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Патент USA US3061440

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United States Patent
"ice
2
1
Further, the purpurogallin may be substituted by halides,
3,061,430
PHOTOGRAPHIC PROCESS FOR MAKING PRINT
ING PLATES AND LIGHT SENSITIVE NAPH
THOQUINONE THEREFOR
_\
3,061,430
.. Eat‘ented Oct. 30, 1962
'
'
Such substitution products of purpuro
gallin still contain the tropolone system and‘ at least one
free hydroxyl group which can be esteri?ed with the
such as bromine.
naphthoquinone- ( 1,2) -diazide sulfochloride.
Fritz Uhlig, Fritz Eudermann, and Wilhelm Neugebauer,
Wiesbaden-Biebrich, Germany, assiguors, by mesne as:
_ Among the naphthoquinone-(1,2)-diazide sulfochlo
signments, to Azoplate Corporation, Murray Hill, New
Jersey
rides to be used according to the present invention, the
naphthoquinone-( 1,2) -diazide- (2 ) -sulfochloride- ( 5 ) and
No Drawing. Filed Jan. 7, 1960, Ser. No. 935
the naphthoquinone-( 1,2) -diazide- (2 ) -sulfochloride- (4)
Claims priority, application Germany Jan. 14, 1959
10 have proved especially suitable, but the naphthoquinone
39 Claims. (Cl. 96-33)
(1,_2)-diazide-(1)-sulfochl0ride-(5-) and the naphtho
The present invention relates to reproduction layers
qu1gone-(1,2)-diazide-(1)#sulfochloride~(4)
may also be
use .
for printing plates which include at least one light-sensi
In the formulae below, some of thepreferably used
tive ester of a naphthoquinone-(l,2)-diazide sulfonic acid
and an aromatic compound which is substituted with 15 naphthoquinone-(1,2)-diazide sulfonic acid esters are
hydroxyl groups and contains a tropolone system, for
stated under their most probable constitutional, formulae:
example, purpurogallin or its substitution products. The
layers for the printing plates may also, if desired, con
tain alkali soluble resins.
Formula I
It is known to the art to manufacture printing plates 20
one surface of which is coated with a reproduction layer
containing, as light-sensitive substances, esters of naphtho
quinone-(1,2)-diazide sulfonic acids and aromatic hy
droxyl compounds having aromatic rings of six carbon
atoms, such as phenols or naphthols.
.
The light-sensitive esters to be used in the reproduc
tion layers in accordance with the present invention are
prepared by known methods, preferably by reacting
naphthoquinone-(1,2)-diazide sulfonic acid chlorides with
the aromatic component containing the hydroxyl group 30
and the tropolone system in the presence of an acid
binding agent, such as alkali bicarbonate, alkali carbonate
or other weak alkalies or organic bases, preferably terti
Formula II
ary amines such as pyridine or N-ethyl-pipen'dine, gen
erally in homogeneous solutions in solvents, such as 35
dioxane or tetrahydrofurane. In order to avoid forma
tion of a dyestuff, the acid-binding agent must be added
in such quantities only as to render the reaction mixture
neutral or weakly alkaline. In general, the pH value of
the solution should not exceed 8. For separation, the
reaction product is precipitated from the reaction mixture
by the addition of dilute hydrochloric acid, ?ltered by
suction, and dried. In most cases, the sulfonic acid
esters thus obtained can be immediately used for the
preparation of the light-sensitive layer. Alternatively,
45
they may be further purified by dissolving them in di
oxane or another solvent and reprecipitating them by
adding water to the solution.
Among the aromatic components containing hydroxyl
groups and a tropolone system, purpurogallin, which has 50
the following formula
(‘H o OH
110
55
110
has proved to be especially suitable. It is easily syn
thesized by oxidizing pyrogallol, tag. with sodium iodate. 60
By choosing the proper quantity of naphthoquinone
(1,2)-diazide sulfochloride and the corresponding quan
tity of an acid-binding agent for the reaction, one or more
or all of the hydroxyl groups may be esteri?ed. Com
pounds which contain from 1 to 3 ester groups thus hav 65
ing at least one free hydroxyl group, are preferred in the
present invention.
Alternatively, compounds may be prepared in which
prior to the reaction with sulfochloride the tropolone
compounds are partially etheri?ed, e.g. with dimethyl 70
sulfate, diethyl sulfate, or diazo methane. Thus, esters
are obtained which contain also lower alkoxy groups.
3,061,430
3
4
Formula IV
HO
num foil, from which the layer has been removed by the
(I?
developing process, are treated with an about 1 percent
OH
phosphoric acid solution, containing gum arabic, to im
prove the hydrophilic properties. The image areas in
which the unaltered diazo compound remains are inked
up with greasy ink. Thus, printing plates corresponding
HO
0
402
to the original used are obtained which may be set up
in a printing apparatus and used for printing.
Alternatively, the plate may be etched before it is
10 inked with greasy ink, so that clichés are obtained.
The printing plates prepared with the diazo compounds
of the present invention are superior to the printing plates
hitherto used in that they permit very long runs to be
N
II
0
made and, in the unexposed state, they are more stable at
15 higher temperatures, so that the supports provided with
Formula V
the reproduction layers in question have an improved
0
H
?
shelf-life, even under adverse conditions.
-N:
Na:
S0:
|
H0
8,0’
J)
I/
O—
The invention will be further illustrated by reference
to the following speci?c examples:
20
Example I
1.5 parts by weight of the reaction product of 1 mol
purpurogallin and 1 mol of naphthoquinone-(1,2)-di
azide-(2)-sulfonic acid chloride-(5), corresponding to
25 Formula I, are dissolved in 100 parts by volume of ethyl
eneglycol monomethylether, the solution is ?ltered and
then coated onto a mechanically roughened aluminum
foil which may ‘be placed e.g. on a rotating disc. The
(I)
SO:
foil is then dried by means of a current of warm air.
30 For the preparation of a printing plate, the layer side of
the fail is exposed under a master and the exposed layer
is then developed with a one percent trisodium phosphate
N2
solution. In the parts of the layer not struck by light,
the diazo compound remains unchanged. After rinsing
ll
0
For the preparation of the reproduction layers the
above described esters, which are practically water-in
35 the developed layer with Water, it is treated with one
soluble, are dissolved in a suitable organic solvent and
then coated onto a support in a manner known per se.
If desired, they may be used in admixture with an alkali 40
soluble resin. Copolymers of maleic acid anhydride with
styrene, low molecular weight phenol-formaldehyde resin
and cresol formaldehyde resins are preferred for this
purpose.
The amount of the alkali soluble resin added to the
light sensitive diazo esters described above may vary
widely.
For the production of planographic printing
plates ‘lower contents of resins are used, i.e. from about
percent phosphoric acid in order to improve the hydro
philic properties of the support and then inked with
greasy ink. The printing plate thus obtained may be
used for printing in an o?set printing apparatus.
Similar results are obtained on eloxated aluminum foils
and on silicated aluminum foils. The latter are obtained,
e.g. by treating aluminum foils with alkali silicates.
The compound corresponding to Formula I is prepared
as follows:
Twenty-seven parts by weight of naphthoquinone
(1,2)-diazide- (2) -sulfochloride-(5) and 22 parts by
Weight of purpurogallin are dissolved in 400 parts by vol
ume of \dioxane and, while stirring and at room tempera
ture, about 100 parts by volume of a saturated sodium
0.1 to about 1 part by weight, preferably 0.3 to 0.8 part
by weight of resin to 1 part by weight of ester. If the 50 bicarbonate solution are cautiously added over a period
production of plates is intended which can withstand the
of 20 minutes. Part of the reaction product precipitates
acid etching agents used in etching machines for half
at this stage. With agitation, the reaction mixture is then
tone blocks, higher resin contents are used, i.e. from
poured into 100 parts by volume of ice water and hydro
about 1 to about 6 parts, preferably from about 2 to
chloric acid is added until the mixture has become acid
about 4 parts by weight of the resin to 1 part of the
reacting. After 30 minutes, the light-brown monosul
above described esters.
fonic acid ester, which now has completely precipitated,
There may also be ‘used mixtures of the above de
is ?ltered by suction, washed until neutral, and dried.
scribed esters With each other or with other light sensi
The reaction product thus obtained is the 2’-monoester
tive diazo compounds. In general, 1-4 percent solutions
corresponding to Formula I. After recrystallization from
of the preferred purpurogallin esters are used for coating
glacial acetic acid and dioxane, the compound is ob
a support.
tained as an analytically pure light-brown crystalline sub
The supports used are metallic lithographic supports,
stance which, upon heating to temperatures ranging from
e.g. foils or plates of aluminum, copper, zinc, or metal
about 280 to about 330° C., decomposes while slowly
plates consisting of several metal layers, e.g. a base layer
charring. It is easily soluble in dimethyl formamide,
consisting of aluminum and an upper layer consisting of 65 soluble in dioxane, glacial acetic acid and ethyleneglycol
chromium, which are separated from each other by a
monomethylether, but only dif?cultly soluble in ethanol
copper layer. Nonmetallic supports, e.g. plastic ?lms,
special base papers or glass, may also be used.
or methanol.
Example 11
The reproduction layers according to the present inven
In
100
parts
by
volume
of ethyleneglycol monomethyl
tion are photomechanically transformed into printing 70
ether, there is dissolved 1.0 part by weight of the reaction
plates, i.e. the light sensitive layer is exposed to light
product of 1 mol of purpurogallin and 2 mols of naphtho
under an original and then developed with dilute alkaline
solutions, thus removing the areas of the reproduction
quinone-(1,2)-diazide-(2)-sulfonic acid chloride-(5), cor
layer which have been exposed to light. The plate is
responding to Formula II, and 0.5 part by weight of an
then rinsed with water. Then the areas, e.g. the alumi 75 alkali soluble phenol formaldehyde novolak. An alumi
3,061,430
5
6
num foil is coated with this solution and then a printing
weight of calcium chloride, 80 parts by volume of gly
cerine, 80 parts by volume of concentrated hydrochloric
acid, and 250 parts by volume of water. By this treat
ment, the chromium is removed from the non-imaged
plate is prepared following the procedure of Example I.
The diazo compound corresponding to Formula II is
prepared by dissolving in 400 parts by volume of dioxane,
54 parts by weight of naphtl1oquinone-(1,2)-diazide-(2)
sulfonic acid chloride-(.5) and 22 parts by weight of
purpurogallin and then adding, over a period of 30
areas.
The diazo compound corresponding to Formula IV is
prepared as follows:
Twenty-seven parts by weight of naphthoquinone-( 1,2) minutes and while agitating at about 20° C., about 200
diazide-(2)-sulfonic acid chloride-(4) and 22 parts by
parts by volume of saturated sodium bicarbonate solu
tion. The reaction mixture is poured into 100 parts by 10 weight of purpurogallin are dissolved in 400 parts by
volume of dioxane and to this solution there are added,
volume of ice water and hydrochloric acid is added until
over a period of about 20 minutes and while agitating at
the mixture shows a weakly acid react-ion. The precipi
room temperature, I100 parts by volume of a saturated
tating yellow-brown bis-sulfonic acid ester is drawn oil,
sodium bicarbonate solution. While agitating, the re
washed neutral and dried. If crystallized from dioxane,‘
action mixture is poured into 100 parts by volume of ice
the compound is obtained analytically pure in the form of
water and dilute hydrochloric acid is added until a weakly
an olive-yellow substance which, upon heating, decom
acid reaction is obtained. After 30 minutes, precipita
poses at temperatures from about 280° C. to about 330°
tion of the light-brown monoester is complete; it is drawn
C., while slowly charring. It is easily soluble in dimeth
oif, washed until neutral, and dried. For puri?cation,
ylformamide, soluble in warm dioxane, glacial acetic
the compound is dissolved in dioxane and reprecipitated
acid, and ethyleneglycol monomethylether, and hardly
by adding water to the solution. The puri?ed compound
soluble in methanol or ethanol.
is a light-brown ?nely crystalline substance which, upon
The diazo compound corresponding to Formula 111 is
heating in a melting point tube,’ begins to decompose and
prepared analogously to the diazo compound correspond
chars at temperatures ranging from about 280 to about
ing to Formula II by dissolving 54 parts by weight of
naphthoquinone-(1,2)-diazide-(2)-sulfonic acid chloride 25 330° C. It is very easily soluble in dimethylformamide,
dioxane, monomethylether, but almost insoluble in meth
(4) and 22 parts by weight of purpurogallin in 400 parts
anol and ethanol.
by volume of dioxane and then adding, over a period of
Example IV
30 minutes and while agitating at a temperature of about
20° C., about 2100 parts by volume of a saturated sodium
A paper sheet which had been pretreated ‘for the prep
bicarbonate solution. The reaction product is then poured
aration of printing plates, e.g. a paper sheet manufactured
in ice water and hydrochloric acid is added until the
in accordance with the disclosure of US. Patent No.
mixture shows a weakly acid reaction. The precipitate is
2,681,617, is coated with a 2 percent solution in methyl
then ?ltered by suction, washed neutral with water and
glycol of the reaction product of 1 mol of purpurogallin
dried.
with 3 mols of naphthoquinone-(l,2)~diazide-(2)-sulfo
‘For puri?cation, the bis-ester is dissolved in dioxane
nic acid chloride-(5) corresponding to Fonmula V, and
and reprecipitated by adding water to the solution. It
the coated paper sheet is then dried by means of warm
is obtained in the form of a dark-brown crystalline sub
stance Which, upon heating, melts at temperatures rang
ing from about 280 to about 330° C., while slowly
char-ring. It is very easily soluble in ethyleneglycol
monomethylether, dioxane, acetone, glacial acetic acid,
dimethyl formamide, and other organic solvents.
Example III
In 100 parts by volume of ethyleneglycol monomethyl
ether, there are dissolved 4 parts by weight of the reac
tion product of 1 mol of purpurogallin with 1 mol of
naphthoquinone-(1,2)-diazide-(2)-sulfonic acid chloride
air. After exposing the sensitized sheet under a master,
the light-struck areas of the layer, i.e. those areas con
taining the light decomposition product of the original
diazo compound, are removed with an about 2 percent tri
sodium phosphate solution.
The thus developed paper
sheet may be used as a printing plate from which, after
inking with greasy ink, prints can be made.
The diazo compound corresponding to Formula V is
prepared as follows:
Eighty-one parts by weight of naphthoquinone-(1,2)-'
diazide-(2)-sulfonic acid chloride-(5) and 22 parts by
weight of purpurogallin are dissolved in 500 parts by
(4), corresponding to Formula IV, 3 parts by ‘weight of an
volume of dioxane and, over a period of 40 minutes and
alkali soluble phenol formaldehyde novolak and, for im- ,, while agitating at room temperature, 300 parts by vol
proving the visibility of the developed image, 0.5 part by
ume of a saturated sodium bicarbonate solution are
weight of the dyestuif “Methyl Violet” (G. Schultz,
added. While agitating, the reaction mixture is poured
“Farbstofftabellen,” 7th edition, 1931, vol. 1, page 327,
into 100 parts by volume of ice water, and hydrochloric
No. 783); a clean zine plate is coated with this solution.
acid is added until a weakly acid reaction is obtained.
After exposure of the sensitized zinc plate under a master, 55
After
about 40 minutes, the precipitating yellow triester
the light-struck parts of the layer, which contain the light
is ?ltered by suction, washed neutral, and dried. For
decomposition product of the original diazo compound,
puri?cation, the compound is dissolved in dioxane and
are removed by means of a 5 percent aqueous solution of
reprecipitated by adding water to the solution. The com
trisodium phosphate to which 15 percent of ethylene
pound thus obtained is a canary yellow ?nely crystalline
glycol monomethylether had been added. Clichés suit
substance which, upon heating, decomposes at tempera
able for relief and intaglio printing may be prepared in
tures ranging from about 280 to about 330° C., while
a manner known per se by chemically etching the ex
slowly charring. It is easily soluble in dimethyl form
posed areas of the metal plate using a 4 percent solution
amide, soluble in dioxane and ethyleneglycol monometh
of nitric acid.
ylether, but hardly soluble in methanol or ethanol.
Lithographic bimetallic or trimetallic plates may be
analogously coated with the solution of the compound
Example V
corresponding to Formula IV and then developed. Bi
Three
parts
by
weight
of the diazo compound obtained
metallic plates consisting of an aluminum foil with a thin
from 1 mol of purpurogallin and 1 mol of naphthoqui
copper layer thereon are, after development, preferably
etched with a saturated aqueous solution of ferric nitrate 70 none-(1,2)-diazide-(2)-sulfonic acid chloride-(5) corre
sponding to Formula I and 10 parts by weight of a m
whereby the copper is removed in the non-imaged areas.
cresol-formaldehyde resin novolak of the softening point
Trimetallic plates consisting of an aluminum base, an
intermediate copper layer, and a thin cover consisting of
108-1180 C. and the color “normalhell-dunkel” are dis
solved in 100 parts by volume of ethyleneglycol mono
chromium, are, after exposure and development, prefer
ably etched With a solution consisting of 500 parts by 75 methylether. 0.3 part by weight of castor oil and 0.5
3,061,430
8
3. A compound according to claim 1 in which at least
two of R, R1, R2, and R3 are hydroxyl.
4. A compound according to claim 1 in which at least
part by weight of Methyl Violet BB are added, the solu
tion is ?ltered and then coated onto a polished zinc plate.
The layer is then dried by means of a current of warm
air. For the preparation of a cliché, the layer side of
three of R, R1, R2, and R3 are hydroxyl.
5. A compound having the formula
the zinc plate is exposed through a screen diapositive. 5
The exposed layer side which now carries the image is
treated with a cotton pad soaked with an about 2.5% tri~
on O
sodium phosphate solution containing also 10—15% (by
OH
H /
volume) of ethyleneglycol monomethylether. The parts
of the layer which are struck by light during exposure 10
rro—
\
are removed from the surface of the zinc plate and an im
age corresponding to the master used remains on the me
tallic base material. After rinsing with water the plate
is placed with its layer side on an earthenware trough
in which D is a naphthoquinone-(1,2)-diazide radical.
provided with vane wheels which centrifuge dilute (7 15
6. A compound having the formula
8%) nitric acid against the plate.
Etching is performed either by the usual process in sev
eral steps or according to the one-step process. Without
OH?!) OH
heating the zinc plate before etching, there is obtained
a printed plate being especially suitable for book and 20
illustration printing. Instead of a zinc plate it is also
possible to use a lead or magnesia plate, the results ob
tained being equally good.
Example VI
in which D and D1 are naphthoquinone-(1,2)-diazide
25 radicals.
7. A compound having the ‘formula
In 100 parts by volume of ethyleneglycol monomethyl
ether there are dissolved 2 parts by weight of the diazo
compound obtained from 1 mol of purpurogallin and 2
mols of naphthoquinone-(1,2)-diazide-(2)-sulfonic acid 30
chloride-(5) corresponding to Formula II and 6 parts
by weight of a m-cresol-formaldehyde resin novolak of
the qualities described in Example 5. 0.3 part by weight
of sesame oil and 0.5 part by weight of rosaniline hy
drochloride are added, the solution is then ?ltered and 35
coated onto a polished copper plate. After exposure un
der a photographic negative the layer is treated with a
cotton pad soaked with an about 2.5% trisodium phos
in which D, D1, and D2 are naphthoquinone-(l,2)-diazide
radicals.
8. A compound having the formula
phate solution containing also 10-15 % (by volume) of
ethyleneglycol monometliylether. Thereby the light
4-0
struck parts of the layer are removed from the metallic
carrier.
H? E‘) on
The copper plate carrying parts of the layer ac
cording to the master is now etched at 20—22° C. with
an iron chloride solution of 40° Bé.
no-
The light sensitive solution is also suitable for directly
l’
SiOz
coating rotating copper cylinders, one or more spray noz
zles being used. A printing plate especially suitable for
intaglio printing is obtained which after the usual chrom
ing of the etched copper cylinders is particularly suitable 50
for printing transparent foils.
It will be obvious to those skilled in the art that many
modi?cations may be made within the scope of the pres
\
/\
l
0
ent invention without departing from the spirit thereof,
and the invention includes all such modi?cations.
What is claimed is:
1. A compound having the formula
60
65
in which R, R1, R2, and R3 are selected from the group
consisting of hydroxyl naphthoquinone, quinone diazide
sulfonyloxy groups and lower alkoxy, at least one of R,
R1, R2, and R3 being a naphthoquinone diazide sulfonyl
oxy group, and X is selected from the group consisting
of hydrogen and halogen.
2. A compound according to claim 1 in which at least
one of R, R1, R2, and R3 is hydroxyl.
75
3,061,430
11)‘
13 in which at least three of R, R1, R2, and R3 are‘ hy
10. A compound having the formula '
droxyl.
O
*
17. A presensitized printing plate comprising a base
material having a coating thereon, the coating compris
ing a compound having the formula
|
H0
02
|
OHIO OH
(I)
OH
10
0
in which D is a naphthoquinone-(1,2) -diazide radical.
SIOZ
18. A presensitized printing plate comprising a base
material having a coating thereon, the coating compris
15 ing a compound having the formula
NFl I j
A
11. A compound having the formula
HO
0
on
I/
in which D and D1 are naphthoquinone-(1,2)-diazide
no
radicals.
O—
'
‘
19. A presensitized printing plate comprising a base
material having a coating thereon, the coating comprisi
ing a compound having the formula
.
1
S02
30
ll
0
12. A compound having the formula
35
in which D, D1, and D2 are naphthoquinone-(l,2)-diazide
radicals.
20. A presensitized printing plate comprising a base
material having a coating thereon, the coating compris
40 ing a compound haw/ing the formula
0
||
N2
'
1
SO:
A
H0
OH
SID:
[ El) /0
—\
HO
‘1’
S02
21. A presensitized printing plate comprising a base
13. A presensitized printing plate comprising a base 55 material having a coating thereon, the coating compris
ing a compound having the formula
material having a coating thereon, the coating compris
ing a compound having the formula
I?’ OH / R:
60
R1
X
R
in which R, R1, R2, and R3 are selected ‘from the group 65
consisting of hydroxyl naphthoquinone diazide sul-fonyl
oxy groups and lower alkoxy, at least one of R, R1, R2,
and R3 being a naphthoquinone diazide sulfonyloxy
group, and X is selected from the group consisting of hy
drogen and halogen.
14. A presensitized printing plate according to claim
13 in which at least one of R, R1, R2, and R3 is hydroXyl.
15. A presensitized printing plate according to claim
13 in which at least two of R, R1, R2, and R3 are hydroxyl.
16. A presensitized printing plate according to claim 75
3,061,430
11
12
22. A presensitized printing plate comprising a base
material having a coating thereon, the coating compris
ing a compound having the formula
f’
oxy groups and lower alkoxy, at least one of R, R1, R2.
and R3 being a diazide sulfonyloxy group, and X is selected
from the group consisting of hydrogen and halogen, and
treating the exposed coating with a developing solution.
5
-—N2
26. A process according to claim 25 in which at least
one of R, R1, R2, and R3 is hydroxyl.
27. A process according to claim 25 in which at least
two of R, R1, R2, and R3 are hydroxyl.
28. A process according to claim 25 in which at least
H0
$02
10
‘I? OH
(I,
three of R, R1, R2, and R3 are hydroxyl.
29. A process for making a printing plate which com
prises exposing a coated base material to light under a
\
master, the coating comprising a compound having the
formula
O
5'02
15
OHEI) 0H
HOI
N2-
20
ll
0
in which D is a naphthoquinone-(l,2)-diazide radical,
23. A presensitized printing plate comprising a base
and treating the exposed coating with a developing solu
material having a coating thereon, the coating compris
tion.
ing a compound having the formula
25
30. A process for making a printing plate which com
prises exposing a coated base material to light under a
H0
0
OH
master, the coating comprising a compound having the
formula
ll/
H0
30
0
|
S02
35
N
in which D and D1 are naphthoquinone-(1,2)'diazide
radicals and treating the exposed coating with a develop
ll
0
ing solution.
24. A presensitized printing plate comprising a base 40
material having a coating thereon, the coating compris
ing a compound having the formula
31. A process for making a printing plate which com
prises exposing a coated base material to light under a
master, the coating comprising a compound having the
formula
0
ll
0
_N,
OH (I?
45
Dr-SOr-O
N_
(1)
\
D-SOr-O
S02
HO
Casi-D2
O
50
S02
l
in which D, D1, and D2 are naphthoquinone-(1,2)-diazide
radicals, and treating the exposed coating with a develop
ing solution.
o—.
32. A process for making a printing plate which com
o
I
55 prises exposing a coated base material to light under a
SO:
master, the coating comprising a compound having the
formula
HO (I? OH
N
60
HO
ll
0
0
25. A process for making a printing plate which com
prises exposing a coated base material to light under a
AO.
master, the coating comprising a compound having the 65
formula
R72 (I? R3
R1
R
|
(a
N:
H
X
70
0
and treating the exposed coating with a developing solu
tion.
33. A process for making a printing plate which com
in which R, R1, R2, and R3 are selected from the group
consisting of hydroxyl, naphthoquinone diazide sulfonyl- 75 prises exposing a coated base material to light under a
3,061,430
14
13
master, the coating comprising a compound having the
master, the coating comprising a compound having the
formula
formula
OH
I
-.
5
O
40,
l
10
slog OH OII 011
0
O
15
(I)
SO:
I
n
20
=N2
u
and treating the exposed coating with a developing solu
tion.
36. A process for making a printing plate which com
prises exposing a coated base material to light under a
master, the coating comprising a compound having the
formula
0
‘
0
0
N2
25
N2
and treating the exposed coating with a developing solu
tion.
34. A process for making a printing plate which com- 30
prises exposing a coated base material to light under a
master, the coating comprising a compound having the
formula
I02
110
8'02
(I) o
O
‘I’
SO:
35
0
N
—N:
ll
40
0
and treating the exposed coating with a developing solu
BIO”
HO
tion.
37. A compound according to claim 1 containing halo
(|) OH
O.__._.
45 gen as a substituent directly linked to the purpurogallin
nucleus.
38. A presensitized printing plate according to claim
‘i
S02
13 in which compounds are used which contain halogen as
a substituent directly linked to the purpurogallin nucleus.
50
39. A process according to claim 25 in which com
pounds are used which contain halogen as a substituent
directly linked to the purpurogallin nucleus.
N:-—
6
55
and treating the exposed coating with a developing solu
tion.
35. A process for making a printing plate which com- 60
prises exposing a coated base material to light under a
References Cited in the ?le of this patent
FOREIGN PATENTS
706,028
739,654
Great Britain ________ .._ Mar. ‘24, 1954
Great Britain __________ __ Nov. 2, 1955
OTHER REFERENCES
Thorn and Barclay: Canadian Journal of Chemistry
30, pages 251-256 (1952).
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