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US5077367A Expired / Lapsed US ⏱️ 0.0 years remaining

Crystalline syndiotactic copolymers from arylcyclobutene functional monomers and vinyl aromatic monomers

Assignee: Idemitsu Petrochemical Co Ltd
•
Filing: 1990-06-22
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Granted: 1991-12-31
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Expires: 2010-06-22
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Abstract

Abstract Syndiotactic homopolymers of an arylcyclobutene functional monomer and syndiotactic copolymers of an arylcyclobutene functional monomer and a vinylaromatic monomer are prepared by conducting the polymerization in the presence of a catalytic amount of a suitable coordination catalyst such as the reaction product of polymethylaluminoxane and a transition metal compound.

Inventors

  • 👤 Richard E. Campbell, Jr.
  • 👤 Robert A. DeVries

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 14:19
CPC Classifications
C; C08; C08F; C08F216/00; C08F12/00; C08F12/02; C08F12/32; C08J; C08J3/00; C08J3/24; Y; Y10; Y10S; Y10S526/00; Y10S526/902; Y10S526/943

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 77 words
A crystalline copolymer having a stereoregular structure of greater than 50 percent syndiotactic comprising the coordination polymerized reaction product of at least one monomer corresponding to the formula: ##STR4## wherein Ar is an aryl moiety having adjacent ring carbons thereof covalently bonded to one or more 1,2-ethanediyl or substituted ethanediyl groups; R is hydrogen, an electron donating moiety or an electron-withdrawing moiety; and m is an integer of at least 1; and one or more vinylaromatic monomers.
Claim 2
Dependent Claim 77 words
A crystalline copolymer having a stereoregular structure of greater than 50 percent syndiotactic comprising the coordination polymerized reaction product of at least one monomer corresponding to the formula: ##STR4## wherein Ar is an aryl moiety having adjacent ring carbons thereof covalently bonded to one or more 1,2-ethanediyl or substituted ethanediyl groups; R is hydrogen, an electron donating moiety or an electron-withdrawing moiety; and m is an integer of at least 1; and one or more vinylaromatic monomers.
Claim 3
Dependent Claim 17 words
A copolymer of claim 1 wherein the at least one monomer is represented by the formula: ##STR5##
Claim 4
Dependent Claim 18 words
A copolymer of claim 2, wherein the at least one monomer is represented by the following formula: ##STR6##
Claim 5
Dependent Claim 40 words
A copolymer of claim 1, wherein the vinyl aromatic monomers are represented by the formula: ##STR7## wherein each R' is independently hydrogen; an aliphatic, cycloaliphatic or aromatic hydrocarbon group having from 1 to 10 carbon atoms; or a halogen atom.
Claim 6
Dependent Claim 14 words
A copolymer of claim 4, wherein each occurrence of the vinylaromatic monomer is styrene.
Claim 7
Dependent Claim 217 words
A process for preparing a crystalline copolymer having a stereoregular structure of greater than 50 percent syndiotactic which comprises contacting at least one monomer corresponding to the formula: ##STR8## wherein Ar is an aryl moiety having adjacent ring carbons thereof covalently bonded to one or more 1,2-ethanediyl or substituted ethanediyl groups; R is hydrogen, an electron donating moiety or an electron-withdrawing moiety; and m is an integer of at least 1; and one or more vinylaromatic monomers under coordination polymerization reaction conditions in the presence of a catalytically effective amount of a catalyst comprising a transition metal compound and a polyalkylaluminoxane or a compound represented by the formula: CpMX.sub.n.sup.+ A.sup.- wherein: Cp is a single η 5 -cyclopentadienyl or η 5 -substituted cyclopentadienyl group optionally covalently bonded to M through a substituent; M is a metal of Group IIIB, IVB, VB, VIB, VIII or the Lanthanide Series of the Periodic Table bound in an η 5 bonding mode to the cyclopentadienyl or substituted cyclopentadienyl group; X is independently each occurrence halo, alkyl, aryl, N--R 2 , aryloxy or alkoxy of up to 20 carbons; R is alkyl or aryl of up to 10 carbons; n is one or two depending on the valence of M; and A is a noncoordinating, compatible anion of a Bronsted acid salt.
Claim 8
Dependent Claim 217 words
A process for preparing a crystalline copolymer having a stereoregular structure of greater than 50 percent syndiotactic which comprises contacting at least one monomer corresponding to the formula: ##STR8## wherein Ar is an aryl moiety having adjacent ring carbons thereof covalently bonded to one or more 1,2-ethanediyl or substituted ethanediyl groups; R is hydrogen, an electron donating moiety or an electron-withdrawing moiety; and m is an integer of at least 1; and one or more vinylaromatic monomers under coordination polymerization reaction conditions in the presence of a catalytically effective amount of a catalyst comprising a transition metal compound and a polyalkylaluminoxane or a compound represented by the formula: CpMX.sub.n.sup.+ A.sup.- wherein: Cp is a single η 5 -cyclopentadienyl or η 5 -substituted cyclopentadienyl group optionally covalently bonded to M through a substituent; M is a metal of Group IIIB, IVB, VB, VIB, VIII or the Lanthanide Series of the Periodic Table bound in an η 5 bonding mode to the cyclopentadienyl or substituted cyclopentadienyl group; X is independently each occurrence halo, alkyl, aryl, N--R 2 , aryloxy or alkoxy of up to 20 carbons; R is alkyl or aryl of up to 10 carbons; n is one or two depending on the valence of M; and A is a noncoordinating, compatible anion of a Bronsted acid salt.
Claim 9
Dependent Claim 20 words
A process of claim 6, wherein the polymerization is conducted at a temperature of from 0° C. to 120° C.
Claim 10
Dependent Claim 16 words
A process of claim 6, wherein the polymerization is conducted for 5 minutes to 20 hours.
Claim 11
Dependent Claim 27 words
A process of claim 6, wherein the copolymerization is conducted in the presence of a solvent selected from toluene, iso-octane, iso-nonane, hexane, heptane or a mixture thereof.
Claim 12
Dependent Claim 14 words
A process of claim 6, wherein the at least one monomer is a vinylbenzocyclobutene.
Claim 13
Dependent Claim 17 words
A process of claim 10, wherein the at least one monomer is represented by the formula: ##STR9##
Claim 14
Dependent Claim 39 words
A process of claim 6, wherein the vinylaromatic monomer is represented by the formula: ##STR10## wherein each R' is independently hydrogen; an aliphatic, cycloaliphatic or aromatic hydrocarbon group having from 1 to 10 carbon atoms; or a halogen atom.
Claim 15
Dependent Claim 11 words
A process of claim 12, wherein the vinylaromatic monomer is styrene.
Claim 16
Dependent Claim 23 words
A crosslinked crystalline polymer prepared by subjecting a mixture comprising the copolymer of claim 1 to a temperature suitable for crosslinking the copolymer.
Claim 17
Dependent Claim 19 words
A crosslinked crystalline polymer of claim 14 wherein the crosslinking is effected at from 100° C. to 320° C.
Claim 18
Dependent Claim 23 words
A crosslinked crystalline polymer according to claim 14 wherein the mixture additionally comprises a composition capable of undergoing addition polymerization under ring-opening conditions.
Claim 19
Dependent Claim 26 words
A composition prepared by subjecting a mixture comprising the crystalline copolymer of claim 1 and another polymerizable component to a temperature suitable for crosslinking the polymer.

References Cited (Backward Citations)

US3335121A Cited
US4570011A Cited
US4540763A Cited
US4667005A Cited
US4667004A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-12-30 1995-07-01 1995-12-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-12-30 1999-07-01 1999-12-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-12-30 2003-07-01 2003-12-31 $7700.00 Window Closed / Lapsed

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