Photographic coupler compositions containing ballasted alcohols and methods

Photographic coupler compositions comprise a magenta dye-forming coupler and an alcohol in an amount sufficient to increase the activity of the dye-forming coupler. The alcohol is of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of (a) unsubstituted alkyl and alkenyl groups, (b) alkyl groups containing one or more substitutents selected from the group consisting of aryl groups, alkenyl groups, halogen atoms, alkoxy groups, alkoxy carbonyl groups and acyloxy groups, (c) unsubstituted aryl groups and (d) aryl groups containing one or more substituents selected from the group consisting of alkyl groups, alkoxy groups, alkoxy carbonyl groups and acyloxy groups; and R.sub.2 and R.sub.3 are individually selected from hydrogen and the group of moieties from which R is selected, provided that the total number of carbon atoms contained in R.sub.1, R.sub.2 and R.sub.3 is at least 10.

FIELD OF THE INVENTION 
The present invention relates to photographic compositions which comprise a 
dye-forming coupler and a ballasted alcohol which increases the activity 
of the dye-forming coupler. The invention also relates to color 
photographic materials including such coupler compositions, methods for 
increasing the activity of dye-forming couplers in color photographic 
developing processes, and methods for the formation of color images, which 
methods employ the novel coupler compositions. 
BACKGROUND OF THE INVENTION 
It is well known in the color photography art that color images are 
produced by a colored dye which is formed by a coupling reaction between 
an oxidized product of an aromatic primary amine color developing agent 
and a coupler. Various types of cyan, magenta and yellow dye-forming 
couplers are well known for use in such coupling reactions. The couplers 
are often used in combination with one or more solvents and/or other 
additives. For example, the Thirtle et al U.S. Pat. No. 2,835,579 
discloses photographic emulsions comprising couplers in combination with 
alkylphenol or acylphenol coupler solvents. Similarly, Japanese Reference 
No. 61-075349 discloses photographic silver halide emulsion layers 
containing a coupler dissolved in a phenolic organic solvent having a high 
boiling point. The Aoki et al U.S. Pat. No. 4,686,177 discloses silver 
halide color photographic materials containing a cyan coupler which may be 
dissolved in an organic solvent. The resulting solution is finely 
dispersed in water or an aqueous binder for incorporation in the 
photographic material. Aoki et al broadly disclose numerous organic 
solvents which may be employed including, among others, alcohols and 
phenols. The Konishiroku Photo Industry European References Nos. 137,722, 
143,570 and 145,342 similarly disclose silver halide color photographic 
materials which include at least one magenta coupler and a non-color 
forming phenolic compound such as a phenolic high-boiling organic solvent. 
Japanese reference No. 81-041098 discloses silver halide color 
photographic light sensitive materials prepared using cyan coupler 
compounds dispersed and emulsified in solvents having a boiling point 
greater than 200.degree. C. and saturated alcohols of the formula ROH 
wherein R is a 9 to 18 carbon containing saturated unbranched aliphatic 
group. 
It is often desirable in color photography to provide the coupler compounds 
with improved coupler activity. As employed herein, the term improved 
coupler activity relates to the improved colorability of a coupler as 
indicated, for example, by the acceleration of the reaction of the coupler 
with the oxidized developer in forming the colored dye and/or by an 
increase in the color density of the resulting colored dye. For example, 
the Sasaki et al U.S. Pat. No. 4,774,166 broadly discloses numerous 
compounds for use as coloration accelerators for couplers which result in 
a reduction in the photographic processing time. Sasaki et al disclose 
that preferred coloration accelerators comprise phenolic compounds, 
oxyalkylene compounds and hydroxy substituted, 5- to 7- membered 
heterocyclic ring compounds. 
Many coupler compositions, however, are disadvantageous in that relatively 
large amounts of a coupler are required to provide satisfactory color 
density, the reaction rate of the coupler with the oxidized developer is 
unacceptably low, the coupler exhibits unacceptably high sensitivity to 
the pH of the developer solution and/or the like. Accordingly, a 
continuing desire exists for coupler compositions of improved activity for 
use in color photographic materials and methods. 
SUMMARY OF THE INVENTION 
Accordingly, it is an object of the present invention to provide novel 
coupler compositions for use in color photography. It is a more specific 
object to provide coupler compositions which exhibit improved coupler 
activity wherein improved coupler activity is indicated by an increased 
color density in a colored dye formed from the coupler composition and/or 
a reduced sensitivity to the pH of the developer solution in the coupler 
reaction to form the colored dye. It is a further object of the present 
invention to provide coupler compositions which exhibit improved coupler 
activity as indicated by an increase in the color density of the dye 
resulting from reaction of the coupler composition, without causing 
significant bathochromic hue shifts in the colored dye. It is a related 
object of the invention to provide methods for increasing the activity of 
coupler compounds in color photography. Additional objects of the 
invention also include the provision of improved silver halide color 
photographic materials and improved methods for the formation of color 
images. 
These and additional objects are provided by the photographic coupler 
compositions of the present invention which comprise a magenta dye-forming 
coupler and an alcohol in an amount sufficient to increase the activity of 
the dye-forming coupler. Specifically, the alcohol is of the formula 
##STR2## 
wherein R.sub.1 is selected from the group consisting of (a) unsubstituted 
alkyl and alkenyl groups, (b) alkyl groups containing one or more 
substitutents selected from the group consisting of aryl groups, alkenyl 
groups, halogen atoms, alkoxy groups, alkoxy carbonyl groups and acyloxy 
groups, (c) unsubstituted aryl groups and (d) aryl groups containing one 
or more substituents selected from the group consisting of alkyl groups, 
alkoxy groups, alkoxy carbonyl groups and acyloxy groups; and R.sub.2 and 
R.sub.3 are individually selected from hydrogen and the group of moieties 
from which R.sub.1 is selected, provided that the total number of carbon 
atoms contained in R.sub.1, R.sub.2 and R.sub.3 is at least 10. 
It has been discovered that the alcohol employed in the coupler 
compositions of the present invention provides the magenta dye-forming 
coupler with increased activity as indicated by an increase in the color 
density of the colored dye formed therefrom, particularly without causing 
significant bathochromic hue shifts in the dye, and/or by reducing the 
sensitivity of the coupler compound to the pH of the developer solution in 
the formation of the colored dye. Thus, the alcohol is employed in 
combination with the magenta dye-forming coupler in order to increase the 
dye-forming coupler's activity. The coupler compositions of the present 
invention are therefore suitable for use in improved silver halide color 
photographic materials and in improved methods for the formation of color 
images. 
These and additional advantages will be more fully apparent in view of the 
following detailed description.

DETAILED DESCRIPTION 
The photographic coupler compositions of the present invention comprise a 
dye-forming coupler, preferably a magenta dye-forming coupler, and an 
alcohol in an amount sufficient to increase the activity of the 
dye-forming coupler. An increase in the activity of the dye-forming 
coupler is evidenced by an improved color density of the colored dye 
formed from the coupler, particularly without causing significant 
bathochromic hue shifts in the colored dye, and/or by a reduction in the 
sensitivity of the dye-forming reaction of the coupler to the pH of the 
developer solution. The increased activity exhibited by the coupler 
compositions of the present invention allows reductions in the amounts of 
coupler compounds which are employed in photographic materials and/or 
provides developed color images of improved quality. 
The alcohols which are employed in the coupler compositions of the present 
invention are generally described as ballasted alcohols and may be 
employed either as solvents for the coupler compounds and/or as 
non-solvent additives. It is important that the alcohols contain 
sufficient ballast to minimize their volatility and water solubility. 
Alcohols suitable for use in the coupler compositions of the present 
invention are of the formula 
##STR3## 
wherein R.sub.1 is selected from the group consisting of (a) unsubstituted 
alkyl and alkenyl groups, (b) alkyl groups containing one or more 
substitutents selected from the group consisting of aryl groups, alkenyl 
groups, halogen atoms, alkoxy groups, alkoxy carbonyl groups and acyloxy 
groups, (c) unsubstituted aryl groups and (d) aryl groups containing one 
or more substituents selected from the group consisting of alkyl groups, 
alkoxy groups, alkoxy carbonyl groups and acyloxy groups; and R.sub.2 and 
R.sub.3 are individually selected from hydrogen and the group of moieties 
from which R.sub.1 is selected, provided that the total number of carbon 
atoms contained in R.sub.1, R.sub.2 and R.sub.3 is at least 10. 
Preferably, the total number of carbon atoms contained in R.sub.1, R.sub.2 
and R.sub.3 is from 10 to about 30. 
In a preferred embodiment, R.sub.1 is a substituted or unsubstituted alkyl 
group or a substituted or unsubstituted alkenyl group. In additionally 
preferred embodiments, at least one of R.sub.2 and R.sub.3 is hydrogen 
and/or at least one of R.sub.2 and R.sub.3 is a substituted or 
unsubstituted alkyl group or a substituted or unsubstituted alkenyl group. 
For example, when R.sub.1 is a straight-chain or branched alkyl group and 
R.sub.2 and R.sub.3 are hydrogen, the alcohol is of the formula C.sub.m 
H.sub.2m+1 --OH, with m preferably being an integer of from 10 to about 
30. When R.sub.1 and R.sub.2 are individually straight-chain or branched 
alkyl groups and R.sub.3 is hydrogen, the alcohol is of the formula 
C.sub.n H.sub.2n+1 CH(C.sub.m H.sub.2m+1)OH, with n+m preferably being in 
the range of from 9 to about 29. When R.sub.1 is a straight-chain or 
branched alkenyl group and R.sub.2 and R.sub.3 are hydrogen, the alcohol 
is of the formula (C.sub.n H.sub.2n+1)CH.dbd.CH(CH.sub.2).sub.m CH.sub.2 
--OH, with n+m preferably being from 7 to about 27. When R.sub.1 is an 
aryl-substituted alkyl group and R.sub.2 and R.sub.3 are hydrogen, the 
alcohol is of the formula (C.sub.6 H.sub.5)C.sub.n H.sub.2n OH, with n 
preferably being from 4 to about 24. In an additional embodiment, R.sub.1 
may be a substituted or unsubstituted aryl group, preferably with at least 
one of R.sub.2 and R.sub.3 being hydrogen. 
Specific examples of suitable ballasted alcohols for use in the coupler 
compositions of the present invention include, but are not limited to, the 
following compounds 
EQU n--C.sub.12 H.sub.25 OH (a-i) 
EQU n--C.sub.16 H.sub.33 OH (a-ii) 
EQU CH.sub.3 CH(OH)(CH.sub.2).sub.9 CH.sub.3 (a-iii) 
EQU CH.sub.3 (CH.sub.2).sub.7 CH.dbd.CH(CH.sub.2).sub.8 OH (a-iv) 
##STR4## 
EQU (CH.sub.3).sub.2 C.dbd.CHCH.sub.2 CH.sub.2 C(CH.sub.3).dbd.CHCH.sub.2 
CH.sub.2 C (CH.sub.3)(OH)CH.dbd.CH.sub.2 (a-vi) 
##STR5## 
As noted above, the ballasted alcohol employed in the coupler compositions 
of the present invention may act as a solvent for the dye-forming coupler. 
One or more additional organic solvents for the coupler compound may also 
be employed in the compositions of the present invention. Generally, 
conventional organic coupler solvents are known in the art and may be 
employed when the ballasted alcohol of the present invention is used in an 
additive amount which is not sufficient to result in a solution of the 
coupler compound. Examples of conventional organic solvents which may be 
used in the present compositions are described in the Examples set forth 
below. 
The ballasted alcohol is employed in the coupler compositions of the 
present invention in an amount sufficient to increase the activity of the 
dye-forming coupler. In most applications, it is preferred that the 
dye-forming coupler and the alcohol are employed in a weight ratio of from 
about 1:0.1 to about 1:10 in order to effect an increase in the activity 
of the dye-forming coupler. 
As noted above, it is preferred that the dye-forming coupler included in 
the present coupler compositions comprises a magenta dye-forming coupler. 
Couplers which form magenta dyes upon reaction with oxidized color 
developing agents are well known in the art and are described in such 
representative patents and publications as: U.S. Pat. Nos. 2,600,788; 
2,369,489; 1,969,479; 2,311,082; 3,061,432; 3,725,067; 4,120,723; 
4,500,630; 2,343,703; 2,311,082; 3,152,896; 3,519,429; 3,062,653; 
2,908,573; 4,774,172; 4,443,536; 3,935,015; 4,540,654; 4,581,326; European 
Patent Applications 284,239; 284,240; 240,852; 170,164; 177,765 and 
"Farbkuppler-eine Literaturubersicht," published in Agfa Mitteilungen, 
Band III, pp. 126-156 (1961), the disclosures of which are incorporated 
herein by reference. 
Preferred magenta dyed-forming couplers comprise pyrazoloazole compounds of 
the general formula 
##STR6## 
when R.sup.4 i s hydrogen, substituted or unsubstituted alkyl, substituted 
or unsubstituted phenyl, substituted or unsubstituted alkoxy, substituted 
or unsubstituted amino or anilino, substituted or unsubstituted acylamino 
or halogen, or a group which links to a polymer, x is hydrogen or a 
coupling-off group and Z is a heterocyclic ring. Particularly preferred 
pyrazoloazole magenta couplers comprise pyrazole or triazole compounds of 
the formulae M-I and M-II and pyrazolobenzimidizoles of formula M-III: 
##STR7## 
wherein each of R.sup.5 and R.sup.6 are individually selected from 
hydrogen, substituted and unsubstituted alkyl, substituted and 
unsubstituted phenyl, substituted and unsubstituted alkoxy, substituted 
and unsubstituted amino or anilino, substituted and unsubstituted 
acylamino and halogens or are a group which links to a polymer. X is 
hydrogen or a coupling-off group. Coupling-off groups are well known to 
those skilled in the photographic art. Generally, such groups determine 
the equivalency of the coupler and modify the reactivity of the coupler. 
Coupling-off groups can also advantageously effect the layer in which the 
coupler is coated or others layers in the photographic material by 
performing, after release from the coupler, such functions as development 
inhibition, bleach acceleration, color correction, development 
acceleration and the like. Representative coupling-off groups include 
halogens (for example, chloro), alkoxy, aryloxy, alkyl thio, aryl thio, 
acyloxy, sulfonamido, carbonamido, arylazo, nitrogen-containing 
heterocyclic groups such as pyrazolyl and imidazolyl, and imido groups 
such as succinimido and hydantoinyl groups. Except for the halogens, these 
groups may be substituted if desired. Coupling-off groups are described in 
further detail in: U.S. Pat. Nos. 2,355,169; 3,227,551; 3,432,521; 
3,476,563; 3,617,291; 3,880,661; 4,052,212 and 4,134,766, and in British 
Patent References Nos. 1,466,728; 1,531,927; 1,533,039; 2,006,755A and 
2,017,704A, the disclosures of which are incorporated herein by reference. 
As is well known in the photographic art, a coupler compound should be 
nondiffusible when incorporated in a photographic element. That is, the 
coupler compound should be of such a molecular size and configuration that 
it will exhibit substantially no diffusion from the layer in which it is 
coated. 
To achieve this result, the total number of carbon atoms contained in 
R.sup.5 and R.sup.6 should be at least 10 or R.sup.5 or R.sup.6 should 
serve as a link to or form part of a polymeric chain. 
In a particularly preferred embodiment of the coupler compositions of the 
present invention, the magenta dye-forming coupler has an in-film 
pH.sub.1/2 value greater than or equal to about 10.0, which is the pH of 
a typical developer solution. The pH.sub.1/2 value is defined as the pH 
of a solution at which half of the coupler molecules are ionized, i.e., 
deprotonated, at the coupling site when a film containing the coupler is 
immersed in the solution. The ballasted alcohols employed in the 
compositions of the present invention have been determined to be 
particularly suitable for improving the activity of such magenta 
dye-forming couplers. 
Suitable magenta dye-forming couplers for use in the present invention 
include, but are not limited to, the following compounds: 
##STR8## 
The photographic coupler compositions according to the present invention 
are employed in color photographic materials in a manner well known in the 
color photographic art. For example, a supporting substrate is coated with 
a silver halide emulsion and the coupler composition of the present 
invention comprising a magenta dye-coupler and a ballasted alcohol in an 
amount sufficient to increase the activity of the dye-forming coupler. The 
photographic material is then imagewise exposed in a manner well known in 
the color photography art followed by development with an aromatic primary 
amine developer. As is well known in the art, the oxidation product of the 
aromatic primary amine developer reacts with the coupler compound to form 
the colored dye images. 
The compositions and methods of the present invention are demonstrated by 
the following Examples in which references are to parts by weight unless 
otherwise specified. Additionally, the following conventional coupler 
solvents were employed in the Examples for comparative purposes: 
EQU mixed tritolyl phosphates (cs-xi) 
EQU dibutyl phthalate (cs-xii) 
EQU N,N-diethyldodecanamide (cs-xiii) 
EQU p-dodecylphenol (cs-xiv) 
EQU 2,4-di-t-pentylphenol (cs-xv) 
EXAMPLE 1 
Coupler compositions comprising emulsion dispersions of coupler compound 
(m-i) set forth above were prepared using the ballasted alcohol (a-iv) 
according to the present invention as a coupler solvent and using 
conventional coupler solvents for comparison purposes as described in 
Table I. Specifically, an oil base was prepared by warming a mixture of 
1.3 g of the coupler compound (m-i), 0.65 g or 1.3 g of the respective 
coupler solvent and 3.9 g of ethyl acetate until dissolution was complete. 
The compositions containing 0.65 g of the coupler solvent had a 1:0.5 
weight ratio of coupler compound to solvent while the compositions which 
contained 1.3 g of coupler solvent had a coupler compound to solvent 
weight ratio of 1:1. Each resulting oil phase was added to an aqueous 
phase consisting of 35.7 g of a 12.5% aqueous gelatin solution, 4.47 g of 
10% Alkanol XC and 28.4 g of water. Each resulting mixture was warmed to 
approximately 45.degree. C. and passed through a colloid mill three times 
to disperse the oil phase in the aqueous phase. The resulting dispersions 
were coated on transparent cellulose acetate butyrate supports at a level 
of approximately 1.5.times.10.sup.-4 moles/ft.sup.2 (93 mg/ft.sup.2) 
together with a silver bromoiodide emulsion containing about 6% iodide, in 
the following format: 
______________________________________ 
Gelatin 250 mg/ft.sup.2 
BVSM Hardener 2% of total gelatin 
Saponin 1.46% 
Gelatin 350 mg/ft.sup.2 
Coupler (m-i) 93 mg/ft.sup.2 
Ag Emulsion 84.2 mgAg/ft.sup.2 
Saponin 1.46% 
______________________________________ 
Support 
______________________________________ 
The resulting hardened films were exposed through a step tablet on a 
sensitometer and then subjected to an E-6 commercial development process 
employing citrazinic acid (CZA) while additional films were subjected to a 
similar development process which did not contain the citrazinic acid. 
After processing, the maximum density (Dmax) value of each film strip was 
measured through a green filter and the spectral absorption maxima 
(.lambda.max) at densities of approximately 1.0 of the films were measured 
on a spectrophotometer. The resulting data is set forth in Table I. 
TABLE I 
______________________________________ 
Coupler: 
Solvent Dmax Dmax 
weight (with (w/out .lambda.max 
Coupler Solvent 
ratio CZA) CZA) (nm) 
______________________________________ 
(a-iv)-invention 
1:0.5 2.65 4.02 553 
(a-iv)-invention 
1:1 3.17 4.13 551 
(cs-xi)-conventional 
1:0.5 1.56 2.93 552 
(cs-xi)-conventional 
1:1 1.55 2.79 550 
(cs-xii)-conventional 
1:0.5 1.86 3.30 552 
(cs-xii)-conventional 
1:1 2.06 3.43 550 
(cs-xv)-conventional 
1:0.5 1.90 3.27 553 
(cs-xv)-conventional 
1:1 2.55 3.73 554 
______________________________________ 
The results set forth in Table I demonstrate that use of the ballasted 
alcohol according to the present invention as a coupler solvent increased 
the activity of the coupler compound, as evidenced by a significantly 
increased maximum color density, Dmax, as compared with the coupler 
compositions which contained conventional coupler solvents. Additionally, 
the results set forth in Table I demonstrate that use of the coupler 
composition according to the present invention employing the ballasted 
alcohol exhibited a smaller degree of undesirable bathochromic hue shift, 
as indicated by .lambda.max, in the composition containing a 1:1 weight 
ratio of coupler to solvent as compared with the use of the conventional 
coupler solvent which provided the closest Dmax, namely, the coupler 
composition employing the conventional coupler solvent (cs-xv). 
EXAMPLE 2 
Coupler compositions comprising emulsion dispersions of magenta coupler 
compound (m-ii) as described above were prepared using various ballasted 
alcohols according to the present invention as coupler solvents and using 
conventional coupler solvents as set forth in Table II. The resulting 
coupler compositions contained a weight ratio of coupler compound to 
coupler solvent of 1:0.5. Specifically, an oil phase was prepared by 
warming a mixture of 3.4 g of the coupler compound (m-ii), 1.7 g of the 
respective coupler solvent and 10.2 g of an auxiliary solvent comprising 
2-(2-butoxyethoxy)ethyl acetate until dissolution was complete. The 
resulting solution was added to an aqueous phase solution containing 18.13 
g of a 12.5% aqueous gelatin solution, 2.7 g of 10% aqueous Alkanol XC and 
2.08 g of water. Each resulting mixture was passed through a colloid mill 
three times to disperse the oil phase and was then chilled, noodled and 
washed for four hours at 40.degree. C. to remove the auxiliary solvent. 
Each dispersed coupler composition was then coated on a cellulose acetate 
butyrate support at a level of 1.5.times.10.sup.-4 moles/ft.sup.2 (108 
mg/ft.sup.2) together with a sensitized silver bromoiodide emulsion 
containing 12% iodide, in the following format: 
______________________________________ 
Gelatin 250 mg/ft.sup.2 
Hardener 1.75% of total gel 
Gelatin 350 mg/ft.sup.2 
Coupler (m-ii) 1.5 .times. 10.sup.-4 
mole/ft.sup.2 
Ag Emulsion 84.2 mg/ft.sup.2 
Tetraazaindine 35 mg/mole Ag 
______________________________________ 
Support 
______________________________________ 
Hardened film strips of the coated supports were exposed through a step 
wedge of a sensitometer (1/25 sec) and subjected to a Kodak 
Flexicolor.RTM. (C-41) color development process Green densities of the 
processed films were read using a densitometer and .lambda.max values were 
measured on a spectrophotometer. The coupler solvents were evaluated in 
two separate coating sets, A and B. The contrast or photographic gamma, 
measured on the straight line portion of the density versus exposure 
curve, and .lambda.max values are set forth in Table II. 
TABLE II 
______________________________________ 
Coupler Solvent Gamma .lambda.max (nm) 
______________________________________ 
Set A: (a-iv)-invention 
2.50 555.3 
(cs-xi)-conventional 
1.60 555.3 
(cs-xii)-conventional 
1.80 555.6 
(cs-xiv)-conventional 
3.08 558.2 
Set B: (a-i)-invention 2.21 556.4 
(a-ii)-invention 
2.08 557.8 
(a-iii)-invention 
2.09 556.5 
(a-iv)-invention 
2.27 556.5 
(a-v)-invention 2.17 557.1 
(a-vi)-invention 
2.09 557.6 
(cs-xi)-conventional 
1.80 556.9 
(cs-xii)-conventional 
1.57 556.3 
______________________________________ 
The results set forth in Table II demonstrate that the coupler compositions 
containing the ballasted alcohols according to the present invention 
provided the photographic materials with substantially larger gamma values 
as compared with the coupler compositions containing conventional coupler 
solvents such as compounds (cs-xi) and (cs-xii). Additionally, unlike the 
conventional phenolic coupler solvent, use of the ballasted alcohols 
according to the present invention produced only small bathochromic hue 
shifts. Thus, the coupler compositions of the present invention are 
particularly useful when it is desirable to improve coupler activity while 
also maintaining dye hue. For example, as demonstrated in Set A, use of 
the ballasted alcohol (a-iv) according to the present invention as 
compared with use of the conventional coupler solvent (cs-xii) increased 
the gamma value from 1.6 to 2.5 while the .lambda.max is the same for both 
compositions. It is also noted that while use of the conventional coupler 
solvent (cs-xiv) provided a large increase in the gamma value, it also 
produced an undesirably large bathochromic hue shift of nearly 3 nm 
relative to the use of other compounds. 
EXAMPLE 3 
Coupler compositions comprising dispersions of the coupler compound (m-iii) 
as set forth above were prepared using a ballasted alcohol according to 
the present invention (a-iv) as a coupler solvent and using various 
conventional coupler solvents. The coupler compound and the respective 
coupler solvent were employed in a weight ratio of 1:1. Specifically, an 
oil phase comprising 0.90 g of the coupler compound (m-iii), 0.90 g of 
coupler solvent and 2.70 g of an auxiliary solvent comprising 
2-(2-butoxyethoxy)ethyl acetate was added to an aqueous phase comprising 
7.20 g of a 12.5% aqueous gelatin solution, 0.90 g of Alkanol XC and 2.40 
g of water. The mixture was passed through a colloid mill to disperse the 
oil phase. Each resulting dispersion was then coated on a transparent 
cellulose acetate butyrate support at a level of 1.0.times.10.sup.-4 
moles/ft.sup.2 (65.7 mg/ft.sup.2) together with 84.2 mg/ft.sup.2 of a 
silver bromoiodide emulsion containing 12% iodide, in the following 
format: 
______________________________________ 
Gelatin 250 mg/ft.sup.2 
Hardener 1.75% of total gel 
Gelatin 350 mg/ft.sup.2 
Coupler (m-iii) 65.7 mg/ft.sup.2 
Coupler Solvent 65.7 mg/ft.sup.2 
Ag Emulsion 84.2 mg/ft.sup.2 
Tetraazaindine 35 mg/mole Ag 
______________________________________ 
Support 
______________________________________ 
Hardened film strips of the coated support were exposed and processed as 
described in Example 2. Gamma values obtained from plots of the status M 
green density versus the exposure and .lambda.max values from absorption 
spectra at a density of approximately 1.0 were determined and are set 
forth in Table III. 
TABLE III 
______________________________________ 
Coupler Solvent Gamma .lambda.max (nm) 
______________________________________ 
(a-iv)-invention 0.92 558.3 
(cs-xi)-conventional 
0.58 556.3 
(cs-xii)-conventional 
0.69 556.2 
(cs-xiv)-conventional 
1.37 569.0 
______________________________________ 
The results set forth in Table III demonstrate that use of the coupler 
composition according to the present invention containing the ballasted 
alcohol compound (a-iv) provides a substantial improvement in gamma value 
relative to use of the conventional coupler compositions containing 
solvents (cs-xi) and (cs-xii), while simultaneously providing only a 
slight increase in .lambda.max. Moreover, while use of a coupler 
composition containing the phenolic coupler solvent (cs-xiv) provided 
significant improvements in gamma value, this composition also provided an 
unacceptably large bathochromic hue shift of 13 nm relative to the other 
compositions. 
EXAMPLE 4 
Coupler compositions comprising emulsion dispersions of the polymeric 
magenta coupler compound (m-iv) as described above and a ballasted alcohol 
according to the present invention as a coupler solvent or various 
conventional coupler solvents were prepared. The coupler compositions 
contained a coupler compound to coupler solvent weight ratio of 1:0.5. 
Specifically, dispersions were prepared by milling 0.3 g of the respective 
coupler solvent and 1.1 g ethyl acetate with 15 ml of a 12.5% aqueous 
gelatin solution, 1.9 ml of 10% aqueous Alkanol XC and 9.1 ml of water. 
Each resulting coupler solvent dispersion was then added to a latex 
dispersion of the polymeric coupler compound (m-iv) in an amount to 
provide the coupler compound to coupler solvent weight ratio of 1:0.5. The 
resulting mixtures were stirred for three hours at 40.degree. C. to permit 
loading of the coupler solvent into the latex. The resulting coupler 
solvent-containing latex dispersions of the polymeric coupler compound 
were then coated on a transparent cellulose acetate butyrate support at a 
level of 1.0.times.10.sup.-4 moles/ft.sup.2 with a sensitized silver 
bromoiodide emulsion containing 12% iodide, in the following format: 
______________________________________ 
Gelatin 250 mg/ft.sup.2 
Hardener 1.75% of total gel 
Gelatin 350 mg/ft.sup.2 
Coupler (m-iv) 1.0 .times. 10.sup.-4 
mole/ft.sup.2 
Coupler Solvent 1:0.5 (w/w) 
Ag Emulsion 84.2 mg/ft.sup.2 
Tetraazaindine 35 mg/mole Ag 
______________________________________ 
Support 
______________________________________ 
Hardened film samples of the coated supports were exposed and processed 
according to the procedures described in Example 2. The status M green 
gamma values were obtained as described in the previous examples and are 
set forth in Table IV. 
TABLE IV 
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Coupler Solvent Gamma 
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(a-iv)-invention 0.96 
(cs-xi)-conventional 
0.67 
(cs-xii)-conventional 
0.86 
(cs-xiii)-conventional 
0.49 
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The results set forth in Table IV demonstrate that the use of the coupler 
composition according to the present invention containing the ballasted 
alcohol as a coupler solvent provided a significantly improved gamma value 
as compared with the use of the coupler compositions containing 
conventional coupler solvents. 
Similar coupler compositions containing additional ballasted alcohols 
according to the present invention were used to prepare color films which 
exhibited similar improvements in gamma values and/or Dmax, with little or 
no significant bathochromic hue shifts in the resulting colored dyes. 
The preceding examples are set forth to illustrate specific embodiments of 
the invention and are not intended to limit the scope of the compositions 
and methods of the present invention. Additional embodiments and 
advantages within the scope of the claimed invention will be apparent to 
one of ordinary skill in the art.