Electrochromic marking systems
First Claim
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1. A substrate for use in electrochromic recording comprising a support sheet containing as a color-forming substance a 1/2-R-3-[N(R1 -CO)-N-R2 -amino]-7-[N-(R3)(R4)-amino]-8/9-R5 -10-(R1 -CO)-phenothiazine having the formula ##STR12## wherein:
- R and R5 independently represent hydrogen, non-tertiary C1 to C4 alkyl, non-tertiary C1 to C4 alkoxy, halogen or nitro;
R1 represents hydrogen, non-tertiary C1 to C12 alkyl, C4 to C8 cycloalkyl, non-tertiary C1 to C4 alkoxy or non-tertiary C1 to C4 alkoxycarbonyl, phenyl, phenyl substituted by one to three of non-tertiary C1 to C4 alkyl, non-tertiary C1 to C4 alkoxy, nitro, halo, phenyl, cyano, or trihalomethyl;
R2 represents C1 to C4 alkyl, phenyl, phenyl substituted by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy, benzyl or benzyl substituted in the benzene ring by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy; and
R3 and R4 independently represent C1 to C4 alkyl, phenyl, phenyl substituted by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy, benzyl or benzyl substituted in the benzene ring by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy.
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Abstract
3-(N-R2 -N-Acylamino)-7-(N-R3 -N-R4 -amino)-10-acylphenothiazines and phenoxazines useful as color formers, particularly in electrochromic recording systems, are prepared by the interaction of the corresponding 3-(N-R2 -amino)-7-(N-R3 -N-R4 -amino)phenothiazinium or phenoxazinium halide with a reducing agent to obtain the corresponding leuco compound and subsequently interacting the leuco compound with at least two molecular proportions of an acylating agent.
25 Citations
8 Claims
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1. A substrate for use in electrochromic recording comprising a support sheet containing as a color-forming substance a 1/2-R-3-[N(R1 -CO)-N-R2 -amino]-7-[N-(R3)(R4)-amino]-8/9-R5 -10-(R1 -CO)-phenothiazine having the formula ##STR12## wherein:
- R and R5 independently represent hydrogen, non-tertiary C1 to C4 alkyl, non-tertiary C1 to C4 alkoxy, halogen or nitro;
R1 represents hydrogen, non-tertiary C1 to C12 alkyl, C4 to C8 cycloalkyl, non-tertiary C1 to C4 alkoxy or non-tertiary C1 to C4 alkoxycarbonyl, phenyl, phenyl substituted by one to three of non-tertiary C1 to C4 alkyl, non-tertiary C1 to C4 alkoxy, nitro, halo, phenyl, cyano, or trihalomethyl; R2 represents C1 to C4 alkyl, phenyl, phenyl substituted by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy, benzyl or benzyl substituted in the benzene ring by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy; and R3 and R4 independently represent C1 to C4 alkyl, phenyl, phenyl substituted by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy, benzyl or benzyl substituted in the benzene ring by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy. - View Dependent Claims (2, 3, 4, 5, 6, 7)
- R and R5 independently represent hydrogen, non-tertiary C1 to C4 alkyl, non-tertiary C1 to C4 alkoxy, halogen or nitro;
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8. A substrate for use in electrochromic recording comprising a support sheet containing as a color-forming substance a 1/2-R-3-[N-(R1 -CO)-N-R2 -amino]-7-[N-(R3)(R4)-amino]-8/9-R5 -10-(R1 -CO)-phenoxazine having the formula ##STR13## wherein:
- R and R5 independently represent hydrogen, non-tertiary C1 to C4 alkyl, non-tertiary C1 to C4 alkoxy, halogen or nitro;
R1 represents hydrogen, non-tertiary C1 to C12 alkyl, C4 to C8 cycloalkyl, non-tertiary C1 to C4 alkoxy or non-tertiary C1 to C4 alkoxycarbonyl, phenyl, phenyl substituted by one to three of non-tertiary C1 to C4 alkyl, non-tertiary C1 to C4 alkoxy, nitro, halo, phenyl, cyano, or trihalomethyl; R2 represents C1 to C4 alkyl, phenyl, phenyl substituted by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy, benzyl or benzyl substituted in the benzene ring by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy; and R3 and R4 independently represent C1 to C4 alkyl, phenyl, phenyl substituted by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy, benzyl or benzyl substituted in the benzene ring by one or two of halo, nitro, non-tertiary C1 to C4 alkyl or non-tertiary C1 to C4 alkoxy.
- R and R5 independently represent hydrogen, non-tertiary C1 to C4 alkyl, non-tertiary C1 to C4 alkoxy, halogen or nitro;
Specification
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Current AssigneePMD Holdings Corporation
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Original AssigneeThe Hilton-Davis Chemical Company
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InventorsHung, William M., Gunn, Michael B.
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Primary Examiner(s)Hess, Bruce H.
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Application NumberUS06/636,460Time in Patent Office511 DaysField of Search346/217, 346/218, 427/150, 427/151, 204/2, 544/3US Class Current503/218CPC Class CodesB41M 5/20 using electric current B41M...C07D 265/38 [b, e]-condensed with two s...C07D 279/30 with acyl radicals attached...
