Light-sensitive diazo compounds and reproduction material employing the same

• US 3,867,147 A
• Filed: 10/29/1973
• Issued: 02/18/1975
• Est. Priority Date: 05/20/1969
• Status: Expired due to Term

• Current Assignee: Leon A. Teuscher
• Original Assignee: Leon A. Teuscher
• Inventors: Teuscher, Leon A.
• Primary Examiner(s): Bowers, Jr., Charles L.
• Application Number:
  US05/410,324
• Time in Patent Office: 477 Days
• Field of Search: 96/33,36.1,49,75,91,86R,86P,115R,35.1 260/141,142
• US Class Current: 430/157
• CPC Class Codes: C08G 12/08 aromatic
• CPC Class Codes: C08G 12/22 with carboxylic acid amides reaction of polyamides with aldehydes C08G69/50
• CPC Class Codes: C08G 16/02 of aldehydes
• CPC Class Codes: C08G 8/28 Chemically modified polycondensates
• CPC Class Codes: G03C 7/08 from diversely-coloured grains irregularly distributed
• CPC Class Codes: G03F 7/021 Macromolecular diazonium compounds; Macromolecular additives, e.g. binders G03F7/0166 takes precedence

Abstract

This invention relates to novel light-sensitive compounds, a process for the preparation of the light-sensitive compounds, and the use of the light-sensitive compounds, the latter being, in each case, a condensation product of an aromatic diazonium compound which comprises repeating units of each of the general types

Claims

1. AN AROMATIC DIAZONIUM COMPOUND COMPRISING REPEATING UNITS OF EACH OF THE GENERAL TYPES A - N2X AND B WHICH ARE LINKED BY METHYLENE GROUPS, IN WHICH A-N2X IS A RADICAL OF A COMPOUND OF ONE OF THE GENERAL FORMULAE

2. A compound according to claim 1 having a molecular weight from 500 to 10,000.

3. A compound according to claim 1 in which the compound of which A is a radical is a 2,4'"'"''"'"',5-triethoxy-diphenyl-4-diazonium salt.

4. A compound according to claim 1 in which the compound of which A is a radical is a 4-(4-methyl-phenylmercapto)-2,5-dimethoxy-benzene diazonium salt.

5. A compound according to claim 1 in which the compound of which A is a radical is a 4-(4-methoxy-phenyl-mercapto)-2,5-diethoxy-benzene diazonium salt.

6. A compound according to claim 1 containing, on the average, about 0.1 to 20 B units per unit of A-N2X.

7. A compound according to claim 1 in which the A-N2X units are derived from a compound of the general formula

8. A compound according to claim 1 in which the compound of which B is a radical is an aromatic amine.

9. A compound according to claim 1 in which the compound of which B is a radical is a phenol.

10. A compound according to claim 1 in which the compound of which B is a radical is an aromatic heterocyclic compound.

11. A compound according to claim 1 in which the compound of which B is a radical is a phenolic ether.

12. A compound according to claim 1 in which the compound of which B is a radical is an aromatic thioether.

13. A compound according to claim 1 in which the compound of which B is a radical is an aromatic hydrocarbon.

14. A compound according to claim 1 in which the compound of which B is a radical is an organic acid amide.

15. A compound according to claim 14 in which the compound of which B is a radical is a carboxylic acid amide.

16. A compound according to claim 14 in which the compound of which B is a radical is a sulfonic acid amide.

17. A compound according to claim 1 in which the compound of which A is a radical is a diazo diphenylamine and the compound of which B is a radical is selected from the group consisting of diphenyl ethers and diphenyl sulfides.

18. A compound according to claim 1 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium dihydrogenphosphate and the compound of which B is a radical is 4-methyl-diphenylamine.

19. A compound according to claim 1 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium chloride and the compound of which B is a radical is phenol.

20. A compound according to claim 1 in which the compound of which A is a radical is diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is mesitylene.

21. A compound according to claim 1 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is 1,3-diisopropyl-benzene.

22. A compound according to claim 1 in which the compound of which A is a radical is diphenylamine-4-diazonium hydrogen sulfate and the compound of which B is a radical is anisole.

23. A compound according to claim 1 in which the compound of which A is a radical is diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is a mixture of phenanthrene and benzene.

24. A compound according to claim 1 in which the compound of which A is a radical is diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is 3-methylphenoxymethyl phosphonic acid.

25. A compound according to claim 1 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is diphenyl methane.

26. A compound according to claim 1 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium chloride, zinc chloride double salt, and the compound of which B is a radical is diphenyl ether.

27. A compound according to claim 1 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is diphenyl sulfide.

28. A compound according to claim 1 in which the compound of which A is a radical is diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is diphenyleneoxide.

29. A compound according to claim 1 in which the compound of which A is a radical is a mixture of diphenylamine-4-diazonium dihydrogenphosphate and 3-methoxy-diphenylamine-4-diazonium dihydrogenphosphate and the compound of which B is a radical is thiophene.

30. A PROCESS FOR THE PREPARATION OF AN AROMATIC DIAZONIUM COMPOUND WHICH COMPRISES REACTING ONE MOLAR PART OF AT LEAST ONE COMPOUND OF ONE OF THE GENERAL FORMULAE

31. A process according to claim 30 which comprises reacting one molar part of a compound of the general formula

32. A process according to claim 30 in which the condensation medium used is a concentrated acid.

33. A process according to claim 32 in which the condensation medium used is selected from the group consisting of phosphoric acid, methane sulfonic acid, and sulfuric acid, in a concentration in the range of about 70 to 100%.

34. A process according to claim 50 in which the condensation is performed in a temperature range of about 10*C. to 50*C.

35. LIGHT-SENSITIVE MATERIAL COMPRISING A BASE MATERIAL HAVING A LAYER THEREON INCLUDING AN AROMATIC DIAZONIUM COMPOUND COMPRISING REPEATING UNITS OF EACH OF THE GENERAL TYPES A-N2X AND B WHICH ARE LINKED BY METHYLENE GROUPS, IN WHICH A-N2X IS A RADICAL OF A COMPOUND OF ONE OF THE GENERAL FORMULAE

36. Light-sensitive material according to claim 35 in which the base material is a screen.

37. Light-sensitive material according to claim 35 in which the diazonium compound contains, on the average, about 0.1 to 20 B units per unit of A-N2X.

38. Light-sensitive material according to claim 35 in which the A-N2X units are derived from a compound of the general formula

39. Light-sensitive material according to claim 35 in which the compound of which B is a radical is an aromatic amine.

40. Light-sensitive material according to claim 37 in which the compound of which B is a radical is a phenol.

41. Light-sensitive material according to claim 35 in which the compound of which B is a radical an aromatic heterocyclic compound.

42. Light-sensitive material according to claim 35 in which the compound of which B is a radical is a phenolic ether.

43. Light-sensitive material according to claim 35 in which the compound of which B is a radical is an aromatic thioether.

44. Light-sensitive material according to claim 35 in which the compound of which B is a radical is an aromatic hydrocarbon.

45. Light-sensitive material according to claim 35 in which the compound of which B is a radical is an organic acid amide.

46. Light-sensitive material according to claim 45 in which the compound of which B is a radical is carboxylic acid amide.

47. Light-sensitive material according to claim 45 in which the compound of which B is a radical is sulfonic acid amide.

48. Light-sensitive material according to claim 35 in which the compound of which A is a radical is a diazo diphenylamine and the compound of which B is a radical is selected from the group consisting of diphenyl ethers and diphenyl sulfides.

49. Light-sensitive material according to claim 35 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium dihydrogenphosphate and the compound of which B is a radical is 4-methyl-diphenylamine.

50. Light-sensitive material according to claim 35 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium chloride and the compound of which B is a radical is phenol.

51. Light-sensitive material according to claim 35 in which the compound of which A is a radical is diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is mesitylene.

52. Light-sensitive material according to claim 35 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium hydrogen sulfate and the compound of which B is a radical is 1,3-diisopropyl-benzene.

53. Light-sensitive material according to claim 35 in which the compound of whiCh A is a radical is diphenylamine-4-diazonium hydrogen sulfate and the compound of which B is a radical is anisole.

54. Light-sensitive material according to claim 35 in which the compound of which A is a radical is diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is a mixture of phenanthrene and benzene.

55. Light-sensitive material according to claim 35 in which the compound of which A is a radical is diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is 3-methylphenoxymethyl phosphonic acid.

56. Light-sensitive material according to claim 35 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is diphenyl methane.

57. Light-sensitive material according to claim 35 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium chloride, zinc chloride double salt, and the compound of which B is a radical is diphenyl ether.

58. Light-sensitive material according to claim 35 in which the compound of which A is a radical is 3-methoxy-diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is diphenyl sulfide.

59. Light-sensitive material according to claim 35 in which the compound of which A is a radical is diphenylamine-4-diazonium hydrogensulfate and the compound of which B is a radical is diphenyleneoxide.

60. Light-sensitive material according to claim 35 in which the compound of which A is a radical is a mixture of diphenylamine-4-diazonium dihydrogenphosphate and 3-methoxy-diphenylamine-4-diazonium diphydrogenphosphate and the compound of which B is a radical is thiophene.

61. Light-sensitive material according to claim 35 in which the base material is aluminum.

62. Light-sensitive material according to claim 35 in which the base material is paper.