Benzofuran dyes containing a coumarin nucleus

• US 4,973,694 A
• Filed: 08/17/1989
• Issued: 11/27/1990
• 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): Lee, Mary C.
• Assistant Examiner(s): Dentz, B.
• Application Number:
  US07/394,905
• Time in Patent Office: 467 Days
• Field of Search: 549/287, 549/285, 546/66, 546/89, 546/196, 544/151, 548/421, 548/430
• 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 bathocromically shifted absorption peaks.

Claims

1. A dye which satisfies the formula:

##STR34## where 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;

W¹ represents ##STR35## and R¹³ represents a 3-coumarinyl group;

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 the 3-coumarinyl group satisfies the formula:

##STR36## where R⁶ and R⁷ each independently represent hydrogen, alkyl, or aryl;

R⁸ and R⁹ each independently represent alkyl;

or

at least one of the substituent pairs represented by R⁶ and R⁹, R⁷ and R⁸, and R⁸ and R⁹ complete a 5- or 6-membered ring containing the formula nitrogen atom as the sole heteroatom;

alkyl in each occurrence containing from 1 to 8 carbon atoms and aryl in each occurrence being phenyl or naphthyl.

3. A dye according to claim 6 in which R⁶, R⁷, R⁸, and R⁹ complete a julolidine ring structure.

4. A 7-(N,N-dialkylamino)-3-{3-[6-(N,N-dialkylamino)benzo[b]furanyl]acryloyl}coumarin.

5. 9-[3-(2,3,6,7-Tetrahydro-1H,5H-benzo-[i,j]furano[3,2-g]quinolinizin-9-yl)acryloyl]-1,2,4,5-tetrahydro-3H,6H,10H[1]benzopyrano[9,9a,1-gh]quinolazin-10-one.