US3497358A - Gelatin compositions containing an aldehyde type hardener and an aliphatic monocarboxylic acid - Google Patents
Gelatin compositions containing an aldehyde type hardener and an aliphatic monocarboxylic acid Download PDFInfo
- Publication number
- US3497358A US3497358A US452880A US3497358DA US3497358A US 3497358 A US3497358 A US 3497358A US 452880 A US452880 A US 452880A US 3497358D A US3497358D A US 3497358DA US 3497358 A US3497358 A US 3497358A
- Authority
- US
- United States
- Prior art keywords
- gelatin
- acid
- formaldehyde
- hardening
- hardener
- 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 58
- 229920000159 gelatin Polymers 0.000 title description 58
- 235000019322 gelatine Nutrition 0.000 title description 58
- 235000011852 gelatine desserts Nutrition 0.000 title description 58
- 239000008273 gelatin Substances 0.000 title description 57
- 239000004848 polyfunctional curative Substances 0.000 title description 22
- -1 aliphatic monocarboxylic acid Chemical class 0.000 title description 20
- 239000000203 mixture Substances 0.000 title description 10
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 46
- 150000003839 salts Chemical class 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 9
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 8
- 235000015110 jellies Nutrition 0.000 description 7
- 239000008274 jelly Substances 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 239000004332 silver Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
- FCTDKZOUZXYHNA-UHFFFAOYSA-N 1,4-dioxane-2,2-diol Chemical compound OC1(O)COCCO1 FCTDKZOUZXYHNA-UHFFFAOYSA-N 0.000 description 4
- 229910021607 Silver chloride Inorganic materials 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical class 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 4
- LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920002085 Dialdehyde starch Polymers 0.000 description 3
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Chemical class 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001361 adipic acid Chemical class 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229910001864 baryta Inorganic materials 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 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
- the sodium salts of acetic acid, formic acid, oxalic acid, benzoic acid, carbonic acid, phthalic acid and adipic acid are illustrative of the water soluble salts of an unsubstituted carbon acid.
- This invention relates to the hardening of photographic gelatin layers by the combination of an aldehyde-type hardener and a water soluble salt of a carbon acid.
- One object of our invention is to make possible an increase in the amount of hardening obtained with a given amount of formaldehyde in a gelatin photographic layer. Another object of our invention is to provide a means of increasing the hardening from formaldehyde when used in gelatin layers without being accompanied by stain. A further object of our invention is to provide a means of increasing the degree of hardening imparted by an aldehyde hardener in a gelatin composition without developing undesirable photographic effects such as tone changes and increased fog levels.
- a still further object of our invention is to provide gelatin coating compositions having therein aldehyde hardener and a water soluble salt of a carbon acid which exerts a synergistic effect upon the hardening characteristics of the aldehyde hardener.
- acetic acid formic acid, oXalic acid, benzoic acid, propionic acid, butyric acid, carbonic acid, caprylic acid, malonic acid, phthalic acid, adipic acid, etc.
- our invention is useful in hardening various types of gelatin and is particularly effective on pigskin gelatin, however, other types of gelatin such as bone belatin, hide gelatin and the like are also included.
- the gelatin has a jelly strength of not less than 50 grams bloom and it is gelatins of good jelly strength which are particularly useful in the compositions in accordance with the invention.
- the compositions in accordance with the invention there should be incorporated at least 1% of the salts based on the weight of the gelatin, the preferable proportion of salts being within the range of 5-15% based on the weight of the gelatin.
- the gelatin coating compositions employed for applying photographic gelatin layers in accordance with the invention are aqueous in nature but can tolerate up to as much as 10% of water soluble solvents such as alcohol, acetone or the like.
- EXAMPLE 1 A sample of pigskin gelatin of good jelly strength was dissolved in water to produce a solution of which the gelatin is 10% by weight. 0.5% of formaldehyde based on the dry weight of the gelatin was added to the solution. The solution was then separated into five equal parts and the following variations were made:
- the brush-off point of each sample was determined.
- the brush-off point is a melting point determination carried out under mildly abrasive conditions. The higher the temperature of brush-off, the harder and stronger the layer is.
- the brush-off point method of testing gelatin layers involves submerging the sample coated with the gelatin layer in water and raising the temperature at the rate of 5 F. per minute from room temperature to 212 F. In the test each sample is brushed after every 3 degree rise in temperature with a mechanical brushing device. The temperature selected as the end point is that at which the brush removes the gelatin coating from its support. The same measurement was repeated after 10 days aging at room conditions. The results obtained were as follows:
- EXAMPLE 2 To two types of photographic silver halide gelatin emulsions, various levels of formaldehyde and carboxylic acid salts were added. These emulsions were then coated onto a formaldehyde-free baryta coated paper support. The coatings were air dried overnight. The brush-off points were determined both fresh and after 10 days aging and these points were tabulated as follows:
- a composition of matter consisting essentially of high jelly strength gelatin, a hardening amount of a gelatin hardener selected from the group consisting of formaldehyde, mucochloric acid, dialdehyde starch, dihydroxydioxane, glutaraldehyde and dialdehyde plant gums and a Water soluble salt of an aliphatic monocarboxylic acid having 1 to carbon atoms.
- a gelatin hardener selected from the group consisting of formaldehyde, mucochloric acid, dialdehyde starch, dihydroxydioxane, glutaraldehyde and dialdehyde plant gums and a Water soluble salt of an aliphatic monocarboxylic acid having 1 to carbon atoms.
- composition of matter consisting essentially of high jelly strength gelatin, a hardening amount of formaldehyde and a Water soluble salt of an aliphatic monocarbxoylic acid having 1 to 10 carbon atoms.
- composition of matter consisting essentially of high jelly strength gelatin, a hardening amount of formaldehyde and an alkali metal salt of an aliphatic monocar' boxylic acid having 1 to 10 carbon atoms.
- composition of matter consisting essentially of high jelly strength gelatin, a hardening amount of formaldehyde and sodium acetate.
- a gelatin hardener selected from the group consisting of formaldehyde, mucochloric acid, dialdehyde plant gums and a water soluble salt of an aliphatic monocarboxylic acid having 1 to 10 carbon atoms.
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)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45288065A | 1965-05-03 | 1965-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3497358A true US3497358A (en) | 1970-02-24 |
Family
ID=23798324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US452880A Expired - Lifetime US3497358A (en) | 1965-05-03 | 1965-05-03 | Gelatin compositions containing an aldehyde type hardener and an aliphatic monocarboxylic acid |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3497358A (enrdf_load_stackoverflow) |
| BE (1) | BE680469A (enrdf_load_stackoverflow) |
| DE (1) | DE1547683A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1137547A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3628961A (en) * | 1969-05-14 | 1971-12-21 | Agfa Gevaert Ag | Gelatin compositions containing a triazine type hardener and an aliphatic mono- or dicarboxylic acid |
| US3630741A (en) * | 1968-12-31 | 1971-12-28 | Eastman Kodak Co | Adhesive gelatin-terpolymer materials having at least one conjugated vinylene dicarbonyl compound added to the emulsion polymerization reaction mixture |
| JPS49115329A (enrdf_load_stackoverflow) * | 1973-03-06 | 1974-11-05 | ||
| US4500453A (en) * | 1984-06-29 | 1985-02-19 | Dynagel Incorporated | Cross-linked protein composition using aluminum salts of acetic acid |
| US4714758A (en) * | 1985-04-10 | 1987-12-22 | Koken Co., Ltd. | Surfactant composed of acylated collagen or acylated gelatine and a production process thereof |
| US5187259A (en) * | 1990-11-14 | 1993-02-16 | Eastman Kodak Company | Chain extended gelatin |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2165421A (en) * | 1936-09-25 | 1939-07-11 | Eastman Kodak Co | Hardening photographic emulsions |
| US3140177A (en) * | 1960-11-10 | 1964-07-07 | Eastman Kodak Co | Processing color photographic materials |
-
1965
- 1965-05-03 US US452880A patent/US3497358A/en not_active Expired - Lifetime
-
1966
- 1966-04-29 GB GB18821/66A patent/GB1137547A/en not_active Expired
- 1966-05-02 DE DE19661547683 patent/DE1547683A1/de active Pending
- 1966-05-03 BE BE680469D patent/BE680469A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2165421A (en) * | 1936-09-25 | 1939-07-11 | Eastman Kodak Co | Hardening photographic emulsions |
| US3140177A (en) * | 1960-11-10 | 1964-07-07 | Eastman Kodak Co | Processing color photographic materials |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3630741A (en) * | 1968-12-31 | 1971-12-28 | Eastman Kodak Co | Adhesive gelatin-terpolymer materials having at least one conjugated vinylene dicarbonyl compound added to the emulsion polymerization reaction mixture |
| US3628961A (en) * | 1969-05-14 | 1971-12-21 | Agfa Gevaert Ag | Gelatin compositions containing a triazine type hardener and an aliphatic mono- or dicarboxylic acid |
| JPS49115329A (enrdf_load_stackoverflow) * | 1973-03-06 | 1974-11-05 | ||
| US4500453A (en) * | 1984-06-29 | 1985-02-19 | Dynagel Incorporated | Cross-linked protein composition using aluminum salts of acetic acid |
| US4714758A (en) * | 1985-04-10 | 1987-12-22 | Koken Co., Ltd. | Surfactant composed of acylated collagen or acylated gelatine and a production process thereof |
| US5187259A (en) * | 1990-11-14 | 1993-02-16 | Eastman Kodak Company | Chain extended gelatin |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1137547A (en) | 1968-12-27 |
| DE1547683A1 (de) | 1969-12-18 |
| BE680469A (enrdf_load_stackoverflow) | 1966-10-17 |
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