Iodide ion releasing compound, and silver halide...

Details Iodide ion releasing compound, and silver halide... Iodide ion releasing compound, and silver halide...

1998-12-21

2001-05-15

Le, Hoa Van (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Radiation sensitive product

Silver compound sensitizer containing

C430S569000

Reexamination Certificate

active

06232057

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a novel iodide ion releasing compound and a silver halide light-sensitive photographic material employing the same, especially a silver halide light-sensitive photographic material exhibits an excellent property in sensitivity and fog.
BACKGROUND OF THE INVENTION
Recently, along with the increased popularity of picture-taking instruments such as cameras, there increase picture-taking chances by use of a silver halide light sensitive photographic material (hereinafter, referred to as a photographic material). As a result, further enhancement in sensitivity and image quality has been desired by the public.
One domain ant factor for enhancing sensitivity and image quality of the photographic material concerns silver halide grains, and there has been on going development of silver halide grains aimed at enhancement of sensitivity and image quality.
Japanese Patent Publication Open to Public inspection (hereinafter referred to as JP-A) Nos. 5-323487, 6-11781, 6-11782, 6-27567, 6-250309, 6-250310, 6-250311, 6-250313, 6-242527 etc. disclose the realization of enhancement of sensitivity and the improvement of fog-pressure-resistance by using the iodide ion releasing compound in preparing a silver halide grain.
However, since the releasing speed of iodide ion from these well-known iodide ion releasing compounds is slow, there has been limitation in enhancement of sensitivity and it is insufficient with these compounds to meet recent demand in the photographic material and development of more skilled know-how in the photographic material has been desired.
SUMMARY OF THE INVENTION
An object of the present invention is to provide the photographic material achieving enhanced sensitivity and reduced fog using iodide ion releasing compound which can release the iodide ion rapidly.
DETAILED DESCRIPTION OF THE INVENTION
Above object of the invention could be attained by the following method.
(1) An iodide ion releasing compound represented by the following Formula [1],
wherein R
1
, R
2
and R
3
represent a hydrogen atom and substituents; EWG represents —CO
2
—, —OCO—, —SO
2
—, —SO
2
O—, —OSO
2
—, —CONR
4
—, —NR
5
CO—, —CSNR
6
—, —NR
7
CS—, —NR
8
—, —O—, —S—, —CO—, —COCO— and —NR
9
SO
2
—; L represents linking group; SOL represents aqueous soluble group; R
41
R
5
, R
6
, R
7
, R
8
and R
9
represent a hydrogen atom and substituents; n and m represent an integer of 1-4.
(2) The iodide ion releasing compound of item 1, wherein EWG represents —SO
2
—.
(3) A silver halide grain formed using at least one of an iodide ion releasing compound represented by the following Formula [1],
wherein R
1
, R
2
and R
3
represent a hydrogen atom and substituents, EWG represents —CO
2
—, —OCO—, —SO
2
—, —SO
2
O—, —OSO
2
—, —CONR
4
—, —NR
5
CO—, —CSNR
6
—, —NR
7
CS—, —NR
8
—, —O—, —S—, —CO—, —COCO— and —NR
9
SO
2
—, L represents an aromatic group and a heterocyclic group and SOL represents aqueous soluble group; R
4
, R
5
, R
6
, R
7
, R
8
and R
9
represent a hydrogen atom and substituents; n and m represent an integer of 1-4.
(4) The iodide ion releasing compound of item 3, wherein EWG represents —SO
2
—.
(5) A silver halide photographic light-sensitive material containing at least one of the silver halide grain formed using at least one of an iodide ion raleasing compound represented by the following Formula [1],
wherein R
1
, R
2
and R
3
represent a hydrogen atom and substituents, EWG represents —CO
2
—, —OCO—, —SO
2
—, —SO
2
O—, —OSO
2
—, —CONR
4
—, —NR
5
CO—, —CSNR
6
—, —NR
7
CS—, —NR
8
—, —O—, —S—, —CO—, —COCO— and NR
9
SO
2
—, L represents an aromatic group and a heterocyclic group and SOL represents aqueous soluble group; R
4
, R
5
, R
6
, R
7
, R
8
and R
9
represent a hydrogen atom and substituents; n and m represent an integer of 1-4.
(6) The iodide ion releasing compound of item 5, wherein EWG represents —SO
2
—.
Next, the invention will be explained in detail
In the formula [1], R
1
, R
2
and R
3
represent a hydrogen atom and substituents, and as a preferable substituent is cited an alkyl group (for example, a methyl group, an ethyl group and an iso-propyl group), a cyano group, a nitro group, an alkoxy group (for example, a methoxy group And an ethoxy group). R
4
, R
5
, R
6
, R
7
, R
8
and R
9
represent a hydrogen atom and substituents and as a preferable substituent is cited an alkyl group (for example, a methyl group, an ethyl group and an isopropyl group). A linking group represented by L represents an aromatic group and a heterocyclic group, and as an aromatic group is cited a phenyl group and a naphthyl group, and as a heterocyclic group is cited a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring and an oxazole ring. These groups cited above may possess sustitutents. As preferable sustitutents are cited an alkyl group (for example, a methyl group, an ethyl group, an isopropyl group and a cyclohexyl group), a cyano group, a nitro group, an amino group, an alkoxy group (for example, a methoxy group and an ethoxy group) and a halogen atom (for example, a chlorine, a bromine and an iodine atom). An aqueous group represented by SOL concretely represents —OM, —COOM, —SO
3
M, —PO
3
M and a quaternary onium salt and M represents a hydrogen and an alkali metal. The preferable aqueous groups are —COOM and —SO
3
M.
The example of the compound represented by formula [1] in the invention is listed below, but is not limited thereto.
The compound represented by the formula [I] of the invention can be synthesized by a known substitution reaction. For example, are used the reaction methods as shown in the following chemical formulas.
[A]—OH+[B]COCl→base→[A]—OCO—[B]+HCl:  Formula 1
[A]—NH
2
+[B]—COCl→base→[A]—NHCO—[B]+HCl:  Formula 2
[A]—OH+[B]—SO
2
Cl→base→[A]—OSO
2
—[B]+HCl:  Formula 3
[A] represents an aromatic group, and [B] represents an aliphatic group.
The synthetic methods for obtaining the representative compounds are sown below.


REFERENCES:
patent: 5482826 (1996-01-01), Okamura et al.
patent: 5527664 (1996-06-01), Kikuchi et al.
patent: 412699 (1922-07-01), None
patent: 0563701 (1993-10-01), None
patent: 2278333 (1976-02-01), None
Baker, B.R. et al.—“Potential anticancer agents”—Journal of Organic Chemistry, 1962, pp. 3283-3295.
Bergel, et al.—“Aryl-2-halogenoalkylamines”—Journal of the Chemical Society, 1955, pp. 3835-3839.
Cambanis, Gericke—“Aromatische N-LOST-Verbindungen”—Arzneimittel-Forschung, vol. 25, 1975, pp. 1-9.
European Search Report EP 98 12 4290.

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