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Publication numberUS1845989 A
Publication typeGrant
Publication dateFeb 16, 1932
Filing dateOct 23, 1929
Priority dateNov 3, 1928
Publication numberUS 1845989 A, US 1845989A, US-A-1845989, US1845989 A, US1845989A
InventorsPaul Schmidt Maximilian, Rudolf Zahn
Original AssigneeKalle & Co Ag
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Light-sensitive layers and process of preparing them
US 1845989 A
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Description  (OCR text may contain errors)

Patented Feb. 16, 1932 UNITED STATES PATENT OFFICE MAXIMILLAN PAUL SCHMIDT AND RUDOLF ZAHN, OF WIESBADEN-BIEBRICH, GER- MANY, ASSIGNORS '10 KALLE & C0. ARTIENGESELLSCHAFT, OF BIEBRICH-ON-THE- name, GERMANY LIGHT-SENSITIVE LAYERS AND PROCESS OF PREPARING- THEM No Drawing. Application filed October 23, 1929, Serial No. 401,964, and 111 GermanyNoveinber 3, 1928.

The present invention relates to light sensitive layers and to a process of preparing them.

We have found that light sensitive layers can be produced with the aid of an arylazide which can be prepared in a known manner,

. for instance, by causing a diazo compound to react with sodium arylazide.

For the preparation of the light-sensitive layer the arylazide is dissolved in water or in an organic solvent, such as, for instance, alcohol; the solution is then applied on a base, for instance, paper or film. Whenthe layers are exposed to light, dyestuffs are formed at those places wherethe light is allowed to react, whilst the places not exposed to light remain unaltered. Thus by exposure to light behind a negative a positive picture is obfor instance, gelatine, collodion and other bodies. Mixtures of azides may also be used. it stabilizer, such, as for instance,glucose, tartaric acid and the salts thereof and aromatic sulpho acids, may also be added to the layer. fitter the exposure to light, a simple washing out with water or another suitable soivent is suficient in order to render the pic tures permanent.

The following examples serve to illustrate the invention, but they are not intended to limit it thereto, the parts being given by weight, except where otherwise specified.

1. it neutral or weakly alkaline aqueous solution of 3% strength obtained by causing diaao salicyclic acid to react with sodium azide is spread upon paper. The paper is exposed to light under a negative and the picture thus obtained is washed with water. A brown positive copy is obtained. It the light-sensitive solution is rendered weakly acidl'a yellowish copy is obtained.

2. 2.5 parts of 4-azido-1.2-phenolcarboxylic acid are dissolved in 50 parts by VOlume of water with the addition of just the required quantity of caustic soda solution. 0.3 parts of boric acid and 0.6 parts of tartaric acid are added to the solution. salicyclic acid which will have partly separated outis again dissolved with diluted caustic soda solution. The gelatine layer of the paper is impregnated wlth the solution obtained. After exposure to light under a negative and subsequent Washing, pictures of a brown tone are obtained. Instead of impregnating the gelatine layer, the l-azidosalicyclic acid may also be applied upon the paper in the form of a gelatine emulsion.

' 3. 2 parts of i-azido-1.2-phenolcarboxylic acid are dissolved in 25 parts by volume of water with the addition of some ammonia. The solution thus obtained is mixed with 0.5 parts of copper sulfate. Any portions which may separate out are again dissolved by adding some caustic soda solution. If this solution is applied on barium paper, allowed to dry and exposed to light under a negative, a positive picture is obtained, which after the washing operation has a brownish-yellow tone.

It a paper prepared according to Example 3, in which the copper sulfate is replaced by 0.5 parts of zinc chloride is employed, then by working according to the same The azidomethod, pictures of a brownish violet tone are obtained. It the same weight of titanic oxalate be substituted for copper sulfate, pictu'res of a brownish-red tone are obtained by working in a similar manner. It instead of the copper sulfate 0.7 parts of nickel chlo ride are used, dark black tones are obtained on gelatine paper.

4. 1 part of paraazidodiphenylamine carboxylic acid of the formula:

COOH

is dissolved with some diluted caustic soda solutionin 25 parts by volume of Water;

the solution thus obtained is applied on paper. After exposure to light under a negative and subsequent washing with'water, pictures of a brownish-yellow tone are obtained.

5. 4 parts of4-azido-1.2-phenolcarboxylic acid are dissolved in 50 parts by volume of water together with 1.3 parts of azidodiphenylamino carboxylic acid and 0.4 parts of glucose with the addition of'some ammonia." Gelatine paper is'rendered sensitive to light by means of this solution and the paper is then exposed to light under a negative. According to' the length of time dur-.

ing which the pictures are exposed to light, positive pictures are obtained, the tones of which vary fromdark brown to black.

6. 1 part of 1-azido-2-chloro-4-dimethyl- I amino-benzene is dissolved in 25 parts by volume of water with the addition of some dilute hydrochloric .acid. When the solution thus obtained is applied on paper, positive pictures of brownish-orange tones are obtained after exposure to light under a negative and subsequent washing.

7.2 parts of 4- ara-tolyl-sulfonylamino- 1-azido-benzene o the formula:

are dissolved with some dilute caustic soda solution in 20 parts by volume-of water. The papers impregnated with the solution thus obtained yield, after exposure to light under a negative and subsequent washing, positive pictures of brownish yellow tones.

Thev above named azido compound may also be employed without the addition of alkali by applying it in an alcoholic solution on paper. The pictures obtained by exposure to light under a negative must in this case be washed with alcohol in order to remove the non-used azido compound.

8. 2 parts of para-toly1-sulfo-3-amino-1 azidorbenzene are dissolved in 20 parts by volume of water with 'the addition of some dilute caustic soda solution.

The solution thus obtained is applied on paper. After exposure to light under a negative and wash ing with water, positive pictures of yellow tones are obtained.

9. 1 gram of the sodium salt of the diazidodiphenylamine carboxylic acid of the formula We claim:

1. Process of preparing light-sensitive layers upon a suitable base, which comprises applying an aryl-azide upon said base.

2. Process of preparing light-sensitive layers upon a suita le base, which comprises applying a substituted arylazide upon said base. 3.

I recess of preparing light-sensitive layers upon a suitable base which comprises applymga compound of the following formula:

NQX x x whereinthe Xs stand for hydrogen atoms some of which may be substituted by OH, COOH, N halogen, aryl, aralkyl, oxalkyl,

alkyl, an amino group substituted or not or a sulfo group upon said base.

4:- Process of preparing light-sensitive layers upon a suitable base, which comprises applying a compound of the following formula wherein one X stands for hydroxy or amino group substituted or not and the other Xs stand for hydrogen atoms some of which may be substituted by OH, COOH, N halo- 1 gen, aryl, alkyl, aralkyl, oxyalkyl or a sulfo grougupon said base.

v 5. rocess of preparing light-sensitive layers upon a suitable base, which'comprises applying a compound of the following formula:

X P X wherein one X may stand for 0001-1 and one 115 for OH and the other Xs for H upon said ase.

6. Process of preparing light-sensitive layersupon a suitable base, which comprises ap- Na-QOH con upon any desired base.

' 7. Processof preparing light-sensitive layers upon a suitable base, which comprises applying an arylazide and a metallic salt used in the diaZo-type processu-pon said base.

8. Process of preparing light-sensitive layers upon a suitable base, which comprises applying a compound of the following formu a:

wherein one X stands for hydroxy or amino plying a compound of the following formula:

group substituted or not and the other Xs stand for hydrogen atoms some of which may be substituted by OH, COOH, N halogen, aryl, allryl, aralkyl, oxyalkyl or a sulfo group and a metallic salt used in the diazo-type process upon said base.

9. Process of preparing light-sensitive layers upon a suitable base, which comprises applying an arylazide, a metallic salt used in the diazo-type process and a colloid upon said base.

10. Process of )reparing light-sensitive layers upon a suite le base, which comprises applying an arylazide, a metallic salt used in the diazo-type process and gelatine upon said base.

11. As new products, light-sensitive layers containing an arylazide.

12. As new products, light-sensitivelayers containing a substituted arylazide.

13. As new products, light-sensitive layers containing a coinpound of the following general formula: i

wherein the Ks stand for hydrogen atoms some of "whichmay be substituted by OH, UOOH, N halogen, aryl, alkyl, aralkyl oxy-. alkyl, an amino group substituted or not or a sulfo group. i

14. As new. products, light-sensitive lay-- ers containing a compound of the following formula formula wherein one X may stand for COOH and I one X for OH and the other Xs for H.

16. As new products, light-sensitive laym ore containing a compound of the following formula 2 Nr-QOH coon 1'3. As new products, light-sensitive layformula x x NQX x 2:

wherein one X stands for hyd-roxyor amino group substituted or not and the other Xs stand for hydrogen atoms some of which may be substituted by OH, COOH, N halogen,'aryl, alkyl, aralkyl, oxyalkyl or a sulfo group and a metallic salt used in the diazotype process.

19. As new products, light-sensitive layers containing an arylazide, a metallic salt used in the diazo-type process and a colloid.

20. As new products, light-sensitive layers containing an arylazide, a metallic salt used in the diazo-type process and gelatine.

In testimony whereof, we afiix our signatures.

MAXIMILIAN PAUL SCHMIDT. RUDOLF ZAHN.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2416773 *Jan 4, 1945Mar 4, 1947Gen Aniline & Film CorpStabilized diazotype photoprinting materials
US2537097 *Aug 18, 1945Jan 9, 1951Gen Aniline & Film CorpDyeing of textile materials by the use of light-sensitive diazo salts
US2541178 *Oct 24, 1946Feb 13, 1951Gen Aniline & Film CorpPhotographic process for dyeing of textile materials
US2542715 *Dec 5, 1947Feb 20, 1951Gen Aniline & Film CorpMulticolor diazotype layers
US2542716 *Dec 5, 1947Feb 20, 1951Gen Aniline & Film CorpMulticolor diazotype layers
US2687958 *May 10, 1950Aug 31, 1954Azoplate CorpLight-sensitive layers for the printing industry
US3092494 *May 19, 1954Jun 4, 1963Azoplate CorpLight sensitive azides, printing plates comprising such compounds and process for the production thereof
US3617278 *Mar 20, 1968Nov 2, 1971Eastman Kodak CoAzide sensitizers and photographic elements
US3660093 *Jul 2, 1969May 2, 1972Agfa Gevaert AgDry azido thermal diffusion copying process
US3716367 *May 26, 1971Feb 13, 1973American Cyanamid CoN-succinimide additives for azide imaging systems
US3844793 *Dec 8, 1972Oct 29, 1974American Cyanamid CoPhotosensitive azido material
US3933497 *Jun 27, 1974Jan 20, 1976American Cyanamid CompanyPhotosensitive azido processes
US4003747 *Sep 4, 1975Jan 18, 1977Hodogaya Chemical Co., Ltd.Photosensitive azide compound containing color-forming element
US4019907 *Oct 17, 1974Apr 26, 1977Hodogaya Chemical Co., Ltd.Photosensitive azido color-forming element
US4549824 *Dec 30, 1983Oct 29, 1985International Business Machines CorporationInk additives for efficient thermal ink transfer printing processes
Classifications
U.S. Classification430/195, 430/196, 430/194, 430/197, 430/147
International ClassificationG03C1/695
Cooperative ClassificationG03C1/695
European ClassificationG03C1/695