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US3974147A Expired / Lapsed US ⏱️ 0.0 years remaining

Reduced styryl dyes

Assignee: 3M Co
•
Filing: 1975-06-25
•
Granted: 1976-08-10
•
Expires: 1995-06-25
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Abstract

Abstract Dihydroheterocyclic amines having a N-hydrocarbyl substitution and a 2-(or 4-) (omega-(nuclearly substituted cyclic)) vinylenyl substitution are described. There compounds are oxidized in an acidic environment to produce styryl dyes.

Inventors

  • 👤 George V. D. Tiers
  • 👤 Joseph A. Wiese, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 08:15
CPC Classifications
G; G03; G03C; G03C1/00; G03C1/72; G03C1/73; G03C1/732; G03C1/675; G03C1/733; Y; Y10; Y10S; Y10S430/00; Y10S430/143

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 237 words
A N-hydrocarbyl substituted dihydroheterocyclic amine selected from the group consisting of D--(CH=CH).sub.n A and D--(CH=CH).sub.n CH=CAA' wherein n is an integer from 1-3 inclusive, D is: ##EQU1## A and A' are independently: ##SPC4## and A and A' when taken together with the carbon to which attached are: ##SPC5## R is hydrocarbyl; Q' is =CR'R', S, O, Se or =NR'; Q 2 is O, S, Se, =NH, or =NR; Z is hydrogen or taken together with an adjacent Z, the group of two may be either benzo- or naphtho- with or without an auxochromic substituent; Y is H, Cl, F, Br, alkyl of 1-6 carbon atoms, OH, OR 2 , SR 5 or NR 3 R 4; Z' is H, Cl, F, Br, alkyl of 1-6 carbon atoms, --OR 5 or --NR 2 5; Z" is H, Cl, F, Br, alkyl of 1-6 carbon atoms or --OR 5 ; or Z' and adjacent Z" taken together can be benzo- or naphto- with or without auxochromic substituents; R' is H, alkyl of 1-6 carbon atoms; phenyl or benzyl; R 2 is alkyl of 1-6 carbon atoms; R 5 is methyl or ethyl; R 3 and R 4 are independently hydrocarbyl or halohydrocarbyl or taken together with an adjacent Z" each can be independently 1,2-ethylene, 1,3-propylene or 1,2-phenylene or in conjunction with each other can form a 5-6 member ring including not more than 1 oxygen or one additional nitrogen.
Claim 2
Dependent Claim 237 words
A N-hydrocarbyl substituted dihydroheterocyclic amine selected from the group consisting of D--(CH=CH).sub.n A and D--(CH=CH).sub.n CH=CAA' wherein n is an integer from 1-3 inclusive, D is: ##EQU1## A and A' are independently: ##SPC4## and A and A' when taken together with the carbon to which attached are: ##SPC5## R is hydrocarbyl; Q' is =CR'R', S, O, Se or =NR'; Q 2 is O, S, Se, =NH, or =NR; Z is hydrogen or taken together with an adjacent Z, the group of two may be either benzo- or naphtho- with or without an auxochromic substituent; Y is H, Cl, F, Br, alkyl of 1-6 carbon atoms, OH, OR 2 , SR 5 or NR 3 R 4; Z' is H, Cl, F, Br, alkyl of 1-6 carbon atoms, --OR 5 or --NR 2 5; Z" is H, Cl, F, Br, alkyl of 1-6 carbon atoms or --OR 5 ; or Z' and adjacent Z" taken together can be benzo- or naphto- with or without auxochromic substituents; R' is H, alkyl of 1-6 carbon atoms; phenyl or benzyl; R 2 is alkyl of 1-6 carbon atoms; R 5 is methyl or ethyl; R 3 and R 4 are independently hydrocarbyl or halohydrocarbyl or taken together with an adjacent Z" each can be independently 1,2-ethylene, 1,3-propylene or 1,2-phenylene or in conjunction with each other can form a 5-6 member ring including not more than 1 oxygen or one additional nitrogen.
Claim 3
Dependent Claim 20 words
An N-hydrocarbyl-substituted dihydroheterocyclic amine according to claim 1 wherein R is alkyl of 1-6 carbon atoms and R' is methyl.
Claim 4
Dependent Claim 139 words
An N-hydrocarbyl-substituted dihydroheterocyclic amine according to claim 1 having the structure D--(CH=CH).sub. n --A wherein n is an integer from 1 to 3 inclusive, D is: ##STR3## A is: ##SPC6## R is alkyl of 1-6 carbon atoms Q' is CR'R', S, O, Se or NR' Y' is NR 6 R 7 , N-piperidino or N-morpholino Z is hydrogen or taken together with an adjacent Z, the group of two may be either benzo- or naphtho- with or without an auxochromic substituent; Z' is H, Cl, F, Br, alkyl 0f 1-6 carbon atoms, --OR 5 or --NR 2 5; Z" is H, Cl, F, Br, alkyl of 1-6 carbon atoms or --OR 5; Z' and adjacent Z" taken together can be benzo- or naphtho- with or without auxochromic substituents; R' is methyl R 6 and R 7 are independently hydrocarbyl.
Claim 5
Dependent Claim 50 words
An N-hydrocarbyl-substituted dihydroheterocyclic amine according to claim 1 having the structure D--(CH=CH).sub.n --CH=CAA' wherein D is: ##STR4## n is an integer from 1-3 inclusive; R is alkyl of 1-6 carbon atoms; Q' is CR'R', S, O, Se or NR'; R' is methyl; and A and A' are dimethylaminophenyl or halodimethylaminophenyl.
Claim 6
Dependent Claim 21 words
The N-hydrocarbyl-substituted dihydroheterocyclic amine according to claim 3 wherein D is 1,3,3-trimethylindolinyl, n is 1 and A is 2-chloro-4-dimethyl amino methylphenyl.
Claim 7
Dependent Claim 19 words
The N-hydrocarbyl-substituted dihydroheterocyclic amine according to claim 3 wherein D is 1,3,3-trimethylindolinyl, n is 1 and A is 2,4-dimethoxyphenyl.
Claim 8
Dependent Claim 19 words
The N-hydrocarbyl-substituted dihydroheterocyclic amine according to claim 3 wherein D is 5-chloro-1,3,3-trimethylindolinyl, n is 1 and A is 3-bromo-4-dimethylaminophenyl.
Claim 9
Dependent Claim 19 words
The N-hydrocarbyl-substituted heterocyclic amine according to claim 3 wherein D is 1,3,3-trimethylindolinyl, n is 1 and A is 4-dimethylaminophenyl.
Claim 10
Dependent Claim 19 words
The N-hydrocarbyl-substituted heterocyclic amine according to claim 3 wherein D is 3-ethyl-2,3-dihydro-2-benzothiazolyl, n is 1 and A is 4-dimethylamainophenyl.
Claim 11
Dependent Claim 21 words
The N-hydrocarbyl-substituted heterocycline amine according to claim 4 wherein D is 1,3,3-trimethylindolinyl, n is 1 and A and A' are 4-dimethylaminophenyl.
Claim 12
Dependent Claim 21 words
The N-hydrocarbyl-substituted heterocyclic amine according to claim 4 where D is 5-chloro-1,3,3-trimethylindolinyl, n is 1 and A and A' are 4-dimethylaminophenyl.
Claim 13
Dependent Claim 29 words
An N-hydrocarbyl-substituted dihydroheterocyclic amine according to claim 1 convertible from a colorless state to a colored state by exposure to an ionizing source in the presence of an anionogen.

References Cited (Backward Citations)

US3576801A Cited
US3796573A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-08-10 1980-02-09 1980-08-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-08-10 1984-02-09 1984-08-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-08-10 1988-02-09 1988-08-10 $7700.00 Window Closed / Lapsed

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