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US3853807A Expired / Lapsed US ⏱️ 0.0 years remaining

Heat resistant dyes for polyester film products

Assignee: Individual
•
Filing: 1973-04-09
•
Granted: 1974-12-10
•
Expires: 1993-04-09
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Abstract

Abstract Certain azabenzanthrone and diazabenzanthrone dyes have been found A. TO BE PECULIARLY RESISTANT TO SPONTANEOUS HIGH TEMPERATURE DEGRADATION, AND B. TO BE PARTICULARLY USEFUL AS COLORANTS FOR PHOTOGRAPHIC FILM PRODUCTS MADE BY EXTRUDING A DYED POLYESTER FILM BASE. In combination with a green dye such as 1,4-dihydroxy-5,8-di-ptoluidino anthraquinone or 1,4-di-p-butyl anilino-5,8-dihydroxy anthraquinone, which has the ability to inhibit or minimize edge fog in light sensitive film products having a polyester substrate, the red azabenzanthrone or diazabenzanthrone dye is particularly useful in the form of an approximately ''''neutral'''' colored film substrate.

Inventors

  • 👤 C Hunter

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 13:57
CPC Classifications
G; G03; G03C; G03C1/00; G03C1/76; G03C1/825; G03C1/83; C; C08; C08K; C08K5/00; C08K5/0008; C08K5/0041; C09; C09B; C09B5/00; C09B5/02; C09B5/14; C09B5/16; G03C1/795; G03C1/7954

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 53 words
A COLORED POLYESTER FILM ARTICLE HAVING A THICKNESS OF FROM ABOUT 0.5 TO ABOUT 30 MILS, AN OPTICAL DENSITY OF AT MOST ABOUT 0.5, AND A UNIFORM, APPROXIMATELY NEUTRAL COLOR; SAID FILM ARTICLE CONTAINING A BLEND OF DYES, WHICH BLEND CONSISTS ESSENTIALLY OF THE RED DYE 2,3-DIHYDRO-3-METHYL-2-OXO-6-PTOLUIDINO-3-AZABENZANTHRONE AND THE GREEN DYE 1,4DIHYDROXY-5,8-DI-P-TOLUIDINO ANTHRAQUINONE.
Claim 2
Dependent Claim 53 words
A COLORED POLYESTER FILM ARTICLE HAVING A THICKNESS OF FROM ABOUT 0.5 TO ABOUT 30 MILS, AN OPTICAL DENSITY OF AT MOST ABOUT 0.5, AND A UNIFORM, APPROXIMATELY NEUTRAL COLOR; SAID FILM ARTICLE CONTAINING A BLEND OF DYES, WHICH BLEND CONSISTS ESSENTIALLY OF THE RED DYE 2,3-DIHYDRO-3-METHYL-2-OXO-6-PTOLUIDINO-3-AZABENZANTHRONE AND THE GREEN DYE 1,4DIHYDROXY-5,8-DI-P-TOLUIDINO ANTHRAQUINONE.
Claim 3
Dependent Claim 14 words
A article as in claim 1, wherein said polyester consists essentially of poly(ethylene terephthalate).
Claim 4
Dependent Claim 14 words
An article as in claim 1, wherein said polyester consists essentially of poly(1,4-di-methylenecyclohexylene terephthalate).
Claim 5
Dependent Claim 24 words
A colored polyester article, comprising a blend of (1) at least one azabenzanthrone or diazabenzanthrone dye selected from the group of dyes having structures:
Claim 6
Dependent Claim 24 words
A colored polyester article, comprising a blend of (1) at least one azabenzanthrone or diazabenzanthrone dye selected from the group of dyes having structures:
Claim 7
Dependent Claim 18 words
An article as in claim 4, wherein said green dye is 1,4-dihydroxy-5,8-di-p-toluidino anthraquinone and said diazabenzanthrone dye is
Claim 8
Dependent Claim 16 words
An article as in claim 5, wherein said diazabenzanthrone dye is 6-amino-4-p-toluidino-1,3-diazabenzanthrone, 4-p-chloroanilino-1,3-diazabenzanthrone, or 4-anilino 6-(N-(2,4-dichlorobenzoyl)amino)-1,3-diazabenzanthrone.
Claim 9
Dependent Claim 18 words
An article as in claim 4, wherein said green dye is 1,4-dihydroxy-5,8-di-p-toluidino anthraquinone and said azabenzanthrone dye is
Claim 10
Dependent Claim 37 words
An article as in claim 7, wherein said green dye is 1,4-dihydroxy-5,8-di-p-toluidino anthraquinone and said azabenzanthrone dye is 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-p-toluenesulfonamido-3 -azabenzanthrone, 2,3-dihydro-3-methyl-2-oxo-1-p-toluidino-3-azabencanthrone, 2,3-dihydro-6-(N-3-(dimethylamino)-propylamino)-3-methyl-2-oxo-1 phenyl-3-azabenzanthrone, 2,3-dihydro-3-methyl-6-(p-(1-methyl-butyl)anilino)-2-oxo-1-phenyl-3 -azabenzanthrone, 2,3-dihydro-6-(2,4-dimethyl-anilino)-1-ethoxycarbonyl-3-methyl-2-oxo-3 -azabenzanthrone, 2,3-dihydro-6-p-chloroanilino-1-cyano-3-methyl-2-oxo-3-azabenzanthrone, 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-p-toluidino-3-azabenzanthrone, 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-m-toluidino-3-azabenzanthrone, 2, 3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-o-toluidino-3-azabenzanthrone, 2,3-dihydro-3-methyl-2-oxo-6-p-toluidino-3-azabenzanthrone, 2,3-dihydro-6-(4''t-amylanilino)-1-ethoxycarbonyl-3-methyl-2-oxo-3 -azabenzanthrone, or 2,3-dihydro-3-methyl-6-(2,4-dimethylanilino)-1-phenyl-3-azabenzanthrone.
Claim 11
Dependent Claim 19 words
An article as in claim 4, wherein said green dye is 1,4-di-butyl anilino-5,8-dihydroxy anthraquinone and said diazabenzanthrone dye is
Claim 12
Dependent Claim 16 words
An article as in claim 9 wherein said diazabenzanthrone dye is 6-amino-4-p-toluidino-1,3-diazabenzanthrone, 4-p-chloroanilino-1,3-diazabenzanthrone or 4-anilino-6-(N-(2,4-dichlorobenzoyl) amino)-1,3-diazabenzanthrone.
Claim 13
Dependent Claim 34 words
An article as in claim 4, wherein said polyester is a linear polyester of repeating polymethylene glycol and diacyl radicals, the number of carbon atoms in the polymethylene groups being from 2 to 8.
Claim 14
Dependent Claim 12 words
An article as in claim 4, wherein said polyester is poly(ethylene terephthalate).
Claim 15
Dependent Claim 13 words
An article as in claim 4, wherein said polyester is poly(1, 4-dimethylenecyclohexylene terephthalate).
Claim 16
Dependent Claim 7 words
A fiber article according to claim 4.
Claim 17
Dependent Claim 7 words
A molded article according to claim 4.
Claim 18
Dependent Claim 22 words
A colored polyester article having an approximately neutral color; said article comprising the red dye 2,3-dihydro-3-methyl-2-oxo-6-p-toluidino-3-azabenzanthrone and the green dye 1,4-dihydroxy-5,8-di-p-toluidino anthraquinone.
Claim 19
Dependent Claim 22 words
A colored polyester article having an approximately neutral color; said article comprising the red dye 2,3-dihydro-3-methyl-2-oxo-6-p-toluidino-3-azabenzanthrone and the green dye 1,4-dihydroxy-5,8-di-p-toluidino anthraquinone.
Claim 20
Dependent Claim 37 words
An article according to claim 16 containing from about 40 to about 600 parts of said red dye and from about 60 to about 1,000 parts of said green dYe per million parts of said colored polyester.
Claim 21
Dependent Claim 114 words
A film article comprising a colored polyester film substrate; said substrate comprising at least two different types of dyes selected from (a) the following group A azabenzanthrone dyes or group B diazabenzanthrone dyes: A. 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-toluenesulfonamido-3 -azabenzanthrone, 2,3-dihydro-3-methyl-2-oxo-1-p-toluidino-3-azabenzanthrone, 2,3-dihydro-6-(N-3-(dimethylamino)-propylamino)-3-methyl-2-oxo-1-phenyl-3 -azabenzanthrone, 2,3-dihydro-3-methyl-6-(p-(1-methylbutyl)anilino)-2-oxo-1-phenyl-3 -azabenzanthrone, 2,3-dihydro-6-(2,4-dimethyl-anilino)-1-ethoxycarbonyl-3-methyl-2-oxo-3 -azabenzanthrone, 2,3-dihydro-6-p-chloroanilino-1-cyano-3-methyl-2-oxo-3-azabenzanthrone, 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-p-toluidino-3-azabenzanthrone, 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-m-toluidino-3-azabenzanthrone, 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-o-toluidino-3-azabenzanthrone, 2,3-dihydro-3-methyl-2-oxo-6-p-toluidino-3-azabesnzanthrone, 2,3-dihydro-6-(4''-t-amylanilino)-1-ethoxycarbonyl-3-methyl-2-oxo-3 -azabenzanthrone or 2,3-dihydro-3-methyl-6-(2,4-dimethylanilino)-1-phenyl-3-azabenzanthrone, or B 6-amino-4-p-toluidino-1,3-diazabenzanthrone, 4-p-chloroanilino-1,3-diazabenzanthrone, or 4-anilino-6-(N-(2,4-dichlorobenzoyl)amino)-1,3-diazabenzanthrone, and at least one green dye selected from the group consisting of 1, 4-dihydroxy-5,8-di-p-toluidino anthraquinone and 1,4-di-p-butyl anilino-5,8-dihydroxy anthraquinone, said green dye being 1,4-dihydroxy-5,8-di-p-toluidino anthraquinone when said azabenzanthrone or diazabenzanthrone dye is selected from group (A) or (B), when said green dye is 1,4-di-p-butyl anilino-5,8-dihydroxy anthraquinone, said azabenzanthrone or diazabenzanthrone dye is selected from group (B).
Claim 22
Dependent Claim 114 words
A film article comprising a colored polyester film substrate; said substrate comprising at least two different types of dyes selected from (a) the following group A azabenzanthrone dyes or group B diazabenzanthrone dyes: A. 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-toluenesulfonamido-3 -azabenzanthrone, 2,3-dihydro-3-methyl-2-oxo-1-p-toluidino-3-azabenzanthrone, 2,3-dihydro-6-(N-3-(dimethylamino)-propylamino)-3-methyl-2-oxo-1-phenyl-3 -azabenzanthrone, 2,3-dihydro-3-methyl-6-(p-(1-methylbutyl)anilino)-2-oxo-1-phenyl-3 -azabenzanthrone, 2,3-dihydro-6-(2,4-dimethyl-anilino)-1-ethoxycarbonyl-3-methyl-2-oxo-3 -azabenzanthrone, 2,3-dihydro-6-p-chloroanilino-1-cyano-3-methyl-2-oxo-3-azabenzanthrone, 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-p-toluidino-3-azabenzanthrone, 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-m-toluidino-3-azabenzanthrone, 2,3-dihydro-1-ethoxycarbonyl-3-methyl-2-oxo-6-o-toluidino-3-azabenzanthrone, 2,3-dihydro-3-methyl-2-oxo-6-p-toluidino-3-azabesnzanthrone, 2,3-dihydro-6-(4''-t-amylanilino)-1-ethoxycarbonyl-3-methyl-2-oxo-3 -azabenzanthrone or 2,3-dihydro-3-methyl-6-(2,4-dimethylanilino)-1-phenyl-3-azabenzanthrone, or B 6-amino-4-p-toluidino-1,3-diazabenzanthrone, 4-p-chloroanilino-1,3-diazabenzanthrone, or 4-anilino-6-(N-(2,4-dichlorobenzoyl)amino)-1,3-diazabenzanthrone, and at least one green dye selected from the group consisting of 1, 4-dihydroxy-5,8-di-p-toluidino anthraquinone and 1,4-di-p-butyl anilino-5,8-dihydroxy anthraquinone, said green dye being 1,4-dihydroxy-5,8-di-p-toluidino anthraquinone when said azabenzanthrone or diazabenzanthrone dye is selected from group (A) or (B), when said green dye is 1,4-di-p-butyl anilino-5,8-dihydroxy anthraquinone, said azabenzanthrone or diazabenzanthrone dye is selected from group (B).

References Cited (Backward Citations)

US3728124A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1977-12-09 1978-06-10 1978-12-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1981-12-09 1982-06-10 1982-12-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1985-12-09 1986-06-10 1986-12-10 $7700.00 Window Closed / Lapsed

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