US3628961A - Gelatin compositions containing a triazine type hardener and an aliphatic mono- or dicarboxylic acid - Google Patents
Gelatin compositions containing a triazine type hardener and an aliphatic mono- or dicarboxylic acid Download PDFInfo
- Publication number
- US3628961A US3628961A US33076A US3628961DA US3628961A US 3628961 A US3628961 A US 3628961A US 33076 A US33076 A US 33076A US 3628961D A US3628961D A US 3628961DA US 3628961 A US3628961 A US 3628961A
- Authority
- US
- United States
- Prior art keywords
- gelatin
- layers
- percent
- emulsion
- 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 abstract description 27
- 229920000159 gelatin Polymers 0.000 title abstract description 27
- 239000008273 gelatin Substances 0.000 title abstract description 27
- 235000019322 gelatine Nutrition 0.000 title abstract description 27
- 235000011852 gelatine desserts Nutrition 0.000 title abstract description 27
- -1 aliphatic mono- Chemical class 0.000 title abstract description 6
- 239000004848 polyfunctional curative Substances 0.000 title description 22
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title description 3
- 239000000203 mixture Substances 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract description 6
- 239000000839 emulsion Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 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 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
- PVJKFTUUDTYJJG-UHFFFAOYSA-N 1-[2,3-di(prop-2-enoyl)triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CCCN(C(=O)C=C)N1C(=O)C=C PVJKFTUUDTYJJG-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- BCFOOGYLNUHSHL-UHFFFAOYSA-N 1-(triazin-4-yl)prop-2-en-1-one Chemical compound C=CC(=O)C1=CC=NN=N1 BCFOOGYLNUHSHL-UHFFFAOYSA-N 0.000 description 1
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical class O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VAYROLOSUUAGTR-UHFFFAOYSA-N [Ag].[I] Chemical compound [Ag].[I] VAYROLOSUUAGTR-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000704 physical effect Effects 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
- 150000004053 quinones Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 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
-
- 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
- G03C1/305—Hardeners containing a diazine or triazine ring
Definitions
- the invention relates to a process for hardening gelatin layers, particularly photographic layers, with N,N', N"- trisacryloylor N,N', N"-trisvinyl-sulfonyl-l,3,5-hexahydrotriazine in the presence of aliphatic carboxylic acids as hardening accelerators.
- metal salts such as chromium, aluminum or zirconium salts, aldehydes or their derivatives, particularly formaldehyde, dialdehyries, mucochloric acid, diketones, quinones and chlorides of dibasic organic acids and dianhydrides are already known.
- Compounds which contain at least two heterocyclic, threemembered rings which can easily be split, such as ethylene oxide or ethylene imine may be used as hardeners for gelatin.
- polyfunctional methanesulfonic acid esters and bis-a-chloroacyl-amido compounds have been described for this purpose.
- Alkali metal salts such as sodium salts of aliphatic carboxylic acids containing up to three carbon atoms, for example acetic acid, formic acid or propionic acid are particularly advantageous.
- the effect of the hexahydrotriazine hardener is greatly enhanced by the addition of the aliphatic carboxylic acids or their salts.
- the hardening time is considerably reduced or for a given hardening time the use of a much smaller concentration of hardener is sufficient.
- the hardener is added to the layers, or to the casting solutions for the layers, in quantities of 0.1 to 3 or 0.3 to 1.5 percent by weight, based on the dry weight of gelatin.
- EXAMPLE 1 A silver bromide gelatin emulsion which contains per kilogram of emulsion 8 g. of silver bromide, g. of gelatin, 24 g. of the color coupler of the following formula: 1
- Part 1 is used without further additive as a control sample
- Part 2 3 percent by weight of sodium acetate, based on the dry weight of gelatin are added to the emulsion;
- Part 3 3 percent by weight of sodium propionate based on the dry weight of gelatin are added.
- the above casting solutions are adjusted to a pH of 6.2 and cast on layer supports of cellulose triacetate.
- the dry layers have a layer thickness of 10 m.
- the melting point of the layers is determined as follows: The supported layer is half dipped in water which is continuously heated to C. The temperature at which the layer runs off the support (formation of streaks) is taken as the melting point or melting or melting-off point.
- the melting-off points of layers hardened according to the invention were determined in other tests after 5 minutes treatment with a 5 percent soda solution immediately after drying or after the storage indicated above. The water used for measuring the melting points was adjusted to pH 3.2 by the addition of sulfuric acid.
- Part 1 0.1 percent of N,N', N"-trisacryloyl-hexahydrotriazine based the dry weight of gelatin is added.
- Part 2 0.25 percent by weight of the same hardener is added.
- Part 3 0.4 percent by weight of the same hardener is added.
- the emulsion samples described above are again subdivided. One part is left without further additives and serves as control sample. In the other part, 3 parts by weight of sodium acetate, based on the dry weight of gelatin, are added. The emulsion samples are adjusted to pH 6.2 and the casting solutions are cast on a cellulose acetate support. The dry layers have a thickness of 10 pm.
- the melting points of the layers are determined as described in example i.
- the results are shown in the following table 2.
- the storage conditions indicated in the table are the: same as those indicated in example 1.
- EXAMPLE 3 A silver bromide gelatin emulsion which contains 20 g. of silver bromide and 45 g. of gelatin per layer is divided into two parts.
- Part 1 3.5 ml. ofa 5 percent aqueous solution 0fN,N', N"- trisacryloyl- 1,3,5-hexahydrotriazine (pH 6.5, corresponding to an addition 0f0.75 percent by weight based on the gelatin) are added.
- Part 2 The same quantity of hardener as in part 1 is added and in addition 20 ml. of a 1N succinic acid solution and ml. of a 2N NaOlHl solution.
- the two casting solutions are applied onto a support of cel' lulose triacetate and dried.
- the melting point of the layers is determined as described above and the scratch resistance of the emulsions is deter mined after storage at 35 C. and 80 percent relative humidity. Details are shown in table 4 below.
- the accelerating effect is preserved even when color couplers are added to the layer in the usual concentrations.
- the emulsions are applied to a layer support of cellulose triacetate (quantity of emulsion: 112.5 g./m.').
- the abrasion resistance of the emulsion layers is determined by the process described in example 3.
- the emulsions are applied to a cellulose acetate support according to example 4.
- the abrasion resistance is tested after storage at a relative humidity of 80 percent at 35 C.
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)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691924533 DE1924533A1 (de) | 1969-05-14 | 1969-05-14 | Haertung von Gelatineschichten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3628961A true US3628961A (en) | 1971-12-21 |
Family
ID=5734142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US33076A Expired - Lifetime US3628961A (en) | 1969-05-14 | 1970-04-29 | Gelatin compositions containing a triazine type hardener and an aliphatic mono- or dicarboxylic acid |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3628961A (enrdf_load_stackoverflow) |
| BE (1) | BE750314A (enrdf_load_stackoverflow) |
| DE (1) | DE1924533A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2047798A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1266655A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2759100A1 (de) * | 1977-12-30 | 1979-07-05 | Agfa Gevaert Ag | Verfahren zur haertung farbphotographischer silberhalogenidemulsionsschichten |
| DE3704905A1 (de) * | 1987-02-17 | 1988-08-25 | Moeller Friedrich Wilhelm | Raumteiler |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3497358A (en) * | 1965-05-03 | 1970-02-24 | Eastman Kodak Co | Gelatin compositions containing an aldehyde type hardener and an aliphatic monocarboxylic acid |
-
1969
- 1969-05-14 DE DE19691924533 patent/DE1924533A1/de active Pending
-
1970
- 1970-04-29 US US33076A patent/US3628961A/en not_active Expired - Lifetime
- 1970-05-08 GB GB1266655D patent/GB1266655A/en not_active Expired
- 1970-05-13 BE BE750314D patent/BE750314A/nl unknown
- 1970-05-14 FR FR7017695A patent/FR2047798A5/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3497358A (en) * | 1965-05-03 | 1970-02-24 | Eastman Kodak Co | Gelatin compositions containing an aldehyde type hardener and an aliphatic monocarboxylic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2047798A5 (enrdf_load_stackoverflow) | 1971-03-12 |
| GB1266655A (enrdf_load_stackoverflow) | 1972-03-15 |
| BE750314A (nl) | 1970-11-13 |
| DE1924533A1 (de) | 1970-11-26 |
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