US5399646A
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Alkylidenenorbornene polymer and process for producing the same
Assignee: Zeon Corp
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Filing: 1993-07-16
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Granted: 1995-03-21
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Expires: 2013-07-16
Abstract
Abstract The present invention discloses an alkylidenenorbornene polymer comprising as the essential constituent at least one kind of the structural unit represented by the formula ##STR1## wherein R 1 denotes an alkyl group of 1-4 carbon atoms and R 2 denotes a hydrogen atom or an alkyl group of 1-5 carbon atoms, and a process for producing the same. According to the present invention, an alkylidenenorbornene polymer is obtained which is excellent in light resistance, transparency, heat resistance and moisture resistance and is useful as an optical polymeric material.
Inventors
- 👤 Teiji Kohara
- 👤 Shin-ichiro Tahara
- 👤 Yoshitsugu Hirokawa
- 👤 Tadao Natsuume
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 15:58
CPC Classifications
C; C08; C08G; C08G6/00; C08F; C08F32/00; C08F32/08
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
55 words
An alkylidenenorbornene polymer, having an intrinsic viscosity of 0.2 to 10 dl/g measured at 50° C. in decahydronaphthalene a principal chain comprising at least 50% by weight of a structural unit represented by the formula (I): ##STR8## wherein R 1 denotes an alkyl group and R 2 denotes a hydrogen atom or an alkyl group.
Claim 2
Dependent Claim
55 words
An alkylidenenorbornene polymer, having an intrinsic viscosity of 0.2 to 10 dl/g measured at 50° C. in decahydronaphthalene a principal chain comprising at least 50% by weight of a structural unit represented by the formula (I): ##STR8## wherein R 1 denotes an alkyl group and R 2 denotes a hydrogen atom or an alkyl group.
Claim 3
Dependent Claim
29 words
An alkylidenenorbornene polymer according to claim 1, wherein R 1 is a C 1-4 alkyl group and R 2 is a C 1-4 alkyl group, or a hydrogen atom.
Claim 4
Dependent Claim
25 words
An alkylidenenorbornene polymer according to claim 2, wherein R 1 is a methyl group and R 2 is a methyl group, or a hydrogen atom.
Claim 5
Dependent Claim
17 words
An alkylidenenorbornene polymer according to claim 1 which has a glass transition of 150° C. or more.
Claim 6
Dependent Claim
81 words
An alkylidenenorbornene polymer, having an intrinsic viscosity of 0.2 to 10 dl/g measured at 50° C. in decahydronaphthalene, which comprises a principal chain comprising at least 50% by weight of a first structural unit represented by the following formula I: ##STR9## wherein R 1 denotes an alkyl group and R 2 denotes a hydrogen atom or an alkyl group, and, in addition to said first structural unit, as a second structural unit in said principal chain, a different cationically polymerized monomer.
Claim 7
Dependent Claim
81 words
An alkylidenenorbornene polymer, having an intrinsic viscosity of 0.2 to 10 dl/g measured at 50° C. in decahydronaphthalene, which comprises a principal chain comprising at least 50% by weight of a first structural unit represented by the following formula I: ##STR9## wherein R 1 denotes an alkyl group and R 2 denotes a hydrogen atom or an alkyl group, and, in addition to said first structural unit, as a second structural unit in said principal chain, a different cationically polymerized monomer.
Claim 8
Dependent Claim
28 words
An alkylidenenorbornene polymer according to claim 5, wherein said cationically polymerizable monomer is a member selected from the group consisting of monoolefins, diolefins, vinylaromatic compounds and cyclic ethers.
Claim 9
Dependent Claim
27 words
An alkylidenenorbornene polymer according to claim 6, wherein said cationically polymerizable monomer is a member selected from the group consisting of isobutene, styrene, α-methylstyrene and cyclohexene oxide.
Claim 10
Dependent Claim
23 words
An alkylidenenorbornene polymer according to claim 5 which contains at least 70% by weight of the structural unit represented by the formula (I).
Claim 11
Dependent Claim
18 words
An alkylidenenorbornene polymer according to claim 5 which has a glass transition temperature of 100° C. or more.
Claim 12
Dependent Claim
18 words
An alkylidenenorbornene polymer according to claim 9 which has a glass transition temperature of 120° C. or more.
Claim 13
Dependent Claim
22 words
An alkylidenenorbornene polymer according to claim 1 which has an intrinsic viscosity of 0.4 to 5 dl/g in decahydronaphthalene at 50° C.
Claim 14
Dependent Claim
26 words
An alkylidenenorbornene polymer according to claim 1 which has a water absorption of 0.2% or less after immersion in water at 25° C. for 24 hours.
Claim 15
Dependent Claim
26 words
An alkylidenenorbornene polymer according to claim 12 which has a water absorption of 0.1% or less after immersion in water at 25° C. for 24 hours.
Claim 16
Dependent Claim
15 words
A shaped article having excellent optical properties comprising a polymer as claimed in claim 1.
Claim 17
Dependent Claim
15 words
A shaped article having excellent optical properties comprising a polymer as claimed in claim 5.
Claim 18
Dependent Claim
155 words
A process for producing an alkylidenenorbornene polymer having an intrinsic viscosity of 0.2 to 10 dl/g measured at 50° C. in decahydronaphthalene comprising a principal chain comprising at least 50% by weight of a structural unit represented by the formula (I): ##STR10## wherein R 1 denotes an alkyl group and R 2 denotes a hydrogen atom or an alkyl group, which comprises: polymerizing an alkylidenenorbornene represented by the formula (II): ##STR11## wherein R 1 and R 2 are the same meanings as defined above, or a mixture thereof with a comonomer cationically copolymerizable therewith, in the presence of a catalyst comprising a Lewis acid and an initiator compound of the formula (III): ##STR12## wherein R 3 denotes an aliphatic or aromatic hydrocarbon group, R 4 and R 5 each independently denote a lower aliphatic hydrocarbon group or an aromatic hydrocarbon group, X denotes a hydroxyl group, an alkoxyl group, an acyloxy group or a halogen.
Claim 19
Dependent Claim
155 words
A process for producing an alkylidenenorbornene polymer having an intrinsic viscosity of 0.2 to 10 dl/g measured at 50° C. in decahydronaphthalene comprising a principal chain comprising at least 50% by weight of a structural unit represented by the formula (I): ##STR10## wherein R 1 denotes an alkyl group and R 2 denotes a hydrogen atom or an alkyl group, which comprises: polymerizing an alkylidenenorbornene represented by the formula (II): ##STR11## wherein R 1 and R 2 are the same meanings as defined above, or a mixture thereof with a comonomer cationically copolymerizable therewith, in the presence of a catalyst comprising a Lewis acid and an initiator compound of the formula (III): ##STR12## wherein R 3 denotes an aliphatic or aromatic hydrocarbon group, R 4 and R 5 each independently denote a lower aliphatic hydrocarbon group or an aromatic hydrocarbon group, X denotes a hydroxyl group, an alkoxyl group, an acyloxy group or a halogen.
Claim 20
Dependent Claim
128 words
A process for producing an alkylidenenorbornene polymer having an intrinsic viscosity of 0.2 to 10 dl/g measured at 50° C. in decahydronaphthalene comprising a principal chain comprising at least 50% by weight of a structural unit represented by the formula (I): ##STR13## wherein R 1 denotes an alkyl group and R 2 denotes a hydrogen atom or an alkyl group, which comprises: polymerizing an alkylidenenorbornene represented by the formula II: ##STR14## wherein R 1 and R 2 are the same meanings as defined above, or a mixture thereof with a comonomer cationically copolymerizable therewith, in the presence of a catalyst comprising a Lewis acid and as an initiator at least one compound selected from the group consisting of 2,5-dimethyl-dihydroxyhexane, 2,5-dimethyl-2,5-diacetoxyhexane, 2,5-dimethyl-2,5-dichlorohexyne, 2,4,4,6-tetramethyl-2,6-dihydroxy heptane, 1,3-bis(2-acetoxy-2-propyl)benzene, 1,4-bis(2-methoxy-2-propyl)benzene, and 1,3,4-tris (2-bromo-2-propyl)benzene.
Claim 21
Dependent Claim
128 words
A process for producing an alkylidenenorbornene polymer having an intrinsic viscosity of 0.2 to 10 dl/g measured at 50° C. in decahydronaphthalene comprising a principal chain comprising at least 50% by weight of a structural unit represented by the formula (I): ##STR13## wherein R 1 denotes an alkyl group and R 2 denotes a hydrogen atom or an alkyl group, which comprises: polymerizing an alkylidenenorbornene represented by the formula II: ##STR14## wherein R 1 and R 2 are the same meanings as defined above, or a mixture thereof with a comonomer cationically copolymerizable therewith, in the presence of a catalyst comprising a Lewis acid and as an initiator at least one compound selected from the group consisting of 2,5-dimethyl-dihydroxyhexane, 2,5-dimethyl-2,5-diacetoxyhexane, 2,5-dimethyl-2,5-dichlorohexyne, 2,4,4,6-tetramethyl-2,6-dihydroxy heptane, 1,3-bis(2-acetoxy-2-propyl)benzene, 1,4-bis(2-methoxy-2-propyl)benzene, and 1,3,4-tris (2-bromo-2-propyl)benzene.
Claim 22
Dependent Claim
28 words
A process according to claim 16 wherein R 1 and R 2 are independently a C 1 -C 4 alkyl group, or R 2 is a hydrogen atom.
Claim 23
Dependent Claim
24 words
A process according to claim 18 wherein R 1 is a methyl group and R 2 is a methyl group or a hydrogen atom.
Claim 24
Dependent Claim
18 words
A process according to claim 16, wherein the Lewis acid is a boron halide or a titanium halide.
Claim 25
Dependent Claim
14 words
A process according to claim 16, wherein an electron donopa compound is further used.
Claim 26
Dependent Claim
22 words
A process according to claim 16, wherein said polymerizing is carried out at a temperature of from -150° C. to 100° C.
Claim 27
Dependent Claim
27 words
A process as claimed in claim 16 wherein said initiator is at least one member selected from the group consisting of tert-butanol, 2,2,4-trimethyl-2-methoxy pentane, 2-phenyl-2-propanol and 2-methoxy-2-phenylpropane.
Claim 28
Dependent Claim
66 words
A process as claimed in 21 wherein the electron donor is at least one compound represented by the formula (IV) ##STR15## wherein R 6 , R 7 and R 8 each independently denote a hydrogen atom, an aliphatic hydrocarbon group or an aromatic group, or R 6 , R 7 and R 8 may form a ring structure;and W denotes N, NO, P, PO or PS.
Claim 29
Dependent Claim
67 words
A process as claimed in claim 21 wherein the electron donor is at least one compound represented by the formula (V): ##STR16## wherein R 6 , R 7 and R 8 each independently denote a hydrogen atom, an aliphatic hydrocarbon group or an aromatic group, or R 6 , R 7 and R 8 may form a ring structure; and Y denotes CO or SO 2 .
Claim 30
Dependent Claim
68 words
A process as claimed in claim 21 wherein the electron donor is at least one compound represented by the formula (VI) R.sub.6 -Z-R.sub.7 (VI) wherein R 6 and R 7 each independently denote a hydrogen atom, an aliphatic hydrocarbon group or an aromatic group, or R 7 and R 8 may form a ring structure; and Z denotes O, CO, CO0, OCOO, S, SO or SO 2 .
Claim 31
Dependent Claim
64 words
A process as claimed in claim 21, wherein the electron donor is at least one compound represented by the formula (VII) ##STR17## wherein R 7 , R 8 , R 9 and R 10 each independently denote a hydrogen atom, an aliphatic group or an aromatic group, or R 7 , R 8 , R 9 and R 10 may form a ring structure.
References Cited (Backward Citations)
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