DE2252943A1 - DIHYDROXYPYRIDINE DYES - Google Patents

DIHYDROXYPYRIDINE DYES

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Publication number
DE2252943A1
DE2252943A1 DE19722252943 DE2252943A DE2252943A1 DE 2252943 A1 DE2252943 A1 DE 2252943A1 DE 19722252943 DE19722252943 DE 19722252943 DE 2252943 A DE2252943 A DE 2252943A DE 2252943 A1 DE2252943 A1 DE 2252943A1
Authority
DE
Germany
Prior art keywords
dyes
radical
carbon atoms
optionally substituted
parts
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.)
Pending
Application number
DE19722252943
Other languages
German (de)
Inventor
Johannes Dr Dehnert
Gerhard Dr Gnad
Gunther Dr Lamm
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DE19722252943 priority Critical patent/DE2252943A1/en
Priority to AU61422/73A priority patent/AU6142273A/en
Priority to CH1498773A priority patent/CH584263A5/xx
Priority to FR7338080A priority patent/FR2204662B1/fr
Priority to AR25073073A priority patent/AR198703A1/en
Priority to IT5338173A priority patent/IT997709B/en
Priority to BE137106A priority patent/BE806566A/en
Priority to GB4991473A priority patent/GB1443808A/en
Priority to DD17431973A priority patent/DD108763A5/xx
Priority to BR842373A priority patent/BR7308423D0/en
Priority to JP12085373A priority patent/JPS5026565B2/ja
Publication of DE2252943A1 publication Critical patent/DE2252943A1/en
Pending legal-status Critical Current

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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
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

Unser Zeichen: O.Z. 29 49t Bg/Ja^^ 67OO Ludwigshafen, 27. 10. 1972Our reference: O.Z. 29 49t Bg / Yes ^^ 67OO Ludwigshafen, October 27, 1972

DihydroxypyridinfarbstoffeDihydroxypyridine dyes

Die Erfindung betrifft Farbstoffe der Formel IThe invention relates to dyes of the formula I.

CH^,CH ^,

H0^N>0H H0 ^ N> 0H

in der X einen gegebenenfalls substituierten Alkylaminorest mit 3 bis 12 C-Atomen, einen gegebenenfalls substituierten Alkoxyrest mit insgesamt mehr als 4 C-Atomen oder einen gegebenenfalls substituierten Cycloalkylaminorest mit 5 bis 10 Ringgliedern bedeutet. ,in which X is an optionally substituted alkylamino radical having 3 to 12 carbon atoms, an optionally substituted alkoxy radical with a total of more than 4 carbon atoms or an optionally substituted cycloalkylamino radical with 5 to 10 ring members means. ,

Alkylaminoreste X sind beispielsweise die geradkettigen oder verzweigten Alkylaminoreste mit J bis 12 C-Atomen die z„ B. noch durch Hydroxy oder Alkoxy substituiert sein können.Alkylamino radicals X are, for example, the straight-chain or branched alkylamino radicals with J to 12 carbon atoms which can, for example, also be substituted by hydroxy or alkoxy.

Im einzelnen seien beispielsweise Propyl-, Butyl-, Hexyl-, ß-Ä'thylhexyl-, Decyl-, Dodecyl-, Methoxypropyl-, Ä'thoxypropyl-, i-Propoxypropyl-, Hexoxypropyl-, ß-Ä'thylhexoxypropyl-, tu-Hydroxybutyl-, io-Hydroxyhexyl- oder l,5,5-Trimethyl-5-hydroxypentylarnino genannt.Specifically, for example, propyl, butyl, hexyl, ß-Ä'thylhexyl-, decyl, dodecyl, methoxypropyl, Ä'thoxypropyl- i-propoxypropyl-, hexoxypropyl-, ß-ethylhexoxypropyl-, tu-hydroxybutyl-, io-hydroxyhexyl- or 1,5,5-trimethyl-5-hydroxypentylamino called.

Cycloalkylaminoreste sind z. B. die Cyclopentyl-, Cyclohexyl-, Methylejroiohexyl-, Cycloheptyl- oder Cyclooctylaminogruppe: , sowie die bioyclischen Reste der FormelCycloalkylamino radicals are, for. B. the cyclopentyl, cyclohexyl, methylejroiohexyl, cycloheptyl or cyclooctylamino group:, as well as the bioyclic radicals of the formula

HM 4 f y > HN4 / > oder HNHM 4 f y> HN4 /> or HN

Substituierte Alkoxyreste sind beispielsweise die Reste der Formeln 0-(CH2) ^ OH, O(CH2)6 OH oder (OCH2 CHg)n OR, wobei η 2, -J oder 4 ist und R Alkyl mit 1 bis 4 C-Atomen bedeutet. EinzelneSubstituted alkoxy radicals are, for example, the radicals of the formulas 0- (CH 2 ) ^ OH, O (CH 2 ) 6 OH or (OCH 2 CHg) n OR, where η 2, -J or 4 and R is alkyl with 1 to 4 C - atoms means. Separate

656/72 _ 2 -656/72 _ 2 -

409818/1024409818/1024

- 2 - U.Z. 29 495- 2 - U.Z. 29 495

? ? S / 9 L Ί? ? S / 9 L Ί

Reste sind ζ. B. OCH2 CH C^ , (ÖCH^CH^;,. OCE-^, (OCH2CHLeftovers are ζ. B. OCH 2 CH C ^, (OCH ^ CH ^;,. OCE- ^, (OCH 2 CH

(0CH2CH2)2 OC4H9, (OCH2CH2) OCH , (OCH2CH2), OC3H5 oder(OCH 2 CH 2 ) 2 OC 4 H 9 , (OCH 2 CH 2 ) OCH, (OCH 2 CH 2 ), OC 3 H 5 or

CH2)^ OC4HCH 2 ) ^ OC 4 H

Zur Herstellung der neuen Farbstoffe kann man Diazoverbindungen von Aminen der Formel IIDiazo compounds of amines of the formula II can be used to prepare the new dyes

mit 2,6-Dihydroxy-3-cyan-4-methylpyridin umsetzen. Diazotierung und Kupplung erfolgen dabei wie üblich.react with 2,6-dihydroxy-3-cyano-4-methylpyridine. Diazotization and coupling take place as usual.

Von besonderer technischer Bedeutung sind die Farbstoffe der Formel IaThe dyes of the formula Ia are of particular industrial importance

-r o 1 d, -r o 1 d,

in derin the

Y einen Alkylrest mit 6 bis 12 C-Atomen, der durch Sauerstoffatome unterbrochen und durch Hydroxy substituiert sein kann, oder einen Cycloalkylrest mit 5 °is 10 Ringgliedern bedeutet.Y is an alkyl radical with 6 to 12 carbon atoms, replaced by oxygen atoms interrupted and substituted by hydroxy, or denotes a cycloalkyl radical with 5 ° to 10 ring members.

Der Rest -CONHY steht darüber hinaus bevorzugt in p-Stellung zur Diazogruppierung.The -CONHY radical is also preferably in the p-position Diazo grouping.

Die neuen Farbstoffe sind gelb und eig-nen sich vorzugsweise zum Färben von synthetischen linearen Polyestern, wobei man grünstichig gelbe Färbungen mit hervorragenden Echtheiten erhält,The new dyes are yellow and are preferably suitable for dyeing synthetic linear polyesters, whereby one receives greenish yellow dyeings with excellent fastness properties,

In den folgenden Beispielen beziehen sich Angaben über Teile und Prozente auf das Gewicht.In the following examples, parts and percentages are based on weight.

4098 18/1024 - 3 -4098 18/1024 - 3 -

- 3 - - o.z. 29 495- 3 - - o.a. 29 495

22523432252343

Beispiel 1example 1

372 Teile 4-Aminobenzoesäure-2'-äthylhexylamid werden mit 4600 Teilen Wasser und 6OO Raumteilen 15 $iger Salzsäure versetzt und bis zur Lösung gerührt. Dann setzt man weitere 500 Raumteile 15 $iger Salzsäure und. danach soviel Eis und Wasser zu, daß das Volumen des Gemisches etwa 7500 Raumteile und die Temperatur etwa 5 bis 80C beträgt. Man läßt rasch 450 Raumteile einer 23 Jöigen Natriumnitritlösung zulaufen und rührt die meist klare Lösung etwa JO bis 60 Minuten bei etwa 5 - 12°C. Die Diazoniumsalzlösung gibt man zu einer auf 0 bis 5 C abgekühlten Lösung von 226 Teilen 2i6-Dihydroxy-3-cyan-methylpyridin in etwa 8OOO Teilen Wasser und 68 Teilen Natronlauge. Während der Kupplung setzt man etwa J500 Teile Soda so zu, daß der pH-Wert des Gemisches stets größer als 6,5 ist. Nach beendeter Kupplung wird die wäßrige Farbstoffdispersion bei einem pH-Wert von etwa 6 bis 9 auf 80 C aufgeheizt. Man rührt das Gemisch etwa 1 Stunde bei dieser Temperatur, saugt dann ab und wäscht mit Wasser. Man erhält etwa 600 Teile eines kristalliner. Pulvers der Formel372 parts of 4-aminobenzoic acid-2'-ethylhexylamide are mixed with 4600 parts of water and 600 parts by volume of 15% hydrochloric acid and the mixture is stirred until it dissolves. Then you put another 500 parts by volume of 15 $ hydrochloric acid and. thereafter so much ice and water such that the volume of the mixture is about 7500 parts by volume and the temperature is about 5 to 8 0 C. 450 parts by volume of a 23% sodium nitrite solution are quickly run in and the usually clear solution is stirred for about 50 to 60 minutes at about 5-12 ° C. The diazonium salt solution is added to a solution, cooled to 0 to 5 ° C., of 226 parts of 2 i 6-dihydroxy-3-cyano-methylpyridine in about 800 parts of water and 68 parts of sodium hydroxide solution. During the coupling, about 500 parts of soda are added so that the pH of the mixture is always greater than 6.5. After coupling has ended, the aqueous dye dispersion is heated to 80.degree. C. at a pH of about 6 to 9. The mixture is stirred for about 1 hour at this temperature, then filtered off with suction and washed with water. About 600 parts of a crystalline are obtained. Powder of formula

0 CH,-(CH2U-CH-CH2-NH-C-0 CH, - (CH 2 U-CH-CH 2 -NH-C-

das sich in Dimethylformamid mit gelber Farbe löst und PoIyäthylenterephthalatgewebe in grünstichig gelben Tönen mit ausgezeichneter Lichtechtheit färbt.which dissolves in dimethylformamide with a yellow color and polyethylene terephthalate fabric dyes in greenish yellow tones with excellent lightfastness.

CH,CH, CN
/CN
/ N=N- / .
\__'v N = N- /.
\ __ 'v %- OH
r ' % - OH
r ' HOHO II.

409818/1024409818/1024

22b294322b2943

Analog zur in Beispiel 1 beschriebenen Arbeitsweise können die in den folgenden Tabellen genannten Farbstoffe hergestellt werden: The dyes mentioned in the following tables can be prepared analogously to the procedure described in Example 1:

TabelleTabel

CHCH

R-NH-C-R-NH-C-

A-N=N-A-N = N-

HOHO

CHCH

C4H9(H)-C 4 H 9 (H) -

Farbton der Färbungen auf Polyethylenterephthalat Color shade of the dyeings on polyethylene terephthalate

grünstichig gelbgreenish yellow

C5Hn(Ii)-c6Hl3(n)-C 5 H n (Ii) - c 6 H l3 (n) -

C2H5 H9C4 CH-O C3H6 C 2 H 5 H 9 C 4 CH-O C 3 H 6

CH t CH t

CHCH

-CH-CHo-CHo-CHo-CCL-CH-CHo-CHo-CHo-CCL

dd dd d \d \

CH,CH,

409818/1024409818/1024

1414th

CH,CH,

CH-CH-

5 - O.Z. 29 4955 - O.Z. 29 495

grünstichig gelbgreenish yellow

Die Farbstoffe, bei denen der Rest CONHR in o- oder m-Stellung zur Azobrücke steht, weichen in ihren Eigenschaften in der Regel nur gering von den Farbstoffen mit p-ständiger Gruppierung ab.The dyes in which the radical CONHR is in the o- or m-position to the Azo Bridge, their properties soften in the As a rule, it differs only slightly from the dyes with a group in the p position.

4Q98 18/10244Q98 18/1024

O. Z. 29 495O. Z. 29,495

Tabelle 2Table 2

18 -(0-CH0-CH0)o-0CH,18 - (0-CH 0 -CH 0 ) o -0CH,

19 -(0-CH2-CHg)2-O-C2H.19 - (0-CH 2 -CHg) 2 -OC 2 H.

20 -(0-CH2-CH2)2-O-C4H20 - (O -CH 2 -CH 2 ) 2 -OC 4 H

21 -0-CH2-CH-C4H9 21 -0-CH 2 -CH-C 4 H 9

22 -(0-CH2-CH2),-0-CH,22 - (0-CH 2 -CH 2 ), - 0-CH,

23 -(0-CH2-CH2) -0-C2H23 - (O-CH 2 -CH 2 ) -0-C 2 H

Auch bei den Farbstoffen der Tabelle 2 unterscheiden sich die Farbstoffe mit o-, m- oder p-ständiger Estergruppe nur wenig*Even with the dyes in Table 2, the dyes with o, m or p ester groups differ only slightly *

409818/1024409818/1024

Claims (1)

PatentansprücheClaims in derin the X einen gegebenenfalls substituierten Alkylaminorest mit 3 bis 12 C-Atomen, einen gegebenenfalls substituierten Alkoxyrest mit insgesamt mehr als 4 C-Atomen oder einen gegebenenfalls substituierten Cycloalkylamifiorest mit 5 bis 10 Ringgliedern bedeutet.X is an optionally substituted alkylamino radical with 3 up to 12 carbon atoms, an optionally substituted alkoxy radical with a total of more than 4 carbon atoms or one optionally substituted Cycloalkylamifiorest with 5 to 10 ring members means. 2. Farbstoffe gemäß Anspruch 1 der Formel2. Dyestuffs according to Claim 1 of the formula T
Ia , T
Yes, in derin the Y einen Alkylrest mit 6 bis 12 C-Atomen, der durch Sauerstoffatome unterbrochen und durch Hydroxy substituiert sein kann, oder einen Cycloalkylrest mit 5 bis 10 Ringgliedern bedeutet.Y is an alkyl radical with 6 to 12 carbon atoms, replaced by oxygen atoms interrupted and substituted by hydroxy, or a cycloalkyl radical with 5 to 10 ring members means. Verfahren zur Herstellung von Farbstoffen gemäß Anspruch 1, dadurch gekennzeichnet, daß man Diazoverbindungen von Aminen der FormelProcess for the preparation of dyes according to Claim 1, characterized in that diazo compounds of amines of the formula mit 2,6-Dihydroxy-j5-cy"an-4-methylpyridin kuppelt.couples with 2,6-dihydroxy-j5-cy "to -4-methylpyridine. -. 8 -409818/1024-. 8 -409818/1024 O.ζ. 29 495O.ζ. 29 495 22529A322529A3 4. Die Verwendung der Farbstoffe gemäß Anspruch 1 oder 2 zum Färben von synthetischen linearen Polyestern.4. The use of the dyes according to claim 1 or 2 for dyeing synthetic linear polyesters. Badische Anilin- & Soda-Fabrik AGBadische Anilin- & Soda-Fabrik AG 409818/1024409818/1024
DE19722252943 1972-10-28 1972-10-28 DIHYDROXYPYRIDINE DYES Pending DE2252943A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
DE19722252943 DE2252943A1 (en) 1972-10-28 1972-10-28 DIHYDROXYPYRIDINE DYES
AU61422/73A AU6142273A (en) 1972-10-28 1973-10-16 Dihydroxypyidine dyes
CH1498773A CH584263A5 (en) 1972-10-28 1973-10-24
FR7338080A FR2204662B1 (en) 1972-10-28 1973-10-25
AR25073073A AR198703A1 (en) 1972-10-28 1973-10-26 DIHYDROXYPYRIDINE COLORS
IT5338173A IT997709B (en) 1972-10-28 1973-10-26 DIHYDROXYPYRIDINE DYES
BE137106A BE806566A (en) 1972-10-28 1973-10-26 DIHYDROXYPYRIDINE COLORANTS
GB4991473A GB1443808A (en) 1972-10-28 1973-10-26 Azo dyes containing dihydroxypyridine residues
DD17431973A DD108763A5 (en) 1972-10-28 1973-10-26
BR842373A BR7308423D0 (en) 1972-10-28 1973-10-26 COLORING PROCESS OF PYRIDINE DI-HYDROXY
JP12085373A JPS5026565B2 (en) 1972-10-28 1973-10-29

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19722252943 DE2252943A1 (en) 1972-10-28 1972-10-28 DIHYDROXYPYRIDINE DYES

Publications (1)

Publication Number Publication Date
DE2252943A1 true DE2252943A1 (en) 1974-05-02

Family

ID=5860290

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19722252943 Pending DE2252943A1 (en) 1972-10-28 1972-10-28 DIHYDROXYPYRIDINE DYES

Country Status (11)

Country Link
JP (1) JPS5026565B2 (en)
AR (1) AR198703A1 (en)
AU (1) AU6142273A (en)
BE (1) BE806566A (en)
BR (1) BR7308423D0 (en)
CH (1) CH584263A5 (en)
DD (1) DD108763A5 (en)
DE (1) DE2252943A1 (en)
FR (1) FR2204662B1 (en)
GB (1) GB1443808A (en)
IT (1) IT997709B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4167509A (en) * 1975-12-17 1979-09-11 Imperial Chemical Industries Limited Water soluble cationic azo dyestuffs
US4514226A (en) * 1981-03-25 1985-04-30 Basf Aktiengesellschaft Monoazo pyridone colorants

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5637391A (en) * 1979-08-29 1981-04-11 Tokyo Seikou Seni Roopu Kk Fiber rope

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1489492A (en) * 1965-08-13 1967-07-21 Cassella Farbwerke Mainkur Ag New Water Insoluble Azo Dyes and Their Preparation
DE1644122B2 (en) * 1967-09-01 1976-07-15 Cassella Farbwerke Mainkur Ag, 6000 Frankfurt SULPHONIC ACID AND CARBONIC ACID GROUP-FREE, HYDRO-INSOLUBLE MONOAZO DYES AND PROCESS FOR THEIR PRODUCTION
GB1360635A (en) * 1971-04-05 1974-07-17 Ici Ltd Paints and printing inks
BE789191A (en) * 1971-09-24 1973-03-22 Cassella Farbwerke Mainkur Ag WATER INSOLUBLE MONO-AZOIC COLORANTS
BE791584A (en) * 1971-11-18 1973-05-17 Cassella Farbwerke Mainkur Ag SYNTHETIC FIBROUS DYES

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4167509A (en) * 1975-12-17 1979-09-11 Imperial Chemical Industries Limited Water soluble cationic azo dyestuffs
US4514226A (en) * 1981-03-25 1985-04-30 Basf Aktiengesellschaft Monoazo pyridone colorants

Also Published As

Publication number Publication date
BE806566A (en) 1974-04-26
FR2204662A1 (en) 1974-05-24
JPS4976935A (en) 1974-07-24
AU6142273A (en) 1975-04-17
AR198703A1 (en) 1974-07-15
JPS5026565B2 (en) 1975-09-02
CH584263A5 (en) 1977-01-31
IT997709B (en) 1975-12-30
DD108763A5 (en) 1974-10-05
FR2204662B1 (en) 1976-11-19
GB1443808A (en) 1976-07-28
BR7308423D0 (en) 1974-08-29

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