Disperse azo dyes

Abstract

The present invention relates to disperse azo dyes of formula ##STR00001##
wherein R.sub.1 is bromo, nitro, cyano, methyl, methoxy or trifluoromethyl; R.sub.2 is hydrogen, chloro, bromo or trifluoromethyl; R.sub.3 is hydrogen, chloro, bromo, methoxy, trifluoromethyl, nitro or cyano; and R.sub.4 is methyl, ethyl, n-propyl, 2-methoxyethyl, methoxycarbonylmethyl or 2-methoxycarbonylethyl;
with the proviso that R.sub.1 is cyano in case R.sub.2 denotes chloro or bromo,
to a process for the preparation of such dyes and to their use in the dyeing or printing of semi-synthetic and, especially, synthetic hydrophobic fibre materials, more especially textile materials.

Claims

1. A dye of formula ##STR00007## wherein R.sub.1 is methyl, methoxy or trifluoromethyl; R.sub.2 is hydrogen, chloro, or trifluoromethyl; R.sub.3 is hydrogen, chloro, bromo, methoxy, trifluoromethyl, nitro or cyano; and R.sub.4 is 2-methoxyethyl, methoxycarbonylmethyl or 2-methoxycarbonylethyl.

2. The dye of formula (1) according to claim 1, wherein R.sub.1 is methyl.

3. The dye of formula (1) according to claim 1, wherein R.sub.2 is chloro.

4. The dye of formula (1) according to claim 1, wherein R.sub.3 is hydrogen.

5. A process for the preparation of the dye of formula (1) according to claim 1, which comprises diazotising a compound of formula ##STR00008## and coupling the diazonium compound so obtained to a coupling component of formula ##STR00009## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the meanings given for formula (1) in claim 1.

6. A dye mixture comprising at least one dye of formula (1) according to claim 1 and at least one further dye selected from the group consisting of C.I. Disperse Blue 60, C.I. Disperse Blue 79:1, C.I. Disperse Blue 72:2, C.I. Disperse Blue 148, C.I. Disperse Blue 149, C.I. Disperse Blue 165, C.I. Disperse Blue 165:1, C.I. Disperse Blue 207, C.I. Disperse Blue 284, C.I. Disperse Blue 295, C.I. Disperse Blue 316, C.I. Disperse Blue 337, C.I. Disperse Blue 354, C.I. Disperse Blue 366, C.I. Disperse Blue 367, C.I. Disperse Blue 368, C.I. Disperse Blue 376, C.I. Disperse Blue 378, C.I. Disperse Blue 380, C.I. Disperse Green 9, C.I. Disperse Violet 107, a compound of the formula ##STR00010## wherein R.sub.1 is ethyl, R.sub.5 is hydrogen, R.sub.5 is acetylamino, R.sub.7 is ethyl, 2-methoxyethyl, n-propyl, n-butyl, 2-cyanoethyl, 1-methoxycarbonylethyl, 1-methoxycarbonylmethyl, allyl, 2-methoxycarbonylethyl, hydrogen, 2-cyanoethyl, benzyl or n-butyl and wherein when R.sub.7 is ethyl, R.sub.8 is methyl, ethyl, n-propyl, n-butyl, benzyl, 2-methoxyethyl, 2-cyanoethyl, 2-phenylethyl, ethoxycarbonylmethyl, 2-methoxycarbonylethyl, 2-acetoxyethyl, 2-hydroxy-3-phenoxypropyl, 2-ethoxycarbonylethyl, 2-hydroxy-3-isopropoxypropyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 4-nitrobenzyl,4-methoxybenzyl, 3-methoxybenzyl, 3-phenoxypropyl or 4-acetoxybutyl and wherein when R.sub.7 is 2-methoxyethyl, R.sub.8 is 2-methoxyethyl or benzyl and wherein when R.sub.7 is n-propyl, R.sub.8 is n-propyl and wherein when R.sub.7 is n-butyl, R.sub.8 is n-butyl and wherein when R.sub.7 is 2-cyanoethyl, R.sub.8 is benzyl or 2-methoxycarbonylethyl and wherein when R.sub.7 is 1-methoxycarbonylethyl, R.sub.8 is 1-methoxycarbonylmethyl and wherein when R.sub.7 is methoxycarbonylmethyl, R.sub.8 is methoxycarbonylmethyl and wherein when R.sub.7 is allyl, R.sub.8 is allyl and wherein when R.sub.7 is 2-methoxycarbonylethyl, R.sub.8 is 2-ethoxycarbonylethyl or 2-methoxycarbonylethyl and wherein when R.sub.7 is hydrogen, R.sub.8 is 1-methoxycarbonylethyl and wherein when R.sub.7 is 2-cyanoethyl, R.sub.8 is 2-methoxycarbonylethyl and wherein when R.sub.7 is benzyl, R.sub.8 is 2-methoxycarbonylethyl and wherein when R.sub.7 is n-butyl, R.sub.8 is n-butyl or benzyl, the compounds of formulas (101)-(106) ##STR00011## and the compounds of formulas II-2, II-3, II-4 ##STR00012## ##STR00013##

7. A process for dyeing or printing semi-synthetic or synthetic hydrophobic fibre material which comprises applying to or incorporating into the hydrophobic fibre material at least one dye of formula (1) according to claim 1 or the dye mixture according to claim 6.

8. A process according to claim 7, wherein the hydrophobic fibre material contains polyester fibres.

9. A material dyed or printed according to claim 7.

Description

I. PREPARATION EXAMPLES

Example I.1

(1) A. Diazotation

(2) 20 g of conc. sulfuric acid are placed in a laboratory reaction apparatus. After addition of 5 g ice the solution is cooled to RT. At this temperature, 6.01 g of 2-bromo-4-nitro-6-cyanoaniline are added. After being stirred for 30 min at RT and cooling down to 10° C., 8.2 g of 40% nitrosylsulfuric acid are added dropwise. The reaction mixture is stirred for a further 60 min at 10° C. Afterwards, the excess nitrite is destroyed by addition of sulfamic acid.

(3) B. Coupling

(4) 7.83 g of finely powdered N-3-nitrobenzyl-N-ethyl-3-acetylaminoaniline prepared according to the method described in Example 1a of FR 2008404 are suspended in 10 ml ethanol and mixed with 20 g of ice.

(5) Under stirring the solution of the diazonium salt obtained in step A is added dropwise within 60 min. The reaction mixture is stirred at RT over night. After filtration, washing and drying 11.75 g (83%) of the dye of formula (101) are obtained.

(6) ##STR00005##

(7) The dyes (102)-(1252) listed in Table 1 are prepared analogously to the process described in Example I.1.

(8) TABLE-US-00001 TABLE 1 (1) (λ.sub.max = wavelength of the absorption maximum) Compound R.sub.1 R.sub.2 R.sub.3 R.sub.4 λ.sub.max/nm 101 CN Br m-NO.sub.2 —C.sub.2H.sub.5 573 102 CN Br m-NO.sub.2 —CH.sub.3 103 CN Br m-NO.sub.2 n-C.sub.3H.sub.7 104 CN Br m-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 105 CN Br m-NO.sub.2 —CH.sub.2CO—OCH.sub.3 106 CN Br m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 107 CN Br m-CF.sub.3 —CH.sub.3 108 CN Br m-CF.sub.3 —C.sub.2H.sub.5 109 CN Br m-CF.sub.3 n-C.sub.3H.sub.7 110 CN Br m-CF.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 111 CN Br m-CF.sub.3 —CH.sub.2CO—OCH.sub.3 112 CN Br m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 113 CN Br p-OCH.sub.3 —CH.sub.3 114 CN Br p-OCH.sub.3 —C.sub.2H.sub.5 115 CN Br p-OCH.sub.3 n-C.sub.3H.sub.7 116 CN Br p-OCH.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 117 CN Br p-OCH.sub.3 —CH.sub.2CO—OCH.sub.3 118 CN Br p-OCH.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 119 CN Br p-CN —CH.sub.3 120 CN Br p-CN —C.sub.2H.sub.5 121 CN Br p-CN n-C.sub.3H.sub.7 122 CN Br p-CN —CH.sub.2CH.sub.2OCH.sub.3 123 CN Br p-CN —CH.sub.2CO—OCH.sub.3 124 CN Br p-CN —CH.sub.2CH.sub.2CO—OCH.sub.3 125 CN Br p-Cl —CH.sub.3 126 CN Br p-Cl —C.sub.2H.sub.5 127 CN Br p-Cl n-C.sub.3H.sub.7 128 CN Br p-Cl —CH.sub.2CH.sub.2OCH.sub.3 129 CN Br p-Cl —CH.sub.2CO—OCH.sub.3 130 CN Br p-Cl —CH.sub.2CH.sub.2CO—OCH.sub.3 131 CN Br p-Br —CH.sub.3 132 CN Br p-Br —C.sub.2H.sub.5 133 CN Br p-Br n-C.sub.3H.sub.7 134 CN Br p-Br —CH.sub.2CH.sub.2OCH.sub.3 135 CN Br p-Br —CH.sub.2CO—OCH.sub.3 136 CN Br p-Br —CH.sub.2CH.sub.2CO—OCH.sub.3 137 CN Br p-NO.sub.2 —CH.sub.3 138 CN Br p-NO.sub.2 —C.sub.2H.sub.5 139 CN Br p-NO.sub.2 n-C.sub.3H.sub.7 140 CN Br p-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 141 CN Br p-NO.sub.2 —CH.sub.2CO—OCH.sub.3 142 CN Br p-NO.sub.2 —CH.sub.2CH.sub.2CO—OCH.sub.3 143 CN Br H —CH.sub.3 578 144 CN Br H —C.sub.2H.sub.5 582 145 CN Br H n-C.sub.3H.sub.7 587 146 CN Br H —CH.sub.2CH.sub.2OCH.sub.3 572 147 CN Br H —CH.sub.2CO—OCH.sub.3 555 148 CN Br H —CH.sub.2CH.sub.2CO—OCH.sub.3 571 149 CN Cl m-NO.sub.2 —CH.sub.3 150 CN Cl m-NO.sub.2 —C.sub.2H.sub.5 151 CN Cl m-NO.sub.2 n-C.sub.3H.sub.7 152 CN Cl m-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 153 CN Cl m-NO.sub.2 —CH.sub.2CO—OCH.sub.3 154 CN Cl m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 155 CN Cl m-CF.sub.3 —CH.sub.3 156 CN Cl m-CF.sub.3 —C.sub.2H.sub.5 157 CN Cl m-CF.sub.3 n-C.sub.3H.sub.7 158 CN Cl m-CF.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 159 CN Cl m-CF.sub.3 —CH.sub.2CO—OCH.sub.3 160 CN Cl m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 161 CN Cl p-OCH.sub.3 —CH.sub.3 162 CN Cl p-OCH.sub.3 —C.sub.2H.sub.5 163 CN Cl p-OCH.sub.3 n-C.sub.3H.sub.7 164 CN Cl p-OCH.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 165 CN Cl p-OCH.sub.3 —CH.sub.2CO—OCH.sub.3 166 CN Cl p-OCH.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 167 CN Cl p-CN —CH.sub.3 168 CN Cl p-CN —C.sub.2H.sub.5 169 CN Cl p-CN n-C.sub.3H.sub.7 170 CN Cl p-CN —CH.sub.2CH.sub.2OCH.sub.3 171 CN Cl p-CN —CH.sub.2CO—OCH.sub.3 172 CN Cl p-CN —CH.sub.2CH.sub.2CO—OCH.sub.3 173 CN Cl p-Cl —CH.sub.3 174 CN Cl p-Cl —C.sub.2H.sub.5 175 CN Cl p-Cl n-C.sub.3H.sub.7 176 CN Cl p-Cl —CH.sub.2CH.sub.2OCH.sub.3 177 CN Cl p-Cl —CH.sub.2CO—OCH.sub.3 178 CN Cl p-Cl —CH.sub.2CH.sub.2CO—OCH.sub.3 179 CN Cl p-Br —CH.sub.3 180 CN Cl p-Br —C.sub.2H.sub.5 181 CN Cl p-Br n-C.sub.3H.sub.7 182 CN Cl p-Br —CH.sub.2CH.sub.2OCH.sub.3 183 CN Cl p-Br —CH.sub.2CO—OCH.sub.3 184 CN Cl p-Br —CH.sub.2CH.sub.2CO—OCH.sub.3 185 CN Cl p-NO.sub.2 —CH.sub.3 186 CN Cl p-NO.sub.2 —C.sub.2H.sub.5 187 CN Cl p-NO.sub.2 n-C.sub.3H.sub.7 188 CN Cl p-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 189 CN Cl p-NO.sub.2 —CH.sub.2CO—OCH.sub.3 550 190 CN Cl p-NO.sub.2 —CH.sub.2CH.sub.2CO—OCH.sub.3 565 191 CN Cl H —CH.sub.3 578 192 CN Cl H —C.sub.2H.sub.5 585 193 CN Cl H n-C.sub.3H.sub.7 590 194 CN Cl H —CH.sub.2CH.sub.2OCH.sub.3 577 195 CN Cl H —CH.sub.2CO—OCH.sub.3 560 196 CN Cl H —CH.sub.2CH.sub.2CO—OCH.sub.3 570 197 CN CF.sub.3 m-NO.sub.2 —CH.sub.3 198 CN CF.sub.3 m-NO.sub.2 —C.sub.2H.sub.5 199 CN CF.sub.3 m-NO.sub.2 n-C.sub.3H.sub.7 200 CN CF.sub.3 m-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 201 CN CF.sub.3 m-NO.sub.2 —CH.sub.2CO—OCH.sub.3 202 CN CF.sub.3 m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 203 CN CF.sub.3 m-CF.sub.3 —CH.sub.3 204 CN CF.sub.3 m-CF.sub.3 —C.sub.2H.sub.5 205 CN CF.sub.3 m-CF.sub.3 n-C.sub.3H.sub.7 206 CN CF.sub.3 m-CF.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 207 CN CF.sub.3 m-CF.sub.3 —CH.sub.2CO—OCH.sub.3 208 CN CF.sub.3 m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 209 CN CF.sub.3 p-OCH.sub.3 —CH.sub.3 210 CN CF.sub.3 p-OCH.sub.3 —C.sub.2H.sub.5 211 CN CF.sub.3 p-OCH.sub.3 n-C.sub.3H.sub.7 212 CN CF.sub.3 p-OCH.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 213 CN CF.sub.3 p-OCH.sub.3 —CH.sub.2CO—OCH.sub.3 214 CN CF.sub.3 p-OCH.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 215 CN CF.sub.3 p-CN —CH.sub.3 216 CN CF.sub.3 p-CN —C.sub.2H.sub.5 217 CN CF.sub.3 p-CN n-C.sub.3H.sub.7 218 CN CF.sub.3 p-CN —CH.sub.2CH.sub.2OCH.sub.3 219 CN CF.sub.3 p-CN —CH.sub.2CO—OCH.sub.3 220 CN CF.sub.3 p-CN —CH.sub.2CH.sub.2CO—OCH.sub.3 221 CN CF.sub.3 p-Cl —CH.sub.3 222 CN CF.sub.3 p-Cl —C.sub.2H.sub.5 223 CN CF.sub.3 p-Cl n-C.sub.3H.sub.7 224 CN CF.sub.3 p-Cl —CH.sub.2CH.sub.2OCH.sub.3 225 CN CF.sub.3 p-Cl —CH.sub.2CO—OCH.sub.3 226 CN CF.sub.3 p-Cl —CH.sub.2CH.sub.2CO—OCH.sub.3 227 CN CF.sub.3 p-Br —CH.sub.3 228 CN CF.sub.3 p-Br —C.sub.2H.sub.5 229 CN CF.sub.3 p-Br n-C.sub.3H.sub.7 230 CN CF.sub.3 p-Br —CH.sub.2CH.sub.2OCH.sub.3 231 CN CF.sub.3 p-Br —CH.sub.2CO—OCH.sub.3 232 CN CF.sub.3 p-Br —CH.sub.2CH.sub.2CO—OCH.sub.3 233 CN CF.sub.3 p-NO.sub.2 —CH.sub.3 234 CN CF.sub.3 p-NO.sub.2 —C.sub.2H.sub.5 235 CN CF.sub.3 p-NO.sub.2 n-C.sub.3H.sub.7 236 CN CF.sub.3 p-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 237 CN CF.sub.3 p-NO.sub.2 —CH.sub.2CO—OCH.sub.3 238 CN CF.sub.3 p-NO.sub.2 —CH.sub.2CH.sub.2CO—OCH.sub.3 239 CN CF.sub.3 H —CH.sub.3 240 CN CF.sub.3 H —C.sub.2H.sub.5 241 CN CF.sub.3 H n-C.sub.3H.sub.7 242 CN CF.sub.3 H —CH.sub.2CH.sub.2OCH.sub.3 242 CN CF.sub.3 H —CH.sub.2CO—OCH.sub.3 244 CN CF.sub.3 H —CH.sub.2CH.sub.2CO—OCH.sub.3 245 CN H m-NO.sub.2 —CH.sub.3 246 CN H m-NO.sub.2 —C.sub.2H.sub.5 247 CN H m-NO.sub.2 n-C.sub.3H.sub.7 248 CN H m-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 249 CN H m-NO.sub.2 —CH.sub.2CO—OCH.sub.3 250 CN H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 251 CN H m-CF.sub.3 —CH.sub.3 252 CN H m-CF.sub.3 —C.sub.2H.sub.5 253 CN H m-CF.sub.3 n-C.sub.3H.sub.7 254 CN H m-CF.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 255 CN H m-CF.sub.3 —CH.sub.2CO—OCH.sub.3 256 CN H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 257 CN H p-OCH.sub.3 —CH.sub.3 258 CN H p-OCH.sub.3 —C.sub.2H.sub.5 259 CN H p-OCH.sub.3 n-C.sub.3H.sub.7 260 CN H p-OCH.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 261 CN H p-OCH.sub.3 —CH.sub.2CO—OCH.sub.3 262 CN H p-OCH.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 263 CN H p-CN —CH.sub.3 264 CN H p-CN —C.sub.2H.sub.5 265 CN H p-CN n-C.sub.3H.sub.7 266 CN H p-CN —CH.sub.2CH.sub.2OCH.sub.3 267 CN H p-CN —CH.sub.2CO—OCH.sub.3 268 CN H p-CN —CH.sub.2CH.sub.2CO—OCH.sub.3 269 CN H p-Cl —CH.sub.3 270 CN H p-Cl —C.sub.2H.sub.5 271 CN H p-Cl n-C.sub.3H.sub.7 272 CN H p-Cl —CH.sub.2CH.sub.2OCH.sub.3 273 CN H p-Cl —CH.sub.2CO—OCH.sub.3 274 CN H p-Cl —CH.sub.2CH.sub.2CO—OCH.sub.3 275 CN H p-Br —CH.sub.3 276 CN H p-Br —C.sub.2H.sub.5 277 CN H p-Br n-C.sub.3H.sub.7 278 CN H p-Br —CH.sub.2CH.sub.2OCH.sub.3 279 CN H p-Br —CH.sub.2CO—OCH.sub.3 280 CN H p-Br —CH.sub.2CH.sub.2CO—OCH.sub.3 281 CN H p-NO.sub.2 —CH.sub.3 282 CN H p-NO.sub.2 —C.sub.2H.sub.5 283 CN H p-NO.sub.2 n-C.sub.3H.sub.7 284 CN H p-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 285 CN H p-NO.sub.2 —CH.sub.2CO—OCH.sub.3 286 CN H p-NO.sub.2 —CH.sub.2CH.sub.2CO—OCH.sub.3 287 CN H H —CH.sub.3 288 CN H H —C.sub.2H.sub.5 545 289 CN H H n-C.sub.3H.sub.7 290 CN H H —CH.sub.2CH.sub.2OCH.sub.3 291 CN H H —CH.sub.2CO—OCH.sub.3 292 CN H H —CH.sub.2CH.sub.2CO—OCH.sub.3 293 NO.sub.2 CF.sub.3 m-NO.sub.2 —CH.sub.3 294 NO.sub.2 CF.sub.3 m-NO.sub.2 —C.sub.2H.sub.5 295 NO.sub.2 CF.sub.3 m-NO.sub.2 n-C.sub.3H.sub.7 296 NO.sub.2 CF.sub.3 m-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 297 NO.sub.2 CF.sub.3 m-NO.sub.2 —CH.sub.2CO—OCH.sub.3 298 NO.sub.2 CF.sub.3 m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 299 NO.sub.2 CF.sub.3 m-CF.sub.3 —CH.sub.3 300 NO.sub.2 CF.sub.3 m-CF.sub.3 —C.sub.2H.sub.5 301 NO.sub.2 CF.sub.3 m-CF.sub.3 n-C.sub.3H.sub.7 302 NO.sub.2 CF.sub.3 m-CF.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 303 NO.sub.2 CF.sub.3 m-CF.sub.3 —CH.sub.2CO—OCH.sub.3 304 NO.sub.2 CF.sub.3 m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 305 NO.sub.2 CF.sub.3 p-OCH.sub.3 —CH.sub.3 306 NO.sub.2 CF.sub.3 p-OCH.sub.3 —C.sub.2H.sub.5 307 NO.sub.2 CF.sub.3 p-OCH.sub.3 n-C.sub.3H.sub.7 308 NO.sub.2 CF.sub.3 p-OCH.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 309 NO.sub.2 CF.sub.3 p-OCH.sub.3 —CH.sub.2CO—OCH.sub.3 310 NO.sub.2 CF.sub.3 p-OCH.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 311 NO.sub.2 CF.sub.3 p-CN —CH.sub.3 312 NO.sub.2 CF.sub.3 p-CN —C.sub.2H.sub.5 313 NO.sub.2 CF.sub.3 p-CN n-C.sub.3H.sub.7 314 NO.sub.2 CF.sub.3 p-CN —CH.sub.2CH.sub.2OCH.sub.3 315 NO.sub.2 CF.sub.3 p-CN —CH.sub.2CO—OCH.sub.3 316 NO.sub.2 CF.sub.3 p-CN —CH.sub.2CH.sub.2CO—OCH.sub.3 317 NO.sub.2 CF.sub.3 p-Cl —CH.sub.3 318 NO.sub.2 CF.sub.3 p-Cl —C.sub.2H.sub.5 319 NO.sub.2 CF.sub.3 p-Cl n-C.sub.3H.sub.7 320 NO.sub.2 CF.sub.3 p-Cl —CH.sub.2CH.sub.2OCH.sub.3 321 NO.sub.2 CF.sub.3 p-Cl —CH.sub.2CO—OCH.sub.3 322 NO.sub.2 CF.sub.3 p-Cl —CH.sub.2CH.sub.2CO—OCH.sub.3 323 NO.sub.2 CF.sub.3 p-Br —CH.sub.3 324 NO.sub.2 CF.sub.3 p-Br —C.sub.2H.sub.5 325 NO.sub.2 CF.sub.3 p-Br n-C.sub.3H.sub.7 326 NO.sub.2 CF.sub.3 p-Br —CH.sub.2CH.sub.2OCH.sub.3 327 NO.sub.2 CF.sub.3 p-Br —CH.sub.2CO—OCH.sub.3 328 NO.sub.2 CF.sub.3 p-Br —CH.sub.2CH.sub.2CO—OCH.sub.3 329 NO.sub.2 CF.sub.3 p-NO.sub.2 —CH.sub.3 330 NO.sub.2 CF.sub.3 p-NO.sub.2 —C.sub.2H.sub.5 331 NO.sub.2 CF.sub.3 p-NO.sub.2 n-C.sub.3H.sub.7 332 NO.sub.2 CF.sub.3 p-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 333 NO.sub.2 CF.sub.3 p-NO.sub.2 —CH.sub.2CO—OCH.sub.3 334 NO.sub.2 CF.sub.3 p-NO.sub.2 —CH.sub.2CH.sub.2CO—OCH.sub.3 335 NO.sub.2 CF.sub.3 H —CH.sub.3 336 NO.sub.2 CF.sub.3 H —C.sub.2H.sub.5 337 NO.sub.2 CF.sub.3 H n-C.sub.3H.sub.7 338 NO.sub.2 CF.sub.3 H —CH.sub.2CH.sub.2OCH.sub.3 339 NO.sub.2 CF.sub.3 H —CH.sub.2CO—OCH.sub.3 340 NO.sub.2 CF.sub.3 H —CH.sub.2CH.sub.2CO—OCH.sub.3 341 NO.sub.2 H m-NO.sub.2 —CH.sub.3 342 NO.sub.2 H m-NO.sub.2 —C.sub.2H.sub.5 343 NO.sub.2 H m-NO.sub.2 n-C.sub.3H.sub.7 344 NO.sub.2 H m-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 345 NO.sub.2 H m-NO.sub.2 —CH.sub.2CO—OCH.sub.3 346 NO.sub.2 H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 347 NO.sub.2 H m-CF.sub.3 —CH.sub.3 348 NO.sub.2 H m-CF.sub.3 —C.sub.2H.sub.5 349 NO.sub.2 H m-CF.sub.3 n-C.sub.3H.sub.7 350 NO.sub.2 H m-CF.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 351 NO.sub.2 H m-CF.sub.3 —CH.sub.2CO—OCH.sub.3 352 NO.sub.2 H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 353 NO.sub.2 H p-OCH.sub.3 —CH.sub.3 354 NO.sub.2 H p-OCH.sub.3 —C.sub.2H.sub.5 355 NO.sub.2 H p-OCH.sub.3 n-C.sub.3H.sub.7 356 NO.sub.2 H p-OCH.sub.3 —CH.sub.2CH.sub.2COH.sub.3 357 NO.sub.2 H p-OCH.sub.3 —CH.sub.2CO—OCH.sub.3 358 NO.sub.2 H p-OCH.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 359 NO.sub.2 H p-CN —CH.sub.3 360 NO.sub.2 H p-CN —C.sub.2H.sub.5 361 NO.sub.2 H p-CN n-C.sub.3H.sub.7 362 NO.sub.2 H p-CN —CH.sub.2CH.sub.2COH.sub.3 363 NO.sub.2 H p-CN —CH.sub.2CO—OCH.sub.3 364 NO.sub.2 H p-CN —CH.sub.2CH.sub.2CO—OCH.sub.3 365 NO.sub.2 H p-Cl —CH.sub.3 366 NO.sub.2 H p-Cl —C.sub.2H.sub.5 367 NO.sub.2 H p-Cl n-C.sub.3H.sub.7 368 NO.sub.2 H p-Cl —CH.sub.2CH.sub.2OCH.sub.3 369 NO.sub.2 H p-Cl —CH.sub.2CO—OCH.sub.3 370 NO.sub.2 H p-Cl —CH.sub.2CH.sub.2CO—OCH.sub.3 371 NO.sub.2 H p-Br —CH.sub.3 372 NO.sub.2 H p-Br —C.sub.2H.sub.5 373 NO.sub.2 H p-Br n-C.sub.3H.sub.7 874 NO.sub.2 H p-Br —CH.sub.2CH.sub.2OCH.sub.3 375 NO.sub.2 H p-Br —CH.sub.2CO—OCH.sub.3 376 NO.sub.2 H p-Br —CH.sub.2CH.sub.2CO—OCH.sub.3 377 NO.sub.2 H p-NO.sub.2 —CH.sub.3 378 NO.sub.2 H p-NO.sub.2 —C.sub.2H.sub.5 379 NO.sub.2 H p-NO.sub.2 n-C.sub.3H.sub.7 380 NO.sub.2 H p-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 381 NO.sub.2 H p-NO.sub.2 —CH.sub.2CO—OCH.sub.3 382 NO.sub.2 H p-NO.sub.2 —CH.sub.2CH.sub.2CO—OCH.sub.3 383 NO.sub.2 H H —CH.sub.3 384 NO.sub.2 H H —C.sub.2H.sub.5 540 385 NO.sub.2 H H n-C.sub.3H.sub.7 386 NO.sub.2 H H —CH.sub.2CH.sub.2OCH.sub.3 387 NO.sub.2 H H —CH.sub.2CO—OCH.sub.3 388 NO.sub.2 H H —CH.sub.2CH.sub.2CO—OCH.sub.3 389 CH.sub.3 H m-NO.sub.2 —CH.sub.3 390 CH.sub.3 H m-NO.sub.2 —C.sub.2H.sub.5 391 CH.sub.3 H m-NO.sub.2 n-C.sub.3H.sub.7 392 CH.sub.3 H m-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 393 CH.sub.3 H m-NO.sub.2 —CH.sub.2CO—OCH.sub.3 394 CH.sub.3 H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 395 CH.sub.3 H m-CF.sub.3 —CH.sub.3 396 CH.sub.3 H m-CF.sub.3 —C.sub.2H.sub.5 397 CH.sub.3 H m-CF.sub.3 n-C.sub.3H.sub.7 398 CH.sub.3 H m-CF.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 399 CH.sub.3 H m-CF.sub.3 —CH.sub.2CO—OCH.sub.3 400 CH.sub.3 H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 401 CH.sub.3 H p-OCH.sub.3 —CH.sub.3 402 CH.sub.3 H p-OCH.sub.3 —C.sub.2H.sub.5 403 CH.sub.3 H p-OCH.sub.3 n-C.sub.3H.sub.7 404 CH.sub.3 H p-OCH.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 405 CH.sub.3 H p-OCH.sub.3 —CH.sub.2CO—OCH.sub.3 406 CH.sub.3 H p-OCH.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 407 CH.sub.3 H p-CN —CH.sub.3 408 CH.sub.3 H p-CN —C.sub.2H.sub.5 409 CH.sub.3 H p-CN n-C.sub.3H.sub.7 410 CH.sub.3 H p-CN —CH.sub.2CH.sub.2OCH.sub.3 411 CH.sub.3 H p-CN —CH.sub.2CO—OCH.sub.3 412 CH.sub.3 H p-CN —CH.sub.2CH.sub.2CO—OCH.sub.3 413 CH.sub.3 H p-Cl —CH.sub.3 414 CH.sub.3 H p-Cl —C.sub.2H.sub.5 415 CH.sub.3 H p-Cl n-C.sub.3H.sub.7 416 CH.sub.3 H p-Cl —CH.sub.2CH.sub.2OCH.sub.3 417 CH.sub.3 H p-Cl —CH.sub.2CO—OCH.sub.3 418 CH.sub.3 H p-Cl —CH.sub.2CH.sub.2CO—OCH.sub.3 419 CH.sub.3 H p-Br —CH.sub.3 420 CH.sub.3 H p-Br —C.sub.2H.sub.5 421 CH.sub.3 H p-Br n-C.sub.3H.sub.7 422 CH.sub.3 H p-Br —CH.sub.2CH.sub.2COH.sub.3 423 CH.sub.3 H p-Br —CH.sub.2CO—OCH.sub.3 424 CH.sub.3 H p-Br —CH.sub.2CH.sub.2CO—OCH.sub.3 425 CH.sub.3 H p-NO.sub.2 —CH.sub.3 426 CH.sub.3 H p-NO.sub.2 —C.sub.2H.sub.5 427 CH.sub.3 H p-NO.sub.2 n-C.sub.3H.sub.7 428 CH.sub.3 H p-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 429 CH.sub.3 H p-NO.sub.2 —CH.sub.2CO—OCH.sub.3 430 CH.sub.3 H p-NO.sub.2 —CH.sub.2CH.sub.2CO—OCH.sub.3 430 CH.sub.3 H H —CH.sub.3 432 CH.sub.3 H H —C.sub.2H.sub.5 433 CH.sub.3 H H n-C.sub.3H.sub.7 434 CH.sub.3 H H —CH.sub.2CH.sub.2OCH.sub.3 435 CH.sub.3 H H —CH.sub.2CO—OCH.sub.3 436 CH.sub.3 H H —CH.sub.2CH.sub.2CO—OCH.sub.3 437 OCH.sub.3 H m-NO.sub.2 —CH.sub.3 438 OCH.sub.3 H m-NO.sub.2 —C.sub.2H.sub.5 439 OCH.sub.3 H m-NO.sub.2 n-C.sub.3H.sub.7 440 OCH.sub.3 H m-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 441 OCH.sub.3 H m-NO.sub.2 —CH.sub.2CO—OCH.sub.3 442 OCH.sub.3 H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 443 OCH.sub.3 H m-CF.sub.3 —CH.sub.3 444 OCH.sub.3 H m-CF.sub.3 —C.sub.2H.sub.5 445 OCH.sub.3 H m-CF.sub.3 n-C.sub.3H.sub.7 446 OCH.sub.3 H m-CF.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 447 OCH.sub.3 H m-CF.sub.3 —CH.sub.2CO—OCH.sub.3 448 OCH.sub.3 H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 449 OCH.sub.3 H p-OCH.sub.3 —CH.sub.3 450 OCH.sub.3 H p-OCH.sub.3 —C.sub.2H.sub.5 451 OCH.sub.3 H p-OCH.sub.3 n-C.sub.3H.sub.7 452 OCH.sub.3 H p-OCH.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 453 OCH.sub.3 H p-OCH.sub.3 —CH.sub.2CO—OCH.sub.3 454 OCH.sub.3 H p-OCH.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 455 OCH.sub.3 H p-CN —CH.sub.3 456 OCH.sub.3 H p-CN —C.sub.2H.sub.5 457 OCH.sub.3 H p-CN n-C.sub.3H.sub.7 458 OCH.sub.3 H p-CN —CH.sub.2CH.sub.2COH.sub.3 459 OCH.sub.3 H p-CN —CH.sub.2CO—OCH.sub.3 460 OCH.sub.3 H p-CN —CH.sub.2CH.sub.2CO—OCH.sub.3 461 OCH.sub.3 H p-Cl —CH.sub.3 462 OCH.sub.3 H p-Cl —C.sub.2H.sub.5 463 OCH.sub.3 H p-Cl n-C.sub.3H.sub.7 464 OCH.sub.3 H p-Cl —CH.sub.2CH.sub.2OCH.sub.3 465 OCH.sub.3 H p-Cl —CH.sub.2CO—OCH.sub.3 466 OCH.sub.3 H p-Cl —CH.sub.2CH.sub.2CO—OCH.sub.3 467 OCH.sub.3 H p-Br —CH.sub.3 468 OCH.sub.3 H p-Br —C.sub.2H.sub.5 469 OCH.sub.3 H p-Br n-C.sub.3H.sub.7 470 OCH.sub.3 H p-Br —CH.sub.2CH.sub.2OCH.sub.3 471 OCH.sub.3 H p-Br —CH.sub.2CO—OCH.sub.3 472 OCH.sub.3 H p-Br —CH.sub.2CH.sub.2CO—OCH.sub.3 473 OCH.sub.3 H p-NO.sub.2 —CH.sub.3 474 OCH.sub.3 H p-NO.sub.2 —C.sub.2H.sub.5 475 OCH.sub.3 H p-NO.sub.2 n-C.sub.3H.sub.7 476 OCH.sub.3 H p-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 477 OCH.sub.3 H p-NO.sub.2 —CH.sub.2CO—OCH.sub.3 478 OCH.sub.3 H p-NO.sub.2 —CH.sub.2CH.sub.2CO—OCH.sub.3 479 OCH.sub.3 H H —CH.sub.3 480 OCH.sub.3 H H —C.sub.2H.sub.5 481 OCH.sub.3 H H n-C.sub.3H.sub.7 482 OCH.sub.3 H H —CH.sub.2CH.sub.2OCH.sub.3 483 OCH.sub.3 H H —CH.sub.2CO—OCH.sub.3 484 OCH.sub.3 H H —CH.sub.2CH.sub.2CO—OCH.sub.3 485 CF.sub.3 H m-NO.sub.2 —CH.sub.3 486 CF.sub.3 H m-NO.sub.2 —C.sub.2H.sub.5 487 CF.sub.3 H m-NO.sub.2 n-C.sub.3H.sub.7 488 CF.sub.3 H m-NO.sub.2 —CH.sub.2CH.sub.2COH.sub.3 489 CF.sub.3 H m-NO.sub.2 —CH.sub.2CO—OCH.sub.3 490 CF.sub.3 H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 491 CF.sub.3 H m-CF.sub.3 —CH.sub.3 492 CF.sub.3 H m-CF.sub.3 —C.sub.2H.sub.5 493 CF.sub.3 H m-CF.sub.3 n-C.sub.3H.sub.7 494 CF.sub.3 H m-CF.sub.3 —CH.sub.2CH.sub.2COH.sub.3 495 CF.sub.3 H m-CF.sub.3 —CH.sub.2CO—OCH.sub.3 496 CF.sub.3 H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 497 CF.sub.3 H p-OCH.sub.3 —CH.sub.3 498 CF.sub.3 H p-OCH.sub.3 —C.sub.2H.sub.5 499 CF.sub.3 H p-OCH.sub.3 n-C.sub.3H.sub.7 500 CF.sub.3 H p-OCH.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 501 CF.sub.3 H p-OCH.sub.3 —CH.sub.2CO—OCH.sub.3 502 CF.sub.3 H p-OCH.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 503 CF.sub.3 H p-CN —CH.sub.3 504 CF.sub.3 H p-CN —C.sub.2H.sub.5 505 CF.sub.3 H p-CN n-C.sub.3H.sub.7 506 CF.sub.3 H p-CN —CH.sub.2CH.sub.2OCH.sub.3 507 CF.sub.3 H p-CN —CH.sub.2CO—OCH.sub.3 508 CF.sub.3 H p-CN —CH.sub.2CH.sub.2CO—OCH.sub.3 509 CF.sub.3 H p-Cl —CH.sub.3 510 CF.sub.3 H p-Cl —C.sub.2H.sub.5 511 CF.sub.3 H p-Cl n-C.sub.3H.sub.7 512 CF.sub.3 H p-Cl —CH.sub.2CH.sub.2OCH.sub.3 513 CF.sub.3 H p-Cl —CH.sub.2CO—OCH.sub.3 514 CF.sub.3 H p-Cl —CH.sub.2CH.sub.2CO—OCH.sub.3 515 CF.sub.3 H p-Br —CH.sub.3 516 CF.sub.3 H p-Br —C.sub.2H.sub.5 517 CF.sub.3 H p-Br n-C.sub.3H.sub.7 518 CF.sub.3 H p-Br —CH.sub.2CH.sub.2OCH.sub.3 519 CF.sub.3 H p-Br —CH.sub.2CO—OCH.sub.3 520 CF.sub.3 H p-Br —CH.sub.2CH.sub.2CO—OCH.sub.3 521 CF.sub.3 H p-NO.sub.2 —CH.sub.3 522 CF.sub.3 H p-NO.sub.2 —C.sub.2H.sub.5 523 CF.sub.3 H p-NO.sub.2 n-C.sub.3H.sub.7 524 CF.sub.3 H p-NO.sub.2 —CH.sub.2CH.sub.2COH.sub.3 525 CF.sub.3 H p-NO.sub.2 —CH.sub.2CO—OCH.sub.3 526 CF.sub.3 H p-NO.sub.2 —CH.sub.2CH.sub.2CO—OCH.sub.3 527 CF.sub.3 H H —CH.sub.3 528 CF.sub.3 H H —C.sub.2H.sub.5 532 529 CF.sub.3 H H n-C.sub.3H.sub.7 530 CF.sub.3 H H —CH.sub.2CH.sub.2COH.sub.3 531 CF.sub.3 H H —CH.sub.2CO—OCH.sub.3 532 CF.sub.3 H H —CH.sub.2CH.sub.2CO—OCH.sub.3 533 Br H m-CF.sub.3 —C.sub.2H.sub.5 534 Br H m-CF.sub.3 n-C.sub.3H.sub.7 535 Br H m-CF.sub.3 —CH.sub.2CH.sub.2COH.sub.3 536 Br H m-CF.sub.3 —CH.sub.2CO—OCH.sub.3 537 Br H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 538 Br H p-OCH.sub.3 —CH.sub.3 539 Br H p-OCH.sub.3 —C.sub.2H.sub.5 540 Br H p-OCH.sub.3 n-C.sub.3H.sub.7 541 Br H p-OCH.sub.3 —CH.sub.2CH.sub.2OCH.sub.3 542 Br H p-OCH.sub.3 —CH.sub.2CO—OCH.sub.3 543 Br H p-OCH.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 544 Br H p-CN —CH.sub.3 545 Br H p-CN —C.sub.2H.sub.5 546 Br H p-CN n-C.sub.3H.sub.7 547 Br H p-CN —CH.sub.2CH.sub.2OCH.sub.3 548 Br H p-CN —CH.sub.2CO—OCH.sub.3 549 Br H p-CN —CH.sub.2CH.sub.2CO—OCH.sub.3 550 Br H p-Cl —CH.sub.3 551 Br H p-Cl —C.sub.2H.sub.5 552 Br H p-Cl n-C.sub.3H.sub.7 553 Br H p-Cl —CH.sub.2CH.sub.2OCH.sub.3 554 Br H p-Cl —CH.sub.2CO—OCH.sub.3 555 Br H p-Cl —CH.sub.2CH.sub.2CO—OCH.sub.3 556 Br H p-Br —CH.sub.3 557 Br H p-Br —C.sub.2H.sub.5 558 Br H p-Br n-C.sub.3H.sub.7 559 Br H p-Br —CH.sub.2CH.sub.2OCH.sub.3 560 Br H p-Br —CH.sub.2CO—OCH.sub.3 561 Br H p-Br —CH.sub.2CH.sub.2CO—OCH.sub.3 562 Br H p-NO.sub.2 —CH.sub.3 563 Br H p-NO.sub.2 —C.sub.2H.sub.5 564 Br H p-NO.sub.2 n-C.sub.3H.sub.7 565 Br H p-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 566 Br H p-NO.sub.2 —CH.sub.2CO—OCH.sub.3 567 Br H p-NO.sub.2 —CH.sub.2CH.sub.2CO—OCH.sub.3 568 Br H H —CH.sub.3 569 Br H H —C.sub.2H.sub.5 570 Br H H n-C.sub.3H.sub.7 571 Br H H —CH.sub.2CH.sub.2OCH.sub.3 572 Br H H —CH.sub.2CO—OCH.sub.3 573 Br H H —CH.sub.2CH.sub.2CO—OCH.sub.3 574 Br H m-NO.sub.2 —CH.sub.3 575 Br H m-NO.sub.2 —C.sub.2H.sub.5 576 Br H m-NO.sub.2 n-C.sub.3H.sub.7 577 Br H m-NO.sub.2 —CH.sub.2CH.sub.2OCH.sub.3 578 Br H m-NO.sub.2 —CH.sub.2CO—OCH.sub.3 579 Br H m-CF.sub.3 —CH.sub.2CH.sub.2CO—OCH.sub.3 580 Br H m-CF.sub.3 —CH.sub.3

II. APPLICATION EXAMPLES

(9) II.1: Dyeing of Polyester

(10) 1 part by weight of the dye of formula (101) prepared in Example 1.1 is milled together with four parts of a commercially available dispersing agent and 15 parts of water. Using that formulation, a 1% dyeing (based on the dye and the substrate) is produced on woven polyester by high temperature exhaust process at 135° C.

(11) Test results: the light fastness of the dyeing is excellent as well as the results in the AATCC 61 and ISO 105 tests. The build up properties of the dye are very good.