US4056560A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N,N'-bis(3,4-dicyanophenyl) alkanediamides
Assignee: United States Department of the Navy
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Filing: 1976-07-23
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Granted: 1977-11-01
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Expires: 1996-07-23
Abstract
Abstract N,N'-bis(3,4-dicyanophenyl) alkanediamides of the general formula: <IMAGE> wherein R = (CH2)n-2 and (CH2)xCH(CH3)(CH2)y; n = 3 to 20; x = 1 to 8; and y = 1 to 8, prepared by reacting 4-aminophthalonitrile with a saturated aliphatic dicarboxylic acid halide. These dinitriles readily polymerize through heating by themselves or with a metal or with a salt to form polyphthalocyanine resins, of the infinite molecular weight type which are useful as coatings, laminates, adhesives, filament windings, and castings. The general formulas for these polyphthalocyanine resins are: <IMAGE> <IMAGE> wherein R = (CH2)n-2 and (CH2)xCH(CH3)(CH2)y; n = 3 to 20; x = 1 to 8; and y = 1 to 8.
Inventors
- 👤 James R. Griffith
- 👤 Jacques G. O'Rear
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 21:36
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/0666; C08G73/0672
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
42 words
A composition of matter having the formula: ##STR10## wherein R = (CH 2 ) n-2 and (CH 2 ) x CHCH 3 (CH 2 ) y ; n = 3 to 20; x = 1 to 8; y = 1 to 8.
Claim 2
Dependent Claim
42 words
A composition of matter having the formula: ##STR10## wherein R = (CH 2 ) n-2 and (CH 2 ) x CHCH 3 (CH 2 ) y ; n = 3 to 20; x = 1 to 8; y = 1 to 8.
Claim 3
Dependent Claim
13 words
The composition of claim 1 wherein R = (CH 2 ) n-2 .
Claim 4
Dependent Claim
12 words
The composition of claim 2 wherein n = 4-10, 12-14, or 18.
Claim 5
Dependent Claim
13 words
The composition of claim 2 wherein n = 7, 9, 10-14, or 18.
Claim 6
Dependent Claim
17 words
The composition of claim 1 wherein R = CH 2 CH(CH 3 )CH 2 CH 2 .
Claim 7
Dependent Claim
175 words
A method of preparing the composition of claim 1, which comprises: a. adding 4-nitrophthalimide to ammonium hydroxide under agitation at room temperature in an imide-to-NH 3 OH mole ratio of at least 25:1; b. heating to a temperature from about 40° C to about 45° C until frothing ceases, thereby forming 4-nitrophthalimide; c. suspending 4-nitrophthalimide in pyridine; d. agitating 4-nitrophthalimide in pyridine; e. adding phosphorus oxychloride to the 4-nitrophthalamide suspended in pyridine in a POCl 3 -to-amide ratio from about 2.2:1 to about 2.3:1 at a rate such that the temperature ranges from about 65° to about 70° C, thereby forming 4-nitrophthalonitrile; f. reacting 4-nitrophthalonitrile with sodium dithionite to form 4-aminophthalonitrile; g. reacting a carbon tetrachloride solution of a saturated aliphatic acid halide of the general formula: ##STR11## wherein X is a halide, R is (CH 2 ) n-2 or (CH 2 ) x CH(CH 3 )(CH 2 ) y , n is from 3 to 20, x is from 1 to 8, y is from 1 to 8 with the 4-aminophthalonitrile of step (f).
References Cited (Backward Citations)
US3622596A
Cited
US3940410A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-10-31 | 1981-05-02 | 1981-11-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-31 | 1985-05-02 | 1985-11-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-31 | 1989-05-02 | 1989-11-01 | $7700.00 | Window Closed / Lapsed |