US2494055A - Hardening of photographic sttver - Google Patents
Hardening of photographic sttver Download PDFInfo
- Publication number
- US2494055A US2494055A US71535146A US2494055A US 2494055 A US2494055 A US 2494055A US 71535146 A US71535146 A US 71535146A US 2494055 A US2494055 A US 2494055A
- Authority
- US
- United States
- Prior art keywords
- gelatin
- hardening
- photographic
- nitro
- silver
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000839 emulsion Substances 0.000 claims description 36
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 claims description 33
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 27
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 108010010803 Gelatin Proteins 0.000 description 30
- 239000008273 gelatin Substances 0.000 description 30
- 229920000159 gelatin Polymers 0.000 description 30
- 235000019322 gelatine Nutrition 0.000 description 30
- 235000011852 gelatine desserts Nutrition 0.000 description 30
- -1 SILVER HALIDE Chemical class 0.000 description 12
- 229960001755 resorcinol Drugs 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000032683 aging Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- OLQJQHSAWMFDJE-UHFFFAOYSA-N 2-(hydroxymethyl)-2-nitropropane-1,3-diol Chemical compound OCC(CO)(CO)[N+]([O-])=O OLQJQHSAWMFDJE-UHFFFAOYSA-N 0.000 description 2
- YADISKICBOYXFS-UHFFFAOYSA-N 2-ethyl-2-nitropropane-1,3-diol Chemical compound CCC(CO)(CO)[N+]([O-])=O YADISKICBOYXFS-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- IXWOUPGDGMCKGT-UHFFFAOYSA-N 2,3-dihydroxybenzaldehyde Chemical class OC1=CC=CC(C=O)=C1O IXWOUPGDGMCKGT-UHFFFAOYSA-N 0.000 description 1
- YTIXGBHAPNMOKU-UHFFFAOYSA-N 2-nitropropane-1,3-diol Chemical compound OCC(CO)[N+]([O-])=O YTIXGBHAPNMOKU-UHFFFAOYSA-N 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000000586 desensitisation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/30—Hardeners
Definitions
- a 2 invention relates to photographic gelatin: The foregoing objects are accomplished, ac-- and more particularly to the hardening of photocording-to the present invention, by incorporatinggraphic gelatin and gelatino silver halideemulin the gelatin or gelatinosilver-halide emulsion, a,
- compositions having: an appreciable primary aliphatic nitro alcohol of not more than increase melting point good stability on" ficarbon atoms; with or'withou-t other compounds ageing with respect to fog, speed, and gradation. which alone possess little or nohardening effect IIEn the preparation of: photographic gelatin disupon gelatin or gelatino silver-halide emulsions, persions and gelatino silver-halide emulsions, it u n" o ju i h" the nitrO alcohol 910061- has been the practice to treat the dispersions and e et th h d i action h e elimination emulsions, prior to coating, with a hardening h af a and also inhibit the agent so as toreduce the-tendency of the gelatin derlcy of the photograp m t to f O to soften, or to distend during processing of the fi photo'graphic material containing the gelatin,
- a still further object is to plQvide a gelatino as inphotographicproperties obtained.
- This compound does not detract in the slightest from the hardening effect obtained with the other components and rather surprisingly in cooperation with said other ingredients confers upon the final sensitized emulsions a very excellent stability on ageing with respect to fog, speed and gradation. While, therefore, the invention contemplates the utilization of the nitro alcohols alone to'effect hardening while avoiding the phenomenon of afterhardening," it likewise contemplates the employment with the nitro alcohols of 2,4-dihydroxy benzaldehyde and resorcinol either alone or together. Inasmuch as best results are obtained when all three components are employed, the use of the same represents the preferred embodiment of the invention.
- 2,4-dihydroxy benzaldehyde is the only one to accelerate the hardening effect of the nitro alcohol without impairing the photographic characteristics of the emulsions
- resorcinol was found to be the only one, when in an admixture with a nitro alcohol and 2.4-dihydroxy benzaldehyde, to act as a stabilizing agent so as to impart excellent stability to the emulsion with respect to fog, speed, and gradation.
- a sufficient quantity of the nitro alcohol alone is added. While the exact amount of the nitro alcohol may be varied within wide limits and with due regard to the particular type of gelatin dispersion employed, in general, amounts ranging from 0.05% to 2.5% based on the dry weight of gelatin in the dispersion are preferred. In these amounts, effective hardening is obtained without after-hardening, i. e., the melting point of the gelatin does not vary with time or with long periods of storage prior to actual use and processing of the photographic material provided with such a layer.
- a mixture of the nitro alcohol and 2,4-dihydroxy benzaldehyde is employed.
- the amount of 2,4-dihydroxy benzaldehyde, to be added to the preceding amounts of the nitro alcohol, may vary from 0.005% to 2.5%based on the dry weight of gelatin- -m" hardening gelatin emulsions ⁇ . which are. slightly alkaline, i.
- amounts of the nitro alcohol, 2,4-dihydroxy benzaldehyde, and recorcinol may also be varied within wide limits depending largely upon the desired degree of hardening, stabilizing effect, and gradation.
- the amounts of' the nitro alcohol may vary from 1 to 5 parts by weight
- the amount of 2,4-dihydroxy benzaldehyde may vary ,from 0.1 to 5 parts by weight
- the amount of resorcinol may vary from 1 to 10 parts by weight per 10 kilogram of emulsion containing 23-10% gelatin.
- lresorcinol in conjunction with the nitro alcohol and 2,4-dihydroxy benzaldehyde. It is to be understood, however, that these emulsions may also be hardened by mixing therewith prior to coating the nitro alcohol alone or in combination with 2,4-dihydroxy benzaldehyde. In the latter case the melting point of the gelatin rises appreciably without the attendant serious loss of photographic characteristics.
- EXAIWPLE I EXAMPLE II Twenty mls. of a 5% aqueous solution of 2- ethyl-2-nitro-1,3-propanediol and 80 mls. of a 5% aqueous solution of 2,4-dihydroxy benzaldehyde were added to 10 kilograms of a photographic silver-halide emulsion, containing 840%- gelatin and melting at 0., at a temperature of 40 C. A glass plate was coated with a thin layer of this emulsion and dried at room temperature. The emulsion layer melted at 47 0., and the film was tougher than the film of Example I.
- EXAMPLE III This example graphically illustrates the results of incorporating tris-(hydroxymethyl) nitromethane, 2,4-,-dihydroxy benzaldehyde and resor cinol in an X-ray emulsion containing 840% j gelatin whereby not only the melting point of the gelatin is increased but excellent photographic properties are obtained. All the parts are in per cent by weight based on the weight of the emulsion.
- EXAMPLE IV This example shows the effect. of fog jin a silverhalide emulsion containing .8-10%..igelatin'.by a; j mixturefot 2-nitro-1,3j-propanedio1, 2,4 dihydroxy' j 18 benzaldehyde, and resorcinol. All parts are in" per cent based on the dry weight of the gelatin in the emulsion.
- my invention is not only applicable to the preparation of photographic silver-halide emulsions of satisfactory hardening properties, but also to the preparation of gelatin dispersions and dispersions of gelatin substitutes, which are normally capable of being hardened with formaldehyde, especially those which are and have been used in the preparation of various coatings or layers on paper, cloth, film, glass, and other surfaces.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Jan. 10, 1950 UNlTED STATE-Sf PATENT OFFICE,-
'' HARDENING, or rnoroeimemo SILVER HALIDE" GELATIN EMULSIONS WITH NITRO .ALooHoEs Bernard A. Orkin, Woodbury, N.. .I'.,. assignor to General Aniline & Film Corporation, N ew- York,-
N. Y., a corporation of Delaware No Drawing. Application December 1-0, 1946-,
' Serial No. 715,351
4 Claims (01. 95-7) 1 a 2 invention relates to photographic gelatin: The foregoing objects are accomplished, ac-- and more particularly to the hardening of photocording-to the present invention, by incorporatinggraphic gelatin and gelatino silver halideemulin the gelatin or gelatinosilver-halide emulsion, a,
sions to yield compositions having: an appreciable primary aliphatic nitro alcohol of not more than increase melting point good stability on" ficarbon atoms; with or'withou-t other compounds ageing with respect to fog, speed, and gradation. which alone possess little or nohardening effect IIEn the preparation of: photographic gelatin disupon gelatin or gelatino silver-halide emulsions, persions and gelatino silver-halide emulsions, it u n" o ju i h" the nitrO alcohol 910061- has been the practice to treat the dispersions and e et th h d i action h e elimination emulsions, prior to coating, with a hardening h af a and also inhibit the agent so as toreduce the-tendency of the gelatin derlcy of the photograp m t to f O to soften, or to distend during processing of the fi photo'graphic material containing the gelatin, As ampl s of su ta p ima a p i i particularly at-temperatures higherthan the tem alcohols of notmore than 6 carbon atoms, the perature specified for processing' the particular 5 follOWing are illustrative photographic material. Compounds which have g H been used for hardening gelatin as such or in silver-halide emulsions are formaldehyde, hy- HOCH2 CH20H droxy aldehydes, acrolein, glyoxal, and derivatives N02 thereof, and mixtures oi an aliphatic aldehyde 9!- -ni ,3 p p 0 with an aromatic compound containing at least CH '5 one nuclear hydroxy substituent group such as phenol, resorcinol, resorcyclic aldehyde, and the I cflnrfiyflcmoiH like: Although formaldehyde and hydroxy alde- N02 hydes are satisfactoryas hardening agents, these 5': I 2.methy1: 2 nitm.1.propan01 compounds possess the undesirable property 0t i producing excessive fog, desensitization, or flat- $2135 toning of. gradation in the processed film. Any noom-o-omon hardeners thatfunction by the liberation. of N formaldehyde will. also have these deleterious eliects as well. as thatof "after'-hardening.- z'etlhym'mtmlgpmpanedufl Aliphatic aldehydes, with an aromatic compound I onion containing at least one nuclear hydroxy substi- I H0CH2CNO2. tuent group, 1nduce some increase in the melting point. They fail, however, to give. both an ape OHZQH preciable increase in the melting point and g0o d Tnsqm'dmxymethyl)mtmmethane stability upon ageing in respect to fog, speed, and l jg cmcncmog gradation. Q It isan object of the present invention. to pro- I t 2 vide a photographic gelatin or a gelatino silver- 2'mtro'l'butanol al d emulsion having an appreciable higher. The compounds which alone possess little melting point and much better stability on ag'e-. 013110 hardening effect on gelatin or gelatino' m than gelatin or gelatin) silver-halide emu}; silver-halide emulsions, and which may be added: PP Per V I, I in conjunction with the nitro alcohol, are 2,l di f .Another obiect is to provide gelatin-layers and '45s" hydrpxy benzaldehyde (resorcylic aldehyde)" and gel'atino silver-halide emulsion layers in which the I 1,3 b dio1- (res r inol) The function of gelatin is not subject to the phenomenon known; 2 4; y be'nzaldehyde in the mixture is as after-hardening. boost or accelerate the hardening action of the A f r her Object i to provid a el tino si1ver-' nitro alcohol. When resorcinol is added to this halide emulsion which will not fog on storage. at! ombination, the optimum in hardening as well A still further object is to plQvide a gelatino as inphotographicproperties obtained. Avery; silver -halide emulsion wi l'l'be resistant' to desirable increase in melting point of gelatin or relatively high. processing temperatures witho gllaj tinosilver halide' emulsions is obtained bv fogging; loss of speed, and'lossof gradation. the-{utilization of" nitrofalcohols alone, said in -('Jther objects will appear hereinafter. crease'in melting point being'unaccompa-niedby any tendency for the gelatin or emulsion to undergo the phenomenon of after-hardening. It has been found that the nitro alcohols depress the speed and gradation of the photographic emulsions a slight amount. Such losses, however, are more than compensated for by the valuable contributions made by the use of the nitro alcohols. Furthermore, if with the nitro alcohols there be added 2,4-dihydroxy benzaldehyde, greater hardness is obtained, the ZAL-dihydroxyv benzaldehyde operating as it were to accelerate the hardness attributable to the nitro alcohols. The 2,4-dihydroxy benzaldehyde in addition has the valuable property of reducing the losses in speed and gradation which accompany the use of the nitro alcohols. The results obtained with the nitro alcohols in admixture with the 2,4-dihydroxy benzaldehyde are greatly improved if there also be employed resorcinol. This compound does not detract in the slightest from the hardening effect obtained with the other components and rather surprisingly in cooperation with said other ingredients confers upon the final sensitized emulsions a very excellent stability on ageing with respect to fog, speed and gradation. While, therefore, the invention contemplates the utilization of the nitro alcohols alone to'effect hardening while avoiding the phenomenon of afterhardening," it likewise contemplates the employment with the nitro alcohols of 2,4-dihydroxy benzaldehyde and resorcinol either alone or together. Inasmuch as best results are obtained when all three components are employed, the use of the same represents the preferred embodiment of the invention.
It is to be noted that from the large class of dihydroxy benzaldehydes, 2,4-dihydroxy benzaldehyde is the only one to accelerate the hardening effect of the nitro alcohol without impairing the photographic characteristics of the emulsions, and from the large class of aromatic hydroxy compounds containing at least 1 nuclear hydroxy group, resorcinol was found to be the only one, when in an admixture with a nitro alcohol and 2.4-dihydroxy benzaldehyde, to act as a stabilizing agent so as to impart excellent stability to the emulsion with respect to fog, speed, and gradation.
Where it is desired to increase the melting point of the gelatin in a gelatin dispersion utilized in the preparation of non-curling layers, filter and anti-halation layers, or anti-abrasion layers, a sufficient quantity of the nitro alcohol alone is added. While the exact amount of the nitro alcohol may be varied within wide limits and with due regard to the particular type of gelatin dispersion employed, in general, amounts ranging from 0.05% to 2.5% based on the dry weight of gelatin in the dispersion are preferred. In these amounts, effective hardening is obtained without after-hardening, i. e., the melting point of the gelatin does not vary with time or with long periods of storage prior to actual use and processing of the photographic material provided with such a layer.
In cases, especially in anti-abrasion layers, where the optimum in hardness is desired, a mixture of the nitro alcohol and 2,4-dihydroxy benzaldehyde is employed. The amount of 2,4-dihydroxy benzaldehyde, to be added to the preceding amounts of the nitro alcohol, may vary from 0.005% to 2.5%based on the dry weight of gelatin- -m" hardening gelatin emulsions}. which are. slightly alkaline, i. e., emulsions having a pa greater than 7, generally between 7 and .5 t he exact amounts of the nitro alcohol, 2,4-dihydroxy benzaldehyde, and recorcinol may also be varied within wide limits depending largely upon the desired degree of hardening, stabilizing effect, and gradation. In general, the amounts of' the nitro alcohol may vary from 1 to 5 parts by weight, the amount of 2,4-dihydroxy benzaldehyde may vary ,from 0.1 to 5 parts by weight, and the amount of resorcinol may vary from 1 to 10 parts by weight per 10 kilogram of emulsion containing 23-10% gelatin.
Where it is desired to increase the speed and gradation of a silver-halide emulsion, I prefer to use lresorcinol in conjunction with the nitro alcohol and 2,4-dihydroxy benzaldehyde. It is to be understood, however, that these emulsions may also be hardened by mixing therewith prior to coating the nitro alcohol alone or in combination with 2,4-dihydroxy benzaldehyde. In the latter case the melting point of the gelatin rises appreciably without the attendant serious loss of photographic characteristics.
While the following examples describe in detail the methods for accomplishing the afore: stated objects, it is to be understood that'they are given merely for the purpose of illustration and are not to be construed as limiting the scope of the invention.
EXAIWPLE I EXAMPLE II Twenty mls. of a 5% aqueous solution of 2- ethyl-2-nitro-1,3-propanediol and 80 mls. of a 5% aqueous solution of 2,4-dihydroxy benzaldehyde were added to 10 kilograms of a photographic silver-halide emulsion, containing 840%- gelatin and melting at 0., at a temperature of 40 C. A glass plate was coated with a thin layer of this emulsion and dried at room temperature. The emulsion layer melted at 47 0., and the film was tougher than the film of Example I.
EXAMPLE III This example graphically illustrates the results of incorporating tris-(hydroxymethyl) nitromethane, 2,4-,-dihydroxy benzaldehyde and resor cinol in an X-ray emulsion containing 840% j gelatin whereby not only the melting point of the gelatin is increased but excellent photographic properties are obtained. All the parts are in per cent by weight based on the weight of the emulsion.
X-ra'y' emulsion Quantity oi Tris-(hydroxymetliyDmitromethane. 0. 023 Quantity of 2, -Dihydrow-benzaldehyde 0 0. 03 Quantity'of Besorcinol 0 O. 07 M. P.,G.; 47 Fog 0. 16 Speed '196 Gradation O.
EXAMPLE IV This example shows the effect. of fog jin a silverhalide emulsion containing .8-10%..igelatin'.by a; j mixturefot 2-nitro-1,3j-propanedio1, 2,4 dihydroxy' j 18 benzaldehyde, and resorcinol. All parts are in" per cent based on the dry weight of the gelatin in the emulsion.
2-Nitro-1,3- 2,4-Dih ydroxy Resor- Fog propanediol benzaldehyde cinol Value 0 O 0 0. 20 0. 1 O. 2 0. 3 0. l6 0. 2 0. 2 0. 8 0. 16 0. 2 (l, 4 0v 6 0. 14 0.2 0.12 0. 48 0.12 0. 2 0. 24 0. 36 0. 10
From the foregoing examples, it is clearly apparent that my invention is not only applicable to the preparation of photographic silver-halide emulsions of satisfactory hardening properties, but also to the preparation of gelatin dispersions and dispersions of gelatin substitutes, which are normally capable of being hardened with formaldehyde, especially those which are and have been used in the preparation of various coatings or layers on paper, cloth, film, glass, and other surfaces.
I claim:
1. A photo-sensitive element containing a photographic gelatino silver-halide emulsion layer hardened by means of a primary aliphatic nitro alcohol of 3 to 6 carbon atoms, 2,4-dihydroxy benzaldehyde, and resorcinol.
2. A photo-sensitive element containing a photographic gelatino silver-halide emulsion layer hardened by means of tris-(hydroxymethyl) -nitromethane, 2,4-dihydroxy benzaldehyde, and resorcinol.
3. A photo-sensitive element containing a photographic gelatino silver-halide emulsion layer hardened by means of 2-ethyl-2-nitro-1,3-propanediol, 2,4-dihydroxy benzaldehyde, and resorcinol.
4. A photo-sensitive element containing a photographic gelatino silver-halide emulsion layer hardened by means of 2-nitro-1,3-propanediol, ZA-dihydroxy benzaldehyde, and resorcinol.
BERNARD A. ORKIN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,165,421 Sheppard et al. July 11, 1939 2,206,819 Martin July 2, 1940 2,426,128 Trowell -1 Aug. 19, 1947
Claims (1)
1. A PHOTO-SENSITIVE ELEMENT CONTAINING A PHOTOGRAPHIC GELATINO SILVER-HALIDE EMULSION LAYER HARDENED BY MEANS OF A PRIMARY ALIPHATIC NITRO ALCOHOL OF 3 TO 6 CARBON ATOMS, 2,4-DIHYDROXY BENZALDEHYDE, AND RESORCINOL.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71535146 US2494055A (en) | 1946-12-10 | 1946-12-10 | Hardening of photographic sttver |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71535146 US2494055A (en) | 1946-12-10 | 1946-12-10 | Hardening of photographic sttver |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2494055A true US2494055A (en) | 1950-01-10 |
Family
ID=24873680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US71535146 Expired - Lifetime US2494055A (en) | 1946-12-10 | 1946-12-10 | Hardening of photographic sttver |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2494055A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2629659A (en) * | 1948-12-07 | 1953-02-24 | Gen Aniline & Film Corp | Process of hardening gelatino silver halide emulsions |
| US2635048A (en) * | 1948-07-06 | 1953-04-14 | Polaroid Corp | Photographic transfer product and process |
| US3012886A (en) * | 1954-05-10 | 1961-12-12 | Harry H Lerner | Emulsion coating and method of preparation |
| DE1145932B (en) * | 1957-03-11 | 1963-03-21 | James Martin | Multiple connection device for lines leading to the clothing of aircraft personnel |
| US3464821A (en) * | 1963-06-05 | 1969-09-02 | Eastman Kodak Co | Colloid transfer activator containing a formaldehyde generating compound |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2165421A (en) * | 1936-09-25 | 1939-07-11 | Eastman Kodak Co | Hardening photographic emulsions |
| US2206819A (en) * | 1939-01-28 | 1940-07-02 | Commercial Solvents Corp | Prolamin solutions and method of preparing same |
| US2426128A (en) * | 1940-12-18 | 1947-08-19 | Hercules Powder Co Ltd | Plastic compositions made with trimethylolnitromethane |
-
1946
- 1946-12-10 US US71535146 patent/US2494055A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2165421A (en) * | 1936-09-25 | 1939-07-11 | Eastman Kodak Co | Hardening photographic emulsions |
| US2206819A (en) * | 1939-01-28 | 1940-07-02 | Commercial Solvents Corp | Prolamin solutions and method of preparing same |
| US2426128A (en) * | 1940-12-18 | 1947-08-19 | Hercules Powder Co Ltd | Plastic compositions made with trimethylolnitromethane |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2635048A (en) * | 1948-07-06 | 1953-04-14 | Polaroid Corp | Photographic transfer product and process |
| US2629659A (en) * | 1948-12-07 | 1953-02-24 | Gen Aniline & Film Corp | Process of hardening gelatino silver halide emulsions |
| US3012886A (en) * | 1954-05-10 | 1961-12-12 | Harry H Lerner | Emulsion coating and method of preparation |
| DE1145932B (en) * | 1957-03-11 | 1963-03-21 | James Martin | Multiple connection device for lines leading to the clothing of aircraft personnel |
| US3464821A (en) * | 1963-06-05 | 1969-09-02 | Eastman Kodak Co | Colloid transfer activator containing a formaldehyde generating compound |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2586168A (en) | Process of hardening gelatin and photographic gelatin emulsions | |
| US2983611A (en) | Gelatin compositions containing hardeners | |
| US2992109A (en) | Hardening of photographic emulsions | |
| US2240472A (en) | Photographic gelatin layer containing a di-(polyalkylene glycoxy) alkane | |
| US2059817A (en) | Hardening photographic gelatin emulsions and solutions | |
| US2494055A (en) | Hardening of photographic sttver | |
| US3232764A (en) | Gelatin compositions adapted for the preparation of hardened coatings | |
| US2418613A (en) | Fog inhibitors for photographic emulsions | |
| US2165421A (en) | Hardening photographic emulsions | |
| US3043697A (en) | Photographic gelatin-n-vinyllactam silver halide emulsions containing phenolic antifoggants | |
| US2629659A (en) | Process of hardening gelatino silver halide emulsions | |
| US2725295A (en) | Hardening of gelatin with organic acid chlorides | |
| US2964404A (en) | Hardening of gelating with aziridinylsulfonyl compounds | |
| US2553506A (en) | Hardened gelatino-silver halede | |
| US2450397A (en) | 5-hydroxy-1, 3, 4-triazaindolizines as stabiliziers for photographic silver-halide emulsions | |
| US2080019A (en) | Hardening photographic emulsion | |
| US2367511A (en) | Photographic emulsions | |
| US2725294A (en) | Hardening of gelatin with polyanhydrides | |
| US2593912A (en) | Photographic film containing hardened gelatin | |
| US2776219A (en) | Gelatin coating solution for film support | |
| US3291624A (en) | Acetylated derivatives of dialdehydes and of their hemiacetals as gelatin hardeners | |
| US3420667A (en) | Substituted quinones and dimine quinones as silver halide sensitizers | |
| US2372873A (en) | Hardening of gelatin | |
| US2245236A (en) | Method of increasing infrared sensitivity | |
| US3640721A (en) | Gelatinous photographic coating composition |