US3291624A - Acetylated derivatives of dialdehydes and of their hemiacetals as gelatin hardeners - Google Patents

Acetylated derivatives of dialdehydes and of their hemiacetals as gelatin hardeners Download PDF

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Publication number
US3291624A
US3291624A US303664A US30366463A US3291624A US 3291624 A US3291624 A US 3291624A US 303664 A US303664 A US 303664A US 30366463 A US30366463 A US 30366463A US 3291624 A US3291624 A US 3291624A
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US
United States
Prior art keywords
control
gelatin
hardeners
hemiacetals
dialdehydes
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
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US303664A
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English (en)
Inventor
Jeffreys Roy Arthur
Donald M Burness
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Eastman Kodak Co
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Eastman Kodak Co
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Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US303664A priority Critical patent/US3291624A/en
Priority to GB44755/66A priority patent/GB1152058A/en
Priority to FR79081A priority patent/FR1496008A/fr
Priority to DE19661547752 priority patent/DE1547752A1/de
Application granted granted Critical
Publication of US3291624A publication Critical patent/US3291624A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
    • G03C1/301—Aldehydes or derivatives thereof, e.g. bisulfite addition products

Definitions

  • This invention relates to gelatin compositions containing therein as a hardener a diacyloxy compound of a certain type.
  • gelatin hardeners Some of these compounds have exhibited properties of one kind or another which limited their use in certain situations. For instance, formaldehyde has shown desensi-tizing characteristics in contact with certain highly sensitized photographic emulsions. eners have been so efiective that thickening of gelatin coating compositions occurs very shortly after the hardener addition, hence, the urgency of almost immediate coating. Some hardeners have had toxic effects and have been avoided where possible in manufacturing operations. Other hardeners have shown tendencies to fog and stain photographic elements with passage of time.
  • One object of our invention is to provide compositions which will give hardened gelatin layers but which do not exhibit thickening upon incorporating the hardener in the coating composition.
  • Another object of our invention is to provide hardeners for gelatin-silver halide photographic emulsion which do not adversely aifect their sensitivity and do not fog or stain the emulsions.
  • a further object of our invention is to provide gelatin coating compositions which provide layers which retain a high degree of flexibility upon storage or aging. Other objects of our invention will appear herein.
  • the hardeners in accordance with our invention are represented by the following type formulas in which acetyl is used as the acyl group. If desired, other acyl groups may be employed but the acetoxy compounds are preferred having been found to be quite convenient for use as hardeners:
  • gelatin compositions such as photographic gelatinsilver halide photographic emulsions containing a hardener in accordance with the invention may be coated out onto a support such as paper, film base or the like, to form photographic elements.
  • Example 1 Mixed 1,1,2,2-diacetoxydiethoxyethane isomers were prepared by refluxing a mixture of 1,1,2,2-tetraethoxyethane and acetic anhydride plus a drop of methylsulphate as the catalyst. See the article by Fiesselmann and Horndler, Chem. Ber., 87, 911, (1954).
  • Example 2 Twenty-two ml. of 1,1,3,3-tetraethoxypropane was mixed with 20' ml. of acetic anhydride and one drop of methylsulphate was added thereto. The mixture was refluxed overnight. The product was then distilled yielding mixed 1,1,3,3-diacetoxydiethoxypropane isomers.
  • Example 3 Thirty grams of 1,1,2,2-tetramethoxyethane was reacted with 42 ml. of acetic anhydride with one drop of methyl sulphate by the method described in the preceding example.
  • the product obtained after distillation of the reaction mixture was fractionally crystallized from petroleum distillate (B.P., 60-80 to give the isomers of 1,1,2,2-diacetoxydi methoxyethane, M.P. 77 and 51, described by Fiesselmann and Horndler, Chem. Ber., 87, 908, 911 (1954).
  • Example 4 2,5-diacetoxy-2,S-dihydrofuran was prepared by the method described by Clauson-Kaas, U.S. Patent No. 2,514,026.
  • Example5 2,3-diacetoxy-1,4-dioxane was prepared by the method of Boeseken, Tellegen and Henriquez, J. Amer. Chem. Soc, 55, 1284, (1933).

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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)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US303664A 1963-08-21 1963-08-21 Acetylated derivatives of dialdehydes and of their hemiacetals as gelatin hardeners Expired - Lifetime US3291624A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US303664A US3291624A (en) 1963-08-21 1963-08-21 Acetylated derivatives of dialdehydes and of their hemiacetals as gelatin hardeners
GB44755/66A GB1152058A (en) 1963-08-21 1966-10-06 Gelatin Compositions
FR79081A FR1496008A (fr) 1963-08-21 1966-10-07 Nouvelles compositions à base de gélatine, contenant des agents tannants
DE19661547752 DE1547752A1 (de) 1963-08-21 1966-11-22 Verwendung von Diacyloxyverbindungen als Haertungsmittel zum Haerten der Gelatine photographischer Materialien

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US303664A US3291624A (en) 1963-08-21 1963-08-21 Acetylated derivatives of dialdehydes and of their hemiacetals as gelatin hardeners
GB44755/66A GB1152058A (en) 1963-08-21 1966-10-06 Gelatin Compositions
FR79081A FR1496008A (fr) 1963-08-21 1966-10-07 Nouvelles compositions à base de gélatine, contenant des agents tannants
DEE0032892 1966-11-22

Publications (1)

Publication Number Publication Date
US3291624A true US3291624A (en) 1966-12-13

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US303664A Expired - Lifetime US3291624A (en) 1963-08-21 1963-08-21 Acetylated derivatives of dialdehydes and of their hemiacetals as gelatin hardeners

Country Status (4)

Country Link
US (1) US3291624A (de)
DE (1) DE1547752A1 (de)
FR (1) FR1496008A (de)
GB (1) GB1152058A (de)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3471290A (en) * 1965-10-01 1969-10-07 Xerox Corp Photochromic photoresist imaging
US3480440A (en) * 1965-06-11 1969-11-25 Agfa Gevaert Ag Hardening of photographic gelatin-containing layers
US3981857A (en) * 1973-03-19 1976-09-21 Konishiroku Photo Industry Co., Ltd. Gelatin hardening process
FR2566771A1 (fr) * 1984-06-29 1986-01-03 Hoechst France Derives du glyoxal et procede pour leur preparation
US4952332A (en) * 1988-09-06 1990-08-28 Basf Aktiengesellschaft Detergents that contain acyl derivatives of dihydroxydioxane as bleach activators
EP0782045A1 (de) 1995-12-27 1997-07-02 Agfa-Gevaert N.V. Farbphotographisches Silberhalogenidfilmelement mit einem thermoplastischen Träger, der mit einem Laser markiert werden kann
US5851424A (en) * 1995-07-28 1998-12-22 Rolic Ag Photo cross-linkable liquid crystalline 1,4-dioxane-2,3 diyl derivatives

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2585596A (en) * 1949-12-29 1952-02-12 Du Pont Photographic emulsions containing 2, 5-dimethoxytetrahydrofuran
US2870013A (en) * 1956-11-29 1959-01-20 Eastman Kodak Co Hardening of gelatin with 2,3 dihydroxy dioxane
US3241972A (en) * 1963-05-28 1966-03-22 Eastman Kodak Co Gelatin compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2585596A (en) * 1949-12-29 1952-02-12 Du Pont Photographic emulsions containing 2, 5-dimethoxytetrahydrofuran
US2870013A (en) * 1956-11-29 1959-01-20 Eastman Kodak Co Hardening of gelatin with 2,3 dihydroxy dioxane
US3241972A (en) * 1963-05-28 1966-03-22 Eastman Kodak Co Gelatin compositions

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3480440A (en) * 1965-06-11 1969-11-25 Agfa Gevaert Ag Hardening of photographic gelatin-containing layers
US3471290A (en) * 1965-10-01 1969-10-07 Xerox Corp Photochromic photoresist imaging
US3981857A (en) * 1973-03-19 1976-09-21 Konishiroku Photo Industry Co., Ltd. Gelatin hardening process
FR2566771A1 (fr) * 1984-06-29 1986-01-03 Hoechst France Derives du glyoxal et procede pour leur preparation
DE3518075A1 (de) * 1984-06-29 1986-01-09 Société Française HOECHST, Puteaux, Hauts-de-Seine Glyoxalderivate und verfahren zu ihrer herstellung
US4952332A (en) * 1988-09-06 1990-08-28 Basf Aktiengesellschaft Detergents that contain acyl derivatives of dihydroxydioxane as bleach activators
US5851424A (en) * 1995-07-28 1998-12-22 Rolic Ag Photo cross-linkable liquid crystalline 1,4-dioxane-2,3 diyl derivatives
EP0782045A1 (de) 1995-12-27 1997-07-02 Agfa-Gevaert N.V. Farbphotographisches Silberhalogenidfilmelement mit einem thermoplastischen Träger, der mit einem Laser markiert werden kann

Also Published As

Publication number Publication date
DE1547752A1 (de) 1969-11-20
FR1496008A (fr) 1967-09-22
GB1152058A (en) 1969-05-14

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