# US 5,705,323 A · Heat bleachable antihalation composition, elements containing same and method of use

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- Number: US 5,705,323 A
- Document ID: US5705323A
- Status: Granted
- Kind: A
- Application number: 08/583,395
- Filed: 1996-01-05
- Granted: 1998-01-06
- Earliest claimed: 1996-01-05
- Assignees: Eastman Kodak Company
- Inventors: Robert James Perry; Ramanuj Goswami; Paul Anthony Zielinski
- Web page: https://patentgrep.com/patent/US5705323A

## CPC

- G03C 1/83: Organic dyestuffs therefor {(polymeric dyes G03C1/835)}
- 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)

## Abstract

Heat bleachable antihalation compositions are prepared using metallized or unmetallized formazan dyes, hexaarylbiimidzoles having alkoxy substituents and organic carboxylic acids. These compositions are rapidly bleached at relatively low temperatures and can be used in photothermographic elements.

## Claims

### Claim 1

A colored, heat bleachable antihalation composition comprising:
(a) a formazan dye that absorbs at from 400 to 850 nm, and
(b) at least one hexaarylbiimidazole that consists essentially of an oxidative arylimidazole dimer of a compound represented by either structure Ia or Ib: ##STR9## wherein R and R' are independently hydrogen, an alkyl group of 1 to 12 carbon atoms, an alkoxy group of 1 to 8 carbon atoms, amino, a cycloalkyl group having 5 to 7 carbon atoms in the ring, or an electron-rich heterocyclic group having 5 to 7 atoms in the ring, m and n are independently integers of 0 to 5, provided that at least one of R and R' is said alkoxy group, X and X' are independently oxy or imino, Z is alkylene of 1 or 2 carbon atoms, and R.sup.1 and R.sup.2 are independently defined the same as R and R' except that neither R.sup.1 nor R.sup.2 is hydrogen,
said antihalation composition being bleachable when subjected to a temperature of from about 80.degree. to about 150.degree. C. for from about 1 to about 60 seconds.

### Claim 2 (depends on 1)

The composition of claim 1 wherein the molar ratio of said hexaarylbiimidazole to said metallized formazan dye is from 1:1 to 5:1.

### Claim 3 (depends on 1)

The composition of claim 1 wherein said formazan dye is present in a metallized formazan dye complex comprising said dye and a metal that has a log (K) with said dye of .ltoreq.25, and said composition further comprises a carboxylic acid present at a molar ratio to the metal in said metallized formazan dye complex of from 1:1 to 20:1.

### Claim 4 (depends on 1)

The composition of claim 1 wherein said formazan dye has the structure II: ##STR10## wherein R.sup.3 is an aromatic group of 6 to 20 atoms in the ring, R.sup.4 is an aryl group having 6 to 14 carbon atoms in the ring system, and R.sup.5 is an alkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 14 carbon atoms in the ring system, or a heterocyclic ring having 5 to 7 atoms in the ring.

### Claim 5 (depends on 4)

The composition of claim 4 wherein R.sup.3 is a coordinating aromatic group having 5 to 15 atoms in the ring system, and said formazan dye is complexed with a cobalt, zinc, cadmium or copper.

### Claim 6 (depends on 1)

The composition of claim 1 wherein at least one of R and R' is alkoxy of 1 to 8 carbon atoms.

### Claim 7 (depends on 6)

The composition of claim 6 wherein R is alkoxy of 1 to 6 carbon atoms.

### Claim 8 (depends on 1)

The composition of claim 1 wherein R.sup.1 and R.sub.2 are independently a substituted or unsubstituted alkyl group of 1 to 4 carbon atoms or an alkoxy group of 1 to 4 carbon atoms, m and n are each 0 or 1, at least one of X and X' is oxy, and Z is methylene.

### Claim 9 (depends on 3)

The composition of claim 3 wherein said carboxylic acid is p-propoxybenzoic acid, o-, p- or m-anisic acid, palmitic acid, 2-chlorobenzoic acid, 1-naphthoic acid or 4-propylbenzoic acid.

### Claim 10 (depends on 1)

The composition of claim 1 further comprising a film-forming, organic solvent soluble binder material.

### Claim 11 (depends on 10)

The composition of claim 10 wherein said binder material is a polystyrene, polyacrylate or polymethacrylate, a polycarbonate, cellulose ester, polysulfonamide, polyvinyl or polyvinylidene halide, polyvinyl acetate, maleic anhydride ester copolymer, an acrylonitrile-vinylidene chloride copolymer, polyvinyl acetal, an ethylene-vinyl acetate copolymer, butadiene-styrene copolymer, or a polyester.

### Claim 12 (depends on 1)

The composition of claim 1 that is bleachable when subjected to a temperature of from 100.degree. to 150.degree. C. for a time of up to 30 seconds.

### Claim 13 (depends on 5)

The composition of claim 5 wherein said complex metal is zinc, R is alkoxy of 1 to 4 carbon atoms, R' is hydrogen, m and n are each 0, R.sup.3 is p-nitrophenyl, R.sup.4 is benzthiazole, and R.sup.5 is p-methoxyphenyl, and
said composition further comprises poly(vinyl butyral) as a binder material, and an organic carboxylic which is o-anisic acid.

### Claim 14

A photothermographic element comprising a support having thereon a photothermographic layer, and further comprising, on or in said support, an antihalation composition comprising:
(a) a formazan dye that absorbs at from about 400 to about 850 nm, and
(b) at least one hexaarylbiimidazole that consists essentially of an oxidative arylimidazole dimer of a compound represented by either structure Ia or Ib: ##STR11## wherein R and R' are independently hydrogen, an alkyl group of 1 to 12 carbon atoms, an alkoxy group of 1 to 8 carbon atoms, amino, a cycloalkyl group having 5 to 7 carbon atoms in the ring, or an electron-rich heterocyclic group having 5 to 7 atoms in the ring, m and n are independently integers of 0 to 5, provided that at least one of R and R' is said alkoxy group, X and X' are independently oxy or imino, Z is alkylene of 1 or 2 carbon atoms, and R.sup.1 and R.sup.2 are independently defined the same as R and R' except that neither R.sup.1 nor R.sup.2 is hydrogen,
said antihalation composition being bleachable when subjected to a temperature of from 80.degree. to 150.degree. C. for from 1 to 60 seconds.

### Claim 15 (depends on 14)

The element of claim 14 wherein said antihalation composition is in said support.

### Claim 16 (depends on 14)

The element of claim 14 wherein said antihalation composition is formed as a layer on said support, opposite said photothermographic layer.

### Claim 17 (depends on 14)

The element of claim 14 wherein said antihalation composition is formed as a layer on said support, on the same side as said photothermographic layer.

### Claim 18 (depends on 14)

The element of claim 14 wherein said photothermographic layer is a silver halide or silver behenate imaging layer.

### Claim 19 (depends on 14)

The element of claim 14 wherein said formazan dye is present in a metallized formazan dye complex comprising a metal that has a log (K) with said dye of .ltoreq.25.

### Claim 20 (depends on 19)

The element of claim 19 wherein said metal is zinc.

### Claim 21 (depends on 19)

The element of claim 19 wherein said antihalation composition further comprises at least one carboxylic acid having a pKa of from 3 to 6.

### Claim 22

A method for providing an image comprising subjecting an imagewise exposed photothermographic element to heat at from about 80.degree. to 150.degree. C. for from 1 to about 60 seconds,
said element comprising a support having thereon a photothermographic layer, and further comprising on or in said support, an antihalation composition comprising:
(a) a metallized formazan dye complex that absorbs at from 500 to 850 nm, said complex comprising a formazan dye and a metal that has a log (K) with said dye of less than or equal to about 25,
(b) at least one hexaarylbiimidazole that consists essentially of an oxidative arylimidazole dimer of a compound represented by either structure Ia or Ib: ##STR12## wherein R and R' are independently hydrogen, an alkyl group of 1 to 12 carbon atoms, an alkoxy group of 1 to 8 carbon atoms, amino, a cycloalkyl group having 5 to 7 carbon atoms in the ring, or an electron-rich heterocyclic group having 5 to 7 atoms in the ring, and m and n are independently integers of 0 to 5, provided that at least one of R and R' is said alkoxy group, X and X' are independently oxy or imino, Z is alkylene of 1 or 2 carbon atoms, and R.sup.1 and R.sup.2 are independently defined the same as for R and R' except that neither R.sup.1 and R.sup.2 is hydrogen, and
(c) at least one organic carboxylic acid having a pKa of from 3 to 6,
said antihalation composition being bleachable when subjected to said heating conditions.

### Claim 23 (depends on 22)

The method of claim 22 wherein said element is heated at from 100.degree. to about 150.degree. C. for up to 30 seconds.

### Claim 24 (depends on 22)

The method of claim 22 wherein said element is heated at from 110.degree. to 140.degree. C. for from 1 to about 15 seconds.