、1反ル6はそれ自体公知の方法で実施される
。オ一段階のカップリング反応は強酸性範囲でぞして殊
に5乃至5UCの温度で行わrLゐ。ガニ段階のカップ
リング反ルしNは殊に弱ば注乃至中細範囲でそして林に
5乃至30Cの温度で行われる。
The diazotization of the Hoshichichi amines (2) and (5) is carried out in a locally known method using bile aqueous sodium at temperatures of -50 to +19 C in a turquoise body. Similarly, the V-circular coupling, 1-circular coupling, and the 6-circular coupling are carried out in a manner known per se. The one-step coupling reaction is carried out in a strongly acidic range, especially at a temperature of 5 to 5 UC. The coupling reaction at the crab stage is particularly carried out in the low to medium range and at a temperature of 5 to 30C.

オニカッブリンク反ノ心の際のpH−範囲の調整のため
の赦栢合剤として好ましくは弱無機又はM機V例えば戻
ば酢ば、帥]酸、蓚酸のアルカリ−又はアルカリ土類金
属塩又は燐改の敵性塩が使用される。符にこの7こめに
炭ばナトリウム及び−カリウム、酢酸ナトリウム、硼改
ナトリウム及び殊に重重には灰ば水素ナトリウムか通す
る。
As a compensating agent for the adjustment of the pH range during the reaction of onicablink, preferably a weak inorganic or Morganic acid, an alkali or alkaline earth metal salt of oxalic acid. Alternatively, Rin Kai's hostile salt is used. In addition, sodium carbonate and potassium carbonate, sodium acetate, sodium borohydride, and especially sodium hydroxide are passed through this column.

一般式(1)一式中Xがβ−スルファトエチル基を示す
−の本発明による、化合物は又本発明により、上記の方
法で一般式(2)一式中但し両式残基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(3Jの1−7<ノー8−ナフト
ール−6,6−ジスルホン岐とカップリングしそしてこ
の様にして製造し7と、一般式(1)一式中但1−AX
の一方又は両方かβ−ヒドロキシエチル基?示す□の構
造を、0するジスアゾ化合物音それ自体公知の方法で憾
酸化剤例えば磯i苑ば又はクロルスルホン酸で式(1)
 VC相当する不発明によるスルファト化合、頻に変え
る休eこ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 according to the invention by the method described above, in which one or both of the residues X of the general formula (2) One or both of the aromatic amines of the formula - in which both residues X represent a β-hydroxyethyl group are coupled with the 1-7 < no 8-naphthol-6,6-disulfone branch of the formula (3J) and thus 7 and general formula (1), provided that 1-AX
One or both of the β-hydroxyethyl groups? A disazo compound having the structure shown in the formula (1) can be converted to 0 using a deoxidizing agent such as Iso-enba or chlorosulfonic acid by a method known per se.
The VC equivalent sulfate compound according to the invention can be prepared by frequently changing rest periods.

不発r−Aによる化合−1勿はその合成混合物からその
製造後水浴社化合吻に就で一般的に公知な方法により、
Vすえば屯房買例えば塩化ナトリウム又は塩化ノア ’
Jウムによる反沁腺体がらの沈殿、引きUトいてのろ過
により又はυFし反j心浴准自体の蒸1zt例えば1貝
務晩床Vこより、単離することができる。不発明による
化合物の単離のnσiピ方法が選択される場せ、反応浴
液が多証の屍ば塩をノ 含廟する場付#光SIJ浴液中に存征する硫販堪を沈殿
により伊c岐カルシウムとしてそしてろ過による分離に
より除去することが拒矢される。多くの賜曾又式(1,
)のこの化合物を官有する反応浴液を、場合により碌細
及び/又は緩価吻質の添ガ11後、直接膚色使用用液体
調合吻として供給することが望ましい。
Compound-1 by unexploded r-A Of course, from its synthetic mixture, after its preparation, by a generally known method,
For example, sodium chloride or noa chloride.
It can be isolated by precipitation of the glandular bodies with Jum, followed by filtration, or by evaporation of the phlegm itself, for example, by evaporation of the phlegm itself. If the non-inventive method of isolation of the compound is selected, the reaction bath liquid may contain a large amount of carcass salts, and the sulfuric acid present in the light SIJ bath liquid may be precipitated. Therefore, it is rejected as Icgi calcium and removed by separation by filtration. Numerous gift ceremonies (1,
It is desirable to supply the reaction bath containing this compound of ) directly as a liquid preparation for skin color use, optionally after addition of a fine and/or mild aphrodisiac.

本発明の新規化、84圀はヒドロキシ−又はカルシボン
アミド基冴刹槙維からlる材層又は皮革向えば天然又は
拘止セルロース又は天然、再生又は合成ボIJ ’T 
ミドからなる#R紺材料Vuえは不軌、入射、麻、ジュ
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狩に蝋紺反応染料とし
て竹に適する。殊に納″、蜆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 novelty of the present invention, 84, is a material layer or leather made of hydroxy- or carbibonamide-based solid fibers, preferably natural or bound cellulose or natural, regenerated or synthetic fibers.
#R navy blue material made of polyamide, lint, hemp, jute, viscose, human silk, wool, silk, polyamide-6, polyamide-6,6, polyamide-11 and polyamide-11
4. Suitable for bamboo as a reactive dye for dyeing or printing. In particular, the dyestuff compounds are suitable for dyeing or printing cellulose fiber materials.

耕規化賃吻は、上記の基体上で水浴性特に繊維長ルれ1
性染相に就て公知の及びノm當の染色−及び捺染法に類
似して適用及び161沿される。これは向い膚色力及び
均染性及び非常に艮好な堅牢性全市する帝祿黒色染′色
及び捺染を与える。堅牢性のうち日光堅牛牡、抗たく堅
牢性、アルカリ性及びぽ江汁堅牢性、アイロン掛は−、
ひだ付は−及び湯通し堅牢性、浴剤−及びドライクリー
ニング堅牢性、水及び海水堅牢性、塩系浴水堅牢曲及び
愼−及びアルカリ堅牢性が詠に強調される。
The cultivated proboscis has water bathability, especially fiber length 1, on the above-mentioned substrate.
It is applied and followed analogously to the known and current dyeing and printing methods for color dyeing. This gives a commercially available imperial black dyeing and printing of color strength, levelness and very good fastness. Of the fastness, Nikko Kengyu is strong, strong against alkaline and poe soup, ironing is -,
Folding and blanching fastness, bath agent and dry cleaning fastness, water and seawater fastness, salt bath water fastness and oxidation, and alkali fastness are emphasized in the poem.

それ改本節L3F3は更に不発明による化合・物音上記
の繊維材斜文1−を皮革の染色又は除染に使用すること
又は、本発明による化−8′匈全条色及び捺染産米の公
知及び通常の方法に類似して濾維材料上に適用しそして
引き枕いて回7Mする、上り己M維材料又は皮革の染色
又は捺染法に関する。
The revised section L3F3 further describes the use of the above-mentioned fibrous oblique text 1- for dyeing or decontamination of leather, or the use of the above-mentioned textile material diagonal text 1- for the dyeing or decontamination of leather, or the conversion according to the present invention - 8' of the invention, which is known in the art. and a process for dyeing or printing fibrous materials or leather, which is applied to the fibrous material and rolled for 7M analogous to conventional methods.

例えばこの方′fhは、セルロース極細材料を場合によ
り通常の染色助剤?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1生剤の使用下符に60乃至1ub
Cの温度で処理する椋にして実施され、その際繊維材料
は弁筒に艮好な染色収率で染色系れる。
For example, this 'fh' is a cellulose ultrafine material and sometimes a normal dyeing aid? Using the alkaline action 1 crude agent from a long bath by exhaustion method in an aqueous bath containing 60 to 1 ub
The process is carried out at a temperature of C, the fiber material being dyed onto the valve sleeve with a good dyeing yield.

■柴的V′C公知及び通常でめるバジング法によりセル
ロース、臓維材料上で同僚に夾nた染色収率で染色か得
られ、この方ぬはm−又は二相法テ笑施するヒとがでさ
るので、+ij+Jzsは7/レ力リ作用性剤−これは
染料の通用と同時又は該通用の後で樺雑材料上K d用
するーを用いて又はバジングした繊維材料ftb分向乃
至2u時間室温又は6UC−までの温度で油′函“させ
て又は蒸熱により又は乾熱によゐ処理により実施するこ
とができる。固層してない染料分は容易に洗出て@る。
■Shiba's V'C staining was obtained on cellulose and visceral fiber materials by the known and commonly used bagging method, with a dyeing yield similar to that of colleagues; +ij+Jzs = 7/reactive agent - which is used on the birch miscellaneous material at the same time as or after the application of the dye. This can be carried out by treatment in an oil bag at room temperature or at temperatures up to 6 UC for a period of 2 to 2 hours, or by steaming or by dry heat. Unsolidified dyes are easily washed out.

本弁明による化合切全捺染法で′欧州することは公知及
び通常の除染−及び+i!d盾法(セルロース繊#:全
染色するための)に耕似して行わnる。
It is known and common decontamination and +i! that the compound cut printing method according to the present invention can be carried out in Europe! It is carried out similarly to the shield method (for cellulose fiber #: for total dyeing).

この場合法に一相法で重仄威す) IJウム又は他の酸
結合剤?りえば血戻ばカリウム、炭ばすl−IJウム又
は−カリウム、苛性ソータ液、旬・庇カリ液又はトリク
ロル酢赦す) IJウムの存在下捺染ペースト中でそし
て引@続いての101乃至103Cでの蒸熱によシ又は
二相法で中性又は弱歌性鉱条ペーストによる除染及び引
き就いての、熱い電解質言南アルカリ性袷による面頂又
はアルカリ性、電所買言嘴処理准によるオーバ−パジン
ク及び引きiθ1いてのC重重、蒸熱又は乾熱による処
」」下実施さノtゐ様にして行うことができる11輪昇
の艮好な水準及びさえた白色下地を廟する1M色力のよ
い捺染か(4Iら7′Lゐ。碕ζ采は・lJ¥lI肩条
WF vc閑係なく尚い色調舟枕?示ア。
In this case, the one-phase method is more important) IJum or other acid binder? If the blood returns to potassium, charcoal, IJum or potassium, caustic sorter solution, potash solution or trichlor vinegar) in the printing paste in the presence of IJum and subsequently at 101 to 103C. Decontamination by steaming or two-phase process with neutral or mild mineral paste and subsequent decontamination with hot electrolyte and alkaline coating or over-contamination with alkaline and alkaline treatment. Pazinking and pulling iθ1 by heavy duty, steam or dry heat to achieve an excellent level of 11-ring coloring and a 1M color strength to create a white base. Good printing (4I and 7'L).

ホリアミトー又はポリウレタン家維の染色は通常敗性猿
境から実施さ扛る。7−IT数のpH−値を保つために
クリえは朱f合に匪敢又は昨畝及び酔眼アンモニウムな
る稜帥J剤を冷加することができる。染色の1史月E 
”J 1]’にな均染1牛を11−るh的で通窩の均栄
酌の除動jか推奨ざノーしる。染色は沸とう温ル、でも
110乃工1.<LIUても実施することがでさる。染
色全仕上けるたりにアン七二アルカリ任伎処堆か’)!
’ +!Iでのることができる。
Dyeing of polyurethane fibers or polyurethane fibers is usually carried out from the septic stage. In order to maintain the pH value of 7-IT, the liquid can be cooled with a chemical agent such as chlorine or chlorine and ammonium. 1st history of dyeing E
I don't recommend removing the uniformly dyed cow in the "J 1". It can also be carried out even if it is dyed completely.
'+! You can board with I.

次の1タリにより小9七り」全層を列ずゐ。符占己しV
上い眠り\セこに記載の部は月1拓一部でりり、百分率
の記載は重電%に関する。谷i都と車輩部との比はリッ
トル対キロクラムで茹る。
With the next 1 tari, it will be 97th grade.'' All the layers will be lined up. Divination self V
The parts listed on the page are 1 ton per month, and the percentages listed are heavy electric %. The ratio between Tani Ito and Kurumabu is boiled in liters to kilograms.

例  1 水20(J線中VC4−、&−スルフIトエナルスルホ
ニルーアニリン200都を言むpHb、Ll乃至5.5
の水性浴液に氷24tJ部及び61チ塩咳155部を加
え75゜アニリン化合物′f!:40チ水1生亜硝醒ナ
トリウム沼液94.5谷辿都の添刀■により40分以内
にOC乃牟5Cの扇度でジアゾ化する。7!お1時間す
乃至8Cで引き就き攪拌しそして小過剰の叱硝猷金小量
のyミドスルホン市の添別により分解すゐ。このジアゾ
ニウム塩浴液に1−アば)−8−ヒドロキシ−ナフタリ
ン−6,6−ジスルホンば227都を撤入する。
Example 1 Water 20 (J line VC4-, &-SulfItoenalsulfonyl-aniline 200 pHb, Ll to 5.5
Add 24 tJ parts of ice and 155 parts of 61% salt to the aqueous bath solution of 75° aniline compound'f! : 40 pieces of water 1 raw nitrite sodium swamp liquid 94.5 diazotized with OC Nomu 5C fan degree within 40 minutes by using the attached sword ■ of Tani Todo. 7! Stir for 1 hour at 8C and dissolve by adding a small amount of sulfuric acid in excess. 1-Ab)-8-hydroxy-naphthalene-6,6-disulfone is added to this diazonium salt bath solution.

その抜混付吻のpH−%は約1.5である。16時曲1
5乃キ19Cで引き続きづ覚押し、次に炭酸すトリウム
7 B *IIにより66乃至6.8のpi(−値に調
整する。
The pH-% of the discharging and mixing proboscis is approximately 1.5. 16:00 song 1
Continue to press with 5 to 19C, then adjust to a pi (-value) of 66 to 6.8 with sodium carbonate 7B*II.

モノアゾ化七′憎のこの殆んど中性の息1陶液Qて次に
撹拌下ジアゾニウム塩浴液−これは常法で4−β−スル
ファトエチルスルホニル−2,5−ジメトキシ−アニリ
ン246部から製造し、その後血炭敵す) IJウムで
5−6 乃至5.8 (1) pH−1直に調量17℃
βるm−と川1える。この反1心混合+’tAk数1呼
間5.8乃至6.6のpf(、−im及び15乃至18
tL’(D温良で引さ絖@攪拌する。けい七う土10品
の添那後反j心群液k(%匿にしヤしてろ液を減1t−
1;6 Q Cで蒸発乾固する。蔚砕伐式の化合物71
0郁をざ市する黒巴の疏y外貞含刹(主として黒化ナト
リウム)粉末が僧ら7″Lる。
This almost neutral solution of the monoazotized 7' salt is then mixed with stirring in a diazonium salt bath solution - 4-β-sulfatoethylsulfonyl-2,5-dimethoxy-aniline 246 5-6 to 5.8 (1) Measure directly at pH-1 at 17°C.
βru m- and river 1eru. This anti-single core mixture +'tAk number of 5.8 to 6.6 pf (, -im and 15 to 18
tL' (D) Draw the wire at a warm temperature and stir. After adding 10 pieces of diatomaceous earth, the filtrate was reduced by 1 t-
Evaporate to dryness at 1;6 QC. Compound 71
The amount of black tomoe powder (mainly blackened sodium) available in the market is 7"L.

この化84Jは染料としてすばらしく醜しそしてアルカ
リf’F用社の存在下)a離反1心社染料にとって赳常
丘染色−及び禄染法によりセルロース極細材料を尚い製
箔−及び使用堅牛憔奮Mする帯緑黒色色調で染色する。
This compound 84J is wonderfully ugly as a dye, and in the presence of alkali f'F use) a defective 1 Shinsha dye is used for dyeing - and for making cellulose ultra-fine materials by the roku dyeing method - and for making foil - and using hardening. Dye with a greenish-black tone of M.

例  2 ?!I 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−スルファトエチルスルホニルーン、5−
ジメトキシ−アニリンを4−ビニルスルホニル−2,5
−ジメトキシーアニIJン173hl;に換える。式 の化8勿661.1郡全言/1すり黒巳、也解實含有粉
末が得られゐ。これは同様に非常に艮好な染料g:、貝
を4」シーそしてセルロース繊維材料上で高い製置−及
び・欧用堅牢注を七する帯線黒色染色を与える。例ノの
このジスアゾ化合、1乃の性<V例1のジスアゾ化8#
のそnと実際上同一で必る。
Example 2? ! I 1, except that the 4-β-sulfatoethylsulfonyl rune used therein, 5-
dimethoxy-aniline to 4-vinylsulfonyl-2,5
-DimethoxyaniiJin 173hl; A powder containing the formula 8 661.1 Gunzengen/1 Surikuromi and Yakai truth was obtained. This likewise gives a very attractive dyestuff, a banded black dyeing of 4" seashells and a high production and European fastness on cellulose fiber materials. This disazo compound of Example No. 1 <V Disazo compound of Example 1 8#
It must be practically the same as Noso n.

Claims (1)

【特許請求の範囲】 1、一般式(1) (式中Mは水系原子又は金属の当量を息休し両方のXは
相互に同一か又は相互に異なっておりそして夫々Xはビ
ニル基、β−スルファトエチル基又はI−チオスルファ
トエチル基を慧体しそしてRはメトキシ−又はエトへシ
基を示す)のジスアゾ化合物。 2、一般式−(1) (式中Mは水系原子又は金属の歯童を意味し両方の又は
相互に同一か又は相互に典なっておりそして夫々又はビ
ニル基、β−スルファトエチル基又はβ−チオスルファ
トエチル基を意味しセしてRはメトキシ−又はエトキシ
基を示す)のジスアゾ化合物を装造するために、一般式
(z) (式中Xは上記の意味金山する)の芳食族アミンをジア
ゾ化しそして頭岐注妹庫中で一般式(3) (式中Mk′i上配の上記JJk市する)の化合物と力
゛ツブリングしそして一般式(4) (式中M及びXは上記の意味仝廟すゐ)のモノアゾ化甘
吻を一般式(5) (式中R及びXは上=r2の意味を肩する)のジアゾ化
した芳香族アミンと羽は注乃主☆アルカリ性媒体中でカ
ンプリングすることft符徴とする、上i12製法。 6、 特許請求の範囲第2項に記載した一般式(2)一
式中Xが特許請求の範囲第2項記載の意味を有するか又
はXがβ−ヒドロキシエチル基を示す−の芳香族アミン
をジアゾ化しそして強酸性媒体中で特許請求の範囲第2
項に6己載した一般式(3)の化合物とカンプリングし
そしてこの株にして侍だモノアゾ化甘吻を引@就いて弱
酸性乃至弱アルカリ性媒体中で特許請求の範囲第2項に
記載した一般式(5)一式中R及びXか符p請求の範囲
第2項H己載の意味を有するか又はXかβ−ヒドロキシ
エチル基であるーのジアゾ化した芳香族アミンとカップ
リングするが、併し一般式(2)及び(5)の出発化合
物を、これらのうち少くとも11固がXに関するβ−ヒ
ドロキシエチル基を含有する株に逃択しそしてこの様に
して製造した、一般式(1)一式中M及びRか特許請求
の範囲第2項6己載のM、味を肩しそして一方のXがβ
−ヒ)”CIキシエチルit示しそして・t+u方co
Xがβ−ヒドロキシエチル基を示しそして他方のXがI
−スルファトエチルスルホニル基又はビニル&’に示す
か又は両Xが夫々β−ヒドロキシエチル基を示す−に相
当するジスアゾ化合物を個を版化剤で符許請の範囲第2
項記載に相当する一般式(1)一式中R及びX −1)
:特許請求の軛囲Δ12項tピ載の麓体をMしそして円
Xか大々β−スルファトエチル;#’t 示T カ又は
一方のXかβ−スルファトエチル基でるりそして他方の
Xがビニル基でめるーの化合物に変える、符d「請求の
範囲第2項記載の製法。 4、 一般式(リ ノ (式中Mは水系原子又は金鵡の当thtを意味し両方の
又は相互に同一か又は相互に典っておりそして大々Xは
ビニル基、β−スルファトエチル基又ハβ−チンニース
ルファトエチル意味しそしてRはメトキシ−又はエトキ
シ基を示す)のジスアゾ化合wJヲ染料として使用する
方法。 5、 ヒドロキシ−又はカルボンアミド基含有繊維から
なる材料又は皮平の染色又は鉱条に使用する、特許請求
の範回44項記載の方法。
[Claims] 1. General formula (1) (wherein M represents an aqueous atom or metal equivalent, both Xs are the same or different from each other, and each X is a vinyl group, β - a disazo compound containing a sulfatoethyl group or an I-thiosulfatoethyl group, and R represents a methoxy- or ethohexy group. 2. General formula - (1) (In the formula, M means an aqueous atom or a metal atom, both or each other are the same or mutually representative, and each or a vinyl group, a β-sulfatoethyl group, or In order to prepare a disazo compound of the general formula (z) (wherein X means a methoxy or ethoxy group), The aromatic amine is diazotized and combined with a compound of the general formula (3) (in which Mk'i is superposed on the above JJk) in a toqi-shu stock, and the compound of general formula (4) (in the formula M and X have the above-mentioned meanings) The monoazotized amine of general formula (5) (wherein R and X have the meaning of upper = r2) and the diazotized aromatic amine and feather Noshu☆The above i12 manufacturing method, which is characterized by campling in an alkaline medium. 6. In the general formula (2) described in claim 2, X has the meaning described in claim 2, or X represents a β-hydroxyethyl group. diazotized and in a strongly acidic medium as claimed in claim 2.
This strain is prepared by compounding with the compound of general formula (3) listed in Section 6, and the Samurai monoazotized sweetener is added thereto in a weakly acidic to weakly alkaline medium as described in Claim 2. Coupling with a diazotized aromatic amine in which R and X in the general formula (5) have the meanings specified in Claim 2 H, or X is a β-hydroxyethyl group However, the starting compounds of general formulas (2) and (5) were selected for strains in which at least 11 of them contained β-hydroxyethyl groups for X and the general compounds prepared in this way In the formula (1), M and R in claim 2, paragraph 6, are responsible for the taste, and one of the X is β.
- H) "CI xyethyl it and t + u side co
X represents a β-hydroxyethyl group and the other X represents I
A disazo compound corresponding to -sulfatoethylsulfonyl group or vinyl &' or both
R and X-1 in the general formula (1) corresponding to the description in Section 1)
: The yoke of the patent claim Δ12 term t The foot body of the pi is M, and the circle X is approximately β-sulfatoethyl; 4. The manufacturing method according to claim 2, in which or are mutually identical or mutually different, and X means vinyl group, β-sulfatoethyl group or A method of using the compound wJ as a dye. 5. A method according to claim 44, wherein the method is used for dyeing or striping materials or skins made of hydroxy- or carbonamide group-containing fibers.
JP5611982A 1981-04-07 1982-04-06 Water-soluble disazo compound, manufacture and use as dye Granted JPS5887155A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813113989 DE3113989A1 (en) 1981-04-07 1981-04-07 Water-soluble disazo compounds, preparation thereof and use thereof as dyes
DE3113989.2 1981-04-07

Publications (2)

Publication Number Publication Date
JPS5887155A true JPS5887155A (en) 1983-05-24
JPH0420029B2 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)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4601094B2 (en) * 1998-06-30 2010-12-22 チバ ホールディング インコーポレーテッド Mixtures of reactive dyes and their use
CN102516808A (en) * 2011-10-28 2012-06-27 浙江瑞华化工有限公司 Synthetic method of active black dye

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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
WO2013017331A1 (en) 2011-08-04 2013-02-07 Huntsman Advanced Materials (Switzerland) Gmbh Mixtures of reactive dyes and their use

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4601094B2 (en) * 1998-06-30 2010-12-22 チバ ホールディング インコーポレーテッド Mixtures of reactive dyes and their use
CN102516808A (en) * 2011-10-28 2012-06-27 浙江瑞华化工有限公司 Synthetic method of active black dye

Also Published As

Publication number Publication date
DE3113989A1 (en) 1982-11-04
JPH0420029B2 (en) 1992-03-31

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