OXAZINE LEUCO DYES AND APPLICATIONS

2.3.1. Acylated Oxazine Leuco Dyes

Benzoyl leuco Basic Blue 3 (2) is a typical cyan leuco oxazine used in carbonless copy paper. To satisfy the requirements of new applications such as electrolytic recording and Color Dry Silver, new oxazine leucos have been
developed that can offer colors other than cyan such as red, purple, and blue violet.

The introduction of electron-withdrawing groups on the exocyclic amino groups of the oxazine dyes is one method employed to create a hypsochromic shift and obtain colors ranging from orange to violet.6 The redox potential of the new dyes is probably raised owing to the presence of the electron-withdrawing groups which leads to the nonacylated leuco oxazine dyes being stable enough to be isolated, as shown in Table 2.

The reductive acetylation of Brilliant Cresyl Blue (29) yields 1,9- dimethyl-4-acetamido-8-diethylaminoimidazophenoxazine (30) which gives a purple image in electrolytic recording.12 Other similar oxazine leucos (31-34) have also been developed for electrolytic recording.13 The leucos 33 and 34 produce blue violet images.

^H2 )=N

НзС Ac^Pyridine H3CV^4^NS>.

Подпись: JHCOCH3

(H5c2)2N^^o^ANH] ^5c2)2n^^°^^n

OXAZINE LEUCO DYES AND APPLICATIONS OXAZINE LEUCO DYES AND APPLICATIONS

(29) (30)

Table 2. Effect of Substituents on the Color of Oxazine Dyes

OXAZINE LEUCO DYES AND APPLICATIONS

(28)

R1

R2

Dye color

a

COCF3

H

Purple

b

SO2CH3

H

Orange

c

COCF3

CONHC4H9

Purple

d

COC13

conhc4h9

Magenta

e

COCHC12

conhc4h9

Red

f

ch2cf3

COCF3

Blue (595 nm)

g

H

COC6H5

Green

h

CO2C2H5

COC66H55

Red

i

CO2C2H5

CONHC4H9

Purple

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