US2328166A - Manufacture of photographic bleaching layers - Google Patents

Manufacture of photographic bleaching layers Download PDF

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Publication number
US2328166A
US2328166A US307324A US30732439A US2328166A US 2328166 A US2328166 A US 2328166A US 307324 A US307324 A US 307324A US 30732439 A US30732439 A US 30732439A US 2328166 A US2328166 A US 2328166A
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Prior art keywords
grams
layers
manufacture
bleaching
photographic bleaching
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Expired - Lifetime
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US307324A
Inventor
Polgar Andre
Halmos Charles
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Polgar Andre
Halmos Charles
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Priority to FR846996T priority Critical
Application filed by Polgar Andre, Halmos Charles filed Critical Polgar Andre
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Publication of US2328166A publication Critical patent/US2328166A/en
Anticipated expiration legal-status Critical
Application status is Expired - Lifetime legal-status Critical

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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/02Direct bleach-out processes; Materials therefor; Preparing or processing such materials
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/28Silver dye bleach processes; Materials therefor; Preparing or processing such materials

Description

Patented Aug. 31, 1943 MANUFACTURE OF PHOTOGRAPHI BLEACHING LAYERS Andr Polgar and Charlcs Halmos, Paris, France;

vested in the Alien Property Custodian No Drawing. Application December 2, 1939, Serial No. 307,324. In France December 3, 1938 7 Claims.

The present invention has for object improvements in the manufacture of photographic bleaching layers, said improvements being adapted-to improve the quality of said layers and their preserving capacity.

It is known that bleaching layers, in particular those which are prepared with sensitisers the action of which is sufilciently high for them to be used practically, as for instance certain thiocarbamic derivatives, and more particularly sensitisers which are soluble in water, such as they are defined in the French patent in the name of the applicants filed on March 16, 1938, for: Process i or the preparation of photographic bleaching layers and suitable sensitisers, can only be kept for a short time before being exposed to light. At the end of a greater or less period of time, a coloured .residue is formed in the layer which is no longer sensitive to light and does not become discoloured when exposed. On the other hand, a reversibility or bleaching after exposure, is'noticed, particularly after wetting the prints with water or with other liquids (fixing liquids, etc.) or if the prints are allowed to stay in the air, or if they are exposed to heat. This recoloration takes place instantaneously when certain dyestuffs for instance oxazines, are used.

These disadvantages are produced by reactions independent of light, and which probably take place between the active derivatives (sensitisers), the dye-stuns and the support. Said reaction appear to be of a non photo-chemical nature, indicated for instance by .a relatively high coeiilcient of temperature. Now, it has been found, according to the present invention, that particularly stable bleaching layers are obtained, which are of very good keeping qualities, do not form coloured residues, are non reversible, in short, present only the required photo-chemical reactions, if, in the layers there are introduced,

or if said layers are treated with, organic compounds answering to the general formulae:

l Ru

i As compounds suitable for the present process, there can be cited, by way of non limiting examples, acyl-amides, carbamides, sulphocarb'amides (except the known sensitisers) amidines,

guanidines, hydrazides, hydrazidines, acylhydroxamines, imi'doethers, various heterocyclic compounds, the formulaof which corresponds to the general formulae indicated, etc., as well as their derivatives and their salts.

For the preparation of the aqueous layers,'acid amides are especially suitable, in particular those which, by hygroscopicity, retain the dampness necessary for the satisfactory operation of the layer. Very good results have been obtained with acetamide. The layers thus formed presented, even in presence of sulphuric acid, a stability exceeding six months, sometimes more and did not present recolorations. In certain cases, the simultaneous use of hygroscopic agents (such for instance as glycerol) is recommended.

By way of non limiting examples, various formulae for the preparation ofbleaching layers according to the invention will be given hereinafter.

Example 1.The solution for the bleaching layer; is prepared by dissolving 1 gram of basic dye-stuffs in 2 grams of hydrochloric acid and 100 grams of water containing 2% of gelatine.

15 grams of N-di- 3-oxethyl-N'allyl-sulpho-urea are added and finally 20 grams of acetamide.

Example 2.In 100 grams of water are dissolved 6 grams of gelatine, /2 gram of Nile blue sulphate, and 5 grams of N bis (-5, A, dioxypropyl)-N-allyl-sulpho-urea, 10 grams of sulphourea and 5 grams of glycerol are added.

Example 3.A bleaching solution similar to that of Example 1 is prepared, and 15 grams of monochloracetamide and 10 grams of glycerol are added. It is applied on paper and exposed to an arc lamp.

Example 4.In 200 grams of water are dissolved 10 grams of gelatine, 6 grams of Capri blue, 4 grams of sulphopyronine G sulphate, 8 grams of methoxyresorcin-benzeine chloride. 500 grams 01' a 20% alcoholic solution 01' diethylallyl-sulpho-urea, 100 grams of N-di-p-oxyethyl- Nallylsulpho-urea and 50 grams of N-B-oxyethyl-N'allyl-sulpho-urea and finally grams of oxamide are gradually added. 20 grams of this solution is spreadout on a square meter of baryta paper.

Example 5.Ordinary photographic support paper is acidified with diluted sulphuric acid and it is coated with 20 grams of the following solution: grams of water, 10 grams of gelatine and 10 grams of propionyl-hydrazide. Then a sitized paper for photographicbleaching.

Example 7.-30 grams oi cellulose acetate are dissolved in 200 grams of acetone. To this solution are added, 50 grams of methyl alcohol containing 0.08 gram of brilliant cresyl blue, 0.05

gram of sulphorhodamine and 0.10 gram of thio-- fiuoressceine, and then 10 grams of oxalic acid, 12 grains of diethylallyl-sulpho-urea and 10 grams of succinimide are added. Finally, the solution is run on a transparent film.

Example 8.--A bleaching solution is prepared with 5 grams of basic dye-stuffs and 300 grams of 2% sulphuric acid, 30 grams of thiosinamine and 50 grams of diethyanolallylsulpho-urea. Finally, 35 grams of imidazole chlorhydrate are added.

Example 9.-An aqueous solution of crystallized violet sensitised by thiosinamine is spread out on paper. A solution of diacetylimine is then applied.

We claim:

1. In a process for manufacturing photographic bleaching layers, the step consisting in introducing in the compositionoi these layers an organic compound the constitution of which can be set forth by one of the tautomer formulae:

in which X represents an element of the oxygen series selected from a group consisting of 0, Se, Te, and R1, R2, R3 each represents a saturated monovalent element, radical or group with the exception of compounds having a sensitizing power, by choosing the organic compounds in question among the compounds belonging to the following classes: acyl amides, acyl imides, amidines, guanidines, hydrazides, hydrazidines, hy-

, droxamic acids, imido-ethers and carbamides.

sition of these layers an amidine.

5. In a process for manufacturing photographic bleaching layers as defined in claim 1, the step consisting in introducing in the composition of these layers a guanidine.

6. In the process of manufacturing photographic bleaching layers, as defined in claim 1 in which the organic compound introduced is an acylamide.

7. In the process of manufacturing photographic bleaching layers, as defined in claim 1 in which the organic compound introduced is an acylimide.

an Potash.

US307324A 1938-12-03 1939-12-02 Manufacture of photographic bleaching layers Expired - Lifetime US2328166A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR846996T 1938-12-03

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US2328166A true US2328166A (en) 1943-08-31

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US307324A Expired - Lifetime US2328166A (en) 1938-12-03 1939-12-02 Manufacture of photographic bleaching layers

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US (1) US2328166A (en)
BE (1) BE437152A (en)
FR (1) FR846996A (en)
GB (1) GB586389A (en)

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US5616443A (en) * 1993-08-05 1997-04-01 Kimberly-Clark Corporation Substrate having a mutable colored composition thereon
US5643356A (en) * 1993-08-05 1997-07-01 Kimberly-Clark Corporation Ink for ink jet printers
US5645964A (en) * 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US5681380A (en) * 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5686503A (en) * 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and applications therefor
US5700850A (en) * 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US5721287A (en) * 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5733693A (en) * 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US5739175A (en) * 1995-06-05 1998-04-14 Kimberly-Clark Worldwide, Inc. Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer
US5747550A (en) * 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5773182A (en) * 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US5782963A (en) * 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5786132A (en) * 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US5798015A (en) * 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
US5811199A (en) * 1995-06-05 1998-09-22 Kimberly-Clark Worldwide, Inc. Adhesive compositions containing a photoreactor composition
US5837429A (en) * 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US5849411A (en) * 1995-06-05 1998-12-15 Kimberly-Clark Worldwide, Inc. Polymer film, nonwoven web and fibers containing a photoreactor composition
US5855655A (en) * 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5865471A (en) * 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5885337A (en) * 1995-11-28 1999-03-23 Nohr; Ronald Sinclair Colorant stabilizers
US5891229A (en) * 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6008268A (en) * 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US6017661A (en) * 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6017471A (en) * 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6033465A (en) * 1995-06-28 2000-03-07 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6071979A (en) * 1994-06-30 2000-06-06 Kimberly-Clark Worldwide, Inc. Photoreactor composition method of generating a reactive species and applications therefor
US6099628A (en) * 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US6228157B1 (en) 1998-07-20 2001-05-08 Ronald S. Nohr Ink jet ink compositions
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
US6265458B1 (en) 1998-09-28 2001-07-24 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6277897B1 (en) 1998-06-03 2001-08-21 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6294698B1 (en) 1999-04-16 2001-09-25 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same
US6368396B1 (en) 1999-01-19 2002-04-09 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6486227B2 (en) 2000-06-19 2002-11-26 Kimberly-Clark Worldwide, Inc. Zinc-complex photoinitiators and applications therefor
US6503559B1 (en) 1998-06-03 2003-01-07 Kimberly-Clark Worldwide, Inc. Neonanoplasts and microemulsion technology for inks and ink jet printing
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same

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US5643701A (en) * 1993-08-05 1997-07-01 Kimberly-Clark Corporation Electrophotgraphic process utilizing mutable colored composition
US5643356A (en) * 1993-08-05 1997-07-01 Kimberly-Clark Corporation Ink for ink jet printers
US5645964A (en) * 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US6060200A (en) * 1993-08-05 2000-05-09 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms and methods
US5683843A (en) * 1993-08-05 1997-11-04 Kimberly-Clark Corporation Solid colored composition mutable by ultraviolet radiation
US5908495A (en) * 1993-08-05 1999-06-01 Nohr; Ronald Sinclair Ink for ink jet printers
US5616443A (en) * 1993-08-05 1997-04-01 Kimberly-Clark Corporation Substrate having a mutable colored composition thereon
US5700850A (en) * 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US6017471A (en) * 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US5721287A (en) * 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5733693A (en) * 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US6054256A (en) * 1993-08-05 2000-04-25 Kimberly-Clark Worldwide, Inc. Method and apparatus for indicating ultraviolet light exposure
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US5773182A (en) * 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US6127073A (en) * 1993-08-05 2000-10-03 Kimberly-Clark Worldwide, Inc. Method for concealing information and document for securely communicating concealed information
US6120949A (en) * 1993-08-05 2000-09-19 Kimberly-Clark Worldwide, Inc. Photoerasable paint and method for using photoerasable paint
US5865471A (en) * 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5858586A (en) * 1993-08-05 1999-01-12 Kimberly-Clark Corporation Digital information recording media and method of using same
US6060223A (en) * 1993-08-05 2000-05-09 Kimberly-Clark Worldwide, Inc. Plastic article for colored printing and method for printing on a colored plastic article
US6342305B1 (en) 1993-09-10 2002-01-29 Kimberly-Clark Corporation Colorants and colorant modifiers
US5685754A (en) * 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and polymer coating applications therefor
US6071979A (en) * 1994-06-30 2000-06-06 Kimberly-Clark Worldwide, Inc. Photoreactor composition method of generating a reactive species and applications therefor
US6090236A (en) * 1994-06-30 2000-07-18 Kimberly-Clark Worldwide, Inc. Photocuring, articles made by photocuring, and compositions for use in photocuring
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
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US5686503A (en) * 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and applications therefor
US6008268A (en) * 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US6017661A (en) * 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6235095B1 (en) 1994-12-20 2001-05-22 Ronald Sinclair Nohr Ink for inkjet printers
US5747550A (en) * 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5681380A (en) * 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5849411A (en) * 1995-06-05 1998-12-15 Kimberly-Clark Worldwide, Inc. Polymer film, nonwoven web and fibers containing a photoreactor composition
US5837429A (en) * 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US6063551A (en) * 1995-06-05 2000-05-16 Kimberly-Clark Worldwide, Inc. Mutable dye composition and method of developing a color
US5786132A (en) * 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US5811199A (en) * 1995-06-05 1998-09-22 Kimberly-Clark Worldwide, Inc. Adhesive compositions containing a photoreactor composition
US5798015A (en) * 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
US5739175A (en) * 1995-06-05 1998-04-14 Kimberly-Clark Worldwide, Inc. Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer
US6033465A (en) * 1995-06-28 2000-03-07 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6168655B1 (en) 1995-11-28 2001-01-02 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5885337A (en) * 1995-11-28 1999-03-23 Nohr; Ronald Sinclair Colorant stabilizers
US6099628A (en) * 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5782963A (en) * 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
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US5855655A (en) * 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5891229A (en) * 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6277897B1 (en) 1998-06-03 2001-08-21 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6503559B1 (en) 1998-06-03 2003-01-07 Kimberly-Clark Worldwide, Inc. Neonanoplasts and microemulsion technology for inks and ink jet printing
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US6265458B1 (en) 1998-09-28 2001-07-24 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6368396B1 (en) 1999-01-19 2002-04-09 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
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Also Published As

Publication number Publication date
GB586389A (en) 1947-03-18
FR846996A (en) 1939-09-28
BE437152A (en)

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