Reactive dyes containing a halobenzene nucleus

A dye according to any preceding claim, of the formula (VIII)

• Z1-L1-D-(L2)a-Z2 (VIII)
• wherein:
• D is a chromophore;
• each of L1 and L2 is an amine or piperazine linkage of the formula
• —N(R)— (VII)1;
• 359 —N(R)BN(R)— (VII)3
• wherein:
• R, or each R independently, is hydrogen or C1-4 alkyl;
• B is a hydrocarbon bridging group which has at least two carbon atoms, is optionally substituted, optionally includes at least one hetero atom and is optionally a chromophore;
• a is zero or 1;
• and
• b is from 2 to 6 inclusive;
• Z1 is a group
• 360
• in which:
• n is 1 or 2;
• X, or each X independently, is an electron withdrawing group;
• and
• Y is a halogen atom;
• and
• when a is 1, Z2 is:
• a group of the formula (I), given and defined above but selected independently thereof;
• or
• a group of the formula (II)
• 361
• wherein:
• m is 1 or 2;
• p is 0 or 1;
• when m is 1, p is 1;
• and when m is 2, p is 0;
• Y1, or each Y1 independently, is a halogen atom or an optionally substituted pyridinium group;
• and
• T is C1-4 alkoxy, thioalkoxy or N(R1) (R2) in which R1 is hydrogen, optionally substituted C1-4 alkyl or optionally substituted aryl and
• R2 is hydrogen or optionally substituted C1-4 alkyl;
• or
• a group of the formula (III)
• 362
• wherein:
• x is 1, 2 or 3;
• y is zero, 1 or 2;
• and x+y≦3;
• Y2, or each Y2 independently, is a halogen atom;
• and
• U, or each U independently, is C1-4 alkyl or C1-4 alkylsulphonyl;
• and
• when a is zero, Z2 is:
• —SO2CH2CH2X1 (IV)
• in which X1 is an eliminatable group;
• or
• —SO2 (CH2)ZCH═CH2 (V)
• wherein z is zero or 1;
• or
• a group of formula (VI)
• —W—C(R10)═CH2 (VI)
• wherein:
• R10 is hydrogen, C1-4alkyl or halogen;
• and
• W is —OC(═O)— or —N(R11)C(═O)— in which R is hydrogen or C1-4 alkyl.

A process for preparing a dye of the formula (VIII)1

• Z1-L1-D-L2-Z2 (VIII)1
• wherein:
• D is a chromophore;
• each of L1 and L2 independently, is N(R);
• each R, independently, is hydrogen or C1-4alkyl;
• each of Z1 and Z2 is a group
• 382
• in which:
• n is 1 or 2
• X, or each X independently, is an electron withdrawing group;
• and
• Y is a halogen atom, which process comprises reacting a chromophoric compound of the formula (XX)
• H(R)N-D-N(R)H (XX)
• wherein each of D and R is as defined above, with at least two moles, per mole of the chromophoric compound of the formula (XX), of a dihalobenzene component comprising at least one dihalobenzene compound of the formula (XXI)
• 383
• wherein each of X, Y and n is as defined above, to obtain the dye of the formula (VIII)1.

A process for preparing a dye of the formula (VIII)3

• Z1-L1-D-Z2 (VIII)3
• wherein:
• D is a chromophore
• L1 is N(R), in which R is hydrogen or C1-4alkyl;
• Z1 is a group
• 387
• in which n is 1 or 2;
• X, or each X independently, is an electron withdrawing group;
• and Y is a hydrogen atom;
• and Z2 is a group of the formula (IV) —SO2CH2CH2X1 (IV)
• —SO2CH2CH2X1 (IV)
• wherein X1 is an eliminatable group;
• a group of the formula (V)
• —SO2(CH2)ZCH═CH2 (V)
• wherein z is zero or 1;
• and
• a group of formula (VI)
• —W—C(R10)═CH2 (VI)
• wherein:
• R10 is hydrogen, C1-4alkyl or halogen;
• and
• W is —OC(═O)— or —N(R11)C(═O)—
• in which R11 is hydrogen or C1-4alkyl;
• which process comprises reacting a chromophoric compound of the formula (XXIV)
• H(R)N-D-Z2 (XXIV)
• wherein D and Z2 are as defined above, with a dihalobenzene compound of the formula (XXI)
• 388
• wherein each of X, Y and n is as defined above, to obtain the dye of the formula (VIII)3.