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US3867361A Expired / Lapsed US ⏱️ 0.0 years remaining

A process for the polymerization of cyclic olefins

Assignee: Goodyear Tire and Rubber Co
•
Filing: 1966-03-28
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Granted: 1975-02-18
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Expires: 1986-03-28
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Abstract

Abstract There is disclosed a polymerization process comprising polymerizing at least one unsaturated alicyclic compound selected from the group consisting of (1) unsaturated alicyclic compounds containing 4 or 5 carbon atoms in the cyclic ring and containing 1 carbon-to-carbon double bond in the cyclic ring, and (2) unsaturated alicyclic compounds containing at least 8 carbon atoms in the cyclic ring and containing at least 1 carbon-tocarbon double bond in the cyclic ring, by subjecting said alicyclic compounds to polymerization conditions in the presence of a catalyst system comprising (a) at least one organometallic compound wherein the metal is selected from the group consisting of Ia, IIa, IIb and IIIa of the Periodic Table of Elements, (b) at least one metal salt wherein the metal is selected from the group consisting of molybdenum and tungsten and (c) at least one compound of the general formula R-S-H wherein R is a radical selected from the group consisting of (1) hydrogen, (2) alkyl, (3) aryl, (4) aryalkyl, (5) alkaryl, (6) alkenyl, (7) thioalkyl, thioaryl and thioalkaryl and radicals of (2) through (6) wherein at least one hydrogen is substituted by thiol (SH) and wherein the relationship between these three catalyst components defined by (a), (b) and (c) are within a molar ratio of (b)/(c) ranging from 0.3/1 to at least 20/1 and the molar ratio of (a)/(b) is within the range from about 0.5/1 to at least about 15/1.

Inventors

  • 👤 Nissim Calderon
  • 👤 William Allen Judy

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 21:36
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/02; C08G61/04; C08G61/06; C08G61/08; C08F; C08F4/00; C08F4/06; C08F4/12; Y; Y10; Y10S; Y10S526/00; Y10S526/907

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 231 words
A POLYMERIZATION PROCESS COMPRISING POLYMERIZING AT LEAST ONE UNSATURATED ALICYCLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF (1) UNSATURATED ALICYCLIC COMPOUNDS CONTAINING 4 OR 5 CARBON ATOMS IN THE CYCLIC RING AND CONTAINING 1 CARBON-TO-CARBON DOUBLE BOND IN THE CYCLIC RING, AND (2) UNSATURATED ALICYCLIC COMPOUNDS CONTAINING AT LEAST 8 CARBON-TOATOMS IN THE CYCLIC RING AND CONTAINING AT LEAST 1 CARBON-TOCARBON DOUBLE BOND IN THE CYCLIC RING, BY SUBJECTING SAID ALICYCLIC COMPOUNDS TO POLYMERIZATION CONDITIONS IN THE PRESENCE OF A CATALYST SYSTE COMPRISING (A) AT LEAST ONE ORGANOMETALLIC COMPOUND WHEREIN THE METAL IS SELECTED FROM THE GROUP CONSISTING OF IA, IIA, IIB AND IIA OF THE PERIODIC TABLE OF ELEMENTS, (B) AT LEAST ONE METAL SALT WHEREIN THE METAL IS SELECTED FOM THE GROUP CONSISTING OF MOLYBDENUM AND TUNGSTEN AND (C) AT LEAST ONE METAL SALT WHEREIN THE METAL IS R-S-H WHEREIN IS A RADICAL SELECTED FROM THE GROUP CONSISTING OF (1) HYDROGEN, (2) ALKYL, (3) ARYL, (4) ARYLALKYL, (5) ALKARYL, (6) ALKENYL (7) THIOALKYL, THIOARYL AND THIOALKARYL AND RADICALS OF (2) THROUGH (6) WHEREIN AT LEAST ONE HYDROGEN IS SUBSTITUTED BY THIOL (SH) AND WHEREIN THE RELATIONSHIP BETWEEN THESE THREE CATALYST COMPONENTS DEFINED BY (A), (B) AND (C) ARE WITHIN A MOLAR RATIO OF (B)/(C) RANGING FROM 0.3/1 TO AT LEAST 20/1 AND THE MOLAR RATIO OF (A)/(B) IS WITHIN THE RANGE FROM ABOUT 0.5/1 TO AT LEAST ABOUT 15/1.
Claim 2
Dependent Claim 231 words
A POLYMERIZATION PROCESS COMPRISING POLYMERIZING AT LEAST ONE UNSATURATED ALICYCLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF (1) UNSATURATED ALICYCLIC COMPOUNDS CONTAINING 4 OR 5 CARBON ATOMS IN THE CYCLIC RING AND CONTAINING 1 CARBON-TO-CARBON DOUBLE BOND IN THE CYCLIC RING, AND (2) UNSATURATED ALICYCLIC COMPOUNDS CONTAINING AT LEAST 8 CARBON-TOATOMS IN THE CYCLIC RING AND CONTAINING AT LEAST 1 CARBON-TOCARBON DOUBLE BOND IN THE CYCLIC RING, BY SUBJECTING SAID ALICYCLIC COMPOUNDS TO POLYMERIZATION CONDITIONS IN THE PRESENCE OF A CATALYST SYSTE COMPRISING (A) AT LEAST ONE ORGANOMETALLIC COMPOUND WHEREIN THE METAL IS SELECTED FROM THE GROUP CONSISTING OF IA, IIA, IIB AND IIA OF THE PERIODIC TABLE OF ELEMENTS, (B) AT LEAST ONE METAL SALT WHEREIN THE METAL IS SELECTED FOM THE GROUP CONSISTING OF MOLYBDENUM AND TUNGSTEN AND (C) AT LEAST ONE METAL SALT WHEREIN THE METAL IS R-S-H WHEREIN IS A RADICAL SELECTED FROM THE GROUP CONSISTING OF (1) HYDROGEN, (2) ALKYL, (3) ARYL, (4) ARYLALKYL, (5) ALKARYL, (6) ALKENYL (7) THIOALKYL, THIOARYL AND THIOALKARYL AND RADICALS OF (2) THROUGH (6) WHEREIN AT LEAST ONE HYDROGEN IS SUBSTITUTED BY THIOL (SH) AND WHEREIN THE RELATIONSHIP BETWEEN THESE THREE CATALYST COMPONENTS DEFINED BY (A), (B) AND (C) ARE WITHIN A MOLAR RATIO OF (B)/(C) RANGING FROM 0.3/1 TO AT LEAST 20/1 AND THE MOLAR RATIO OF (A)/(B) IS WITHIN THE RANGE FROM ABOUT 0.5/1 TO AT LEAST ABOUT 15/1.
Claim 3
Dependent Claim 17 words
The process according to claim 1 in which the (b) catalyst component is a halide of tungsten.
Claim 4
Dependent Claim 16 words
The process according to claim 1 in which the (a) catalyst component is an organoaluminum compound.
Claim 5
Dependent Claim 15 words
The process according to claim 1 in which the (c) catalyst component is a mercaptan.
Claim 6
Dependent Claim 29 words
The process according to claim 1 in which the unsaturated alicyclic compound contains from 4 to 5 carbon atoms and only one carbon-to-carbon double bond in the cyclic ring.
Claim 7
Dependent Claim 51 words
The process according to claim 1 in which the unsaturated alicyclic compound contains 8 and not more than 12 carbon atoms in the cyclic ring and contains from 1 to 3 carbon-to-carbon double bonds in the cyclic ring which are located in relation to each other that they are not conjugated.
Claim 8
Dependent Claim 16 words
The process according to claim 1 in which a mixture of cyclooctene and 1,5-cyclooctadiene are copolymerized.
Claim 9
Dependent Claim 11 words
The process according to claim 1 in which cyclooctadiene is homopolymerized.
Claim 10
Dependent Claim 14 words
The process according to claim 1 in which the polymerization is conducted in bulk.

References Cited (Backward Citations)

US3161628A Cited
US3007909A Cited
US3449310A Cited
US3597406A Cited
US3781257A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-02-17 1978-08-19 1979-02-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-02-17 1982-08-19 1983-02-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-02-17 1986-08-19 1987-02-18 $7700.00 Window Closed / Lapsed

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