FR2641541A1 - COLORANTS AND MIXTURES OF DIAZOIC DISPERSED DYES, THEIR PREPARATION AND THEIR APPLICATION TO THE DYEING OR PRINTING OF A HYDROPHOBIC FIBROUS MATERIAL - Google Patents

Abstract

The invention describes the preparation and use of disperse dyes, of formula I: (CF DRAWING IN BOPI) (wherein R1, R'1 and R2 are each, independently, H, CN, Br, an alkyl or alkoxy group C1 or C2, and R3 and R4 are each independently C2 or C3 alkylene) and mixtures thereof with up to 80% by weight of other yellow disperse dyes. Application: dyeing, dyeing by padding or printing hydrophobic fibers (polyester).

Description

E641541

  The present invention relates to dyes

  sands dispersions (disperse dyes) disazo

  pyridone, and mixtures thereof, and their prominent suitability as disperse dyes for dyeing, dyeing by padding, or printing a hydrophobic fibrous material. According to the present invention, this provides a disperse dye of formula I

R I

1 - N9N-N

R '5 R

R R 2 3-O-R 4-O

  (wherein R 1 R 'and R 2, independently of each other, are selected from hydrogen, chlorine or bromine, C 1 or C 2 alkyl or C 1 or C 2 alkoxy, and

  R3 and R4, independently of one another, represent

  each is a C2 or C3 alkylene group),

and their mixtures.

  In addition, according to the invention, this provides a mixture comprising from 10 to 90% by weight of one or more dyes of formula I, and from 90 to 10% by weight of one or more other yellow disperse dyes, on the basis of

  weight of the dyes present in the composition.

  Preferably, R 1 represents a hydrogen atom or

  chlorine, R'1 represents a hydrogen atom and R2 represents

  is hydrogen, chlorine, methyl or methoxy; and, even better, the symbols Ri, R'1 and R2

  each represent a hydrogen atom.

  Preferably, R3 and R4 each represent a group

pe of formula -CH2-CH2-.

  Preferably, in a mixture as defined above

  above, the proportion of the compound of formula I is 50 to% by weight and the proportion of one or more other yellow disperse dyes is 10 to 50% by weight. Other preferred dispersed yellow dyes are chosen from disperse dyes corresponding to formulas II to XII: 74t CH3 NI

3 C3 O

N N I 0

R OH R8

R6 8

  (wherein R5 is, as shown, in position 3 or

  in position 4, and is selected from a hydrogen atom

  gene or chlorine or bromine and a (C1-C8) alkoxycarbonyl group, a (C1-C3) alkoxy (C2-C3) alkoxycarbonyl group, a C2-C3 alkenyloxy (C2-alkoxy) group or C3) carbonyl, (C1-C3) alkoxy (C2-C3) alkoxy (C2-C3) alkoxycarbonyl, phenoxy (C2-C3) alkoxycarbonyl, phenylalkoxy (C1-C3) ) carbonyl, benzylcarbonyloxy, alkyl- (C1-C8) aminocarbonyl, (C1-C8) alkylaminosulfonyl,

  alkyl (C1 to C3) benzoyl, phenylsulfonyloxy, benzyloxy-

  carbonyl, tetrahydrofuryl (C1-C3) alkoxycarbonyl, cyano, trifluoromethyl or (C1-C7) alkoxy, R represents a hydrogen atom or a nitro, (C1-C8) alkoxycarbonyl or chloro group, R7 represents an atom of hydrogen or chlorine, and R8 is hydrogen, (C1-C4) alkyl, (C1-C4) alkoxy (C1-C4) alkyl or (C1-C4) alkoxycarbonyl (C1-C4) alkyl or ), 4 (C1 to C4) carbonyl (C 1 or C 2) alkyl,

CN CH

IHC6 -N - N - N

III

OH R9

  [wherein R9 is (C1-C8) alkyl, (C1-C4) alkoxy-(C2-C3) alkyl, (C1-C4) alkylcarbonyloxy (C2-C3) alkyl, (C2-alkenyloxy) or C3) (C2-C3) alkoxy (C2-C3) alkyl, (C1-C4) alkylcarbonyloxy (C2-C3) alkoxyalkyl (C2-C3), (C1-C2) alkoxy carbonyloxy (C 2 or C 3) alkyl or a group of formula -CH 2 CH 2 -O-CH 2 CH 2 OH]; OCH

02N- - N N N- N OH IV;

  H C-OCO-X-N-N-. N (CE2CH2COOCH3) 2 V;

3 2 2 3 2 V;

NH COCH3

R 1.1N N N / θHCH2C2Ri2

01N T {N - N N N- 2

CH2CH2CN VI

  R (wherein the two symbols R11 represent a chlorine or bromine atom, and R12 represents a hydrogen atom or an acetoxy group) HHC6-N-N N = N1-rCONU2 VII; 6N-COOq (VII; C6H5 OH

H C - N = N

VIII;

CH3 Br

O IX;

2OP

 2 N-NN / 2 CN X;

0, 2 2

CH CH OCOCH oC H

2 2 26 5

This

02N S N = N XI;

N and H, O2 H3CSO2 N = CH3 H-

XII.

C6H5

  The additional yellow dyes that we prefer

  Especially those that correspond to formulas II and III.

  The dyes of formula I can be prepared from known compounds by known methods, such as

example:

  by coupling, after diazotization, one mole of an aminoazobenzene of formula XIII R1

(N - N 9 - 2

  R2 XIII with one mole of a compound of formula XIV

CN CH

gR 3 -O-R-OOH XIV;

  compounds in which the symbols have the meaning defined

above. -

  Mixtures according to the invention can be prepared from known compounds by known methods, by

example:

a) mixture of colorants com

  before or after formulation in the form of prepara-

  dyes; or b) copulation, on the component, diazotized, of formula

  XIII of the coupler of formula XIV with an additional coupler

  or copulation of two different diazotized components with a coupler; or when it is desired to prepare a mixture of a dye of formula I with the analogous dye of formula III in

  which R9 represents a C1-C4 alkyl (C1-C4) alkyl group

  nyloxy (C2-C3) alkoxy (C2-C3) alkyl, followed by acylation of a portion of the disperse dye of formula I.

  Diazotisation, copulation and acylation are performed.

  lation by generally known methods. The compounds corresponding to formulas XIII and XIV are known, or they can be obtained by operating in a manner analogous to

  known processes for the preparation of similar compounds.

  The treatment of novel compounds of formula I and disperse dye mixtures containing them to obtain dyeing preparations is known, and for example grinding is carried out in the presence of dispersing agents and / or filler. After addition of a controlled amount of water, dyeing, pad-dyeing or printing can be carried out in a long or short bath, using the preparations which are optionally dried under vacuum or by spray drying. From an aqueous suspension, the dyes and dye mixtures are absorbed in an excellent manner on the textile material consisting of a fully synthetic or semi-synthetic organic material,

  hydrophobic, high molecular weight. The dyes con-

  are particularly suitable for dyeing or printing textile material consisting of linear aromatic polyesters, as well as 2 1/2 cellulose acetate and

cellulose triacetate.

  The dyeing or printing is carried out according to known methods, for example those described in the patent

GB-A-1 114 433.

  The dyes obtained have a good to very good overall strength, in particular from the solidity to the

  light, heat setting, sublimation and pleating

  wise; a good capacity of accumulation, a fast speed of absorption or fixation from the bath and a

good bath exhaustion.

  In the following examples, the parties and

  percentages are by weight unless otherwise indicated; temperatures are given in degrees Celsius. When

  parts are given in volume, one part in volume cor-

  corresponds to the volume of one part by weight of water.

Example 1

  Preparation of the compound of formula I '

CH3 CN

RSC, - N - N - O - N - N OH 2 OCI

2'H2CH2O2COH2OH

  32 parts of 4-aminobenzene are stirred overnight in 150 parts of 15% hydrochloric acid and then mixed with 350 parts of ice water. The mixture is then partitioned between 5 and 10, which partially crystallizes, over a period of about 30 minutes, with 34 parts by volume of an aqueous 5N sodium nitrite solution, so that the crystalline solid passes into solution. After 2 hours, the slight excess is decomposed with amidosulphonic acid.

  nitrous acid, and the solution is filtered to

  Diazonium salt is dark brown-red in color.

  77.8 parts of an aqueous solution (at

  49.5%) of 38.5 parts of 3-cyano-6-hydroxy-1-p'-hydroxy-

  P-ethoxyethyl-4-methylpyridone-2 (as ethanol salt)

  nolamine) with 600 parts of iced water and mixing, while maintaining the mixture below 10, in about 1 hour with the solution of diazonium salt

  obtained above. The pH is maintained between 3 and 6

  so much sodium acetate. Stirring is continued for several hours without cooling, the insoluble colorant is filtered off and washed with water until no salt.) The resulting dye is 461 nm (in DMF + 1% acid). ozstallizable acetic acid). The melting point of the dye, after recrystallization from "Cellosolve",

is 200.

Example 2

  Preparation of a dye mixture comprising% of the dye of Example 1 and 40% of a dye

  formula III in which R represents a p'-acetoxy group

  ethoxy-p-ethyl. A mixture of 50 parts of acetic acid and 10 parts of acetic anhydride is heated with stirring for 3 hours at 110 to 10 parts of the dye of formula I ', prepared according to example 1, so that

  the crystalline mass goes into solution. After his cooling

  the acetyl dye precipitates and is separated by

  filtration, it is washed first with acetic acid

  than diluted then with water, and dried under vacuum.

  max of the resulting dye is 462 nm. Point of

melting is 145-147 '.

Example 3

  A mixture of 50% of the dye of the example is prepared.

  1 and 50% of the dye of formula III, in which R 9 represents an ethoxy-n-propyl group, by coupling, by analogy with Example 1, 38.9 parts of an aqueous solution (at 49.5.degree. %), containing 19.25 parts of the coupler of Example 1 and 81.0 parts of an aqueous solution (at

  23.6%) containing 19.1 parts of ethoxy-n-propyl-3-

  cyano-6-hydroxy-4-methylpyridone-2, with the diazonium salt

  prepared by analogy with Example 1.

  Examples 4 to 49 Other dispersed dye mixtures according to the invention can be prepared by operating in a manner analogous to

  what is described in the examples above, and these colors

  are shown in the following tables.

Table 1

  Mixtures of disperse dyes of formula I 'with disperse dyes of formula II, wherein R7 represents a hydrogen atom, are given in the following Table I. Ex.% Disperse dye n of formula R5 R6 R8

I '. II

4 80 20 4 -H5C6CH2COCO H -C4H9

  50 50 ditto H idem 6 80 20 4-C4Hg-CH (C2Hs) CH2NHSo2Hdem

7 75 25 3-H5C6-S02-0- H -CH3

  8 80 [10 Cl 2-N02 -C3H7 idem do -C4Hg 9 85 15 idem 3-CL -CH3

  75 25 3 -H5C6-CH2-CO-O-H -CH2CH2CH2OCH3

  It is suitable for use in the preparation of the formula ## STR2 ## wherein: ## STR1 ## wherein: ## STR2 ##

  65 4-CH2 = CH-CH2O (CH2) 3-O-COH-CH2COOC2HS

16 50 50 4-H5C6-OCH2CH20-CO-H -CH3

  17 70 30 3 -H5C6-OCH2CH2O-CO H idem 18 70 30 4-HgCl4CH (C2H5) -CH2-NH-CO H idem

  19 60 40 4-H3C0-CH2CH20CH2CH20-CO- H -C2H5

70 4-H5C6-O-CH2CH2O-CO-H-C4H9

  1.5 Idem H - CH 2 CH 2 CH 2 O 4 H 9 Mixtures of disperse dyes of formula I 'with disperse dyes of formula III are given

following table II.

Table II

  Ex.% Of the dye% disperse disperse dye of formula III Formula III -CH2CH2CH2-O-C2Hs 22 65 35 ditto 23 70 20 ditto c4

24 65 35 -CH2CH2CH2-0-C4H9

25 60 40 -CH2CH2CH2-0-i-C3H7

26 80 20 -CH2CH2CH2-0-CH3

27 70 30 -CH2CH2-0-CH3

28 60 40 -CH2CH2-o-C2H5

29 80 20 -C4H9

30 12 C3H7

13 -C4E9

  ## STR2 ## Mixtures of disperse dyes of formula I, wherein R '1 represents H, and disperse dyes of formula III, wherein R 9 represents

  -CH2CH2CH2OCH2CH3 are given in table II.

  -Table III Ex.% Dye% disperse dye disperse R R

1 2

formula I formula III

50 50 H 2-0CHE3

36 70 30 H 3-CE3

  37 80. 20 H 2 -Cl 38 50 50 4-Cl H Mixtures of disperse dyes of formula I 'and disperse dyes of formulas IV to XII are given

following table IV.

Table IV

  Ex.% Of the dye% disperse disperse dye of formula I '(of formula)

39 70 30 (IV)

85 (V)

41 80 20 (VI) R Br, R12H

42 90 10 (VII)

43 75 25 (VIII)

44 80 20 (IX)

85 (X)

46 80 (VI) R1l = Cl, Rf-O-COCH3

47 85 15 (XI)

48 85 15 (XII)

49 85 15 (VI) R1l C1,12 = E

Example 50 -

  Using the method of Example 1 above,

  copula 38.5 parts of 3-cyano-6-hydroxy-1-3'-hydroxy-p-

  ethoxyethyl-4-methylpyridone-2 with a mixture of 22.3 parts of the 4-aminol, azobenzene, diazotized, and 7.86 parts of the diazotized 3,4-dichloroaniline, which gives

  a mixture of azo dyes dyeing yellow-orange.

EXAMPLE OF APPLICATION

  250 parts of a 16% aqueous paste of the dye of Example 1 are ground in a glass bead mill with 60 parts of lignin sulphonate dispersing agents until the particles obtained have been obtained. an average diameter of at most 1 μm. We separate (by filtration) the glass beads, we adjust between 7 and 8 the

  pH and the preparation is dried in an atomic dryer.

  with hot air. The fine powder obtained contains

  % of a pure dye. Part of the preparation is

  dye solution thus obtained with 4000 parts of water which is heated up to 60 and which is buffered to pH 5. This dye liquor is used to dye 100 parts of a woven polyester fiber, during 1 h to 130, in a closed dyeing apparatus. After cooling, rinsing, soaping, rinsing again, and drying, a solid orange yellow dye is obtained.

  very good general solidities.

  It may be applied by analogy to the example

  above, the products of Examples 2 to 49.

  The above example of dyeing can be repeated using, instead of the dye of Example 1, that of

  Examples 2 or 3 or the mixtures of Examples 4 to 50.

  The shade of dyes on a fiber material of

  polyester is orange yellow in all cases.

Claims (8)

  1. Disperse dye (disperse dye)   persé) characterized in that it corresponds to the formula I R II I N N N = N R0 1 R2 R3-O-R4-OH   [wherein R 1, R 'and R 2 are independently selected from hydrogen, chlorine or bromine or C 1 or C 2 alkyl or C 1 or C 2 alkoxy, and R3 and R4 are each, independently of one another, a C2 or C3 alkylene group)   2. Disperse dye of formula I according to claim   cation 1, characterized in that R1 represents a hydrogen or chlorine atom, R'1 represents a hydrogen atom, R2 represents a hydrogen atom or   chlorine or a methyl or methoxy group, and R3 and R4 represent   each feel a group of formula - CH2-CH2-.   3. Mixture of disperse dyes, characterized in that it comprises a dye of formula (I), as defined   in claims 1 or 2, with from 90 to 10% by weight of a   or several other yellow disperse dyes.   4. Mixture of disperse dyes according to claim 3,   characterized in that one or more dispersed yellow dyes are chosen   among the disperse dyestuffs of formulas (II) to (XII): Rz CH 4J. C II N = N N 0 R OH R R6 8   (wherein R5 is, as shown, in position 3 or   in position 4, and is selected from a hydrogen atom   gene or chlorine or bromine and a (C1-C8) alkoxycarbonyl group, a (C1-C3) alkoxy (C2-C3) alkoxycarbonyl group, a C2-C3 alkenyloxy (C2-alkoxy) group or C3) carbonyl, (C1-C3) alkoxy (C2-C3) alkoxy (C2-C3) alkoxycarbonyl, phenoxy (C2-C3) alkoxycarbonyl, phenylalkoxy (C1-C3) carbonyl benzylcarbonyloxy group, (C1-C8) alkylaminocarbonyl group, (C1-C8) alkylaminosulfonyl group, (C1-C3) alkyl group)   benzoyl, a phenylsulfonyloxy group, a benzyloxy-   carbonyl, a tetrahydrofuryl (C1-C3) alkoxycarbonyl group, a cyano group, a trifluoromethyl group or a C1-C7 alkoxy group, R6 represents a hydrogen atom or a nitro, C1-C8 alkoxy group carbonyl or a chlorine atom, R7 represents a hydrogen or chlorine atom, and R8 represents a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy (C2-C4) alkyl group ) or a (C1-C4) alkoxycarbonyl (C1-C2) alkyl group, CH3 CN H5C6 - O NN - N N0   Wherein R9 is (C1-C8) alkyl, (C1-C4) alkoxyalkyl (C2-C3), (C1-C4) alkylcarbonyloxyalkyl (C2) or C3), (C2-C3) alkenyloxy (C2-C3) alkoxy (C2-C3) alkyl, C1-C4-alkyl (C1-C4) alkylcarbonyloxy (C2-C3) alkoxy (C2-C3) alkyl ), a (C 1 -C 2) alkoxycarbonyloxy (C 2 or C 3) alkyl group or a group of formula CH 2 CH 2 -O-CH 2 CH 2 OH]; OCH 3 02N- - N N 6 N -N NOO OH IV;   ## STR2 ## NHCOCH3 V; _> CFil / CH2R2 -2 2 VI CH2CH2CN VI   R111 (wherein the two symbols R11 represent a chlorine or bromine atom, and R12 represents a hydrogen atom or an acetoxy group) H5C6-N = -O- S = O '- CH2 H due VII; C6H5 OH H5C6 - N = N-O-N = N CH 3 VIII; Br IX; CE2CH20COCH20C6HN 2 \ I t CH CH OCOCE OC H 2 2 2 6 5 ci X; 02N t N = N N XI; H and NO2 H3CSSO2 N = N CH3 H2? TTIIIJ t C6H5 XII.   5. Mixture of disperse dyes according to some   conque of claims 3 or 4, characterized in that   the other yellow disperse dye is a disperse dye of   form (II) or (III) according to the definition given in vending 4.   6. Process for the preparation of disperse dyes   formula I according to the definition given to   cations 1 or 2, characterized in that it comprises the coupling of an aminobenzene of formula (XIII) R1 = N = N NH N_ H2 R XIII   R2 (wherein R1, R2, R3 and R4 are as defined 1 'R'   in claims 1 or 2), after diazotation, with a   mole of a compound of formula XIV: CH CN OMAN XIV. 3R -O-R -OH   7. Process for the preparation of color mixtures   dispersants as claimed in any of claims 1   at 5, characterized in that it comprises: a) the mixture of the dyes   before or after formulation in the form of prepara-   dyes; or b) coupling, on the diazotized component of formula XIII, the coupler of formula XIV with an additional coupler, or the coupling of two different diazotized components with a coupler; or c) when it is desired to prepare a mixture of a dye of formula (I) with the analogous dye of formula (III),   in which R9 represents a (C1-C4) alkyl group -   carbonyloxy (C2-C3) alkoxy-(C2-C3) alkyl, further acylation of a portion of the disperse dye of formula I. 8. Method for dyeing or printing a material   hydrophobic fibrous material, characterized in that   takes the application of a disperse dye, according to   1 or 2, or a mixture of dyes   perses according to any one of claims 3 to 5, substrate.