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SU469262A3 - Method for preparing active chlorotriazine azo dye - Google Patents

Method for preparing active chlorotriazine azo dye

Info

Publication number
SU469262A3
SU469262A3 SU1803317A SU1803317A SU469262A3 SU 469262 A3 SU469262 A3 SU 469262A3 SU 1803317 A SU1803317 A SU 1803317A SU 1803317 A SU1803317 A SU 1803317A SU 469262 A3 SU469262 A3 SU 469262A3
Authority
SU
USSR - Soviet Union
Prior art keywords
chlorotriazine
azo dye
dye
preparing active
amino group
Prior art date
Application number
SU1803317A
Other languages
Russian (ru)
Inventor
Партон Бриан
Original Assignee
Империал Кемикал Индастриз Лтд (Фирма)
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 Империал Кемикал Индастриз Лтд (Фирма) filed Critical Империал Кемикал Индастриз Лтд (Фирма)
Application granted granted Critical
Publication of SU469262A3 publication Critical patent/SU469262A3/en

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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
    • C09B62/006—Azodyes
    • 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
    • C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
    • C09B62/006—Azodyes
    • C09B62/012—Metal complex azo dyes
    • 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
    • C09B62/4401—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 with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
    • C09B62/4403—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 with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
    • C09B62/4411—Azo dyes
    • 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
    • C09B62/4401—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 with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
    • C09B62/4403—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 with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
    • C09B62/4411—Azo dyes
    • C09B62/4416—Metal complex azo dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

за счет использовани  фенилендиаминодисульфокислоты обеспечивает высокую степень фиксации и улучшенные показатели прочности окраски к мокрым обработкам по оравнению с красителем, в молекуле которого И1меет€  фенилендиаАШйомошсульфокйслотный остаток.due to the use of phenylenediaminodisulfonic acid, it provides a high degree of fixation and improved color fastness properties to wet treatments as compared with a dye, in which I1 molecule has a phenylenediamine sulfo-sulfo acid residue.

Таким способом .можно .получить красители с широкой гаммой цветов и оттенков от Hi ел того до темно-синего.In this way, it is possible to obtain dyes with a wide range of colors and shades from Hi to dark blue.

Пример 1. 4,67 вес. ч. динатриевой соли 6-ами1Но-1-окси-2 - фенилазонафталин - 2, 3-дисульфокислоты в 125 вес. ч. воды добавл ют в суспензию 1,85 вес. ч. цианурхлорида и 14 вес. ч. ацетона в 112 вес. ч. смеси воды со льдом при О-5°С, причем рН среды поддерживак )тв пределах 5-7 добэвлением 10%ного водного раствора карбоната натри .Example 1. 4.67 weight. including disodium salt of 6-ami1No-1-hydroxy-2 - phenylazonaphthalene - 2, 3-disulfonic acids in 125 weight. including water added to the suspension 1.85 weight. including cyanuric chloride and 14 wt. including acetone in 112 weight. including a mixture of water and ice at -5 ° C, the pH of the medium being maintained within the range of 5-7 by adding the 10% aqueous solution of sodium carbonate.

После полного завершени  конденсации в реакционную смесь ввод т раствор 3,3 вес. ч. динатриевой соли 1,3-диаминобензол-4 ,б-дисульфокислоты в 30 вес. ч. воды, после чего темшература по;в; 1шаетс  до 35-40°С, причем .величину рН среды поддерживают в пределах 5,0-6,0 путё.м постепенного добавлени  10%-ного .водного раствора карбоната натри . По истечении 4 вес. ч. в конечный реакционный раствор .ввод т растВОР 2 вес. ч. цианурхлорида в 15 .вес. ч. ацетона , и реакционную смесь подвергают перемешиванию при О-5°С, при-чем рН среды поддерживают в пределах 5-7 путем ввода вAfter complete condensation, a solution of 3.3 wt. Is injected into the reaction mixture. including disodium salt 1,3-diaminobenzene-4, b-disulfonic acids in 30 weight. h of water, then the temperature of the; in; 1 to 35-40 ° C, and the pH of the medium is maintained in the range of 5.0-6.0 by the gradual addition of a 10% aqueous solution of sodium carbonate. After 4 weight. including in the final reaction solution. enter a dilution of 2 wt. h. cyanuric chloride in 15. weight. including acetone, and the reaction mixture is subjected to stirring at-5 ° C, while the pH of the medium is maintained within 5-7 by entering into

нее 10%-ного водного раствора ка.рбоната 1гатри .it 10% aqueous solution of ka.rbonata 1gatri.

После полного завершени  канден1сации в реакционную конечную смесь добавл ютAfter complete completion of the kandensation, add to the reaction final mixture

1,8 вес. ч. анили1Н-3-сульфокислоты и теМ|Пература повышаетс  до 35-40°С, причем рН среды поддерживают ,в пределах 5-7 добавлением 10%-ного водного раствора карбоната натри . Затем, после полного завершени 1.8 weight. including aniline1H-3-sulfonic acids and tem | peratura rises to 35-40 ° C, while the pH of the medium is maintained within the range of 5-7 by adding a 10% aqueous solution of sodium carbonate. Then after complete

конденсации краситель сусаждают добавлением хлористого натри , отфильтровывают и сушат. Установлено, что в молекуле этого красител  содержатс  2 атома хлора на каждую азогруппу, .причем этот краситель в присутствии сз зываюшего кислоту агеита окрашивает текстильные .материалы в оранжевые цветовые оттенки, которые характеризуютс  высокой прочностью в отношении действи  света и стирки.Condensation of the dye is suspended by addition of sodium chloride, filtered and dried. It has been established that the molecule of this dye contains 2 chlorine atoms for each azo group, and this dye in the presence of crushing acid ageit paints textile materials in orange color shades, which are characterized by high durability with respect to the action of light and washing.

В таблице приведены примеры красителей , которые могут быть получены в соответствии с вариантом осуществлени  предлагаемого способа, описанным в примере 4, реакцией продукта конденсации с соединением,The table lists examples of dyes that can be obtained in accordance with the embodiment of the proposed method described in Example 4 by the reaction of a condensation product with a compound

указанным во второй колонке, и цианурхларидом вместе с диамино.бензолдисульфокислотой , приведенной в третьей колонке, с последуюш ёи реакцией полученного при этом продукта реакции с циаиурхлорндом и конденсацией с соединением.indicated in the second column, and cyanurhlaride together with the diamino. benzene disulfonic acid listed in the third column, followed by the reaction of the resulting product of the reaction with cyanurhlornd and condensation with the compound.

Цветовой оттенок достигаетс  при окрашивании Описанным красителем целлюлозных текстильных материалов.The color shade is achieved by dyeing the dyed cellulosic textile materials.

Предмет изобретени Subject invention

Claims (2)

1. Способ получени  активного хлортриазинового азокрасител  общей формулы А1. A method for preparing an active chlorotriazine azo dye of general formula A )) SOjHSOjH где R - .водород или алкил;where R is hydrogen or alkyl; D - остаток аминоазОСоедииеии , в молекуле которого атомы азота св заны с углеродными атомами гомоциклического ароматического радикала;D - aminoazoedia residue, in the molecule of which nitrogen atoms are bound to carbon atoms of a homocyclic aromatic radical; X - остаток 2-с«жл-триази.на, содержащего атом хлора или брома, присоединенный к атому углерода в положении 4, а также аминогруппу или замещенную аминогруппу,X is a 2-c "l-triazi.na residue containing a chlorine or bromine atom attached to the carbon atom in position 4, as well as an amino group or a substituted amino group, присоединенную к атому углерода в положении 6, отличающийс  тем, что краситель формулы А, где X - 4,6-дихлор- или дибромс«ллг-триазин-2-ил , обрабатывают аминосоединением , например аммиаком, с последующим выделением целевого продукта известным приемом.attached to a carbon atom in position 6, characterized in that the dye of formula A, where X is 4,6-dichloro- or dibromos "lg-triazin-2-yl, is treated with an amino compound, such as ammonia, followed by isolation of the target product by a known technique. 2. Способ по п. 1, отличающийс  тем, что процесс ведут в водной среде при рН 5-7 в присутствии акцептора кислоты при температуре 30-50°С.2. A method according to claim 1, characterized in that the process is conducted in an aqueous medium at a pH of 5-7 in the presence of an acid acceptor at a temperature of 30-50 ° C.
SU1803317A 1970-03-02 1971-03-02 Method for preparing active chlorotriazine azo dye SU469262A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB983770 1970-03-02

Publications (1)

Publication Number Publication Date
SU469262A3 true SU469262A3 (en) 1975-04-30

Family

ID=9879731

Family Applications (3)

Application Number Title Priority Date Filing Date
SU1803317A SU469262A3 (en) 1970-03-02 1971-03-02 Method for preparing active chlorotriazine azo dye
SU1625978A SU429593A3 (en) 1970-03-02 1971-03-02 METHOD OF PREPARING THE AMBASSY: Fenledenediamine sulfonic acid. Method 10 consists in condensing cyanuric chloride with a diamine and a dye compound. However, the dyes obtained by this method have a low fixation on cellulose 15 fibers and unsatisfactory durability with respect to wet treatments. a new starting material 20 is used, phenylenediaminodisulfonic acid. The proposed new dye has the general formula where R is hydrogen or alkyl; D is the residue of the amino-amino compound in which molecule nitrogen atoms are bonded to carbon atoms of a homocyclic aromatic radical; X is a residue of a colorless organic acid, the molecule of which contains cellulose-reactive substituents, for example —C1, or X is a dichloro-sym.-triazine group. that one mole of cyanuric chloride is condensed with one mole of a coloring compound of the formula DNHR
SU1629886A SU451254A3 (en) 1970-03-02 1971-03-02 Method for preparing active chlorotriazine azo dye

Family Applications After (2)

Application Number Title Priority Date Filing Date
SU1625978A SU429593A3 (en) 1970-03-02 1971-03-02 METHOD OF PREPARING THE AMBASSY: Fenledenediamine sulfonic acid. Method 10 consists in condensing cyanuric chloride with a diamine and a dye compound. However, the dyes obtained by this method have a low fixation on cellulose 15 fibers and unsatisfactory durability with respect to wet treatments. a new starting material 20 is used, phenylenediaminodisulfonic acid. The proposed new dye has the general formula where R is hydrogen or alkyl; D is the residue of the amino-amino compound in which molecule nitrogen atoms are bonded to carbon atoms of a homocyclic aromatic radical; X is a residue of a colorless organic acid, the molecule of which contains cellulose-reactive substituents, for example —C1, or X is a dichloro-sym.-triazine group. that one mole of cyanuric chloride is condensed with one mole of a coloring compound of the formula DNHR
SU1629886A SU451254A3 (en) 1970-03-02 1971-03-02 Method for preparing active chlorotriazine azo dye

Country Status (13)

Country Link
JP (1) JPS5313652B1 (en)
BE (1) BE763417A (en)
BR (1) BR7101275D0 (en)
CH (2) CH556903A (en)
CS (3) CS165347B2 (en)
DE (2) DE2109879A1 (en)
ES (4) ES388801A1 (en)
FR (2) FR2084040A5 (en)
GB (1) GB1320921A (en)
NL (1) NL7102676A (en)
PL (2) PL82810B1 (en)
SU (3) SU469262A3 (en)
TR (1) TR16783A (en)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4270918A (en) 1978-01-06 1981-06-02 Ciba-Geigy Corporation Reactive dyes, processes for their production and use thereof
CH634341A5 (en) * 1978-02-16 1983-01-31 Ciba Geigy Ag REACTIVE DYES AND THEIR PRODUCTION.
CH635860A5 (en) * 1978-06-16 1983-04-29 Ciba Geigy Ag REACTIVE DYES AND THEIR PRODUCTION.
US4378313B1 (en) * 1979-06-01 1994-05-03 Sumitomo Chemical Co Reactive yellow dye having both monochlorotriazinyl and vinylsulfone type reactive groups
JPS5848672B2 (en) 1979-07-06 1983-10-29 住友化学工業株式会社 Dyeing method for cellulose fibers
US4341699A (en) * 1979-07-13 1982-07-27 Sumitomo Chemical Company, Limited Reactive red dye having both monochlorotriazinyl- and vinylsulfone-type reactive groups
DE2940835A1 (en) * 1979-10-09 1981-04-23 Hoechst Ag, 6000 Frankfurt COPPER COMPLEX-NAPHTHYLAZONAPHTHYL COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR DYING AND PRINTING FIBER MATERIALS AND LEATHER
US4663440A (en) * 1980-06-04 1987-05-05 Sumitomo Chemical Company, Limited Bisazo brown reactive dye
DE3102287A1 (en) * 1981-01-24 1982-09-02 Hoechst Ag, 6000 Frankfurt WATER-SOLUBLE MONOAZO COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS DYES
JPS59228090A (en) * 1983-06-07 1984-12-21 住友化学工業株式会社 Dyeing processing method for cellulose fiber materials
EP0179019B1 (en) * 1984-10-15 1990-05-16 Ciba-Geigy Ag Reactive dyes, their preparation and their use
US5227477A (en) * 1988-06-14 1993-07-13 Sandoz Ltd. Dyes having one or two 2,4- or 4,6-dichloro-5-cyanopyrimidyl groups linked through bridging radicals containing at least two nitrogen atoms to chloro-1,3,5-triazinyl groups
DE3918653C2 (en) * 1988-06-14 2003-01-16 Clariant Finance Bvi Ltd Chromophore compound with heterocyclic reactive residue
DE4408197A1 (en) * 1994-03-11 1995-09-14 Basf Ag Reactive disazo dyes with two anchors based on cyanuric chloride
GB9607182D0 (en) * 1995-05-06 1996-06-12 Zeneca Ltd Chemical process
GB9509295D0 (en) * 1995-05-06 1995-06-28 Zeneca Ltd Chemical process
GB9608505D0 (en) * 1996-04-25 1996-07-03 Zeneca Ltd Compositions processes and uses
CN115466524B (en) * 2022-09-02 2024-07-23 浙江劲光实业股份有限公司 Synthetic method of reactive dye

Also Published As

Publication number Publication date
CS165347B2 (en) 1975-12-22
PL82810B1 (en) 1975-10-31
ES388800A1 (en) 1973-06-01
BR7101275D0 (en) 1973-03-13
SU451254A3 (en) 1974-11-25
DE2109879A1 (en) 1971-10-07
ES388803A1 (en) 1973-05-16
CH556903A (en) 1974-12-13
TR16783A (en) 1973-05-01
PL82823B1 (en) 1975-10-31
CS165348B2 (en) 1975-12-22
FR2084024A5 (en) 1971-12-17
SU429593A3 (en) 1974-05-25
CS164291B2 (en) 1975-11-07
CH557410A (en) 1974-12-31
BE763417A (en) 1971-08-24
JPS5313652B1 (en) 1978-05-11
DE2109900A1 (en) 1971-09-30
NL7102676A (en) 1971-09-06
ES388801A1 (en) 1973-05-16
FR2084040A5 (en) 1971-12-17
GB1320921A (en) 1973-06-20
ES388804A1 (en) 1975-03-16

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