CA1052610A - Positive-working immobile photographic compounds and photographic elements containing same - Google Patents

Abstract

POSITIVE-WORKING IMMOBILE PHOTOGRAPHIC COMPOUNDS
AND PHOTOGRAPHIC ELEMENTS CONTAINING SAME
Abstract of the Disclosure Photographic elements, processes for forming images in photographic elements and new compounds are disclosed. Gener-ally, the invention relates to immobile compounds which can be used to provide positive images from negative recording-develop-ing photographic materials such as negative silver halide emul-sions. 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 imagewise pattern of 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.

Description

~(~5~

POSITIYE-~ORKI~G I~MOBILE P~IOTOGRA~HIC COMP~UN~S
~ND PHOTOGRAPHIC ELE~IE~TS CONl`AI~ING SAME

This invention relates ~o r.ew compour.ds, photograp~ic elements and processes for for~.ing image records in pnoto-graphic elements. In one aspect, this invention relates to image dye-providing materials which are immobile or ballast-ed compounds as incorporated into photographic elements. In another aspect, this invention relates to dye image-provid- -ing materials which can be used in image transfer film units.
It is known in the art to use image dye-providing materials in photographic elements such as image transfer film units. Image dye-providing materials which are initially mobile in the film units have been employed, for example, such as the mobile couplers and developers disclos~d in U.S.
Patent 2,698,244 where a dye is synthetized in the receiver layer. Preformed mobile dyes which Teact with mobile oxidiz-ed color developers are disclosed in U.S. Patent 2,774,668.
i Further disclosures of the use of mobile preformed dyes are found in U.S. Patent 2,983,606. However, the initially mobile dye image-providing materials have certain disad~-antages in photographic elements: They can diffuse prematurely to adjacent layers thereby affecting interimage color reproduc-tion and they can remain reactive when diffusing through adjacent layers after development thereby causing drop-off in color scales.
Image dye-providing materials which are initially immobile in a photographic element or are ballasted overcome several of the problems with initially mobile compounds. The dyes could be temporarily baliasted by a heavy counter ion such as a barium salt as disclosed in U.S. Patent 2,756,142. The dyes can contain a removable ballast group as described ir.
Canadian Patent 602,607 and U.~. Patents 3~227J~5~ ana 3,62~,~52.
Compounds which undergo intramolecular ring closure upon o~ida-105;~10 tion to split off a dye are disclosed in U.~. ~atents 3,443,~9,3,443,5~40 and 3,~43,941. Improved initially immobile compounds which ~Indergo a redox reaction followed by alkali cleavage to split off a dye or dye precursor moiety are disclosed in Belgian Patent 788,268. However, these image dye-providing materials are generally limited in application because the dye is releas-ed in the areas where oxidation takes place. Thus direct- .
positive silver halide emulsions or some other reversing mech-anism, such as use of development nuclei in layers adjacent the recording layer, are used if a positive transfer image is desired.
It would be desirable to provide an image dye-providing material which is lnitially immobile or ballasted in a photo-graphic element to prevent premature movement, and have this material function to provide a positive transfer image with a simple negative silver halide emulsion. Moreover, it would be desirable to provide an image dye-providing material where-in the diffusing material is relatively inert to further reaction in the photographic element after it is released from the parent compound.
We have now discovered a class of compounds which can be used in photographic elements and in processes for producing image records which overcome many inherent limitations of the systems known in the art. These compounds are immobile or ballasted compou~ds which can undergo a reaction such as a nucleophilic displacement reaction in their reduced form to release a mobile and diffusible photographically useful moiety.
The compounds can be oxidized, such as by a redox reaction in a photographic element, to lower substantially the rate of release of the photographically useful moiety. Thus, the compounds can be used to provide a positive transfer image from negative sil-ver halide emulsions. In one embodiment of this invention the compound has a m.oiety which is released upon nucleophilic dis-.

1~)5~S~O
placement to provide a mobile image-~ye or image-d~re precursor.
The photographic elements of this invention include a support having thereon at least olle alkali-permeable layer which layer colltains an immoDile compound having a photo-graphically useful moiety such as an image-dye or image-dye prècursor. ~he immobile compound is capabie or releasing the photographically useful moiety under alkaline conditions and is capable of reaction with an imagewise pattern of an oxidized silver halide developing agent before su~stantial release of said photographically useful moiety occurs, to low-er substantially the rate of release of the photographically useful moiety under alkaline conditions.
The compounds of this invention when used in photo-graphic elements generally have a rate of release of the photographically useful moiety which rate is slower than the rate at which the compounds react with oxidized silver halide developing agent, but faster than the rate of fog formation in the unexposed areas of the photographic element. The rate of fog formation can be controlled by using slowly developing silver halide emulsions or the use of addenda which restrain or suppress further development after the initial imagewise development has occurred. Typical useful addenda to suppress further development include antifoggants, development restrainers and hydrolyzable precursors thereof.
In one embodiment, the compounds of this invention are organic compounds which contain 1) an oxidizable nucleophilic group and 2) an electrophilic group which is located between a moiety which is photographically useful and another moiety which functions as a ballast for the compound. When the compounds are used in a photographic system, the nucleophilic group functions by reacting at the electrophilic group, dis-placing either the ballast moiety or the photographically use-iOS~ ~0 _ 4 _ ful moiety from the compound. The photographically useful moietyupon release from the ballast moiety can thcn diffuse within the immediate layer, to adjacent layers or to receiver elements where it can carry out its ~unction in the system. ~owever, where the nucleo~hilic group is oxidized, such as by redox reaction with an oxidized silver haiide developer, the electrophilic group remains substantially unaffected by the oxidized nucleophilic group and the photographically useful moiety remains immobile and nondiffusible in its initial location.
The compounds of this invention are especially useful in photographic systems where the photographically useful moiety is an image dye-providing material such as a dye or dye pre-cursor. When the compounds are incorporated in a photographic element in association with a silver halide emulsion, the com-pounds function to provide a positive transfer of image dye-providing material with a negative silver halide emulsion.
Since the compounds are ballasted or immobile as incorporated in the photographic element, additional parameters of control are provided with resultant improved image quality. In certain preferre~ embodiments, a dye can be released which can diffuse through adjacent layers with a minimum of interaction ~ith silver halide or other compounds in the adjacent layers. S~ill another advantage is attained in certain embodiments where a shifted or preformed dye can be released from an immobile compound associated with a negative silver halide emulsion to produce an image record without the necessity of oxidation reactions on the receiver sheet, such as is required with oxichromic compounds, leuco compounds, and color couplers which generally require oxidation reactions to provide the image dye.
In a preferred embodiment, this invention relates to photographic elements which include a support having thereon a red-sensitive silver halide emulsion having assoclated there-with an int.zmolecular nucleophilic dicpl~cement compound hav-ing a cyan image dye-providing moiety, a layer containing a ~?5~SlO - 5-green-sensitive silver hali~e emulsioJl having associated there-with an intramolecular nucleophilic displacement compound hav-ing a ~.agenta image dye-providing moiety, and a layer con-taining a blue-sensitive silver halide emulsion having asso-ciatecl therewith an intramolecular nucleophilic displacement compound having a yellow image dye-providing moiety.
In a specific embodiment in accordance with this inven-tion, a photographic film unit is provided which is adapted to be processed by passing the unit between a pair of juxta-posed pressure-applying members, such as would be found in a camera designed for in-camera processing. The unit comprises 1) a photosensitive element which contains a silveT halide emulsion having associated therewith an immobile intramolecular nucleo-philic displacement compound having an image dye providing moiety, 2) an image dye-receiving layer, 3) means for discharg-ing an alkaline processing composition within the film unit such as a rupturable container which is adapted to be position-ed during processing of the film so that a compressive force applied to the container by the pressure-applying members will effect a discharge of the container's contents within the film, and 4) a silver halide developing agent which is soluble in alkaline processing composition located within said film unit.
; In still another embodiment, this invention relates to a new process whereby an alkaline processing composition is applied to an imagewise-exposed photographic element includ-ing a support having thereon at least one layer containing a photographic recording material, such as silver halide, and at least one layer thereon containing a nondiffusible compound having a photographically useful moiety. The compound being capabl~ of releasing the photographically useful moiety under alkaline conditions, and also being capable of reaction with an oxidi~ed developing agent for said photographic recording material, wherein the reaction product has a substantially lQ5'~0 ~ower rate of release of the photographically useful group.
The process also includes providing the developing agent ~or the photographic recording material duri~lg application of the alkali.ne processing composition under conditions to effect ima~ewise release of the photographically useful moiety as an inverse Iunction of development oi the photograp;lic recording material, whereby an image record is obtained in the photographic element.
ln a highly preferred embodiment, this invention relates to a photographic transfer process of:
a) treating an exposed photographic eler,lent which includes a support havi.ng thereon at least one alkali-permeable layer which layer contains an immobile compound having a photographically use-ful moiety with an alkaline processing composi-~ tion in the presence of a silver halide develop-: ing agent to effect development of each of the exposed silver halide emulsion layers, thereby oxidizing the developing agent;
. b) cross-oxidizing the immobile compound by the oxidized developing agent as a function of development before substantial release of the photographically useful moiety occurs whereby the cross-oxidation substantially reduces the rate of release of the photographically useful .~ moiety.
c) maintaining the photographic element in an alkaline medium for a time sufficient to release the photo-graphically useful moiety from the immobile compound which has not reacted with the developing agent; and whereby at least a portion of the photographically useful moiety provides a positive image record.

105;~ 0 ,7, In this highly preferred embodiment, the photographically usefull moiety is preferably an image dye or image-dye precursor.
The photograp}lic transfer process is preferably carried out in an in1:egral negative-receiver image t.ansfer element ha~ing the image-receivin~ layer and the photographic recording layers coated on the same support. Preferably an opaque layer which is reflective to light is located between the receiving layer and the recording layers. The alkaline processing composi-tion can be applied between the outer recording layers of the photographic element and a cover sheet which can be transparent and superposed before exposure.
Reversal images can be readily obtained with photo-graphic elements of this invention, and especially those ele-ments which contain a immobile compound which contains a hydro-ly~able precursor or the nucleophilic group. The elements can be first developed with a developing agent in an environment having a pH below that necessary to hydrolyze the precursor for the nucleophilic group; then the photographic element can be fogged, light-flashed, and developed in a solution having a pH suffiriently high to effect intramulecular nucleophilic displacement of the immobile compounds.
Generally, the immobile compounds contain a nucleophilic group a~d an electrophilic group so chosen that, when the compound is incorporated into a photographic element, the rate of oxidation of the nucleophilic group is substantially great-er than the rate of intramolecular nucleophilic displacement :
or cleavage at the electrophilic group. Since the rate of oxidation is substantially greater than the rate of nucleo-philic displacement, an imagewise pattern of the more mobile group will be produced after displacement; i.e., where the compound contai~s an image dye wh~ch is diffusible after nucleophiliG displacement, an image record can be observed in layers adjacent the layer of initial location of the com-10526~0 _ ~~ound. Ceneral.y, tl~a~ will be ~t 'e~st 1~ ~nd pre~erablr at least 100~ more of the nucl~ophilic displacement in the un-oxidized areas than in the oxidized areas, and preferably there is substantially no nucleophilic displacement in the areas of the photographic element where all of the compound is oxidized.
~here dyes or dye precursors are released, generally at least two times ~nd preferably at least five time~ more dye or dye precursor is released in the unoxidized areas than in the OXi~lZ-ed areas.
In ~ertain highly preferred embodiments, the compounds of this invention contain a group which is a hydrolyzable pre-cursor for the oxidizable nucleophilic group, for example, a hydrolyzable precursor for a hydroxylamine group. In com-pounds where the nucleophilic group is blocked, the possibility of premature reactions' releasing the photographically useful moiety is substantially eliminated. Moreover, by controliing the development conditions, the availability of the nucleophilic group for reaction and intramolecular nucleophilic displacement can be delayed, if desired.
In certain preferred embodiments, the compounds of this invention are defined as intramolecular nucleophilic displace-ment compounds. The term "intramolecular nucleophilic dis-placement" is understood to refer to a reaction in which a nucleophilic center attached to a compound reacts at another site on the compound, which is an electrophilic center, to effect displacement of a moiety attached to the electrophilic g~roup. Generally, the intramolecular nucleophilic displace-ment compounds are those compounds which have the nucleophilic group and the electrophilic group juxtaposed by the three-dimensional configuration of the molecule to promote close proximity of the groups where~y the reaction can take place.
~enerally, the respective electrophilic and nucleophilic groups can be put on any compound where the groups are held in *he pos-- lOS'~10 - 9 sible reactioll ~o~itlons, lnclu~in~ ~olymc3ic compounas, maoro-cyclic compounds, polycyclic compounds, en7yme-like structures and t~he li`~e.
~ lowever, the nucleophilic grou~)s and electrophilic groups are preferably located on compounds wherein a cyclic organic ring or a transient cyclic organic ring can be easily formed by intramolecular reaction of the nucleophilic group at the e~ectrophilic center. Cyclic groups can be generally formed with 3-7 atoms thereon, and preferably in accordance with this invention the nucleophilic group and the electrophilic group are positioned on a compound where they can forma 3- or 5-to 7-membered ring, and more preferably a 5- or 6-membered ring (4-membered rings are generally known to be difficult to form in organic reactions). Intramolecular nucleophilic dis-placement occurs with the compounds of this invention when the compound is in the reduced state and the rate of nucleophilic displacement appears to be substantially reduced and prefer-ably eliminated when the nucleophile is oxidized. The mech-anism of the above compounds as described is belie~ed to be different in kind from compounds known in the art which are oxidized to provide an electrophilic center with subsequent intra-molecular reaction followed by release of a dye.
Compounds which undergo intramolecular nucleophilic ~ -displacement can generally be readily distinguished from com-pounds which undergo intermolecular nucleophilic displacement by observing the reaction characteristics of the respective compounds. In one test, a mixture of compounds according to this invention, which have been modified by blocking the nucleo-philic groups on some and using a different, readily distinguish-able release group on others, will undergo release of the photo-graphically useful moiety much slower from the blocked compounds than from the unblocked compounds, especially when carried out in an aqueous alkaline medium, i.e., such as an alkali-permeable hydrophilic colloid saturated with mildly alkaline solutions.

1(~5'~0 lhe conlpoun~s o~ this inve~ oll preiel~ably con~aln tne nucleophilic groùps and the electrophilic groups connected throu~h a ~inka~e which can be ac~clic, but is preferably a cyclic group to provide more favorable juxtaposition of the groups whereby intramolecular nucleophilic attack on the elec-trophilic center is favored. In certain highly preferred embodiments. the nucleophilic group and the electrophilic group are both attached to the same aromatic ring structùre, which includes fused rings wherein each group can be on a different ring; preferably, both groups are attached to the same aromatic ring.
In certain embodiments, the compounds of this inven-tion contain from 1 to about 5 atoms and preferably 3 or 4 atoms between the nucleophilic center of the oxidizable nucleophilic group and the atom which forms the electrophilic center, whereby the nucleophilic center, taken together with the center of the electrophilic group, is capable of forming a ring or a transient ring having from 3 to 7 atoms therein and preerably 5 or 6 atoms therein.
The new compounds of this invention have the following structure:
;

Nu E-Q-X2 tR2)"1 1 tR3)n-1 \ l R
. Xl R is a acyclic, cyclic, or polycyclic organic group. R
preferably has from 5-7 members in the ring in which Nu and E are attached, and is more preferably an aromatic ring includ-ing fused rings or substituted aromatic rings. Prefera~ly contains less than 50 atoms and more preferably less than 15 atoms. l~

~05'~6~0 R and R3 are bivalent org~nic groups containing from 1-3 atoms in the bivalent lin~age, such as alkylene, oxal~ylene, or thialkylene ~roups. R3 contains a carbon atom covalently bond-ed to E.
Nu is an oxidi.zable nucleophilic group or a precursor for an oxidizable nucleophilic group inc,uding precursors such as hydrolyzable cyclic groups formed together with substituents on ~-Rl. Oxidizable nucleophilic groups include for example, a hydrazine group:
(-N-N-R4), H H
a hydroxyamino group: .

. (-N-O~), including a hydrolyzable precursor for a hydroxyamino group such as:

-C/ or (-N-O-R ), :~
O
: a hydroxy group (-~H) including precursors for a hydroxy group such as ~-o-R6), a primary amino group t-NH2) including precur-sors for a primary amino group, such as:
.i H
_N-R6 R6 can be a hydrolyzable group such as an acyl group compris-ing from 2-10 carbon atoms. R4 is an alkyl group haYing from 1-10 carbon atoms including substituted alkyl groups, an aryl group ha~ing from 6-20 carbon atoms including substituted aryl groups or a group mentioned for R6. R5 can be a hydrogen atom or any group useful for R4.
.'~ ' .

1~5Z6~0 ` _ / ~
is an electrophilic group and is preferably a carbonyl gI`OUp ~-C-) or a sulfonyl group (-SO2-).
Q is a bivalent group providing a mono atom linkage be-tween E and X2 wherein said mono atom îs a nonmetallic atom of group V~ or VIA of the periodic table in its -2 or -3 valence state, such as a nitrogen atom, a oxygen atom, a sulfur atom, a seleniw~ m and the like. The mono aton-. provides the two covalent bonds linking X2 to E, and when it is a trivalent atom it can be monosubstituted with a hy~rogen atom, an alkyl group containing from 1-10 carbon atoms, including substituted carbon atoms and carbocyclic groups, or an aryl group contain-ing from 6-~0 carbon atoms including substituted aryl groups.
One of Xl or Q-X2 is a ballasting group of sufficient size to render the compound immobile in an alkali-permeable layer of a photographic element, and one of Xl and Q-X2 is a photographically useful moiety such as an image dye, an image-dye precursor, an antifoggant moiety, a toner moiety, a fix-ing agent, a development accelerator, a developing-agent moiety, a hardener moiety, and the like, including the necessary linking groups to attach the respective moiety to E or Rl. n and m are positive integers of 1 or 2.
Rl, R2 and R3 are selected to provide substantial proximity of Nu to E to permit intramolecular nucleophilic cleavage of Q from E and are preferably selected to provide 1 or 3 to 5 atoms between the atom which is the nucleophilic center of said nucleophilic group and the atom which is the electrophilic center, whereby the compound is capable of form-ing a 3- or 5- to 7-membered ring and most preferably a 5-or 6-membered ring upon intramolecular nucleophilic displace-ment ~f the group -Q-X2 from the electrophilic group.
In the above formula where Q-X2 is the photographi-~ally useful moiety, a photographically active group can be made available by Q upon cleavage of Q-X from the remainder of the compound, i.e., such as where Q-X forms a mercapto-- `~
105;~610 te!trazole and the like. However, where xl is the photograph-ic:ally useful group, the group should be attached in a manner so that it does not rely upon the cleavage to provide a photogr~phically useful species.
The nature of the ballasting groups in the above com-pounds is not critical as long as the portion of the compound on the ballast side of E is primarily responsible for the immobility. The other portion of the molecule on the re-maining side of E generally contains sufficient solubilizing 10 groups to render it mobile and diffusible after cleavage.
Thus, Xl could be a hydrogen atom if R , R and R confer sufficient insolubility to the compound to render it immobile.
However, when Xl or X2 serve as the ballast function, they generally comprise long-chain alkyl radicals, as well as lS aromatic radicals of the benzene and naphthalene series.
Typical, useful groups for the ballast fun~tion contain at least 8 carbon atoms and preferably at least 14 carbon atoms.
The term "nucleophilic group" as used herein refers to an atom or group of atoms which have an electron pair ; 20 capable of forming a covalent bond. Groups of this type are sometimes ionizable groups which react as anionic groups.
The term "oxidizable nucleophilic group" refers to that nu-cleophilic group which can be oxidized, thus causing a sub-stantial reduction in the rate of intramolecular nucleophilic displacement relative to the electrophilic group. Generally, the groups are less nucleophilic in character upon oxidation or have a structure which adversely affects the proximity of the nucleophilic center w-th respect to the electrophilic ; center.
The nucleophilic group can contain only one nucleo~
- philic center such as the oxygen atom in an hydroxy group, ~ - 13 -lOSZ610 or it can contain more than one nucleophilic center such as in the case of an hydroxylamine group where either the nitrogen atom or - 13a -~ )5'~61V
the oxygcll atom can be the nucleopl1ilic ccnter. I~lhere more than one nucleo~hilic ceJIter is present in the nucl~ophilic group on the intramolecular nucleophilic displaccmcnt cor.lpowlds of this inven1;ion, the nucleophilic attack and displacement will gener-ally occur through the center which is capable of forming the most favored ring structure, i.e.; if the oxygen atom of the hydroxylamine group would form a 7-membered ring and the nitro-gen atom would form a 6-membered ring, the active nucleophilic center would generally be the nitrogen atom.
The term "electrophilic group" refers to an atom or group of atoms which are capable of accepting an electron pair to form a covalent bond. Typical electrophilic groups are as defined above for E. The term "electrophilic cleavage group"
is used herein to refer to a group ~-E-Q-) wherein E and Q
are as defined above.
Bi~alent groups are referred to in the above formula definitions. It is understood that the linkage in said bivalent groups refers to the shortest chain of atoms in the respective groups between the covalent bonds shown in said formula.
; The term "nondiffusing" used herein has the meaning commonly applied to the term in photography and denotes materi-als which for all practical purposes do not migrate or wander through organic colloid layers of photographic elements in an alkaline medium. The same meaning is to be attached to the term "immobile".
- The term "diffusible" as applied to the materials of this invention has the converse meaning and denotes materials having the property of diffusing effectively through the colloid layers o~ the photographic elements in an alkaline medium in the presence of "nondiffusing" materials. "Mobile" has the same meaning.
In one highly preferred embodiment, the immobile com-pounds of this invention are 2,1-benzisoxazolones linked to a photographically usoful moiety such as a dye or ~ye precursor.

. .......... .

~05~610 The dye can be connected to the ben~isoxa~olollc moi~ty through an electrophilic clcavage group or it can be attachcd directly to the benzisoxazolone moiety with the provision that a ballast group is attached to thc benzisoxazolone moiet~ through an electrophilic cleavage group. These compounds can be represent-ed by thc fcrmula:

(R3)m l-E-Q-X2 X~ 2)n-1~N-R~
o=c o wherein Xl, X2, E, Q, and R4 are as defined above. R2 and R3 are bivalent organic groups containing 1 or 2 atoms in the bivalent linkage and n and m are ~. Q-X2 is preferably a dye or dye precursor including the necessary linking groups to attach the dye or dye precursor to Q or the benzene ring of said formula. E is preferably a carbonyl group; and Q is a bivalent group containing a nitrogen atom linking E to X2.
Typical immobile compounds of this invention are shown below. The symbol ~ represents a phenyl group.

..

CH3-N-CH2CH2N ~N=N~S02NH2 O-C CH3 ~2~I5 ; ~18H37-M-C ~N,~o Compound I

. C~3 CH3~ CH2CH2NSC2~ N-N~OH
C18H37-N-C ~ ~ Cl ,- .

105~10 c, ~13 N-cH2c'l2c~l2'`l~Iso2 i~
O=C ÇH3 ~ 802CH3 - Co~ o~ld III OH

CH3 C~3 ~N=N~ OC0 0 ,N-C~I2CH2-N--S2 C-N
O=C ~H3 ~ N Conlpov.nd IV
CH3 r~ O
H37C~ `iCO~ C~
O
, C, H3 ,C~3 N-CH2CH2-M-S02~j O=C C,H3 ~
H37CIS-NCO~ C~ N NHS02C}-13 : . ¢~ ,, ._' ' ' ' ' ' . ' '~,H3 CH3 ¢~
N-CH2CH2-N-s02 ~SO2r~I N

H37C18i~C ~ ,C,' ornpo !~S02CH3 ~(~5;~610 The photogralhic processes usin~ thc immobile com-pounds are generally carried out in an alkaline mèdinm where-in the nucleophilic displacement can easily take place. In certain embodiments, the processes are carried out in an alkaline medium having a pH of above 12. At a hi~h p~l-, silver halide development proceeds rapidly and dye mobility is generally high. High-p~l conditions are especially prefer~ed for image-transfer processes using the compounds of this invention. ~iore-over', when the 2,1-benzisoxazolone compounds as described above are used in photographic elements, they are generally contact-ed with an alkaline solution at a pH sufficiently high to hydrolyze the isoxazolone ring to form an hydroxylamino group. The compound can then react with an oxidized silver halide developer to re-duce the rate of release of the photographically useful group;
however, where the compound remains unoxidized, the photographi-cally useful group is released.
The compounds of this invention can generally be prepared by using conventional techniques used in organic chemistry wi~h proper selection of the starting materials. The photo-graphically useful group can be synthesized by methods known in the art with the appropriate linkages and groups for reaction with the remainder of the compound. The examples define a typical preferred procedure where the acid chloride of a 2,1-benzisoxazolin-3-one is reacted with,a dye with an amine group thereon by a Schotten-Baumann reaction to produce compounds in accordance with this invention.
In certain preferred e,mbodiments, the compounds of this invention contain a moiety which is an image dye-providing material. Preferably, the image dye-providin~ moiety is a pre-formed dye or a shifted dye. Dye materials o~ this type are well-known in the art and include dyes such as azo dyes, azo-methine (imine) dyes, anthraquinone dyes, ali~arin dyes, mero-cyanine dyes, quinoline dyes, cyanine dyes and th~ like. The _ 1 7 _ 105;~6~0 ~ /~
shift~d dyes inclu~e those compoull~s whcrein the li~ht ahsorp-tion characteristics are shifted hypsocllromically or bathochro-mically t~hen subjected to a different environment such as a change in pll, reactioll with a material to form a complex, tauto-merization, reactions to chan~e the p~a of the compound, and removal of ~ ~roup such as a hydroly~able acyl group connect~d to an atom of the chromophore as mentione~ in U.S. Patent 3,260,597.
The shifted dyes are highly preferred and especially those containing a hydrolyzable group on an atom affecting the chromophore resonance structure are highly preferred, because the compounds can be incorporated directly in a silver halide emulsion layer or even on the exposure side thereof with-out su~stantial reduction in the recordi.ng light exposure.
After exposure, the dye can be shifted to the appropriate color such as, for example, by hydrolytic removal of an acyl group to provide the respective image dye.
Irl another e~lbodiment, the compounds of this invention contain a moiety which is an image-dye precursor. The term "image-dye precursor" is understood to refer to those compounds, which u~dergo reactions encountered in a photographic imaging system to produce an image dye, such as color couplers, or oxichromic compounds.
When color couplers are present in the compounds of this inventio~, the coupler can be released in areas where no development occurs and can diffuse to an adjacent layer where they can be reacted with an oxidized color developer such as a primary aromatic amine to form the image dye. Generally, ~he color coupler and the color developer are so chosen that the reaction product is immobile. Typical us~ful color couplers include the pyrazolone couplers, pyrazolotriazole couplers, open-chain ketomethylene couplers, and phenolic couplers. Further reference to the descri~tion of appropriate couplers is found in U.S. Patent 3,620,747.

10~ 610 ~ 1 The photograpilically useful moiety represented by Q-X2 or Xl in the above formula can be a silver halide development innibitor including triazole~ and tetrazoles such as a 5-mer-capto-1-phenyltetrazole, a 5-methylbenzotriazole, a 4,5-dichlo-robenzotriazole and the like, and it can also be an antifoggant including azaindenes such as a tetrazaindene and the like. The compounds which contain releasable silver halide development inhibitors or antifoggants can generally be used in the photo-graphic elements in association with silver halide layers wherein said compound can be incorporated in amounts such as 1 to 100 mg./ft.2 dissolved in a coupler solvent such as diethyl lauramide. When these compounds are incorporated in photo-graphic elements in association with negative silver halide emulsions, a positive imagewise distribution of inhibitor or antifoggant will be produced upon development. Thus, silver development is inhibited or restrained in the low-exposure toe as seen on the H and D curve, but not in the more fully exposed shoulder as seen on the H and D curve. Development inhibition of the unexposed areas is thereby achieved selectively. When the silver halide emulsions also h~ve dye releasers in accor-dance with this invention associated therewi~h, the overall effect of the inhibitor or antifoggant is to release more dye in the unexposed regions, improving maximum image dye density to the image-receiving layer without increasing the amount of dye released n the exposed regions.
The photographically useful moiety represented by Q-X2 or Xl can also be a silver halide development accelerator such as a benzyl alcohol, a benzyl ~-picolinium bromide and the li~e, a foggant including hydrazines and hydrazides such as an ace~yl-phenylhydrazine and the like, or an auxiliary developer such as a hydroquinone, a l-phenyl-3-pyrazolidone, an ascorbic acid and the like. When these compounds are used in photographic ele-k ~ -18a ~OSZ610 ments in association with silvel halide emulsions which also have associated t~lerewith image dye-providing materials in accordance with this invention, the released dye density of all dyec; in the unexposed regions would be somewhat reduced by fog development. If, however, one layer was unexposed while the other t-:o ~,ere given an imagewise exposure, the amount of fog-gant or development accelerator reaching the unexposed layer from the other two layers would be less where those layers were exposed. Hence, the Dmax of the unexposed layer would increase as a function of exposure of the other two layers. This greatly enhances the saturation of single colors in a photograph.

-18b-i()5~610 The compounds of this invention oontaining oxichromic moieties can also be advantageously used in a photographic system since they are generally colorless materials due to the the absence of an image-dye chromophore. Thus, they can also be used directly in the photographic emulsion or on the ex-posure side thereof without competitive absorption. Com-pounds of this type are those compounds which undergo chromo-genic oxidation to form the respective image dye. The oxi-dation can be carried out by aerial oxidation, mncorporation of oxidants into the photographic element or film unit, or use of an oxidant during processing. Compounds of this type have been referred to in the art as leuco compounds, i.e., compounds which have no color. Typical useful oxichromic compounds include leuco indoanilines, leuco indophenols, leuco anthraquinones and the like. In certain preferred embodiments the compounds of this invention contain oxichromic moieti~s as described in Belgian Patent 792,598.
The compounds described herein have particular appli-cation in a diffusion transfer process where it is desired to have a dye entity transferred to an adjacent layer or a re-ceiving element. However, it has broad application to photo-graphic processes in which it is desired to release an image-wise distribution of a diffusible photographically useful compound. Thus, the photographically useful group may also be, for ex~mple, a silver complexing agent, a silver halide solvent, a fixing agent, a toner, a hardener, an antifoggant, a fogging agent, a coupler, a sensitizer, a desensitizer, a developer or an oxidizing agent. In other words, Xl and Q-X2 in the above formula may represent any moiety which, in coml bination with a hydrogen atom, forms a photographically useful compound upon oleavage.

~05;~6~0 The compow~ds of this invention are particularly useful in photographic ~lements and in photographic processes t:o provide an imagewise distribution o~ a photographically useful compound. The photographic element can contain the immobile compounds in association with any photographic material which produces an oxidation product during develop-ment which in turn can react with the nucleophilic group on said compound. In certain preferred embodiments, where sil-ver halide emulsions are used as the recording means, the emulsion can be a negative, direct-positive or reversal emulsion and the like which undergo development with a silver halide developing agent to produce oxidized silver halide developer. The oxidized silver halide developing agent can react with the nucleophilic group to producè an addition pro-duct and the like, but preferably the silver halide de~elop-ing agent is so chosen that a simple redox reaction takes place to reduce substantially the rate of release of the photographically useful moiety.
Black-and-white or one-color systems can be made which employ as few as one silver halide emulslon and com-pounds according to this invention which comprise the required image dye-providing moieties to provide the desired net color effect. Preferably, the compounds of this invention are used in three-color systems such as, for example, photographic elements having a layer containing a red-sensitive silver halideemulsion having associated therewith an intramolecular nucleophilic displacement compound having a cyan image dye-providing moiety, a layer containing a green-sensitive silver halide emulsion having associated therewith an intramolecular nucleophilic displacement compound which has a magenta image dye-providing moiety, and a layer containing a blue-sensitive -- lOS;~610 silver halide emulsion having associated therewith an intra-molecular nucleophilic displacement compound which has a yellow image dye-providing moiety.
The photographic element can be designed to provide an image record in either the image dye-providing material re-leased and made diffusible or in the immobile dye remaining in the initial location attached to the oxidized compound and associated with the respective photographic recording mater-ial or, in certain instances, both image records can be used.
The residual nondiffusible dye can provide an image record which will be present as a function of silver halide develop-ment. The silver and silver halide remaining after develop-ment can be removed, if desired, to provide better color pro-perties in the~-record.
In certain preferred embodiments, the photographic element is used in an image-transfer film unit where the dye image-providing material upon release diffuses to an adjacent image-receiving layer. The compounds of this invention can be used in any image-transfer film unit where either initially mobile comPounds are used, such as dye developmrs, or where the initially immobile compounds are used, such as ballasted redox releasing compounds. Typical useful image-trans~er fi~m units are disclosed în U.S. Patents 2,543,181, 2,661,293,

2,774,668, 2,983,606, 3,227,550, 3,227,552, 3,309,B01,

3,415,644, 3,415,645, 3,415,6a6, and 3,635,707, Canadian Pa-~
tent 674,082, and Belgian Patents 757,959 and 757,960. How-ever, the appropriate silver halide emulsions will have to be used in each unlt since the present compounds yield a positive image in di~fusible dye with a negative recording and develop-ing emulsion.

`lOS;~610 In certain embodiments, the photo~raphic elements of this invention are processed in the presence of a silver halide developing agent which is preferably a silver halide developing agent which as a redox potential whereby it will cross-oxidize when oxidized with immobile compounds of this invention. Typical useful silver halide developers include hydroquinone campounds such as hydroquinone, 2,5-dichloro-hydroquinone, and 2-chlorohydroquinone; aminophenol compounds such as 4-aminophenol, N-methylaminophenol, 3-methyl-4-aminophenol, and 3,5-dibromoaminophenol; catechol compounds such as catechol, 4-cyclohexylcatechol, 3-methoxycatechol, and 4-(N-octadecylamino)-catechol; phenylenediamine compounds such as N, N-diethyl-~-phenylenediamine, 3-methyl-N,N-diethyl-~-phenylene-diamine, and 3-methyoxy-N-ethyl-N-ethoxy-~-phenylenediamine; 3-pyrazolidone compounds such as l-phenyl-3-pyrazolidone, 1-pheyl-4,4-dimethyl-3-pyrazolidone, 4-hy~
droxymethyl-4-methyl-1-phenyl-3-pyrazolidone, 1-m-tolyl-3-pyrazolidone, l-~-tolyl-3-pyrazolidone, 1-phenyl-4-methyl-3-pyrazolidone, l-phenyl-5-methyl-3-pyrazolidone, 1-phen~1-4,4-bis-(hydroxymethyl)-3-pyrazolidone, 1,4-dimethyl-3-pyrazoli-done, 4-methyl-3-pyrazolidone, 4,4-dimethyl-3-pyrazolidone, 1-(3-chlorophenyl)-4-methyl-3-pyrazolidone, 1-(4-chloro~
phenyl)-4-methyl-3-pyrazolidone, 1-(3-chlorophenyl~-3-pyra-zolidone, 1-(4-chlorophenyl)-3-pyrazolidone, 1-(4-tolyl-4-methyl-3-pyrazolidone~, 1-(2-tolyl~-4-methyl-3-pyrazolidone, 1-(4-tolyl)-3-pyrazolidone, 1-(3-tolyl~-3-pyrazolidone, 1-(3-tolyl~-4,4-dimethyl-3-pyrazolidone, 1-(2-trifluoroethyl~-~ 4,4-dimethyl-3-pyrazolidone, and 5-methyl-3-pyrazolidone.
: A plurality of developing agents such as those dis-closed in U.S. Patent 3,039,869 can also be employed. Such 1~5;~610 `
developing agents can be employed in the liquid processing composition or may be contained, at least in part, in any layer or layers of the photographic element or film unit such as the silver halide emulsion layers, the dye image-providing material layers, interl~yers, image-receiving ;~
layer, etc.
In highly preferred embodiments of this invention, the photographic element or film unit contains a compound in addi-tion to said immobile compounds, which is an antifoggant or ` `
development restrainer which substantially prevents any further development of a silver halide emulsion after the initial imagewise development has occurred. Generally, the compound is one which will at least prevent fog buildup in a silver halide layer during the time necessary to release a substantial amount of the photographically useful group from the unoxidiz~d compound. Typical useful develppment restrain-er precursors which can be used to permit initial develop-ment but restrain development thereafter are disclosed in U.S. Patent 3,260,597. Conventional development restrainers can also be used in the photographic elements or film units wherein they are located in the processing composition, in layers adjacent the silver halide emulsion layers, in the receiving element, in a cover sheet/ etc., where contact with the silver halide emulsion is delayed until after the initial image-recording development has occurred.
In a photographic element according to the invention, each silver halide emulsion layer containing a dye image-~ providing material or having the dye image-prouiding material ; present in a contiguous layer may be separated f~om the other silver halide emulsion layers in the negative portion of the lOS~610 film unit by materials in addition ~ those described above, including gelatin, calcium alginate, or any of those disclosed in U.S. Patent 3,384,483, polymeric materials such as poly-vinylamid~s as disclosed in U.S. Patent 3,421,892, or any oi those disclosed in French Patent 2,028,236 or U.S. Patents 2r992,104, 3,043,692, 3,044,873, 3,061,428, 3,069,263, 3,069,264, 3,121,011 and 3,427,158.
Generally speaking, except where noted otherwise, the silver halide emulsion layers in the invention comprise photo-sensitive silver halide dispersed in gelatin and are abo~t 0.6 to 6 microns in thickness. The dye image-providing materials are dispersed in an aqueous alkaline solution-permeable poly-meric binder, such as gelatin, in the same layer as the silver halide emulsion or as a separate layer about 1 to 7 microns in thickne3s. The alkaline solution-permeable polymeric interlayers, e.g., gelatin, are about 1 to 5 microns in thickness. Of course, these thicknesses are approximate only and can be modified according to the product desired. In addition. to gelatin, other suitable hydrophilic materials incl~de both naturally occurring substances such as proteins, cellulose derivatives, polysaccharides such as dextran, and gum arabic; and synthetic polymeric substances such as water-soluble polyvinyl compounds like poly tvinylpyrrolidone)~ and acrylamide polymers.
- 25 The photographic emulsion layers and ~ther layers of a photogra~hic element employed in the practice of this invention ca~ also contain, alone or in combination with hydrophilic, water-permeable colloids, other synthetic poly-meric compQunds such as dispersed vinyl compounds such as in ~0 latex form, and particularly those whihh increase the dimen-105~6iO ` `
sional sta~ility of the photographic materials. Suitable synthetic polymers include those described in U.S. ~atents 3,142,568, 3,193,386, 3,062,674, 3,220,844, 3,287,289 and 3,411,911. Particularly effective polymers are water-insoluble polymers of alkyl acrylates and methacrylates,acrylic acid, sulfoalkyl acrylates or methacrylat~s, those polymers which have cross-linking sites which facilitate hardening or curing r and those polymers havl~g recurring sulfobetaine units as described in Canadian Patent 774,054.
Any material can be employed as the image-receiving layer in the film units of this invention as long as the desired function of mordanting or otherwise fixing the dye images will be obtained. The particular material chosen will, or course, depend upon the dye image to be mordanted as meh-tioned hereinbefore. , Use of a pH-lowering layer in the film units of the invention will usually increase the stability of the trans-ferred image. ~nerally,the p~-lowering layer will effect a reduction in the pH of the image layer from about 13 or 14 to at least 11 and preferably 5-8 within a short time after ;nhibition. Far example, polymeric acids as disclosed in U.S. Patents 3,362,819, 2,584,030, or 2,548,575, or Belgian Patent 603,747 may be employed in the p~-lowering layer.

Such polymeric acids reduce the p~ of the film unit after development to terminate development and substantially reduce further dye transfer and thus stabilize the dye image. Suah polymeric acids comprise polymers containing acid groups, such as carboxylic acid and sulfonic acid groups, Which are capable of forming salts with alkali metals, such as sodium or potassium, or with organic bases, particularly quaternary ammonium bases, such as tetramethyl ammonium hydroxide. The lOSZ6~0 '~
polymers can also contain potentially acid-yielding groups such as anhydrides or lactones or other groups which are capable of reacting with bases to capture and retain them.
Generally, the most useful polymeric acids contain free s carboxyl groups, being insaluble in water in the free acid form and which form water-soluble sodium and/or potassium salts. Examples of such polymeric acids in~lude dibasic acid half-ester derivatives of cellulose, which derivatives contain free carboxyl groups, e.g., cellulose acetate hydro-gen phthalate, cellulose acetate hydrogen gluturate, cellu-lose acetate hydrogen succinate, ethyl cellulose hydrogen succinate, ethyl cellulose acetate hydrogen succinate, cellulose acetate succinate hydrogen phthalate; ether and - ester derivatives of cellulose modified with sulfoanhydrides, e.g., with ortho-sulfobenzoic anhydride; polystyrene sulfonic acid; carboxymethyl cellulose; polyvinyl hydrogen phthalate;
polyvinyl acetate hydrogen phthalate; polyacrylic acid, acetals of polyvinyl alcoho~ with carboxy or sulfo-substi-tuted aldehydes, e.g., o-, m- or p-benzaldehyde sulfonic acid or carboxylic acid; partial esters of ethylene/maleic anhydride copolymers; partial esters of methylvinyl ether/
maleic an~ydride copolymers; etc.~ In addition, solid mono-meric acid materials could also be used such as palmitic acid, oxalic acid, sebacic acid, hydrocinnamic acid, meta-~5 nilic acid,- paratoluenesulfonic acid and benzenedisulfonic acid. Other suitable materials are disclosed in U.S. Pa-tents 3,422,075 and 2,635,048.
The pH-lowering layer is usually about ~.3 to about 1.5 mils in thickness and can be located in the receiver portion of the film unit between the support and the image-lOS'~610 receiving layer, on the cover sheet, or anywhere within the film unit as long as the desired function is obtained.

An inert timing or spacer layer coated over the pH-lowering layer may also be used to "time" or control the pH
reduction of the film unit as a function of the rate at which the alkali diffuses through the inert spacer layer.
Timing layers can also be used effectively to isolate devel-opment restrainers in a layer adjacent the image-receiving layer wherein restrainers will be released after alkali breakdown of the timing layer. Examples of such timing layers include gelatin, polyvinyl alcohol or any of those disclosed in U.S. Patent 3,455,686. The timmng layer is also effective in evening out the various reacti~n rates ~èr a wide range of temperatures, e.g., premature pH reduction is prevented when i~ibition is effected at temperatures above room temperature, for example, at 95 to 100F. The ; timing layer is usually about 0.1 to about 0.7 mil in thick-ness. Especially good results are obtained when the timing layer comprises a hydrolyzable polymer or a mixture of such ~ 20 polymers which are slowly hydrolyzed by the processing i ' composition. Examples of su~h hydrolyzable polymers include polyvinyl acetate, po~lyami~e~,~ cellulose esters, etc.
; The ~lkal ne processing composition employed in this ; invention can be conventional aqueous solutions of an alka-line material, e.g., sodium hydroxide, sodium carbonate or an amine such as diethylamine, preferably possess~ng~-a pH
in exc~ss of 12, and preferably contains a developing agent as described previously. The solution also preferably contains a viscosity-încreasing compound such as a high-mole-cular-weight polymer, e.g., a water-soluble ether inert to ~ ^ -1(~5'~6~0 alkaline solutions such as hydroxyethyl cellulose or alkali metal salts of carboxymethyl cellulose such as sodium carboxy-methyl cellulose. A concentration of viscosity-increasing compound of about l to about 5% by weight of the processing solution is preferred which will impart thereto a viscosity of about lO0 cps. to about 200,000 cps.
The alkaline processing composition can also con-tain a desensitizing agent such as methylene blue, nitro-substituted heterocyclic compoun*s, 4,~'~bipyridinium salts, etc., to insure that the photosensitive element is not fur-ther exposed after it is removed from the camera for pro-cessing.
While the alkaline processing composition can be employed in a rupturable container, as described previously, to facilitate conveniently the introduction of processing composition into the film unit, other means of discharging processing composition within the film unit could also be employed. For example, processing solution can be interjected by communicating members similar to hypodermic syringes which are attached either to a camera or camera cartridge, as described in U.S. Patent 3,352,674.
In certain embodiments of our invention, and espe-cially with integral format film units, an opacifying agent can be employed in the processing composition in our inven-tion. Examples of opacifying agents include carbon b~ck, - barium sulfate, zinc oxide, barium stearate, silver flake, silicates, alumina, zirconium oxide, zirconium acetyl ace-tate, sodium zirconium sulfate, ka~lin, mica, titanium di-oxide, organic dyes such a9 the nigrosines, or mixtures there-of ~n ~dely varyin~ a~ount~ de~pe~d~n~ upon t~e degree of ~ - 28 -105;~0 opacity desired. In general, the concentration of opaci-fying agent should be sufficient to prevent further expo-sure of the film unit's silver halide emulsion or emulsions by ambient actinic radiation through the layer of process-ing composition, either by direct exposure through a supportor by light piping from the edge of the element. For example, aarbon black or titanium dioxide will generally provide sufficient opacity when they are present in the processing solution in an amount of from about S to 40% by weight.
After the processing solution and opacifying agent have been distributed into the film unit, processing may take place out of the camera in the presence of actinic radiation in ' view of the fact that the silver halide emulsion or emulsions , of the laminate are appropriately protected by incident ra~
diation, at one major surface by the opaque processing com-position and at the remaining major surface by the alkaline solution-permeable opaque layer. In certain embodiments, ballasted indicator dyes or dye precursors can be incorpo~
r,a~d in a layer on the exposure side of the photosensitive layers; the indicator dye is preferably transparent during exposure and becomes opaque when contacted with the process-ing composition. Opaque binding tapes can also be used to prevent edge leakage of actinic radiation incident on the silver halide emulsion.

- 28a-105;~610 When titanium dioxide or other white pigments are employed as the opacifying agent it may also be desirable to employ in cooperative relationship therewith a pH-sensi-tive opacifying dye such as a phthalein dye. Such dyes are light-absorbing or colored at the pH at which image formation is effected and colorless or not light-absorbing at a lower pH. Other details concerning these opacifying dyes are described in French Patent 2,026,927.
The alkaline solution-permeable, substantially opaque, light-reflective layer in the integral negative re-ceiver film units of our invention can generally comprise any opacifier dispersed in a binder as long as it has the desired properties. Particularly desirable are white light-reflective layers since they would be esthetically pleasing backgrounds on which to view a transferred dye image and would also possess the optical properties desired for re-flection of incident radiation. Suitable opacifying agents include titanium dioxide, barium sulfate, zinc oxide, barium stearate, silver flake, silicates, alumina, sirconium oxide, zirconium acetyl acetate, sodium zirconium sulfate, kaolin, mica, or mixtures thereof in widely varying amounts depend-ing upon the degree of opacity desired. The opacifying agents may ~e dispersed in any binder such as an alkal~ma~
solution-permeable polymeric matrix such as, for example, gelatin, or polyvin~l alcohol. Brightening agents such as the stibenes, coumarins, triazines and the oxaxoles can also be added to the light~reflective layer, if desired. When it is desired to increase the opacifying capacity of the light-re~lective layer, dark-colored opacifying agents may be added to it, e.g., carbon black, nigrosine dyes, etc. An-other technique to increase the opacifying capacity of the lOS~ O

light-reflective layer is to employ a separate opaque layer underneath it comprising, e.g., carbon black, nigrosine dyes, e1:c., dispersed in an alkaline solution-permeable polymeric matrix such as, for example, gelatin, or polyvinyl alcohol.
Such an opaque layer would generally have a density of at least 4 and preferably greater than 7 and would be substan-tially opaque to actinic radiation. The opaque layer may also be combined with a developer scaven~er layer if one is present. The light-reflective and opaque layers are ganer~l~y l to 6 mils in thickness, although they can be varied de-pending upon the opacifying agent employed, the degree of opacity desired, etc~
The supports of the film elements of this invention can be any material as long as it does not deleteriously affect the photographic properties of layers thereon and is substantially dimen~ionally stable. Typical useful supports, include cellulose nitrate film, cellulose acetate fi~m, poly-(vinyl acetal) film, polystyrene film, poly(ethyleneterephtha~ -latë3 film, polycarbonate film, poly-~-olefins such as poly-ethylene and p~lypropylene film, and relatedr^films or resin-ous materials, as well as glass. In those embodiments where the support is transparent, it is usually about 2 to 6 mils in thickness and may contain an ultraviolet absorber if desired.
The support of the integral negative recèiver film assemblies and the cover sheet used with these assemblies of this invention can be any of the materials mentioned above for the support. If desired, an ultraviolet-absorbing ma-; terial can be employed in the support or cover sheet.
The photosensitive substances used in this invention , lOSf~610 are preferably silver halide compositions and can comprise silver chloride, silver bromide, silver bromoiodide, silver chlorobromoiodide and the like, or mixtures thereof. The emulsions may be coarse- or fine-grain and can be prepared b~ any of the well-known procedures, e.g., single-jet emul-sions, double-jet emulsions, such as Lippmann emulsions, ammoniacal emulsions, thiocyanate or thioether ripened emul-sions such as those described in U.S. Patents 2,~22,264, 3,320,069, and 3,271,157. Surface-image emulsions can be used or internal-image emulsions can be used such as those described in U.S. Patents 2,592,250, 3,206,313, and 3,447, 927. The emulsions may be re~ular-grain emulsions such as the type described in Klein and Moisar, J. Phot. Sci., vol.
12, No. 5, Sept.~Oct., 1964, pp. 242-251. If desired, mix-tures of surface-and internal-image emulsions can be used as described in Luckey et al, U.S. Patent 2,996,382.
Negative-type emulsions can be used or direct-posi-tive emulsions can be used such as those described in U.S.
Patents 2,184,013, 2,541,472, 3,367,778, 3,501,307, 2,563, 785, 2,456,953, and 2,861,~85 and British Patent 723,019.
~n still another embodiment, the intramolecular nucleophilic displacement compounds can be coated in a layer in an alkali-permeable binder Dn a support to pro~ide what is referred to as a receiver element. The receiver element can be proeessed by positioning it in interfacial contact with a photographic silver halide element in the presence of an alkaline solution and a silver halide developer. In those areas where oxidized developer diffuses to the receiver layer, the nucleophilic displacement compound will be oxidized, and i~ it contains a dye moiety it will provide a permanent image ~05;~610 dye record in the areas corresponding to silver halide development. The remainder of the dye can be removed from the element, for example, by washing, after intramolecular nucleophilic displacement. With proper sélection of the image dye-providing moieties, a black-and-white image can be obtained. Also, if the nucleophilic compound contains a tanning agent as the photographically useful moiety, it is possible to obtain a tanned image record in areas where silver halide development does not take place, i.e., a posi-tive image record if a negative emulsion is used.
In this application, certain groups are identified with reference to the periodic table. The reference table ~;
is located on pp. 400-1 of the Handbook of Chemistry and Physics, 39th Ed., Chemical Rubber Publishing Co.
15, The photographic elements, as described above, generally comprise at least one layer containing photographic recording material, such as silver halide, having associated therewith an immobile compound. The term "associated there~
with" is a term of art in the photographic industry and -generally refers to said immobile compound in alkaline-perme-able relationship with said photographic recording material.
The respective materials can be coated in the same layers or separate layers, as long as they are effectively associated and isolated to provide for the desired reactions before a substantial amount of the intermediate reactant products diffuse into adjacent photographic record~ng layers, etc.

The invention can be further illustrated by the following examples.

, 105'~10 Example l-A: Preparation of 7-chloroformyl-1-methyl-2,1-benz-isoxazolin-3-one-5-N-methyloctadecyl-carboxamide (lA) O=CCl CH3 ~ , 3 o a) 2-nitrotrimesic aci~ (lB~
To a solution of 40.0 g. (1 mole) of sodium hydroxide in 1000 ml. water are added 64 g. (0.33 mole) of a mixture of nitro-3,5-dimethylbenzoic acids (Chem. Ber. 34, 27, i901).
The yellow solution is brought to boiling and 220 g. potassium permanganate are added in portions as fast as the purple color is discharged. After the permanganate addition, the reaction is refluxed an additional 30 min.~ and then cooled to room temperature. The manqanese dioxide precipitate is removed by suction filtration through a celite pad. The deep green filtrate is made acidic with concentrated hydrochloric acid (200 ml). The aqueous solution is then continuously extracted with ether over night. Evaporation of the dried ether ex-tracts gives 30 g~. of pale yellow 2-nitrotrimesic acid, M.P. 290C. dec.
b) 5,7-dicarboxy-2,1-benzisoxazolin-3-one ~lC) A solution of 2.0 g. of lC in 5 ml. of 1:1 ethanol:
~ water, 2M in sulfuric acid, is electrolyzed at aontrolled ; potential (E 1/2 vs. SCE, -0.07 volt) using a mercury work-25- ing electrode. After the electrolysis, the yellow solution ~- is concentrated under reduced pressure until most of the ethanol has been removed. The precipitate which has formed is collected and washed with cold water. The yield of lC is 1.0 g. The crude material which turns yellow on standing is .~

10526~0 used directly in the next step.
c) l-methyl-5,7-dicarboxy-2,1-benzisoxazolin-3-one (lD~' Crude lC is dissolved in a slight excess of aqueous sGdium carbonate solution and treated with a 10~ excess of dimethylsulfate. The reaction is warmed on a steam bath under nitrogen with swirling until the solution becomes homo-geneous. The warm reaction mixture is immediately made acidic with concentrated sulfuric acid and allowed to cool.
The precipitate which forms on cooling is collected, dried and used directly in the next step. Mass spectrum, m/e 237 (m+).

d) 7-carboxy-1-methyl-2,1-benzisoxazolin-3-one-5-N= ~ ;
methyl-octadecylcarboxamide (lE) The above product lD i8 slurried in an excess of ~;
neat thionyl chloride and boiled under reflux for 2 hrs.
During this time all thé solid goes into solution, giving a clear yellow reaction ~ixture. The excess thionyl chloride is removed under reduced pressure, leaving 5,7-bis~chloro-formyl~ methyl-2,1-benzisoxazolin-3-one (lE) as a yellow ~' 20 oil which solidifie~.
The bis-acid chloride (lE) is immediately dissolved in tetrahydrofuran and treated with 4 equivalents of N-methyloctadecylamine dissolved in tetrahydrofuran. The reaction is stirred under nitrogen at room temperature for 15 min. The precipitated N-methyloctadecylamine hydrochlor-ide is removed by filtratLon and the tetrahydrofuran filtrate is concentrated under reduced pressure, giving the bis-amide l-methyl-2,1-benz}soxaz~lin-3-one-5,7-bis(N-methyloctadecyl-carboxamide) (lF~ which is used directly.
` 30 A 10% solution of lF in warm ethanol is treated with an equal volume of 20% aqueous potassium hydroxide solution under a good nitrogen atmosphere. The yellow reaction mixture is stirred under nitrogen for 15 min. and then made acidic with concentrated hydrochloric ec~d. The white precipitate is col~ected and washed well with water. The white solid is treated with tetrahydroîuran and the insol-u~le N-methyloctadecylamine hydrochloride is removed by filtration. The tetrahydrofuran filtrate is dried over an~ydrous calcium sulfate and concentrated under reduced pressure. The solid residue is recrystallized from ethanol-petroleum ether to give the acid-amide lG as a white solid, M.P. 135-136C; mass spectrum, m/e 502 (m+).
e) 7-chloroformyl-1-methyl-2,1-benzisoxazolin-3-one-5-N-methyloctadecylcarboxamide (lA) A solution of acid-amide lG in excess neat thionyl chloride is boiled under reflux for 2 hr. The excesssthionyl is chloride is removed under reduced pressure, leaving the de-sired acid chloride (lA) as a yellow solid.
Example l-B: Preparation of Compound I
Step ~: A solution of 1.72 g. (0.01 mole~ of ~-aminoben-zenesulfonamide in 10 ml. of 3N aqueous HCl (0.03 mole) is , cooled in an ice bath. A precipitate forms. A solution of 0.7 g. (0.01 mole-+S of sodium nitrite in 5 ml of water pre- -viously cooled in ice is then added slowly with stirring.
All of the precipitate dissolves to a very pale yellow solu-tion. The mixture is allowed to stand in ice for about 10 min. Then a co~]ed solution of 1.92 g. (0.01 mole) of N-ethyl-N-(2-methylaminoethyl)-_-toluidine in 1 ml. of acetic - acid is added slowly with stirring. After the addition, the dark red mixture is stirred in ice for sevexal minutes.
Excess sodium bicarbonate is then added slowly to the reaction and the orange solid is collected and washed with water.

: ', ` . :

10526~0 The crude product is separated into fast-1~and slow-moving fxactions by column chromatogrRphy, using silica gel. The slow-moving fraction is collected and used in Step 2.

Step 2: The acid chloride compound of Example l-A
(0.78 g., 0.00149 mole) is dissolved in 75 ml. of tetra-hydrofuran, and 0.55 g. (0.00149 mole) of the purified azo dye of 9tep 1 and 0.38 g. (0.003 mole) of N,N-diisopropyl-ethylamine is added. The mixture is stirred at room tempera-ture for 3 hrs. At the end of this period, a clear orange solution is obtained. The solution is concentrated to a small volume. The concentrate is applied to a column of silica gel and eluted with acetonitrile to yield 1.0 g. of orange-colored Compound I.
Example 2: Preparation of Compound II
Step 1: Compound 2-A and N,N'-dimethylethylenediamine are reacted in the same manner as described in Step 1, Example 4.
Compound 2-A is as follows:

CH37O- ~ N=N ~ SO2Cl .' O
St~p 2: To a slurry of 1.18 g. (0.00284 mole) of the ':
yellow dye HCl of Step 1 in 75 ml. of tetrahydrofuran is added 0.588 g.~ (0.00568 mole) of anpydrous sodium carbonate followed ~y about 5 ml. of water. The mixture is stirred for a few minutes until all of the material has dissolved, and 1.47 g. (0.00284 mole) of the acid chloride lA of Bxample l-A in 50 ml. of tetrahydrofuraa are added dropwise. After the addition, the reaction is stirred at room temperature for 30 min. and then anhydrous hydrogen chloride is passed in until the mixture becomes acidic. The solution is decanted from some insoluble salts and concentrated on a rotary evap-orator. The residue is dissolved in dichloromethane and applied to a dry column o~ silica gel. Upon elution with a 1:1 mixture of acetone and ethyl acetate, a yellow band is collected and concentrated. The yield of Compound II is 1.5 g.
Example 3: Preparation of Compound III
Step 1: A solution of 9.64 g. (0.02 mole) of Compound 3-A in 75 ml. tetrahydxofuran is mixed with 5.04 g. (0.05 mole) of N,N-dimethyl-1,3-propanediamine and 7.74 g. (0.06 mole) of diisopropylaminoethylamine. A mild exotherm resùlts, yielding magenta solution and a gummy precipitate. The mix-ture is heated in an oil bath for 1 hr., cooled and filtered.
The re~idue is washed with tetrahydrofuran. The washings and filtrate are combined and concentrated to a purple syrup.
Compound 3-A is as follows:

1l ~O-C--O--CH2 -CH3 ~ ~LS02Cl Compound 3A, 3-44-hydroxy-8-methylsulfonamidonaphthylazo)ben-zenesulfonyl chloride, can be prepared in the following ---manner. The product of the reaction of 5-amino-1-naphthol and methanesulfonyl chloride is dissolved in alkali and pre-cipitated with acid. The resulting 5-methylsulfonamido-1-- 25 naphthol is coupled with diazotized metanilic acid. The pro-duct of the coupling reac~ion is treated with ethyl chloro-105~610 formate to block the free hydroxyl group and then it is reacted with a mixture of thionyl chloride and dimethyl-formamide to yield the desired Compound 3A.
6tep 2: The syrup from Step 1 is warmed gently at re- ~-flux for 1 hr. with 15 g. of ethyl chloroformate and~l25.ml.
of tetrahydrofuran. Then 5.2 g. (0.04 mole) of N,N-diiso-propylethylamine are added and the mixture is refluxed gently for 1 additional hour. The reaction mixture is con-centrated to a syrup and chromatographed on a silica gel column, using acetone to elute front-running material which - crystallizes.
Step 3: The product of Step 2 (1.50 g.) and 1.50 g. of potassium hydroxide pellets are refluxed for 2 hrs. in a mixture of 60 ml. methanol and 15 ml.n~ater. An additional

4.5 g. of potassium hydroxide are added and gentle refluxing is continued for 2 hrs. At the end of this time the methanol is distilled off, the residue i8 diluted to 100 ml. with water, and an additional 4.0 g. potassium hydroxide are added to make about a 10% solution. The mixture is heated overnight on an oil bath at reflux. After cooling, the reac-tion mixture is slowly acidified with concentrated HCl followed by 5% HCl until the magenta solution turns orange, . .
- giving a precipitate oflfine orange needles. After standing :
for 30 min., the crystals age collected and dried, yielding 1.15 g. pf product.
- Step 4: To a slurry of 0.990 g. (0.00187 mole) of the product of Step 3 in 50 ml. of tetrahydrofuran is added 0.396 g. (0.00324 mole) of anhydrous sodium carbon~te, followed by about 2 ml. of water. ~hen all the material has dissolved, a solution of 0.974 g. tO.00787 mole) of the . , .

~05Z610 acid chloride lA of Example l-A in 35 ml. of tetrahydro-furan is added dropwise. After stirring at room temperature for about 30 min., the mixture is made acidic with anhydrous hydrogen chloride. The solution is concentrated on a rotary evaporator and the residue is dissolved in dichloromethane.
The solution is chromatographed on a column of silica gel.
The eluted product is Compound III.
- Example 4: Preparation of Compound IV
Step 1: To a stirred solution at room temperature of 39~0 g. (0.44 mole) of N,N'-dimethylethylenediamine and 5.68 g. (0.044 mole) of N,N-diisopropylethylamine in tetrahydro-furan are added 17.8 g. (0.0417 mole) of Compound 4-A in por-tions over a period of 5 min. After stirring for 30 min. at room temperature, the mixture is filtered and the filtrate is concentrated to a syrup. The syrup is triturated in three 250-ml. portions of a 5:1 mixture of ether and ligroine (B.P. 35-55C.). The residual syrup is treated with 500 ml.
of a 2% aqueous HCl solution to yield a yellow crystalline product which is cooled to 0C. with st~rring, filtered and dried. The yield of product is 13.3 g.
Compound 4-A is:

Il ~CC6H5 ' ~ IN
~ S02Cl `:
' ., - ~, :

` ~05;~10 Ste~ 2: The product of Step 1 is reacted with the acid chloride lA of Example l-A in the manner of Step 2 of Example 2.
Step 3: To a solution of 1.0 g. (0.0012 mole) Qf the product of Step 2 in 50 ml. acetone is added 0.5 g. pyridine followed by 0.17 g. (0.0012 mole) of benzoyl chloride. The mixture is stirred for 30 min. and concentrated under re-duced pressure. The residue is dissolved in dichloromethane, applied to a column of silica gel and eluted with a mixture of 25:75 ethyl acetate and dichloromethane. The yield is 1.0 g. of Compound IV.
Example 5: Preparation of Compound V
Step 1: Compound 3-A is reacted with N,N'-dimethylethyl-enediamine according to the procedure of Step 1 ~f Example 4.
Step 2: The product of Step 1 above is reacted with the acid chloride product of Example 1-A in the manner of Step 2 of Ex~ 2.
Step 3: To a solu~ion of 1.23 g. (0.00127 mole) of the product of Step 2 is added 0.5 g. pyridine followed by 0.178 ;; 20 g. (0.00127 mole) of benzoyl chloride. The mixture is stirred for 30 min. and concentrated under reduced pressure. The residue is dissolved in aichloromethane, applied to a column of silica gel and eluted with a mixture of 25:75 ethyl acetate and dichloromethane. The yield of Compound V is 0.92 g.
Example 6: Preparation of Compound VI
Step 1: Compound 6-A is r~acted with N,N'-dimethyl-ethylenediamine as described in Step 1 of Example 4 followed by Steps 2 and 3 of Example 4.
Compound 6-A is:

lOS~f~10 ~H
~ `:
~ NHSO2 ~

02CH3 5(~2F ,-Compound 6-A, 3-[5-hydroxy-8-(2-methylsulfonyl-g-nitrophenyl-azo)naphthylsulfamoyl]benzenesulfonyl fluouide, is prepared by coupling diazotized 2-methylsulfonyl-4-nitroaniline with

5-(3-fluorosulfonylphenylsulfonamido)-1-naphthol, made by reacting 5-amino-1-naphthol with 3-~hlorosulfonylbenzenesul-fonyl fluoride.
Example 7:
A photographic element is prepared by coating on a cellulose acetate film support a layer containing a gelatinous negative silver halide (0.8 micron bromide) e~ulsion at 158 mg. silver/ft.2 a~d 183 mg. gelati~jft.2,1-phenyl-3-pyrazoli-done at 15 mg./ft.2, Compound I at 50 mg./ft.2 dissolved in I diethyl lauramide at 50 mg./ft.2.
The photographic element is exposed to a graduated-d~nsity test object and processed at room temperature with an a~ueous solution comprising 70 g./l. potassium hydroxide, 40 g./l. potassium bromide, 3~ g./l hydroxyethyl cellulose, and ; water to 1 liter, while in contact with a mordanted receiver.
Upon separation of the photographic negative element from the mordanted receiver, a well-defined positive yellow dye image is obtained in the receiver.
Example 8:
The procedure of Exam~le 7 i`s repeate~ exce~t 5Q mg.

105;~610 Compound II are used in preparing the photographic element in place of Compound I. In addition, 7 mg./ft.2 of 5-(2-cyanoethylthio)-l-phenyltetrazole dissolved in tricresyl phosphate at 21 mg./ft.2 are incorporated into the emulsion layer. A well-defined positive dye image is obtained in the receiver sheet.
Example 9:
The procedure of Example 8 is repeated except Compound II is replaced with 38 mg./ft.2 Compound III dis-solved in 38 mg./ft.2 diethyl lauramide. Upon separation of - the receiver sheet from the negative photographic element, a well-defined magenta dye image is obtained in the receiver.
Example 10:
... .
A photographic element is prepared as follows:
~ 1~ transparent film support;
1 2) layer containing a red-sensitive negative silver halide emulstion at 158 mg. silver/ft.2 (0.4 micron AgBr), gelatin at 183 mg./ft.2, Compound III at 38 ; mg./ft2, dissolved in diethyl lauramide at 38 mg./ft2, 1-phenyl-3-pyrazolidone at 15 mg./ft.2 and 5-(2-cyanoethylthio)-1-phenyltetrazole at 7 mg./
ft.2 dissolved in tricresyl phosphate at 21 mg./ft.2;
3~ layer containing gelatin at lS0 mg./ft.2, 2,5-di-sec-dodecyl hydroquinone at 70 mg./ft.2 dissolved in diethyl lauramide at 28 mg./ft.2 and a yellow filter dye at 100 mg./ft.2;
4) layer containing a blue-sensitive negative silver halide emulsion at 158 mg. Ag/ft.2 ~0,4 micron AgBr), gelatin at 183 mg./ft.2, Compound II at 50 mg./ft.2 dissolved in diethyl lauramide at 50 mg./ft.2, 1-phenyl-3-pyrazolidone at 15 mg./ft.2, and 5-(2-~05;~6~0 cyanoethylthio)-l-phenyltetrazole at 7 mg./ft.2 diseolved in tricr~syl phosphate at 21 mg./ft.2;
5) layer containing gelatin at 82 mg./ft.2.
The negative photographic element is exposed to a m~llticolor, graduated-density test object and processed as described in Example 7. Upon separation of the negative photographic element from the receiver sheet, well-defined positive image records are obtained in the photographic element exhibiting color separation.
Example 11:
:
A multicolor photographic element is prepared by coating a photographic film support with the following layers in ~rder from the support:
1) layer containing a red-sensitvve negative-silver halide emulsion ~1.2 ~ average grainAgBr) at 150 mg. silver/ft.2, gelatin at 170 mg./ft.2, Compound VI at 60 mg./ft.2 dissolved in diethyl lauramide at 30 mg./ft.2, 1-phenyl-3-pyrazolidone at 15 mg./ft.2, and 5~(2-cyanoethylthio)-1-phenyltetrazole at 12 mg./
ft.2 dissolved in tricresyi phosphate at 36 mg./ft.2;
2) layer containing gelatin at 70 mg./ft.2 and 2,5-di-sec-dodecyl hydroquinone at 70 mg./ft.2 diseolved in diethyl lauramide at 23 mg./ft.2;
3) layer containmng a green-sensitive negative silver halide emulsion (1.2 ~ average grain AgBr) at 150 ; mg. siluer/ft.2, gelatin at 170 mg./ft.2, Compound V at 45 mg./ft.2 dissolved in diethyl lauramide at 23 mg./ft.2~ 1-phenyl-3-pyrazolidone at 15 mg./ft.2, and 5-C2-cyan~et~y~lthl'o~ en~ltetraz~le at 12 mg./
mg./ft.2 d~s~olved ~n t~cres~l phos~Rate at 36 mg./
i - 43 ~

105z6~
ft.2;
4) layer containing gelatin at 70 mg./ft.2, 2,S-di-seP-dodecyl hydroquinone at 70 mg./ft.2 dissolved in diethyl lauramide at 23 mg./ft.2, and Carey Lea S silver at 17 mg./ft.2;
5) layer containing a blue-sensitive negative silver halide emulsioni~tl.2 ~ average grain AgBr) at 150 mg./ft2, gelatin at 170 mg./ft.2, Compound IV at 70 mg./ft2 dissolved in diethyl lauramide at 35 mg./
ft.2, 1-phenyl-3-pyrazolidone at 15 mg./ft.2, and 5-(2-cyanoethylthio)-1-phenyltetrazole at 12 mg./
ft.2 dissolved in tricr~syl phosphate at ~6 mg./

6) layer containing gelatin at 50 mg./ft.2.
The photographic element is exposed to a multicolor, graduated-density test object and processed at room tempera-ture with a viscous aqueous solution aomprising S0 g. potas-sium hydroxide and 30 g. hydroxyethyl cellulose/l. of water, while in contact wlth a mordanted receiver comprlsing a poly-ethylene-coated paper support coated with a l~yer containing copolylstyrene--N-benzyl-N,N-dimethyl-N-(3-maleimidopropyl)-ammonium chloride] at 200 mg./ft.2 and gelttin at 200 mg./
ft.2 add overcoated with a layer containing S0 mg./ft.2 gel~t~n.
; 25 Upon separation of the photographic element from the receiver, the receiver is washed, and a well-defined multicolor reproduction of the test object is obtained.
Exampls 12 An integral color trans~er photographic element is prepared by coatlng a tranaparent film support with the ~`
"

, ~. . .
,:

. ~

lOS'~
following layers in order from the support:
1) layer containing the mordant copoly[styrene--N-benzyl-N,N-dimethyl-N-(3-maleimidopropyl)ammonium chloride] at 200 mg./ft.2 and gelatin at 100 mg./
ft.2;
2) layer containing titanium dioxide at 2000 mg./ft.2 and gelatin at 200 mg./ft.2;
3) layer containing carbon at 250 mg./ft.2 and gelatin at 156 mg./ft.2;
~0 4) layer containing a red-sensitive negative silver halide emulsion (1.2 ~ average grain AgBr) at 150 mg. silver/ft.2, gelatin at 170 mg./ft.2, Compound VI at 60 mg./ft.2 dissolved in diethyl lauramide at 30 mg./ft.2, 1-phenyl-3-pyrazolidone at 15 mg./ft.2, ~;
and 5-(2-cyanoethylthio~-1-phenyltetrazole at 12 mg./
ft.2 dissolved in tricresyl phosphate at 36 mg./ft.2;
5) layer containing gelatin at 70 mg./ft.2 and 2,5-di-sec-dodecyl hydroquinone ah 70 mg./ft.2 dissolved in diethyl lauramide at 23 mg./ft.2;
6) layer containing a green-sensitive negative silver halide emulsion (1.2 ~ average grain AgBr) at 150 mg. silver/ft.2 gel~tin at 170 mg./ft.2, Compound V at 45 mg./ft.2 dissolved in diethyl lauramide at 23 mg./ft.2, 1-phenyl-3-pyrazolidone at 15 mg./ft.2, and 5-(2-cyanoethylth~o)-1-phenyltetrazole at 12 mg./
ft.2 dissolved ln tricresyl phosphate at 36 mg./ft.2;

7) layer containing gelatin at 70 mg./ft.2, 2,5-di-sec-dodecyl hydroquinone at 70 mg./ft.2 dissolv~d in diethyl lauramide at 23 mg./ft.2, and Carey Lea silver at 17 mg./ft.2;

.:-:- .

~05;~61(~ .

8) layer containln~ ~ blue-sensitive negative silver hal-ide emulsion (1.2 ~u average grain AgBr) at 150 mg./ft.2, gelatin at 170 mg./ft.2, Compound IV at 70 mg./ft.~ dissolved in diethyl lauramide at 35 mg./ft.2, l-phenyl-3-pyrazolidone at 15 mg./ft.2, and 5-(2-cyano-ethylthio)-l-phenyltetrazole at 12 mg./ft.2 dissolved in tricresyl phosphate at 36 mg./ft.2;

9) layer containing gelatin at 50 ~./ft.2 The photographic element is exposed to a multicolor, graduated-density test object and processed at room temperature by rupturing a pod containing a viscous solution comprising 100 g. potassium hydroxide and 30 g. hydroxyethy~ cellulose/l. of water between the photographic element and an opaque cover sheet.
A~ter a few minutes, a well-defined multicolor repro-duction of the test object is viewed through the transparent support of the photographic element.
Example 13:
The photographic elements can be processed to pro~ide a good positive image in the exposed element by a reversal pro-cess.
A photographic element is prepared by coating the lay-; ers on the support as follows:
1) support;
2) layer containing 40 mg./ft.2 of Compound VII dissolved in 20 mg./ft.2 of diethyl lauramide, 10 g./ft.2 of 5-(2-cyanoethyl-thio)-l-phenyltetrazole dissolved in 30 mg./ft.2 of tricresyl phosphate, and gelatin at 125 mg./ft.2;
3) layer containing a negative silver bromoiodide emulsion coated at 100 mg./ft.2 based on silver and gelatin at 100 mg./ft.2;

4) layer containing gelatin at 50 mg./ft.2.
Compound VII is as follows:
~.
_L~6_ 105'~610 o}i `
",02CH3 H N-N~ N2 S02-NCH2CH2-N-C li3 C~13 C =o (~H3 H37C18-N~

A sample of the photographic element is exposed image-wise to a step wedge and processed in Kodak ~ Developer DK-50 at a pH of 9.0 for 15 min. at 20 C. The element is then washed for 5 min., dried, and exposed to room light. The sample is then brought into interfacial contact wlth an image-receiving element containing a dye mordant with a viscous processing solu-tion inserted between the photographic element and the image-receivlng element. The viscous processing solution has the for-mula: -potassium hydroxide 60 g.
hydroxyethyl cellulose 30 g.
4-hydroxymethyl-4-methyl-1-phenyl-3- 3 g.
pyrazolidone sodium thiosulfate 3 g.
potassium bromide 10 g.
water to 1 liter After 10 min. the elements are separated. The receiver is washed and dried to provide a good negative image. The photo-~ .
sensitive element is washed, bleached, washed, fixed, washed and dried. A good positive cyan dye image is obtained in this ele-ment.
Example 14:
Intermediates can be prepared for use in Example l-B
by the following procedure:

~- ' ~ .
`

105;~610 5,7-dicarboxy-2,1-benzisoxazolin-3-one To a stirred solution of 12.8 g. of nitrotrimesic ac:id (prepared by alkaline potassium permanganate cxidation of nitromesitylene) in 200 ml. of water containing 30 g. of S s~llfuric acid are added 6.5 g. of zinc dust in portions at such a rate so as to maintain a temperature of about 25C.
After the addition, the mixture is stirred for an additional 1 hr. After this time, 200 ml. of ethyl acetate are added and the m xture is rapidly stirred for 15 min. The reaction is then filtered by suction through a pad of filter aid. The organic layer is s~parated, dried and concentrated under re-duced pressure, leaving 9.6 g. of crude product which is used directly in the neXt step.

~ ~ \ CH30 HOOC ~ O ~ CH300C ~

5,7-dicarboxy-2,1-benzisoxazolin-3-one dimethyl ester A slurry of 10.1 g. of 5,7-dicarboxy-2,1-benzisoxa-zolin-3-one in 75 ml. of methanol containing dry hydrogen chloride gas is boiled under reflux overnight. After this time the reaction is cooled to room temperature and the solid is collected and washed with a little methanol to give 9.8 g.
(86%) of 5,7-dicarboxy-2,1-benzisoxazolin-3-one dimethyl ester, m.p. 166-167~ dec.

CH300C H CH300C~ R

CH300C ~ O ~ CH300C ~ O
., O

l-ethyl-5,7-dicarboxy-2,1-benzisoxazolin-3-one dimethyl ester To a solution of 25.1 g. of 5,7-dicarboxy-2,1-:`

105Z6~0 benzisoxazolin-3-one dimethyl ester in 250 ml. of dimethyl-formamide are added 6.9 g. of an~ydrous potassium carbonate, followed by 18 g. of diethyl sulfate. The mixture is stirred and heated to about 100C. until the orange color fades ~
(about 30 min.). The cooled reaction mixture is poured into 1000 ml. of rapidly stirred aqueous sodium bicarbonate sol-ution. The solid is collected and washed well with water and dried. The crude product is recrystallized from 60:40 ethanol:water to give 20.7 g. (74%) of white crystals of 1-ethyl-5,7-dicarboxy-2,1-benzisoxazolin-3-one dimethyl ester;
m.p. 83-84.
Similarly prepared using the appropriate dialkyl sulfate are the following l-substituted 2,1-benzisoxazolin-3-ones:
1-methyl-5,7-dicarboxy-2,1-benzisoxazolin-3-one ~imethyl ester; m.p. 151-152 l-isopropyl-5,7-dicarboxy-2,1-benzisoxaz~lin-3-one dimethyl ester; m.p. 122-124 1-(2-fluoroethyl)-5,7-dicarboxy-2,1-benzisoxa-zolin-3-one dimethyl ester l-ethyl-5,7-dicarboxy-2,1-benzisoxazolin-3-one , :
To a solution of 13.95 g. of 1-ethyl-5,7-dicarboxy-2,1-benzisoxazolin-3-one dimethyl ester in 50 ml. of tetra-hydrofuran are added 125 ml. of methanol. Nitrogen gas is bubbled into the stirred solution for several minutes. A
solution of 6.0 g. of sodium hydroxide in 50 ml. of water is ~` i then added, and the solution is stirred at room temperature with continued nitrogen bubbling for 15 min. The reaction mixture is then made acidic with concentrated hydrochloric acid, followed by the addition of 300 ml. of water. The mix-ture is then extracted with ethyl ac~tate. The extracts are washed with water and dried over anhydrous calcium sulfate and filtered. The solvent is removed under reduced pressure, : - . . .:

1()5'~610 leaving 11.6 g. (93%) of white 1-~thyl-5,7-dicarboxy-2,1-benzisoxazolin-3-one; m.p. 320 dec.
_~7-bis(chloroform~l)-1-ethyl-2,1-benzisoxazolin-3-one A slurry of 10.05 g. of 1-ethyl-5,7-dicarboxy-2,1-benzisoxazolin-3-one in 75 ml. of thionyl chloride contain-ing 5 drops of dimethylformamide is boiled under reflux for 30 min. The clear yellow solution is concentrated under reduced pressure. The residue is treated with benzene and again concentrated to dryness. The resulting yellow oil is used directly in the next step.

7-carboxy-1-ethyl-2,1-benzisoxazolin-3-one-5-N-methylocta-decylearboxamide To a solution of the above bis-acid chloride in 200 ml. of tetrahydrofuran cooled in an ice bath is added drop-wise a solution of 22.6 g. of N-methyloctadecylamine and 9 g. of triethylamine in 100 ml. of tetrahydrofuran. After the addition, the reaction is made acidic with dry hydrogen chloride gas. The precipitated amine hydrochlorides are re-moved by filtration and the filtrate is concentrated under reduced pressure to a solid which is used directly in the next step.
A 10% solution of the above bis-amide in warm ethanol is treated with an equal volume of aqueous sodium hydroxide (3 equivalents) under a good nitrogen atmosphere. The reac-tion mixture is stirred at room temperature under nitrogenfor 15 min. and then made acidic with hydrochloric acid. The ~ white precipitate is collected, washed well with water and - dried. The dried product is then treated with tetrahydro-furan and the insoluble N-methyloctadecylamine hydrochloride is removed by filtrati~n. The tetrahydrofuran filtrate is concentrated under reduced pre~sure. The res~due ~s recrys-- ~Q -~05A~6~0 tallized from ethanolpetroleum ether to give white 7-carboxy-l-ethyl-2,1-benzisoxazolin-3-one-5-N-methyloctadecylcarbox-amide; m.p. 73-75.
Using procedures similar to the above, the following N-substituted 7-carboxy-2,1-benzisoxazolin-3-one-5-N-methyl-octadecylcarboxamides are prepared:

7-carboxy-1-methyl-2,1-benzisoxazolin-3-one-5-N-methyloctadecylcarboxamide 7-carboxy-1-isopropyl-2,1-benzisoxazolin-3-one-5-N-methyloctadecylcarboxamide 7-carboxy-1-(2-fluoroethyl)-2,1-benzisoxazolin-3-one-5-N-methyloctadecylcarboxamide Each of the above acid amides are then reacted sepa-rately by boiling in excess neat thionyl chloride aDntaining a trace of diethyl formamide for 30 min. to 1 hr. The ex-cess thionyl chloride is removed under redu~ed pressure, leaving the desired acid chlorides as solids or oils which are used directly to prepare compounds by the procedure of Example l-B.
Example 15:
Another procedure for preparing compounds of this inven~ion is as follows:
I. Preparation of 7-carboxy-1-methyl-5-octadecyloxy-2,1-benxisoxazolin-3-one A. Dimethylisophthalate A slurry of 36 g. o~ 5-hydroxyisophthalic acid in 100 ml. of methanol containing dry hydrogen chloride gas is boiled under reflux for 20 hr. After this time, the reaction is cooled to room temperature. The solid cake which has formed is broken up and the product is collected and washed with a little cold methanol; m.p. 158-159.
B. Dimethyl-5-hydroxy-2-nitroisophthalate ' , .. . .
.

~OSZ6~0 To a suspension of 60 g. of dimethylisophthalate in 600 ml. of methylene chloride are added 200 ml. of con-centrated nitric acid, and the mixture is rapidly stirred at room temperature for about 45 min. After this time, 300 ml. of ice water are added, followed by 700 ml. of ethyl acetate. The organic layer is separated, washed with two portions of saturated brine, and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure, leaving a sticky solid which is triturated with 100 ml. of warm benzene. The insoluble material is ~ollected and washed with benzene to give 19.5 g. (27%) of white to pale yellow solid, m.p. 183-186.
C. Dimehhyl-2-nitro-5-octadecyloxyisophthalate To a solution of 19.5 g. of dimethyl~5-hydroxy-2-. 15 nitroisophthalate in 150 ml. of dry ethanol are added 8.8 g. of tetramethylguanidine, followed by 29.1 g. of octa-decyliodide. The mixture is refluxed for 16 hr., cooled, and poured into 700 ml. of water. The precipitate is col-lected and washed well with water. The dried crude product is triturated with methanol. The insoluble solid is col-lected, giving 32.6 g. of product, m.p. 65-68, which is used wit~out further purification.
D. 7-carboxy-5-octadecyloxy-2,1-benzisoxazolin-3-one methyl ester 2~ To a solution of 20.4 g. of dimethyl-2-nitro-5-octadecyloxyisophthalate in 100 ml. of methylene chloride and 100 ml. of ether is added a solution of 8 g. of ammo~
nium chloride in 175 ml. of water. The mixture is rapidly stirred and 16 g. of zinc dust are added all at once. The reaction is stirred at room temperature for 16 hr. After this time, the orange mixture is filtered by suction through 105Z6~0 a celite pad. To the orange filtrate are added 100 ml. of dilute hydrochloric acid, and the mi~ture is shaken until the orange color fades to yellow. The yellow organic layer is separated, dried over anhydrous cal¢ium sulfate and fil-S tered. The solvent is removed under reduced pressure. Theremaining residue is dissolved in 125 ml. of hot methanol.
The solution is cooled somewhat and 50 ml. of petroleum ether are added. ,The ~oLution is al~wed t,o cool slowly to -12C ,inlia freezer. The yellow~ solid which has formed -is,collect~ed Land wa~hed w,,ith~ ol,~;
~e,thanpl.~ y!ield: 10,6, gi ,m.~p.~-,89~dec.

~ ~ j . . .
E. 7-carboxy-1-methyl-5-octadecyloxy-2,1-benzisoxazo-lin-3-one methyl ester To a slurry of 1.85 g. of 7-carboxy-5-octadecyloxy-2,1-benzisoxazolin-3-one methyl ester in 30 ml. of dimethyl-formamide is added 0.28 g. of powdered an~ydrous potassium carbonate. The deep red mixture is warmed to about 40C., whereupon all the material goes ihto solution. With stirring and at a temperature of about 40C., 0.63 g. of dimethylsul-fate is added dropwise. The red color is rapidly discharged.
The reaction is then cooled to room temperature and poured into 200 ml. of rapidly stirred ice-cold 1% hydrochloric acid. The precipitate is collected, washed well with water and used directly in the next step.
. `
' F. 7-carboxy-1-methyl-5-octadecyloxy-2,1-benzisoxazo-, ' lin-3-one To a solution of the above crude 7-carboxy-1-methyl-5-octadecyloxy-2,1-benzisoxazolin-3-one methyl ester in 10 ml. of tetrahydrofuran are added 25 ml. of ethanol. Nitrogen is bubbled into the solution for about 15 min. With con-;

105A~6~0 tinued nitrogen bubbling, a solution of 0.4 g. of sodium hydroxide in 5 ml. of water is added. The mixture is rapid-ly~ stirred under nitrogen at room temperature for 15 min., then carefully made acidic with dilute hydrochloric acid anld poured knto 100 ml. of water. The solid is collected and washed with water. The dried solid is recrystallized from benzene, giving 0.5 g. of white to pale yellow solid product; m.p. 137-139.

G. 7-chloroformyl-1-methyl-5-octadecyloxy-2,1-benzi-soxazolin-3-one A mixture of 461 mg. of 7-carboxy-1-methyl-5-octa-decyloxy-2,1-benzisoxazolin-3-one and 25 ml. of thionyl chloride containing 1 drop of dimethylformamide is boiled under reflux for 15 min. The mixture is concentrated under reduced pressure to give the acid chloride as a yellow solid which is used directly.
II. Preparation of Compound VIII

CH ~H
~ 52CH3 502 CII,C;~H

A solution of 7-chloroformyl-1-methyl-5-octadecyloxy-2,1-benzisoxazolin-3-one (prepared from 461 mg. of the acid) in 10 ml. of tetrahydrofuran is added dropwise to a stirred mixture of 712 mg. of dye (prepared as in Example 6, Step 1) :

105'~6~0 ~
and 250 mg. of triethylamine in 20 ml. of tetrahydrofuran.
A~Eter the addition, the reaction is made acidic with dry hydrogen chloride gas and the precipitated amine hydrochlor-ide is removed by filtration. The filtrate is concentrated under reduced pressure and the residue is dissolved in 80:20 ethyl acetate:acetone and filtered through a short column of silica gel. The deep cyan filtrate is concentrated to dryness and the residue is d.i~ssolved in a small amount of methylene chloride. Petroleum ether is slowly added to the methylene chloride solution until no more solid forms. The product is collected to give 615 mg. of green-blue solid with a metallic luster.
Example 16:
Compounds in accordance with this invention which -contain dye precursors such as color couplers or oxichromic compounds can be prepared, such as by the following pro-cedures:
A., Preparation of 2-(N-benzyloxycarbonyl-N-methylamino)-ethane sulfonyl chloride To a solution of 2.47 g. of a,65% aqueous solution of N-methyltaurine sodium salt (0.01 mole) in 25 ml. of water are added 1006 g. of anhydrous sodium carbonate. The solution is rapidly stirred and 1.8 g. of benzyl chloroform-ate are added. The mixture is stirred at room temperature for 1 hr~, after which time the reaction is extracted once ', with ether to remove organic soluble material. The remaining , aqueous solution is concentrated to dryness under reduced , pressure. The dry white solid i5 suspended in 50 ml. of ; dimethylformamide, and with stirring 3 ml. of thionyl chlor-ide are added. The mixture is stirred at room temperature for 30 min., then poured into crushed ice. The aqueous mix-105'~6~0 ture is extracted with ether and the combined ether extracts are back-extracted with two portions of water to remove di-methylformamide. The dried ether extracts are concentrated under reduced pressure to a nearly colorless oil which is S directly pure by NMR and mass spectral analysis.
B. The sulfonyl chloride of part A is then raacted with the following amino compound (the amino compound is readily available from the corresponding nitro compound by catalytic hydrogenation):

CH3 ~ ~
sulfonyl chloride of Part A

OH
~ N-IC ~ fH3 I_SO2(cH2)2-N

H C=O

Compound l~B

C-l. If a releasable coupler is desired, Compound 16B
can be transformed by catalytic hydrogenolysis which removes the benzyloxycarbonyl protecting group. This compound can then be reacted with the acid chloride of Example l-A to pro-vide the compound having a releasable color coupler thereon.
C-2. If an oxichromic moiety is desired on the com-pound, then Compound 16B is reacted with oxidized 2,6-di-chloro-~-amino~henol in an alkaline medium to provide the azomethine dye. This compound containing the azomethine dye can then be subjected to catalytic hydrogenation, reducing lOSZ6~0 the dye forming an oxichromic moiety and also providing concomitant hydrogenolysis of the benzyloxycarbonyl protect-ing function.
This compound containing the oxichromic moiety can then be reacted with the acid chloride of Example l-A to provide a compound having a releasable oxichromic moiety thereon.
The compounds of C-l or C-2 can be coated in a photo-graphic element in association with a silver halide layer.
The compounds are generally coated at levels of about 50 to 150 mg./ft.2 dissolved in 50 to 150 mg./ft2 of a solvent such as diethyl lauramide in a gelatin layer containing 50 ;~
to 200 mg./ft.2 Of silver halide. Exposure and processing of the element as described in Example 12 gives a positive image in the released coupler or oxichromic moiety and a neg~tive image in the unre~eased coupler or oxichromic moiety.
Where the oxichromic moiety diffuses out of the photosensi-tive layers, such as to a receiver layer, a dye image can be observed upon exposure of the element to air wherein the ` 20 positive image appears in the receiver layer and a negative ; image appears in the silver halide layers. Where the coupler diffuses out of the photosensitive layers, such as to an image-receiving layer, the respective positive and negative dye images can be obtained by treating the elements with oxid~zed colour developer such as N-ethyl-N-hydroxyethyl-p-phenylenediam~ne.
Exam~le 17.
In certain preferred embodiments, the benzisoxa-æolone has a ~enzyl group substituted in the l-position and can be made ~ the follo~ng procedure:

: :` . ` :

105;~61~
I. Preparation of 7-chloroformyl-1-benzyl-5-(N,N'-dihexyl-acetamidoxy)-2,1-benzisoxazolin-3-one A. tert-butyl-(3,5-dicarbomethpxy-4-nitrophenoxy)acetate To a solution of 2.55 g. of dimethyl-5-hydroxy-2-S nitroisophthalate (prepared as in Example 15, ~art B) in 25 mL. of acetone is added 0.69 g. of anhydrous potassium car-bonate, followed by 1.95 g. of tert-butylbromoacetate. The mixture is stirred and refluxed for 20 hr. After this time, the cooled reaction mixture is poured with rapid stirring into 200 ml. of ice-cold 1% hydrochloric acid. The solid is collected and washed well with water. Yield 3.4 g.; m.p.
106-108.
B. (3,5-dicarbomethyoxy-4-nitrophenoxy)acetic acid To a solution of 3.28 g. of tert-butyl-(3,5-dicar-bometh~xy-4-nitrophenoxy)acetate in 20 ml. of benzene are added 100 mg. of ~-toluenesulfonic acid monohydrate. The solution is stirred and refluxed for 30 mins. After this time, the reaction is cooled and the precipitate collected.
Yield 2.4 g.; m.p. 151-152.
C. (3,5-dicarbomethQx~-4-nitrophenoxy)acetyl chloride A solution of (3,5-dicarbomethoxy-4-nitrophenoxy) acetic acid in neat thionyl chloride containing a trace of dimethylformamide is boiled under reflux for 30 min. The excess thionyl chloride is removed under reduced pressure, leaving the acid chloride as an oil which is used directly.
D. (3,5-dicarbomethoxy~4-nitrophenoxy)-N,N-dihexyl-acetamide A stirred solution of (3,5-dicarbomethoxy-4-nitro-phenoxy)acetyl chloride in tetrahydrofuran, cooled in an ice bath, is treat~d dropwise ~it~ ~ tetrahydrofuran solu-tion containing 1 equivalent each of dihexylamine and tri-i{~S'~610 ethylamine. After the addition, the precipitated amino hydrochloride is removed by filtration and the tetrahydro-furan filtrate is concentrated under reduced pressure to an oil which is used directly in the next step.
E. (3,5-dicarboxy-4-nitrophenoxy)-N,N-dihexylacetamide A solution of crude (3,5-dicarbomethoxy-4-nitro-phenoxy)-N,N-dihexylacetamide in ethanol is treated with aqueous sodium hydroxide (3 equivalents) at room temperature for 15 min. After this time, the reaction was poured into cold dilute hydrochloric acid. The diacid product which `~
precipitates is collected and washed well with water; m.p.
180-184.

F. [3,5-dicarbo(~-methoxy)benzyloxy-4-nitrophenoxy]-N,N-dihexylacetamide HO~ ~ ~OH ;~

C~H13 ¦ O \C6H13 CB~O ~ CH2O-C ~ -OCH2 ~ OCH3 OCH2CN~ 6 13 To a solution of (3,5-dicarboxy-4-nitrophenoxy)-N,N-dihexylacetamide in dimethylformamide containing two equivalants of triethylamine are added two equivalents of ~-methoxybenzylchloride. The mixture is stirred and heated to about 100C. for 1 hr. After this time, the reaction is cooled to room temperature and poured into ice water. The aqueous mixture is extracted with 2 portions of methylene .

105'~6~0 chloride. The c~mbined extracts are back-extracted with water to removedimethylformamide~ dried over anhydrous cal-cium sulfate, filtered and concentrated under reduced pres-sure. The remaining oil which was not induced to crystal-lize is analyzed by MMR and used directly in the next step.

G. 7-carboxy-1-benzyl-S-(N,N'-dihexylacetamidoxy)-2,1-benzisoxazolin-3-one)-~-methoxybenzyl ester .

CH30~CH20~x~H2o C=o il I C~H13 To a solution of 0.01 mole of [3,5-dicarbo-(~-meth-oxy)benzyloxy-4-nitrophenoxy]-N,N-dihexylacetamide in 25 ml.
of methylene chloride and 25 ml. of ethyl ether is added a solution of 2 g. of ammonium chloride in 40 ml. of water.
The mixture is rapidly stirred and 4 g. of zinc dust are added all at once. The reaction is stirred at room temperature for 3 hr., then filtered by suction through a celite pad. The orange filtrate is shaken with dilute hydrochloric acid un-til the initial orange color fades to y~llow. The organic layer is separated and dried over anhydrous calcium sulfate.
The solvent is removed under reduced pressure, leaving an oil which is used directly.
The above crude oil is dissolved in 40 ml. of dimeth-ylformamide containing 2.1 g. of triethylamine. The deep red solution is warmed with stirring to about 40C. and 1.5 g. of benzyl bromide are added dropwise. The red color is rapidly discharged. The reaction mixture is cooled to room lOS;~610 temperature and poured into 200 ml. Qf water. The aqueous mixture is extracted with~methylene chloride. The combined, dried extracts are concentrated under reduced pressure to an oil. The oil is dissolved in methylene chloride and applied to a column of silica gel. Elution with methylene chloride and collection of the front-running, highly fluorescent com-ponent gives 2.6 g. of the desired product as an oil which will not crystallize.
H. 7-carboxy-1-benzyl-5-(N,N'-dihexylacetamidoxy)-2,1-benzisoxazolin-3-one A solution of 2.6 g. of 7-carboxy-1-benzyl-5-(N,N'-dihexylacetamidoxy)-2,1-benzisoxazolin-3-one-~-methoxybenzyl ester in 30 ml. of benzene containing 200 mg. of p-toluenesul-: fonic acid monohydrate is refluxed for 48 hr. After this time, the reaction is cooled to room temperature and the white precipitate which forms is collected and washed w~th ben-zene to give 500 mg. of product, m.p. 157-159.
I. 7-chloroformyl-1-benzyl-5-(N,N'-dihexylacetamidoxy)-2,1-benzisoxazolin-3-one A solution of 7-carboxy-1-benzyl-5-(N,N'-dihexylacet-amidoxy)-2,1-benzisoxazolin-3-one in neat oxalyl chloride is boiled for 15 min. The excess oxalyl chloride is removed under reduced pressure to give the acid chloride as an oil which is used directly.
II.
The acid chloride of part I-I. is then used in Example l-B to prepare release compounds containing releasable dyes.
The benzisoxazole compounds containing the dyes can be ~sed in photographic elements, which elements are exposed and processed as described in Example 12 to provide image records in the form of the re~ased dye.
, ~OS;~610 Although the invention has been described in consid-erable detail with particular reference to certain preferred embodiments thereof, variations and modifications can be effected within the sp~Fit and ccope of the invention.

.
:.

:, .~:

" ~
, ., .

Claims (72)

We claim:

1. A photographic element comprising a support having thereon at least one alkali-permeable layer contain-ing a silver halide emulsion having associated therewith an immobile compound comprising a diffusible photographically useful moiety which is an image dye-providing material or an antifoggant moiety, a development inhibitor moiety or a development accelerator moiety, said compound containing a) an oxidizable nucleophilic group or a precursor for an oxidizable nucleophilic group and b) an electrophilic cleav-age group, which contains an electrophilic group and a leaving group which can be displaced under alkaline con-ditions by said nucleophilic group, linking said photographi-cally useful moiety to a group which is a ballast rendering said compound immobile under alkaline processing conditions in said element, said nucleophilic group being located in said compound relative to said electrophilic cleavage group to provide for intramolecular nucleophilic displacement of said leaving group from said electrophilic group under alkaline conditions cleaving said photographically useful moiety from said ballast group, said compound upon oxidation of said nucleophilic group having a substantially lower rate of release of said photographically useful moiety in an alkaline medium, and the rate of reaction of said compound with an oxidized silver halide developing agent under alka-line processing conditions being substantially faster than the reaction rate of intramolecular nucleophilic displace-ment under alkaline processing conditions.

2. A photographic element according to Claim 1 wherein said compound contains a hydrolyzable precursor for said nucleophilic group.

3. A photographic element according to Claim 1 wherein said compound contains a hydrolyzable precursor for said nucleophilic group which is present in a benzisoxazo-lone moiety in said compound.

4. A photographic element according to Claim 1 wherein said electrophilic cleavage group comprises a car-bonyl or sulfonyl electrophilic group which is covalently bonded to a carbon atom.

5. A photographic element according to Claim 1 wherein the rate of oxidation of said compound is at least ten times faster than the rate of nucleophilic displacement.

6. A photographic element according to Claim 1 wherein said photographically useful moiety is an image dye.

7. A photographic element according to Claim 6 wherein said electrophilic group comprises a carbonyl group and said nucleophilic group is an hydroxy group or precursor therefor or an hydroxylamine or a precursor therefor.

8. A photographic element according to Claim 1 wherein release of said photographically useful moiety is substantially prevented upon oxidation of said immobile compound.

9. A photographic element comprising a support having thereon at least three separate superposed layers, each containing a silver halide emulsion and each said silver halide emulsion having associated therewith a bal-lasted immobile compound containing an image dye or image-dye precursor, said compounds each being capable of releas-ing a diffusible dye or dye precursor by intramolecular nucleophilic displacement under alkaline conditions and being capable of reacting with an oxidized silver halide developing agent before substantial release of image dye or image-dye precursor occurs to lower substantially the rate of release of said dye or dye precursor.

10. A photographic element according to Claim 9 wherein said silver halide developing agent is a 3-pyrazoli-done compound, a catechol compound or a hydroquinone com-pound.

11. A photographic element according to Claim 9 comprising a silver halide emulsion having associated there-with said immobile compound, wherein said immobile compound has a rate of release of said diffusible dye or image-dye precursor which is less than the rate of reaction with oxidized silver halide developer, but is faster than the rate of substantial fog development in the initially unde-veloped areas.

12. A photographic element according to Claim 9 which further contains a development restrainer which per-mits initial development to take place but substantially represses further development.

13. A photographic element comprising a support and at least one alkali-permeable layer thereon containing a silver halide emulsion and having associated therewith an immobile compound having the formula:

wherein R1 is an acylic or cyclic organic group; R2 and R3 are bivalent organic groups containing from 1-3 atoms in the bivalent linkage; n and m are integers of 1 or 2; Nu is an oxidizable nucleophilic group or a precursor therefor; E is a carbonyl or sulfonyl electrophilic group; Q is a bivalent group providing a mono atom linkage between E and X2 wherein said mono atom is a nonmetallic atom of group VA or VIA of the periodic table in its minus 2 or minus 3 valence state which can be displaced from said electrophilic group by said nucleophilic group; one of X1 or Q-X2 is a ballasting group of a size sufficient to render said compound immobile in an alkaline processing medium in an alkali-permeable layer of the photographic element, and one of X1 or Q-X2 is a dif-fusible photographically useful moiety which is an image dye-providing moiety, an antifoggant moiety, a development inhibitor moiety or a development accelerator moiety, said nucleophilic group being located in said compound relative to said electrophilic group to provide for intramolecular nucleophilic cleavage of Q-X2 from the remainder of the compound under alkaline conditions, said compound upon oxidation of said nucleophilic group having a substantially lower rate of release of said photographically useful group in an alkaline medium, and the rate of reaction of said compound with an oxidized silver halide developing agent under alkaline processing conditions being substantially faster than the reaction rate of intramolecular nucleophilic displacement under alkaline processing conditions.

14. A photographic element according to Claim 13 wherein R1 of said compound is an aromatic ring and n and m are each 1.

15. A photographic element according to Claim 13 wherein Q-X2 of said compound is an image dye or image-dye precursor and E is covalently bonded to a carbon atom.

16. A photographic element according to Claim 13 wherein Nu is a hydrolyzable precursor for said nucleophilic group.

17. A photographic element according to Claim 13 wherein n and m are 1, and R1 is an aromatic ring having electron-withdrawing groups substituted thereon.

18. A photographic element according to Claim 17 wherein X1 is linked to R1 through an electron-withdrawing moiety.

19. A photographic element comprising a support and at least one alkali-permeable layer thereon containing a silver halide emulsion and having associated therewith an immobile compound having the formula:

wherein R1 and R2 are bivalent organic groups containing from 1-2 atoms with the provision that a carbon atom is covalently bonded to E; R4 is an alkyl group or an aryl group; E is an electrophilic group; Q is a bivalent group providing a mono atom linkage between E and X2 wherein said mono atom is a nonmetallic atom of group VA or VIA of the periodic table in its -2 or -3 valence state which can be displaced from said electrophilic group under alkaline conditions by an hydroxylamino nucleophilic group; one of X1 or Q-X2 is a group of a size sufficient to render said compound immobile under alkaline processing conditions in an alkali-permeable layer of the photographic element; one of X1 or Q-X2 is a diffusible image dye-providing moiety or an antifoggant moiety, a development inhibitor moiety or a development accelerator moiety.

20. A photographic element according to Claim 13 wherein Q-X2 is an image dye-providing moiety.

21. A photographic element comprising a support having thereon at least one layer comprising a silver halide emulsion having associated therewith an immobile compound, wherein said immobile compound has the formula:

wherein R4 is an alkyl group or an aryl group; Q is a biva-lent group providing a mono atom linkage between the car-bonyl group and X2 wherein said mono atom is a nonmetallic atom of group VA or VIA of the periodic table in its -2 or -3 valence state which can be displaced from the adjacent carbonyl group in said formula under alkaline conditions by an hydroxylamino nucleophilic group; X1 is a group of a size sufficient to render said compound immobile under alkaline processing conditions in an alkali-permeable layer of the photographic element; and Q-X2 is an image dye-providing moiety or an antifoggant moiety, a development inhibitor moiety or a development accelerator moiety.

22. A photographic element according to Claim 21 wherein Q is an amino group.

23. A photographic element according to Claim 21 wherein Q-X2 is a development inhibitor.

24. A photographic element according to Claim 21 wherein Q-X2 is a dye or dye precursor.

25. A photographic element according to Claim 21 herein X1 is a ballast group having at least 8 carbon atoms therein, Q-X2 is an image dye or dye precursor, Q is an amine group and R4 is an alkyl group.

26. A photographic element according to Claim 21 wherein said immobile compound has the formula:

27. A photographic element according to Claim 21 wherein said immobile compound has the formula:

28. A photographic element according to Claim 21 wherein said immobile compound has the formula:

29. An article of manufacture comprising a support having thereon at least one alkali-permeable layer contain-ing an immobile compound which comprises a) an oxidizable nucleophilic group or a precursor for an oxidizable nucleo-philic group, and b) an electrophilic cleavage group, which contains an electrophilic group and a leaving group which can be displaced under alkaline conditions by said nucleophilic group, linking a diffusible image dye-providing material to a group which is a ballast rendering said compound immobile under alka-line processing conditions in said element, said nucleophilic group being located in said compound relative to said electro-philic cleavage group to provide for intramolecular nucleophilic displacement of said leaving group from said electrophilic group under alkaline conditions cleaving said image dye-providing material from said ballast group, said compound upon oxidation of said nucleophilic group having a substantially lower rate of release of said image dye-providing material in an alkaline medium and the rate of reaction of said compound with an oxi-dized silver halide developing agent under alkaline processing conditions being substantially faster than the reaction rate of intramolecular nucleophilic displacement under alkaline process-ing conditions.

30. An article of manufacture according to Claim 29 comprising at least one layer containing a silver halide emul-sion having associated therewith said immobile compound.

31. An article of manufacture according to Claim 29 wherein the electrophilic cleavage group comprises a carbonyl or sulfonyl group which is covalently bonded to a carbon atom.

32. An article of manufacture according to Claim 29 wherein said image dye-providing material is a dye moiety having solubilizing groups thereon.

33. A photographic element comprising a support having thereon a layer containing a blue-sensitive silver halide emulsion having associated therewith an intramolecu-lar nucleophilic displacement compound which comprises a yellow image dye-providing moiety, a layer containing a green-sensitive silver halide emulsion having associated therewith an intramolecular nucleophilic displacement com-pound which comprises a magenta image dye-providing moiety, and a red-sensitive silver halide emulsion having associated therewith an intramolecular nucleophilic displacement com-pound which comprises a cyan image dye-providing moiety, wherein each of said intramolecular nucleophilic displace-ment compounds is an immobile compound comprising 1) an oxidizable nucleophilic group or a precursor therefor which is capable of reacting with an oxidized silver halide devel-oper and 2) an electrophilic cleavage group, which contains an electrophilic group and a leaving group which can be displaced under alkaline conditions by said nucleophilic group, linking said image-dye moiety to a group which serves as a ballast for said compound, said nucleophilic group being located in said compound relative to said electro-philic cleavage group to provide for intramolecular nucleo-philic displacement of said leaving group from said elec-trophilic group under alkaline conditions cleaving a dif-fusible image dye-providing moiety from said ballast group, said compound upon oxidation of said nucleophilic group having a substantially lower rate of release of said image dye-providing moiety in an alkaline medium and the rate of reaction of said compound with an oxidized silver halide developing agent under alkaline processing conditions being substantially faster than the reaction rate of intramolecu-lar nucleophilic displacement under alkaline processing conditions.

34. A photographic element according to Claim 33 wherein said immobile compounds contain a benzisoxazolone group which provides said oxidizable nucleophilic group.

35. A photographic element according to Claim 33 wherein said nucleophilic group is capable of undergoing a redox reaction with an oxidized pyrazolidone silver halide developing agent to lower substantially the rate of intra-molecular nucleophilic displacement.

36. A photographic element according to Claim 33 wherein said oxidizable nucleophilic group is an hydroxy group or an alkali-labile precursor therefor or an hydrox-ylamine group or an alkali-labile precursor therefor.

37. A photographic element according to Claim 33 wherein said image dye-providing moiety is a dye moiety.

38. A photographic element according to Claim 33 wherein said nucleophilic group and said electrophilic group of each of said compounds are each attached to an aromatic ring and contain from 1-5 atoms between the nucleophilic center of said nucleophilic group and the electrophilic center of said electrophilic group, whereby said compound is capable of forming a ring having from 3-7 atoms therein by intramolecular nucleophilic displacement.

39. A photographic element comprising a support having thereon at least one layer containing a silver halide emulsion having associated therewith an immobile compound which contains a) a hydrolyzable precursor for an oxidizable nucleophilic group and b) an electrophilic cleavage group, which contains an electrophilic group and a leaving group which can be displaced under alkaline conditions by said nucleophilic group, linking a diffusible image dye-providing material to a group which is a ballast rendering said com-pound immobile under alkaline processing conditions in said element, said nucleophilic group being located in said compound relative to said electrophilic cleavage group to provide for intramolecular nucleophilic displacement of said leaving group from said electrophilic group under alkaline conditions cleaving said image dye-providing material from said ballast group, said compound upon oxidation of said nucleophilic group having a substantially lower rate of release of said image dye-providing material in an alkaline medium and the rate of reaction of said compound with an oxidized silver halide developing agent under alkaline processing conditions being substantially faster than the reaction rate of intramolecular nucleophilic displacement under alkaline processing conditions.

40. A photographic element according to Claim 39 wherein said immobile compound contains said hydrolyzable precursor for said nucleophilic group and said precursor is a precursor for an hydroxyamino group and said image dye-providing material is a preformed diffusible dye.

41. A photographic element according to Claim 39 wherein said immobile compound contains a benzisoxazolone group which contains said hydrolyzable precursor for said oxidizable nucleophilic group.

42. In an image-transfer film unit comprising:
a) a photographic element comprising a support having thereon at least one layer containing a silver halide emulsion having associated therewith an immobile image dye-providing mate-rial;
b) an image dye-receiving layer;
c) means containing an alkaline processing solution which is adapted to discharge said solution within said film unit; and d) a silver halide developing agent which is soluble in said alkaline processing solution;
the improvement wherein said film unit contains an immobile com-pound comprising a photographic reagent which is an antifoggant moiety, a development-inhibitor moiety or a development-accelerator moiety or which is said image dye-providing material and said immobile compound contains (i) an oxidizable nucleo-philic group, and (ii) an electrophilic cleavage group, which contains an electrophilic group and a leaving group which can be displaced under alkaline conditions by said nucleophilic group, linking a photographically useful moiety, which is an image dye-providing material or said photographic reagent, to a group which is a ballast rendering said compound immobile under alka-line processing conditions in said element, said nucleophilic group being located in said compound relative to said electro-philic cleavage group to provide for intramolecular nucleophilic displacement of said leaving group from said electrophilic group under alkaline conditions cleaving said photographically useful moiety from said ballast group, said compound upon oxidation of said nucleophilic group having a substantially lower rate of release of said photographically useful moiety in an alkaline medium, and the reaction rate of said compound with an oxidized silver halide developing agent under alkaline processing condi-tions being substantially faster than the reaction rate of intramolecular nucleophilic displacement under alkaline process-ing conditions.

43. An image-transfer film unit comprising:
a) a photographic element comprising a support having thereon at least three layers, each containing a silver halide emulsion having associated therewith an immobile compound which con-tains a photographically useful group and wherein said photo-graphically useful group is an image dye or image-dye precur-sor and said immobile compound contains (i) an oxidizable nucleophilic group or a precursor for an oxidizable nucleo-philic group, and (ii) an electrophilic cleavage group, which contains an electrophilic group and a leaving group which can be displaced under alkaline conditions by said nucleophilic group, linking said photographically useful moiety to a group which is a ballast rendering said compound immobile under alkaline processing conditions in said element, said nucleo-philic group being located in said compound relative to said electrophilic cleavage group to provide for intramolecular nucleophilic displacement Or said leaving group from said electrophilic group under alkaline conditions cleaving said photographically useful moiety from said ballast group, and said compound upon oxidation of said nucleophilic group hav-ing a substantially lower rate of release of said photo-graphically useful moiety in an alkaline medium, and the reaction rate of said compound with an oxidized silver halide developing agent under alkaline processing conditions being substantially faster than the reaction rate of intramolecular nucleophilic displacement under al-kaline processing conditions;
b. an image dye-receiving layer;
c) means containing an alkaline processing solution which is adapted to discharge said solution within said film unit;
and d) a silver halide developing agent which is soluble in said alkaline processing solution.

44. A film unit according to Claim 42 wherein said silver halide developing agent is a 3-pyrazolidone compound, a hydroquinone compound or a catechol compound.

45. A film unit according to Claim 42 wherein said immobile compound contains said precursor for said nucleo-philic group and said photographically useful moiety is an image dye or image-dye precursor.

46. A film unit according to Claim 42 wherein said immobile compound contains a 2,1-benzisoxazolone group which provides said precursor for said oxidizable nucleophilic group.

47. A film unit according to Claim 42 wherein said electrophilic cleavage group comprises a carbonyl group cova-lently bonded to a carbon atom.

48. A film unit according to Claim 42 wherein said photographically useful group is a development restrainer com-prising a phenylmercaptotetrazole.

49. A film unit according to Claim 42 wherein said photographically useful group as an antifoggant moiety, a development-inhibitor moiety or a development-accelerator moiety.

50. A photographic film unit according to Claim 42 wherein said immobile compound comprises a hydrolyzable pre-cursor for said nucleophilic group and said electrophilic group is a carbonyl group linking an image-dye moiety to a group which serves as a ballast for said compound.

51. A film unit comprising:
a) a photographic element comprising a transparent support having thereon, in sequence, i) an image-receiving layer, ii) an opaque alkali-permeable layer and iii) at least one layer containing a silver halide emulsion having associated therewith an immobile compound which contains a diffusible image dye or an image-dye precursor, said compound containing (i) a precursor for an oxidizable nu-cleophilic group and (ii) an electrophilic cleavage group, which contains an electrophilic group and a leaving group which can be displaced under alkaline conditions by said nucleophilic group, linking said image dye or image-dye precursor to a group which is a ballast rendering said compound immobile under alkaline processing conditions in said element, said nucleophilic group being located in said compound relative to said electrophilic cleavage group to provide for intramolecular nucleophilic displace-ment of said leaving group from said electrophilic group under alkaline conditions cleaving said image dye or image-dye precursor from said ballast group, and said compound upon oxidation of said nucleophilic group having a substantially lower rate of release of said image dye or image-dye precursor in an alkaline medium, and the rate of reaction of said compound with an oxidized silver halide developing agent under alkaline processing conditions being substantially faster than the reaction rate of intramolecular nucleophilic displacement under alkaline processing conditions;
b) means containing an alkaline processing composition adapted to discharge said composition within said film unit;
c) a silver halide developing agent which is soluble in said alkaline processing composition; and d) a cover sheet which is superposed or adapted to be super-posed on said photographic element.

52. A film unit according to Claim 51 wherein said immobile compound has the formula:

wherein R2 and R3 are bivalent organic groups containing from 1-2 atoms; R4 is an alkyl group or an aryl group; E is an electrophilic group; Q is a group providing a mono atom link-age between E and X2 wherein said mono atom is a nonmetallic atom of group VA or VIA of the periodic table in its -2 or -3 valence state; one of X1 or Q-X2 is a group of a size to ren-der said compound immobile under alkaline processing condi-tions in an alkali-permeable layer of a photographic element;
one of X1 or Q-X2 is an image dye or image-dye precursor; and n and m are integers of 1 or 2.

53. A film unit according to Claim 51 wherein said precursor for said oxidizable nucleophilic group is a precur-sor for an hydroxylamine group.

54. An image-transfer film unit comprising:
a) a photographic element comprising a support having thereon at least three separate layers, each of which contains a silver halide emulsion having associated therewith an immobile compound which contains an image dye, and said immobile compound contains (i) a precursor for an oxidiz-able nucleophilic group and (ii) an electrophilic cleavage group, which contains an electrophilic group and a leaving group which can be displaced under alkaline conditions by said nucleophilic group, linking said image dye to a group which is a ballast rendering said compound immobile under alkaline processing conditions in said element, said nucleo-philic group being located in said compound relative to said electrophilic cleavage group to provide for intramole-cular nucleophilic displacement of said leaving group from said electrophilic group under alkaline conditions cleav-ing said image dye from said ballast group, and said com-pound upon oxidation of said nucleophilic group having a substantially lower rate of release of said image dye in an alkaline medium, and the rate of reaction of said com-pound with an oxidized silver halide developing agent under alkaline processing conditions being substantially faster than the reaction rate of intramolecular nucleophilic displacement under alkaline processing conditions;
b) an image dye-receiving layer;
c) means containing an alkaline processing solution which is adapted to discharge said solution within said film unit;
and d) a silver halide developing agent which is soluble in said alkaline processing solution.

55. A film unit according to Claim 51 wherein said cover sheet is a transparent film support which is superposed on said photographic element and said alkaline processing solution comprises an opacifying material.

56. An article of manufacture comprising a support having thereon at least one layer containing a silver halide emulsion in an alkali-permeable binder vehicle and having associated therewith an immobile compound comprising:
a) an electrophilic cleavage group, containing an electro-philic group and a leaving group;
b) a photographically useful moiety which is an image dye-providing material or an antifoggant moiety, a develop-ment inhibitor moiety or a development accelerator moiety;
c) a ballast group for immobilizing said compound in an alkali-permeable colloid layer at least under alkaline conditions;
d) an oxidizable nucleophilic group or precursor for an oxi-dizable nucleophilic group which:
(i) is located in said compound where in the un-oxidized form it reacts with said electrophilic cleavage group to displace said leaving group from said electrophilic group under alkaline conditions and (ii) in the oxidized form does not react with the electrophilic cleavage group under alkaline conditions;
e) said photographically useful moiety has been linked to said ballast group through said electrophilic cleavage group; and f) the rate of reaction of said compound with an oxidized silver halide developing agent under alkaline processing conditions being substantially faster than the reaction rate of intramolecular nucleophilic displacement under alkaline processing conditions.

57. An article of manufacture according to Claim 56 comprising at least one layer containing a negative sil-ver halide emulsion having associated therewith said immo-bile compound.

58. An article of manufacture according to Claim 56 wherein said photographically useful group is an image dye-providing material.

59. An image-transfer film unit comprising:
a) a photographic element comprising a support having thereon at least one alkali-permeable layer containing a silver halide emulsion having associated therewith a ballasted compound of the formula:
wherein R1 is an acylic or cyclic organic group; R2 and R3 are bivalent organic groups containing from 1-3 atoms in the bivalent linkage; n and m are integers of 1 or 2;
Nu is a precursor for an oxidizable nucleophilic group;
E is a carbonyl or sulfonyl electrophilic group; Q is a group providing a mono atom linkage between E and X2 where-in said mono atom is a nonmetallic atom of group VA or VIA
of the periodic table in its minus 2 or minus 3 valence state which can be displaced from said electrophilic group by said nucleophilic group; one of X1 or Q-X2 is a ballast-ing group of a size sufficient to render said compound immobile in an alkaline processing medium in an alkali-permeable layer of the photographic element, and one of X1 or Q-X2 is a diffusible image dye-providing moiety, said nucleophilic group being located in said compound relative to said electrophilic group to provide for intramolecular nucleophilic cleavage of Q-X2 from the re-mainder of the compound under alkaline conditions, said compound upon oxidation of said nucleophilic group having a substantially lower rate of release of said image dye-providing moiety in an alkaline medium, and the rate of reaction of said compound with an oxidized silver halide developing agent under alkaline processing conditions being substantially faster than the reaction rate of intramolecular nucleophilic displacement under alkaline processing conditions;
b) an image dye-receiving layer;
c) means containing an alkaline processing solution which is adapted to discharge said solution within said film unit;
and d) a silver halide developing agent which is soluble in said alkaline processing solution.

60. An image-transfer film unit according to Claim 59 wherein Q-X2 is an image dye or image-dye precursor.

61. An image-transfer film unit according to Claim 59 wherein E is covalently bonded to a carbon atom.

62. An image-transfer film unit according to Claim 59 wherein Nu is a hydrolyzable precursor for an hydroxy group or an hydroxylamine group.

63. An image-transfer film unit according to Claim 59 wherein Q-X2 is an image dye-providing material and said film unit contains at least three separate silver halide layers, each of which has a different ballasted compound of said formula associated therewith.

64. An image-transfer film unit according to Claim 59 wherein said silver halide developing agent is a 3-pyra-zolidone compound, a hydroquinone compound or a catecholcompound.

65. An image-transfer film unit comprising:
a) a photographic element comprising a support having thereon at least one alkali-permeable layer containing a negative-working silver halide emulsion having associated therewith a ballasted compound of the formula:

wherein R2 and R3 are bivalent organic groups containing from 1-2 atoms with the provision that a carbon atom is covalently bonded to E; R4 is an alkyl group or an aryl group; E is an electrophilic group; Q is a bivalent group providing a mono atom linkage between E and X2 wherein said mono atom is a nonmetallic atom of group VA or VIA
of the periodic table in its -2 or -3 valence state which can be displaced from said electrophilic group under alka-line conditions by an hydroxylamino nucleophilic group;
one of X1 or Q-X2 is a group of a size sufficient to render said compound immobile under alkaline processing conditions in an alkali-permeable layer of the photographic element; one of X1 or Q-X2 is a diffusible image dye-providing moiety; and n and m are integers of 1 or 2;
b) an image dye-receiving layer;
c) means containing an alkaline processing solution which is adapted to discharge said soluton within said film unit;
and d) a silver halide developing agent which is soluble in said alkaline processing solution.

66. An image-transfer film unit according to Claim 65 wherein E is a carbonyl group.

67. An image-transfer film unit according to Claim 65 wherein E is a carbonyl group and Q is an amino group.

68. An image-transfer film unit according to Claim 65 wherein n and m are 1 and E is a carbonyl or sulfonyl group.

69. An image-transfer film unit according to Claim 65 wherein Q-X2 is an image dye-providing material.

70. An image-transfer film unit comprising:
a) a photographic element comprising a support having thereon at least one alkali-permeable layer containing a silver halide emulsion having associated therewith a ballasted compound of the formula:
wherein Nu is a precursor for an oxidizable hydroxy or hydroxylamino nucleophilic group; E is a carbonyl electro-philic group; R1 is a cyclic organic group containing an aromatic ring with Nu and E attached directly to said aro-matic group and E is located in said compound relative to Nu to provide for electrophilic cleavage of Q-X2 from the remainder of the compound under alkaline conditions; Q is a bivalent group providing a nitrogen atom linkage between E and X2; X1 is a ballasting group of a size sufficient to render said compound immobile in an alkaline processing medium Ln an alkali-permeable layer of the photographic element; and Q-X2 is a diffusible image dye-providing moiety;
b) an image dye-receiving layer;
c) means containing an alkaline processing solution which is adapted to discharge said solution within said film unit;
and d) a silver halide developing agent which is soluble in said alkaline processing solution.

71. An image-transfer film unit according to Claim 70 wherein said aromatic ring of R1 is a benzenoid ring.

72. An image-transfer film unit according to Claim 70 wherein Nu is a precursor for an hydroxylamine nucleophilic group.