Patent US4900799A successfully refreshed from Google Patents.
US4900799A
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Metathesis polymerization of cycloolefins
Assignee: Metton America Inc
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Filing: 1987-06-24
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Granted: 1990-02-13
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Expires: 2007-06-24
Abstract
Abstract A polymer prepared by metathesis polymerizing at least one compound represented by the formula <IMAGE> wherein m is 0 or 1 and R1 and R2 respectively represent hydrogen atom or an alkyl group containing up to three carbon atoms provided that both R1 and R2 are not hydrogen atom at the same time, or a mixture of said compound with at least one other metathesis polymerizable comonomer, a useful molded article, processes for preparing the polymer and a polymerizable composition therefor.
Inventors
- 👤 Shigeyoshi Hara
- 👤 Zen-ichiro Endo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 18:14
CPC Classifications
C; C08; C08F; C08F32/00; C08F32/02; C08F32/04; C08G; C08G61/00; C08G61/02; C08G61/04; C08G61/06; C08G61/08
Claims Analysis
Total Claims: 89
Claim 1
Independent Claim
52 words
A polymer which comprises at least one repeating unit having the formula selected from the group consisting of ##STR14## wherein R 1 and R 2 independently represent a hydrogen atom or an alkyl group containing up to three carbon atoms provided that both R 1 and R 2 are not hydrogen atoms.
Claim 2
Dependent Claim
52 words
A polymer which comprises at least one repeating unit having the formula selected from the group consisting of ##STR14## wherein R 1 and R 2 independently represent a hydrogen atom or an alkyl group containing up to three carbon atoms provided that both R 1 and R 2 are not hydrogen atoms.
Claim 3
Dependent Claim
19 words
A polymer of claim 1 wherein R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 4
Dependent Claim
15 words
A polymer of claim 1 consisting essentially of the repeating unit having the formula (I).
Claim 5
Dependent Claim
15 words
A polymer of claim 1 consisting essentially of the repeating unit having the formula (II).
Claim 6
Dependent Claim
21 words
A polymer of claim 1 which further comprises at least one repeating unit derived from one or more metathesis polymerizable comonomers.
Claim 7
Dependent Claim
34 words
A polymer of claim 5 which comprises 98-50 mole % of the repeating unit of the formula (I) or (II) and 2-50 mole % of the at least one metathesis polymerizable comonomer repeating unit.
Claim 8
Dependent Claim
21 words
A polymer of claim 5 which comprises the repeating unit of the formula (I) and the repeating unit derived from dicyclopentadiene.
Claim 9
Dependent Claim
19 words
A polymer of claim 7 wherein R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 10
Dependent Claim
21 words
A polymer of claim 5 which comprises the repeating unit of the formula (II) and the repeating unit derived from dicyclopentadiene.
Claim 11
Dependent Claim
19 words
A polymer of claim 9 wherein R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 12
Dependent Claim
22 words
A polymer of claim 5 wherein the at least one metathesis polymerizable comonomer is a cycloalkene having at least one norbornene structure.
Claim 13
Dependent Claim
24 words
A polymer of claim 11 wherein said cycloalkene is selected from oligocyclopentadiene containing more than two cyclopentadiene moieties in a molecule and methylcyclopentadiene-cyclopentadiene codimer.
Claim 14
Dependent Claim
35 words
A polymer of claim 11 wherein the cycloalkene further comprises at least one member selected from the group consisting of a metathesis polymerizable cyclic olefin moiety and a polar group of an organic Lewis base.
Claim 15
Dependent Claim
52 words
A polymer of claim 11 wherein said cycloalkene is selected from a cycloalkene having one norbornene structure; a cycloalkene having one norbornene structure and one metathesis polymerizable sterically-distorted cyclopentene ring; and a cycloalkene having one norbornene structure and one or two polar groups selected from cyano, ester, ether, tert-amine and amide groups.
Claim 16
Dependent Claim
18 words
A polymer of claim 14 wherein said cycloalkene is selected from dicyclopentadiene, 5-phenylnorbornene, 5-cyanonorbornene, 5-alkoxycarbonylnorbornene, 5-methylalkoxycarbonylnorbornene and 5-pyridylnorbornene.
Claim 17
Dependent Claim
10 words
A polymer of claim 15 wherein said cycloalkene is dicyclopentadiene.
Claim 18
Dependent Claim
34 words
A polymer of claim 5 which comprises 1-50 mole % of the repeating unit of the formula (I) or (II) and 99-50 mole % of the at least one metathesis polymerizable comonomer repeating unit.
Claim 19
Dependent Claim
31 words
A polymer of claim 17 which comprises 5-50 mole % of the repeating unit of the formula (I) or (II) and 95-50 mole % of the metathesis polymerizable comonomer repeating unit.
Claim 20
Dependent Claim
54 words
A polymer of claim 18 which comprises 5-50 mole % of the repeating unit of the formula (II), 95-20 mole % of the repeating unit derived from dicyclopentadiene and 0-30 mole % of a repeating unit derived from another metathesis polymerizable monomer provided that the sum of said repeating units is 100 mole %.
Claim 21
Dependent Claim
25 words
A polymer of claim 19 wherein R 1 is a methyl group and R 2 is a hydrogen atom and said other monomer is tricyclopentadiene.
Claim 22
Dependent Claim
29 words
A polymer of claim 17 which comprises 1-10 mole % of the repeating unit of the formula (I) and 99-90 mole % of the metathesis polymerizable comonomer repeating unit.
Claim 23
Dependent Claim
43 words
A polymer of claim 21 which comprises 1-10 mole % of the repeating unit of the formula (I), 99-80 mole % of the repeating unit derived from dicyclopentadiene and 0-10 mole % of a repeating unit derived from another different metathesis polymerizable monomer.
Claim 24
Dependent Claim
25 words
A polymer of claim 22 wherein R 1 is a methyl group and R 2 is a hydrogen atom and said another monomer is oligocyclopentadiene.
Claim 25
Dependent Claim
56 words
A process for preparing the polymer of claim 1 which comprises metathesis polymerizing at least one compound having the formula (III) ##STR15## wherein m is 0 or 1 and R 1 and R 2 independently represent the same group as defined in the formulae (I) and (II), in the presence of a metathesis polymerization catalyst system.
Claim 26
Dependent Claim
23 words
A process of claim 24 wherein m is 0 and R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 27
Dependent Claim
23 words
A process of claim 24 wherein m is 1 and R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 28
Dependent Claim
19 words
A process of claim 24 which comprises polymerizing only the compound of the formula (III) wherein m is 0.
Claim 29
Dependent Claim
19 words
A process of claim 24 which comprises polymerizing only the compound of the formula (III) wherein m is 1.
Claim 30
Dependent Claim
17 words
A process of claim 24 wherein the metathesis polymerization catalyst system comprises a catalyst and an activator.
Claim 31
Dependent Claim
12 words
A process of claim 21 wherein the catalyst comprises a tungsten compound.
Claim 32
Dependent Claim
12 words
A process of claim 29 wherein the activator comprises an aluminum compound.
Claim 33
Dependent Claim
11 words
A process of claim 29 wherein a moderator is further used.
Claim 34
Dependent Claim
17 words
A process of claim 29 wherein the catalyst and the activator are supplied independently in separate liquids.
Claim 35
Dependent Claim
21 words
A process of claim 33 wherein the compound of the formula (III) is introduced into at least one of the liquids.
Claim 36
Dependent Claim
18 words
A process of claim 34 wherein each of the separate liquids contains the compound of the formula (III).
Claim 37
Dependent Claim
67 words
A process of preparing the polymer of claim 5 which comprises metathesis polymerizing a mixture of at least one compound having the formula (III) ##STR16## wherein m is 0 or 1 and R 1 and R 2 independently represent the same groups as defined in the formulae (I) and (II) with at least one other metathesis polymerizable comonomer in the presence of a metathesis polymerization catalyst system.
Claim 38
Dependent Claim
31 words
A process of claim 36 which comprises polymerizing 98-50 mole % of the compound of the formula (III) and 2-50 mole % of the at least one other metathesis polymerizable comonomer.
Claim 39
Dependent Claim
31 words
A process of claim 36 which comprises polymerizing 1-50 mole % of the compound of the formula (III) and 99-50 mole % of the at least one other metathesis polymerizable comonomer.
Claim 40
Dependent Claim
28 words
A process of claim 38 which comprises polymerizing 5-50 mole % of the compound of the formula (III) and 95-50 mole % of the other metathesis polymerizable comonomer.
Claim 41
Dependent Claim
35 words
A process of claim 38 which comprises polymerizing 1-10 mole % of the compound of the formula (III) wherein m is 0 and 99-90 mole % of the at least one other metathesis polymerizable comonomer.
Claim 42
Dependent Claim
40 words
A process of claim 40 which comprises polymerizing 1-10 mole % of the compound of the formula (III) wherein m is 0, 99-80 mole % of dicyclopentadiene and 0-10 mole % of at least one different other metathesis polymerizable comonomer.
Claim 43
Dependent Claim
26 words
A process of claim 41 wherein R 1 is a methyl group, R 2 is a hydrogen atom and said different metathesis polymerizable comonomer is oligocyclopentadiene.
Claim 44
Dependent Claim
53 words
A process of claim 39 which comprises polymerizing 5-50 mole % of the compound of the formula (III) wherein m is 1, 95-20 mole % of dicyclopentadiene and 0-30 mole % of at least one different metathesis polymerizable comonomer provided that the sum of all of said comonomer amounts is 100 mole %.
Claim 45
Dependent Claim
27 words
A process of claim 43 wherein R 1 is a methyl group, R 2 is a hydrogen atom, and said at least one different comonomer is oligocyclopentadiene.
Claim 46
Dependent Claim
16 words
A process of claim 36 which comprises polymerizing the compound of the formula (III) and dicyclopentadiene.
Claim 47
Dependent Claim
22 words
A process of claim 45 wherein m is 0, R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 48
Dependent Claim
22 words
A process of claim 45 wherein m is 1, R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 49
Dependent Claim
20 words
A process of claim 36 wherein said other metathesis polymerizable comonomer is a cycloalkene having at least one norbornene structure.
Claim 50
Dependent Claim
34 words
A process of claim 48 wherein the cycloalkene further contains at least one member selected from the group consisting of a metathesis polymerizable cycloolefin moiety and a polar group of an organic Lewis base.
Claim 51
Dependent Claim
23 words
A process of claim 48 wherein said cycloalkene is selected from oligocyclopentadiene containing more than two cyclopentadiene moieties per mole and methylcyclopentadiene-cyclopentadiene codimer.
Claim 52
Dependent Claim
51 words
A process of claim 48 wherein said cycloalkene is selected from a cycloalkene having one norbornene structure; a cycloalkene having one norbornene structure and one metathesis polymerizable sterically-distorted cyclopentene ring; and a cycloalkene having one norbornene structure and one or two polar groups selected from cyano, ester, ether and tert-amine groups.
Claim 53
Dependent Claim
18 words
A process of claim 51 wherein said cycloalkene is selected from dicyclopentadiene, 5-phenylnorbornene, 5-cyanonorbornene, 5-alkoxycarbonylnorbornene, 5-methylalkoxycarbonylnorbornene and 5-pyridylnorbornene.
Claim 54
Dependent Claim
10 words
A process of claim 52 wherein said cycloalkene is dicyclopentadiene.
Claim 55
Dependent Claim
17 words
A process of claim 36 wherein the metathesis polymerization catalyst system comprises a catalyst and an activator.
Claim 56
Dependent Claim
12 words
A process of claim 54 wherein the catalyst comprises a tungsten compound.
Claim 57
Dependent Claim
12 words
A process of claim 54 wherein the activator comprises an aluminum compound.
Claim 58
Dependent Claim
11 words
A process of claim 54 wherein a moderator is further used.
Claim 59
Dependent Claim
17 words
A process of claim 54 wherein the catalyst and the activator are supplied independently in separate liquids.
Claim 60
Dependent Claim
17 words
A process of claim 58 wherein said mixture is introduced into at least one of the liquids.
Claim 61
Dependent Claim
14 words
A process of claim 59 wherein each of said separate liquids contains said mixture.
Claim 62
Dependent Claim
91 words
A multi-part polymerizable composition comprising at least one compound of the formula (III) ##STR17## wherein m is 0 or 1 and R 1 and R 2 independently represent a hydrogen atom or an alkyl group containing up to three carbon atoms, provided that both R 1 and R 2 are not hydrogen atoms or a mixture of said compound with at least one other metathesis polymerizable comonomer; and a metathesis polymerization catalyst system comprising a catalyst and an activator, said catalyst and said activator being not present in the same part.
Claim 63
Dependent Claim
91 words
A multi-part polymerizable composition comprising at least one compound of the formula (III) ##STR17## wherein m is 0 or 1 and R 1 and R 2 independently represent a hydrogen atom or an alkyl group containing up to three carbon atoms, provided that both R 1 and R 2 are not hydrogen atoms or a mixture of said compound with at least one other metathesis polymerizable comonomer; and a metathesis polymerization catalyst system comprising a catalyst and an activator, said catalyst and said activator being not present in the same part.
Claim 64
Dependent Claim
33 words
A composition of claim 61 comprising a first reactive solution containing said catalyst and said compound or said mixture and a second reactive solution containing said activator and said compound or said mixture.
Claim 65
Dependent Claim
23 words
A composition of claim 61 wherein m is 0, and R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 66
Dependent Claim
23 words
A composition of claim 61 wherein m is 1 and R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 67
Dependent Claim
12 words
A composition of claim 61 wherein the catalyst comprises a tungsten compound.
Claim 68
Dependent Claim
12 words
A composition of claim 61 wherein the activator comprises an aluminum compound.
Claim 69
Dependent Claim
9 words
A composition of claim 61 further containing a moderator.
Claim 70
Dependent Claim
17 words
A composition of claim 61 which comprises the compound of the formula (III) and the catalyst system.
Claim 71
Dependent Claim
9 words
A composition of claim 68 wherein m is 0.
Claim 72
Dependent Claim
9 words
A composition of claim 76 wherein m is 1.
Claim 73
Dependent Claim
34 words
A composition of claim 61 comprising a mixture of said compound and at least one other metathesis copolymerizable comonomer wherein said other metathesis polymerizable comonomer is a cycloalkene having at least one norbornene structure.
Claim 74
Dependent Claim
23 words
A composition of claim 71 wherein said cycloalkene is selected from oligocyclopentadiene containing more than two cyclopentadiene moieties per mole and methylcyclopentadiene-cyclopentadiene codimer.
Claim 75
Dependent Claim
34 words
A composition of claim 71 wherein the cycloalkene further contains at least one member selected from the group consisting of a metathesis polymerizable cycloolefin moiety and a polar group of an organic Lewis base.
Claim 76
Dependent Claim
51 words
A composition of claim 71 wherein said cycloalkene is selected from a cycloalkene having one norbornene structure; a cycloalkene having one norbornene structure and one metathesis polymerizable sterically-distorted cyclopentene ring; and a cycloalkene having one norbornene structure and one or two polar groups selected from cyano, ester, ether and tert-amine groups.
Claim 77
Dependent Claim
18 words
A composition of claim 71 which comprises the compound of the formula (III), dicyclopentadiene and the catalyst system.
Claim 78
Dependent Claim
22 words
A composition of claim 75 wherein m is 0, R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 79
Dependent Claim
22 words
A composition of claim 75 wherein m is 1, R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 80
Dependent Claim
18 words
A composition of claim 74 wherein said cycloalkene is selected from dicyclopentadiene, 5-phenylnorbornene, 5-cyanonorbornene, 5-alkoxycarbonylnorbornene, 5-methylalkoxycarbonylnorbornene and 5-pyridylnorbornene.
Claim 81
Dependent Claim
10 words
A composition of claim 78 wherein said cycloalkene is dicyclopentadiene.
Claim 82
Dependent Claim
29 words
A composition of claim 71 wherein the mixture comprises 98-50 mole % of the compound of the formula (III) and 2-50 mole % of the other metathesis polymerizable comonomer.
Claim 83
Dependent Claim
29 words
A composition of claim 80 wherein the mixture comprises 1-50 mole % of the compound of the formula (III) and 99-50 mole % of the other metathesis polymerizable comonomer.
Claim 84
Dependent Claim
29 words
A composition of claim 81 wherein the mixture comprises 5-50 mole % of the compound of the formula (III) and 95-50 mole % of the other metathesis polymerizable comonomer.
Claim 85
Dependent Claim
33 words
A composition of claim 81 wherein the mixture comprises 1-10 mole % of the compound of the formula (III) wherein m is 0 and 99-90 mole % of the other metathesis polymerizable comonomer.
Claim 86
Dependent Claim
24 words
A composition of claim 83 wherein the mixture comprises 99-80 mole % of dicyclopentadiene and 0-10 mole % of another different metathesis polymerizable comonomer.
Claim 87
Dependent Claim
27 words
A composition of claim 84 wherein R 1 is a methyl group, and R 2 is a hydrogen atom, and said other metathesis polymerizable comonomer is oligocyclopentadiene.
Claim 88
Dependent Claim
51 words
A composition of claim 82 wherein the mixture comprises 5-50 mole % of the compound of the formula (III) wherein m is 1, 95-20 mole % of dicyclopentadiene and 0-30 mole % of another different metathesis polymerizable comonomer provided that the sum of all of the comonomers is 100 mole %.
Claim 89
Dependent Claim
24 words
A composition of claim 86 wherein R 1 is a methyl group, and R 2 is hydrogen atom, said other comonomer is a oligocyclopentadiene.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-02-12 | 1993-08-14 | 1994-02-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-02-12 | 1997-08-14 | 1998-02-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-02-12 | 2001-08-14 | 2002-02-13 | $7700.00 | Window Closed / Lapsed |