US1799568A - Photographic developer and process of developing photographic materials - Google Patents

Description

Patented Apr. 7, 1931 UNITED STATES PATENT, orFlce GUSTAV REDDELIEN AND WERNER ntfiLLm-t,

NEW YORK or nnrrzro, GERMANY, ASSIGNORS ro AGFA. ANSCO CORPORATION, OF BINGHAMTON, NEW YORK, A CORPORATION OF PHOTOGRAPHIC DEVELOPER D PROCESS DEVELOPING PHOTOGRAPHIC MATERIALS No Drawing. Application filed October '1, 1928, Serial The present invention relates to new photographic developers, more particularly to developers comprising as a developing agent a compound of the general formula wherein X represents a substituent other than a nitro-group and at least one X is a substituent other than hydrogen, and to the proc-- 1o ess of developing photographic materials with these developers.

We found that photographic developers mide. N-mono-hydroxyethyl-derivatives ofnuclear substitution products or homologues 25 of 4-amino-1-hydroxybenzene were hitherto unknown, the manufacture of them has been described in our co-pending application SerialNo. 309,887, filed October 2nd, 1928, and

, consists in the condensation of nuclear sub- 1 stitution products of l-amino-l-hydrOxybenzene with a halogn-hydrin of glycol or with Suitable compositions for photographic developers in accordance with the present invention are obtained by mix- 35 ing the developing agent with the ordinary developer ingredients.-

Emample 1.-1.17 gram of the sulfate of ethyleneoxide.

4-hydroxyethyl amino-Q-chloro-l-hydroxy benzene,

9 grams of crystallized sodium sulflte and 5 grams or potassium carbonate are dissolved in 200 grams of water. j

This developer has all the valuable properties referredto in the foregoing.

Example 2.A developer of almost equal No. 303,687, and in Germany N'ovember 21, 1927.

0 activity to that of the developer described in Example 1 is made by dissolvlng in 200 grams of water v 1 gram of the oxalate of 4-hydroxyethy1amino-3-methyl-1- hydroxybenzene 3 grams of crystallized sodium sulfite and 3 grams of potassium carbonate.

E wample 3.-Another developer, which is very similar in actlon to the known l-amino- 1-hydroxybenzene-developer 1s made as follows: 1

Solution A: 3.65 grams. of 4-hydroxyethylamino-l-hydroxybenzene 2 carboxylic acid and 5 grams of crystallized sodium sulfite are dissolved in 200 grams of water.

10 grams of potassium hydroxide are dissolved in Solution B: 509 grams of water.

For use, 1 part of. solution A, 1 part of solution B and 1 part of water are mixed together.

We claim:

1. A photographic developer containing together with other developer ingredients a compound of the general formula wherein at least one X is a substituent taking the place of a hydrogen atom, which substituent, however, should not be a nitro group. 2. A photographic developer containing together with other developer ingredients a compound of the generaliformula wherein 3 Xs are hydrogen atoms and the 4th X is a substituent other than a nitro group.

3. A photographicdeveloper containing together with otherdeveloper ingredients a compound of the general formula wherein 3 Xs are hydrogen atoms and the 4th X is an alkyl roup.

4. A photograp ic developer containing 1 together with other developer ingredients a compound of the general formula HO.C X .NH.CH .OH .9H,

methyl-1-hydroxybenzene.

6. A photographic developer containing together with sodium sulfite a compound of the. general formula HO.C X .NH.CH .CH .OH, wherein 3 Xs are hydrogen atoms and the 4th X is a substituent other than a nitro group.

. 7. A photographic developer containing together with sodium sulfite a compound of the general formula wherein 3 Xs are hydrogen atoms and the 4th X is an alkyl roup.

8. A photograp ic developer containing together with sodium sulfite the oxalate of 4- hydroxyethylamino 3 methyl 1 hydroxybenzene.

9. A photographic developer 1 containing together with an alkaline solution of sodium sulfite and potassium bromide, a compound of the general formula Ho.c.x..NH.oH2.cH..o1-1,

wherein 3 Xs are hydrogen atoms and the 4th X is a substituent other than a nitro group.

10. A photographic developer containing together with an alkaline solution of sodium sulfite and potassium bromide, the oxalate of 4 hydroxyethylamino- 3-methyl-1-hydroxybenzene.

11. The process of developing photographic materials which comprises treating the same with a solution containing a compound of the general formula HOG X NHCH CH DH, wherein at least one X is a substituent taking the place of a hydrogen atom, which subwherein 3 Xs are hydrogen atoms and the 4th X is a substituent other than a nitro group.

13. The process of developing photographic materials which comprises treating the same with a solution containing a compound of the general formula wherein 3 Xs are hydrogen atoms and the 4th X is an alkyl group.

14. The process of developing photographic materials which comprises treating the same with a solution containing a compound of the general formula wherein 3 Xs are hydrogent'atoms and the 4th X is a methyl group.

15. The process of developing photographic materials which comprises treating the same with a solution containing the 0xalate of 4-hydroxyethylamino-3-methyl-lhydroxybenzene.

16. The process of developing photographic materials which comprises treating the same with a solution containing together with other developer ingredients a compound of the general formula Ho.o.x..NH.oH..on..oH,

wherein 3 Xs are hydrogen atoms and the 4th X is. a substituent other than a nitro group.

17. The process of developing photographic materials which comprises treating the same with a solution containing together with other developer ingredients the oxalate of 4 hydroxyethylamino 3 methyl- 1 -hydroxybenzene.

18. The process of developing photographic materials which comprises treating the same with a solution containing sodium sulfite and a compound of the general formula HO.C X .NH.CH .CH .OH, wherein 3 Xs are hydrogen atoms and the 4th X is a substituent other than a nitro group.

19. The process of developing photographic materials which comprises treating the same with an alkaline solution of sodium sulfite and a compound of the general 20. The process of developing photo-- graphic materials which comprises treating the same with a solution containing sodium sulfite, potassium carbonate, and the oxalate of 4 hydroxyethylamino 3 methyl- 1 -hydroxybenzene.

In testimony whereof, We afiix our signatures.

GUSTAV REDDELIEN.

WERNER MULLER.