Water-insoluble azolystyryl optical brighteners

• US 4,510,311 A
• Filed: 01/14/1983
• Issued: 04/09/1985
• Est. Priority Date: 01/30/1982
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Eckstein, Udo
• Primary Examiner(s): Daus, Donald G.
• Assistant Examiner(s): Shen, Cecilia
• Application Number:
  US06/458,085
• Time in Patent Office: 816 Days
• Field of Search: 542/456, 542/462, 542/463, 542/464, 542/444, 542/442, 548/144, 548/251, 548/254, 548/253, 548/132, 548/131, 548/133, 548/134, 548/135, 544/333, 544/182, 544/183
• US Class Current: 548/132
• CPC Class Codes: C07D 271/07 with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 413/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07F 9/65318 having the two nitrogen atoms in positions 1 and 3

Abstract

The invention relates to compounds of the formula ##STR1## or isomeric mixtures thereof, wherein A represents a quasiaromatic heterocyclic radical,

B represents a radical of the formulae ##STR2## n represents 0, 1, 2 or 3, preferably 0-2, R₁ represents hydrogen, CN, R or acyl,

R₂ represents hydrogen, halogen, --OR, --NHR, --N(R'"'"')₂ or NHCOR,

R'"'"' represents alkyl and

R represents R'"'"', alkenyl, aralkyl, cycloakyl or aryl.

They are valuable optical brighteners and/or laser dyes and some of them are intermediate products for preparing these end products.

Claims

1. A water-insoluble compound of the formula ##STR99## wherein A is an oxazole, imidazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,2,3-, 1,2,4- and 1,3,4-triazole, pyrimidine, 1,3,5-triazine, benzoxazole, benzothiazole, benzimidazole, naphthoxazole, benzo-s-triazole, naphtho-s-triazole, benzo(b)-furan, quinazoline, or quinoxaline radical,

B is ##STR100## n is 1, 2 or 3, R₁ is hydrogen, CN, R, --COR, SO₂ R, COOR, CONHR or CON(R'"'"')₂,

R₂ is hydrogen, chlorine, bromine, --OR, --NHR, --N(R'"'"')₂ or NHCOR,

R'"'"' is alkyl having 1 to 6 carbon atoms and being optionally substituted by hydroxyl, C₁ -C₄ -alkoxy, CN, carboxyl, C₁ -C₄ -alkoxycarbonyl, CONH₂, chlorine or bromine, or trifluoromethyl, and

R is R", alkenyl having 2 to 5 carbon atoms, phenyl --C₁ -C₄ -alkyl, phenyl C₁ -C₄ -alkyl substituted on the phenyl ring by chlorine, methyl and/or methoxy, cyclohexyl optionally substituted by up to three times by methyl and/or chlorine, or phenyl which is optionally substituted by C₁ -C₄ -alkyl, trifluoromethyl, chlorine, bromine, carboxyl, cyano, C₁ -C₄ -alkoxycarbonyl and/or C₁ -C₄ -alkoxy.

2. A compound according to claim 1, wherein B is ##STR101##

3. A compound according to claim 1, wherein B is ##STR102##

4. A compound according to claim 1, wherein n is 1 to 2.

5. A compound according to claim 1, wherein

A is ##STR103## , and B is ##STR104## n=1 and wherein

V₁ is hydrogen,

V₂ is hydrogen,

V₃ is hydrogen, and

V₄ is C₁ -C₆ -alkyl which is optionally substituted by C₁ -C₄ -alkoxy, hydroxyl, chlorine, or cyano;

cyclohexyl optionally substituted by up to three times by methyl and/or chlorine;

or phenyl-C₁ -C₄ -alkyl optionally substituted on the phenyl ring by chlorine, methyl and/or methoxy, or phenyl which is optionally substituted by C₁ -C₄ -alkyl, trifluoromethyl, chlorine, bromine, carboxyl, cyano, C₁ -C₄ -alkoxy carbonyl and/or C₁ -C₄ -alkloxy.

6. A compound according to claim 1, wherein A is benzoxazol-2-yl or benzo-s-triazol-2-yl.

7. A compound according to claim 1, of the formula ##STR105## wherein V₁ is hydrogen, and

V₄ methyl, ethyl, n-propyl, isopropyl or n-butyl.

8. A compound according to claim 1, of the formula ##STR106##