Bridged anthraquinones

• US 5,912,386 A
• Filed: 02/06/1998
• Issued: 06/15/1999
• Est. Priority Date: 02/13/1997
• Status: Expired due to Fees

• Current Assignee: Lanxess Deutschland GmbH (Lanxess AG)
• Original Assignee: Bayer AG
• Inventors: Blaser, Helmut, Reinhardt, Karl-Heinz, Kalz, Dietmar
• Primary Examiner(s): Burn, Brian M.
• Application Number:
  US09/019,571
• Time in Patent Office: 494 Days
• Field of Search: 564/308, 564/427, 564/452, 564/457, 564/459
• US Class Current: 564/308
• CPC Class Codes: C08K 5/0041 Optical brightening agents, organic pigments
• CPC Class Codes: C09B 1/262 Dyes with no other substituents than the substituted amino groups
• CPC Class Codes: C09B 1/285 Dyes with no other substituents than the amino groups
• CPC Class Codes: C09B 1/42 the acyl groups being residues of an aromatic carboxylic acid

Abstract

The present invention relates to compounds of the formula (I)

R.sup.1 --NH--B--NH--R.sup.2                               (I),

wherein

R¹ and R² independently of one another denote an unsubstituted or substituted radical of the formula ##STR1## and B represents an unsubstituted or substituted cycloalkylene-containing bridge member, which are suitable for bulk dyeing of plastics.

Claims

1. A compound of the formula (I)

View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15)

2. The compound according to claim 1, wherein the radicals R¹ and R² are unsubstituted.

3. The compound according to claim 1, which corresponds to the formula (Ia) ##STR45## wherein B represents an unsubstituted or substituted cycloalkylene-containing bridge member.

4. The compound according to claim 1 corresponding to the formula (Ib) ##STR46## wherein R³ and R⁴ independently of one another represent hydrogen or unsubstituted or substituted alkyl, aryl or aroyl,

rings D₁ and D₂ independently of one another are unsubstituted or substituted with OH, amino or substituted amino, aryloxy, halogen, alkyl, or alkoxy, and

B represents an unsubstituted or substituted cycloalkylene-containing bridge member.

5. The compound according to claim 4, wherein R³ and R⁴ independently of one another denote hydrogen;

C₁ -C₄ -alkyl which is unsubstituted or substituted by halogen and/or phenyl;

or phenyl or benzoyl which are unsubstituted or substituted by halogen, alkyl or acylamino.

6. The compound according to claim 4, wherein rings D₁ and D₂ are unsubstituted.

7. The compound according to claim 4, wherein the radicals R³ and R⁴ independently of one another represent hydrogen, phenyl, 4-methylphenyl, benzoyl or 4-methylbenzoyl.

8. The compound according to claim 1, wherein the cycloalkylene denotes C₅ -C₇ -cycloalkylene.

9. The compound according to claim 1, wherein the cycloalkylene is cyclopentylene or 1,3- or 1,4-cyclohexylene.

10. The compound according to claim 1, wherein the bridge member B corresponds to a radical of the formula (II) ##STR47## wherein q1 and q2 independently of one another represent a number from 0 to 4,

X and Y independently of one another denote alkyl or halogen, where if q1 is greater than or equal to 2, X can in each case assume identical or different meanings, and if q2 is greater than or equal to 3, Y can in each case assume identical or different meanings,

A₁ represents a linear or branched C₁ -C₄ -alkylene radical,

A₂ represents a linear or branched C₁ -C₄ -alkylene radical, and

p denotes 0 or 1.

11. The compound according to claim 1, wherein their bridge member B corresponds to a radical of the formula (II) ##STR48## wherein q1 and q2 independently of one another represent a number from 0 to 4,

X and Y independently of one another denote C₁ -C₄ -alkyl or Cl, Br and F, where if q1 is greater than or equal to 2, X can in each case assume identical or different meanings, and if q2 is greater than or equal to 3, Y can in each case assume identical or different meanings,

A₁ represents ##STR49## A₂ represents ##STR50## wherein m and n independently of one another represent a number from 0 to 4 and

p denotes 0 or 1.

12. The compound according to claim 1, wherein the cycloalkylene radical or radicals in the bridge member B are cyclohexylene radicals which independently of one another are linked in the 1,3- or 1,4-position.

13. The compound according to claim 1, wherein the bridge member B corresponds to

(a) ##STR51## wherein q1 represents a number from 0 to 4 and

X denotes alkyl or halogen, where if q1 is greater than or equal to 2, X can in each case assume identical or different meanings,

(b) ##STR52## wherein q1 and q2 independently of one another represent a number from 0 to 4,

X and Y independently of one another denote alkyl or halogen, where if q1 is greater than or equal to 2, X can in each case assume identical or different meanings, and if q2 is greater than or equal to 2, Y can in each case assume identical or different meanings, and

n represents a number from 0 to 4,

(c) ##STR53## wherein q1 represents a number from 0 to 4,

X denotes alkyl or halogen, where if q1 is greater than or equal to 2, X can in each case assume identical or different meanings, and

n represents a number from 0 to 4,

(d) ##STR54## wherein q1 represents a number from 0 to 4,

X denotes alkyl or halogen, where if q1 is greater than or equal to 2, X can in each case assume identical or different meanings, and

m and n independently of one another represent a number from 0 to 4, or

(e) ##STR55## wherein q1 and q2 independently of one another represent a number from 0 to 4 and

X and Y independently of one another denote alkyl or halogen, where if q1 is greater than or equal to 2, X can in each case assume identical or different meanings, and if q2 is greater than or equal to 2, Y can in each case assume identical or different meanings.

14. The compound according to claim 1, wherein the bridge member B corresponds to

(a) ##STR56## wherein X represents chlorine or methyl and

q1 represents 0 or 1,

(b) ##STR57## wherein X and Y in each case denote methyl,

q1 and q2 independently of one another denote 0 or 1 and

n represents 0 or 1,

(c) ##STR58## wherein X represents methyl,

q1 represents 0, 1, 2 or 3 and

n represents 1,

(d) ##STR59## wherein m and n in each case denote 1,

X denotes methyl and

q1 represents 0 or 1, or

(e) ##STR60## wherein X and Y denote methyl and

q1 and q2 independently of one another represent 0 or 1.

15. The compound according to claim 1, wherein the bridge member B is ##STR61##