Mixture of dyes for cyan dye donor for thermal color proofing

Claim 2

A cyan dye-donor element for thermal dye transfer comprising a support having thereon a dye layer comprising a mixture of cyan dyes dispersed in a polymeric binder, at least one of the cyan dyes having the formula: ##STR23## wherein: R 1 and R 2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 6 carbon atoms; a substituted or unsubstituted cycloalkyl group having from about 5 to about 7 carbon atoms; a substituted or unsubstituted allyl group; or a substituted or unsubstituted aryl or hetaryl group having from about 6 to about 10 carbon atoms; or R 1 and R 2 represent atoms which can be joined together to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring; or either or both of R 1 and R 2 together with one or two of R 3 represent atoms which can form a 5- to 7-membered heterocyclic ring; each R 3 independently represents substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl as described above for R 1 and R 2 ; alkoxy, aryloxy, halogen, nitro, cyano, thiocyano, hydroxy, acyloxy, acyl, alkoxycarbonyl, aminocarbonyl, alkoxycarbonyloxy, carbamoyloxy, acylamido, ureido, imido, alkylsulfonyl, arylsulfonyl, alkylsulfonamido, arylsulfonamido, alkylthio, arylthio or trifluoromethyl; or atoms at any two adjacent positions of R 3 may be combined together to form a 5-or 6-membered carbocyclic or heterocyclic ring; m is an integer of from 0 to 4; R 4 represents R 5 , alkylthio or arylthio, with the proviso that when R 4 is alkylthio or arylthio, then m must be at least 1; and R 5 represents a substituted or unsubstituted aryl or hetaryl group as described above for R 1 and R 2 ; and at least one of the other of the dyes having the formula: ##STR24## wherein: R 1 , R 2 , R 3 and m represent the same as above; X represents hydrogen, halogen or may be combined together with Y to represent the atoms necessary to complete a 6-membered aromatic ring, thus forming a fused bicyclic quinoneimine, such as a naphthoquinoneimine; with the proviso that when X is hydrogen, then J represents NHCOR F , where R F represents a perfluorinated alkyl or aryl group; and with the further proviso that when X is halogen, then J represents NHCOR 6 , NHCO 2 R 6 , NHCONHR 6 or NHSO 2 R 6 ; and with the further proviso that when X is combined with Y, then J represents CONHR 6 , SO 2 NHR 6 , CN, SO 2 R 6 or SCN; R 6 is a substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl group as defined for R 1 above; and Y is R 1 , acylamino or may be combined together with X as described above.

Claim 3

The element of claim 1 wherein in formula I, R 1 and R 2 are each C 2 H 5 and R 3 is hydrogen or CH 3 .

Claim 4

The element of claim 1 wherein in formula I, R 4 is C 6 H 5 or C 6 H 5 S and R 5 is C 6 H 5 .

Claim 5

The element of claim 1 wherein in formula I, R 1 and R 2 are each C 2 H 5 , R 3 is hydrogen, and R 4 and R 5 are each C 6 H 5 .

Claim 6

The element of claim 1 wherein in formula I, R 1 and R 2 are each C 2 H 5 , R 3 is CH 3 , R 4 is C 6 H 5 S and R 5 is C 6 H 5 .

Claim 7

The element of claim 1 wherein in formula II, R 3 is H, CH 3 , OCH 3 , or OC 2 H 5 and Y is C 2 H 5 or NHCOCH 2 OCH 3 .

Claim 8

The element of claim 1 wherein in formula II, X is H and J is NHCOC 3 F 7 or X is Cl and J is NHCOCH 2 OCH 3 .

Claim 9

The element of claim 1 wherein in formula II, Y and X are joined together to form a 6-membered aromatic ring and J is CONHCH 3 .

Claim 10

The element of claim 1 wherein in formula II, X is Cl, J is NHCOCH 2 OCH 3 , R 3 is CH 3 and Y is C 2 H 5 .

Claim 11

The element of claim 1 wherein in formula II, J is CONHCH 3 , R 3 is CH 3 and X and Y are joined together to form a 6-membered aromatic ring.

Claim 12

The element of claim 1 wherein said dye-donor element contains an infrared-absorbing dye in said dye layer.

Claim 13

In a process of forming a dye transfer image comprising imagewise-heating a cyan dye-donor element comprising a support having thereon a dye layer comprising a mixture of cyan dyes dispersed in a polymeric binder, at least one of the cyan dyes having the formula: ##STR25## wherein: R 1 and R 2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 6 carbon atoms; a substituted or unsubstituted cycloalkyl group having from about 5 to about 7 carbon atoms; a substituted or unsubstituted allyl group; or a substituted or unsubstituted aryl or hetaryl group having from about 6 to about 10 carbon atoms; or R 1 and R 2 represent atoms which can be joined together to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring; or either or both of R 1 and R 2 together with one or two of R 3 represent atoms which can form a 5- to 7-membered heterocyclic ring; each R 3 independently represents substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl as described above for R 1 and R 2 ; alkoxy, aryloxy, halogen, nitro, cyano, thiocyano, hydroxy, acyloxy, acyl, alkoxycarbonyl, aminocarbonyl, alkoxycarbonyloxy, carbamoyloxy, acylamido, ureido, imido, alkylsulfonyl, arylsulfonyl, alkylsulfonamido, arylsulfonamido, alkylthio, arylthio or trifluoromethyl; or atoms at any two adjacent positions of R 3 may be combined together to form a 5-or 6-membered carbocyclic or heterocyclic ring; m is an integer of from 0 to 4; R 4 represents R 5 , alkylthio or arylthio, with the proviso that when R 4 is alkylthio or arylthio, then m must be at least 1; and R 5 represents a substituted or unsubstituted aryl or hetaryl group as described above for R 1 and R 2 ; and at least one of the other of the dyes having the formula: ##STR26## wherein: R 1 , R 2 , R 3 and m represent the same as above; X represents hydrogen, halogen or may be combined together with Y to represent the atoms necessary to complete a 6-membered aromatic ring, thus forming a fused bicyclic quinoneimine, such as a naphthoquinoneimine; with the proviso that when X is hydrogen, then J represents NHCOR F , where R F represents a perfluorinated alkyl or aryl group; and with the further proviso that when X is halogen, then J represents NHCOR 6 , NHCO 2 R 6 , NHCONHR 6 or NHSO 2 R 6 ; and with the further proviso that when X is combined with Y, then J represents CONHR 6 , SO 2 NHR 6 , CN, SO 2 R 6 or SCN; R 6 is a substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl group as defined for R 1 above; and Y is R 1 , acylamino or may be combined together with X as described above.

Claim 14

In a process of forming a dye transfer image comprising imagewise-heating a cyan dye-donor element comprising a support having thereon a dye layer comprising a mixture of cyan dyes dispersed in a polymeric binder, at least one of the cyan dyes having the formula: ##STR25## wherein: R 1 and R 2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 6 carbon atoms; a substituted or unsubstituted cycloalkyl group having from about 5 to about 7 carbon atoms; a substituted or unsubstituted allyl group; or a substituted or unsubstituted aryl or hetaryl group having from about 6 to about 10 carbon atoms; or R 1 and R 2 represent atoms which can be joined together to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring; or either or both of R 1 and R 2 together with one or two of R 3 represent atoms which can form a 5- to 7-membered heterocyclic ring; each R 3 independently represents substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl as described above for R 1 and R 2 ; alkoxy, aryloxy, halogen, nitro, cyano, thiocyano, hydroxy, acyloxy, acyl, alkoxycarbonyl, aminocarbonyl, alkoxycarbonyloxy, carbamoyloxy, acylamido, ureido, imido, alkylsulfonyl, arylsulfonyl, alkylsulfonamido, arylsulfonamido, alkylthio, arylthio or trifluoromethyl; or atoms at any two adjacent positions of R 3 may be combined together to form a 5-or 6-membered carbocyclic or heterocyclic ring; m is an integer of from 0 to 4; R 4 represents R 5 , alkylthio or arylthio, with the proviso that when R 4 is alkylthio or arylthio, then m must be at least 1; and R 5 represents a substituted or unsubstituted aryl or hetaryl group as described above for R 1 and R 2 ; and at least one of the other of the dyes having the formula: ##STR26## wherein: R 1 , R 2 , R 3 and m represent the same as above; X represents hydrogen, halogen or may be combined together with Y to represent the atoms necessary to complete a 6-membered aromatic ring, thus forming a fused bicyclic quinoneimine, such as a naphthoquinoneimine; with the proviso that when X is hydrogen, then J represents NHCOR F , where R F represents a perfluorinated alkyl or aryl group; and with the further proviso that when X is halogen, then J represents NHCOR 6 , NHCO 2 R 6 , NHCONHR 6 or NHSO 2 R 6 ; and with the further proviso that when X is combined with Y, then J represents CONHR 6 , SO 2 NHR 6 , CN, SO 2 R 6 or SCN; R 6 is a substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl group as defined for R 1 above; and Y is R 1 , acylamino or may be combined together with X as described above.

Claim 15

The process of claim 12 wherein in formula I, R 1 and R 2 are each C 2 H 5 , R 3 is hydrogen, and R 4 and R 5 are each C 6 H 5 ; and in formula II, J is CONHCH 3 , R 3 is CH 3 and X and Y are joined together to form a 6-membered aromatic ring.

Claim 16

The process of claim 12 wherein in formula I, R 1 and R 2 are each C 2 H 5 , R 3 is hydrogen, and R 4 and R 5 are each C 6 H 5 ; and in formula II, X is Cl, J is NHCOCH 2 OCH 3 , R 3 is CH 3 and Y is C 2 H 5 .

Claim 17

The process of claim 12 wherein in formula I, R 1 and R 2 are each C 2 H 5 , R 3 is CH 3 , R 4 is C 6 H 5 S and R 5 is C 6 H 5 ; and in formula II, J is CONHCH 3 , R 3 is CH 3 and X and Y are joined together to form a 6-membered aromatic ring.

Claim 18

The process of claim 12 wherein said dye-donor element contains an infrared-absorbing dye in said dye layer.

Claim 19

In a thermal dye transfer assemblage comprising: a) a cyan dye-donor element comprising a support having thereon a dye layer comprising a mixture of cyan dyes dispersed in a polymeric binder, and b) a dye-receiving element comprising a support having thereon a dye image-receiving layer, said dye-receiving element being in a superposed relationship with said cyan dye-donor element so that said dye layer is in contact with said dye image-receiving layer, the improvement wherein at least one of the cyan dyes has the formula: ##STR27## wherein: R 1 and R 2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 6 carbon atoms; a substituted or unsubstituted cycloalkyl group having from about 5 to about 7 carbon atoms; a substituted or unsubstituted allyl group; or a substituted or unsubstituted aryl or hetaryl group having from about 6 to about 10 carbon atoms; or R 1 and R 2 represent atoms which can be joined together to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring; or either or both of R 1 and R 2 together with one or two of R 3 represent atoms which can form a 5- to 7-membered heterocyclic ring; each R 3 independently represents substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl as described above for R 1 and R 2 ; alkoxy, aryloxy, halogen, nitro, cyano, thiocyano, hydroxy, acyloxy, acyl, alkoxycarbonyl, aminocarbonyl, alkoxycarbonyloxy, carbamoyloxy, acylamido, ureido, imido, alkylsulfonyl, arylsulfonyl, alkylsulfonamido, arylsulfonamido, alkylthio, arylthio or trifluoromethyl; or atoms at any two adjacent positions of R 3 may be combined together to form a 5-or 6-membered carbocyclic or heterocyclic ring; m is an integer of from 0 to 4; R 4 represents R 5 , alkylthio or arylthio, with the proviso that when R 4 is alkylthio or arylthio, then m must be at least 1; and R 5 represents a substituted or unsubstituted aryl or hetaryl group as described above for R 1 and R 2 ; and at least one of the other of the dyes having the formula: ##STR28## wherein: R 1 , R 2 , R 3 and m represent the same as above; X represents hydrogen, halogen or may be combined together with Y to represent the atoms necessary to complete a 6-membered aromatic ring, thus forming a fused bicyclic quinoneimine, such as a naphthoquinoneimine; with the proviso that when X is hydrogen, then J represents NHCOR F , where R F represents a perfluorinated alkyl or aryl group; and with the further proviso that when X is halogen, then J represents NHCOR 6 , NHCO 2 R 6 , NHCONHR 6 or NHSO 2 R 6 ; and with the further proviso that when X is combined with Y, then J represents CONHR 6 , SO 2 NHR 6 , CN, SO 2 R 6 or SCN; R 6 is a substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl group as defined for R 1 above; and Y is R 1 , acylamino or may be combined together with X as described above.

Claim 20

In a thermal dye transfer assemblage comprising: a) a cyan dye-donor element comprising a support having thereon a dye layer comprising a mixture of cyan dyes dispersed in a polymeric binder, and b) a dye-receiving element comprising a support having thereon a dye image-receiving layer, said dye-receiving element being in a superposed relationship with said cyan dye-donor element so that said dye layer is in contact with said dye image-receiving layer, the improvement wherein at least one of the cyan dyes has the formula: ##STR27## wherein: R 1 and R 2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 6 carbon atoms; a substituted or unsubstituted cycloalkyl group having from about 5 to about 7 carbon atoms; a substituted or unsubstituted allyl group; or a substituted or unsubstituted aryl or hetaryl group having from about 6 to about 10 carbon atoms; or R 1 and R 2 represent atoms which can be joined together to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring; or either or both of R 1 and R 2 together with one or two of R 3 represent atoms which can form a 5- to 7-membered heterocyclic ring; each R 3 independently represents substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl as described above for R 1 and R 2 ; alkoxy, aryloxy, halogen, nitro, cyano, thiocyano, hydroxy, acyloxy, acyl, alkoxycarbonyl, aminocarbonyl, alkoxycarbonyloxy, carbamoyloxy, acylamido, ureido, imido, alkylsulfonyl, arylsulfonyl, alkylsulfonamido, arylsulfonamido, alkylthio, arylthio or trifluoromethyl; or atoms at any two adjacent positions of R 3 may be combined together to form a 5-or 6-membered carbocyclic or heterocyclic ring; m is an integer of from 0 to 4; R 4 represents R 5 , alkylthio or arylthio, with the proviso that when R 4 is alkylthio or arylthio, then m must be at least 1; and R 5 represents a substituted or unsubstituted aryl or hetaryl group as described above for R 1 and R 2 ; and at least one of the other of the dyes having the formula: ##STR28## wherein: R 1 , R 2 , R 3 and m represent the same as above; X represents hydrogen, halogen or may be combined together with Y to represent the atoms necessary to complete a 6-membered aromatic ring, thus forming a fused bicyclic quinoneimine, such as a naphthoquinoneimine; with the proviso that when X is hydrogen, then J represents NHCOR F , where R F represents a perfluorinated alkyl or aryl group; and with the further proviso that when X is halogen, then J represents NHCOR 6 , NHCO 2 R 6 , NHCONHR 6 or NHSO 2 R 6 ; and with the further proviso that when X is combined with Y, then J represents CONHR 6 , SO 2 NHR 6 , CN, SO 2 R 6 or SCN; R 6 is a substituted or unsubstituted alkyl, cycloalkyl, allyl, aryl or hetaryl group as defined for R 1 above; and Y is R 1 , acylamino or may be combined together with X as described above.

Claim 21

The assemblage of claim 17 wherein in formula I, R 1 and R 2 are each C 2 H 5 , R 3 is hydrogen, and R 4 and R 5 are each C 6 H 5 ; and in formula II, J is CONHCH 3 , R 3 is CH 3 and X and Y are joined together to form a 6-membered aromatic ring.

Claim 22

The assemblage of claim 17 wherein in formula I, R 1 and R 2 are each C 2 H 5 , R 3 is hydrogen, and R 4 and R 5 are each C 6 H 5 ; and in formula II, X is Cl J is NHCOCH 2 OCH 3 , R 3 is CH 3 and Y is C 2 H 5 .

Claim 23

The assemblage of claim 17 wherein in formula I, R 1 and R 2 are each C 2 H 5 , R 3 is CH 3 , R 4 is C 6 H 5 S and R 5 is C 6 H 5 ; and in formula II, J is CONHCH 3 , R 3 is CH 3 and X and Y are joined together to form a 6-membered aromatic ring.