PROCESS FOR THE PREPARATION OF NOVEL DYES FOR USE IN IMAGING MEMBERS
There are described novel rhodamine dye compounds and imaging members and imaging methods, including thermal imaging members and imaging methods, utilizing the compounds. The dye compounds exhibit a first color when in the crystalline form and a second color, different from the first color, when in the liquid, amorphous form.
1 . A compound represented by the formula
wherein:
R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted, alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, halogen, nitro, nitrilo, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, oxygen, substituted oxygen, nitrogen, substituted nitrogen, sulfur and substituted sulfur;
R 2 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, substituted oxygen, substituted nitrogen and substituted sulfur;
R 8 is absent or selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, halogen, nitro, nitrilo, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, oxygen, substituted oxygen, nitrogen, substituted nitrogen, sulfur and substituted sulfur;
R 9 , R 10 and R 11 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, halogen, nitro, nitrilo, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, oxygen, substituted oxygen, nitrogen, substituted nitrogen, sulfur and substituted sulfur;
R 12 , R 13 , R 14 and R 15 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, aryl, substituted aryl, heteroaryl, and substituted heteroaryl;
R 16 , R 17 , R 18 and R 19 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, heterocycloalkyl, substituted heterocycloalkyl, substituted carbonyl, acylamino, halogen, nitro, nitrilo, sulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, oxygen, substituted oxygen, nitrogen, substituted nitrogen, sulfur and substituted sulfur; and
X 1 is carbon or nitrogen.
2 . A compound according to claim 1 wherein R 8 , R 9 , R 10 and R 11 are halogen, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 are as defined in claim 1 and X 1 is carbon.
3 . The imaging member comprising a first image-forming layer including a compound according to claim 1 , said compound being in the crystalline form.
4 . The imaging member as defined in claim 3 and further including a substrate and at least a second color-forming layer, said second color-forming layer being capable of forming a color different from that formed by said first color-forming layer.
5 . The imaging member as defined in claim 4 and further including a third color-forming layer, said third color-forming layer being capable of forming a color different from those formed by said first and second color-forming layers.
6 . The imaging member as defined in claim 5 wherein said color-forming layers form magenta, cyan and yellow color, respectively.
7 . The imaging method comprising
(a) providing an imaging member as defined in claim 3; and
(b) converting at least a portion of said compound to the liquid form in an imagewise pattern whereby an image is formed.
8 . The method as defined in claim 7 wherein step (b) comprises applying an imagewise pattern of thermal energy to said imaging member whereby at least a portion of said compound is converted to the liquid form and an image is formed.
9 . The thermal imaging method as defined in claim 8 wherein said imaging member further includes a substrate and at least a second color-forming layer, said second color-forming layer being capable of forming a color different from that formed by said first color-forming layer.
10 . The imaging method as defined in claim 8 wherein said imaging member further includes a third color-forming layer, said third color-forming layer being capable of forming a color different from those formed by said first and second color-forming layers.
11 . The imaging method as defined in claim 10 wherein said color-forming layers form magenta, cyan and yellow color, respectively.