Patent US4708969A successfully refreshed from Google Patents.
US4708969A
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US
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Cycloolefin composition and method for making high TG fiber reinforced polymeric product
Assignee: Metton America Inc
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Filing: 1986-06-13
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Granted: 1987-11-24
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Expires: 2006-06-13
Abstract
Abstract A composition and method for polymerization of cycloolefins using a feed stream including an iodide containing activator to form a substantially cross-linked polymeric product. The polymeric product may be formed by polymerization in an intricately shaped mold and/or be of ultra-low density. High glass transition temperature and fiber reinforced products are formed.
Inventors
- 👤 Douglas R. Leach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 22:04
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/02; C08G61/04; C08G61/06; C08G61/08
Claims Analysis
Total Claims: 51
Claim 1
Independent Claim
38 words
A low solvent feed composition for polymerization of cyclic olefin having less than one percent of noncycloolefin solvent on a molar basis, comprising: (a) at least two cyclic olefins; and (b) an activator mixture comprising a dialkylaluminum iodide.
Claim 2
Dependent Claim
38 words
A low solvent feed composition for polymerization of cyclic olefin having less than one percent of noncycloolefin solvent on a molar basis, comprising: (a) at least two cyclic olefins; and (b) an activator mixture comprising a dialkylaluminum iodide.
Claim 3
Dependent Claim
14 words
The feed composition of claim 1 further comprising a trialkylaluminum or a dialkylaluminum chloride.
Claim 4
Dependent Claim
15 words
The composition of claim 2 wherein said dialkylaluminum iodide is diethylaluminum iodide or dioctylaluminum iodide.
Claim 5
Dependent Claim
16 words
The composition of claim 2 wherein said trialkylaluminum is trioctylaluminum said dialkylaluminum chloride is diethylaluminum chloride.
Claim 6
Dependent Claim
10 words
The compostion of claim 2 wherein further comprising a catalyst.
Claim 7
Dependent Claim
16 words
The composition of claim 5 wherein said catalyst includes a tungsten oxyhalide and a tungsten halide.
Claim 8
Dependent Claim
8 words
The composition of claim 2 further comprising elastomer.
Claim 9
Dependent Claim
21 words
The composition of claim 1 wherein at least one of said cyclic olefins is dicyclo pentadiene or 1,4,5,8 dimethano-1,4,4a,5,8,8a octahydronaphthalene (DMON)
Claim 10
Dependent Claim
75 words
The composition of claim 1 wherein one of said cyclic olefins is a compound of the general formula: ##STR3## wherein R 1 , R 2 , R 3 and R 4 are each independently hydrogen, alkyl of from 1-10 carbon, halogen substituted alkyl,aryl, substituted aryl or saturated and unsaturated hydrocarbon cyclic groups formed by R 1 and R 2 together with the two ring carbon atoms bonded thereto wherein substituents are alkyl, aryl or halogen.
Claim 11
Independent Claim
45 words
A method of making substantially cross-linked polymerized cyclic olefin, comprising: (a) providing a polymerization mixture comprising (i) at least two cyclic olefins, (ii) a catalyst, (iii) an activator mixture comprising dialkylaluminum iodide, and (b) polymerizing said polymerization mixture to form substantially cross-linked polymerized cyclic olefin.
Claim 12
Independent Claim
45 words
A method of making substantially cross-linked polymerized cyclic olefin, comprising: (a) providing a polymerization mixture comprising (i) at least two cyclic olefins, (ii) a catalyst, (iii) an activator mixture comprising dialkylaluminum iodide, and (b) polymerizing said polymerization mixture to form substantially cross-linked polymerized cyclic olefin.
Claim 13
Dependent Claim
14 words
The method of claim 10 further comprises a trialkylaluminum compound or a dialkylaluminum chloride.
Claim 14
Dependent Claim
12 words
The method of claim 10 wherein said polymerization mixture further comprises elastomer.
Claim 15
Dependent Claim
72 words
The method of claim 10 wherein said substantially cross-linked polymerized cyclic olefin is a thermoset polymer consisting essentially of polymerized units of dicyclopentadiene and 1,4,5,8 dimethano-1,4a,5,8,8a octahydronaphthalene and has a notched Izod impact strength of at least 1.5 ft-lb/in. notch, a flexural modulus of at least 150,000 psi and a percent gel swell determined after the polymer is immersed in toluene for two hours at 100° C. of less than about 200%.
Claim 16
Dependent Claim
13 words
The method of claim 10 wherein one of said cyclic olefins is dicyclopentadiene.
Claim 17
Dependent Claim
18 words
The method of claim 14 wherein one of said cyclic olefin comprises dicyclopentadiene and 1,4,5,8 dimethano-1,4,4a,5,8,8a octahydronaphthalene (DMON).
Claim 18
Dependent Claim
22 words
The method of claim 10 further comprising providing intertwined fiberous material in a mold and conveying said polymerization mixture into said mold.
Claim 19
Dependent Claim
23 words
A substantially cross-linked thermoset polymeric composition comprising: (a) substantially cross-linked polymerized units of at least two cyclic olefins, and (b) a dialkylaluminum iodide.
Claim 20
Dependent Claim
23 words
A substantially cross-linked thermoset polymeric composition comprising: (a) substantially cross-linked polymerized units of at least two cyclic olefins, and (b) a dialkylaluminum iodide.
Claim 21
Dependent Claim
22 words
The composition of claim 17 further comprising a trialkylaluminum compound or a dialkylaluminum chloride and one of said cyclic olefins is dicyclopentadiene.
Claim 22
Dependent Claim
14 words
A cross-linked thermoset polymer compostion comprising polymerized units of dicyclopentadiene and 1,4,5,8 dimethano-1,4,4a,5,8,8a octahydronaphthalene.
Claim 23
Dependent Claim
14 words
A cross-linked thermoset polymer compostion comprising polymerized units of dicyclopentadiene and 1,4,5,8 dimethano-1,4,4a,5,8,8a octahydronaphthalene.
Claim 24
Dependent Claim
17 words
The composition of claim 19 wherein said composition comprises from 35 to 70 percent by weight DMON.
Claim 25
Independent Claim
53 words
A method of mold filling for polymerization of cyclic olefin to form cross-linked cyclic olefin comprising: (a) providing a polymerization mixture comprising (i) at least two cyclic olefins; (ii) activator comprising dialkylaluminum iodide; and (b) conveying said polymerization mixture to mold means, and allowing said mixture to polymerize to form a molded product.
Claim 26
Independent Claim
53 words
A method of mold filling for polymerization of cyclic olefin to form cross-linked cyclic olefin comprising: (a) providing a polymerization mixture comprising (i) at least two cyclic olefins; (ii) activator comprising dialkylaluminum iodide; and (b) conveying said polymerization mixture to mold means, and allowing said mixture to polymerize to form a molded product.
Claim 27
Dependent Claim
17 words
The method of claim 21 wherein said activator further comprises a trialkylaluminum compound or a dialkylaluminum chloride.
Claim 28
Dependent Claim
18 words
The method of claim 21 wherein one of said cyclic olefins is dicyclopentadiene or 1,4,5,8 dimethano-1,4,4a,5,8,8a octahydronaphthalene (DMON).
Claim 29
Dependent Claim
12 words
The method of claim 21 wherein said polymerization mixture further comprises elastomer.
Claim 30
Dependent Claim
27 words
A substantially cross-linked thermoset polymeric composition comprising: (a) substantially cross-linked polymerized units of at least one cyclic olefin, and (b) fiberous material, and (c) an alkylaluminum iodide.
Claim 31
Dependent Claim
27 words
A substantially cross-linked thermoset polymeric composition comprising: (a) substantially cross-linked polymerized units of at least one cyclic olefin, and (b) fiberous material, and (c) an alkylaluminum iodide.
Claim 32
Dependent Claim
14 words
The composition of claim 25 further comprising a trialkylaluminum compound or a dialkylaluminum chloride.
Claim 33
Dependent Claim
25 words
The composition of claim 25 wherein said cyclic olefin is dicyclopentadiene DMON or a substituted DMON and said composition comprises at least two cyclic olefins.
Claim 34
Dependent Claim
14 words
The composition of claim 25 wherein said fiberous material is glass, graphite or aramid.
Claim 35
Dependent Claim
14 words
The composition of claim 25 wherein said fiberous material is woven, intertwined or interlaced.
Claim 36
Independent Claim
60 words
A method of mold filling for polymerization of cyclic olefin to form cross-linked cyclic olefin comprising: (a) providing a polymerization mixture comprising (i) cyclic olefin; (ii) activator comprising an alkylaluminum iodide; (b) providing a mold means containing fiberous material, and (c) conveying said polymerization mixture to said mold means, and allowing said mixture to polymerize to form a molded product.
Claim 37
Independent Claim
60 words
A method of mold filling for polymerization of cyclic olefin to form cross-linked cyclic olefin comprising: (a) providing a polymerization mixture comprising (i) cyclic olefin; (ii) activator comprising an alkylaluminum iodide; (b) providing a mold means containing fiberous material, and (c) conveying said polymerization mixture to said mold means, and allowing said mixture to polymerize to form a molded product.
Claim 38
Dependent Claim
17 words
The method of claim 30 wherein said activator further comprises a trialkylaluminum compound or a dialkylaluminum chloride.
Claim 39
Dependent Claim
16 words
The method of claim 30 wherein said cyclic olefin is dicyclopentadiene or 1,4,5,8 dimethano-1,4,4a,5,8,8a octahydronaphthalene (DMON).
Claim 40
Dependent Claim
29 words
The method of claim 30 wherein said cyclic olefin comprises at least two cyclic olefins; said activator is dioctylaluminum iodide and said fibrous material is glass, graphite, or aramid.
Claim 41
Dependent Claim
58 words
A composite product, comprising an interlaced fibrous material, and cross-linked polymer, said polymer comprising polymerized units of cycloolefin, said polymer having been formed from a reactive mixture, said reactive mixture comprising cycloolefin, a tungsten containing compound as a catalyst, and an iodide containing compound as activator in contact with said fibrous material to form a composite polymeric product.
Claim 42
Dependent Claim
58 words
A composite product, comprising an interlaced fibrous material, and cross-linked polymer, said polymer comprising polymerized units of cycloolefin, said polymer having been formed from a reactive mixture, said reactive mixture comprising cycloolefin, a tungsten containing compound as a catalyst, and an iodide containing compound as activator in contact with said fibrous material to form a composite polymeric product.
Claim 43
Dependent Claim
32 words
The product of claim 34 wherein said composite polymeric product has a flex modulus of at least 460,000 p.s.i.a., and a notched Izod impact strength of at least 8.5 foot/pounds per inch.
Claim 44
Dependent Claim
21 words
The product of claim 34 wherein said modulus is at least 600,000 p.s.i.a said fibrous material comprises glass, graphite, or aramid.
Claim 45
Dependent Claim
30 words
The product of claim 34 wherein said fiberous material comprises woven, intertwined or interlaced fibers and said fibers are substantially interdependent in their response to forces applied to the product.
Claim 46
Dependent Claim
22 words
The product of claim 34 wherein said product is formed in a mold and said fiberous material comprise glass, graphite or aramid.
Claim 47
Dependent Claim
56 words
A substantially cross-linked polymeric composition comprising: substantially cross-linked polymerized units of at least two cyclic olefins, one said cyclic olefin being dicyclopentadiene, and another of said cyclic olefin being a nonpolar cyclic olefin other than dicyclopentadiene, at least 30 percent by weight of the total weight of said two cyclic olefins being said nonpolar cyclic olefin.
Claim 48
Dependent Claim
56 words
A substantially cross-linked polymeric composition comprising: substantially cross-linked polymerized units of at least two cyclic olefins, one said cyclic olefin being dicyclopentadiene, and another of said cyclic olefin being a nonpolar cyclic olefin other than dicyclopentadiene, at least 30 percent by weight of the total weight of said two cyclic olefins being said nonpolar cyclic olefin.
Claim 49
Dependent Claim
25 words
The composition of claim 39 wherein said composition is a block copolymer and said composition has a glass transition temperature of at least 170° C.
Claim 50
Dependent Claim
39 words
The composition of claim 39 wherein said composition has a glass transition temperature of at least 190° C. and at least 35 percent by weight of the total weight of said two cyclic olefins is said nonpolar cyclic olefin.
Claim 51
Dependent Claim
11 words
The composition of claim 39 wherein said composition is a foam.
References Cited (Backward Citations)
US3084147A
Cited
US3446785A
Cited
US3557072A
Cited
US3684787A
Cited
US3873644A
Cited
US3974092A
Cited
US3974094A
Cited
US3627739A
Cited
US4002815A
Cited
US3935179A
Cited
US4020254A
Cited
US4250063A
Cited
JPS5392000A
Cited
JPS53111399A
Cited
US4136249A
Cited
US4178424A
Cited
US4136247A
Cited
US4136248A
Cited
US4380617A
Cited
US4469809A
Cited
US4400340A
Cited
US4436858A
Cited
US4485208A
Cited
US4426502A
Cited
US4418179A
Cited
US4481344A
Cited
US4458037A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-11-23 | 1991-05-25 | 1991-11-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-11-23 | 1995-05-25 | 1995-11-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-11-23 | 1999-05-25 | 1999-11-24 | $7700.00 | Window Closed / Lapsed |