Mixture of dyes for black dye donor for thermal color proofing

Claim 2

A black dye-donor element for thermal dye transfer comprising a support having thereon a dye layer comprising a mixture of at least one cyan, magenta and yellow dyes dispersed in a polymeric binder, at least one of the cyan dyes having the formula: ##STR28## wherein: R 1 and R 2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having from about 5 to about 7 carbon atoms or a substituted or unsubstituted allyl group; with the proviso that R 1 and R 2 cannot both be hydrogen; or R 1 and R 2 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 can be combined with an R 3 to form a 5- to 7-membered heterocyclic ring; each R 3 independently represents substituted or unsubstituted alkyl, cycloalkyl or allyl as described above for R 1 and R 2 , alkoxy, aryloxy, halogen, thiocyano, acylamido, ureido, alkylsulfonamido, arylsulfonamido, alkylthio, arylthio or trifluoromethyl; or any two of R 3 may be combined together to form a 5- or 6-membered carbocyclic or heterocyclic ring; or one or two of R 3 may be combined with either or both of R 1 and R 2 to complete a 5- to 7-membered ring; m is an integer of from 0 to 4; R 4 represents hydrogen or an electron withdrawing group; R 5 represents an electron withdrawing group, a substituted or unsubstituted aryl group having from about 6 to about 10 carbon atoms or a substituted or unsubstituted hetaryl group having from about 5 to about 10 atoms; R 6 and R 7 each independently represents an electron withdrawing group; and R 6 and R 7 may be combined to form the residue of an active methylene compound; and at least one of the yellow dyes having the formula: ##STR29## wherein: R 8 represents the same groups as R 1 above; a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; a substituted or unsubstituted hetaryl group of from about 5 to about 10 atoms; R 9 and R 10 each independently represents hydrogen; R 8 ; cyano; acyloxy; alkoxy of 1 to about 6 carbon atoms; halogen; or alkoxycarbonyl; or any two of R 8 , R 9 and R 10 together represent the atoms necessary to complete a 5- to 7-membered ring; R 11 represents the same groups as R 8 ; G represents a substituted or unsubstituted alkyl, cycloalkyl or allyl group as described above for R 8 , NR 12 R 13 or OR 14 ; R 12 and R 13 each independently represents hydrogen, acyl or R 8 , with the proviso that R 12 and R 13 cannot both be hydrogen at the same time; or R 12 and R 13 together represent the atoms necessary to complete a 5- to 7-membered ring; R 14 represents alkyl, cycloalkyl or allyl groups as in R 1 above, or aryl or hetaryl as in R 8 above; X represents C(R 18 )(R 19 ), S, O or NR 18 ; R 18 and R 19 each independently represents the same groups as R 8 ; or R 18 and R 19 together represent the atoms necessary to complete a 5- to 7-membered ring; and Y represents the atoms necessary to complete a 5- or 6-membered ring which may be fused to another ring system; and at least one of the magenta dyes having the formula: ##STR30## wherein: R 15 is a substituted or unsubstituted alkyl or allyl group of from 1 to about 10 carbon atoms; Q is an alkoxy group of from 1 to about 4 carbon atoms or represents the atoms which when taken together with R 16 forms a 5- or 6-membered ring; R 16 is any of the groups for R 15 or represents the atoms which when taken together with Q forms a 5- or 6-membered ring; J is R 15 , an alkoxy group of from 1 to about 4 carbon atoms, hydrogen, halogen, or NHJ 1 R 21 ; R 21 is a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; J 1 is CO, CO 2 , --SO 2 -- or CONR 22 --; R 17 is a substituted or unsubstituted alkyl or allyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; R 20 is hydrogen, cyano, a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; and R 22 is hydrogen or R 17 .

Claim 3

The element of claim 1 wherein R 4 , R 6 and R 7 in formula I are cyano.

Claim 4

The element of claim 1 wherein R 1 in formula I is C 2 H 5 , C 2 H 4 OH, or n-C 3 H 7 .

Claim 5

The element of claim 1 wherein R 2 in formula I is C 2 H 5 or n-C 3 H 7 .

Claim 6

The element of claim 1 wherein R 3 in formula I is hydrogen, OC 2 H 5 , CH 3 or NHCOCH 3 .

Claim 7

The element of claim 1 wherein R 5 in formula I is p-C 6 H 4 Cl, m-C 6 H 4 NO 2 or naphthyl.

Claim 8

The element of claim 1 wherein G is N(CH 3 ) 2 or CH 3 .

Claim 9

The element of claim 1 wherein X is C(CH 3 ) 2 or O.

Claim 10

The element of claim 1 wherein R 8 is C 2 H 5 or CH 3 and R 11 is C 6 H 5 .

Claim 11

The element of claim 1 wherein R 9 and R 10 are each hydrogen.

Claim 12

The element of claim 1 wherein R 15 and R 16 are each ethyl, Q is OCH 3 , J 1 is CO, R 17 and R 21 are each CH 3 , and R 20 is C 4 H 9 -t.

Claim 13

The element of claim 1 wherein R 15 and R 16 are each ethyl, Q is OCH 3 , J 1 is CO, R 21 is CH 3 , R 17 is CH 2 C 6 H 5 , and R 20 is C 4 H 9 -t.

Claim 14

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

Claim 15

In a process of forming a dye transfer image comprising imagewise-heating a black dye-donor element comprising a support having thereon a dye layer comprising a mixture of at least one cyan, magenta and yellow dyes dispersed in a polymeric binder, at least one of the cyan dyes having the formula: ##STR31## wherein: R 1 and R 2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having from about 5 to about 7 carbon atoms or a substituted or unsubstituted allyl group; with the proviso that R 1 and R 2 cannot both be hydrogen; or R 1 and R 2 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 can be combined with an R 3 to form a 5- to 7-membered heterocyclic ring; each R 3 independently represents substituted or unsubstituted alkyl, cycloalkyl or allyl as described above for R 1 and R 2 , alkoxy, aryloxy, halogen, thiocyano, acylamido, ureido, alkylsulfonamido, arylsulfonamido, alkylthio, arylthio or trifluoromethyl; or any two of R 3 may be combined together to form a 5- or 6-membered carbocyclic or heterocyclic ring; or one or two of R 3 may be combined with either or both of R 1 and R 2 to complete a 5- to 7-membered ring; m is an integer of from 0 to 4; R 4 represents hydrogen or an electron withdrawing group; R 5 represents an electron withdrawing group, a substituted or unsubstituted aryl group having from about 6 to about 10 carbon atoms or a substituted or unsubstituted hetaryl group having from about 5 to about 10 atoms; R 6 and R 7 each independently represents an electron withdrawing group; and R 6 and R 7 may be combined to form the residue of an active methylene compound; and at least one of the yellow dyes having the formula: ##STR32## wherein: R 8 represents the same groups as R 1 above; a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; a substituted or unsubstituted hetaryl group of from about 5 to about 10 atoms; R 9 and R 10 each independently represents hydrogen; R 8 ; cyano; acyloxy; alkoxy of 1 to about 6 carbon atoms; halogen; or alkoxycarbonyl; or any two of R 8 , R 9 and R 10 together represent the atoms necessary to complete a 5- to 7-membered ring; R 11 represents the same groups as R 8 ; G represents a substituted or unsubstituted alkyl, cycloalkyl or allyl group as described above for R 8 , NR 12 R 13 or OR 14 ; R 12 and R 13 each independently represents hydrogen, acyl or R 8 , with the proviso that R 12 and R 13 cannot both be hydrogen at the same time; or R 12 and R 13 together represent the atoms necessary to complete a 5- to 7-membered ring; R 14 represents alkyl, cycloalkyl or allyl groups as in R 1 above, or aryl or hetaryl as in R 8 above; X represents C(R 18 )(R 19 ), S, O or NR 18 ; R 18 and R 19 each independently represents the same groups as R 8 ; or R 18 and R 19 together represent the atoms necessary to complete a 5- to 7-membered ring; and Y represents the atoms necessary to complete a 5- or 6-membered ring which may be fused to another ring system; and at least one of the magenta dyes having the formula ##STR33## wherein R 15 is a substituted or unsubstituted alkyl or allyl group of from 1 to about 10 carbon atoms; Q is an alkoxy group of from 1 to about 4 carbon atoms or represents the atoms which when taken together with R 16 forms a 5- or 6-membered ring; R 16 is any of the groups for R 15 or represents the atoms which when taken together with Q forms a 5- or 6-membered ring; J is R 15 , an alkoxy group of from 1 to about 4 carbon atoms, hydrogen, halogen, or NHJ 1 R 21 ; R 21 is a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; J 1 is CO, CO 2 , --SO 2 -- or CONR 22 --; R 17 is a substituted or unsubstituted alkyl or allyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; R 20 is hydrogen, cyano, a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; and R 22 is hydrogen or R 17 .

Claim 16

In a process of forming a dye transfer image comprising imagewise-heating a black dye-donor element comprising a support having thereon a dye layer comprising a mixture of at least one cyan, magenta and yellow dyes dispersed in a polymeric binder, at least one of the cyan dyes having the formula: ##STR31## wherein: R 1 and R 2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having from about 5 to about 7 carbon atoms or a substituted or unsubstituted allyl group; with the proviso that R 1 and R 2 cannot both be hydrogen; or R 1 and R 2 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 can be combined with an R 3 to form a 5- to 7-membered heterocyclic ring; each R 3 independently represents substituted or unsubstituted alkyl, cycloalkyl or allyl as described above for R 1 and R 2 , alkoxy, aryloxy, halogen, thiocyano, acylamido, ureido, alkylsulfonamido, arylsulfonamido, alkylthio, arylthio or trifluoromethyl; or any two of R 3 may be combined together to form a 5- or 6-membered carbocyclic or heterocyclic ring; or one or two of R 3 may be combined with either or both of R 1 and R 2 to complete a 5- to 7-membered ring; m is an integer of from 0 to 4; R 4 represents hydrogen or an electron withdrawing group; R 5 represents an electron withdrawing group, a substituted or unsubstituted aryl group having from about 6 to about 10 carbon atoms or a substituted or unsubstituted hetaryl group having from about 5 to about 10 atoms; R 6 and R 7 each independently represents an electron withdrawing group; and R 6 and R 7 may be combined to form the residue of an active methylene compound; and at least one of the yellow dyes having the formula: ##STR32## wherein: R 8 represents the same groups as R 1 above; a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; a substituted or unsubstituted hetaryl group of from about 5 to about 10 atoms; R 9 and R 10 each independently represents hydrogen; R 8 ; cyano; acyloxy; alkoxy of 1 to about 6 carbon atoms; halogen; or alkoxycarbonyl; or any two of R 8 , R 9 and R 10 together represent the atoms necessary to complete a 5- to 7-membered ring; R 11 represents the same groups as R 8 ; G represents a substituted or unsubstituted alkyl, cycloalkyl or allyl group as described above for R 8 , NR 12 R 13 or OR 14 ; R 12 and R 13 each independently represents hydrogen, acyl or R 8 , with the proviso that R 12 and R 13 cannot both be hydrogen at the same time; or R 12 and R 13 together represent the atoms necessary to complete a 5- to 7-membered ring; R 14 represents alkyl, cycloalkyl or allyl groups as in R 1 above, or aryl or hetaryl as in R 8 above; X represents C(R 18 )(R 19 ), S, O or NR 18 ; R 18 and R 19 each independently represents the same groups as R 8 ; or R 18 and R 19 together represent the atoms necessary to complete a 5- to 7-membered ring; and Y represents the atoms necessary to complete a 5- or 6-membered ring which may be fused to another ring system; and at least one of the magenta dyes having the formula ##STR33## wherein R 15 is a substituted or unsubstituted alkyl or allyl group of from 1 to about 10 carbon atoms; Q is an alkoxy group of from 1 to about 4 carbon atoms or represents the atoms which when taken together with R 16 forms a 5- or 6-membered ring; R 16 is any of the groups for R 15 or represents the atoms which when taken together with Q forms a 5- or 6-membered ring; J is R 15 , an alkoxy group of from 1 to about 4 carbon atoms, hydrogen, halogen, or NHJ 1 R 21 ; R 21 is a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; J 1 is CO, CO 2 , --SO 2 -- or CONR 22 --; R 17 is a substituted or unsubstituted alkyl or allyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; R 20 is hydrogen, cyano, a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; and R 22 is hydrogen or R 17 .

Claim 17

The process of claim 14 wherein said dye-donor element contains an infrared-absorbing dye in said dye layer.

Claim 18

In a thermal dye transfer assemblage comprising: a) a black dye-donor element comprising a support having thereon a dye layer comprising a mixture of cyan, yellow and magenta 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 black 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: ##STR34## wherein: R 1 and R 2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having from about 5 to about 7 carbon atoms or a substituted or unsubstituted allyl group; with the proviso that R 1 and R 2 cannot both be hydrogen; or R 1 and R 2 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 can be combined with an R 3 to form a 5- to 7-membered heterocyclic ring; each R 3 independently represents substituted or unsubstituted alkyl, cycloalkyl or allyl as described above for R 1 and R 2 , alkoxy, aryloxy, halogen, thiocyano, acylamido, ureido, alkylsulfonamido, arylsulfonamido, alkylthio, arylthio or trifluoromethyl; or any two of R 3 may be combined together to form a 5- or 6-membered carbocyclic or heterocyclic ring; or one or two of R 3 may be combined with either or both of R 1 and R 2 to complete a 5- to 7-membered ring; m is an integer of from 0 to 4; R 4 represents hydrogen or an electron withdrawing group; R 5 represents an electron withdrawing group, a substituted or unsubstituted aryl group having from about 6 to about 10 carbon atoms or a substituted or unsubstituted hetaryl group having from about 5 to about 10 atoms; R 6 and R 7 each independently represents an electron withdrawing group; and R 6 and R 7 may be combined to form the residue of an active methylene compound; and at least one of the yellow dyes having the formula ##STR35## wherein: R 8 represents the same groups as R 1 above; a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; a substituted or unsubstituted hetaryl group of from about 5 to about 10 atoms; R 9 and R 10 each independently represents hydrogen; R 8 ; cyano; acyloxy; alkoxy of 1 to about 6 carbon atoms; halogen; or alkoxycarbonyl; or any two of R 8 , R 9 and R 10 together represent the atoms necessary to complete a 5- to 7-membered ring; R 11 represents the same groups as R 8 ; G represents a substituted or unsubstituted alkyl, cycloalkyl or allyl group as described above for R 8 , NR 12 R 13 or OR 14 ; R 12 and R 13 each independently represents hydrogen, acyl or R 8 , with the proviso that R 12 and R 13 cannot both be hydrogen at the same time; or R 12 and R 13 together represent the atoms necessary to complete a 5- to 7-membered ring; R 14 represents alkyl, cycloalkyl or allyl groups as in R 1 above, or aryl or hetaryl as in R 8 above; X represents C(R 18 )(R 19 ), S, O or NR 18 ; R 18 and R 19 each independently represents the same groups as R 8 ; or R 18 and R 19 together represent the atoms necessary to complete a 5- to 7-membered ring; and Y represents the atoms necessary to complete a 5- or 6-membered ring which may be fused to another ring system; and at least one of the magenta dyes having the formula: ##STR36## wherein: R 15 is a substituted or unsubstituted alkyl or allyl group of from 1 to about 10 carbon atoms; Q is an alkoxy group of from 1 to about 4 carbon atoms or represents the atoms which when taken together with R 16 forms a 5- or 6-membered ring; R 16 is any of the groups for R 15 or represents the atoms which when taken together with Q forms a 5- or 6-membered ring; J is R 15 , an alkoxy group of from 1 to about 4 carbon atoms, hydrogen, halogen, or NHJ 1 R 21 ; R 21 is a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; J 1 is CO, CO 2 , --SO 2 -- or CONR 22 --; R 17 is a substituted or unsubstituted alkyl or allyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; R 20 is hydrogen, cyano, a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; and R 22 is hydrogen or R 17 .

Claim 19

In a thermal dye transfer assemblage comprising: a) a black dye-donor element comprising a support having thereon a dye layer comprising a mixture of cyan, yellow and magenta 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 black 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: ##STR34## wherein: R 1 and R 2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having from about 5 to about 7 carbon atoms or a substituted or unsubstituted allyl group; with the proviso that R 1 and R 2 cannot both be hydrogen; or R 1 and R 2 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 can be combined with an R 3 to form a 5- to 7-membered heterocyclic ring; each R 3 independently represents substituted or unsubstituted alkyl, cycloalkyl or allyl as described above for R 1 and R 2 , alkoxy, aryloxy, halogen, thiocyano, acylamido, ureido, alkylsulfonamido, arylsulfonamido, alkylthio, arylthio or trifluoromethyl; or any two of R 3 may be combined together to form a 5- or 6-membered carbocyclic or heterocyclic ring; or one or two of R 3 may be combined with either or both of R 1 and R 2 to complete a 5- to 7-membered ring; m is an integer of from 0 to 4; R 4 represents hydrogen or an electron withdrawing group; R 5 represents an electron withdrawing group, a substituted or unsubstituted aryl group having from about 6 to about 10 carbon atoms or a substituted or unsubstituted hetaryl group having from about 5 to about 10 atoms; R 6 and R 7 each independently represents an electron withdrawing group; and R 6 and R 7 may be combined to form the residue of an active methylene compound; and at least one of the yellow dyes having the formula ##STR35## wherein: R 8 represents the same groups as R 1 above; a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; a substituted or unsubstituted hetaryl group of from about 5 to about 10 atoms; R 9 and R 10 each independently represents hydrogen; R 8 ; cyano; acyloxy; alkoxy of 1 to about 6 carbon atoms; halogen; or alkoxycarbonyl; or any two of R 8 , R 9 and R 10 together represent the atoms necessary to complete a 5- to 7-membered ring; R 11 represents the same groups as R 8 ; G represents a substituted or unsubstituted alkyl, cycloalkyl or allyl group as described above for R 8 , NR 12 R 13 or OR 14 ; R 12 and R 13 each independently represents hydrogen, acyl or R 8 , with the proviso that R 12 and R 13 cannot both be hydrogen at the same time; or R 12 and R 13 together represent the atoms necessary to complete a 5- to 7-membered ring; R 14 represents alkyl, cycloalkyl or allyl groups as in R 1 above, or aryl or hetaryl as in R 8 above; X represents C(R 18 )(R 19 ), S, O or NR 18 ; R 18 and R 19 each independently represents the same groups as R 8 ; or R 18 and R 19 together represent the atoms necessary to complete a 5- to 7-membered ring; and Y represents the atoms necessary to complete a 5- or 6-membered ring which may be fused to another ring system; and at least one of the magenta dyes having the formula: ##STR36## wherein: R 15 is a substituted or unsubstituted alkyl or allyl group of from 1 to about 10 carbon atoms; Q is an alkoxy group of from 1 to about 4 carbon atoms or represents the atoms which when taken together with R 16 forms a 5- or 6-membered ring; R 16 is any of the groups for R 15 or represents the atoms which when taken together with Q forms a 5- or 6-membered ring; J is R 15 , an alkoxy group of from 1 to about 4 carbon atoms, hydrogen, halogen, or NHJ 1 R 21 ; R 21 is a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; J 1 is CO, CO 2 , --SO 2 -- or CONR 22 --; R 17 is a substituted or unsubstituted alkyl or allyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; R 20 is hydrogen, cyano, a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from about 6 to about 10 carbon atoms; and R 22 is hydrogen or R 17 .

Claim 20

The assemblage of claim 16 wherein said dye-donor element contains an infrared-absorbing dye in said dye layer.