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US3926897A Expired / Lapsed US ⏱️ 0.0 years remaining

Thermosetting compositions containing poly(arylacetylenes) and an aromatic ring compound having the rings joined through a keto group

Assignee: Hercules LLC
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Filing: 1974-06-03
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Granted: 1975-12-16
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Expires: 1994-06-03
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Abstract

Abstract The invention relates to thermosetting compositions which are blends of novel poly(arylacetylenes) and, as fluidizers, certain aromatic organic compounds containing at least two aromatic rings. The poly(arylacetylenes) are prepolymers of polyacetylenically substituted aromatic compounds, which prepolymers have a number average molecular weight of from about 900 to about 12,000 and contain from about 5 to about 20 percent by weight of acetylenic groups. Diethynylbenzene is one of the preferred monomers used in preparation of the prepolymers. Representative of the compounds containing at least two aromatic ring is benzophenone. The compositions are curable by heat to produce thermoset resins which have very desirable physical properties at both normal and high temperatures.

Inventors

  • 👤 Jr Lawrence C Cessna

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 08:29
CPC Classifications
C; C08; C08F; C08F8/00; C08F38/00; C08K; C08K5/00; C08K5/04; C08K5/07

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 122 words
A THERNOSETTING COMPOSITION COMPRISING A BLEND OF (1) A PREPOLYMER OF AT LEAST ONE POLYACETYLENICALLY SUBSTITUTED AROMATIC COMPOUND, SAID PREPOLYMER HAVING A NUMBER AVERAGE MOLECULAR WEIGHT FROM ABOUT 900 TO ABOUT 12,000, A RATIO OF AROMATIC PROTONS OF OLEFINIC PROTONS GREATER THAN ABOUT 2.4 AND CONTAINING FROM ABOUT 5 TO ABOUT 20 PERCENT ACETYLENIC GROUPS BY WEIGHT OF THE PREPOLYMER, WITH (2) FROM ABOUT 2 TO ABOUT 200 PERCENT, BY WEIGHT OF THE PREPOLYMER, OF A LEAST ONE AROMAIC ORGANIC COMPOUND CONTAINING AT LEAST TWO SIXMEMBERED AROMATIC RINGS, SAID RINGS BEING COUPLED WITH EACH OTHER THROUGH A KETO GROUP, SAID RINGS BEING COUPLED WITH EACH THEREOF HAVING A MELTING POINT LESS THAN ABOUT 220*C AND A BOILING POINT GREATER THAN ABOUT 240*C.
Claim 2
Dependent Claim 122 words
A THERNOSETTING COMPOSITION COMPRISING A BLEND OF (1) A PREPOLYMER OF AT LEAST ONE POLYACETYLENICALLY SUBSTITUTED AROMATIC COMPOUND, SAID PREPOLYMER HAVING A NUMBER AVERAGE MOLECULAR WEIGHT FROM ABOUT 900 TO ABOUT 12,000, A RATIO OF AROMATIC PROTONS OF OLEFINIC PROTONS GREATER THAN ABOUT 2.4 AND CONTAINING FROM ABOUT 5 TO ABOUT 20 PERCENT ACETYLENIC GROUPS BY WEIGHT OF THE PREPOLYMER, WITH (2) FROM ABOUT 2 TO ABOUT 200 PERCENT, BY WEIGHT OF THE PREPOLYMER, OF A LEAST ONE AROMAIC ORGANIC COMPOUND CONTAINING AT LEAST TWO SIXMEMBERED AROMATIC RINGS, SAID RINGS BEING COUPLED WITH EACH OTHER THROUGH A KETO GROUP, SAID RINGS BEING COUPLED WITH EACH THEREOF HAVING A MELTING POINT LESS THAN ABOUT 220*C AND A BOILING POINT GREATER THAN ABOUT 240*C.
Claim 3
Dependent Claim 15 words
The thermosetting composition of claim 1 wherein the prepolymer comprises a polymer of a diethynylbenzene.
Claim 4
Dependent Claim 20 words
The thermosetting composition of claim 2 wherein the polymer of a diethynylbenzene is a copolymer of a diethynylbenzene and diphenylbutadiyne.
Claim 5
Dependent Claim 20 words
The thermosetting composition of claim 2 wherein the polymer of a diethynylbenzene is a copolymer of a diethynylbenzene and phenylacetylene.
Claim 6
Dependent Claim 13 words
The thermosetting composition of claim 2 wherein the aromatic organic compound is fluorenone.
Claim 7
Dependent Claim 13 words
The thermosetting composition of claim 2 wherein the aromatic organic compound is benzophenone.
Claim 8
Dependent Claim 15 words
The thermosetting composition of claim 6 wherein diphenylbutadiyne is used in conjunction with the benzophenone.
Claim 9
Dependent Claim 169 words
The process of preparing a thermoset resin essentially free of aliphatic unsaturation which comprises (1) in a first stage (a) preparing a prepolymer by polymerizing at least one polyacetylenically substituted aromatic compound by heating said compound with an aromatization catalyst in an inert organic diluent to a temperature of from about 55*C. to about 250*C. until from about 30 percent to about 90 percent of said compound has been converted to polymer, (b) separating the prepolymer from the polymerization reaction mixture, and (2) in a second stage, (a) fabricating a blend of said prepolymer and from about 2 to about 200 percent, by weight of the prepolymer, of at least one aromatic organic compound containing at least two six-membered aromatic rings, said rings being coupled with each other through a keto group, said compound or mixtures thereof having a melting point less than about 220*C. and a boiling point greater than about 240*C., and (b) heating the fabricated blend to a temperature of from about 100*C. to about 300*C.
Claim 10
Dependent Claim 169 words
The process of preparing a thermoset resin essentially free of aliphatic unsaturation which comprises (1) in a first stage (a) preparing a prepolymer by polymerizing at least one polyacetylenically substituted aromatic compound by heating said compound with an aromatization catalyst in an inert organic diluent to a temperature of from about 55*C. to about 250*C. until from about 30 percent to about 90 percent of said compound has been converted to polymer, (b) separating the prepolymer from the polymerization reaction mixture, and (2) in a second stage, (a) fabricating a blend of said prepolymer and from about 2 to about 200 percent, by weight of the prepolymer, of at least one aromatic organic compound containing at least two six-membered aromatic rings, said rings being coupled with each other through a keto group, said compound or mixtures thereof having a melting point less than about 220*C. and a boiling point greater than about 240*C., and (b) heating the fabricated blend to a temperature of from about 100*C. to about 300*C.
Claim 11
Dependent Claim 30 words
The process of claim 8 wherein the prepolymer prepared in the first stage is prepared from a diethynylbenzene and the aromatic organic compound used in the second stage is benzophenone.

References Cited (Backward Citations)

US3066119A Cited
US3300456A Cited
US3562236A Cited
US3645999A Cited
US3705131A Cited
US3709863A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-12-15 1979-06-16 1979-12-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-12-15 1983-06-16 1983-12-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-12-15 1987-06-16 1987-12-16 $7700.00 Window Closed / Lapsed

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