Azine redox dyes and leuco azine dyes

• US 4,710,570 A
• Filed: 09/30/1985
• Issued: 12/01/1987
• Est. Priority Date: 10/01/1984
• Status: Expired due to Fees

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Thien, Tran V.
• Primary Examiner(s): Raymond, Richard L.
• Application Number:
  US06/781,913
• Time in Patent Office: 792 Days
• Field of Search: 544/31, 544/34, 544/35, 544/99, 544/101, 544/102, 544/104
• US Class Current: 544/31
• CPC Class Codes: B41M 5/136 Organic colour formers, e.g. leuco dyes
• CPC Class Codes: B41M 5/323 Organic colour formers, e.g. leuco dyes
• CPC Class Codes: C07D 241/46 Phenazines
• CPC Class Codes: C07D 265/36 condensed with one six-membered ring
• CPC Class Codes: C07D 279/20 with hydrogen atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 413/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 513/04 Ortho-condensed systems
• CPC Class Codes: C09B 17/02 of the benzene series
• CPC Class Codes: C09B 19/00 Oxazine dyes
• CPC Class Codes: C09B 21/00 Thiazine dyes
• CPC Class Codes: G03C 1/49854 Dyes or precursors of dyes for diffusion-transfer G03C8/10, G03C8/4013

Abstract

Azine redox dyes and their corresponding dyes of the formula: ##STR1## in which: X is O, S, NR²,

Z completes a fused aromatic of heterocyclic ring system,

n is 0 or 1 to allow one R¹ ring substituent,

Q represents CR⁴ R⁵ in which at least one of R⁴ and R⁵ is an electronegative group or R⁴ and R⁵ may complete a ring, or

when X is S Q may represent NR³ in which R³ is an aromatic or heterocyclic group.

The leuco dyes are useful as dye generators in pressure sensitive, thermographic or photothermographic imaging systems.

Claims

1. A compound of the general formula:

##STR67## in which;

X represents O or S;

Z represents the necessary atoms to complete a fused aromatic or heterocyclic ring system, which may be polynuclear, of up to 16 skeletal atoms selected from carbon and nitrogen;

n is 0 or 1;

R¹ represents an alkyl or aromatic sulphonyl group, containing up to 15 skeletal atoms selected from carbon, nitrogen, oxygen, and sulphur;

Q represents CR⁴ R⁵

in which

R⁴ and R⁵ each contain up to 20 skeletal atoms selected from carbon, nitrogen, oxygen and sulphur, at least one of R⁴ and R⁵ is selected from the group consisting of electronegative groups selected from the group consisting of carbonyl, cyano and sulphonyl groups, and substituted aryl groups, and the other of R⁴ and R⁵ may additionally be selected from aryl, alkoxy, thioalkoxy, alkylamino and arylamino, or R⁴ and R⁵ together comprise the necessary atoms to form a 5-membered α

-oxoheterocyclic ring, and when X represents O, R⁴ and R⁵ together may additionally comprise the necessary atoms to form a 6-membered α

-oxoheterocyclic ring.

2. A compound as claimed in claim 1, in which Z represents a fused phenyl ring or pyridine ring optionally substituted by a perfluoroalkyl group.

3. A compound as claimed in claim 1, in which R¹ is selected from an arylsulphonyl group optionally substituted by alkyl, alkoxy, halogen, nitro and a further fused ring, and a perfluoroalkylsulphonyl group.

4. A compound as claimed in any of claim 1, in which Q is CR⁴ R⁵ and R⁴ and R⁵ are selected from carboxy, carboalkoxy, carboaryloxy, carbamido, arylaminocarbonyl, cyano, optionally perfluorinated alkylsulphonyl, arylsulphonyl, sulphamido, nitroaryl, cyanoaryl, alkanoyl, and aroyl or R⁴ and R⁵ together form a 5-membered α

-oxoheterocyclic ring selected from oxazolidinone, thioxo oxazolidone, thiazolidone, thioxothiazolidone, oxazolone, thiazolone, pyrazolone, isoxazolone, isothiazolone, diazolidinedione and indanone, optionally substituted by one or more alkyl, aryl or fused ring groups.

5. A compound as claimed in any of claim 1, in which X represents O, and R⁴ and R⁵ together comprise the necessary atoms to form a 6-membered α

-oxoheterocyclic ring selected from oxoisocoumarin and 1,3-dioxane-4,6-dione.

6. The compound of claim 1 wherein said at least one of R⁴ and R⁵ is an electronegative group selected from the group consisting of carbonyl, cyano and sulfonyl groups.

7. The compound of claim 2 wherein said at least one of R⁴ and R⁵ is an electronegative group selected from the group consisting of carbonyl, cyano and sulfonyl groups.

8. The compound of claim 3 wherein said at least one of R⁴ and R⁵ is an electronegative group selected from the group consisting of carbonyl, cyano and sulfonyl groups.

9. The compound of claim 4 wherein said at least one of R⁴ and R⁵ is an electronegative group selected from the group consisting of carbonyl, cyano and sulfonyl groups.

10. The compound of claim 5 wherein said at least one of R⁴ and R⁵ is an electronegative group selected from the group consisting of carbonyl, cyano and sulfonyl groups.

11. The compound of claim 1 wherein one of R⁴ and R⁵ is an aryl group.

12. The compound of claim 1 wherein said at least one of R⁴ and R⁵ is an aryl group having a substituent selected from the group consisting of alkyl, alkoxy and fused ring groups.