DE1472871A1 - Gelatin-silver halide photographic emulsion - Google Patents

Description

ι η ί 4 »- .4 *« - - ^ fc-

PATENT ATTORNEYS ₂₅ / ^L li ^^ T ^ 29 Oct. 29 1 ₉ 6 ₅ DR. WOLFF, H. BARTELS,
DR. BRANDES, DR.-ING. HERO

I AMfSB CTPACCC CI

TFiFV.

8 MÖNCHEN 22, Thiersdisfr. 8 / ΙΠ

TELEPHONE 293297. p «» _g .Mr .. i? N mfi

Eastman Kodak Company, 3 ^ 3 State Street, Rochester, State New York, United States of America

Gelatin-silver halide photographic emulsion

The invention relates to a gelatin-silver halide photographic emulsion in which this developed Silver has a particularly high opacity.

The maximum optical density of a silver image of a photographic film depends on its exposure, development and drying and, as a result, the opacity not only from the amount of developed silver, but also like the silver in the emulsion layer

° of the development, and also of the unity

^ it is subjected to flow while drying .. The • ^ The term "opacity" here refers to the ratio

ο,

co of the optical density of the developed silver to the effective

* ° borrowed amount of silver.

It has been shown that the structure and density of the silver deposit, which is caused by the reduction of the silver halide . metallic silver is generated during development and ; Drying is influenced by the binder in which the Silver halide grains are suspended.

The invention was based on the knowledge that the opacity photographic gelatin silver halide emulsions in

W can be improved in an excellent way if about 5 to 50 percent by weight of the gelatin is replaced by a synthetic polymer of a very specific composition.

The gelatin-silver halide photographic emulsion of the invention is characterized in that, as a synthetic polymer, it is a polymer with recurring units of the formula:

i. CiUCH

. ί

I / ¹

contains, in which R ^ represents a hydrocarbon chain having 1 to 5 carbon atoms which _{is substituted by 1 to 3 groups of the formula -COXR 2} R-, in which

X one - N or

- N - N group in which R _k

9098T2 / 0912

means a hydrogen atom or an alkyl group with 1 to 5 carbon atoms "and R ₂ and R- represent hydrogen atoms, alkyl groups with 1 to 5 carbon atoms, alkyl groups substituted by alkoxy groups with 1 to 5 carbon atoms or alkyl groups substituted by hydroxyl groups"

It has been shown that by adding the synthetic polymers used according to the invention, not only can the opacity M of the silver halide emulsions be increased and the maximum density increased, but that the γ values and very often the sensitivity of the emulsion can also be increased .

A photographic gelatine-silver halide emulsion which contains as synthetic polymer a polymer composed of recurring units of the formula: _{Λ has proven to be particularly advantageous}

- CH -

0 ~ °

C NH (CH ₀ ) -G-NH-CH- - CH ₀ -OH

dH d. d

where ir = - 1 to 5 ..

It has been shown that in order to achieve an improved cushioning force not nua? Homopolymers are suitable, i.e.

S09ft2 / Q912

- I ₁ _

sate, which is built up only from the specified recurring units are, but rather that those are also suitable which consist of copolymers and their recurring Units only partially have the specified structures. This means that the polymers which can be used according to the invention for Partly from units of the specified formulas and partly from others Units of the following general formula:

ψ. -CH ₀ CH-

d I

can be constructed.

In this formula, Y represents a photographically inert group, ie, for example a hydroxyl group, an ester group such as an acetoxy, propionyloxy or butyryloxy group, an amide group such as an N-alkyl or ^, Ν, Ν-dialkylamide groups, wherein the alkyl group consists of 1 to 5 carbon atoms, a carbamate group, such as a group -OCONH-R ₅ -COORg, wherein R ₅ and Rg represent carbon radicals having 1 to 5 carbon atoms, preferably alkylene radicals », etc.

The polymers used according to the invention can thus, for example consist of copolymers, some of which consist of units of the formula:

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CH ₀ - CH -

² I.

NH -

and partly from units of the formula:

- CH ₂ - CH

exist.

Synthetic polymers of the type described can be produced in a known manner, for example by treatment of the reaction product of polyvinyl alcohol and an ester of an isocyanato-mono- or polybasic fatty acid with an amine. The reaction of the isocyanato compound with the polyvinyl alcohol can be partially or completely ^ just like when the amine is reacted with the reaction product initially obtained.

The following describes the production of some polymers that can be used according to the invention *

A) Production of polyvinyl-ß-hydroxyethylcarbamylmethylcarbamate) (70 mole percent conversion)

In a 5 liter flask equipped with a stirrer, thermometer, Reflux condenser with calcium chloride tube and dropper

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funnel, were 2l6O milliliters of pyridine and 26 * 1 g of polyvinyl alcohol of a lower viscosity grade, which had been dried overnight in a heated to 50 ⁰ C air oven accommodated. With stirring, the suspension was made up by means of a

\ a temperature of 95 ° C heated heating bath is heated. Drop by drop 5 ^ 2 g of ethyl isocyanatoacetate were added. The dropping speed was about 5 to 6 drops per second «within 5 to 10 minutes of starting the addition

■ f the reaction mass was clear and the viscosity rose. the

The reaction mass became more and more gelatinous. However, it remained so soft that it could be stirred further. The addition of the ethyl isocyanatoacetate was complete after 25 minutes. The temperature of the reaction mass was 119 ° C. After a further half hour, the temperature dropped to 110 ⁰ C. After within a period of half an hour 802 g Ithanolamin had been added through the dropping funnel, 480 milliliters of distilled water was added slowly. The reddish colored gel broke open in the process, and in a few

A homogeneous pourable liquid formed for W minutes. The mixture was heated to a temperature of 90 to 100 ^° C. for four and a half hours while stirring. The mass was then ^{cooled to 60 °} C. and poured into isopropyl alcohol with stirring. A soft yellowish polymer precipitated out and was left to stand overnight in fresh isopropyl alcohol. After that it was half an hour

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washed, the washing liquid being decanted a total of 7 times became. The originally soft polymer hardened during washing and formed granules. The polymer was then transferred to a mill, in which it was mixed with 1 1/2 liters of water. One formed viscous, yellow, pourable mass with a pH of 9.40. The mass was then mixed with a sufficient amount of one Ion exchange resin (Ambe'r lite IR-120) treated, whereby the pH was reduced to 2.32.

Part of this acidic approach was used for analytical purposes used. The main part of the batch was adjusted to a pH of 6.20 by adding NaOH. The yield was 565 g (dry weight).

B) Production of polyivinyl-ß-hydroxyethylcarbamylmethylcarbamate)

In a 2-liter flask equipped with stirrer, thermometer, reflux condenser with a calcium chloride tube and a dropping funnel, IO8O milliliters of pyridine and 132 g (3 moles) of a polyvinyl alcohol of low viscosity were taken, the overnight in an air oven at a temperature of 50 ⁰ C had been dried. While stirring, the suspension was heated to 92 ° C. by means of a heating mantle, whereupon 2.1 moles (70 mole percent = 272 g) of ethyl isocyanatoacetate were added within a space of 1 / M hour. The temperature of the batch rose to 115 ° C. Heating was continued for 1/2 hour

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sets, the temperature of the batch falling spontaneously to 107 ° C. The temperature was reduced to 90 ° C. by external cooling. The polymer was then isolated by pouring the batch into distilled water. The white, yellow polymer was washed a total of 6 times in a mill with distilled. A sample of the polymer was dissolved in acetone, precipitated in ethyl acetate and dried under reduced pressure at room temperature. The nitrogen content of sample W long at 5.9 % _t corresponds to 73 percent by weight of vinyl carbethoxymethyl carbamate units in the polymer.

500 grams of the wet polymer was placed in a 2 liter flask containing 300 grams of aminoethanol. The flask was sealed therein and shaken for several days at room temperature until a viscous, yellow, pourable mass was obtained. The polymer was then precipitated by pouring it into ethyl acetate with stirring. The soft, yellow precipitate obtained was washed several times in a kneader with fresh ethyl acetate and then placed in 500 milliliters of distilled water. The acidic solution of the polymer was then treated with a sufficient amount of an ion exchange resin (Amberlite IR-120) to reduce the pH of the batch to 2.70. Part of the batch was poured into ethyl acetate for analytical purposes, whereupon the polymer precipitated. It was dried in a vacuum oven at a temperature of 35 to 40 ° C. The nitrogen content

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was 10 _t 35 % _t corresponding to 60 percent by weight of vinyl β-hydroxyethylcarbamylmethylcarbantate units. The sthoxyl group content was 3 »0 % _t, corresponding to 11.5 percent by weight of unreacted vinyl carbethoxymethyl carbamate units. The carboxyl group content corresponded to 0.34 milliliters of normal sodium hydroxide solution per g, corresponding to 4.85 percent by weight of vinyl carboxymethyl carbamate units. 23.65 percent by weight of the polymer thus consisted of vinyl alcohol units.

The main part of the batch was diluted by adding Sodium hydroxide solution adjusted to a pH of 6.0. The yield was 268 g (dry weight).

C) Production of poly (vinyl-ß-hydroxyethylearbamylmethylcarbamate) (70 mol percent conversion of the butyl isocyanatoacetate)

In a 2-liter flask equipped with a stirrer, thermometer, The reflux condenser with CaIciura tubes and dropping funnel were " 720 milliliters of pyridine and 88 g of polyvinyl alcohol that had been dried overnight in an air oven at 50 ° C. The suspension was heated to 93 ° C. by means of a heating mantle while stirring. Then, drop by drop, 220 g Butyl isocyanatoacetate added. Within 10 minutes the slurry became clear and the viscosity increased. Shortly thereafter the viscosity decreased again and a uniform, homogeneous mass was formed. The addition of the butyl

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isocyanatoacetates took place within 20 minutes * The heating was continued for 2 hours while stirring. The temperature dropped spontaneously from 116 ° C. to 110 ° C. Within a period of 15 minutes, 270 g of ethanolamine were then added, followed by 160 milliliters of distilled water. . . With stirring for 4 3 / Ί hours was heated further to a temperature of 95 to 100 ⁰ C. The batch was then heated to 60 ° C

■ 'cooled, whereupon the polymer by pouring the approach

W was precipitated in isopropyl alcohol. The precipitated soft cake was then left to stand overnight in fresh isopropyl alcohol and then washed for 1: 2 hours, decanting off after each wash. It was decanted 6 times in total. The polymer hardened upon washing and formed granules. This was placed in a ball mill and 500 milliliters of distilled water was added. The basic mass was then mixed with a sufficient amount of an ion exchange resin (Amberlite IR-

t 120), the pH value being reduced to 1.75.

** Part of the batch was poured into isopropyl alcohol, causing the polymer to precipitate. This polymer was used for analytical purposes. The main part of the batch was brought to a pH of 6.0 by adding alkali. The yield was 206 g (dry weight).

D) Production of poly (vinyl-1,2-bis £ ~ ß-hydroxyethylcarbamyl_ / ethylcarbam: ate)

Into a 1 liter flask equipped with a stirrer, thermometer, reflux condenser with calcium tube and dropping funnel

909812/0 912

- ii -

180 milliliters of pyridine and 22 g of low viscosity polyvinyl alcohol brought. While stirring, the suspension was heated to 99 ° C. by means of a heating mantle, whereupon dropwise 13 ^ g of diethyl a-isocyanatosuccinate were added.

When the temperature increased to 119 ^° C., a clear, dark amber-colored mass was formed. Heating was continued for 2 hours. The polymer was precipitated by pouring the batch into distilled water. It was then placed in a kneading mill where it was washed several times with fresh distilled water. The still moist polymer was then placed in a bottle containing 600 milliliters of ethanolamine. The bottle was closed and shaken at room temperature for several days until a viscous reddish mass was present. The polymer was isolated from this mass by pouring the mass into isopropyl alcohol. The polymer was washed several times with fresh isopropyl alcohol to remove most of the unreacted ethanolamine. Then, the polymer was dissolved in 200 milliliters of distilled water g, and the aqueous solution with a sufficient amount of ion exchange resin (Amberlite IR-120) was treated, wherein

the

& SS pH was reduced to 2.60. A sample of the batch was placed in isopropyl alcohol, whereupon the polymer precipitated. It was dried in a vacuum oven at a temperature of 35 to ftO ° C and analyzed. The polymer contained 11.4 % nitrogen, corresponding to 63.5 percent by weight of vinyl 1,2- (dihydroxyethylearbamido) ethyl carbamate units; 7.5 % ethoxyl

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groups, corresponding to 21.6 percent by weight unreacted Vinyl l, 2- (dicarbethoxy) ethyl carbamate units and a carboxyl group content corresponding to 0.73 milliliters normal Sodium hydroxide solution per g, corresponding to 14.7 percent by weight of vinyl 1,2- (dicarboxy) ethyl carbamate units.

The main part of the batch was adjusted to a pH of 6.20 by adding dilute sodium hydroxide solution. A Beckman G pH meter was used for this purpose. The yield was 89 g (dry weight).

E) Production of poly (vinyl-1,3-bis ^ ~ * ß-hydroxyethylcarbamyl7 propyl carbamate) (100 mole percent conversion)

In a 200-milliliter flask equipped with stirrer, thermometer, Rückflußkühlerr with calcium tube and dropping funnel, 72 ml of pyridine and 8.8 g of polyvinyl alcohol of a lower viscosity grade, had been wherein heated overnight in an air oven at 5O ⁰ C, brought. With stirring, the suspension was heated by a mantle heater at 90 ⁰ C. 46 g of diethyl α-isocyanatoglutarate were added dropwise. The addition was made over a period of 15 minutes. A homogeneous, dark amber barbene mass formed, the temperature rising to 113.5 ° C. The heating was continued for 2 1/4 hours, the temperature dropped spontaneously to 98 ⁰ C. The reaction mixture was then poured into distilled water, whereupon a soft, light yellow polymer precipitated. After washing several times

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of the soft cake in water, this was dissolved in acetone and again by slowly pouring it into water with stirring failed. The obtained soft cake was then washed with water in a kneader and then washed dried in a vacuum oven at 40 to 45 ° C. It became 46 g of a rubbery one

Obtained polymers, the nitrogen content of which was 4.9 to 5.0 % and which contained 31 »5 % ethoxyl groups.

The polymer was placed in a bottle containing 300 grams of ethanolamine and 50 milliliters of water. The bottle was closed and shaken at room temperature for several days until a viscous amber-colored mass had formed. By pouring this mass into acetone with stirring, the Polymer isolated. It was washed several times with fresh acetone to remove most of the unreacted ethanolamine to remove. The polymer was then dissolved in water, followed by the aqueous solution with a sufficient amount of an ion exchange resin (Amberlite IR-120), the pH being reduced to 2.30. Part of the acidic solution was used for analytical purposes. The main part was adjusted to pH by adding aqueous sodium hydroxide solution brought from 6.55. The yield was 28.8 g (dry weight). The following analysis values were obtained:

Nitrogen content 8.3 / 8.6; Ethoxyl group content = 12.0} Consumption of 1 normal sodium hydroxide solution per g of polymer = 0.28 milliliter.

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F) Production of poly (vinyl-bis / ~ ß-hydroxyäthyl_7-carbamylmethylcarbamate) ~ "

200 milliliters of iminodiethanol, 20 milliliters of distilled water and 43 g of poly (vinyl carbethoxymethyl carbamate), prepared as described in the example, were placed in a 500 milliliter flask. The mixture was heated on a steam bath with gentle stirring for approximately 24 hours during which time a clear, reddish mass formed. The polymer was isolated by pouring this mass into isopropyl alcohol with stirring. The soft, yellow polymer was kneaded several times by hand in fresh isopropyl alcohol and then taken up in 100 milliliters of distilled water. The resulting aqueous solution was then treated with a sufficient amount of ion exchange resin (Amberlite IR-120) to reduce the pH to 2.70. Part of the batch was poured into isopropyl alcohol for analytical purposes, whereupon the polymer precipitated. It was dried in a vacuum oven at a temperature of 35 to 40 ^{° C.} The polymer contained 8.7 % nitrogen, corresponding to 46.2 percent by weight of vinyl bis (β-hydroxyethyl) carbamylmethylcarbamate units and 7.3 % ethoxyl groups, corresponding to 28 percent by weight of unreacted vinylcarbethoxymethylcarbamate units. The carboxyl group content corresponded to 0.62 milliliters of a normal sodium hydroxide solution per g of polymer, corresponding to 9.0 percent by weight of vinyl carboxymethyl carbamate units. The polymer thus still contained 17 percent vinyl alcohol units.

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The main part of the batch was adjusted to a pH of 6.10 by adding dilute sodium hydroxide solution. The yield was 33 g (dry weight).

G to J)

According to the method described under A), further polymers with various proportions of alkanolamide carbamate, Ester carbamate, carboxycarbamate and vinyl alcohol units are produced. The composition of the polymers A to J and their production method can be found in the following table I:

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Table I.

Polymer Compounds used in manufacture

R-NCO

R-NH, composition of the polymers in wt .- # of each Groups (calculated from analysis values)

Alkanol unreacted carboxy vinyl alcohol amide set ester carbamate (difference) carbamate- carbamate-

90981 G
B. Ethyl isocyanato
acetate
Ethyl isocyanato
acetate 2-amino
ethanol
2-amino
ethanol 75.2
60.5 CD H Ethyl isocyanato
acetate 2-amino ~
ethanol 80.0 CO
ro A. Ethyl isocyanato
acetate 2-amino
ethanol . 40.0 J Ethyl isocyanato
acetate 2-amino
ethanol 42.0 C. Butylso-
cyanatoacetate 2-amino
ethanol 69.7 E. Diethyl-a-iso-
cyanatοglutarate 2-amino
ethanol 44.7 D. Diethyl.e-iSO-
cyanatosuccinate 2-amino
ethanol 63.5 P. Ethyl isocyanato
acetate Imino
diethanol 46.2

11.5 10.0 29.6 32.5

36.4 21.6 28.0

6.1 4.85 4.0 3.34 3 * 04 4.06 6.1 14.7 9.0

18.7 23.15 6.0 27.06 22.46

12.8

16.8

K to R

A number of other polymers were produced according to the processes described under A to P. The one used to manufacture the Polymers used starting components and the composition of the polymers are in the following Table II reproduced:

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Table II

Polymer used for production links

Composition of the polymers in parts by weight of each Groups (calculated from analysis values)

K R-NCO
* R-NH ₂ Alkanol
amide
carbamate not the other way around
sat
Ester carbamate Carboxy
carbamate » Vinyl-
alcohol-
(Difference) L. Ethyl iso-
cyanatoacetate 3-aminopro-
panol 95 - 0.7 606 11 Ethyl iso-
cyanata acetate Isopropyl
amine 48.1 21.9 18.6 11.4 CP
KJ N Ethyl iso-
cyanatoacetate 2-methoxy
ethylamine 61 - 10 29 / 091 O Ethyl iso-
cyanatoacetate 2-ethoxy
ethylamine 56.6 - 9.3 34.1 κ » P. Ethyliso
cyanatoacetate 2-amino-2-
methyl-1-
propanol 35 33.4 13.6 18th Q Ethyl iso-
cyanatoacetate 2-amino-2-
ethyl-1,3-
propanediol 64 - - 36 R ' Ethyl iso-
cyanatoacetate 2-amino-2-
hydroxy
methyl-1,3-
propanediol 67 7.0 26.0 Ethyl iso-
cyanatoacetate 2-amino
ethanol 52.7 11.1 24.8. 11.4

The following examples are intended to illustrate the invention in more detail:

example 1

Polymers A through J were added to a normal, sulfur and gold compound sensitized, high sensitivity, coarse grain silver bromoiodide emulsion of the type used to make medical X-ray films. The emulsions were listed on cellulose acetate film such £ taken that to a film surface of 0.09 m (1 square foot) 560 milligrams of silver and 900 milligrams of gelatin accounted for. Samples of the films obtained were exposed in a sensitometer (type Eastman 1 B) and then developed for 3 minutes in a developer of the following composition:

p-methylaminophenol sulfate 2 _f 2 g

Sodium sulfite (dehydrated) 72.0 g, hydroquinone 8.8 g

Sodium carbonate 130.0 g f potassium bromide 4.0 g

made up to 1 liter with water.

Those obtained using Polymers A, B, H and J. Results were the same as those obtained with an emulsion containing polymer G. The measurement results,

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obtained from examining the emulsions containing Polymers A, B, H and J were therefore made for convenience omitted for the sake of The results shown in Table III below clearly show the improvement the opacity of the emulsions which contained one of the polymers described.

Table III G 100 gamma veil Max polymer Concentration Relative
per mole Ag sensitivity
opportunity . 123 1.8H 0.04 1.70 no G 100 2.40 0.05 2.10 G 43 G 123. 2.20 0.06 1.86 no - 123 2.76 0.06 2.30 D. 60 G 100 2.80 o, o6 2.25 P. 60 G 138 1.60 0.05 1.60 no - 132 2.36 0.06 2.36 E. 60 2.06 0.07 2.10 C. 60 Example 2

According to the procedure described in Example 1, an emulsion was tested: which is a terpolymer of vinyl alcohol, Vinyl carboxymethyl carbamate and vinyl N-butylcarbamylmethyl carbamate units contained. The percentage by weight of vinyl

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t472871

carboxymethyl carbamate units was 24 % and the weight fraction of vinyl N-butylcarbamylmethyl carbamate units was 32%. Using this polymer, the results shown in Table IV below were obtained.

Table IV

Polymer concentration
per mole of Ag

Relative gamma veil D

Feel

loan

Max

100 123

1, TO 1.83

0.07

1.69

Example 3

Following the procedure described in Example 1, the Polymers E to R tested. The results obtained are given in Table V below.

Table V

polymer concentration
in g / mol Ag Relative
Sensation
opportunity gamma veil K 45 126 1 * 48 0.14 K 0 100 1,1.8 L. 30th 102 1 * 68 O ₁₈ IJ L. Q 100 1 * 45 0 * 12 M. 45 123 1.48 Q, ll M. Q 100 1 * 20 0 * 10 ^; -; IT 30th 97 1.6ο 0.13 N 0 100 Q 45 102: l "60 ο ,, ια 0 0 100 1 * 38 Q ^ lQ P. 45 112 1 * 65 ο * α8 P. 0 IQQ 1.21: Q _K 1Q Q 45 1Ä Μ » 0 100 1 * 27 Q ^ 15 R. % 5 135 R. Q 1 25

A3La ttesoneteps; ^ o ^ fcelXhaCte have the Ecsljpneajen e3cwieseiii _ft from ratederkenrenden units, the

- "CH ρ, -

Töxsciipolymeren of the invention can be in Gelatin-silver halide emulsions in amounts of about 10 to 75 grams per mole of silver and 5 to 50 percent by weight, based on the gelatin content of the emulsion.

Particularly advantageous results are obtained when the polymers described are used for the production of X-ray emulsions. This X-ray emulsions Las% sen, for example, to process X-ray film elements having an intensifying screen, as she / 57b are described for example in German patent application E 25 353 IXa.

The gelatin-silver halide photographic emulsions of the invention can use a variety of chemical sensitizers. Stabilizers, sensitivity increasing compounds, coating aids and gelatin hardeners such as Plasticizers, such as those in the United States patent 3 039 873 are included. G

The molecular weight of the polymers used according to the invention can vary widely. Have to be particularly beneficial The polymers turned out to be different from polyvinyl alcohols with an inherent viscosity of .0.10 to 0.90, preferably 0.30 to 0.50, or else which have a viscosity than if they had been produced from such polyvinyl alcohols. The inherent viscosity results

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results from measurements in water at a concentration of 0.25 g per 100 milliliters of solution at 25 ° C

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Claims (3)

Claims 1) Gelatin-silver halide photographic emulsion in which the gelatin to 5 to 50 percent by weight by a synthetic Polymer is replaced, characterized in that it is a polymer with repeating as a synthetic polymer Units of the formula: CH ₂ - ■ CH - -NH - ¹ I. contains, in which R ^ represents a hydrocarbon chain having 1 to 5 carbon atoms, which is substituted by 1 to 3 groups of the formula -COXRpR-, in which
X an -N or -NN _v group, Indians Ri ₁ represents a hydrogen atom or an alkyl group of 1 to 5
Means carbon atoms, and R ₂ and R ^ are hydrogen atoms, alkyl groups having 1 to 5 carbon atoms, alkyl groups having 1 to 5 substituted by alkoxy groups
Represent carbon atoms or alkyl groups substituted by hydroxyl groups. 909812/091 2 2) Photographic gelatin silver halide emulsion according to claim 1, characterized in that it is a synthetic Polymer contains a polymer that is 30 to 100 percent by weight of units of the formula and 0 to 70 percent by weight from units of the formula - CH ₂ -CH- wherein Y represents a photographically inert group. 3) Gelatin-silver halide photographic emulsion after Claims 1 and 2, characterized in that it contains a polymer as synthetic polymer, which is 30 to 100 percent by weight from recurring units of the formula -CH ₂ -CH- C ~ NH - (CH ₂ ) _n - C - NH - CH ₂ - CH ₃ - OH where η = 1 to 5. 909812/0912 H) Photographic gelatin silver halide emulsion according to claims 1 to 3 *, characterized in that it contains a poly (vinyl alcohol-vinyl-ßhydroxyäthylcarbamyliaethylearbamat) _Λ which consists of 50 to 75 percent by weight of vinyl ß-hydroxyäthylcarbamylmethylearbamat units as the synthetic polymer. 909812/0912