Novel benzofuran dyes

• US 4,900,831 A
• Filed: 05/09/1988
• Issued: 02/13/1990
• Est. Priority Date: 05/09/1988
• Status: Expired due to Fees

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Fox, John L., Chen, Chin H.
• Primary Examiner(s): Shah, Mukund J.
• Assistant Examiner(s): Rozycki, Andrew G.
• Application Number:
  US07/191,948
• Time in Patent Office: 645 Days
• Field of Search: 546/66
• US Class Current: 546/66
• CPC Class Codes: C09B 23/04 one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
• CPC Class Codes: C09B 23/06 three >CH- groups, e.g. carbocyanines
• CPC Class Codes: C09B 23/105 two >CH- groups
• CPC Class Codes: G03F 7/031 Organic compounds not covered by group G03F7/029

Abstract

A 6-tertiary amino-2-(Z═CH--)benzofuran dye is disclosed, where Z represents the atoms providing an electron withdrawing group and a conjugated methine linkage completing a resonant dye chromophore including the 6-tertiary amino group as an electron donor and the electron withdrawing group as an electron acceptor. The dyes are formed by condensing a 6-tertiary amino-2-formylbenzofuran with an electron withdrawing dye nucleus precursor containing an active methyl or methylene site. The dyes exhibit bathochromically shifted absorption peaks.

Claims

1. A dye which satisfies the formula:

##STR33## where E¹ and E² are independently selected to satisfy the formula;

##STR34## R¹, R², and R⁵ each independently represent hydrogen, alkyl, or aryl;

R³ and R⁴ each independently represent alkyl;

or

at least one of the substituent pairs represented by R¹ and R⁴, R² and R³, and R³ and R⁴ complete a 5- or 6-membered ring containing the formula nitrogen atom as the sole heteroatom;

with the proviso that at least one of E₁ or E₂ are such that R₁ -R₄ complete a julolidine ring structure;

X¹ and X² are independently hydrogen, alkyl, or aryl or together complete a 5 to 7 membered ring and satisfy the formula;

##STR35## where n is 2 to 4;

Y is --NR¹⁰ -- or --O--; and

R¹⁰ is lower alkyl of from 1 to 3 carbon atoms or phenyl;

alkyl, with the exception of said lower alkyl, in each occurrence containing from 1 to 8 carbon atoms and aryl in each occurrence being phenyl or naphthyl.

2. A dye according to claim 1 in which X¹ and X² together complete a ring satisfying the formula:

space="preserve" listing-type="equation">--(CH.sub.2).sub.n --

or

space="preserve" listing-type="equation">--(CH.sub.2 --Y--CH.sub.2)--

where

n is 2 to 4;

Y is --NR¹⁰ -- or --O--; and

R¹⁰ is lower alkyl or phenyl.

3. A dye according to claim 1 in which X¹ and X² together complete a cyclopentanone ring.

4. A dye according to claim 1 in which R¹, R², R³, and R⁴ complete a julolidine ring structure.

6. A dye according to claim 1 in which alkyl in each occurrence contains from 1 to 3 carbon atoms and aryl in each occurrence is phenyl.

5. 2,5-Bis(2,3,6,7-tetrahydro-1H,5H-benzo-[i,j]furano[3,2-g]quinolizin-9-yl-methylene)cyclopentanone.