FR2554455A1 - NOVEL MONOAZOIC COMPOUNDS, THEIR PREPARATION AND THEIR USE AS COLORANTS - Google Patents
NOVEL MONOAZOIC COMPOUNDS, THEIR PREPARATION AND THEIR USE AS COLORANTS Download PDFInfo
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- FR2554455A1 FR2554455A1 FR8416626A FR8416626A FR2554455A1 FR 2554455 A1 FR2554455 A1 FR 2554455A1 FR 8416626 A FR8416626 A FR 8416626A FR 8416626 A FR8416626 A FR 8416626A FR 2554455 A1 FR2554455 A1 FR 2554455A1
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- alkyl
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- 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
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)
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- Organic Chemistry (AREA)
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- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
LA PRESENTE INVENTION A POUR OBJET LES COMPOSES MONOAZOIQUES DE FORMULE I: (CF DESSIN DANS BOPI) DANS LAQUELLE D REPRESENTE UNE COMPOSANTE DE DIAZOTATION, R REPRESENTE L'HYDROGENE, LE CHLORE OU LE BROME OU UN GROUPE ALKYLE, ALCOXY OU ALCOXYETHOXY, R REPRESENTE L'HYDROGENE, UN GROUPE ALKYLE, ALKYL-CARBONYLAMINO, ALCOXYALKYL-CARBONYLAMINO, FLUORO-, CHLORO- OU BROMO-ALKYL-CARBONYLAMINO, HYDROXY-ALKYL-CARBONYL-AMINO, ALCOXY-CARBONYLAMINO, ALCOXY-ALCOXY-CARBONYLAMINO OU ALKYL-SULFONYLAMINO, R REPRESENTE L'HYDROGENE OU UN GROUPE ALKYLE SUBSTITUE OU NON SUBSTITUE, A REPRESENTE UN GROUPE ALKYLENE LINEAIRE OU RAMIFIE, ET R REPRESENTE UN GROUPE BIPHENYLYLE NON SUBSTITUE. CES COMPOSES SONT UTILISES COMME COLORANTS.THE SUBJECT OF THE PRESENT INVENTION IS MONOAZOIC COMPOUNDS OF FORMULA I: (DRAWING IN BOPI) IN WHICH D REPRESENTS A DIAZOTATION COMPONENT, R REPRESENTS HYDROGEN, CHLORINE OR BROMINE OR AN ALKYL, ALCOXY OR ALCOXYETHOXY GROUP, HYDROGEN, AN ALKYL-CARBONYLAMINO, ALKYL-CARBONYLAMINO, ALCOXYALKYL-CARBONYLAMINO, FLUORO-, CHLORO- OR BROMO-ALKYL-CARBONYLAMINO, HYDROXY-ALKYL-CARBONYLONYLOXY-ALKYL-CARBONYL-CARBONYL-CARBONYL-OUCOYL-CARBONYL-CARBONYL-OUCO-AMINOYL-OUCO-AMINOYL-OUCO-AMINOYL-CARBONYL-OR R REPRESENTS HYDROGEN OR A SUBSTITUTED OR NON-SUBSTITUTED ALKYL GROUP, A REPRESENTS A LINEAR OR BRANCHED ALKYLENE GROUP, AND R REPRESENTS A NON-SUBSTITUTED BIPHENYL GROUP. THESE COMPOUNDS ARE USED AS COLORANTS.
Description
La présente invention a pour objet de nouveaux composés monoazoïques, leurThe subject of the present invention is new monoazo compounds, their
préparation et leur utilisation comme colorants preparation and their use as dyes
de dispersion.dispersion.
La présente invention a plus particulièrement pour objet les composés de formule I R1 The present invention more particularly relates to compounds of formula I R1
D-N=N Q N\ (I)D-N = N Q N \ (I)
A-OR5A-OR 5
22
dans laquelle D représente une composante de diazotation, R1 représente l'hydrogène, le chlore ou le brome ou un groupe alkyle en Cl-C2, alcoxy en Cl-C4 ou (alcoxy en C1-C4)éthoxy, R2 représente l'hydrogène ou un groupe alkyle en C1-C4, (alkyl en wherein D represents a diazotization component, R1 represents hydrogen, chlorine or bromine or a C1-C2 alkyl, C1-C4 alkoxy or (C1-C4 alkoxy) ethoxy group, R2 represents hydrogen or a C 1 -C 4 alkyl group,
C1-C4)-carbonylamino, (alcoxy en C1-C4)-(alkyl en C1-C3)- C1-C4) -carbonylamino, (C1-C4-alkoxy) - (C1-C3) alkyl -
carbonylamino, fluoro-, chloro- ou bromo-(alkyl en C1-C4)-carbonylamino, hydroxy-(alkyl en C1-C3)-carbonylamino, (alcoxy en C1-C4)-carbonylamino, (alcoxy en C1-C4)-(alcoxy en C2-C4)-carbonylamino ou (alkyl en C1-C4)sulfonylamino, R3 représente l'hydrogène ou un groupe alkyle en C1-C4 non substitué ou alkyle en C2-C3 substitué par un groupe OH, alcoxy en carbonylamino, fluoro-, chloro- or bromo-C 1 -C 4 -alkylcarbonylamino, hydroxy-C 1 -C 3 -alkylcarbonylamino, (C 1 -C 4 -alkoxy) -carbonylamino, (C 1 -C 4 -alkoxy) - (C 1 -C 4) alkoxycarbonylamino or (C 1 -C 4) alkylsulfonylamino, R 3 represents hydrogen or unsubstituted C 1 -C 4 alkyl or C 2 -C 3 alkyl substituted by OH, alkoxy
C1-C4, CN, (alkyl en C1-C3)-carbonyloxy, (alcoxy en Cl-C4)- C1-C4, CN, (C1-C3) alkylcarbonyloxy, (C1-C4) alkoxy -
carbonyloxy, (alcoxy en CI-C4)-carbonyle, (alcoxy en Cl-C4)- carbonyloxy, (C1-C4) alkoxycarbonyl, (C1-C4) alkoxy -
éthylcarbonyloxy ou (alcoxy en C1-C4)-éthoxycarbonyloxy, A représente un groupe alkylène en C2-C4 linéaire ou ramifié, et ethylcarbonyloxy or (C1-C4 alkoxy) ethoxycarbonyloxy, A represents a linear or branched C2-C4 alkylene group, and
R5 représente un groupe biphénylyle non substitué. R5 represents an unsubstituted biphenylyl group.
D signifie de préférence D', D' signifiant un radical D preferably means D ', D' meaning a radical
phényle, thiényle, thiazolyle, isothiazolyle, pyrazolyle, imida- phenyl, thienyl, thiazolyl, isothiazolyl, pyrazolyl, imidazole,
zolyle, 1,3,4- ou 1,2,4-thiadiazolyle, benzothiazolyle ou benzoisothiazolyle. D signifie plus préférablement D", D" signifiant un groupe de formule (a) R6 502N< (a) zolyl, 1,3,4- or 1,2,4-thiadiazolyl, benzothiazolyl or benzoisothiazolyl. D is more preferably D ", D" signifying a group of formula (a) R6 502N <(a)
R7 R8R7 R8
dans laquelle -in which -
R6 représente un halogène ou un groupe CN, N02 ou (alkyl en C1-C2) sulfonyle et R7 et R8 représentent l'hydrogène ou un halogène, au moins un des symboles de R7 et R8 devant représenter l'hydrogène; R6 is halogen or CN, NO2 or (C1-C2alkyl) sulphonyl and R7 and R8 are hydrogen or halogen, at least one of R7 and R8 being hydrogen;
ou bien D" représente un groupe 5-nitrothiazolyle-2, 4-méthyl-5- or D "represents a 5-nitrothiazolyl-2,4-methyl-5-
nitrothiazolyle-2, 4-cyanoisothiazolyle-5, 3-méthyl-4-cyano- nitrothiazolyl-2,4-cyanoisothiazolyl-5,3-methyl-4-cyano-
isothiazolyle-5, 1-phényl ou 1-méthyl-4-cyanopyrazolyle-5, isothiazolyl-5, 1-phenyl or 1-methyl-4-cyanopyrazolyl-5,
1-phényl-3-méthyl-4-cyanopyrazolyle-5, 1,3-diméthyl-4-cyano- 1-phenyl-3-methyl-4-cyanopyrazolyl-5,1,3-dimethyl-4-cyano-
pyrazolyle-5, 1-allyl- ou 1-(alkyl en C1-C2)-4,5-dicyanoimidazo- pyrazolyl-5,1-allyl- or 1- (C1-C2alkyl) -4,5-dicyanoimidazo
lyle-2, 5(alkyl en C1-C2)-mercapto-1,3,4-thiadiazolyle-2, 2,5-alkyl-C 1 -C 2 -alkylmercapto-1,3,4-thiadiazolyl-2,
3-phényl-1,2,4-thiadiazolyle-5, 5-nitro-2,1-benzoisothiazol- 3-phenyl-1,2,4-thiadiazolyl-5,5-nitro-2,1-benzoisothiazol
yle-3, 3,5-dinitrothiényle-2, 3,5-dicyano-4-méthyl-thiényle-2 yl-3,3,5-dinitrothienyl-2,3,5-dicyano-4-methyl-thienyl-2
ou 3-cyano-4-méthyl-5-[(alcoxy en C1-C2)-carbonyl]thiényle-2. or 3-cyano-4-methyl-5 - [(C 1 -C 2 alkoxy) carbonyl] thienyl-2.
Rl signifie de préférence R'1, R'i signifiant R1 preferably means R'1, R'i meaning
l'hydrogène ou un groupe méthoxy ou éthoxy. R1 signifie plus préfé- hydrogen or a methoxy or ethoxy group. R1 means more preferred
rablement l'hydrogène.hydrogen.
R2 signifie de préférence R'2, R'2 signifiant l'hydro- R2 preferably means R'2, R'2 meaning hydro-
gène ou un groupe méthyle ou (alkyl en C1-C2)-carbonylamino, plus gene or a methyl group or (C1-C2 alkyl) -carbonylamino, plus
préférablement R"2, R"2 signifiant l'hydrogène ou un groupe méthyle. preferably R "2, R" 2 signifying hydrogen or a methyl group.
R3 signifie de préférence R'3, R'3 signifiant un groupe alkyle en C1-C4, plus préférablement R"3, R"3 signifiant un groupe R3 is preferably R'3, R'3 is C1-C4 alkyl, more preferably R "3, R" 3 is a group
méthyle ou éthyle.methyl or ethyl.
A signifie de préférence A', A' signifiant un groupe -CH2-CH2-, -CH2-CHCH3 ou -CH2CH-C2H5s plus préférablement A A is preferably A ', A' being -CH2-CH2-, -CH2-CHCH3 or -CH2CH-C2H5s, more preferably A
signifie un groupe -CH2CH2-.means a group -CH2CH2-.
R5 signifie de préférence R'5, R'5 signifiant un reste R5 preferably means R'5, R'5 meaning a remainder
ortho- ou para-biphénylyle non substitué. unsubstituted ortho- or para-biphenylyl.
R6 signifie de préférence R'6, R'6 signifiant le chlore, le brome, l'iode ou un groupe cyano; R6 signifie plus préférablement R6 preferably means R'6, where R'6 is chlorine, bromine, iodine or a cyano group; R6 more preferably means
le chlore.chlorine.
R7 signifie de préférence R'7, R'7 signifiant l'hydrogène, le chlore ou le brome et R8 signifie de préférence l'hydrogène. Plus préférablement, R7 et R8 signifient tous les deux l'hydrogène. Dans cette demande, sauf indication contraire, tout groupe alkyle en C1-C4 signifie de préférence un groupe méthyle ou éthyle, et tout groupe alcoxy en C1-C4 signifie de préférence un groupe méthoxy ou éthoxy. Par halogène, on entend le fluor, le chlore, le brome et l'iode, plus préférablement ces trois derniers R7 preferably means R'7, where R'7 is hydrogen, chlorine or bromine and R8 is preferably hydrogen. More preferably, R7 and R8 both mean hydrogen. In this application, unless otherwise indicated, any C 1 -C 4 alkyl group preferably means a methyl or ethyl group, and any C 1 -C 4 alkoxy group preferably means a methoxy or ethoxy group. Halogen means fluorine, chlorine, bromine and iodine, more preferably the last three
lorsque R6 signifie un halogène.when R6 is a halogen.
Les composés préférés de formule I sont ceux de formule II R' Rj 6 R i -3 NO2 i N=N Q(l < f A'-OR5 7 2 The preferred compounds of formula I are those of formula II ## STR1 ##
dans laquelle les symboles sont tels que définis plus haut. wherein the symbols are as defined above.
Conformément au procédé de l'invention, pour préparer les composés de formule I on copule le diazoïque d'une amine de formule III According to the process of the invention, to prepare the compounds of formula I, the diazo compound of an amine of formula III is
D-NH2 (III)D-NH2 (III)
dans laquelle D a la signification déjà donnée, avec une composante de copulation de formule IV in which D has the meaning already given, with a coupling component of formula IV
\A-OR5\ A-OR 5
R2 dans laquelle R1, R2, R3, R5 et A ont les significations déjà données. La diazotation et la copulation sont effectuées selon les R2 in which R1, R2, R3, R5 and A have the meanings already given. Diazotation and copulation are performed according to
méthodes connues.known methods.
Les composés de formule III et IV sont connus ou peuvent être préparés selon les méthodes connues à partir de composés connus. L'invention concerne également l'utilisation des composés monoazoïques de formule I comme colorants. Pour leur utilisation comme colorants, les composés de The compounds of formula III and IV are known or can be prepared according to known methods from known compounds. The invention also relates to the use of monoazo compounds of formula I as dyes. For their use as dyes, the compounds of
formule I peuvent être mis sous forme de préparations tinctoriales. Formula I can be formulated as dyeing preparations.
De telles préparations tinctoriales peuvent être obtenues selon des méthodes connues, par exemple par broyage en présence d'un agent de dispersion ou de charge, suivi éventuellement d'un séchage sous pression réduite ou par atomisation. Avec ces préparations on peut, après addition d'une quantité plus ou moins importante d'eau, Such dyeing preparations may be obtained according to known methods, for example by grinding in the presence of a dispersing agent or filler, optionally followed by drying under reduced pressure or by spraying. With these preparations one can, after addition of a more or less important quantity of water,
teindre en bain long ou court, foularder ou imprimer. dye in long or short bath, pad or print.
Les colorants de l'invention montent bien en suspension aqueuse sur les substrats textiles constitués de matières organiques The dyes of the invention mount well in aqueous suspension on textile substrates made of organic materials
hydrophobes à poids moléculaire élevé, synthétiques ou semi- high molecular weight, synthetic or semi-hydrophobic
synthétiques. Les colorants de l'invention sont particulièrement appropriés pour la teinture, le foulardage ou l'impression de matières textiles constituées de polyesters aromatiques linéaires, d'hémipentaacétate de cellulose, de triacétate de cellulose et de polyamides synthétiques. Les colorants de l'invention se signalent synthetic. The dyes of the invention are particularly suitable for the dyeing, padding or printing of textile materials consisting of linear aromatic polyesters, cellulose hemipentaacetate, cellulose triacetate and synthetic polyamides. The dyes of the invention are indicated
par une faible tendance à la thermomigration. by a slight tendency to thermomigration.
La teinture, le foulardage ou l'impression peuvent être effectués selon des méthodes connues, en particulier comme décrit Dyeing, padding or printing can be carried out according to known methods, in particular as described
dans le brevet français n 1 445 371. in French Patent No. 1,445,371.
Les exemples suivants illustrent la présente invention sans aucunement en limiter la portée. Dans ces exemples, toutes les parties et pourcentages s'entendent en poids et les températures The following examples illustrate the present invention without in any way limiting its scope. In these examples, all parts and percentages are by weight and temperatures
sont indiquées en degrés Celsius, sauf indication contraire. are in degrees Celsius unless otherwise indicated.
EXEMPLE 1EXAMPLE 1
On agite pendant 12 heures 17,3 parties de 2-chloro-4- 17.3 parts of 2-chloro-4- are stirred for 12 hours.
nitroaniline dans 44 parties d'acide chlorhydrique concentré et on ajoute 125 parties d'eau et ensuite 45 parties de glace. On fait réagir ce mélange pendant 40 minutes à une température comprise entre O et 2 avec 7,0 parties de nitrite de sodium dissous dans parties d'eau. Tout en refroidissant à une température comprise entre O et 50, on agite le mélange pendant encore 2 heures, on détruit l'excès d'acide nitreux avec de l'acide amidosulfonique et on filtre le produit pour éliminer les traces d'impuretés solides nitroaniline in 44 parts of concentrated hydrochloric acid and 125 parts of water and then 45 parts of ice are added. This mixture is reacted for 40 minutes at a temperature between 0 and 2 with 7.0 parts of sodium nitrite dissolved in parts of water. While cooling to a temperature between 0 and 50, the mixture is stirred for a further 2 hours, the excess nitrous acid is destroyed with amidosulfonic acid and the product is filtered to remove traces of solid impurities.
qui sont présentes.who are present.
Tout en agitant et en refroidissant par de la glace à une température comprise entre O et 50, on ajoute très lentement en minutes la solution résultante de sel de diazonium à une solution de 33,2 parties de N-éthylN-(2'-o-biphénylyloxyéthyl)-aniline dans While stirring and cooling with ice at a temperature between 0 and 50, the resulting solution of diazonium salt is added very slowly in minutes to a solution of 33.2 parts of N-ethyl- (2'-o). -biphenylyloxyethyl) -aniline in
400 parties d'acide acétique glacial et 140 parties d'eau glacée. 400 parts of glacial acetic acid and 140 parts of ice water.
Lorsque la copulation est terminée, on agite le mélange pendant encore 2 heures sans refroidissement et on le filtre. On lave le résidu jusqu'à ce qu'il soit exempt d'acide et de sel et on le sèche When the coupling is complete, the mixture is stirred for a further 2 hours without cooling and filtered. The residue is washed until it is free of acid and salt and dried
à 50 sous vide.at 50 under vacuum.
On obtient ainsi le composé de formule la Cl (la) The compound of formula la Cl (la) is thus obtained
0 NO=4 -N//C2H5 X 6H50 NO = 4 -N // C2H5 X 6H5
EXEMPLE 2EXAMPLE 2
En procédant comme décrit à l'exemple 1 et en utilisant, à la place de la N-éthyl-N-(2'-o-biphénylyloxyéthyl)-aniline, une By proceeding as described in Example 1 and using, in place of N-ethyl-N- (2'-o-biphenylyloxyethyl) -aniline, a
quantité correspondante de N-éthyl-N-(2'-p-biphénylyloxyéthyl)- corresponding amount of N-ethyl-N- (2'-p-biphenylyloxyethyl)
aniline, on obtient le composé de formule 2a Cl aniline, the compound of formula 2aCl is obtained
/,.C2H5/,.C2H5
N024N=N1\(CH2)î2 _ C 6 5N024N = N1 \ (CH2) 2 C6 5
Sous forme ultradispersée, il teint les tissus en polyesters en nuances rouge-bleu. Les teintures résultantes présentent de bonnes solidités. In ultradispersed form, it dyes polyester fabrics in red-blue shades. The resulting dyes have good fastness.
EXEMPLES 3 à 30EXAMPLES 3 to 30
En procédant de manière analogue à celle décrite a l'exemple 1 et en utilisant les produits de départ appropriés, ce peut préparer les composés monoazoiques du tableau 1 suivant qui répondent à la formule By proceeding in a manner analogous to that described in Example 1 and using the appropriate starting materials, it can prepare the following monoazo compounds of Table 1 which correspond to the formula
6 R36 R3
NO2 QNO2 Q
N 2 f t A-0-R5 -N 2 f t A-0-R5 -
dans laquelle les symboles ont les significations données dmsile in which the symbols have the given meanings
tableau.board.
TABLEAU 1TABLE 1
Ex. R6 R7 R2 R3 A R5 u e Nos. sur le polyeste rouge 3 -Cl H H -CH3 CH2CH2 o-biphénylyle bleuatre Ex. R6 R7 R2 R3 A R5 u e Nos. on the red polyeste 3 -Cl H H -CH3 CH2CH2 O-biphenylyl bluish
4 do. H H -C3H7 do. do. do.4 do. H H -C3H7 do. do. do.
do. H H -C4H do. do. do.do. H H -C4H do. do. do.
6 do. H H do. do. -p-biphénylyle do. 6 do. H H do. do. -p-biphenylyl do.
7 do. H H -C3H7 do. do. do.7 do. H H -C3H7 do. do. do.
8 do. H H -CH3 do. do. do.8 do. H H -CH3 do. do. do.
/CH3/ CH3
9 do. H H -C2H5 -CH2CH- do. do.9 do. H H -C 2 H 5 -CH 2 CH-. do.
do. H H do. -CH2CH-do. H H do. -CH2CH-
12H5 do. do.12H5 do. do.
11 do. H CH3 do. do. H rubis11 do. H CH3 do. do. H ruby
12 do. H do. ddo. o. -0-biphénylyle do. 12 do. H do. ddo. o. -0-biphenylyl do.
13 do. H H do. -CH2CH2- do. rouge bleuâtre 13 do. H H do. -CH2CH2- do. bluish red
14 do. H H do. CH2CH- do. do.14 do. H H do. CH2CH-do. do.
C2H5C2H5
-B H H do. -CH2CH2- do. do.-B H H do. -CH2CH2- do. do.
16 -I H H do. do. do. do.16 -I H H do. do. do. do.
17 Cl Cl H do. do. do. do.17 Cl Cl H do. do. do. do.
18 do do. H do. do. P-biphenylyle do. 18 do do. H do. do. P-biphenylyle do.
19 -Br H H do. do. do. do.19 -Br H H do. do. do. do.
-CN. H -CH2CH2CN do. do. do.-CN. H -CH2CH2CN do. do. do.
21 do H H,do. -do. o-biphénylyle do. 21 do H H, do. -do. o-biphenylyl do.
22 do H H do. -CHCH- do. d o.22 do H H do. -CHCH-do. d o.
CH3CH3
23 Cl H -CH -CH2CH2COOCH3 -CH2CH2- do. do. HClCH 2 CH 2 CH 2 COOCH 3 -CH 2 CH 2 -d. do.
24 Cl H do. -CH2CH20COCH3 do. do. do. 24 Cl H do. -CH2CH20COCH3 do. do. do.
Cl H do. -CH2CH2OCOOCHI do. do. do.Cl H do. -CH2CH2OCOOCHI do. do. do.
TABLEAU I (suite) Ex. R6 R7 R2 R3 A R5 uance Nos. R5 sur le 5..... ___, _ lyester 26 H H -NHCOCH3 CH2CH2CN -CH2CH2- biphényl- rouge TABLE I (continued) Ex. R6 R7 R2 R3 A R5 uance Nos. R5 on 5 ..... ___, _ lyester 26 H H -NHCOCH3 CH2CH2CN -CH2CH2- biphenyl- red
27 Cl H do. do. do. do. do.27 Cl H do. do. do. do. do.
28 -CN H H -C2H5 do. do. rouge28 -CN H H -C2H5 do. do. red
leuâtre-leuâtre-
29 do. H H do. -CH2CH-29 do. H H do. -CH2CH-
CH3 do. do.CH3 do. do.
do. H H do. do.:p-biphényl- do.do. H H do. do.:p-biphenyl- do.
_le_the
EXEMPLES 31-40EXAMPLES 31-40
On peut préparer les composés de formule Compounds of formula
R6 R1R6 R1
NO2 N = N N 3NO2 N = N N 3
NA- O--R5NA- O - R5
R2 dans laquelle les symboles sont tels que définis dans le tableau 2 en procédant de manière analogue à celle de l'exemple 1 à partir des R2 in which the symbols are as defined in Table 2 by proceeding in a manner analogous to that of Example 1 from the
produits de départ appropriés.appropriate starting materials.
TABLEAU 2TABLE 2
Ex. R R 2 R23 A R5 R6 R8 Nuance sur le Nos. 2 3 5 R8 polyester 31 Cl NHCOCH3 H -CH2CH2- -o-biph6nylyle Cl H rouge 32 H H -C2H5 do. do. Cl Cl brun rougeatre Ex. R 2 R23 A R5 R6 R8 Grade on Nos. R8 polyester 31 Cl NHCOCH3H -CH2CH2- -o-biphenyl Cl H red 32H H -C2H5 do. do. Cl Cl reddish brown
33 H H do. -CH2CH do. Cl Cl do.33 H H do. -CH2CH do. Cl Cl do.
CH3CH3
34 H H do. -CH2CH2- p-biphénylyle Cl Cl do. 34 H H do. -CH 2 CH 2 -p-biphenylyl Cl Cl do.
H H do. do. o-biphenylyle Br Cl do.H H do. do. o-biphenylyl Br Cl do.
36 -OCH3 -NHCOCH3 H do. do. -NO2 Br bleu marine 36 -OCH3 -NHCOCH3H do. do. -NO2 Br navy blue
37 -OC2H5 do. H do. do. do. Cl do.37-OC2H5 do. H do. do. do. Cl do.
38 -OCH2CH2OCH3 -NHCOCH3 H do. do. do. Br do. 38 -OCH2CH2OCH3 -NHCOCH3 H do. do. do. Br do.
39 -OCH3 -NHCOCH3 H -CH2CH- do. do. Cl do. 39 -OCH3 -NHCOCH3H-CH2CH- do. do. Cl do.
CH3CH3
do. -CH3 -CH3 -CH2CH2CH2- do. do. C1 do. do. -CH3 -CH3 -CH2CH2CH2-do. do. C1 do.
Ln -Pl. -1l U'JLn-Pl. -1l U'J
EXEMPLES 41-68EXAMPLES 41-68
On peut préparer les composés de formule Compounds of formula
RN RRN R
D-N N N ?4'D-N N N? 4 '
A- O- R5A- O- R5
dans laquelle les symboles sont tels que définis dans le tableau 3 en procédant de manière analogue à celle décrite à l'exemple 1 à wherein the symbols are as defined in Table 3 by proceeding analogously to that described in Example 1 at
partir des produits de départ appropriés. from the appropriate starting materials.
TABLEAU 3TABLE 3
Ex. R1 R R A R D Nuance sur Nos. 1 2 3 5 polyester 41 H H C2H5 -CH2CH2- o-biphénylyle 3-méthyl-4-cyano-isothiazolyb-5 ruge bleuâtre Ex. R1 R R A R D Nuance on Nos. 1 2 3 5 polyester 41 H H C2H5 -CH2CH2-o-biphenylyl 3-methyl-4-cyanoisothiazolyb-5 bluish ruler
42 H H do. do. -p-biphénylyle do. do. 42 H H do. do. -p-biphenylyl do. do.
43 H H -CH2CH2CN do. -o-biphénylyle do. do. 43H H -CH2CH2CN do. o-biphenylyl do. do.
44 H H do. do. do. 4-cyano-l,2 -isothiazolyle-5 do. 44 H H do. do. do. 4-cyano-1,2 -isothiazolyl-5d.
H H -C2H5 -CH2CH- do. do. do.H H -C 2 H 5 -CH 2 CH-. do. do.
CH3 46 H H do. do. do. 4-chloro-5-formylthiazolyb-2 violet CH3 46 H H do. do. do. 4-chloro-5-formylthiazolb-2 violet
47 H H do. -CH2CH2 do. do. do.47 H H do. -CH2CH2 do. do. do.
48 H H do. do. do. 5-nitrothiazolyle-2 violetbleuâtre 49 H -CH3 do. do. do. do. leu mugeatre 48 H H do. do. do. 5-nitrothiazolyl-2 violetbleuâtre 49 H -CH3 do. do. do. do. their mug
H do. do. -CH2CH2CH2- do. do. do.H do. do. -CH2CH2CH2- do. do. do.
51 -OCH3 do. -C3H7 -CH2CH2- do. do. bleu 52 H H -C2H5 -CH2CH- do. do. iolet bleuAti CH3 53 H -CH3 do. do. do. do. bleu rgeâtre 3... bleu rmge&tre 51 -OCH3 do. -C3H7 -CH2CH2- do. do. blue 52H H -C2H5 -CH2CH- do. do. iolet blueAti CH3 53 H -CH3 do. do. do. do. blue raspberry 3 ... blue rmge & tre
54 H do. do. -CH2CH2- -p-biphénylyle do. do. 54 H do. do. -CH2CH2- -p-biphenylyl do. do.
H do. do. -CH2C- do. do. do.H do. do. -CH2C-do. do. do.
CH3 TABLEAU 3 (suite) Ex. R1 R2 R3 A R5 D Nuance sur le Nos. 1 23_polyester _.i i._ , ., 56 H H -C2H5 -CH2CH2 -p-biphénylyle 3,5dinitrothienyle-2 bleu CH3 TABLE 3 (continued) Ex. R1 R2 R3 A R5 D Grade on Nos. 1 23_polyester _.i i._, 56 H H -C 2 H 5 -CH 2 CH 2 -p-biphenylyl 3,5-dinitrothienyl blue
57 H H do. do. -o-biphénylyle do. do. 57 H H do. do. o-biphenylyl do. do.
58 H H do. -CH2 H do. do. do.58 H H do. -CH2 H do. do. do.
CH3 59 H -CH3 do. -CH2CH2 do. 3,5-dicyano-4-mâthylthiényle-2 bleu ougeatrei H H do. do. do. 3-cyano-4-méthyl-5-méthoxy- rouge bleuâtre carbonylthiényb-2 61 H H do. do. do. 1-éthyl-4,5-dicyanoimidazolyle-2 rouge 62 H -CH3 do. do. do. do. rouge bleuâtre 63 H H do. do. do. 5-nitro(2,1)-benzoisothiazolyle-3 bleu mugeatre 64 H -CH3 do. do. do. do. bleu CH3 59H-CH3 do. -CH2CH2 do. 3,5-dicyano-4-methylthienyl-2 blue ugeatrei H H do. do. do. 3-cyano-4-methyl-5-methoxy-bluish red carbonylthienyl-2 61H H do. do. do. 1-ethyl-4,5-dicyanoimidazolyl-2 red 62H-CH3 do. do. do. do. bluish red 63 H H do. do. do. 5-nitro (2,1) -benzoisothiazolyl-3 melt blue 64 H-CH3 do. do. do. do. blue
H H do. -CH2CH do. do. do.H H do. -CH2CH do. do. do.
H3 66 H H do. -CH2CH2- do. 3-méthoxycarbonyléthyl-mercapto- rouge bleuâtre 1,2,4-thiadiazolyb-5 H3 66 H H do. -CH2CH2- do. 3-methoxycarbonylethyl-mercapto bluish red 1,2,4-thiadiazolyb-5
67 H -CH3 -CH2CH2CN do. do. do. do.67H -CH3 -CH2CH2CN do. do. do. do.
68 H do. do. do. do. 2-méthylmercapto-1,3,4-thiadia- rouge zolyle-5 I w Exemple d'application On broye dans un moulin à billes le composé de formule la (exemple 1) en présence d'un agent de dispersion (par exemple un lignine sulfonate disponible dans le commnerce) et on l'atomise ensuite en une préparation tinctoriale ultradispersée ayant une dimension moyenne de particules de 1 M et un rapport de coupage de 68 H do. do. do. do. 2-methylmercapto-1,3,4-thiadia-red zolyl-5 I Example of application The compound of formula la (Example 1) is ground in a ball mill in the presence of a dispersing agent (for example a commercially available lignin sulphonate) and is then atomized into an ultradispersed dye preparation having a mean particle size of 1M and a cutting ratio of
3,5: 10.3.5: 10.
On disperse 16 parties de cette préparation dans 1000 parties d'eau et on ajoute cette dispersion à 60 au bain en circulation (13 000 parties contenant 30 parties de sulfate d'ammonium et 0,3 partie d'acide formique en tant que tampon). On introduit ensuite une bobine croisée nettoyée au préalable et pressée (1000 parties de fibres de polyester sur canette en matière plastique), on ferme l'autoclave de teinture et on chauffe à 130 en l'espace de 35 minutes. Au bout de 60 minutes on refroidit h 80 , on vidange le bain de teinture et on lave le substrat teint à l'eau froide. On soumet le substrat teint à un traitement réducteur de 16 parts of this preparation are dispersed in 1000 parts of water and this dispersion is added to the bath in circulation (13000 parts containing 30 parts of ammonium sulphate and 0.3 parts of formic acid as buffer) . Then a pre-cleaned and pressed cross-coil (1000 parts polyester fiber on a plastic bobbin) is introduced, the dyeing autoclave is closed and heated to 130 in 35 minutes. After 60 minutes, the mixture is cooled to 80 ° C., the dye bath is drained and the dyed substrate is washed with cold water. The dyed substrate is subjected to a reducing treatment of
dépouillement, on essore ensuite la bobine croisée et on la sèche. stripping, we then wring the cross coil and dry it.
On obtient une teinture rouge bleuâtre unie et intense, ayant d'excellentes solidités au mouillé, h la thermofixation et au frottement et une faible tendance h la thermomigration. Les bobines A strong, bluish red dye is obtained, having excellent wet fastness, heat setting and rubbing and a low tendency to thermomigration. The reels
sont exemptes de particules de colorant sur les fibres. are free of dye particles on the fibers.
A la place du colorant de l'exemple 1 on peut utiliser une quantité appropriée de l'un quelconque des colorants des Instead of the dye of Example 1, an appropriate amount of any of the dyestuffs of the present invention can be used.
exemples 2 h 68.examples 2 hrs 68.
Claims (10)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3339944 | 1983-11-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2554455A1 true FR2554455A1 (en) | 1985-05-10 |
FR2554455B1 FR2554455B1 (en) | 1987-12-24 |
Family
ID=6213485
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR8416626A Expired FR2554455B1 (en) | 1983-11-04 | 1984-10-29 | NOVEL MONOAZOIC COMPOUNDS, THEIR PREPARATION AND THEIR USE AS DYES |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPS60112857A (en) |
CH (1) | CH660746A5 (en) |
FR (1) | FR2554455B1 (en) |
GB (1) | GB2148924B (en) |
IT (1) | IT1199215B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4910299A (en) * | 1986-12-09 | 1990-03-20 | Ciba-Geigy Corporation | Disperse azo dyes containing N-phenoxyalkyleneanilines as coupling components |
KR970009393B1 (en) * | 1988-10-11 | 1997-06-12 | 스미또모 가가꾸 고교 가부시끼가이샤 | Monoazo disperse dye compounds, their production and their use |
DE3901724A1 (en) * | 1989-01-21 | 1990-07-26 | Bayer Ag | METHOD FOR COLORING SYNTHETIC FIBER MATERIALS |
DE102007037522A1 (en) * | 2007-08-09 | 2009-02-12 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Disperse dyes, their preparation and use |
CN106118118B (en) * | 2016-06-16 | 2017-04-19 | 蓬莱嘉信染料化工股份有限公司 | Blue disperse dye, and composition, preparation method and application thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2217385A1 (en) * | 1972-07-31 | 1974-09-06 | Sandoz Sa | |
GB1395022A (en) * | 1972-01-31 | 1975-05-21 | Ici Ltd | Water-insoluble monoazo dyestuffs |
DE2916137A1 (en) * | 1979-04-20 | 1980-10-30 | Bayer Ag | Di:cyano-phenyl-azo aniline dyestuff use on cellulose - and mixed fibres swollen with water miscible swelling agent |
-
1984
- 1984-10-26 CH CH5122/84A patent/CH660746A5/en not_active IP Right Cessation
- 1984-10-29 FR FR8416626A patent/FR2554455B1/en not_active Expired
- 1984-10-31 IT IT49093/84A patent/IT1199215B/en active
- 1984-11-01 GB GB08427620A patent/GB2148924B/en not_active Expired
- 1984-11-02 JP JP59230459A patent/JPS60112857A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1395022A (en) * | 1972-01-31 | 1975-05-21 | Ici Ltd | Water-insoluble monoazo dyestuffs |
FR2217385A1 (en) * | 1972-07-31 | 1974-09-06 | Sandoz Sa | |
DE2916137A1 (en) * | 1979-04-20 | 1980-10-30 | Bayer Ag | Di:cyano-phenyl-azo aniline dyestuff use on cellulose - and mixed fibres swollen with water miscible swelling agent |
Also Published As
Publication number | Publication date |
---|---|
CH660746A5 (en) | 1987-06-15 |
JPS60112857A (en) | 1985-06-19 |
GB2148924A (en) | 1985-06-05 |
IT1199215B (en) | 1988-12-30 |
IT8449093A1 (en) | 1986-05-01 |
GB8427620D0 (en) | 1984-12-05 |
IT8449093A0 (en) | 1984-10-31 |
GB2148924B (en) | 1988-01-13 |
FR2554455B1 (en) | 1987-12-24 |
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