GB2031927A - Dyestuffs - Google Patents

Abstract

Disperse monoazo dyestuffs having the general formula: <IMAGE> wherein R represents a hydrogen atom or an alkyl group, R<1> represents a hydrogen atom or a hydrocarbyl group, R<2> represents a hydrocarbyl group, V represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R<2>, W represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R<2>, X represents a hydrogen atom, a halogen atom, a cyano group, a nitro group or a group -CO2R<2>, Y represents a hydrogen atom, a halogen atom or an alkyl, alkoxy or alkoxycarbonyl group, and Z represents an acyl, acylamino or cyano group or the group Y, and wherein at least one of V and X is hydrogen. The dyes are applicable to synthetic textile materials for example cellulose acetates, polyamides and especially aromatic polyester textile materials

Description

SPECIFICATION Dyestuffs This invention relates to dyestuffs and more particularly to disperse monoazo dyestuffs based on secondary amine coupling components.

According to the present invention there are provided disperse monoazo dyestuffs having the generai formula:

wherein R represents a hydrogen atom or an alkyl group, which may be further substituted, R1 represents a hydrogen atom or a hydrocarbyl group, R2 represents a hydrocarbyl group, V represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R2, W represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R2, X represents a hydrogen atom, a halogen atom, a cyano group, a nitro group or a group -CO2R2, Y represents a hydrogen atom, a halogen atom or an alkyl, alkoxy or alkoxycarbonyl group, and Z represents an acyl, acylamino, or cyano group or the group y, and wherein at least one of V and X is a hydrogen atom.

The hydrocarbyl groups represented by R1 and R2 may be alkyl, alkenyl, cycloalkyl, aralkyl or optionally substituted aryl groups.

Examples of alkyl groups represented by R, 131,132 and Y are methyl, ethyl, n-propyl, isopropyl, n-butyl isobutyl, n-pentyl, sec-pentyl, n-hexyl, 2-ethylhexyl and n-octyl.

An example of a cycloalkyl group represented by R' and R2 is cyclohexyl.

Examples of aralkyl groups represented by R' and R2 are benzyl and ss-phenylethyl.

Examples of aryl and substituted aryl groups represented by R1 and R2 are phenyl, tolyl and chlorophenyl.

Examples of alkoxy groups represented by y are methoxy and ethoxy, and examples of alkoxycarbonyl groups represented by Y are methoxycarbonyl, ethoxycarbonyl and n-butoxycarbonyl.

Examples of halogen atoms represented by V, W, X and Y are chlorine and bromine.

Examples of acyl groups; represented by Z are acetyl and propionyl. The acylamino groups which may be represented by Z include formylamino, alkylcarbonylamino, substituted alkylcarbonylamino, alkenylcarbonylamino, arylcarbonylamino, aralkylcarbonylamino, cycloalkylcarbonylamino, alkylsulphonylamino, arylsulphonylamino, alkoxycarbonylamino, alkoxyalkoxycarbonylamino, aminocarbonylmino and alkylaminocarbonylamino groups.

Examples of such groups include acetylamino, propionylamino, butyrylamino, pivaloylamino, hexanoyla minx, benzoylamino, toluoylamino, phenylacetylamino, cyclo hexylcarbonylamino, methylsulphonylamino, p-toluenesulphonylamino, methoxycarbonylamino and t3-methoxyethoxycarbonylamino.

It is preferred that the alkyl and alkoxy groups represented by Y and the various alkyl and alkoxy radicals present in the acylamino groups are lower alkyl and lower alkoxy groups.

In this specification the terms "lower alkyl" and "lower alkoxy" mean alkyl and alkoxy groups respectively which contain from 1 to 4 carbon atoms.

According to a further feature of the invention there is provided a processforthe manufactureofdisperse monoazo dyestuffs having the above-defined formula (I) which comprises diazotising an arylamine having the formula:

and coupling the diazonium compound so obtained on to a coupling component having the formula:

wherein R, R', R2, V, W, X, Y and Z have the meanings stated above.

Examples of the arylamines of formula (II) which may be used in the process are 2,5.dichlorn-4- sulphonylanil ine, 2,5-dichloro-4-(N-n-butylaminosulphonyl)aniline, 2-chloro-4-(Nethylaminosulphonyl)aniline, 2,6-dichloro-4-(N-ethyl-aminosulphonyl)aniline, 2-bromo4-(Nethylanimosulphonyl)anilihe, 2,6-dibromo-4-(N-ethylaminosulphonyl)aniline, 2-cyano4-(Nethylaminosulphonyl)aniline, 2-(methoxycarbonyl)-4-N-(ethylaminosulphonyl)aniline, 2,5-dicyano4-(N- ethylaminosulphonyl)aniline, 2,5-di(methoxycarbonyl)-4-N-(ethylaminosulphonyl)aniline, 2-nitro4-N- (ethylaminosulphonyl)aniline, 4-2-methylaminosulphonyIaniline4-prnpylaminosulphonylaniIine, 4octylaminosulphonylaniline, 4-('-ethylhexyl)aminosulphonylaniline, 4-diethylaminosulphonylaniline, 4-(Nmethyl-N-phenylamino)sulphonylaniline, 4-(o-tolylamino)sulphonylaniline, 4-(m-tolylamino)sulphonyl, 4 (p-tolylamine)sulphonylaniline, 4-(N-methyl-N-o-chlorophenylamino)sulphonylaniline, 4-(N-methyl-N-Mchlorophenylamino(sulphonylaniline, 4-(N-methyl-N-p-chlorophenylamin)sulphonylaniline, 4 (phenylaminosulponyl)aniline, 4-(benzylaminosulponyl)aniline, 4-[(phenylethyl)aminosulponyl]aniline and 4-cyclohexaminosulphonylaniline.

Examples of the coupling components of formula (III) which may be used are N-sec-pentyl-maminoacetanilide, N-isopropyl-m-aminoacetanilide, 2,5-dimethyl-N-methylaniline, 2,5-dimethyl-Nethylaniline, 2,5-dimethyl-N-n-propylaniline, 2,5-dimethyl-N-butylaniline, 2,5-dimethyl-N-pentylaniline, 2,5dimethyl-N-hexylaniline, 2,5-dimethyl-N-octylaniline, N-isobutylaniline, N-isobutyl-m-toluidine, N-ethyl-otoluidine, 2-chloro-N-isopropyl-aniline, 2-methyi-N-isopropylaniline, 2-methoxy-N-isopropylaniline, 2methoxycarbonyl-N-isopropylaniline, 3-cyano-N-isobutylaniline, 3-acetyl-N-isobutylaniline, 3-propionyl-Nisobutylaniline, 3-methoxycarbonyl-N-isobutylaniline, 3-ethoxycarbonyl-N-isobutyl-aniline, m-formylamino N-sec-pentylaniline, m-pripionylamino-N-sec-pentylaniline, m-butyrylamino-N-sec-pentylaniline, mpivaloylamino-N-sec-pentylaniline, m-hexanoylamino-N-sec-pentylaniline, m-benzoylamino-N-secpentylaniline, m-toluoylamino-N-sec-pentylaniline, m-phenylacetylamino-N-sec-pentylaniline, mcyclohexylcarbonylamino-N-sec-pentylaniline, m-methylsulphonylamino-N-sec-pentylaniline m-(ptoluenesulphonylamino)-N-sec-pentylaniline, m-methoxycarbonylamino-N-sec-pentylaniline, m-(ss- methoxyethoxycarbonylamino)-N-sec-pentylaniline, m-aminocarbonylamino-N-sec-pentylaniline and methylaminocarbonyl-N-sec-pentylaniline.

In the above coupling components, "sec-pentyl" refers to the radical having the structure (C2H5)2CH-.

The diazotisation and coupling may be carried out by known method for these reactions. For example, the process may be carried out by adding sodium nitrate to a solution or dispersion of the arylamine in hydrochloric acid, sulphuric acid, an aqueous solution of sulphuric acid or a mixture of hydrochloric acid or sulphuric acid with an organic acid such as acetic and/or propionic acid, or by stirring the arylamine with nitrosylsulphuric acid, followed by addition of the resulting solution or dispersion of the diazonium compound thus obtained to a solution of the coupling component in water or in a mixture of water and a water-miscible organic liquid, if necessary adjusting the pH of the mixture to facilitate the coupling reaction, and final!y isolating the resulting dyestuff by conventional methods.

According to a yet further feature of the invention there is provided a method for the colouration of synthetic textile materials which comprises applying to the said synthetic textile materials from an aqueous medium a monoazo dyestuff as hereinbefore defined.

The dyestuffs of the present invention may be applied to synthetic textile materials by dyeing, padding or printing methods in the form of aqueous dispersions which are prepared by conventional methods, for example, by milling the dyestuffs with water and a suitable dispersing agent such as the sodium salt of a naphthalene-2-sulponic acid/formaldehyde condensate.

Examples of synthetic textile materials to which the dyestuffs may be applied are textile materials fabricated from secondary cellulose acetate, cellulose triacetate, polyamides such as poly(hexamethylene adipamide) and above all aromatic polyesters such as polyethylene terephthalate.

The dyestuffs may also be applied to synthetic textile materials by known methods of transfer colour printing such as sublimation transfer printing, optionally under reduced pressure, and wet transfer printing.

The dyestuffs also find application for the melt colouration of polymers such as aromatic polyesters.

When applied to synthetic textile materials as indicated above, the dyestuffs of the present invention provide scarlet shades having good fastness to the tests conventionally applied to coloured synthetic textile materials, and in particular good dyeing properties and tinctorial strength.

The invention is illustrated but not limited by the following Examples in which parts and percentages are by weight.

Example 1 2,5-Dichloro-4-sulphamoylaniline (4.82 parts) is dissolved in a mixture of glacial acetic acid (40 parts) and concentrated hydrochloric acid (6 parts) and diazotised at 0-5"C by addition of 2N-aqueous sodium nitrate solution (10 parts). The solution of the diazonium compound so obtained is added to a mixture of N-(1-ethylpropyl)-m-aminoacetanilide (4.4 parts) in acetic acid (50 parts) and ice water (200 parts). The mixture is stirred for 3 hours, after which time the precipitated dyestuff is collected, washed well with water and recrystallised from aqueous acetone.

When applied in the form of an aqueous dispersion to aromatic polyester textile material a bright scarlet shade is obtained.

The following table gives further Examples of dyes of the invention which may be obtained by diazotising the amines listed in the second column and coupling with the secondary amines listed in the third column.

The fourth column gives the shades obtained on aromatic polyester textile material.

Diazo D5aw Component Goupling Co po ent shade Cl 2 ew 2 c2a5 'harlot 3 C4, CS?- Cl a CE5 CL 4 'sCs(CS3)2 I c ! a=?1, x," ce, p S:e | cOvplk6 Coo,ooet 3 . , .

5 e2llSwIw2 -(c3), scubt d CL 3 6 c,2=2 vNs Cg3) 49 2 CL 32 CL 7 Ca'C HI a pia m.:o | Coapl:.=g Cossent suac CL 8 (al3)zw z tcE3)2 CL 9 Ca)oc.C,2q.ao tO 2 2vY2

DIrD Ca.inacot I | Coupl5ng I 9ud+ CL 11 Ct 2 N - (Z(CS3)2 aa1at 12 2M2 MR,aIC2u3 Or n C,3 13 oupl ) =o Co-ponese coupling Coopcsent 14 Oa2ND2 FCHC2115 Or nv "3 15 (CS31 2NHI2 (c|92 se-rlee CL 16 a ms Hadd 'a H'=plc Dia Cemcnt Coupliq "oaocat Cl 17 (Ca3)1O MCS3 1at CL 18 -C17 Sn1at HI(D(z3 19 a ,arlet

. Exu=ple Diam C03pnnent Coupling Component HIC,,, Cl 3 20 cc"r'r"z- 2 bN15{9 HIM Scarlet C1 N COCa3 Z1 6 NE Crana' 22 wE 2 'BIa2e5 Scarlet "3 jfra-e aro bo.mt Coupling Cacpe3cnt I SuedC Br OC83 23 CzaTDza""fs Scarlet Br 24 Ha\coc3lj ,Bc2H5 cm "3 25 ("3)?sDa " Reddian orange . C.;rrinant ç 'flede a"2"5 .3 N'dM 26 tC15 I SO w, cag5 dand1gdhe "3 27 ("3)?SO2NH2.2 HICOdE 28 n 9 )LC4!9 orange

z,aopl. CWEne COpdOe.t Coupli Cccent Be-Ba 2, (eE3)21150 42 W2. 5 Bed RBX:H 30 a nc Bla'eh red 31 " T N CE(CE3)2 ROE4d6X1 laaople D{.W Iro CoJolmr Col:ponent Be-Ba 32 (CE3)zNX26g2 t}- ezX5 sCrçe LrrW 4 1 I '(a&commat;~m"Hs CS CL HICOC B13 3W cg3ES)z b GN~Cl5(CD3)2 .

Cl 1apple rte coRrDD.e Cncot I Coupitag panant ) Shade Cl 35 3 2 SN)6C;5(CS3)2 L Xt 2Cl2 32 36 'B(a(cr5)a a 7"3)2 MCC 37 a McH("3)2

Zrepl Di w Btane E | een6 cO:p=auent Be-Be el NrdOOOQ3 38 tt bt no - it - ":i"-"H Scarlet . CS C HICOOC B 39 gShCg(CE3)2 40 CaCc52 a i=ple t Diana Co~ponent | Coupling Cospoúent Be-Be MC2B5 i1 "31?22 2 bX N'dCd(C=-3)2 Scarlet I I Q a 5 cE3 n 43 Ca(C)2 Cm-a 4 h=ple Dluo Corpnnest Cnuplin6 Coespanest shady Cl 0' 4i ("3)2wEo2 M2 MCB(C)2 CL "3 45 CM cLw HIcH-C Beddiak- CL "3I orange Ca 46 fl'BC

aapla Cespme e Coapanent c-pltq Cne203ent 47 Cg9NNsD2 p2 OCb Ca CCS *8 t (:1MCa Brarlat 49 T C* Baddiek OEBR3 3 Impla Di w cnepDnent Cop1Iag Cceponent I Be-Be P "z"c" 30 C42 ap.-p 2 g - C* Scarlet Cl Nldmlrd - ca2 51 aICCCS Sd 3 Reddleh BBCa2CS Impla Bt ',op=t Coupling Canpoot Be-Be MEBE C B 53 e5'dE22 ea CS2CS(Ca3)2 Scarlet

Claims (8)

1. A disperse monoazo dyestuff having the general formula:

wherein R represents a hydrogen atom or an alkyl group which may be further substituted, R' represents a hydrogen atom or a hydrocarbyl group, R2 represents a hydrocarbyl group, V represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R2, W represents a hydrogen atom, a halogen atom, a cyano group or a group -CO2R2, X represents a hydrogen atom, a halogen atom, a cyano group, a nitro group or a group -CO2R2, Y represents a hydrogen atom, a halogen atom or an alkyl, alkoxy or alkoxycarbonyl group, and Z represents an acyl, acylamino or cyano group or the group Y, and wherein at least one of V and X is hydrogen.

2. A disperse monoazo dyestuff as claimed in claim 1 and specifically identified herein.

3. A process for the manufacture of a disperse monoazo dyestuff as defined in claim 1 which comprises diazotising an arylamine having the formula:

and coupling the diazonium compound so obtained with a coupling component having the formula:

wherein R, R1, R2, V, W, X, Y and Z have the meanings stated in claim 1,

4. A process as claimed in claim 3 conducted substantially as hereinbefore described with reference to any one of the foregoing Examples.

5. A disperse monoazo dyestuff whenever manufactured by a method claimed in claim 3 or claim 4.

6. A process for the colouration of synthetic textile materials which comprises applying thereto a disperse monoazo dyestuff as claimed in any one of claims 1, 2 and 5.

7. A process as claimed in claim 6 wherein the synthetic textile material is an aromatic polyester textile material.

8. Synthetic textile materials whenever coloured by the process claimed in claim 6 or claim 7.