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US 4,539,579 AGranted
Compounds, processes and marking systems
AssigneeThe Hilton-Davis Chemical Co.
InventorsPaul J. Schmidt, William M. Hung
Life of this patent
Estimating the term…
Abstract
This invention relates to mono- and bis(aryl- and/or heteroaryl)-substituted-phthalazinones, phthalimidines, pyridopyridazinones and pyrrolopyridinones useful as color-forming substances, particularly in electrochromic recording systems, which are prepared by the interaction of a mono- or bis-substituted-phthalide or furopyridinone with a substituted or unsubstituted hydrazine.
Claims16
A substrate for use in electrochromic recording comprising a support sheet containing as a color-forming substance a 3-R.sup.1 -4-X-4-Y-R-phthalazin-1(2H)-one having the structural formula ##STR57## wherein:
- R represents hydrogen, dialkylamino in which alkyl is non-tertiary C.sub.1 to C.sub.4 alkyl, COOR.sup.2 in which R.sup.2 is hydrogen or non-tertiary C.sub.1 to C.sub.16 alkyl or one to four halo;
- R.sup.1 represents hydrogen, C.sub.1 to C.sub.3 alkyl, pyridyl, ##STR58## in which Z is non-tertiary C.sub.1 to C.sub.4 alkoxy, NHNH.sub.2, or non-tertiary C.sub.1 to C.sub.4 alkyl, phenyl or phenyl substituted by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy, halo, nitro or amino;
- X is selected from the group consisting of ##STR59## Y is selected from the group consisting of hydrogen, ##STR60## in which R.sup.3 and R.sup.9 independently represent hydrogen, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy, acylamido in which acyl is non-tertiary C.sub.2 to C.sub.4 alkyl or dialkylamino in which alkyl is non-tertiary C.sub.1 to C.sub.4 alkyl,
- R.sup.4 and R.sup.10 independently represent non-tertiary C.sub.1 to C.sub.4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.5 and R.sup.11 independently represent non-tertiary C.sub.1 to C.sub.4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.6 and R.sup.12 independently represent hydrogen, non-tertiary C.sub.1 to C.sub.16 alkyl, non-tertiary C.sub.2 to C.sub.8 alkylene, phenoxyethyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.7 and R.sup.13 independently represent hydrogen, C.sub.1 to C.sub.3 alkyl or phenyl, and
- R.sup.8 and R.sup.14 independently represent hydrogen, halo, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or nitro.
5 more elements
A substrate for use in electrochromic recording comprising a support sheet containing as color-forming substances an isomeric mixture of 7-R.sup.1 -8-X-8-Y-pyrido-[2,3d]-pyridazin-5(6H)-ones and 5-X-5-Y-6-R.sup.1 -pyrido-[2,3d]-pyridazin-8-(5H)-ones having the structural formulas ##STR66## wherein:
- R.sup.1 represents hydrogen, C.sub.1 to C.sub.3 alkyl, pyridyl, ##STR67## in which Z is non-tertiary C.sub.1 to C.sub.4 alkoxy, NHNH.sub.2, or non-tertiary C.sub.1 to C.sub.4 alkyl, phenyl or phenyl substituted by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy, halo, nitro or amino;
- X is selected from the group consisting of ##STR68## Y is selected from the group consisting of hydrogen, ##STR69## in which R.sup.3 and R.sup.9 independently represent hydrogen, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy, acylamido in which acyl is non-tertiary C.sub.2 to C.sub.4 alkyl or dialkylamino in which alkyl is non-tertiary C.sub.1 to C.sub.4 alkyl,
- R.sup.4 and R.sup.10 independently represent non-tertiary C.sub.1 to C.sub.4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.5 and R.sup.11 independently represent non-tertiary C.sub.1 to C.sub.4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.6 and R.sup.12 independently represent hydrogen, non-tertiary C.sub.1 to C.sub.16 alkyl, non-tertiary C.sub.2 to C.sub.8 alkylene, phenoxyethyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.7 and R.sup.13 independently represent hydrogen, C.sub.1 to C.sub.3 alkyl or phenyl, and
- R.sup.8 and R.sup.14 independently represent hydrogen, halo, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or nitro.
4 more elements
A substrate for use in electrochromic recording comprising a support sheet containing as a color-forming substance a 2-(N-R.sup.1 -amino)-3-X-3-Y-R-phthalimidine having the structural formula ##STR72## wherein:
- R represents hydrogen, dialkylamino in which alkyl is non-tertiary C.sub.1 to C.sub.4 alkyl, COOR.sup.2 in which R.sup.2 is hydrogen or non-tertiary C.sub.1 to C.sub.16 alkyl or one to four halo;
- R.sup.1 represents hydrogen, C.sub.1 to C.sub.3 alkyl, pyridyl, ##STR73## in which Z is non-tertiary C.sub.1 to C.sub.4 alkoxy, NHNH.sub.2, or non-tertiary C.sub.1 to C.sub.4 alkyl, phenyl or phenyl substituted by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy, halo, nitro or amino;
- X is selected from the group consisting of ##STR74## Y is selected from the group consisting of hydrogen, ##STR75## in which R.sup.3 selects hydrogen, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 C.sub.4 alkoxy, acylamido in which acyl is non-tertiary C.sub.2 to C.sub.4 alkyl or dialkylamino in which alkyl is non-tertiary C.sub.1 to C.sub.4 alkyl,
- R.sup.4 represents non-tertiary C.sub.1 to C.sub.4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.5 represents non-tertiary C.sub.1 to C.sub.4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.6 and R.sup.12 independently represent hydrogen, non-tertiary C.sub.1 to C.sub.16 alkyl, non-tertiary C.sub.2 to C.sub.8 alkylene, phenoxyethyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.7 and R.sup.13 independently represent hydrogen, C.sub.1 to C.sub.3 alkyl or phenyl, and
- R.sup.8 and R.sup.14 independently represent hydrogen, halo, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or nitro.
5 more elements
A substrate for use in electrochromic recording comprising a support sheet containing as color-forming substances an isomeric mixture of 6-(N-R.sup.1 -amino)-7-X-7-Y-(5H)-pyrrolo-[3,4-b]-pyridin-5-ones and 5-X-5-Y-6-(N-R.sup.1 -amino)-(7H)-pyrrolo-[3,4-b]-pyridin-7-ones having the structural formulas ##STR79## wherein:
- R represents hydrogen, dialkylamino in which alkyl is non-tertiary C.sub.1 to C.sub.4 alkyl, COOR.sup.2 in which R.sup.2 is hydrogen or non-tertiary C.sub.1 to C.sub.16 alkyl or one to four halo;
- R.sup.1 represents hydrogen, C.sub.1 to C.sub.3 alkyl, pyridyl, ##STR80## in which Z is non-tertiary C.sub.1 to C.sub.4 alkoxy, NHNH.sub.2, or non-tertiary C.sub.1 to C.sub.4 alkyl, phenyl or phenyl substituted by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy, halo, nitro or amino;
- X is selected from the group consisting of ##STR81## Y is selected from the group consisting of hydrogen, ##STR82## in which R.sup.3 and R.sup.9 independently represent hydrogen, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy, acylamido in which acyl is non-tertiary C.sub.2 to C.sub.4 alkyl or dialkylamino in which alkyl is non-tertiary C.sub.1 to C.sub.4 alkyl,
- R.sup.4 and R.sup.10 independently represent non-tertiary C.sub.1 to C.sub.4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.5 and R.sup.11 independently represent non-tertiary C.sub.1 to C.sub.4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.6 and R.sup.12 independently represent hydrogen, non-tertiary C.sub.1 to C.sub.16 alkyl, non-tertiary C.sub.2 to C.sub.8 alkylene, phenoxyethyl, benzyl or benzyl substituted in the benzene ring by one or two of halo or C.sub.1 to C.sub.3 alkyl,
- R.sup.7 and R.sup.13 independently represent hydrogen, C.sub.1 to C.sub.3 alkyl or phenyl, and
- R.sup.8 and R.sup.14 independently represent hydrogen, halo, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or nitro.
5 more elements
Dependencies are inferred from the claim text.