US3506449A - Gelatin coating compositions with n-tallow-beta-iminodipropionic acid - Google Patents
Gelatin coating compositions with n-tallow-beta-iminodipropionic acid Download PDFInfo
- Publication number
- US3506449A US3506449A US225108A US3506449DA US3506449A US 3506449 A US3506449 A US 3506449A US 225108 A US225108 A US 225108A US 3506449D A US3506449D A US 3506449DA US 3506449 A US3506449 A US 3506449A
- Authority
- US
- United States
- Prior art keywords
- coating
- tallow
- gelatin
- composition
- acid
- 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
- 108010010803 Gelatin Proteins 0.000 title description 19
- 229920000159 gelatin Polymers 0.000 title description 19
- 239000008273 gelatin Substances 0.000 title description 19
- 235000019322 gelatine Nutrition 0.000 title description 19
- 235000011852 gelatine desserts Nutrition 0.000 title description 19
- 239000008199 coating composition Substances 0.000 title description 14
- 238000000576 coating method Methods 0.000 description 51
- 239000011248 coating agent Substances 0.000 description 42
- 239000000203 mixture Substances 0.000 description 24
- 239000010410 layer Substances 0.000 description 15
- TXPKUUXHNFRBPS-UHFFFAOYSA-N 3-(2-carboxyethylamino)propanoic acid Chemical compound OC(=O)CCNCCC(O)=O TXPKUUXHNFRBPS-UHFFFAOYSA-N 0.000 description 6
- -1 alkali metal salts Chemical class 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000005018 casein Substances 0.000 description 5
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 5
- 235000021240 caseins Nutrition 0.000 description 5
- 230000007547 defect Effects 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000003760 tallow Substances 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BCXBRXMGDFMQHD-UHFFFAOYSA-N 2-hexadecyl-3-oxoicosanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)C(C(O)=O)CCCCCCCCCCCCCCCC BCXBRXMGDFMQHD-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- G03C1/38—Dispersants; Agents facilitating spreading
Definitions
- This invention relates to proteinaceous compositions such as of gelatin or casein, containing a coating aid of an alkyl derivative of iminodiacetic or iminodipropionic acid therein.
- the protein coatings either the photographic emulsion or other coatings, have both good surface slickness and good developer wettability
- a further object of this invention is to provide proteinaceous coating compositions containing alkali metal salts or alkyl derivatives of iminodiacetic acid and or iminodipropionic acid in which the alkyl radical is 12-18 carbon atoms. Other objects of this invention will appear herein.
- salts of alkyl derivatives of iminodiacetic or iminodipropionic acid are useful as coating aids in proteinaceous coating compositions giving layers having good surface slickness, good developer wettability, which compositions are useful for application either over a support or over a previous proteinaceous coating.
- coatings may be applied from three compositions which are substantially free of defects such as pencil line streaks, mottle and general streakiness such as frequently characterizes coatings especially in multiple layer hopper coating operations.
- R a 11-17 carbon hydrocarbon radical and M is a cation which will contribute to the water solubility of the coating aid and may be ammonium, sodium or some other alkali metal.
- coating aids such as the alkali metal or ammonium salts of N-tallow-fl-iminopropionic acid in which tallow has been used to supply the alkyl radical of the acid which comprises mainly C and C groupshexadecyl and octadecyl groups. See Feiser and Feiser, Introduction to Organic Chemistry, 1957, D. C. Heath and Company, page 295.
- Coating aids of this type may generally be prepared as known in the prior art and as disclosed in Bulletin 15'-A, Deriphats, General Mills Chemical Division, 1961, and in U.S. Patents 2,468,012 and 2,816,920. Tallow which can be used in the preparation, for example, may have as the relative proportions of the acid port on thereof 61% stearoyl (stearic acid), 6% palmitoyl (palmitic acid) and 33% oleyl (oleic acid). It has been found that in general the coating aid should be used in a concentration between about 0.2 and 2.7 parts per parts of the protein, e.g., gelatin or casein, in the composition.
- the protein compositions in accordance with this invention are useful for applying single layers they are especially useful in the laying down of a plurality of layers in a simultaneous coating operation in a multiple coating technique such as on the order of that described in U.S. Patent No. 2,761,791 of T. A. Russell. Coating operations of this type give coatings substantially free of defects.
- the plurality of layers may be applied in sequence such as by coating one layer over a previous gelatin or casein layer either by a wet-onwet coating operation or by a wet-on-dry procedure.
- EXAMPLE 1 There was applied simultaneously to paper by a multiple coating technique as described in U.S. Patent No. 2,761,791 a gelatin-silver halide photographic emulsion and an aqueous gelatin overcoating layer using as the coating aid in each composition the sodium salt of N- tallow iminodipropionic acid in concentrations from 0.07 to 0.5 gram per pound of composition.
- the resulting layers in each case exhibit good developer spreading and slickness values as compared to compositions in which no coating aid was used. Also the products exhibited freedom from streakiness and other similar coating defects,
- the developer wettability is determined by recording the area covered upon delivering one ml. of developer solution to a fiat section of a dried coating and measuring the area in square centimeters which is wet thereby.
- EXAMPLE 2 A wet-on-dry application was made of a dyed gelatin coating to film base as an antihalation layer.
- the coating aid used was the sodium salt of N-tallow iminodipropionic acid in the proportion of 0.22 gram per pound of gelatin overcoating composition.
- the resulting coating had a smooth surface and was substantially free of mottle or streakiness.
- EXAMPLE 3 Coatings of gelatin-silver halide photographic emulsion having therein as the coating aid a mixture of the disodium salts of N-tallow iminodipropionic acid and N- lauroyl carboxymethyl glycine were coated out onto paper.
- the ratios of the two coating aid materials were 3:1 and 1:3 respectively, the coating aid being present in each case in a concentration of 0.25 gram per pound of wet emulsion. In each case products were obtained having good surface slickness, good smoothness, good wettability with developer solution and freedom from surface defects.
- each pound of composition contains 37 grams of gelatin or casein.
- the coating aid is present in an amount within the range of about 1.9 to about 2.7 parts thereof per 100 parts of the gelatin or protein in the coating composition in which it is used.
- a coating solution for coating at least one layer of a photographic element comprising a proteinaceous composition and containing a wetting agent which comprises an alkali metal or ammonium salt of N-tallow-fi-iminodipropionic acid.
- a coating solution for coating at least one layer of a photographic element comprising a proteinaceous composition and containing a wetting agent which comprises disodium salt of N-tallow-fl-iminodipropionic acid.
- a coating solution according to claim 4 which comprises a silver halide composition.
- a photographic element comprising a support, at least one light-sensitive silver halide layer and at least one layer comprising a proteinaceous composition and containing a wetting agent comprising an alkali metal or ammonium salt of N-tallow-fl-iminodipropionic acid.
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- 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)
- Paints Or Removers (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
United States Patent 3,506,449 GELATIN COATING COMPOSITIONS WITH N-TAL- LOW-fi-IMINODIPROPIONIC ACID William J. Knox, Rochester, N.Y., assignor to Eastman Kodak Company, Rochester, N.Y., a corporation of New Jersey No Drawing. Filed Sept. 20, 1962, Ser. No. 225,108
Int. Cl. G03c 1/02; C09d 3/04 U.S. Cl. 96-94 9 Claims ABSTRACT OF THE DISCLOSURE This invention relates to proteinaceous coating compositions and photographic elements containing the same wherein said coating composition comprises the salt of N-tallow-fl-iminodipropionic acid,
This invention relates to proteinaceous compositions such as of gelatin or casein, containing a coating aid of an alkyl derivative of iminodiacetic or iminodipropionic acid therein.
In the photographic industry it is often desirable that the protein coatings, either the photographic emulsion or other coatings, have both good surface slickness and good developer wettability,
In the coating of film or paper with a gelatin layer such as of a photographic emulsion or some other gelatin coating composition, uniform application of the composition to the surface to which it is supplied is desirable especially at good production speeds. When no coating aid is used, defects such as repellencies, pencil line streaks or the like arise. Saponin has been employed, in this connectio; as a coating aid but this material has been found to vapy markedly from batch to batch in quality and composition. Not only may this adversely affect a photographic emul v sion containing it but in some instances only little or no improvement in coating properties may be obtained.
A number of synthetic materials have been suggested as coating aids in gelatin compositions and many of these materials have shown themselves to be useful in applying a gelatin coating to a surface. Sometimes, however, these coating aids have left something to be desired particularly in coating methods in which several coatings are applied to a support simultaneously such as in the manner described in U.S. Patent No. 2,761,791 of T. A. Russell.
One object of this invention is to provide proteinaceous coating compositions which yield blemish-free coatings having good surface slickness and developer wettability when those compositions are laid down as a layer upon a support. Another object of this invention is to provide gelatin and casein coating compositions which are useful when applied over paper or film base support or over a previous gelatin coating residing upon a support. A further object of this invention is to provide proteinaceous coating compositions containing alkali metal salts or alkyl derivatives of iminodiacetic acid and or iminodipropionic acid in which the alkyl radical is 12-18 carbon atoms. Other objects of this invention will appear herein.
It has now been found that salts of alkyl derivatives of iminodiacetic or iminodipropionic acid, the alkyl radical being of 12-18 carbon atoms, are useful as coating aids in proteinaceous coating compositions giving layers having good surface slickness, good developer wettability, which compositions are useful for application either over a support or over a previous proteinaceous coating, We have found that coatings may be applied from three compositions which are substantially free of defects such as pencil line streaks, mottle and general streakiness such as frequently characterizes coatings especially in multiple layer hopper coating operations.
3,506,449 Patented Apr. 14, 1970 The coating aids which I have found to be useful in proteinaceous compositions are those having the formula:
in which x=l2, R=a 11-17 carbon hydrocarbon radical and M is a cation which will contribute to the water solubility of the coating aid and may be ammonium, sodium or some other alkali metal. Of particular usefulness are those coating aids such as the alkali metal or ammonium salts of N-tallow-fl-iminopropionic acid in which tallow has been used to supply the alkyl radical of the acid which comprises mainly C and C groupshexadecyl and octadecyl groups. See Feiser and Feiser, Introduction to Organic Chemistry, 1957, D. C. Heath and Company, page 295.
Coating aids of this type may generally be prepared as known in the prior art and as disclosed in Bulletin 15'-A, Deriphats, General Mills Chemical Division, 1961, and in U.S. Patents 2,468,012 and 2,816,920. Tallow which can be used in the preparation, for example, may have as the relative proportions of the acid port on thereof 61% stearoyl (stearic acid), 6% palmitoyl (palmitic acid) and 33% oleyl (oleic acid). It has been found that in general the coating aid should be used in a concentration between about 0.2 and 2.7 parts per parts of the protein, e.g., gelatin or casein, in the composition.
Although the protein compositions in accordance with this invention are useful for applying single layers they are especially useful in the laying down of a plurality of layers in a simultaneous coating operation in a multiple coating technique such as on the order of that described in U.S. Patent No. 2,761,791 of T. A. Russell. Coating operations of this type give coatings substantially free of defects. Instead of a multiple layer operation in which the layers are simultaneously applied, the plurality of layers may be applied in sequence such as by coating one layer over a previous gelatin or casein layer either by a wet-onwet coating operation or by a wet-on-dry procedure.
The following examples illustrate coating procedures employing compositions in accordance with our invention:
EXAMPLE 1 There was applied simultaneously to paper by a multiple coating technique as described in U.S. Patent No. 2,761,791 a gelatin-silver halide photographic emulsion and an aqueous gelatin overcoating layer using as the coating aid in each composition the sodium salt of N- tallow iminodipropionic acid in concentrations from 0.07 to 0.5 gram per pound of composition. The resulting layers in each case exhibit good developer spreading and slickness values as compared to compositions in which no coating aid was used. Also the products exhibited freedom from streakiness and other similar coating defects, The developer wettability is determined by recording the area covered upon delivering one ml. of developer solution to a fiat section of a dried coating and measuring the area in square centimeters which is wet thereby.
EXAMPLE 2 A wet-on-dry application was made of a dyed gelatin coating to film base as an antihalation layer. The coating aid used was the sodium salt of N-tallow iminodipropionic acid in the proportion of 0.22 gram per pound of gelatin overcoating composition. The resulting coating had a smooth surface and was substantially free of mottle or streakiness.
EXAMPLE 3 Coatings of gelatin-silver halide photographic emulsion having therein as the coating aid a mixture of the disodium salts of N-tallow iminodipropionic acid and N- lauroyl carboxymethyl glycine were coated out onto paper. The ratios of the two coating aid materials were 3:1 and 1:3 respectively, the coating aid being present in each case in a concentration of 0.25 gram per pound of wet emulsion. In each case products were obtained having good surface slickness, good smoothness, good wettability with developer solution and freedom from surface defects.
In each of the examples given each pound of composition contains 37 grams of gelatin or casein. The coating aid is present in an amount within the range of about 1.9 to about 2.7 parts thereof per 100 parts of the gelatin or protein in the coating composition in which it is used.
I claim.
1. A coating solution for coating at least one layer of a photographic element comprising a proteinaceous composition and containing a wetting agent which comprises an alkali metal or ammonium salt of N-tallow-fi-iminodipropionic acid.
2. A coating composition according to claim 1 wherein said coating composition comprises a silver halide.
3. A coating composition according to claim 1 wherein said coating composition comprises a silver halide and said proteinaceous composition comprises gelatin.
4. A coating solution for coating at least one layer of a photographic element comprising a proteinaceous composition and containing a wetting agent which comprises disodium salt of N-tallow-fl-iminodipropionic acid.
5. A coating solution according to claim 4 wherein said disodium salt of N-tallow-fi-iminodipropionic acid is present in an amount ranging from approximately 0.2 to 2.7 parts per parts of said proteinaceous compositron.
6. A coating solution according to claim 4 which comprises a silver halide composition.
7. A coating solution according to claim 4 wherein said proteinaceous composition comprises gelatin.
8. A photographic element comprising a support, at least one light-sensitive silver halide layer and at least one layer comprising a proteinaceous composition and containing a wetting agent comprising an alkali metal or ammonium salt of N-tallow-fl-iminodipropionic acid.
9. A photographic element according to claim 8 wherein said proteinaceous composition is a gelatin.
References Cited UNITED STATES PATENTS 2,240,471 4/1941 Swan 1l7164 2,919,197 12/1959 Duin 260404 2,933,406 4/ 1960 Salzberg et al. 106125 2,958,605 11/1960 Leiner et a1. 106-125 2,992,109 7/1961 Allen 961 11 2,994,611 8/1961 Heyna et al. 96111 3,038,804 6/1962 Knox et al. 96111 3,133,816 5/1964 Ben-Ezra 9694 J. TMVIS BROWN, Primary Examiner US. Cl. X.R.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22510862A | 1962-09-20 | 1962-09-20 | |
| US437273A US3306749A (en) | 1962-09-20 | 1965-03-04 | Gelatin coating compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3506449A true US3506449A (en) | 1970-04-14 |
Family
ID=26919304
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US225108A Expired - Lifetime US3506449A (en) | 1962-09-20 | 1962-09-20 | Gelatin coating compositions with n-tallow-beta-iminodipropionic acid |
| US437273A Expired - Lifetime US3306749A (en) | 1962-09-20 | 1965-03-04 | Gelatin coating compositions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US437273A Expired - Lifetime US3306749A (en) | 1962-09-20 | 1965-03-04 | Gelatin coating compositions |
Country Status (1)
| Country | Link |
|---|---|
| US (2) | US3506449A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3408193A (en) * | 1964-12-16 | 1968-10-29 | Eastman Kodak Co | Coating compositions for the coating out of anionic mordant-acid dye layers |
| US3475174A (en) * | 1965-03-29 | 1969-10-28 | Konishiroku Photo Ind | N,n dialkyl n' acyl-diaminocarboxylic acid coating compositions |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2240471A (en) * | 1940-03-07 | 1941-04-29 | Eastman Kodak Co | Photographic gelatin layer containing a n-acylated amino acid |
| US2919197A (en) * | 1954-02-26 | 1959-12-29 | Lever Brothers Ltd | Method of preparing oil-in-water emulsions |
| US2933406A (en) * | 1957-09-11 | 1960-04-19 | Borden Co | Protein and nonionic agent compositions |
| US2958605A (en) * | 1958-07-22 | 1960-11-01 | Union Carbide Corp | Adhesive compositions |
| US2992109A (en) * | 1960-06-17 | 1961-07-11 | Eastman Kodak Co | Hardening of photographic emulsions |
| US2994611A (en) * | 1958-03-19 | 1961-08-01 | Hoechst Ag | Hardening of protein |
| US3038804A (en) * | 1956-07-30 | 1962-06-12 | Eastman Kodak Co | Coating aids for gelatin compositions |
| US3133816A (en) * | 1960-07-15 | 1964-05-19 | Gen Aniline & Film Corp | Photographic coating formulation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3042522A (en) * | 1958-06-13 | 1962-07-03 | Gen Aniline & Film Corp | Photographic film and a composition for improving the slippage characteristics thereof |
-
1962
- 1962-09-20 US US225108A patent/US3506449A/en not_active Expired - Lifetime
-
1965
- 1965-03-04 US US437273A patent/US3306749A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2240471A (en) * | 1940-03-07 | 1941-04-29 | Eastman Kodak Co | Photographic gelatin layer containing a n-acylated amino acid |
| US2919197A (en) * | 1954-02-26 | 1959-12-29 | Lever Brothers Ltd | Method of preparing oil-in-water emulsions |
| US3038804A (en) * | 1956-07-30 | 1962-06-12 | Eastman Kodak Co | Coating aids for gelatin compositions |
| US2933406A (en) * | 1957-09-11 | 1960-04-19 | Borden Co | Protein and nonionic agent compositions |
| US2994611A (en) * | 1958-03-19 | 1961-08-01 | Hoechst Ag | Hardening of protein |
| US2958605A (en) * | 1958-07-22 | 1960-11-01 | Union Carbide Corp | Adhesive compositions |
| US2992109A (en) * | 1960-06-17 | 1961-07-11 | Eastman Kodak Co | Hardening of photographic emulsions |
| US3133816A (en) * | 1960-07-15 | 1964-05-19 | Gen Aniline & Film Corp | Photographic coating formulation |
Also Published As
| Publication number | Publication date |
|---|---|
| US3306749A (en) | 1967-02-28 |
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