US2416021A - Light sensitive diazotype compositions and process - Google Patents

Light sensitive diazotype compositions and process Download PDF

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US2416021A
US2416021A US570471A US57047144A US2416021A US 2416021 A US2416021 A US 2416021A US 570471 A US570471 A US 570471A US 57047144 A US57047144 A US 57047144A US 2416021 A US2416021 A US 2416021A
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naphthol
light sensitive
arylsulfonyl
ester
light
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US570471A
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Schoen Andre
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GAF Chemicals Corp
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General Aniline and Film Corp
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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
    • G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds

Definitions

  • the present invention relates to light sensitive photographic printing material, compositions and to the process of preparing prints therefrom.
  • Another object of the invention is the production of photographic coatin material of good stability in the dark and capable of being developed by metal salts or diazo compounds.
  • a .further object is the provision of photographic material capable of development by diazo compounds and which are of particular value in producing dark shades of high visual density.
  • Another object is the provision of photographic material and the process for preparing negative prints from a pattern, or image to be reproduced, infwhich the image is developable by metal salts or diazo compounds.
  • the present invention is based upon the discovery that the arylsulfonyl compounds of aminonaphthol, sulfonic acids, upon exposure to light acquire the ability to reduce metallic salts or to couple with diazo compounds.
  • I coat a suitable base, carrier or support with an arylsulfonyl compound of an aminonaphthol sulfonic acid, and expose the-coated carrier to light under a suitable patternydesign' or picture to be reproduced, whereby the compound in those areas exposed to light is decomposed.
  • the image in ,the light exposed areas then is subjected to a suitable treatment, for example, with metal salts or a suitable diazo compound, the latter treatment preferably being carried out in neutral orslightly alkaline solution, to develop a colored negative.
  • a suitable treatment for example, with metal salts or a suitable diazo compound, the latter treatment preferably being carried out in neutral orslightly alkaline solution, to develop a colored negative.
  • the colors developed generally range from red through blue to black, dependin on the particular aminonaphthol sulfonic acid employed and on the metal salt or diazo compound with which it is reacted.
  • the term negative as herein employed is used relatively to the pattern or print which it is desired to reproduce, regardless of whether that pattern or print is itself a positive or a negative.
  • arylsulfonyl compounds of those aminonaphthol sulfonic acids which in the free state'are capable of coupling with dia zo compounds.
  • the arylsulfonyl compounds of such aminonaphthol sulfonic acids wherein ArSOz represents the residue of an arylsulfonyl group and n is a whole number of greater than zero.
  • ArSOz represents the residue of an arylsulfonyl group and n is a whole number of greater than zero.
  • This formula is not intended as limiting or defining the orientation in the naphthalene nucleus of the various substituents.
  • the action of light is believed to cause hydrolysis of the ester, and in some cases also hydrolysis of the amide, resulting in the restoration of the coupling capacity of the aminonaphthol sulfonic acid.
  • the image may be developed by treatment with a reducible metal salt to develop the color, with or without a subsequent fixing treatment.
  • the image is developed by treatment with a diazo compound.
  • it is desired to develop the image by treatment with a diazo compound it will, of course, be understood that only those aminonaphthol sulfonic acids which in the free state are capable of coupling with diazo compounds are suitable.
  • aminonaphthol sulfonic acids which in the form of the arylsulfonyl compounds are suitable for practicing the present invention are the metathetical Lil-aminonaphthol sulfonic acids, and 2,l-aminonaphthol sulfonic acids, such as 1-amino-Z-naphthol-l-sulfonic acid, the 1?
  • amino-S-naphthol sulfonic acids such as 1- amino-8-naphthol-3,6-disulfonic acid, l-amino- 8-naphthol-2,4-disulfonic acid, l-amino-B-naphthol5,7-disulfonic acid, l-amino-S-naphthol-dsulfonic acid, the 2-amino-8-naphthol sulfonic acids, such as Z-amino-8-naphtho1-6-su1fonic acid and 1-amino-5-naphthol-2,'7-disulfonic acid, I prefer to employ in the practice of my invention aminonaphthol sulfonic acids wherein the hydroxyl group is in an alpha position and the amino group is in a difierent nucleus and which have a free position para to the hydroxyl gr'dup'g In some of
  • arylsulfonyl compounds of aminonaphthol sulfonic acids employed in the present invention may be prepared in known manner, for example,.
  • arylsulfonyl chloride by acting in the dark on an aminonaphtholwith an arylsulfonyl chloride to acidylategthe amino group and esterify the hydroxy group.
  • benzenesulfonyl ester of l-benze ne s ule fonamido-8-naphthol-4-sulfonic acid, or the 2- chloro-p-toluenesulfonyl ester of 1-(2-chloro-ptoluenesulfonamido)-8i1aphthol -3,6- disulfonic acid and the like.
  • the coating may :include :a light stable diazo .compound,.as .for example Levamine .Qran-ge .GSA. [-2(3 chlorobenzenediazoamino) p -.sulobenzoic acid] and after exposure .to light for example, in theform of the zinc chloride double salt, t in chloride double salt, cadmium chloride double salt, boron tetrafluoride .double salt, the chloride, sulfate, orthe like.
  • those diazo compounds which contain one or more etherified phenolic groups are preierred.
  • diazo compounds that may .be employed are the diazo compounds of diethyl- .aminoaniline, o-dianisidine, o-phenetidin, 4- chloro-2-anisidine, 4-benzoylamino2.5-diethoxyaniline, 4-benzoylamino-2,5-dimethoxyaniline, or
  • mercury salts and salts of the metals above mercury in the electromotive series, as for example silvernitrate or amm'omacal silver nitrate.
  • mercuric salts I use an after-treatment .with ammonia to develop a black color in the reduced mercurous image.
  • Fema 1 salt of o-ethoxybenzenediazonium chloride which "results in the development of a, reddish purple positive. The print is then washed and dried.
  • Emample 2 .14 5 M1 s prepared t in naabeut 5 rams of 2'-chloro-p-toluenesulfonyl ester of 1-(2' chloro p toluenesulfonamido) -8-naphthol-3,6 disulfonic acid in 50 cc. water containing about -.,-0.:5,c.c. .concentrated aqueous ammonia. This so- .lution .is applied on a suitable gelatin coated paper, dried andthe coated paper is exposed to 1' 'htund r tive.
  • the color is developed l oy treat nent t1; 1% solution of the diazonium chloride of 4-bengoyl amino-2,5-diethoxyaniline containing about 1% sodium acetate. There is thus produced a blue positive image.
  • This solution is applied son a .suitable .gelatin .coated paper, .dried, and the coated .paper is exposed to light under "a negatiue.
  • the image may :be developed'lby dip- .ping the paper into .a bath containing about 5 rams silver nitrate tin-1100 no.
  • arylsulfona midonaphthol sulfom'c acid until decomposition thereof occurs, and developingthe "latent image :by reaction with a memberof the group consistring of salts .of @metals above mercury-in the electromotiwe series and diazo compounds.
  • the process which comprises exposing to light under a pattern to-be reproduceda base carrying an arylsul-fonylester of a l-ar-ylsulfonamidoefi-naphthol disulfonic acid until decomposition thereof occurs, and coupling the decomposed product. thereof with a diazo mm.
  • DQ JML The r ce ss mmnrises .elgnesip to ist? under a nature .te ented car yin an arr se fieeyl este mido-2-naphthol sulfonic ac image with a salt of a metal above mercury in the electromotive series.
  • the process which comprises exposing to light under a pattern to be reproduced, a base carrying an arylsulfonyl ester of l-arylsulfonamido-2-naphthol-4-sulfonic acid until decomposition thereof occurs, and developing the latent image by couplin the decomposed product thereof with a diazo compound.
  • Light sensitive material which comprises a base carrying a light sensitive arylsulfonyl ester of an arylsulfonamidonaphthol sulfonic acid,
  • Light ensitive material which com-prises a base carrying a light sensitive arylsulfonyl ester of an arylsulfonamido naphthol disulfonic acid.
  • Light sensitive material which comprises a base carrying a light sensitive arylsulfonyl ester of 1-arylsulfonamido-2-naphthol disulfonic acid.
  • Light sensitive material which comprises a base carrying a light sensitive arylsulfonyl ester of a 1-arylsulfonamido-8-naphtho1-4-sulfonic acid.
  • a light sensitive material comprising a base carrying an arylsulfonyl ester of l-arylsulfonamido-8-naphthol-3,6-clisulfonic acid.
  • a light sensitive material comprising a base carrying an alpha arylsulfonyl ester of an arylsulfonamido-alpha naphthol sulfonic acid having a free position para to the hydroxyl group and wherein the hydroxy and amino groups are in different nuclei.
  • a light sensitive material comprising a base carrying a light sensitive arylsulfonyl ester of an arylsulfonamido-alpha-naphthol sulfonic acid having a free position para to the hydroxyl group.

Description

Bast AVAILABLE! ourt Patented Feb. 18, 1947 LIGHT SENSITIVE DIAZOTYPE COM- POSITIONS AND PROCESS Andr Schoen, Easton, Pa., assignor to General Aniline & Film Corporation, New York, N. Y.,
a corporation of Delaware No Drawing. Application December 29, 1944, Serial No. 570,471
17 Claims.
The present invention relates to light sensitive photographic printing material, compositions and to the process of preparing prints therefrom.
It is an object of the invention to prepare photographic printing materials in which the color may be developed by a suitable after-treatment.
Another object of the invention is the production of photographic coatin material of good stability in the dark and capable of being developed by metal salts or diazo compounds.
A .further object is the provision of photographic material capable of development by diazo compounds and which are of particular value in producing dark shades of high visual density.
Another object is the provision of photographic material and the process for preparing negative prints from a pattern, or image to be reproduced, infwhich the image is developable by metal salts or diazo compounds.
The present invention is based upon the discovery that the arylsulfonyl compounds of aminonaphthol, sulfonic acids, upon exposure to light acquire the ability to reduce metallic salts or to couple with diazo compounds. In utilizing this discovery in the practice of my invention, I coat a suitable base, carrier or support with an arylsulfonyl compound of an aminonaphthol sulfonic acid, and expose the-coated carrier to light under a suitable patternydesign' or picture to be reproduced, whereby the compound in those areas exposed to light is decomposed. The image in ,the light exposed areas then is subjected to a suitable treatment, for example, with metal salts or a suitable diazo compound, the latter treatment preferably being carried out in neutral orslightly alkaline solution, to develop a colored negative. The colors developed generally range from red through blue to black, dependin on the particular aminonaphthol sulfonic acid employed and on the metal salt or diazo compound with which it is reacted. The term negative as herein employed is used relatively to the pattern or print which it is desired to reproduce, regardless of whether that pattern or print is itself a positive or a negative.
Where it is desired to employ diazo compound to develop the color, I employ the arylsulfonyl compounds of those aminonaphthol sulfonic acids which in the free state'are capable of coupling with dia zo compounds. The arylsulfonyl compounds of such aminonaphthol sulfonic acids wherein ArSOz represents the residue of an arylsulfonyl group and n is a whole number of greater than zero. This formula is not intended as limiting or defining the orientation in the naphthalene nucleus of the various substituents. The action of light is believed to cause hydrolysis of the ester, and in some cases also hydrolysis of the amide, resulting in the restoration of the coupling capacity of the aminonaphthol sulfonic acid.
In those cases where the action of light serves to hydrolyze both the ester group and the amide group, the image may be developed by treatment with a reducible metal salt to develop the color, with or without a subsequent fixing treatment. In those cases where the action of light hydrolyzes the ester and not the amide, the image is developed by treatment with a diazo compound. Where it is desired to develop the image by treatment with a diazo compound, it will, of course, be understood that only those aminonaphthol sulfonic acids which in the free state are capable of coupling with diazo compounds are suitable.
Examples of the aminonaphthol sulfonic acids which in the form of the arylsulfonyl compounds are suitable for practicing the present invention are the metathetical Lil-aminonaphthol sulfonic acids, and 2,l-aminonaphthol sulfonic acids, such as 1-amino-Z-naphthol-l-sulfonic acid, the 1? amino-S-naphthol sulfonic acids, such as 1- amino-8-naphthol-3,6-disulfonic acid, l-amino- 8-naphthol-2,4-disulfonic acid, l-amino-B-naphthol5,7-disulfonic acid, l-amino-S-naphthol-dsulfonic acid, the 2-amino-8-naphthol sulfonic acids, such as Z-amino-8-naphtho1-6-su1fonic acid and 1-amino-5-naphthol-2,'7-disulfonic acid, I prefer to employ in the practice of my invention aminonaphthol sulfonic acids wherein the hydroxyl group is in an alpha position and the amino group is in a difierent nucleus and which have a free position para to the hydroxyl gr'dup'g In some of such compounds, it is preferable to also have an alpha position occupied, as forex ample, by a sulfonic group, whether this position be para to the alpha amino group or ortho to a beta amino group.
The arylsulfonyl compounds of aminonaphthol sulfonic acids employed in the present invention may be prepared in known manner, for example,.
by acting in the dark on an aminonaphtholwith an arylsulfonyl chloride to acidylategthe amino group and esterify the hydroxy group. Suitable arylsulfonyl chlorides for :this purpose .are, ;for. example, benzenesulfonyl: chloride, ltoluenesulfonyl chloride, ohlorotoluenesulfonylchloride, and v the like. For example, there may be pp,- tained the benzenesulfonyl ester "of l-benze ne s ule fonamido-8-naphthol-4-sulfonic acid, or the 2- chloro-p-toluenesulfonyl ester of 1-(2-chloro-ptoluenesulfonamido)-8i1aphthol -3,6- disulfonic acid and the like.
If desired, the coating may :include :a light stable diazo .compound,.as .for example Levamine .Qran-ge .GSA. [-2(3 chlorobenzenediazoamino) p -.sulobenzoic acid] and after exposure .to light for example, in theform of the zinc chloride double salt, t in chloride double salt, cadmium chloride double salt, boron tetrafluoride .double salt, the chloride, sulfate, orthe like. In particular, those diazo compounds which contain one or more etherified phenolic groups are preierred. 'Examplesof diazo compounds that may .be employed are the diazo compounds of diethyl- .aminoaniline, o-dianisidine, o-phenetidin, 4- chloro-2-anisidine, 4-benzoylamino2.5-diethoxyaniline, 4-benzoylamino-2,5-dimethoxyaniline, or
.t oa hydrophilicbase or support of paper, gelatin coated cellulose acetate film or the like,preferably in the torm of the aqueous solution, and the .base so treated is thendried and is ready for. use. In particular, for developing the latent image with metalsalts, I prefer to employ mercury salts and salts of the metals above mercury in the electromotive series, as for example silvernitrate or amm'omacal silver nitrate. Where mercuric salts are employed, I use an after-treatment .with ammonia to develop a black color in the reduced mercurous image.
The invention will be described in greater de: tail in connection with the followinghexamples which are given to illustrate the invention.
Fema 1 salt of o-ethoxybenzenediazonium chloride which "results in the development of a, reddish purple positive. The print is then washed and dried.
Emample 2 .14 5 M1 s prepared t in naabeut 5 rams of 2'-chloro-p-toluenesulfonyl ester of 1-(2' chloro p toluenesulfonamido) -8-naphthol-3,6 disulfonic acid in 50 cc. water containing about -.,-0.:5,c.c. .concentrated aqueous ammonia. This so- .lution .is applied on a suitable gelatin coated paper, dried andthe coated paper is exposed to 1' 'htund r tive. The color is developed l oy treat nent t1; 1% solution of the diazonium chloride of 4-bengoyl amino-2,5-diethoxyaniline containing about 1% sodium acetate. There is thus produced a blue positive image.
Example 3 Asolution-isprepared containingabcutfil'grams ibenzenesulfonylester. of:'-'1.:-.'bnzen esu1fonamido 2, naphthol-.4=sulfonic acid in 5 Lcc. ;concentrated ammonia and cc. .water. This solution is applied son a .suitable .gelatin .coated paper, .dried, and the coated .paper is exposed to light under "a negatiue. The image may :be developed'lby dip- .ping the paper into .a bath containing about 5 rams silver nitrate tin-1100 no. .water, and than heating the =.paPer .or..exposing it to ammonia iumes. The excess silver nitratemay abe washed away-b immersion in .a:2 solution of .sodium thiqsulfate, and the apaper is then Washed and 1 *I hcpEQQeSs .iwhich com-prises exposing to li ht under a pattern tone reproduced, a *base .carryingan ,arylsulfonyl ester. of-an. arylsulfona: midonaphthol sulfom'c acid until decomposition thereof occurs, and developingthe "latent image :by reaction with a memberof the group consistring of salts .of @metals above mercury-in the electromotiwe series and diazo compounds.
12. The process which comprises exposing .to light under a pattern to .be reproduced-a xbase carrying an .arylsulionyl ester of an anylsulionamidonaphthol disulfonic-acid until decomposition thereof nccurs, and coupling the decomposed product thereof with'a diazo'com-pound.
3. The process which comprises-exposin to light under a pattern to be reproduced, abase carrying an arylsulfonyl ester of a l-arylsulfongmidoe8enaphthol sulfonic acid until decomposition thereof occurs, and coupling the decomposed product thereof witha diazo compound.
.4. The process which comprises exposing to light under a pattern to-be reproduceda base carrying an arylsul-fonylester of a l-ar-ylsulfonamidoefi-naphthol disulfonic acid until decomposition thereof occurs, and coupling the decomposed product. thereof with a diazo mm. DQ JML The r ce ss mmnrises .elgnesip to ist? under a nature .te ented car yin an arr se fieeyl este mido-2-naphthol sulfonic ac image with a salt of a metal above mercury in the electromotive series.
7. The process which comprises exposing to light under a pattern to be reproduced, a base carrying an arylsulfonyl ester of l-arylsulfonamido-2-naphthol-4-sulfonic acid until decomposition thereof occurs, and developing the latent image by couplin the decomposed product thereof with a diazo compound.
8. The process which comprises exposing to light under a pattern to be 'reprcduced, a base carrying an arylsulfonyl ester of l-arylsulfonamido-8-naphthol-3,6-disulfonic acid until decomposition thereof occurs, and developing the latent image by reaction with a member ofthe group consisting of salts of metals above mercury in the electromotive series and diazo compounds.
9. The process which comprises exposing to light under a pattern to be reproduced, a base carrying the benzenesulfonyl ester of l-benzenesulfonamido-8-naphthol-4-sulfonic acid until decomposition thereof occurs, and coupling the decomposed product thereof with a d-iazo compound of o-phenetidine.
10. The process which comprises exposing to light under a pattern to be reproduced, a base carrying 2-chlorotoluenesulfonyl ester of 1-(2- chloro-tluenesulfonamido) 8 naphthol-3,6-disulfonic acid until decomposition thereof occurs and coupling the decomposed product thereof with a diazo compound of 4-benzoylarnino-2,5- diethoxyaniline.
11. Light sensitive material which comprises a base carrying a light sensitive arylsulfonyl ester of an arylsulfonamidonaphthol sulfonic acid,
12. Light ensitive material which com-prises a base carrying a light sensitive arylsulfonyl ester of an arylsulfonamido naphthol disulfonic acid.
13. Light sensitive material which comprises a base carrying a light sensitive arylsulfonyl ester of 1-arylsulfonamido-2-naphthol disulfonic acid.
14. Light sensitive material which comprises a base carrying a light sensitive arylsulfonyl ester of a 1-arylsulfonamido-8-naphtho1-4-sulfonic acid.
15. A light sensitive material comprising a base carrying an arylsulfonyl ester of l-arylsulfonamido-8-naphthol-3,6-clisulfonic acid.
16. A light sensitive material comprising a base carrying an alpha arylsulfonyl ester of an arylsulfonamido-alpha naphthol sulfonic acid having a free position para to the hydroxyl group and wherein the hydroxy and amino groups are in different nuclei.
17. A light sensitive material comprising a base carrying a light sensitive arylsulfonyl ester of an arylsulfonamido-alpha-naphthol sulfonic acid having a free position para to the hydroxyl group.
ANDRE SCHOEN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,751,318 Gay Mar. 18, 1930 1,934,011 Schmidt et al. Nov. 7, 1933 2,034,508 DeBoer et al. Mar. 17, 1936 2,095,408 DeBoer et al. Oct. 12, 1937 2,362,598 Vittum et a1 Nov. 14, 1944 2,067,690 Alink et a1 Jan. 12, 1937 2,083,285 Alink et al. June 8, 1937 2,150,834 Holst et a1 Mar. 14, 1939 2,183,447 Dippel et al Dec. 12, 1939 2,216,137 Schmidt et a1 Oct. 1, 1940 2,311,016 Alink et al. Feb. 16, 1943 FOREIGN PATENTS Number Country Date 283,274 British Jan. 6, 1928
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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB283274A (en) * 1925-10-20 1928-01-06 Eugene Gay Process for obtaining photographic images
US1934011A (en) * 1931-01-16 1933-11-07 Kalle & Co Ag Light-sensitive layer
US2034508A (en) * 1931-05-22 1936-03-17 Philips Nv Process for obtaining contrasts by means of diazonium compounds
US2067690A (en) * 1930-02-05 1937-01-12 Philips Nv Method and material for obtaining photographic contrasts
US2083285A (en) * 1933-10-09 1937-06-08 Philips Nv Carrier comprising a diazonium compound and method of obtaining contrasts
US2095408A (en) * 1934-01-04 1937-10-12 Philips Nv Method of making negative prints
US2150834A (en) * 1936-02-17 1939-03-14 Philips Nv Sound record and method of making same
US2183447A (en) * 1937-08-09 1939-12-12 Philips Nv Light-sensitive material and method of making the same
US2216137A (en) * 1935-10-12 1940-10-01 Kalle & Co Ag Diazotype photographic printing paper
US2311016A (en) * 1934-01-19 1943-02-16 Hartford Nat Bank & Trust Co Photographic material and method of producing same
US2362598A (en) * 1939-03-31 1944-11-14 Eastman Kodak Co Color forming compounds containing sulphonamide groups

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB283274A (en) * 1925-10-20 1928-01-06 Eugene Gay Process for obtaining photographic images
US1751318A (en) * 1925-10-20 1930-03-18 Gay Eugene Process for obtaining photographic images
US2067690A (en) * 1930-02-05 1937-01-12 Philips Nv Method and material for obtaining photographic contrasts
US1934011A (en) * 1931-01-16 1933-11-07 Kalle & Co Ag Light-sensitive layer
US2034508A (en) * 1931-05-22 1936-03-17 Philips Nv Process for obtaining contrasts by means of diazonium compounds
US2083285A (en) * 1933-10-09 1937-06-08 Philips Nv Carrier comprising a diazonium compound and method of obtaining contrasts
US2095408A (en) * 1934-01-04 1937-10-12 Philips Nv Method of making negative prints
US2311016A (en) * 1934-01-19 1943-02-16 Hartford Nat Bank & Trust Co Photographic material and method of producing same
US2216137A (en) * 1935-10-12 1940-10-01 Kalle & Co Ag Diazotype photographic printing paper
US2150834A (en) * 1936-02-17 1939-03-14 Philips Nv Sound record and method of making same
US2183447A (en) * 1937-08-09 1939-12-12 Philips Nv Light-sensitive material and method of making the same
US2362598A (en) * 1939-03-31 1944-11-14 Eastman Kodak Co Color forming compounds containing sulphonamide groups

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