# US 5,330,884 A · Photographic element with near-infrared antihalation layer

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- Number: US 5,330,884 A
- Document ID: US5330884A
- Status: Granted
- Kind: A
- Application number: 08/072,852
- Filed: 1993-05-26
- Granted: 1994-07-19
- Earliest claimed: 1993-05-26
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: Dietrich M. Fabricius; Thomas Schelhorn
- Web page: https://patentgrep.com/patent/US5330884A

## CPC

- G03C 1/832: {Methine or polymethine dyes}
- C09B 23/0066: {the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)}
- G03C 1/127: {the polymethine chain forming part of a carbocyclic ring}
- G03C 5/16: X-ray, infrared, or ultraviolet ray processes
- G03C 2200/39: Laser exposure
- G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

Disclosed is a photographic element comprising an antihalation dye of formula: ##STR1## wherein X.sup.1, X.sup.2 independently represents --CR.sup.8 R.sup.9 --, --S--, --Se--, --NR.sup.10 --, --CH.dbd.CH-- or --O--; n is an integer of 2 or 3; R.sup.1 and R.sup.2 independently represent alkyl of 1 to 10 carbons or substituted alkyl of 1 to 10 carbons; R.sup.3 represents a ring chosen from the set consisting of aryl, substituted aryl, and a heterocyclic ring; R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently represent hydrogen, alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, R.sup.4 and R.sup.5 taken together or R.sup.6 and R.sup.7 taken together may represent the atoms necessary to form a 5 or 6-membered aliphatic ring, an aromatic six-membered ring, an aromatic 10-membered ring, a substituted aromatic six-member ring or a substituted aromatic 10-member ring; R.sup.8, R.sup.9 independently represent alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, substituted aryl of 6-10 carbons; R.sup.10 represents an alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, substituted aryl of 6-10 carbons.

## Claims

### Claim 1

A photographic element comprising an absorbing amount of the antihalation dye:
wherein
X.sup.1, X.sup.2 independently represents --CR.sup.8 R.sup.9 --, --S--, --Se--, --NR.sup.10 --, --CH.dbd.CH-- or --O--;
n is an integer of 2 or 3;
R.sup.1 and R.sup.2 independently represent alkyl of 1 to 10 carbons or substituted alkyl of 1 to 10 carbons;
R.sup.3 represents a ring chosen from the set consisting of aryl, substituted aryl, and a heterocyclic ring;
R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently represent hydrogen, alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, R.sup.4 and R.sup.5 taken together or R.sup.6 and R.sup.7 taken together may represent the atoms necessary to form a 5 or 6-membered aliphatic ring, an aromatic six-membered ring, an aromatic 10-membered ring, a substituted aromatic six-member ring or a substituted aromatic 10-member ring;
R.sup.8, R.sup.9 independently represent alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, substituted aryl of 6-10 carbons;
R.sup.10 represents an alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, substituted aryl of 6-10 carbons.

### Claim 2 (depends on 1)

The photographic element recited in claim 1 wherein R.sup.3 is CR.sup.8 R.sup.9 ; R.sup.8 and R.sup.9 independently represent alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, substituted aryl of 6-10 carbons.

### Claim 3 (depends on 1)

The photographic element recited in claim 1 wherein at least one of R.sup.1 and R.sup.2 is an alkyl of 1 to 10 carbon atoms substituted with sulfonate or carbonate.

### Claim 4 (depends on 1)

The photographic element recited in claim 1 wherein R.sup.4 and R.sup.5 or R.sup.6 and R.sup.7 are taken together to form a six-membered aromatic ring or a 10-membered aromatic ring.

### Claim 5 (depends on 4)

The photographic element recited in claim 4 wherein said six-membered aromatic ring or said 10-membered aromatic ring is substituted with sulfonate or carboxylate.

### Claim 6 (depends on 1)

The photographic element recited in claim 1 wherein R.sup.1 or R.sup.2 is an alkyl of 1-10 carbon atoms substituted with a sulfonate or carboxylate and at least one combination of R.sup.4 and R.sup.5 or R.sup.6 and R.sup.7 are taken together to form a six-membered aromatic ring or a 10-membered aromatic ring wherein said six-membered aromatic ring or said 10-membered aromatic ring is substituted with a sulfonate or a carboxylate.

### Claim 7 (depends on 6)

The photographic element recited in claim 6 wherein said R.sup.1 or R.sup.2 is an alkyl of 1-5 carbons atoms.

### Claim 8 (depends on 1)

The photographic element recited in claim 1 wherein said R.sup.3 is chosen from the set consisting of pyrimidine, benzoxazole, phenyltetrazole, and methyl triazole.

### Claim 9

A photographic element comprising a dye of formula: ##STR13## wherein X.sup.1, X.sup.2 independently represents --CR.sup.8 R.sup.9 --, --S--, --Se--, --NR.sup.10 --, --CH.dbd.CH-- or --O--;
n is 2;
R.sup.1 and R.sup.2 independently represent alkyl of 1 to 10 carbons or substituted alkyl of 1 to 10 carbons;
R.sup.3 represents a ring chosen from the set consisting of aryl, substituted aryl, and a heterocyclic ring;
R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently represent hydrogen, alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, R.sup.4 and R.sup.5 taken together or R.sup.6 and R.sup.7 taken together may represent the atoms necessary to form a 5 or 6-membered aliphatic ring, an aromatic six-membered ring, an aromatic 10-membered ring, a substituted aromatic six-member ring or a substituted aromatic 10-member ring;
R.sup.8, R.sup.9 independently represent alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, substituted aryl of 6-10 carbons;
R.sup.10 represents an alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, substituted aryl of 6-10 carbons.

### Claim 10

A photographic element comprising a dye of formula: ##STR14## wherein X.sup.1, X.sup.2 independently represents --CR.sup.8 R.sup.9 --, --S--, --Se--, --NR.sup.10 --, --CH.dbd.CH-- or --O--;
n is 3;
R.sup.1 and R.sup.2 independently represent alkyl of 1 to 10 carbons or substituted alkyl of 1 to 10 carbons;
R.sup.3 represents a ring chosen from the set consisting of aryl, substituted aryl, and a heterocyclic ring;
R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently represent hydrogen, alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, R.sup.4 and R.sup.5 taken together or R.sup.6 and R.sup.7 taken together may represent the atoms necessary to form a 5 or 6-membered aliphatic ring, an aromatic six-membered ring, an aromatic 10-membered ring, a substituted aromatic six-member ring or a substituted aromatic 10-member ring;
R.sup.8, R.sup.9 independently represent alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, substituted aryl of 6-10 carbons;
R.sup.10 represents an alkyl of 1-10 carbons, substituted alkyl of 1-10 carbons, aryl of 6-10 carbons, substituted aryl of 6-10 carbons.