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2,410,025
Patented Oct. 29, 1946
“UNITED STATES’ PATENT OFFICE
‘
2,410,025
'
PRODUCTION OF COLORED PHOTOGRAPH“)
>
Béla
PICTURES
Gaspar,
Hollywood,
‘
Calif.,
Chromogen, ' Incorporated,
a
assignor
corporation
to ' '
of
'
~
-
Nevada
No Drawing. Continuation of application Serial
No. 412,341, September 25, 1941, which is a
division of application Serial No. 179,591, De
cember 13, 1937. This application February 7,
1944, Serial No. 521,439. In Great Britain De
cember 14, 1936
(Cl. 95-—6)
24 Claims.
, 1
2
I
Quinoxaline of the following formula:
1 This application is a continuation of my appli- 1 ‘
cation Serial No. 412,341, ?led September 25, 1941,
which is a division of application Serial No. 179,
591, ?led December 13, 1937, now Reissue Patent
22,308.
,
N
"In my earlier patents a process has been de
'
.
Diphenyl-quinoxaline of the ‘following’ formula:
scribed ‘for ‘the, production of dyestuff images
from diffusely dyed silver images. Thus, for ex
ample, according to my United States Letters
Patent No. 2,020,775, dated November 12, 1935, the
production of such dyestu? images is performed
by treating the diffusely dyed silver image with
solutions which destroy the dye locally in the
presence of the metal deposit of the photographic
image. At the same time the silver is partially
10'
or similar compounds of the general formula:
or totally converted into a silver compound. In
dividual cases, in which the destruction of the
dye can be accelerated by the addition of certain
Y
‘of which the formula: ‘
substances, have been described ‘in my. above
mentioned patent.
.
-
a
20
i
.
‘
‘
‘
O71)
It has been found‘ that the effectiveness of the.
dye-destroying solutions described in my United
StatesLetters Patent No. 2,020,775 and of the‘
other‘ dye~destroying baths which were found to ' is a more speci?c example. In this formula X
beapplicable in the process can be accelerated ‘j 25 and Y represent groups like nitrogen, sulfur, oxy
by a great number of substances other than those ‘ ; gen, ,carbonyle C,=0, carbimino C=NI-ll, and the
heretofore known. A large number of ‘the. sub- _,
like. The compounds may be substituted by am
stances added in accordanceiwith this invention - Wino-groups, . oxyqgroups,
alkyl-groups,
my]
enable the treating solutions to work in a much"
groups, or othersubstituents including also sul
more eiiective manner, e. g., in a’ much shorter 30
ionic-groups.
time or in far smaller concentration, than the
‘
‘ ‘
‘ Example
1
products previously proposed as accelerators.
A 1% aqueous solution of hydrochloric acid
Inview of the great effectiveness of the addi- I
which alone will not work satisfactorily on a layer
tions, much smaller amounts of these accelerat
ing substances are sufficient. .In many cases the.‘ 35 diffusely colored by Diamine Fast Pink G (a dye
stu? furnished ,by the I. G. Farbenindustrie Akt.
presence of the accelerating compounds in the
Ges.).may be activated by the addition of 0.002%
ratio of 1:i00,000 is sufficient to multiply the ef
-of 2,3-diamino-phenazine.
Example 2
accelerators, the following may be mentioned:
40, The‘action of a ‘21/2% aqueous solution of hy
2,3-di-amino-phenazine of the’f'ollowing' fore
fectiveness of the dye~destroying solution.
As substances which I have found to be strong
‘ drobromic acid on the dyestu? Heliotrope B
mula:
‘
'
‘
‘
=
(Schultz Farbsto?tabellen, 1931, 7th edition, vol..
N
‘
_,
, 1,' No.‘ 494) may be ‘considerably accelerated by
Of UNI}: ‘
NH:
\N‘
2-oXy-3-amino-phenazine of the following for
Inula:
'
‘the addition of 0.002% of diamino-phenazine.
. Even the addition oi ‘7 parts of diamino-phena
zine to one mill-ion‘parts of a hydrobromic acid
solution of 1.66% strength has a distinct accel
‘ crating treats the ‘local destruction of Helio
.tropeB.
50
V
‘Example 3
For the production of multicolor images a mul
ti-layenmaterial.maybe used having different
dyestuffs incorporated-in layers in which differ
ent color; selection. pictures are recorded. The
2,410,025
3 V
dyestuffs?may be sforexample Diamine‘Pure Blue
chosen for the tests are in most case insoluble '
FF (Schultz loo. ‘cit: ;No. 510), 3361120—‘Light-'if_e‘1-v
azodyestu?s which in themselves are dif?cult to
bleach out. In usingdyestuifs of ‘this ‘sort, the
low 4 GL'extra (Schultz 10c. cit.v No. 308) and
Sirius Ruby 13 (furnished by the I. G. Farbenin
dustrie Akt. Ges).
di?erences are naturally more evident than if
The dye-destroying solution 5 dyestu?s are employed wihch are bleached out
consists of 4% aqueous solution 0_,f_-hydr0b_romic
acid which has been activated by the addition of
in a shorter ‘time-‘in a dyestuff destroying bath
without admixture. In using insoluble dye
stuffs which are di?icultly bleached, the di?erence
0.002% of diamino-phenazine.
'
Example '4
_ tisisdgreat'that, for instance, the thio-carbamide
l0 ‘bath mentioned'injExample 4 which with an ad
A solution containing 70 g. thiocarbamide, 39 g_
hydroquinone, 50 g_ chrome alum’ 5 c‘cmlsulfur'ic
mixture of, for ‘instance, 2,3-diamino-phenaz1ne
destroys the .dyestu?’sjlocaily after 7 or 8 minutes
acid (d:1_85) per liter, with ‘the fadd‘ition'bf .0'2 ' » of treatment shows practically no useful effect if
g. 2,3-diamino-phenazine is used for-treating .ég,
the accelerating substance is omitted, even if the
posed and developed silver halide layers contain- 1-5 "um-e '°f;treatmenti1s doubled'
ing the dyestu? obtained from diazotised orthoMen-non 5111011111’ however’ be, made of the faict
anisidine and resorcinoL A dyestu? image is ob_
tamed after seven minutesrtreating
_
7
that the application of the admixtures has certain
advantages even in the case of easily soluble and
easily bleaching dyestuff, such as a shortening of
20 the time of treatment and thereby a decreaseof
Example .5
A solution containing 74 ‘g. potassium bromide
thg?‘etmnirgtal'fe?e? ‘(in ‘the 'liyer‘ f
d
and 17% com. sulfuric acid '(d=1.84) per liter'is
saturated with 2,3-diphenyl-quinoxaline and then
I‘: ?es‘! b5 *0 ta‘ 'taé'be gum iirtobcomgmlm s
10 ave‘ een. es 8. an ‘foun .0‘ e‘tlse u if“?!
W
contains less than 0.01 g. per liter of this sub-
celera’tors are giver} m the foum’img 11st Whlch
stance. The solution acts‘ on silver images dyed 25 Sh-QWS the'a’ccglera'tmg effect 'obtamed by the1'ad'
with the 'dyestuff obtained from diazotised 4-
dltlm?’ of Vamus *‘iubsmnces to a number °f
amino-l-benzoylamino 3-methoxy-6-methylben-
treatlrig baths used mprodutcmig'dyest’u? images
Z01 and ?maphtd Within 25 minutes or on
fromsilver imagesdyedby six different dyestu?s.
the
TheSe‘dyestu?-s are:
dyestuff obtained from diazotised o-ani- "
'
sidine and resorcinol ‘Within 30 minutes or 30 A.‘Pontamine Sky Blue :6 B (Schultz loc. cit. No.
on the dyestuff obtained from diazotised pnitraniline and ?-naphtol within 60 minutes.
With this dyestu?‘ and ‘with the same treating
bath the same result is obtained if, instead of
5.10:);
B. IChlorantine'Light Green BB Cibar
C. Tu-checht Brillantrot‘2jB Cilba.
D. ‘Benzolight Red v8 :BL (Schultz ‘loc. cit. No.
the 2,3-diphenyl-quinoxaline, the 2,3-dimethyl- 35
quinoxaline, the 2-oxy-‘3-methylquinoxa1ine or
ordinary quinoxaline are used,y,2 :g. of each accelerato'r being used per ‘liter.
Lg
,1
2
>
,
vcit. :No. 706-).
‘
Accelerati
Catalyst ‘I
_
_.
>
c
'
_____ -.
V
+++
A,‘B.
A, B.
-_-_
+++
___.
+++
l1
Methylene-aminovacetonitrileJ____._______________ _-__v___________ _.
.__
v
17
Benzothio~diazolL
2,3 diamino-phenazine“, __________ -.‘ ______ _._ ____________________ __
_._._
A,B.
11,13.
+++
‘
A,B,C.
A, B.
A, 13,0.
'A,'B,C.
A,'B.
—‘—--—-~r
22
Methyl-violettB _____________ __
23
Aummine ________ __
25
S~diphenylethylene-diaminenn
26
27
2,4-diaminodiphenylamine._.
____
Quinizarine sulphonic acid ______________________________________ -_
24 Diacetyl-p-phenylene~diamine.
+++
. A,,B,C.
++++
A,B.
+++
__
28 Sodium indigo sulphomte
29 1,2,4-triaminobenzene-trihydrochloride
30 Tetramethyl-diamino-benzhydr01.__._
A, 13,,(3.
+++
A,B.
A,B.
,A,.B.
A,B.
A,B.
A,B,C.
++
TetramethyLp-diamino-benzophenone ______ _.
‘
32
Tetramethyl-p-phenylene-diamine-hydrochloride.i
.
'33
Tetramethyl-p-‘diamino-diphenyl methane ______ __
._._
B.
A,'B.
A,B.
A,B.
+++
20 2-oxy-3-amino-phenazine.__.
21 N,N’-di(paraamino-phenyl)
31-
A,B,C.
++
+++
+++
+++
++++
'19‘
2,3 dimethyl-quinoxaline.
A,lB.
A,_B.
++
Hydrobenzamide ______ _.__._,__
13' Quinophtalone.___.___
A,'B,C.
A,B.
Ci
A,.B,C.'
++
++++
'9; Diphenyl-thiocarbazona
111 2,2’,4,4’-tetramino-5,5’-dimethyl-diphenylmethane
15 Tetra-ethyl-p-diamino-benzophenone __________ _.
16 Tetra-ethybp-rphdiamino-dipheny1-methane.___-
A, B, o.
~
++++
+
'
++ _
10
12 .Quinizarine..-
t ft
{13:31
++
Alphabenzil-dioxime ______________ __>__>__,_,_v____)______ .s ___________ .i
‘6}; Diacetyl-monoxime
7:, Dibenzylamine_____
‘8 Diphenyl-piperazine
18
D
.
i
3_ BenzophenQne-anil
‘ _
4' Cyanamide... _________ __
5
Diacetyl-monomethnxime
e?ect.
, hydrochlogg acid 1%,
.
VBenzhydrol"
>
:Congo-SkyBlue (Schultzloc. cit.No. 513).
F. :Chlorantine Fast Orange TRL (Schultz loo.
The dyestu?‘s
No
.,
.566).
1~+
A, 13,0.
+-|+++
A, B,C.
I
A, B.
r
3.4 1N-,methyl-fquinolone _____________________________________________ _. Hydrobrloiile acid 5% A, B.
35
:36
'37
.... __
‘
_
. Hydrochr?iacid 11%
A,B.
Acetone-phenylhydrazone __________________________________ __
Acetone-oxime__-_>._-_
\____
+++
-+
A,B.
C.
38
Acridone __________ __‘___., _____ -.> __________________________________ ._
++
A,'B.
39
?-amino-purine sulnhafe
__
++
A,‘B.
.40- Amino-pyrine ___________________________________________________ __
41 Allantoin _________________ __
++
-J—+
A,B,C.
A,B,C.
$2 ,Anthraquinqne-“betasul ho
43 Benzalmethylamine_v__y_y.-_\______ _44 1Diacetyl-o-phenylendiamine_..
‘45 jiBenzthiazylhxdrazine.__
:16 zehlpr??rdiamlnozbenm
47‘ Gym. 'phe yl-carbazide___
48
Anfhrsmuinnna
+++++
+++
+++
‘+++
++++
-. ............................. __
_i_
R
__
++
+++
A,B.
A,B.
A,‘B,C.
A,B.
A,B
A,B.
A,B,C.
I
2,410,025
N0‘
Catalyst.
used .
2,3-diphenyl-quinoxaline; _‘_ _____ _ l.‘ _____ _..'.‘ _____ __' .............. .-
50
l,amino-anthmquinone..__
_
51
2,ammo-anthraquinone____
_ "
A, B.
Lmethyl-Z-pyridona.
Alizarine~red—S___ .
Alizarine-red-agfa_ _
Dibydro-Z-hydrox
_
57
Fuchsine ______________________ __
_
58
Anthraquinone-beta-sulphonic acid _____________________________ __ Sogd?ium hyposulphite
_
‘
A, B.
"
A‘,B.
+++
A, B, O
A, B.
A, B.
A, B. .
—---
'
A.
59
I v
'l‘etramethyl-p-diarnmo benzophenone __________________________ _ . Accelerating effect on
60
Qumizanne sulphonic acid ______________ __.________ -.‘____________ ._
‘
61
Sodium chloride 20%
..--_do ___________________________________________________________ __
.
i
Magnesium
.
A
'
.E.
.
‘
chloride
F.
20% ‘plus hydro-
‘
chloric acid. ‘
.
.
'
.
‘
.
.'
'
++.+
.
Dlrnethylammostyryl dunethyl-thiazol-N-methyhodide ......... __ Hydrochlo{r_1_<|:_ac1dll%. A, B.
63‘ 6,methoXy-pseudocyanin‘e N-ethyl-iodide ________________________ ..
, 64
D;
llilydrochloric acid
plus hydrochloric
‘
i 62
D.
0
“
r
Dyestu?
49
., 53
54
55
56
'
Accelerating c?ect on
hydrochloric acid 11%
+++
A, B.
N-ethyl-6,methoxy-thiocarbocyanine-iodide .... _.
+++
A,B.
65
66
67
68
N —ethyl-benzthioazol-carbocyanine-iodide.
Quinone__'__.__'____;_.___
Benzalaniline____.'__
Hexamethylenetetra
+++
++
+++
+++
A, B.
5,310
C.
A, B.
69
Benzalazine __________ __
+++
70
p-Toluol-sulphinic acid_____
+
71
Benzene-l-sulphonic ?-sulphinic acid. _ ___
+
Naphtalene-l-sulphonic 4-sulphinic acid ______________ __
+
‘ 72
i '73
(3)—nitrostyryl-quinolinium-N—ethyl-ethylsulphonate-
74 g3)—nitrostyryl-benz-thiazol-ethyl-sulphonate
3)—sulpho-styryl-pseudo-thiohydantoine _
‘ 75
. _ 76
Styrylequinolinium-ethyl-sulphonate._.
“ 77
.(4)—dimethylamino-styryl-rhodanine _________
78
A, B.
O.
C
O.
+++
A, B.
+++
A,
A, B.
B.
+++
+++
__
Bis (4-dimethylamino-2-nitro-phenyl) disulphide ________________ _-
‘
A, B.
++
A, B.
+++
A, B.
Q'I'he‘ foregoing list of accelerating compounds
. able catalysts are‘ characterized by the presence
embodies the results obtained with catalysts be
longing to various classes ‘of compounds. It in
cludes, for example,‘ substances of the general
type disclosed in my earlier Patent No.’ 2,020,775,
of a =_CO group‘ or :03 group, these groups being
present in a carbocyclic or heterocyclic nucleus.
See No. 53. If the =00 group appears several
times in such a compound as is the case in quinone
or ‘*qui‘none derivatives the I‘ effectiveness‘ ,"iS
dated November.12,‘1935. ‘In addition, the list 4
especially good. 1 See Nos. 48, 50, 51, 52,158, 42, 66'.
includes compounds of ‘the class of reducible
- ‘Aliphatic compounds with-=COgroups or :08
organic'substances, the reduction products of
groups are also suitable in many cases. ‘See Nos.
which are re-oxidizable during the treatment of
15,. 31. Hereagain several of such groups maybe
a dyed silver image to‘ the original reducible sub
stance which ‘are claimed in application Serial 45 present in the molecule. In? other cases the
effective compounds are‘ characterized by the
No. 179,591, now Reissue Patent 22,308. The
presence of the group =C‘=N—, either in a ring
claims of the present application are directed to
dye destruction baths and processes employing
system (No. 39) or in an open chain... See Nos.
diphenylmethane and triphenyl-methane deriva
2, 3, 5, 6, 11, 36, 37, 43. Compounds of ‘the
quinone-imide type or indophenols belong to this
tives although the general listing of compounds
have been set forth to indicate the comparative 5O group of catalysts._ Also the compounds con
tainingthe —C=N group show in many cases
activity of the various accelerating compounds.
an accelerating effect. A large class of accelera
The quantity of the added catalyst was 0.2%
tors is found in the class of sensitizing or desensi
in the experiments Nos. 1 to 57 and 60 to 69 of
tizing dyestuffs. See,‘for example, Nos. 62, 63, 64,
the list, 0.8% was used'in No. 58 and 0.5% was
used in No. 59. In Nos. 70' to 72, 1% of the addi 55 .73‘to 77. The capacity of accelerating appears
to bein no direct proportion to the sensitizing
tion was used; In Nos. 73 to '77 the quantity vof
properties but on the contrary to be based mainly
the addition was again 0.05%. In many'cases
on the fact that these dyestuifs usually belong to
far smaller quantities of the catalystmay be
oneiof the above-mentioned groups of accelerating
used for practical purposes.
As can be seen, the new catalysts belong to 60 substances. It may be noted that organic sulpho
compounds, compounds containing —-S——S—-;
diiferent chemical groups. They are in most
-—S—.-,_H or —SOzH groups are also suitable ac
cases organic substances which can be easily
celerators. The soluble derivatives of vat dyes are
hydrated or dehydrated. Compounds, the reduc
‘found to be also e?ective as catalysts. The tests
tion products or oxidation products of which are
capable of‘forming areversible redox-system, are 65 described in the'above given list of results are
only examples of suitable catalysts and dyes and
especially suitable. ‘ See, for example, Nos. 26, 33,
may :be regarded as an illustration only, of the
57. Furthermore, organic bases which can be
new :-process without restriction to ‘the dyes,
catalysts ‘or treatingsolutions used in the ex,
easily oxidizedmay be used, See Nos. 29, 32, 44.
.In many cases. the bases themselves are not
especially effective but can be rendered more suit
ablegby the formation of oxidation products by
autoxidation. The ‘oxidation products of such
bases are very suitable catalysts.v Heterocyclic
bases can also Ibeused. ‘ See Nos. 17, 8. In many
casesthecompounds which are found to be suit~
70
amples.
‘WhatIclaimisL
‘
~.
v
.
‘
1 f
.
.
1.‘ In a process of producing a photographic
dyestu? image in a photographic emulsionuni
formly dyed by an‘ azo-dye and also comprising a
metal‘ image, the step of treating said‘hnietal
2,410., 925
8
image with a solution containing an agent which , ..
8.,A treating bath for producing a photographic,
is nondestructive With respect to. the .dyestu?,
dyestuif image in a photographic emulsion uni
but which reacts with the said metal to ‘oxidize
it and substantially simultaneously to form va
a silver image, comprising a substance capable
formly dyed by anazo-dye and also comprising
reducing substance which, destroys said azo—dye
at the points of the metal image, said ,solution
of selectively destroying said vazo-dye by reduc
tion in the presence of said silver image, said
bath also comprising a small amount of :a di
further containing a smalliamount of a diphenyl
methane derivative which vis reducible ‘and the
reduction products thereof are reoxidlzable dur
ing the treatment of the metal image to the
phenylmethane derivative which is reducible dur-V
ing the production of said dyestuifimage. -
9. A treating bath for producing a photographic
dyestuff image in a photographic emulsion uni
formly dyed by an azo-dye and also comprising
a silver image, comprising a substance capable-of
iforming complex silver compounds and which
original diphenylmethane derivative.
2. In a process of producing a photographic
dyestuff image from a silver‘ image uniformly
dyed by an azo-dye, the step of ‘treating said sil
ver image with a solution containing a substance 15 acts to selectively destroy said azo-dye by reduc
capable of selectively destroying said .azo-Idye by
tion in the presence of said silver image ‘and a
small amount of a. diphenylmethane derivative
reduction in the presence of a photographic sil
ver image and comprising a small amount of a
which is reducible during the production of said
reducible diphenylmethane derivative, the .reduc
dyestuif image.
tion products of which are re-oxidizable during 20
the treatment of said silver'image with said solu
tion to the original reducible diphenylmethane
10. A treating bath for producing a photo
graphic dyestuff image in a photographic emul
sion uniformlydyed by anazo-dye and also com
derivative.
prisingva silver image, comprising hydrohalic acid
“
3. In a process of producing a photographic
and a small amount of a diphenylmethane deriva
dyestuif image in a photographic emulsion uni 25 tive which is reducible during the production of
said dyestu?. image. '
'
formly dyed by an a-Zo-dye and also comprising a
silver image, the step of treating said silver image
11. A treating bath for “producing a photo
graphic dyestuff image in a photographicemul
with a solution containing an agent capable of
sion uniformly dyed by an azo-dye and also com
forming complex silver :compo-unds and which
acts to selectively destroy said azo-dye by reduc 30 prising a silver image, comprising thiocarbamide
tion in the presence of said silver image and av '
and
small amount of diphenylmethane derivative
which is reducible and the ‘reduction products
thereof are re-oXidizab-le during the treatment of
the silver image to the original diphenylmethane
derivative which is reducible :during the produc
tion of said dyestuif image.
derivative.
'
-
a small amount of a diphenylmethane
- ‘12, A treating bath for producing ,aphoto
graphic dyestu?image in a photographic emul
sion uniformly .dyed with an .azo-dye and .also
v.
dyestuff image from a silver image uniformly
comprising . a‘ ‘silver, image, _,comprising hydro
chloric acid and a small amount of .a diphenyl
dyed Ibyan azo-dye, the step of treating said silver
image Witha solution comprising hydrohalic acid
methane derivative which is reducible during the
production of the said dyestu? image.
'
4. In a process of producing a photographic
_ 13; .In a process of producing .a dyestuff image
and a small amount of a‘ diphenylmethane deriv
in a, photographic emulsion comprising a silver
ative which is reducible and the reduction -prod-,
ucts thereof are re-oxidizable during the‘ produc
tion of said ,dyestuiT image to the original di
phenylmethane
derivative.
'
1
I
~
image andia uniformly distributed azo-dyestu'fl’,
the .step‘of treating said azo-dyestuff mule pres
45
5. In a process of producing a photographic
‘dyestu-if image from a silver image uniformly
dyed‘ by an azo-dye, the step of treating said sill
ver image with a solution comprising “thiocar
ence of said silver image with thio-car-bamide,
said treatment being carried out in .the presence
of a small amount of a diphenylmethane deriva
tive which is reducible and the reduction products
thereof are re-oxidizable during the production
bamide and a small amount of a diphenylmethane 50
of said dyestu? image to the original diphenyl
derivative which is reducible and the reduction
products thereof are re-oxidizable during 'the
methane derivative.
production of said dyestuff image to the original
‘in 'a photographic emulsion comprising a silver
diphenylmethane
image and a uniformly distributed azo-dyestuff,
derivative.
"
‘
-
14. In a process of producing a dyestu? image .
'
6. In a process of producing a photographic 55 the step of treating said azo-dyestuff'in the pres
dyestuif image from a silver image uniformly I
ence of said silver ‘image with hydrohalic acid,
dyed by an azo-dye, the step of treating said
silver image ‘with a solution comprising hydro
said treatment being carried out in the presence
of a small amount of a diphenylmethane deriva
tive which is reducible and the reduction products
methane derivative which is reducible and the 60 thereof are re-oxidizable during the production
reduction products thereof are re-oxidizable dur
of said dyestuff imageto the original diphenyl
ing the production of said dyestu? image to the
methane derivative.
chloric acid and a small amount of a diphenyl
original diphenylmethane derivative.
15. 'In a process of producing a dyestuif image
in‘ a photographic emulsion comprising a silver
I "7. Atreating bath for producing a photographic
.dyestuff image in a photographic emulsion uni
~'forml_y dyed by an azo-dye and also comprising
aisilver image, comprising a substance which is
‘non-destructive with respect to the dyestuff, but
"reacts with the silver to oxidize ‘it and substan
tially simultaneously to form .a reducing @sub
stance which destroys said azo-‘djye at the points
\Qtwphe ‘sijlv'er image and also comprising a-small
amount of a diphenylmethane derivative which is
reducible'during the production of the dyestuff
limagawn.
_~
._
._
,-
I'"
>-
.
"
..
65
‘image and a uniformly distributed azoédyestuff,
the step of treating said azo-dyestu? in the pres
ence of said silver image-with hydrochloric acid,
said treatment being carried out in the presence
of a small amount of adiphenylmethane deriva
tive which is reducible and the reduction products
thereof are re-oxidizable during the production‘
:Of said dyestuif image to the original diphenylg
fmethane derivative."
,
i
f“ '
_"16.' A treating bath ;for producing apnea;
graphic dyestuff image ‘in a photographic emul;
2,410,025
10
sion uniformly dyed by an azo-dye and also com
prising a silver image, comprising a substance
of diphenylmethane derivatives and triphenyl
methane derivatives.
capable of selectively destroying said azo-dye by
21. In a process of producing a dyestuff image
from a silver image and a uniformly distributed
reduction in the presence of said silver image,
said bath also comprising a small amount of an
organic compound soluble therein and capable of
accelerating the selective dye destructive action
of said substance, said compound being selected
from the group consisting of diphenylmethane
derivatives and triphenylmethane derivatives.
10
1'7. A treating bath for producing a photo
graphic dyestuff image in a photographic emul
sion uniformly dyed by an azo-dye and also com
prising a silver image, comprising hydrohalic acid
and a small amount of an organic compound
soluble in said bath and capable of accelerating
the selective dye destructive action of said hydro
halic acid, said compound being selected from the
group consisting of diphenylmethane derivatives
azo-dyestuif in a photographic emulsion, the step
of treating said azo-dyestuff in the presence of
said silver image with thio-carbamide, said treat
ment being carried out in the presence of a small
amount of an organic compound capable of ac
celerating the selective dye destructive action of
said thiocarbamide, said compound being selected
from the group consisting of diphenylmethane
derivatives and triphenylmethane derivatives.
22. In a process of producing a dyestuif image
from a silver image and a uniformly distributed
azo-dyestuff in a photographic emulsion, the step
of treating said azo-dyestu? in the presence of
said silver image with hydrohalic acid, said treat
ment being carried out in the presence of a small
and triphenylmethane derivatives.
20 amount of an organic compound capable of ac
18. A treating bath for producing a photo
celerating the selective dye destructive action of
graphic dyestuff image in a photographic emul
said hydrohalic acid, said compound being se
sion uniformly dyed by an azo-dye and also com
lected from the group consisting of diphenyl
prising a silver image, comprising thiocarbamide
methane derivatives and triphenylmethane de
and a small amount of an organic compound 25 rivatives.
soluble in said bath and capable of accelerating
23. In a process of producing a dyestu? image
the selective dye destructive action of said thio
from a silver image and a uniformly distributed
carbamide, said compound being selected from
azo-dyestuff in a photographic emulsion, the step
the group consisting of diphenylmethane deriva
of treating said azo-dyestu? in the presence of
tives and triphenylmethane derivatives.
30 said silver image with hydrochloric acid, said
19. A treating bath for producing a photo
graphic dyestuff image in a photographic emul
sion uniformly dyed by an azo-dye and also com
prising a silver image, comprising hydrochloric
acid and a small amount of an organic compound
‘soluble in said bath and capable of accelerating
the selective dye destructive action of said hydro
chloric acid, said compound being selected from
the group consisting of diphenylmethane deriva
tives and triphenylmethane derivatives.
20. In a process of producing a dyestuff image
from a silver image and a uniformly distributed
treatment being carried out in the presence of a
small amount of an organic compound capable of
accelerating the selective dye destructive action
of said hydrochloric acid, said compound being
selected from the group consisting of diphenyl
methane derivatives and triphenylmethane de
rivatives.
24. In a process of producing a dyestuff image
in a photographic emulsion comprising a silver
image and a uniformly distributed azo-dyestu?',
the step of treating said azo-dyestu? in the pres
ence of said silver image with a substance capable
azo-dyestuff in a photographic emulsion, the step
of selectively destroying said azo-dyestuff by re
of treating said azo-dyestuff in the presence of
duction in the presence of a photographic silver
said silver image with a substance capable of se 45 image, said treatment being carried out in the
lectively destroying said azo-dyestuif by reduc
presence of a small amount of a diphenylmethane
tion in the presence of a photographic silver
derivative which is reducible and the reduction
image, said treatment being carried out in the
products thereof are re-oxidizable during the
presence of a small amount of an organic com
pound capable of accelerating the selective dye 50 production of said dyestuff image to the original
diphenylmethane derivative.
destructive action of said substance, said com
BELA GAsPAR.
pound being selected from the group consisting
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