DE2604866A1 - ISOMER-FREE COUPLING TO I-ACID - Google Patents

ISOMER-FREE COUPLING TO I-ACID

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Publication number
DE2604866A1
DE2604866A1 DE19762604866 DE2604866A DE2604866A1 DE 2604866 A1 DE2604866 A1 DE 2604866A1 DE 19762604866 DE19762604866 DE 19762604866 DE 2604866 A DE2604866 A DE 2604866A DE 2604866 A1 DE2604866 A1 DE 2604866A1
Authority
DE
Germany
Prior art keywords
amino
acid
isomer
disulfonaphthalene
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.)
Granted
Application number
DE19762604866
Other languages
German (de)
Other versions
DE2604866C2 (en
Inventor
Horst Dr Jaeger
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Priority to DE19762604866 priority Critical patent/DE2604866C2/en
Priority to CH133877A priority patent/CH623345A5/en
Priority to BR7700698A priority patent/BR7700698A/en
Priority to JP1084577A priority patent/JPS5296630A/en
Priority to GB467677A priority patent/GB1525896A/en
Priority to ES455641A priority patent/ES455641A1/en
Priority to FR7703339A priority patent/FR2340353A1/en
Publication of DE2604866A1 publication Critical patent/DE2604866A1/en
Application granted granted Critical
Publication of DE2604866C2 publication Critical patent/DE2604866C2/en
Expired legal-status Critical Current

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
    • C09B35/02—Disazo dyes
    • C09B35/021—Disazo dyes characterised by two coupling components of the same type
    • C09B35/027—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a hydroxy-amino compound
    • C09B35/029—Amino naphthol
    • 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
    • C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
    • C09B29/28—Amino naphthols
    • C09B29/30—Amino naphtholsulfonic acid
    • 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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0072—Preparations with anionic dyes or reactive dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)

Description

Bayer AktiengesellschaftBayer Aktiengesellschaft

26048612604861

Zentralbereich Patente. Marken und LizenzenCentral Patents Department. Trademarks and licenses

509 Leverkusen. Bayerwerk509 Leverkusen. Bayerwerk

Jo/PtJo / Pt

6. Feb. 1976Feb 6, 1976

Isomerenfreie Kupplung auf I-SäureIsomer-free coupling to I-acid

Gegenstand der Erfindung ist ein Verfahren zur Herstellung von isomerenfreien ο-Kupplungsprodukten der I-Säure der allgemeinen FormelThe invention relates to a process for the preparation of isomer-free ο-coupling products of the I-acid of the general formula

OHOH

(D(D

worin D den Rest einer Diazo- oder Tetrazokomponente undwherein D is the remainder of a diazo or tetrazo component and η 1 oder 2 bedeuten, dadurch gekennzeichnet, daß man diazotierteη mean 1 or 2, characterized in that one diazotized

oder tetrazotierte Amine der Formelor tetrazotized amines of the formula

D--NH,D - NH,

2 η2 η

(II)(II)

worin D und η die angegebene Bedeutung haben, in bekannterwhere D and η have the meaning given, in known

Le A 16 996Le A 16 996

709832/095 9709832/095 9

Weise mit 1-Oxy-6-amino-3,5-disulfonaphthalin zu den Farbstoffen der FormelWay with 1-oxy-6-amino-3,5-disulfonaphthalene to the dyes the formula

D-D-

-N=N-N = N

OHOH

■ NH,■ NH,

(III)(III)

kuppelt und diese mit Säuren behandelt.coupled and treated with acids.

1-Oxy-6-amino-3,5-disulfonaphthalin und die Farbstoffe (III) sind beispielsweise aus den Deutschen Patentschriften 80 878, 88 846, 92 469, 92 708, 177 178, 198 102, 117 950, 169 732 bekannt.1-Oxy-6-amino-3,5-disulfonaphthalene and the dyes (III) are known, for example, from German patents 80 878, 88 846, 92 469, 92 708, 177 178, 198 102, 117 950, 169 732.

Geeignete Amine (il) sind beispielsweise: Suitable amines (II) are, for example:

1-Amino-2-sulfobenzol, 1-Amino-3-sulfobenzol, 1-Amino-4-sulfobenzol, 1-Amino-2,4-disulfobenzol, 1-Amino-2,5-disulfobenzol, 1-Amino-2-methoxy-5-sulfobenzol, 1-Amino-2-methoxy-4-sulfobenzol, 1-Amino-4-methoxy-2,5-disulfobenzol, 1-Amino-4-amino-2,5-disulfobenzol, i-Amino-2-methoxybenzol, 1-Amino-2-sulfo-4-methylbenzol, 1-Amino-2-sulfo-4-chlorbenzol, i-Amino-2-sulfo-4,5-dichlorbenzol, 1-Amino-2-sulfo-4-nitrobenzol, 1-Amino-2-sulfo-4,6-dimethylbenzol, Anilin, o-Toluidin, 1-Amino-2-sulfo-4,5-dimethylbenzol, 1-Amino-4-sulfonaphthalin, 1-Amino-2,4-disulfonaphthalin, 1-Amino-2,5,7-trisulfonaphthalin, 1-Amino-2,4,6-trisulfonaphthalin, 2-Amino-1-sulfonaphthalin, 2-Amino-1,5-disulfonaphthalin, 2-Amino-3,6-disulfonaphthalin, 2-Amino-4,8-disulfonaphthalin, 2-Amino-6,8-disulfonaphthalin, 2-Amino-1,5,7-trisulfonaphthalin, 2-Amino-3,6,8-trisulfonaphthalin, 2-Amino-4,8-disulf o-6-nitronaphthalin, 1 -Amino^-nitro-e-sulf onaphthalin, 2-Amino-6-sulfonaphthalin, 2-Amino-8-sulfonaphthalin, 1-Amino-6-sulfonaphthalin, Dehydrothio-p-toluidinsulfonsäure, Dehydrothio-p-toluidindisulfonsäure, 4'-Aminoazobenzol-4-sul-1-Amino-2-sulfobenzene, 1-Amino-3-sulfobenzene, 1-Amino-4-sulfobenzene, 1-Amino-2,4-disulfobenzene, 1-Amino-2,5-disulfobenzene, 1-Amino-2- methoxy-5-sulfobenzene, 1-amino-2-methoxy-4-sulfobenzene, 1-amino-4-methoxy-2,5-disulfobenzene, 1-amino-4-amino-2,5-disulfobenzene, i-amino 2-methoxybenzene, 1-amino-2-sulfo-4-methylbenzene, 1-amino-2-sulfo-4-chlorobenzene, i-amino-2-sulfo-4,5-dichlorobenzene, 1-amino-2-sulfo- 4-nitrobenzene, 1-amino-2-sulfo-4,6-dimethylbenzene, aniline, o-toluidine, 1-amino-2-sulfo-4,5-dimethylbenzene, 1-amino-4-sulfonaphthalene, 1-amino 2,4-disulfonaphthalene, 1-amino-2,5 , 7-trisulfonaphthalene, 1-amino-2,4,6-trisulfonaphthalene, 2-amino-1-sulfonaphthalene, 2-amino-1,5-disulfonaphthalene, 2- Amino-3,6-disulfonaphthalene, 2-amino-4,8-disulfonaphthalene, 2-amino-6,8-disulfonaphthalene, 2-amino-1,5,7-trisulfonaphthalene, 2-amino-3,6,8- trisulfonaphthalene, 2-amino-4,8-disulf o-6-nitronaphthalene, 1-amino ^ -nitro-e-sulfonaphthalene, 2-amino-6-sulfonaphthalene, 2-amino-8-sulfonaphthalene, 1-amino-6 -sulfone aphthalene, dehydrothio-p-toluidinesulfonic acid, dehydrothio-p-toluidinedisulfonic acid, 4'-aminoazobenzene-4-sul-

Le Le A A. 16 99616 996

—2——2—

709832/0959709832/0959

260486S260486S

fonsäure, 4'-Aminoazobenzol-2',4-disulfonsäure, 4,4'-Diaminobiphenyl, 3,3'-Dichlor-4,4'-diaminobiphenyl, 4,4'-Diamino-3,3'-dimethoxybiphenyl, (4,4' -Diaminobiphenylen-3 > 3') -bis-glykolsäure, 4,4'-Diaminobiphenyl-3,3'-CUCaPbOnSaUTe, 4,4'-Diaminodiphenylamin-2-sulfonsäure, 4,4'-Diamino-biphenyl-2,2'-disulfonsäure, 4,4'-Diaminobiphenyl-3,3'-disulfonsäure, 4-Amino-1-phenoxybenzol-2-sulfonsäure, 4,4'-Diaminodiphenyläther-2-sulfonsäure, 4'-Amino-2,3'-dimethylazobenzol, 4-(4,8-Disulfonaphthalin-2-azo-2'-toluol-5'-azo)-o-toluidin, 6-Chlor-4'-amino-2,2'-dimethylazobenzol-4-sulfonsäure, 4'-p-Aminobenzamido-4-hydroxyazobenzol-3-carbonsäure, 4'-Amino-4-hydroxyazobenzol-3-carbonsäure, 4' -Amino-4- (5-sulfonaphthol/r1,2-d7triazol-2-yl) stilben-2,2'-disulfonsäure.fonsäure, 4'-aminoazobenzene-2 ', 4-disulfonic acid, 4,4'-diaminobiphenyl, 3,3'-dichloro-4,4'-diaminobiphenyl, 4,4'-diamino-3,3'-dimethoxybiphenyl, ( 4,4'-diaminobiphenylen-3> 3 ') -bis-glycolic acid, 4,4'-diaminobiphenyl-3,3'-CUCaPbOnSaUTe, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diamino-biphenyl -2,2'-disulfonic acid, 4,4'-diaminobiphenyl-3,3'-disulfonic acid, 4-amino-1-phenoxybenzene-2-sulfonic acid, 4,4'-diaminodiphenyl ether-2-sulfonic acid, 4'-amino 2,3'-dimethylazobenzene, 4- (4,8-disulfonaphthalene-2-azo-2'-toluene-5'-azo) -o-toluidine, 6-chloro-4'-amino-2,2'-dimethylazobenzene -4-sulfonic acid, 4'-p-aminobenzamido-4-hydroxyazobenzene-3-carboxylic acid, 4'-amino-4-hydroxyazobenzene-3-carboxylic acid, 4'-amino-4- (5-sulfonaphthol / r 1,2- d7triazol-2-yl) stilbene-2,2'-disulfonic acid.

Geeignete Säuren sind beispielsweise Salzsäure und Schwefelsäure. Die Konzentration kann in weiten Grenzen schwanken, vorzugsweise wird mit einer 5-10 %igen wäßrigen Säure gearbeitet. Die Säurebehandlung wird im Temperaturbereich von 50 - 130 0C, vorzugsweise von 90 - 100 0C ausgeführt. Nach der Behandlung mit Säure werden die Farbstoffe (i) in üblicher Weise durch Absaugen oder Aussalzen isoliert. Die Farbstoffe (I) können als solche verwendet oder weiter umgesetzt werden, bei spielsweise mit Phosgen zu I-Säureharnstoff-Farbstoffen oder mit faserreaktiven Acylverbindungen zu Reaktivfarbstoffen. Suitable acids are, for example, hydrochloric acid and sulfuric acid. The concentration can fluctuate within wide limits; a 5-10% strength aqueous acid is preferably used. The acid treatment is in the temperature range of 50 - 100 run 0 C - 130 0 C, preferably from 90th After the treatment with acid, the dyes (i) are isolated in the customary manner by suction filtration or salting out. The dyes (I) can be used as such or reacted further , for example with phosgene to form I-acid urea dyes or with fiber- reactive acyl compounds to form reactive dyes.

Beispiel 1example 1

28,3 g 1-Amino-2,5-disulfo-4-methoxybenzol werden in 500 ml Eiswasser angerührt und mit 28 ml konz. HCl und 70 ml 10 96iger Natriumnitritlösung versetzt. Die Suspension der Diazoverbindung wird portionsweise in eine Vorlage aus 500 ml Wasser, 28 g Natriumbicarbonat und 31,9 g 1-Oxy-6-amino-3,5-disulfonaphthalin eingetragen. Nach der Kupplung erhält man einen klaren gelbstichig roten Farbstoff, der teilweise ausgefallen ist. Man 28.3 g of 1-amino-2,5-disulfo-4-methoxybenzene are stirred in 500 ml of ice water and concentrated with 28 ml. HCl and 70 ml of 10 96% sodium nitrite solution are added. The suspension of the diazo compound is introduced in portions into a receiver of 500 ml of water, 28 g of sodium bicarbonate and 31.9 g of 1-oxy-6-amino-3,5-disulfonaphthalene. After coupling, a clear yellowish red dye is obtained, some of which has precipitated. Man

Le A 16 996 -3- Le A 16 996 -3-

709832/0959709832/0959

setzt nun soviel kcmz. Salzsäure zu, daß eine 2n-Salzsäure resultiert und erwärmt 1 Stunde auf 100 0C, wobei der Farbstoff in Lösung geht. Nach dem Abkühlen wird der Farbstoff durch Salzzugabe vollständig abgeschieden.now puts so much kcmz. Hydrochloric acid to that a 2N hydrochloric acid results and heated for 1 hour to 100 0 C, whereby the dye goes into solution. After cooling, the dye is completely deposited by adding salt.

Nach dem Absaugen und Trocknen erhält man den Farbstoff, der in Form der freien Säure der FormelAfter filtering off with suction and drying, the dye is obtained in the form of the free acid of the formula

entspricht, als rotes, in Wasser leicht lösliches Pulver.corresponds to, as a red, easily soluble in water powder.

Beispiel 2Example 2

30,3 g 2-Amino-1,5-disulfonaphthalin werden nach den Angaben von Beispiel 1 diazotiert und auf i-Oxy-ö-amino-S^-disulfonaphthalin gekuppelt. Nach der Kupplung erhält man ein orangefarbenes Produkt, das teilweise ausgefallen ist. Man setzt der Suspension soviel konz. Schwefelsäure zu, daß eine 10 %ige Säure resultiert und erwärmt 1 Stunde auf 100 0C. Nach dem Abkühlen und Neutralisieren wird der Farbstoff durch Salzzugabe vollständig abgeschieden. Nach dem Absaugen und Trocknen erhält man den Farbstoff, der in Form der freien Säure der Formel30.3 g of 2-amino-1,5-disulfonaphthalene are diazotized as described in Example 1 and coupled to i-oxy-δ-amino-S ^ -disulfonaphthalene. After coupling, an orange-colored product is obtained, some of which has precipitated. One sets the suspension so much conc. Sulfuric acid to the result that a 10% strength acid results and the mixture is heated to 100 ° C. for 1 hour. After cooling and neutralization, the dye is completely separated off by adding salt. After filtering off with suction and drying, the dye is obtained in the form of the free acid of the formula

Le A 16 996Le A 16 996

-4--4-

709832/0959709832/0959

entspricht,als orangefarbenes, in Wasser leicht lösliches Pulver.corresponds to, as an orange-colored, easily soluble in water Powder.

Le A 16 996Le A 16 996

-5--5-

709832/0959709832/0959

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von isomerenfreien ο-Kupplungsprodukten des 1 -Oxy-6-amino-:5-sulfonaphthalins, dadurch gekennzeichnet, daß man ein diazotiertes oder tetrazotiertes Amin der FormelProcess for the production of isomer-free ο coupling products of 1-oxy-6-amino-: 5-sulfonaphthalene, characterized in that that one is a diazotized or tetrazotized amine of the formula D-D- -NH,-NH, worin D den Rest einer Diazo- oder Tetrazokomponente und η 1 oder 2 bedeuten, mit 1-0xy-6-amino-3,5-disulfobenzol zu einer Verbindung der Formelwhere D is the residue of a diazo or tetrazo component and η is 1 or 2, with 1-0xy-6-amino-3,5-disulfobenzene to a compound of the formula kuppelt und diese mit Säure behandelt.and treats it with acid. Le A Le A 16 16 996996 -6--6- 709832/0959
ORIGINAL INSPECTED 709832/0959
ORIGINAL INSPECTED
DE19762604866 1976-02-07 1976-02-07 Production of isomer-free o-coupling products of 1-oxy-6-amino-3-sulfonaphthalius Expired DE2604866C2 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DE19762604866 DE2604866C2 (en) 1976-02-07 1976-02-07 Production of isomer-free o-coupling products of 1-oxy-6-amino-3-sulfonaphthalius
CH133877A CH623345A5 (en) 1976-02-07 1977-02-03 Process for the preparation of isomer-free o-coupling products of 1-hydroxy-6-amino-3-sulphonaphthalene
BR7700698A BR7700698A (en) 1976-02-07 1977-02-04 PROCESS FOR THE PREPARATION OF ISOMEROS-FREE O-COPULATION PRODUCTS
JP1084577A JPS5296630A (en) 1976-02-07 1977-02-04 Process for production of coupling products nonncontaining isomer of 11hydroxyy66aminoo 33sulphonaphthalene
GB467677A GB1525896A (en) 1976-02-07 1977-02-04 Isomer-free coupling of i-acid
ES455641A ES455641A1 (en) 1976-02-07 1977-02-04 Isomer-free coupling of i-acid
FR7703339A FR2340353A1 (en) 1976-02-07 1977-02-07 PROCESS FOR MAKING, WITHOUT ISOMERS, COPULATION PRODUCTS OF 1-HYDROXY-6-AMINO-3-SULFONAPHTALENE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19762604866 DE2604866C2 (en) 1976-02-07 1976-02-07 Production of isomer-free o-coupling products of 1-oxy-6-amino-3-sulfonaphthalius

Publications (2)

Publication Number Publication Date
DE2604866A1 true DE2604866A1 (en) 1977-08-11
DE2604866C2 DE2604866C2 (en) 1984-01-19

Family

ID=5969341

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19762604866 Expired DE2604866C2 (en) 1976-02-07 1976-02-07 Production of isomer-free o-coupling products of 1-oxy-6-amino-3-sulfonaphthalius

Country Status (7)

Country Link
JP (1) JPS5296630A (en)
BR (1) BR7700698A (en)
CH (1) CH623345A5 (en)
DE (1) DE2604866C2 (en)
ES (1) ES455641A1 (en)
FR (1) FR2340353A1 (en)
GB (1) GB1525896A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE117950C (en) *
DE92469C (en) *

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NICHTS-ERMITTELT *

Also Published As

Publication number Publication date
BR7700698A (en) 1977-10-11
CH623345A5 (en) 1981-05-29
JPS5296630A (en) 1977-08-13
ES455641A1 (en) 1978-01-01
DE2604866C2 (en) 1984-01-19
FR2340353B1 (en) 1981-06-19
GB1525896A (en) 1978-09-20
FR2340353A1 (en) 1977-09-02

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