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US4038471A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for preparing high-cis polyalkenamers

Assignee: Goodyear Tire and Rubber Co
•
Filing: 1976-10-29
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Granted: 1977-07-26
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Expires: 1996-10-29
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Abstract

Abstract There is disclosed a method which comprises polymerizing a cycloolefin selected from the group consisting of cyclooctene and 1,5-cyclooctadiene by subjecting said cycloolefin to a catalyst comprising (A) a tungsten halide salt of the general formula R m -n WX n wherein X represents chlorine or bromine and R is selected from the group consisting of alkoxy, haloalkoxy, aryloxy, alkaryloxy, and acetyl acetonyl radicals containing up to 20 carbon atoms; m being 6 when X= Cl or 5 when X = Br; and wherein n may be 3 to 6 inclusive when X = Cl or 3 to 5 inclusive when X = Br and (B) an organoaluminum compound of the formula: ##STR1## wherein R 1 , R 2 and R 3 may independently represent an alkyl or aralkyl radical containing up to 20 carbon atoms or a halogen atom, and (C) a hydroxyl compound of the formula ROH wherein R is selected from the group consisting of alkyl, haloalkyl, cycloalkyl, aralkyl, alkoxyalkyl and aryl containing up to 20 carbon atoms, and (D) a hindered phenol of the formula ##STR2## wherein R 1 represents an alkyl group with a tertiary carbon attached to the aromatic ring, and R 2 , R 3 and R 4 represent either a hydrogen atom or an alkyl group containing up to 20 carbon atoms, to form polyalkenamers having a cis-vinylene content of at least about 85 percent, and wherein the molar ratio of A:B:C:D ranges from 1:2-8:0.5-3:3-24.

Inventors

  • 👤 Kenneth F. Castner

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 18:14
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/02; C08G61/04; C08G61/06; C08G61/08

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 251 words
The method which comprises polymerizing a cycloolefin selected from the group consisting of cyclooctene and 1,5-cyclooctadiene by subjecting said cycloolefin to a catalyst comprising (A) a tungsten halide salt of the general formula R m -n WX n wherein X represents chlorine or bromine and R is selected from the group consisting of alkoxy, haloalkoxy, aryloxy, alkaryloxy, and acetyl acetonyl radicals containing up to 20 carbon atoms; m being 6 when X = Cl or 5 when X = Br; and wherein n may be 3 to 6 inclusive when X = Cl or 3 or 5 inclusive when X = Br and (B) an organoaluminum compound of the formula: ##STR10## wherein R 1 , R 2 and R 3 may independently represent an alkyl or aralkyl radical containing up to 20 carbon atoms or a halogen atom, and (C) a hydroxyl compound which is phenol or o-, m- or p-cresol or which is of the formula ROH wherein R is selected from the group consisting of alkyl, haloalkyl, cycloalkyl, aralkyl and alkoxyalkyl containing up to 20 carbon atoms, and (D) a hindered phenol of the formula ##STR11## wherein R 1 represents an alkyl group with a tertiary carbon attached to the aromatic ring, and R 2 , R 3 and R 4 represent either a hydrogen atom or an alkyl group containing up to 20 carbon atoms, to form polyalkenamers having a cisvinylene content of at least about 85 percent, and wherein the molar ratio of A:B:C:D ranges from 1:2-8:0.5-3:3--24.
Claim 2
Independent Claim 251 words
The method which comprises polymerizing a cycloolefin selected from the group consisting of cyclooctene and 1,5-cyclooctadiene by subjecting said cycloolefin to a catalyst comprising (A) a tungsten halide salt of the general formula R m -n WX n wherein X represents chlorine or bromine and R is selected from the group consisting of alkoxy, haloalkoxy, aryloxy, alkaryloxy, and acetyl acetonyl radicals containing up to 20 carbon atoms; m being 6 when X = Cl or 5 when X = Br; and wherein n may be 3 to 6 inclusive when X = Cl or 3 or 5 inclusive when X = Br and (B) an organoaluminum compound of the formula: ##STR10## wherein R 1 , R 2 and R 3 may independently represent an alkyl or aralkyl radical containing up to 20 carbon atoms or a halogen atom, and (C) a hydroxyl compound which is phenol or o-, m- or p-cresol or which is of the formula ROH wherein R is selected from the group consisting of alkyl, haloalkyl, cycloalkyl, aralkyl and alkoxyalkyl containing up to 20 carbon atoms, and (D) a hindered phenol of the formula ##STR11## wherein R 1 represents an alkyl group with a tertiary carbon attached to the aromatic ring, and R 2 , R 3 and R 4 represent either a hydrogen atom or an alkyl group containing up to 20 carbon atoms, to form polyalkenamers having a cisvinylene content of at least about 85 percent, and wherein the molar ratio of A:B:C:D ranges from 1:2-8:0.5-3:3--24.
Claim 3
Dependent Claim 13 words
The method of claim 1 in which the hindered phenol is 2-t-butyl phenol.
Claim 4
Dependent Claim 12 words
The method of claim 1 in which the hindered phenol is 2-t-butyl-p-cresol.
Claim 5
Dependent Claim 12 words
The method of claim 1 in which the hindered phenol is 6-t-butyl-m-cresol.
Claim 6
Dependent Claim 12 words
The method of claim 1 in which the hindered phenol is 2-t-hexyl-p-cresol.
Claim 7
Dependent Claim 32 words
The method of claim 1 in which the tungsten halide salt is tungsten hexacloride, the organoaluminum compound is ethylaluminum dichloride, the hydroxy compound is ethyl alcohol, and the hindered phenol is 2-t-butyl-p-cresol.

References Cited (Backward Citations)

US3652487A Cited
US3974094A Cited
US3943116A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-07-25 1981-01-24 1981-07-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-07-25 1985-01-24 1985-07-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-07-25 1989-01-24 1989-07-26 $7700.00 Window Closed / Lapsed

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