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US4877917A
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Method of polymerizing α,ω-diynes
Assignee: University of Akron
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Filing: 1988-10-17
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Granted: 1989-10-31
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Expires: 2008-10-17
Abstract
Abstract A method of cyclization of α,ω-diynes with a transition metal catalyst such as niobium or tantalum salts such as halogen to yield products such as dimers trimers and higher polymers which may have benzo cyclobutene groups, benzocyclopentene groups, benzocyclohexene groups, or none of these, depending on the size of n in the α,ω-diynes of the formula of page 1.
Inventors
- 👤 Michael F. Farona
- 👤 Ramji Srinivasan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 22:25
CPC Classifications
C; C07; C07C; C07C15/00; C07C15/40; C07C15/50; C07C2/00; C07C2/02; C07C2/42; C07C2/48; C07C2527/00; C07C2527/06; C07C2527/133; C07C2527/135; C07C2531/00; C07C2531/02; C07C2531/12
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
61 words
A method of reacting an α,ω-diyne to form products containing at least one of the class of dimers, timers and higher polymers comprising contacting said α,ω-diyne either as a sole reactant or together with an alkyne with a niobium catalyst or tantalum catalyst to effect formation of a benzo product characterized as highly soluble to insoluble in benzene at 25° C.
Claim 2
Independent Claim
61 words
A method of reacting an α,ω-diyne to form products containing at least one of the class of dimers, timers and higher polymers comprising contacting said α,ω-diyne either as a sole reactant or together with an alkyne with a niobium catalyst or tantalum catalyst to effect formation of a benzo product characterized as highly soluble to insoluble in benzene at 25° C.
Claim 3
Dependent Claim
40 words
The method of claim 1 where the niobium catalyst is selected from the class of niobium halide and niobium halide reacted with tin aryl or alkyl or cycloalkyl compounds and the temperature of reaction is about ambient to 80° C.
Claim 4
Dependent Claim
39 words
The method of claim 1 where the reaction was terminated by addition of a terminating agent to form a precipitate, removing the precipitate and washing and reprecipitating said precipitate from a solvent to give a product free of α,ω-diyne.
Claim 5
Dependent Claim
10 words
The method of claim 1 wherein the α,ω-diyne is 1,5-hexadiyne.
Claim 6
Dependent Claim
10 words
The method of claim 1 wherein the product is 1,2-bis(benzocyclobutenyl)ethane.
Claim 7
Dependent Claim
16 words
The method of claim 1 wherein the α,ω-diyne contains from 6 to about 14 carbon atoms.
Claim 8
Dependent Claim
25 words
The method of claim 1 wherein the polymer contains a terminal aryl cyclobutene group connected to an alkyl radical having at least 2 carbon atoms.
Claim 9
Dependent Claim
26 words
The method of claim 1 wherein the polymerization occurs in the presence or an aromatic solvent selected from the class consisting of benzene, toluene, and ethylbenzene.
Claim 10
Independent Claim
87 words
A method of reacting an α,ω-diyne of the formula H--C.tbd.C(CH 2 ) n C.tbd.CH where n is an integer 2 and higher to form a product containing at least one of the species of the class consisting of dimer, trimer or higher polymer comprising contacting said α,ω-diyne with a catalyst comprising a tantalum catalyst or a niobium catalyst, or salts of said catalyst or co-catalyst of said salts with tin salts or organic tin compound at a temperature of about 10° to boiling point of the α,ω-diyne.
Claim 11
Independent Claim
87 words
A method of reacting an α,ω-diyne of the formula H--C.tbd.C(CH 2 ) n C.tbd.CH where n is an integer 2 and higher to form a product containing at least one of the species of the class consisting of dimer, trimer or higher polymer comprising contacting said α,ω-diyne with a catalyst comprising a tantalum catalyst or a niobium catalyst, or salts of said catalyst or co-catalyst of said salts with tin salts or organic tin compound at a temperature of about 10° to boiling point of the α,ω-diyne.
Claim 12
Dependent Claim
17 words
The method of claim 9 wherein the product contains a high percentage of polymers other than trimers.
Claim 13
Dependent Claim
20 words
The method of claim 10 wherein the polymer contains little gel and is essentially soluble in toluene at 25° C.
Claim 14
Dependent Claim
32 words
The method of claim 9 wherein tantalium and niobium are present as salts of the halogens chlorine and bromine and the co-catalyst is a halide of tin or a tetra aryl tin.
Claim 15
Dependent Claim
27 words
The method of claim 9 wherein at least part of the α,ω-diyne reacts with trialkyl silylacetylene to yield a product having at least one trialkyl silyl group.
Claim 16
Dependent Claim
30 words
The method of claim 9 wherein at least part of α,ω-diyne polymerizes with an acetylene having the formula H--C.tbd.CR and R is hydrogen, trialkyl Si alkyl halide, and tri-alkyl aryl-radicals.
Claim 17
Dependent Claim
11 words
The method of claim 9 wherein R is trimethyl Si radical.
Claim 18
Dependent Claim
26 words
The method of claim 9 wherein the polymerization occurs in the presence of an aromatic solvent selected from the class consisting of benzene, toluene and ethylbenzene.
References Cited (Backward Citations)
US2990434A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1992-10-30 | 1993-05-01 | 1993-10-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-10-30 | 1997-05-01 | 1997-10-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-10-30 | 2001-05-01 | 2001-10-31 | $7700.00 | Window Closed / Lapsed |