US 4,108,850 AGranted

Positive-working immobile photographic azo compounds

AssigneeEastman Kodak Company

InventorsDonald Lee Fields, Richard Paul Henzel, Philip Thiam Shin Lau, Richard Allan Chasman

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Abstract

Photographic elements, processes for forming images in photographic elements and new compounds are disclosed. Generally, the invention relates to immobile compounds which can be used to provide positive images from negative recording-developing photographic materials such as negative silver halide emulsions. The compounds contain a photographically useful group such as a dye or dye precursor and are capable of releasing said photographically useful group under alkaline conditions, and are also capable of reaction with an oxidized silver halide developing agent before substantial release of said photographically useful group occurs, to provide a reaction product having a substantially lower rate of release of said photographically useful group. In specific embodiments, the compounds of this invention contain an electrophilic cleavage group located in the linkage between a ballast group and a photographically useful moiety wherein said electrophilic cleavage group is a carbamic acid derivative.

Claims47

Dependent claims

A compound according to the formula:

##STR10## wherein Nu is an oxidizable nucleophilic group or a precursor therefor;
E is carbonyl or thiocarbonyl;
Q is a bivalent group providing a mono atom linkage between E and R.sup.1 and is an amino group providing a mono atom nitrogen linkage, an oxygen atom, a sulfur atom or a selenium atom;
G.sup.1 is a substituent as defined for Nu or a dialkylamino group;
R.sup.6 is a bivalent alkylene group or a substituted alkylene group containing from 1-3 atoms in the bivalent linkage;
n is a positive integer of 1 or 2;
R.sup.1 is an aromatic group containing from 6-20 carbon atoms or an alkylene group or a substituted alkylene group containing 1-12 carbon atoms;
R.sup.2 is an alkyl group, a cycloalkyl group or a substituted alkyl group containing from 1-40 carbon atoms, an aryl group or a substituted aryl group containing from 6-20 carbon atoms, or the substituent X.sup.1 ;
R.sup.3, R.sup.4 and R.sup.5 are each a mono atom group which is a hydrogen atom or a halogen atom, a polyatomic group which is an alkyl group, a cycloalkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, or a sulfamyl group, the substituent X.sup.1 or a 5- to 7-membered cyclic group formed with Nu and R.sup.5 or G.sup.1 and R.sup.4 or R.sup.3, and the substituents for R.sup.3 and R.sup.5 or R.sup.4 and R.sup.5 when on adjacent positions on the ring may be taken together to form a 5- or 6-membered ring with the carbon atoms to which they are attached, with the provision that, when R.sup.1 is an alkylene group or a substituted alkylene group, R.sup.3 and R.sup.4 are polyatomic groups, and when G.sup.1 is a substituent defined for Nu, an adjacent R.sup.3 or R.sup.4 can be the group:
##STR11## X.sup.1 is provided in at least one of R.sup.2, R.sup.3, R.sup.4 or R.sup.5 and is a ballasting group or an azo dye moiety, provided one of X.sup.1 or (Q--R.sup.1 --X.sub.2) is an azo dye moiety, and one of X.sup.1 and (Q--R.sup.1 --X.sub.2) is a ballasting group which contains at least 8 carbon atoms and is of a size sufficient to render said compound immobile in an alkali-permeable layer of a photographic element.

7 more elements

A compound according to the formula:

##STR13## wherein Nu is an oxidizable nucleophilic group or a precursor therefor;
E is carbonyl or thiocarbonyl;
Q is a bivalent group providing a mono atom linkage between E and R.sup.1 and is an amino group providing a mono atom nitrogen linkage, an oxygen atom, a sulfur atom or a selenium atom;
G.sup.1 is a substituent as defined for Nu;
R.sup.6 is a bivalent alkylene group or a substituted alkylene group containing from 1-3 atoms in the bivalent linkage;
n is a positive integer of 1 or 2;
R.sup.1 is an aromatic group containing from 6-20 carbon atoms, an alkylene group or a substituted alkylene group containing 1-12 carbon atoms;
R.sup.2 is an alkyl group, a cycloalkyl group or a substituted alkyl group containing from 1-40 carbon atoms, an aryl group or a substituted aryl group containing from 6-20 carbon atoms, or the substituent X.sup.1 ;
R.sup.3 and R.sup.5 are each a mono atom group which is a hydrogen atom or a halogen atom, a polyatomic group which is an alkyl group, a cycloalkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, or a sulfamyl group, the substituent X.sup.1 or a 5- to 7-membered cyclic group formed with Nu and R.sup.5 or G.sup.1 and R.sup.3, with the provision that, when R.sup.1 is an alkylene group or substituted alkylene group, R.sup.3 and R.sup.5 are polyatomic groups;
and X.sup.1 is provided in at least one of R.sup.2, R.sup.3 or R.sup.5 and is a ballast group containing at least 8 carbon atoms and is of a size sufficient to render said compound immobile in an alkali-permeable layer of a photographic element, and each (Q--R.sup.1 --X.sub.2) is a carbocyclic monoazo dye moiety.

7 more elements

A compound according to the formula:

##STR14## wherein Nu is an oxidizable nucleophilic group or a precursor therefor;
E is carbonyl or thiocarbonyl;
Q is a bivalent group providing a mono atom linkage between E and R.sup.1 and is an amino group providing a mono atom nitrogen linkage, an oxygen atom, a sulfur atom or a selenium atom;
G.sup.1 is a substituent as defined for Nu or a dialkylamino group;
R.sup.6 is a bivalent group or substituted alkylene group containing from 1-3 atoms in the bivalent linkage;
n is a positive integer of 1 or 2;
R.sup.1 is an aromatic group containing from 6-20 carbon atoms, an alkylene group or substituted alkylene group containing 1-12 carbon atoms;
R.sup.2 is an alkyl group, a substituted alkyl group or a cycloalkyl group containing from 1-40 carbon atoms, an aryl group or substituted aryl group containing from 6-20 carbon atoms, or the substituent X.sup.1 ;
R.sup.3, R.sup.4 and R.sup.5 are each a mono atom group which is a hydrogen atom or a halogen atom, a polyatomic group which is an alkyl group, a cycloalkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, or a sulfamyl group, the substituent X.sup.1 or a 5- to 7-membered cyclic group formed with Nu and R.sup.5 or G.sup.1 and R.sup.4 or R.sup.3, and the substituents for R.sup.3 and R.sup.5 or R.sub.4 and R.sup.5 when on adjacent positions on the ring may be taken together to form a 5- or 6-membered ring with the carbon atoms to which they are attached, with the provision that, when R.sup.1 is an alkylene group or substituted alkylene group, R.sup.3 and R.sup.4 are polyatomic groups, and when G.sup.1 is a substituent defined for Nu, an adjacent R.sup.3 or R.sup.4 can be the group:
##STR15## X.sup.1 is provided in at least one of R.sup.2, R.sup.3, R.sup.4 or R.sup.5 and is a ballasting group or a carbocyclic monoazo dye moiety, provided one of X.sup.1 or (Q-R.sup.1 -X.sub.2) is a carbocyclic monoazo dye moiety, and one of X.sup.1 and (Q-R.sup.1 -X.sub.2) is a ballasting group which contains at least 8 carbon atoms and is of a size sufficient to render said compound immobile in an alkali-permeable layer of a photographic element.

7 more elements

A compound according to the formula:

##STR16## wherein Nu is an oxidizable nucleophilic group or a precursor therefor;
E is carbonyl or thiocarbonyl;
Q is a bivalent group providing a mono atom linkage between E and R.sup.1 and is an amino group providing a mono atom nitrogen linkage, an oxygen atom, a sulfur atom or a selenium atom;
G.sup.1 is a substituent as defined for Nu or a dialkylamino group;
R.sup.6 is a bivalent alkylene group or substituted alkylene group containing from 1-3 atoms in the bivalent linkage;
n is a positive integer of 1 or 2;
R.sup.1 is an aromatic group containing from 6-20 carbon atoms or an alkylene group or substituted alkylene group containing 1-12 carbon atoms;
R.sup.2 is an alkyl group, a cycloalkyl group or substituted alkyl group containing from 1-40 carbon atoms, an aryl group or substituted aryl group containing from 6-20 carbon atoms, or the substituent X.sup.1 ;
R.sup.3, R.sup.4 and R.sup.5 are each a mono atom group which is a hydrogen atom or a halogen atom, a polyatomic group which is an alkyl group, a cycloalkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, or a sulfamyl group, the substituent X.sup.1 or a 5- to 7-membered cyclic group formed with Nu and R.sup.5 or G.sup.1 and R.sup.4 or R.sup.3, and the substituents for R.sup.3 and R.sup.5 or R.sup.4 and R.sup.5 when on adjacent positions on the ring may be taken together to form a 5- or 6-membered ring with the carbon atoms to which they are attached, with the provision that, when R.sup.1 is an alkylene group or substituted alkylene group, R.sup.3 and R.sup.4 are polyatomic groups;
X.sup.1 is provided in at least one of R.sup.2, R.sup.3, R.sup.4 or R.sup.5 and is a ballasting group which contains at least 8 carbon atoms and is of a size sufficient to render said compound immobile in an alkali-permeable layer of a photographic element;
and (Q-R.sup. 1 -X.sub.2) is a carbocyclic monoazo dye moiety.

8 more elements

Dependencies are inferred from the claim text.

Facts

Application: 05/679,623Filed 23 Apr 1976 · division
Priority: 2 Oct 1974
Granted: 22 Aug 1978
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

G03C 8/18
Initially diffusible in alkaline environment: dye developers
G03C 5/3021
Developers: with oxydisable hydroxyl or amine groups linked to an aromatic ring
G03C 7/30547
Characterised by the released group: dyes
G03C 8/10
The substances transferred by diffusion consisting of organic compounds: of dyes or their precursors