Core-extended perylene bisimides

• US 6,491,749 B1
• Filed: 03/20/2001
• Issued: 12/10/2002
• Est. Priority Date: 10/21/1998
• Status: Expired due to Fees

• Current Assignee: CIBA Specialty Chemicals
• Original Assignee: CIBA Specialty Chemicals
• Inventors: Speckbacher, Markus, Blanke, Patrick, Kirner, Susanne, Langhals, Heinz
• Primary Examiner(s): AULAKH, CHARANJIT
• Application Number:
  US09/787,592
• Time in Patent Office: 630 Days
• Field of Search: 546/28, 546/31, 544/233, 544/245, 430/78, 106/23.R, 106/287.21, 106/400
• US Class Current: 106/287.21
• CPC Class Codes: C07D 471/06 Peri-condensed systems
• CPC Class Codes: C09B 5/62 Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
• CPC Class Codes: C09D 11/50 Sympathetic, colour changing or similar inks
• CPC Class Codes: C09D 7/41 Organic pigments; Organic dyes
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: G03G 5/0657 containing seven relevant rings
• CPC Class Codes: G03G 5/0659 containing more than seven relevant rings

Abstract

The present inventions relates to nucleus-extended perylenebisimides of formula (I)

intermediates in the preparation of compounds (I) and processes for the preparation of those intermediates and also processes for the preparation of compounds, (I), and the use thereof as colorants.

Claims

1. A nucleus-extended perylenebisimide of general formula (I)

wherein

R¹ and R² are each independently of the other secondary alkyl radical of the formula 1-(C₁-C₉alkyl)-C₂-C₁₀alkyl, C₁-C₂₄cycloalkyl, or C₆-C₁₀aryl, and

A¹ is —

S—

, —

S—

S—

, -CH═

CH—

, R³OOC—

C(—

)═

C(—

)—

COOR³, —

N═

N—

or —

N(R⁴)—

, or a linkage selected from the group consisting of the organic radicals of formulae (III), (IV), (V), (VI) and (VII)

 

wherein

R³ is hydrogen, C₁-C₂₄ alkyl or C₁-C₂₄cycloalkyl, and

R⁴ is unsubstituted or substituted C₁-C₂₄alkyl, C₁-C₂₄cycloalkyl, phenyl, benzyl, -CO-C₁-C₄alkyl, -CO-C₆H₅ or C₁-C₄alkylcarboxylic acid (C₁-C₄alkyl) ester.

with the proviso that when Al is —

s—

, then either R₁ or R₂ is not a phenyl group.

2. A process for the preparation of perylenebisimides (I) according to claim 1, wherein A¹ is A⁴, wherein A⁴ is a linkage selected from the group consisting of the organic radicals of formulae (III), (IV), (V), (VII) and —

N═

N—

, by Diels-Alder reaction of a diene with a dienophile at elevated temperaure, wherein therein there are reacted, as diene, a perylenebisimide of formula (XXI)

and, as dienophile, a compound selected from the group consisting of the compounds of formulae (XXII), (XXIII) and (XXIV)

3. A method for coloring high molecular weight organic material comprising incorporating at least one perylene according claim 1 into said high molecular organic material, wherein said high molecular weight organic material is a polymeric material.

4. A method according to claim 3 wherein the high molecular weight organic material is selected from the group consisting of polyvinyl chloride, cellulose acetate, polycarbonate, polyamide, polyurethane, polyimide, polybenzimidazole, melamine resin, silicone, polyester, polyether, polystyrene, polymethyl methacrylate, polyethylene, polypropylene, polyvinyl acetate, polyacrylonitrile, polybutadiene, polychlorobutadiene, polyisoprene, and copolymers and mixtures thereof.

5. A method for preparing a dye composition comprising incorporating at least one perylene according claim 1 into a homogenous solution suitable for use as a dye.

6. A method for preparing a coating composition comprising incorporating at least one perylene according to claim 1 into a homogenous solution suitable for use as a coating for a substrate.

7. A method according to claim 5, wherein the coating composition is selected from the group consisting of a paint product, lacquer, paper dyes or printing ink.