US4097460A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Poly(arylacetylenes) and thermoset resins therefrom
Assignee: Hercules LLC
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Filing: 1972-06-12
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Granted: 1978-06-27
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Expires: 1992-06-12
Abstract
Abstract The invention relates to arylacetylene polymers and thermoset resins prepared therefrom. The preferred thermoset resins are prepared by copolymerizing a polyacetylenically unsaturated prepolymer with about 2 to 70% of a monomeric acetylenically unsaturated aromatic compound that has a melting point below about 185 DEG C. and a boiling point above about 250 DEG C. The polyacetylenically unsaturated prepolymer is a polymer of at least one polyacetylenically substituted aromatic compound such as a diethynylbenzene, which prepolymer has a number average molecular weight of about 900 to 12,000 and contains about 5 to 20% by weight of acetylenic groups. Typical monomeric acetylenic aromatic compounds that are copolymerized with the prepolymer are diphenylacetylene and diphenylbutadiyne.
Inventors
- 👤 Harold Jabloner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 17:43
CPC Classifications
C; C08; C08F; C08F38/00; C08F281/00
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
105 words
A polyacetylenically unsaturated prepolymer consisting essentially of a polycyclotrimerization polymer of at least one polyacetylenically substituted aromatic compound selected from the group consisting of diethynylbenzene; diethynyltoluene; diethynylxylene; diethynylbiphenyl; 9,10-diethynylanthracene; 9,10-diethynylphenanthrene; di(ethynylphenyl)ether; 1-chloro-2,5-diethynylbenzene; 2,3,5,6-tetrachloro-1,4-diethynylbenzene; 4,4'-diethynyl-trans-azobenzene; diphenylbutadiyne; 2,2'-dichlorodiphenyldiacetylene; 4,4'-dichlorodiphenyldiacetylene; 4,4'-dibromodiphenyldiacetylene; di-p-tolyldiacetylene; di-α-naphthyldiacetylene; dibenzyldiacetylene; 1,4-bis(phenylethynyl)benzene; 1,3-bis(phenylethynyl)benzene; 9,10-bis(phenylethynyl)anthracene; 1,3,5-triethynylbenzene; 1,2,4-triethynylbenzene; 1,3,5-tris(phenylethynyl)-2,4,6-triphenylbenzene; 1,2,4-tris(phenylethynyl)-3,5,6-triphenylbenzene; tris(ethynylphenyl)benzene and mixtures of at least one of said compounds with phenylacetylene, said prepolymer having a number average molecular weight of from about 900 to about 12,000, a ratio of aromatic protons to olefinic protons from about 2.4:1 to about 38:1 and containing from about 5 to about 20% terminal acetylenic groups by weight of the prepolymer.
Claim 2
Dependent Claim
105 words
A polyacetylenically unsaturated prepolymer consisting essentially of a polycyclotrimerization polymer of at least one polyacetylenically substituted aromatic compound selected from the group consisting of diethynylbenzene; diethynyltoluene; diethynylxylene; diethynylbiphenyl; 9,10-diethynylanthracene; 9,10-diethynylphenanthrene; di(ethynylphenyl)ether; 1-chloro-2,5-diethynylbenzene; 2,3,5,6-tetrachloro-1,4-diethynylbenzene; 4,4'-diethynyl-trans-azobenzene; diphenylbutadiyne; 2,2'-dichlorodiphenyldiacetylene; 4,4'-dichlorodiphenyldiacetylene; 4,4'-dibromodiphenyldiacetylene; di-p-tolyldiacetylene; di-α-naphthyldiacetylene; dibenzyldiacetylene; 1,4-bis(phenylethynyl)benzene; 1,3-bis(phenylethynyl)benzene; 9,10-bis(phenylethynyl)anthracene; 1,3,5-triethynylbenzene; 1,2,4-triethynylbenzene; 1,3,5-tris(phenylethynyl)-2,4,6-triphenylbenzene; 1,2,4-tris(phenylethynyl)-3,5,6-triphenylbenzene; tris(ethynylphenyl)benzene and mixtures of at least one of said compounds with phenylacetylene, said prepolymer having a number average molecular weight of from about 900 to about 12,000, a ratio of aromatic protons to olefinic protons from about 2.4:1 to about 38:1 and containing from about 5 to about 20% terminal acetylenic groups by weight of the prepolymer.
Claim 3
Dependent Claim
20 words
The prepolymer of claim 1 wherein the polymer of the polyacetylenically substituted aromatic compound is a polymer of a diethynylbenzene.
Claim 4
Dependent Claim
19 words
The prepolymer of claim 2 wherein the polymer of a diethynylbenzene is a copolymer of a diethynylbenzene and diphenylbutadiyne.
Claim 5
Dependent Claim
19 words
The prepolymer of claim 2 wherein the polymer of a diethynylbenzene is a copolymer of a diethynylbenzene and phenylacetylene.
Claim 6
Independent Claim
56 words
A method of producing polyphenyl polymers comprising polycyclotrimerization of compounds selected from the group: (1) diethynyl derivatives of aromatic compounds having the formula ##STR1## (2) mixtures of said diethynyl derivatives with the monoethynyl compound having the formula ##STR2## and (3) mixtures of p-diethynylbenzene with m-diethynylbenzene, in the presence of catalysts which are complex compounds of nickel.
Claim 7
Independent Claim
56 words
A method of producing polyphenyl polymers comprising polycyclotrimerization of compounds selected from the group: (1) diethynyl derivatives of aromatic compounds having the formula ##STR1## (2) mixtures of said diethynyl derivatives with the monoethynyl compound having the formula ##STR2## and (3) mixtures of p-diethynylbenzene with m-diethynylbenzene, in the presence of catalysts which are complex compounds of nickel.
Claim 8
Dependent Claim
10 words
The polyphenyl polymers produced by the method of claim 5.
Claim 9
Dependent Claim
35 words
A method according to claim 5, wherein the process of polycyclotrimerization is carried out in the presence of said catalyst taken in an amount of 1 mole per 25-1250 moles of the starting ethynyl compounds.
Claim 10
Dependent Claim
20 words
A method according to claim 5, wherein the process of polycyclotrimerization is carried out in an aromatic compound as solvent.
Claim 11
Dependent Claim
17 words
A method according to claim 8, wherein benzene, toluene or dioxane is used as an aromatic compound.
Claim 12
Dependent Claim
21 words
A method according to claim 5, wherein the process is carried out at a temperature ranging from 55° to 250° C.
References Cited (Backward Citations)
US3066119A
Cited
US3519611A
Cited
US3749700A
Cited
US3756982A
Cited
US3705131A
Cited
US3816374A
Cited
US4020265A
Cited
US3748305A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-26 | 1981-12-26 | 1982-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-26 | 1985-12-26 | 1986-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-26 | 1989-12-26 | 1990-06-27 | $7700.00 | Window Closed / Lapsed |