Note: Descriptions are shown in the official language in which they were submitted.
11463g7
The present invention relates to color proofing foils and refers more
particularly to methods and materials for making color proofing foils of dark
colors of increased light sensitivity from light sensitive materials.
United States 3,326,682 teaches that positive working color proofing
foils can be prepared by aoating o-quinone diazide photosensitizers and color-
ants, with or without resins and other additives, upon a transparent support,
preferably polyethylene glycol terephthalate.
In the practice of the above patent, excellent color separation over-
lay proofing materials have been made from positive silver halide color separa-
tions used as exposure masks upon the appropriately colored proofing foil.After exposure and development in dilute aqueous alkali, the foils may be viewed
individually and then plaaed one above the other on top of a white reflecting
support to give a preview of the print which is to be made from plates from the
aforementioned aolor separation silver halide positives.
A black coated foil is customarily used as one of the layers to add
depth of color beyond that which would be obtained fron a three color separation
restricted solely to cyan, magenta and yellow. It has been found by experienae
that when a black dye or pigment is added to the foil coating aomposition, a
great increase in required exposure results due to the absorption of light by
the black dye or pigment. Dark aolored foils, either black or other dark colors,
similarly require undesirably increased exposure.
In the case of the black, one approach to reduced exposure has been to
reduce the level of dye or black pigment. m is has the undesirable effect of
giving a medium gray or light gray rather than a deep, rich, black
1~46397
which would be preferred. These considera~ions also apply to other dark
colors, which may be used apart from multicolor proofing processes in the
graphic arts.
Still another approach to overcoming the exposure increase result-
ing from the full quantity of black dye or pigment is disclosed in United
States 4,154,613. According to this invention, it was found that an over-
all exposure to light prior to or after imagewise exposure resulted in a
highly desirable reduction of required imagewise exposure even though the
dye or pigment level in the coating was at the desired level required for
full, deep, rich colors, However, special equipment and an added process
step is required.
A recent development in the technology of color proofing has been
the introduction of automatic exposure and development machinery. With the
use of such equipment, it is desirable that foils of all colors either deeply
or lightly tinted have the same exposure speed and development characteristics,
in order to avoid individual manual attention in processing. With the ex-
ception of the aforementioned technique of overall pre or postexposure, there
has existed no convenient method of adjusting the exposure speed of the
various differently colored proofing foils.
Therefore, one object of the present invention is to provide
methods and materials for making color proofing foils which overcome the
disadvantages of the prior art.
Another object is to provide novel light sensitive materials for
making color proofing foils of increased light sensitivity.
Another object is to provide novel light sensitive materials for
making color proofing foils in which exposure speed can be varied independ-
ently of the color selected.
-2-
11~639~
The present invention relates to a light sensitive material for making
a color proofing foil of increased sensitivity to actinic light. Thus, the
invention provides a proof sheet with increased exposure speed comprising a sub-
stantially transparent polymeric base sheet having a thin coating of a liqht sen-
sitive composition adhered to a surface thereof, said light sensitive composition
comprising a mixture of:
a) a colorant;
b) a light sensitive material selected from quinone diazides, conden-
sation products of aromatic diazonium compounds and combinations of
(1) a compound which splits off acid on irradiation and (2) a com-
pound with at least one group selected from ortho carboxylic acid
ester groups and carboxylic acid amide acetal groups; and
c) an effective amount of an anionic surfactant which is the reaction
product of about one mole of P205 with about 2 to 4.5 moles of a condensation
product of at least about one mole of alkylene oxide having 2-4 carbon atoms with
one mole of a compound containing about 6 to 150 carbon atoms and a reactive
hydrogen atom and selected from the group consisting of phenol, alkyl phenols,
aliphatic alcohols, fatty acids, fatty amines, fatty amides, rosin amines, long
chain sulfonamides, long chain-substituted aryl sulfonamides, and high molecular
weight mercaptans, said reaction product being prepared under substantially anhy-
drous conditions and at a temperature below about 110C. down to about room
temperature. The light sensitive coating compositions of this invention exhibit
greatly increased exposure speed, while retaining the required good adhesion to
film substrates, good scratch resistance, freedom from tack and acceptable resis-
tance to overdevelopment.
The components of the light sensitive coating compositions of the pre-
sent invention other than the anionic surfactant may be the conventional compon-
--3--
114639~
ents which are known in the art for such coatings used in positive acting and
negative acting light sensitive systems. It is important to choose surfactants
which are compatible with the components of both the coating solution as well as
the final dried coating in order that the image areas on the proof sheet be as
transparent as possible so that the color values are not affected by evidences
of incompatibility.
It is in the black and very dark colors that the greatest reduction in
exposure speed occurs compared to previous compositions. It is in these dark
colors that th6 major gain in exposure speed results when an~nic surfactants
are added to the coating compositions.
-3a-
1~46;3~7
me anionic surfactants of this invention are complex organic phos-
phate esters of nonionic surfactants which are obtained as the reaction products
of about one mole of P2O5 with about 2 to 4.5 moles of a condensation product of
at least about one mole of an alkylene oxide having 2-4 carbon atoms with one
mole of a oompound containing about 6 to 150 carbon atoms and a reactive
hydrogen atom and selected from the group consisting of phenol, aIkyl phenols,
aliphatic alcohols, fatty acids, fatty amines, fatty amides, rosin amines, long
chain sulfonamides, and high molecular weight mercaptans, said reaction products
being prepared under substantially anhydrous conditions and at a temperature be-
low about 110 C down to about rOQm temperature.
Preferred non ionic surfactants for reaction with P2O5 are those which
are the condensation products of ethylene oxide and the above mentioned organic
compounds possessing an active hydrogen. Anionic surfactant compositions
similar to those described herein are disclosed in United States Patent
3,004,056.
More particularly preferred anionic surfactants in this invention are
represented by formulas I and II below:
( 2 2 n O RO (CH2CH2O)
HO OH ( 2 2n/ \oH
I II
and mixtures thereof, where R = aIkyl or aryl radical and n = average number of
mDles of ethylene oxide ranging from 1 to 32.
Commercially available anionic surfactants made in accordance with the
description ~hnve are supplied by G~F Corporation and referred to as Gafac
Surfactants and G~FSTAT ~antistats. mese materials are mainly
1146397
liquids although some are waxy pastes. They range from 89 percent to 100
percent active products. Their specific gravity ranges from about 1.00 to
about 1.25. Their Pour Points, ASTM range from about C 0C to about 30C,
while their acid numbers, defined as mg KOH/g of product to the 1st inflecti-on
point ra~ge ~rom about 30 to about 400.
Such anionic surfactants are described in a brochure entitled
Gafac ~ Anionic Surfactants ~9643-Q18-3M-66) issued by the GAF Corporation
in 1976.
Additional commercially available anionic surfactants corresponding
to the above description are supplied by Finetex, Inc. and~are known as
Findets. They are described in Technical Data Sheets entitled Findet SB,
Findet OJ-P, Findet GC. Only those compounds with free acid groups are
effectlve.
The activity of the surfactants differs widely. Broadly, they are
~; effective at a concentration of about 0.5 percent to 60 percent by weight.
Some are active at low concentrations and may require that too high~-concen-
trations be avoided as it has been observed that m these cases the image
will be attacked or even removed during development. Conversely, higher
-~ ; concentrations of less active surfactants may be required. Thereis therefore
~20 for each surfactant an optimum range which can readily be determined by the
skilled artisan. In the case of positive working compositions proportions of
at least 10 percent by weight are preferred. More particularly preferred
surfactants are Gafac ~ RE-610, RE-870, PE-510, RA 600, and GAFSTAT AS-710.
The properties defining these surfactants are recited in the table following
Example 13.
Binder resins, plasticizers, activators and other customary addi-
tives may be included in the coating but such additives are not normally
;-5
.
- .
,
~ . ....
.,
~:14~;397
required in positive working systems.
Exemplary of suitable binder materials include cellulose esters such
as cellulose acetate, cellulose acetate succinate and cellulose acetate but-
yrate; polyvinyl acetals such as polyvinylbutyral and polyvinyl formal; poly-
amide resins, copolymers of vinyl chloride with polar monomers such as acry-
lonitrile, acrylic or methacrylic acid or their esters, and with vinyl
acetate; polymeric esters such as polyvinyl acetate or copolymers of vinyl
acetate with acrylic acid, methacrylic acid and their esters, or with maleic
acid or maleic anhydride; copolymers of styrene with comonomers such as ethyl
acrylate, vinyl acetate and maleic anhydride; natural polymers such as gela-
tin, casein or fish glue; polyvinyl alcohol; polyacrylamides; and like
materials. In negative working materials, the inventive addition of surfact-
ants primarily has the effect of reducing the developing time.
In a positive acting system, the resinous binder materials may be
alkali soluble resins such as phenol/formaldehyde novolak resins and like
materials, but styrene/maleic anhydride copolymers may also be employed, as
well as acrylic polymers soluble in aqueous alkaline solutions.
The coloring agents employed in the present invention include those
dyestuffs and pigments which are known in the art and which have colors sub-
stantially indentical with the standard colors of inks required for colorproofing; e.g., yellow, cyan, magenta and black. Examples of suitable color-
ants include Grasol Past Yellow SGL (C.I. Solvent Yellow 27~, Grasol Fast
Rubine 2BL (C.I. Solvent Red 128), Victoria Pure Blue FGA (C.I. Basis Blue
81), Neozapon Yellow GG (C.I. Solvent Yellow 79), Neozapon Fast Red BE ~C.I.
Solvent Red 122), Sudan Blue II (C~I. Solvent Blue 35 - C.I. 61554 ~S)),
Victoria Cyan F6G (C.I. 42025), Rhodamine FB (C.I. 45170), Rhodamine 6GDN
Extra (C.I. 45160), Auramine Cancentrate (C.I. 41000), carbon black and like
materials.
-6-
1~6397
Additional suitable dyes include Orasol* Yellow 3GLG (Ciba Geigy),
Orasol Black, CI Solvent Yellow 48, CI Solvent Black 29, CI Basic Violet 10, CI
Basic Red 1, CI Basic Blue 81.
Typical of the light sensitive oompositions found suitable for the pur-
poses of this invention are iminoquinone diazides, p-quinone diazides,
crguunone diazides, and condensation products of aromatic diazonium oompcunds,
if desired together with appropriate binders. Such sensitizers are described in
United States Patent numbers 3,175,906, 3,046,118, 2,063,631, 2,667,415,
3,867,147 with the oompositions disclosed in the last patent ~eing in general
preferred for negative working materials.
Generally, positive working light sensitive materials are preferred
and among these the materials based on o-quinone diazides are particularly pre-
ferred.
Additional suitable positive w~rking sensitizing compositions are dis-
closed in United States 4,101,323. mese are co~positions containing a ccmpound
(1) which splits off acid upon irradiation and a compound (2) having at least
one group selected from the group consisting of a carboxylic ortho acid ester
group and a carbQxylic acid amide acetal group.
It is to be emphasized that the sensitizers, colorants, optional
binders, support materials and techniques for coating are all conventional in
the art of preparing proofing foils.
The light sensitive coating composition containing the anionic sur-
factant may be most conveniently applied to the film substrate by forming a solu-
tion or dispersion of the coating ingredients in a suitable solvent, applying
the desired quantity of the solution to the surface of the film by any suitable
technique such as roller coating, dip coating, doctor blade
* Tra~emark
1~46397
coating or whirler coating, and drying to evaporate the solvent. The dry
coating thickness is preferably in the range of about 0.1 to about 10
microns. Suitable solvents include dimethyl sulfoxide, dimethyl formamide,
*etrahydrofuran, glycol ethers such as ethylene glycol monomethyl ether and
ethylene glycol mono ether, esters such as ethyl acetate, butyl acetate
and amyl acetate; ketones such as methyl ethyl ketone, cyclohexanone and~
diacetone alcohol, and mixtures of these.
The composition of the coating on a dry weight basis shall range
in the order of about 10 percent to 60 percent by weight of surfactant, an
effective amount of colorant, generally in the range of about 1 to 40 per-
cent by weight, and of course, effective amounts of the light sensitive
materials as are known in the art.
The concentration of the solids in the coating solution prior to
application to the substrate and drying depends upon the coating method used
in depositing the coating, but generally solutions contalning from about 2
to 20 percent by welght solids are satisfactory.
Exemplary of transparent film substrates to which the coating may
be applied are those polymeric films manufactured from polymers containing
polar groups in or pendant the polymer chain such as polyesters, cellulose
acetate and polyvinyl chloride. Such films generally have a thickness of
from about 1-5 mils, preferably about 2-3 mils. The adhesion characteristics
~ are maximized when a polyester film material is employed.
; The dried presensitized foils, which are colored by the dye applied
to them are exposed to ultraviolet light under a screened color separation
silver film transparency which has been produced in a copying camera from a
colored original. With a positive working proofing foil ~positive trans-
parency is used.
-8-
- .
. .
'
114~397
After exposure of positive working materials, the light decompo-
sition product and the dye are removed from the non-image areas by treatment
with a weakly alkaline solution, which normally contains 0.5 to 5 percent
by weight of an alkaline substance. Examples of such substances are alkali
metal silicates, alkali metal phosphates, alkali metal carbonates, and organic
bases such as ethanolamines, alkylamines, and alkylene diamines. The deve-
loped films are dried. ~hen they are superimposed in precise register a
colored image is obtained which either corresponds exactly to the multi-
colored original or, alternatively, renders possible a rapid correction of
the silver films by any of the conventional after-treatments.
After exposure and development~ the colored foil is overall exposed
to destroy the yellowish color due to residual sensitizer in the image.
The following examples are illustrative of the invention.
Example 1
A coating solution was prepared according to the following compo-
sition.
poly~methylmethacrylate/methacrylic acid) 85:15 5.1 g.
Orasol Yellow 3GLG (Ciba-Geigy) 0.86 g.
Orasol Black RL (Ciba-Geigy) 6.02 g.
naphthoquinone-~1,2)-diazide-(~)-5-sulphonic ester of 12.04 g.
2,3,4-trihydroxy-benzophenone
GAFAC ~ RE-610 ~GAF Corp.) 6.00 g.
GAFAC ~ RE-610 is an acid ester of mono and diesters of phosphoric acid.
It has specific gravity at 25 C c,f 1.10-1.12, a pour point (ASTM) of
~0C and an acid number of 62-72.
The acrylic polymer was dissolved in methyl ~ellosolve (monomethyl
ether of ethylene glycol). To this solution was added the remaining ingre-
dients. The solution was stirred for about one hour, filtered, and coated
on a 3 mil film of biaxially-oriented transparent polyethylene terephthalate
* ,7~r,0 ~ 9
~146397
and dried. The resulting sheet was employed as a black positive color proof-
ing film which was dry and tack free. Its transmission was 11.5 on the
Hunter L scale. These tests were performed using a Hunter Lab Model D25D3P
Color Difference Meter in accordance with the Instruction Manual ~rovided with
that unit. It was exposed through a positive color separation and a ~~
Stouffer stepwedge sensitiviey guide for 20 units (ca. 20 seconds) in a
Berkey Ascor (24" x 28") vacuum exposure frame. The exposed sheet was deve-
loped with an aqueous solution of 9 percent sodium lauryl sulphate which
removes the exposed areas, leaving the unexposed areas as image. The image
areas showed no signs of developer attack. The sheet was rinsed with tap
water and blotted dry. A clear 2 on the stepwedge was obtained. The film
was post-exposed for 20 units. A positive half tone black proofing image
resulted.
The clear base had a transmission of 87 on the Hunter L scale.
The density ~inverse to transmission) was adjusted by choice of coating
thickness. A transmission of 11.5 on the Hunter L scale is seen subjectively
as a very dense, deep black.
Example 2
The procedure of Example l was followed except that the surfactant
was omitted. After drying the coating on the support film, a transmission of
12 on the Hunter L scale was obtained, substanti~lly identical to the trans-
mission of the sheet of Example l and subjectively indistin~uishable. The
sheet was also dry and tack-free. In order to obtain a clear 2 on the
Stouffer stepwedge, an exposure of 320 units was required.
Example 3
The procedure of Example l was followed except that the surfactant
was omi~ted and the transmission of the film was adjusted to 21 on the Hunter
-10-
1146;~97
L scale. An exposure of 40 units was required to obtain a clear Step 2 on
the Stouffer scale. The sheet was visually perceived to be no more than a
medium to dark gray which nevertheless still required double the exposure of
the sheet of Example 1.
Example 4
The procedure of Example 1 was followed except that the acrylic
acid binder was omitted. There were no observable differences in the results.
Example 5
The procedure of Example 1 was followed except the Gafac ~ PE-510
was used as the surfactant and Lytron 820 (copolymer of styrene-maleic*)
was used as a binder instead of acrylic acid. Gafac ~ PE-510 is also an
acid ester and is a mixture of mono and diesters of phosphoric acid. A dry
tack-free film was obtained. An exposure of 30 units was required to obtain
a clear Step 2 on the Stouffer scale.
Example 6
Instead of GAFAC ~ RE-610 as described in Example 1,4 g. of
GAFSTAT ~ AS-710 was used and the binder resin was eliminated. GAFSTAT ~
AS-710 is a free acid of complex phosphate esters. It has a specific gravity
at 25C of 1.05, a pour point ASTM of 18 C and an acid number of 58-70. The
unexposed sheet was dry and tack-free and an exposure of 20 units (ca. 20
seconds) was used.
Example 7
The procedure of Example 6 was followed except that the quantity
of GAFSTAT ~ AS-710 was increased to 24 g. Although the sheet was dry and
tack-free, there was some developer attack upon the image.
*) anhydride having an acid number of 180 and a mean molecular weight of
20,000)
-11-
1146397
Example 8
A solution of the following composition was prepared:
acrylic acid polymer 25.5 g
Orasol Yellow 3GLG 4.3 g
Orasol Black RL 30.1 g
N-dephenoxymethyl-E-caprolactame 18.4 g
2-~4-ethoxy-naphth-1-yl)-4,6-bis-trichloromethyl- 2 g
s-triazine
The acrylic acid polymer was dissolved in monomethyl ether of
ethylene glycol. To this solution were added the remaining ingredients
with stirring for about one hour. The resulting solution was filtered and
spin coated onto a biaxially-oriented polyethy]ene terephth,al~te-fi-lm to a
density of 13 + 1 on the L scale using a Gardner XL -31 Digital tristimulus
colorimeter. The coated sheet was exposed on a Berkey/Ascor exposure unit
for 150 unlts ~ca. 150 seconds) and treated with an aqueous alkaline deve-
loper. The sheet did not develop and no clear step showed.
Example 9
The procedure and recipe of Example 8 was follow~d,-except that
30 g. of GAFAC ~ RE-610 was added to the coating composition. With the
same exposure ~150 units). Treatment with developer cleaned out the non-
image area. Overdevelopment resistance was good.
Example 10
A. A coating solution was prepared by dissolving 0.604 grams of
Orasol Yellow 3GLG. 0.452 grams of Rhodamine FB, 1.032 grams of Rhodamine
6GDN Extra, and 4.754 grams of the -quinone diazide of Example 1 in 49.00
grams of methyl cellosolve and 49.00 grams of methyl ethyl ketone. The
solution was filtered and coated on a polyester film. This magenta posi-
tive color proofing film was exposed for 20 units. A clear 2 stepwedge was
obtained after the film was developed with the same developer as in Example
1. Overdevelopment resistance was good.
-12-
1146397
B. GAFAC ~ RE-610 (0.6 g) was added to the coating solution of
Part A of this example and then coated on the polyester film. With 20 units
exposure, a clear 8 stepwedge was obtained, showing 6 steps of increase in
exposure speed. Overdevelopment resistance was poor.
Example 11
A. Victoria Pure Blue FGA, 1.176 grams, the the o-quinone diazide
of Example 1, 2.858 grams, were dissolved in 24.70 grams of methyl cello-
solve and 74.12 grams of methyl ethyl ketone. This coating solution was
coated on polyester film. This cyan positive color proofing film was
exposed for 20 units, then developed with the developer of Example 1. A
clear 2 stepwedge was obtained.
B. The procedure of Part A of this example was used except that
0.5 grams of GAFAC ~ RE-610 was added to the coating solution. The coated
film gave a clear 4 stepwedge with 20 units of exposure showing a 2-step
increase in exposure speed. Overdevelopment resistance was good.
Example l?
The procedure of Example 8 was followed except that instead of
the sensitizer used therein, 60.2 g. of the o-quinone diazide of Example 1
was used and the exposure was reduced to 20 units on a Berkey/Ascor exposure
unit. The density of the coated sheet was also 13 ~ 1 on the L scale.
After treatment with the developer of Example 1 the background area was not
completely clean and no clear step showed.
Example 13
The procedure of Example 12 was followed except that an anionic
complex phosphate ester was added to the recipe to determine its range of
effectiveness. The amounts were selected to become 10%, 15%, 20%, 30%, 40%,
50%, and 60% by weight on the basis of the dry solids content of the overall
11463g7
coating. The surfactants chosen for the experiments were:
Gafac ~ RE-610 Gafac O BI-750
Gafac ~ PE-510 Gafac ~ RE-870
Gafac ~ RA-600 Gafac ~ RM-710
Gafac ~ BH-650 Findet~R)GC
Gafac ~ BG-510 Findet(R)SB
Gafac ~ RS-410 Findet~ )OJ-P
Gafac ~ RS-710
The designation of the surfactants, the chemical type, the acid
number, specific gravity at 25C, and pour point, ASTM are given in the
following table.
In all cases, the coating thickness was adjusted to yield an L
value of 13 + 1 as measured on the Gardner XL-31 Digital tristimulus
colorimeter. Also in all cases, an exposure of 20 units on a Berkey/Ascor
exposure unit was used. A standard development was used in all cases, using
the aqueous developer of Example 1.
Observations were made on the number of the clear steps shown
after development, compatibility of the sheet, attack on the image or
coating by the developer. The observations are noted in the appropriate
spaces in the Table.
Not all proportions of surfactant were used. An omission of a
specific proportion of surfactant; e.g., 15%, 30%, 40%, etc. is shown by a
dash in the appropriate space.
-14-
" 1~46397
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il~6397
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- 15 a -
11~639~
As noted in Example 12, in which no surfactant was used, the st,mdard expo-
sure of 20 units was insufficient to enable the developer to clean the
background or show any clear step on the Stouffer scale. Therefore, as in the
series with Gafac ~ RS-410, the surfactant although not as effective as ,
for example Gafac ~ RE-610, nevertheless produced an increase in effective
exposure speed compared to the control recipe which contained no surfactant.
zu Hoe 79/K 063
, . . . _
-Example 14
A soIution of the following composition was prepared:
2.3 -g of the copolymer of Example 5,
0.37 g of p-toluene sulfonic acid,
1.67 g of calcogene-SFW, unblended,
0.68 g of Rhodamine 6 GDN Extra
i j . ~
,~ ~ 0.6 g of Victoria Pure Blue FGA
3.46 g of a polycondensation product o 1 mole of
3 methoxy-diphenylamine-4-diazonium salt and
1 mole o 4,4' -bis-methoxymethyl-diphenylether
in
90 g of ethylene glycol;monomethyl ether.
20 An additional solution was prepared by adding~0.5 g of GAFAC ~ RE-610 to the
~abovementioned f~rmulation. The two solutions were whirler coated onto a
75 ~m thick polythylene-terephthalate film, draed and exposed for 30
seconds under an original. The exposed samples were developed for 30
seconds using the developer of Example 1.
~ The first sample was incompletely developed and showed unclean
; non-image areas, while the second sample had completely and cleanly
developed.
~.
~ -16-
" ~ ~ ' . " '
~: :
,
~ il46397
Example_15
A solution was prepared which was composed of:
15.7 g of the copolymer of Example 1,
3.9 g of trimethylolpropane triacrylate,
0.75 g of 9-phenyl acridine and
0.5 g of Acetosol~Fire Red in
44 g of ethylene glycol monomethyl ether.
To a solution of the same composition 0.11 g of GAFAC ~ RE-610 was addition-
ally added. The two solutions were whirler coated onto polyester films and
dried. The light-sensitive films thus obtained were exposed for an equal
length of time under an original and developed for 5 seconds using a 5 per-
cent aqueous sodium lauryl sulfate solution. The second sample which
contained the surfactant was cleanly developed, whereas development of the
first sample was incomplete. When the development time was extended to 8
seconds, the first sample was also cleanly developed.
~ ~ 4J~
-17-
