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US4060420A Expired / Lapsed US ⏱️ 0.0 years remaining

Sulfonylacetate activator-stabilizer precursor

Assignee: Eastman Kodak Co
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Filing: 1976-08-06
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Granted: 1977-11-29
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Expires: 1996-08-06
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Abstract

Abstract An activator-stabilizer precursor compound having an acid portion which is an alpha-sulfonylacetate is useful in a photographic composition which is responsive to heat for processing. The activator-stabilizer precursors are characterized in that their acid byproducts have reduced toxicity and volatility and are substantially inert in a processed photographic element.

Inventors

  • 👤 Paul Barrett Merkel
  • 👤 Hans Gway Ling

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 10:57
CPC Classifications
G; G03; G03C; G03C1/00; G03C1/005; G03C1/06; G03C1/43; Y; Y10; Y10S; Y10S430/00; Y10S430/156

Claims Analysis

Total Claims: 36
Claim 1
Independent Claim 58 words
In a heat developable and heat stabilizable photographic element comprising a support having thereon, in reactive association, (a) a photographic silver salt, (b) a photographic silver salt developing agent, (c) a binder, and (d) a stabilizing concentration of an activator-stabilizer precursor having a base portion and an acid portion the improvement wherein said acid portion is an alpha-sulfonylacetate.
Claim 2
Dependent Claim 58 words
In a heat developable and heat stabilizable photographic element comprising a support having thereon, in reactive association, (a) a photographic silver salt, (b) a photographic silver salt developing agent, (c) a binder, and (d) a stabilizing concentration of an activator-stabilizer precursor having a base portion and an acid portion the improvement wherein said acid portion is an alpha-sulfonylacetate.
Claim 3
Dependent Claim 70 words
A heat developable and heat stabilizable photographic element comprising a support having thereon in reactive association (a) a photographic silver salt, (b) a photographic silver salt developing agent, (c) a binder, and (d) a stabilizing concentration of an activator-stabilizer precursor represented by the formula: Q.sub.m A.sub.w wherein Q is a protonated basic nitrogen containing moiety; A is an alpha-sulfonylacetate; m is 1 to 4 and w is 1 to 2.
Claim 4
Dependent Claim 70 words
A heat developable and heat stabilizable photographic element comprising a support having thereon in reactive association (a) a photographic silver salt, (b) a photographic silver salt developing agent, (c) a binder, and (d) a stabilizing concentration of an activator-stabilizer precursor represented by the formula: Q.sub.m A.sub.w wherein Q is a protonated basic nitrogen containing moiety; A is an alpha-sulfonylacetate; m is 1 to 4 and w is 1 to 2.
Claim 5
Dependent Claim 88 words
The element of claim 2 wherein A is an alphasulfonylacetate represented by the formula: ##STR17## wherein w is 1 or 2; R 1 is alkyl containing 1 to 6 carbon atoms, aryl containing 5 to 10 carbon atoms or carboxymethyl when w is 1, and alkylene containing 1 to 6 carbon atoms, alkylidene, or arylene containing 6 to 10 carbon atoms when w is 2; R 2 and R 3 individually are hydrogen, alkyl containing 1 to 6 carbon atoms or aryl containing 6 to 10 carbon atoms.
Claim 6
Dependent Claim 152 words
The element of claim 2 wherein Q is selected from the group consisting of the following formulas: ##STR18## wherein Y is alkylene containing 2 or 3 chain carbon atoms, X is SR 7 or NHR 8 , wherein R 7 is aminoalkyl containing 2 to 6 carbon atoms, and R 8 is hydrogen, alkyl containing 1 to 20 carbon atoms, phenyl, or aminoalkyl containing 2 to 6 carbon atoms; p is 1 or 2; when p is 1, Z is ##STR19## when p is 2, Z is a divalent linking group selected from the group consisting of ##STR20## R 6 is alkylene containing 2 to 12 carbon atoms, or phenylene; R 5 and R 4 are individually selected from the group consisting of hydrogen, alkyl containing 1 to 6 carbon atoms, or R 5 and R 4 taken together represent alkylene containing 2 or 3 carbon atoms; y is 1 to 8.
Claim 7
Dependent Claim 49 words
The element of claim 1 wherein the activator-stabilizer precursor has the properties of releasing a byproduct by decarboxylation upon heating and undergoes less than 10% weight loss in a thermogravimetric scan between about 30° C and about 180° C where the scan rate is about 40° C per minute.
Claim 8
Dependent Claim 20 words
The element of claim 1 wherein said acid portion is selected from the group consisting of ethylenebis(sulfonylacetate), methylenebis(sulfonylacetate) and phenylsulfonylacetate.
Claim 9
Dependent Claim 14 words
The element of claim 1 wherein the activator-stabilizer precursor consists essentially of bis(2-amino-2-thiazoline) methylene(sulfonylacetate).
Claim 10
Dependent Claim 14 words
The element of claim 1 wherein the activator-stabilizer precursor consists essentially of N-(2-thiazoline)-N'-(imidazoline)ethylenediamine ethylenebis(sulfonylacetate).
Claim 11
Dependent Claim 14 words
The element of claim 1 wherein the activator-stabilizer precursor consists essentially of 1,3-bis[2S-(N,N'-ethyleneisothiourea)ethyl]urea ethylenebis(sulfonylacetate.
Claim 12
Dependent Claim 14 words
The element of claim 1 wherein the photographic silver salt is photographic silver halide.
Claim 13
Dependent Claim 29 words
The element of claim 1 wherein the stabilizing concentration of the activator-stabilizer precursor is 0.2 to 4 moles of the activator-stabilizer precursor per mole of the photographic silver salt.
Claim 14
Dependent Claim 46 words
A heat developable and heat stabilizable photographic element comprising a support having thereon a layer comprising in reactive association (a) photographic silver halide, (b) a 3-pyrazolidone silver halide developing agent, (c) a polymeric binder, and (d) a stabilizing concentration of an activator-stabilizer precursor comprising bis(2-amino-2-thiazoline) methylene(sulfonylacetate).
Claim 15
Dependent Claim 46 words
A heat developable and heat stabilizable photographic element comprising a support having thereon a layer comprising in reactive association (a) photographic silver halide, (b) a 3-pyrazolidone silver halide developing agent, (c) a polymeric binder, and (d) a stabilizing concentration of an activator-stabilizer precursor comprising bis(2-amino-2-thiazoline) methylene(sulfonylacetate).
Claim 16
Dependent Claim 46 words
A heat developable and heat stabilizable photographic element comprising a support having thereon a layer comprising in reactive association (a) photographic silver halide, (b) a 3-pyrazolidone silver halide developing agent, (c) a polymeric binder and (d) a stabilizing concentration of an activator-stabilizer precursor comprising N-(2-thiazolino)-N'-(imidazolino)ethylenediamine ethylenebis(sulfonylacetate).
Claim 17
Dependent Claim 46 words
A heat developable and heat stabilizable photographic element comprising a support having thereon a layer comprising in reactive association (a) photographic silver halide, (b) a 3-pyrazolidone silver halide developing agent, (c) a polymeric binder and (d) a stabilizing concentration of an activator-stabilizer precursor comprising N-(2-thiazolino)-N'-(imidazolino)ethylenediamine ethylenebis(sulfonylacetate).
Claim 18
Dependent Claim 48 words
In a heat developable and heat stabilizable photographic composition comprising (a) a photographic silver salt, (b) a photographic silver salt developing agent and (c) a stabilizing concentration of an activator-stabilizer precursor having an acid portion and a base portion the improvement wherein said acid portion is an alpha-sulfonylacetate.
Claim 19
Dependent Claim 48 words
In a heat developable and heat stabilizable photographic composition comprising (a) a photographic silver salt, (b) a photographic silver salt developing agent and (c) a stabilizing concentration of an activator-stabilizer precursor having an acid portion and a base portion the improvement wherein said acid portion is an alpha-sulfonylacetate.
Claim 20
Dependent Claim 65 words
A heat developable and heat stabilizable photographic composition comprising (a) a photographic silver salt, (b) a photographic silver salt developing agent, and (c) a stabilizing concentration of an activator-stabilizer precursor represented by the formula: Q.sub.m A.sub.w wherein Q is a protonated basic nitrogen containing moiety; A is an alpha-solfonylacetate; m is an integer from 1 to 4 and w is an integer 1 to 2.
Claim 21
Dependent Claim 65 words
A heat developable and heat stabilizable photographic composition comprising (a) a photographic silver salt, (b) a photographic silver salt developing agent, and (c) a stabilizing concentration of an activator-stabilizer precursor represented by the formula: Q.sub.m A.sub.w wherein Q is a protonated basic nitrogen containing moiety; A is an alpha-solfonylacetate; m is an integer from 1 to 4 and w is an integer 1 to 2.
Claim 22
Dependent Claim 88 words
The composition of claim 15 wherein A is an alpha-sulfonylacetate represented by the formula: ##STR21## wherein w is 1 or 2; R 1 is alkyl containing 1 to 6 carbon atoms, aryl containing 5 to 10 carbon atoms or carboxymethyl when w is 1, and alkylene containing 1 to 6 carbon atoms, alkylidene, or arylene containing 6 to 10 carbon atoms when w is 2; R 2 and R 3 individually are hydrogen, alkyl containing 1 to 6 carbon atoms or aryl containing 6 to 10 carbon atoms.
Claim 23
Dependent Claim 152 words
The composition of claim 15 wherein Q is selected from the group consisting of the following formulas: ##STR22## wherein Y is alkylene containing 2 or 3 chain carbon atoms, X is SR 7 or NHR 8 , wherein R 7 is aminoalkyl containing 2 to 6 carbon atoms, and R 8 is hydrogen, alkyl containing 1 to 20 carbon atoms, phenyl, or aminoalkyl containing 2 to 6 carbon atoms; p is 1 or 2; when p is 1, Z is ##STR23## when p is 2, Z is a divalent linking group selected from the group consisting of ##STR24## R 6 is alkylene containing 2 to 12 carbon atoms, or phenylene; R 5 and R 4 are individually selected from the group consisting of hydrogen, alkyl containing 1 to 6 carbon atoms, or R 5 and R 4 taken together represent alkylene containing 2 or 3 carbon atoms; y is 1 to 8.
Claim 24
Dependent Claim 48 words
The composition of claim 15 wherein the activator-stabilizer precursor has the properties of releasing a byproduct by decarboxylation upon heating and undergoes less than 10% weight loss in a thermogravimetric scan between about 30° and about 180° C where the scan rate is about 40° C per minute.
Claim 25
Dependent Claim 20 words
The composition of claim 15 wherein said acid portion is selected from the group consisting of ethylenebis(sulfonylacetate), methylenebis(sulfonylacetate) and phenylsulfonylacetate.
Claim 26
Dependent Claim 14 words
The composition of claim 15 wherein the activator-stabilizer precursor consists essentially of bis(2-amino-2-thiazoline) methylene(sulfonylacetate).
Claim 27
Dependent Claim 14 words
The composition of claim 15 wherein the activator-stabilizer precursor consists essentially of N-(2-thiazolino-N'-(imidazolino)ethylenediamine ethylene-bis(sulfonylacetate.
Claim 28
Dependent Claim 15 words
The composition of claim 15 wherein the activator-stabilizer precursor consists essentially of 1,3-bis[2S-(N,N'-ethyleneisothiourea)ethyl]urea ethylenebis(sulfonylacetic acid).
Claim 29
Dependent Claim 29 words
The composition of claim 15 wherein the stabilizing concentration of the activator-stabilizer precursor is 0.2 to 4 moles of the activator-stabilizer precursor per mole of the photographic silver salt.
Claim 30
Dependent Claim 80 words
A heat activatable photographic silver salt processing composition comprising a silver salt developing agent and an activator-stabilizer precursor wherein said stabilizer precursor has the formula: Q.sub.m A.sub.w wherein Q is a protonated basic nitrogen containing moiety; A is an alpha-sulfonylacetate; m is an integer from 1 to 4 and w is an integer 1 to 2 and wherein said precursor is present in the composition in a concentration sufficient to stabilize a silver halide image when said composition is heated.
Claim 31
Dependent Claim 80 words
A heat activatable photographic silver salt processing composition comprising a silver salt developing agent and an activator-stabilizer precursor wherein said stabilizer precursor has the formula: Q.sub.m A.sub.w wherein Q is a protonated basic nitrogen containing moiety; A is an alpha-sulfonylacetate; m is an integer from 1 to 4 and w is an integer 1 to 2 and wherein said precursor is present in the composition in a concentration sufficient to stabilize a silver halide image when said composition is heated.
Claim 32
Dependent Claim 48 words
The processing composition of claim 24 wherein said developing agent comprises a phenolic silver halide developing agent and a 3-pyrazolidone silver halide developing agent and wherein said activator-stabilizer precursor is a compound selected from the group consisting of bis(2-amino-2-thiazoline) methylene(sulfonylacetate), N-(2-thiazolino)-N'-(imidazolino)ethylenediamine ethylenebis(sulfonylacetate), 1,3-bis[2S-(N,N'-ethyleneisothiourea)ethyl]urea ethylenebis(sulfonylacetic acid) and combinations thereof.
Claim 33
Dependent Claim 27 words
A heat activatable photographic silver salt processing composition comprising (a) a hydroquinone silver halide developing agent, (b) a 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone silver halide developing agent and (c) N-(2-thiazolino)-N'-(imidazolino)ethylenediamine ethylenebis(sulfonylacetate).
Claim 34
Dependent Claim 27 words
A heat activatable photographic silver salt processing composition comprising (a) a hydroquinone silver halide developing agent, (b) a 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone silver halide developing agent and (c) N-(2-thiazolino)-N'-(imidazolino)ethylenediamine ethylenebis(sulfonylacetate).
Claim 35
Dependent Claim 46 words
A method of developing and stabilizing an image in an exposed photographic element as defined in claim 1, after image wise exposure comprising heating said element to a temperature within the range of about 90° to about 200° C until an image is developed and stabilized.
Claim 36
Dependent Claim 16 words
The method of claim 27 wherein the element is heated for about 1 to 60 seconds.

References Cited (Backward Citations)

US3457078A Cited
US3649280A Cited
US3669670A Cited
US3955982A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-11-28 1981-05-30 1981-11-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-11-28 1985-05-30 1985-11-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-11-28 1989-05-30 1989-11-29 $7700.00 Window Closed / Lapsed

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