# US 5,350,666 A · Silver halide photographic materials

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- Number: US 5,350,666 A
- Document ID: US5350666A
- Status: Granted
- Kind: A
- Application number: 07/721,006
- Filed: 1991-06-26
- Granted: 1994-09-27
- Earliest claimed: 1990-06-28
- Assignees: Fuji Photo Film Co., Ltd.
- Inventors: Masuji Motoki; Atsuhiro Ohkawa; Keiji Mihayashi
- Web page: https://patentgrep.com/patent/US5350666A

## CPC

- G03C 7/30576: {characterised by the linking group between the releasing and the released groups, e.g. time-groups}
- Y10S 430/158: Development inhibitor releaser, DIR
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A silver halide photographic material having on a support, at least one photosensitive silver halide emulsion layer, which contains a coupler which releases at least two groups selected from the group consisting of a photographically useful group and a precursor thereof via a timing group upon undergoing a coupling reaction with an oxidized product of a developing agent, in which a plurality of photographically useful groups or precursors thereof are present on different atoms of the timing group, provided that when the plurality of photographically useful groups have a different function to each other, the timing group is not a group utilizing an intramolecular nucleophilic substitution reaction.

## Claims

### Claim 1

A silver halide photographic material comprising on a support, at least one photosensitive silver halide emulsion layer, which contains a coupler represented by formula (I) which releases a plurality of development inhibitors, each development inhibitor being represented by PUG, which are attached, either directly or through a timing group L.sub.1, to different atoms of a timing group L.sub.2 : ##STR40## wherein A represents a coupler residual group, the timing group L.sub.1 represents a divalent timing group, the timing group L.sub.2 has a valence of 3 or more, and PUG represents one of formulae (INH-1) to (INH-8) and (INH-10) to (INH-13), l and n each represents 0, 1 or 2, m represents 1 or 2, and s represents a number obtained by subtracting 1 from the valence of L.sub.2, being an integer of at least 2: ##STR41## wherein R.sub.21 represents a hydrogen atom or a substituted or unsubstituted hydrocarbyl group, * indicates the position at which the group represented by L.sub.1 and L.sub.2 of the compound represented by general formula (I) is bonded, and ** indicated a position at which a substituent group is bonded.

### Claim 2 (depends on 1)

A silver halide photographic material as in claim 1, wherein at least one timing group is of the electron transfer type.

### Claim 3 (depends on 1)

A silver halide photographic material as in claim 1, wherein at least one timing group is of the azole type.

### Claim 4 (depends on 1)

A silver halide photographic material as in claim 1, wherein A represents a coupling group represented by the following general formulae (Cp-1), (Cp-2), (Cp-3), (Cp-4), (Cp-5), (Cp-6), (Cp-7), (Cp-8), (Cp-9) or (Cp-10): ##STR42## Wherein R.sub.41 represents an aliphatic group, an aromatic group or a heterocyclic group; R.sub.42 represents an aromatic group or a heterocyclic group; and R.sub.43, R.sub.44 and R.sub.45 each represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group;
R.sub.51 represents a group as defined for R.sub.41 ;
R.sub.52 and R.sub.53 each represents a group as defined for R.sub.42 ;
b represents an integer of 0 or 1;
R.sub.54 represents a group as defined for R.sub.41, an ##STR43## group, an R.sub.41 S-- group, an R.sub.43 O-- group, an ##STR44## .multidot.group, or an N.tbd.C group; R.sub.55 represents a group as defined for R.sub.41 ;
R.sub.56 and R.sub.57 each represents a group as defined for R.sub.43, an R.sub.41 S-- group, an R.sub.43 O-- group, an ##STR45## group; R.sub.58 represents a group as defined for R.sub.41 ;
R.sub.59 represents a group as defined for R.sub.41, an ##STR46## group, R.sub.41 O-- group, an R.sub.41 S-- group, a halogen atom or an ##STR47## group; d represents an integer from 0 to 3, and when d represents 2 or more, the two or more R.sub.59 's may be the same or different, or each of the two R.sub.59 's may be a divalent group and connected with each other to form a ring structure;
R.sub.60 represents a group as defined for R.sub.41 ;
R.sub.61 represents a group as defined for R.sub.41 ;
R.sub.62 represents a group as defined for R.sub.41, an R.sub.41 OCONH-- group, an R.sub.41 SONH-- group, an ##STR48## group, an R.sub.43 O-- group, an R.sub.41 S-- group, a halogen atom or an ##STR49## group; R.sub.63 represents a group as defined for R.sub.41, an ##STR50## group, an R.sub.41 SO.sub.2 -- group, an R.sub.43 OCO-- group, an R.sub.43 OSO.sub.2 -- group, a halogen atom, a nitro group, a cyano group or an R.sub.43 CO-- group; and
e represents an integer from 0 to 4, and when e is 2 or more, the two or more R.sub.62 's or R.sub.63 's may be the same or different.

### Claim 5 (depends on 1)

A silver halide photographic material as in claim 1, wherein L.sub.1 is represented by the following general formulae (T-1), (T-2), (T-3), (T-4), (T-5), or (T-6): ##STR51## wherein * indicates the position at which A, L.sub.1 or L.sub.2 of the compound represented by general formula (I) is bonded, and ** indicates the position at which L.sub.1, L.sub.2 or PUG are bonded; W represents an oxygen atom, a sulfur atom or an ##STR52## group, R.sub.11 and R.sub.12 each represents a hydrogen atom or substituent group, R.sub.13 represents a substituent group and t represents 1 or 2, and when t is 2, the two ##STR53## groups may be the same or different;
*--Nu--Link--E--** (T-2)
wherein Nu represents a nucleophilic group, E represents an electrophilic group, being a group which is subjected to nucleophilic attack by Nu and with which the bond marked ** can be cleaved, and Link is a linking group which enables Nu and E to have a steric arrangement such that an intramolecular nucleophilic substitution reaction can occur; ##STR54## wherein, *, **, W, R.sub.11, R.sub.12 and t all have the same meaning as described above in connection with general formula (T-1); R.sub.11 and R.sub.12 may be joined together to form a benzene ring or a structural part of a heterocyclic ring; or R.sub.11 and R.sub.12 and W may be joined together to form a benzene ring or a heterocyclic ring;
Z.sub.1 and Z.sub.2 each independently represents a carbon atom or a nitrogen atom, and x and y represent 0 or 1;
when t is 2, the two ##STR55## groups may be the same or different; ##STR56## wherein * and ** in (T-4), (T-5) and (T-6) have the same meaning as described in general formula (T-1), in general formula (T-6) W have the same meaning as described in connection with general formula (T-1), and R.sub.14 has the same significance as R.sub.13.

### Claim 6 (depends on 1)

A silver halide photographic material as in claim 1, wherein L.sub.2 represents an electron transfer type timing group having a valence of at least 3.

### Claim 7 (depends on 1)

A silver halide photographic material as in claim 1, wherein L.sub.2 is represented by general formula (T-L.sub.2 ), ##STR57## wherein W represents an oxygen atom, a sulfur atom or an ##STR58## group (where R.sub.13 represents a substituent group), R.sub.11 and R.sub.12 each represents a hydrogen atom or a substituent group, Z.sub.1 and Z.sub.2 each independently represents a carbon atom or a nitrogen atom, X and Y each represents 0 or 1, t represents 1 or 2, * indicates the position at which A--(L.sub.1).sub.l -- in general formula (I) is bonded, and ** indicates the position at which (L.sub.1)n-PUG in general formula (I) is bonded and at least one of the plurality of R.sub.11 or R.sub.12 groups is bonded to --(L.sub.1).sub.n --PUG with a substituted or unsubstituted methylene group.

### Claim 8 (depends on 1)

A silver halide photographic material as in claim 1, wherein the coupler is present in an amount from 1.times.10.sup.-7 to 5.times.10.sup.-4 mol/m.sup.2.

### Claim 9 (depends on 8)

A silver halide photographic material as in claim 8, wherein the coupler is present in an amount from 1.times.10.sup.-6 to 2.times.10.sup.-4 mol/m.sup.2.

### Claim 10 (depends on 9)

A silver halide photographic material as in claim 9, wherein the coupler is present in an amount from 5.times.10.sup.-6 to 1.times.10.sup.-4 mol/m.sup.2.