← Back to Patent Explorer
US3844974A Expired / Lapsed US ⏱️ 0.0 years remaining

Catalyst for the polymerization of conjugated diolefins

Assignee: Goodyear Tire and Rubber Co
•
Filing: 1973-01-26
•
Granted: 1974-10-29
•
Expires: 1993-01-26
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract There is disclosed a method for the polymerization of butadiene or butadiene in mixture with other diolefins such as isoprene, 2ethyl butadiene, 2,3-dimethyl butadiene and the like, with a catalyst system comprising (1) an organometallic compound in which the metal is from Groups I, II and III of the Periodic System, (2) a nickel compound from the group of carboxylic acid salts of nickel, organic complex compounds of nickel or nickel carbonyls, (3) a fluorine containing compound from the group of boron trifluoride, metal fluorides and complexes thereof and (4) a compound containing a hydroperoxide group. The polymers contain a high proportion of cis 1,4 content and find use as synthetic rubbers in such products as tires and tire treads.

Inventors

  • 👤 M Throckmorton

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 08:17
CPC Classifications
C; C08; C08F; C08F36/00; C08F36/02; C08F36/04

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 17 words
A CATALYST COMPOSITION CONSISTING ESSENTIALLY OF A. AT LEAST ONE ORGANOMETAL SELECTED FROM THE GROUP CONSISTING OF
Claim 2
Dependent Claim 17 words
A CATALYST COMPOSITION CONSISTING ESSENTIALLY OF A. AT LEAST ONE ORGANOMETAL SELECTED FROM THE GROUP CONSISTING OF
Claim 3
Dependent Claim 6 words
AN OEGANOALUMINUM COMPOUND OF THE FORMULA:
Claim 4
Dependent Claim 6 words
AN OEGANOALUMINUM COMPOUND OF THE FORMULA:
Claim 5
Dependent Claim 58 words
AN ORGANOMAGNESIUM COMPOUND OF THE FORMULAE: A. RAMGXB B. R2MG OR C. RMGY WHEREIN R IS SELECTED FROM THE GROUP CONSISTING OF ALKYL, ARYL, ARYLALKYL AND ALKARYL AND X IS HALOGEN, Y IS FLUORINE AND A AND B ARE MOLE FRACTIONS WHOSE SUM EQUALS 2 WHILE THE MOLE RATIO OF A/B IS GREATER THAN 2 BUT NOT INFINITE,
Claim 6
Dependent Claim 58 words
AN ORGANOMAGNESIUM COMPOUND OF THE FORMULAE: A. RAMGXB B. R2MG OR C. RMGY WHEREIN R IS SELECTED FROM THE GROUP CONSISTING OF ALKYL, ARYL, ARYLALKYL AND ALKARYL AND X IS HALOGEN, Y IS FLUORINE AND A AND B ARE MOLE FRACTIONS WHOSE SUM EQUALS 2 WHILE THE MOLE RATIO OF A/B IS GREATER THAN 2 BUT NOT INFINITE,
Claim 7
Dependent Claim 59 words
an organomagnesium compound of the formulae: a. RaMgXb b. R2Mg or c. RMgY wherein R is selected from the group consisting of alkyl, aryl, arylalkyl and alkaryl and X is a halogen, Y is fluorine and a and b are mole fractions whose sum equals 2 while the mole ratio of a/b is greater than 2 but not infinite,
Claim 8
Dependent Claim 59 words
an organomagnesium compound of the formulae: a. RaMgXb b. R2Mg or c. RMgY wherein R is selected from the group consisting of alkyl, aryl, arylalkyl and alkaryl and X is a halogen, Y is fluorine and a and b are mole fractions whose sum equals 2 while the mole ratio of a/b is greater than 2 but not infinite,
Claim 9
Dependent Claim 38 words
A composition according to claim 1 in which the catalyst is preformed in the presence of a conjugated diolefin and the mole ratio of the conjugated diolefin to the nickel compound ranges from about 0.5/1 to about 3000/1.
Claim 10
Dependent Claim 22 words
an organozinc compound of the formula: R2Zn wherein R is selected from the group consisting of alkyl, aryl, alkaryl and arylalkyl, and
Claim 11
Dependent Claim 22 words
an organozinc compound of the formula: R2Zn wherein R is selected from the group consisting of alkyl, aryl, alkaryl and arylalkyl, and
Claim 12
Dependent Claim 6 words
AN ORGANOZINC COMPOUND OF THE FORMULA:
Claim 13
Dependent Claim 6 words
AN ORGANOZINC COMPOUND OF THE FORMULA:
Claim 14
Dependent Claim 236 words
an organolithium compound of the formulae: a. RLi or b. R''4LiAl wherein R is selected from the group consisting of alkyl, alkaryl, arylalkyl and aryl and R'' is selected from the group consisting of alkyl, alkaryl and arylalkyl, B. at least one nickel compound selected from the group consisting of nickel benzoate, nickel acetate, nickel naphthenate, bis(alpha furyl dioxime) nickel, nickel octanoate, nickel palmitate, nickel stearate, nickel acetylacetonate, bis(salicylaldehyde) ethylene diimine nickel, nickel salicaldehyde and nickel tetracarbonyl, C. a fluorine containing compound selected from the group consisting of boron trifluoride, boron trifluoride diethyl-etherate, boron trifluoride di-n-butyl-etherate, boron trifluoride ethyl acetate complex, boron trifluoride benzaldehyde complex, boron trifluoride acetone complex, boron trifluoride benzonitrile complex, boron trifluoride ethyl alcoholate, boron trifluoride phenolate, tributyltin fluoride, molybdenum hexafluoride, tungsten hexafluoride, stannic fluoride, titanium tetrafluoride, antimony trifluoride, and D. a compound containing a hydroperoxide group of the formulae: a. ROOH or b. HOOR''OOH wherein R is hydrogen or hydrocarbyl and R'' is hydrocarbylene in which the mole ratio of the organometal compound to the nickel compound ranges from about 1/1 to about 150/1, the mole ratio of the fluorine containing compound to the nickel containing compound ranges from about 3/1 to about 400/1, the mole ratio of the organometal compound to the fluorine containing compound ranges from about 0.3/1 to about 3/1 and the mole ratio of the hydroperoxide compound to the organometal compound ranges from about 0.0/1 to about 1.5/1.
Claim 15
Dependent Claim 236 words
an organolithium compound of the formulae: a. RLi or b. R''4LiAl wherein R is selected from the group consisting of alkyl, alkaryl, arylalkyl and aryl and R'' is selected from the group consisting of alkyl, alkaryl and arylalkyl, B. at least one nickel compound selected from the group consisting of nickel benzoate, nickel acetate, nickel naphthenate, bis(alpha furyl dioxime) nickel, nickel octanoate, nickel palmitate, nickel stearate, nickel acetylacetonate, bis(salicylaldehyde) ethylene diimine nickel, nickel salicaldehyde and nickel tetracarbonyl, C. a fluorine containing compound selected from the group consisting of boron trifluoride, boron trifluoride diethyl-etherate, boron trifluoride di-n-butyl-etherate, boron trifluoride ethyl acetate complex, boron trifluoride benzaldehyde complex, boron trifluoride acetone complex, boron trifluoride benzonitrile complex, boron trifluoride ethyl alcoholate, boron trifluoride phenolate, tributyltin fluoride, molybdenum hexafluoride, tungsten hexafluoride, stannic fluoride, titanium tetrafluoride, antimony trifluoride, and D. a compound containing a hydroperoxide group of the formulae: a. ROOH or b. HOOR''OOH wherein R is hydrogen or hydrocarbyl and R'' is hydrocarbylene in which the mole ratio of the organometal compound to the nickel compound ranges from about 1/1 to about 150/1, the mole ratio of the fluorine containing compound to the nickel containing compound ranges from about 3/1 to about 400/1, the mole ratio of the organometal compound to the fluorine containing compound ranges from about 0.3/1 to about 3/1 and the mole ratio of the hydroperoxide compound to the organometal compound ranges from about 0.0/1 to about 1.5/1.
Claim 16
Dependent Claim 235 words
AN ORGANOLITHIUM COMPOUND OF THE FORMULAE: A. RLI OR B. R''4LIAL WHEREIN R IS SELECTED FROM THE GROUP CONSISTING OF ALKYL, ALKARYL, ARYLALKYL AND ARYL AND R'' IS SELECTED FROM THE GROUP CONSISTING OF ALKYL, ALKARYL, AND ARYLALKYL, B. AT LEAST ONE NICKEL COMPOUND SELECTED FROM THE GROUP CONSISTING OF NICKEL BENZOATE, NICKEL ACETATE, NICKEL NAPHTHENATE, BIS(ALPHA FURYL DIOXIME) NICKEL, NICKEL OCTANOTE, NICKEL PALMITATE, NICKEL STEARATE, NICKEL ACETLACETONATE, BIS(SALICYLALDEHYDE) ETHYLENE DIIMINE NICKEL, NICKEL SALICALDEHYDE AND NICKEL TETRACARBONYL, C. A FLUORINE CONTAINING COMPOUND SELECTED FROM THE G GROUP CONSISTING OF BORON TRIFLUORIDE, BORON TTRIFLUORIDE DIETHYL-ETHERATE BORON TRIFLUORIDE DI-N-BUTYL-ETHERATE BORON TRIFLUORIDE ETHYL ACETATE COMPLEX, BORON TRIFLUORIDE BENZALDEHYDE COMPLEX, BORON TRIFLUORIDE ACETONE COMPLEX, BORON TRIFLUORIDE BENZONITRILE COMPLEX, BORON TRIFLUORIDE ETHYL ALCOHOLATE, MOLYBDENUM HEXAFLUORIDE, TUNGTRIBUTYLTIN FLUORIDE, MOLYBDENUM HEXAFLUORIDE, TUNGSTEN HEXAFLUORIDE, STANNIC FLUORIDE, TITAIUM TETRAFLUORIDE, ANTIMONY TRIFLUORIDE, AND D. A COMPOUND CONTAINING A HYDROPEROXIDE GROUP OF THE FORMULAE: A. ROOH OR B. HOOR(OCH WHEREIN R IS HYDROGEN OR HYDROCARBYL AND R'' IS HYDROCARBYLENE IN WHICH THE MOLE RATIO OF THE ORGANOMETAL COMPOUND TO THE NICKEL COMPOUND RANGES FROM ABOUT 1/1 TO ABOUT 150/1 THE MOLE RATIO OF THE FLUORINE CONTAINING COMPOUND OF THE NICKEL CONTAINING COMPOUND RANGES FROMA BOUT 3/1 TO 400/1 THE MOLE RATIO OF THE ORGANOMETAL COMPOUND TO THE FLUORINE CONTAINING COMPOUND RANGES FROM ABOUT 0,3/1 TO ABOUT 3/1 AND THE MOLE RATIO OF THE HYDROPEROXIDE COMPOUND TO THE ORGANOMETAL COMPOUND RANGES FROM ABOUT 0.0/1 TO ABOUT 1.5/1.
Claim 17
Dependent Claim 235 words
AN ORGANOLITHIUM COMPOUND OF THE FORMULAE: A. RLI OR B. R''4LIAL WHEREIN R IS SELECTED FROM THE GROUP CONSISTING OF ALKYL, ALKARYL, ARYLALKYL AND ARYL AND R'' IS SELECTED FROM THE GROUP CONSISTING OF ALKYL, ALKARYL, AND ARYLALKYL, B. AT LEAST ONE NICKEL COMPOUND SELECTED FROM THE GROUP CONSISTING OF NICKEL BENZOATE, NICKEL ACETATE, NICKEL NAPHTHENATE, BIS(ALPHA FURYL DIOXIME) NICKEL, NICKEL OCTANOTE, NICKEL PALMITATE, NICKEL STEARATE, NICKEL ACETLACETONATE, BIS(SALICYLALDEHYDE) ETHYLENE DIIMINE NICKEL, NICKEL SALICALDEHYDE AND NICKEL TETRACARBONYL, C. A FLUORINE CONTAINING COMPOUND SELECTED FROM THE G GROUP CONSISTING OF BORON TRIFLUORIDE, BORON TTRIFLUORIDE DIETHYL-ETHERATE BORON TRIFLUORIDE DI-N-BUTYL-ETHERATE BORON TRIFLUORIDE ETHYL ACETATE COMPLEX, BORON TRIFLUORIDE BENZALDEHYDE COMPLEX, BORON TRIFLUORIDE ACETONE COMPLEX, BORON TRIFLUORIDE BENZONITRILE COMPLEX, BORON TRIFLUORIDE ETHYL ALCOHOLATE, MOLYBDENUM HEXAFLUORIDE, TUNGTRIBUTYLTIN FLUORIDE, MOLYBDENUM HEXAFLUORIDE, TUNGSTEN HEXAFLUORIDE, STANNIC FLUORIDE, TITAIUM TETRAFLUORIDE, ANTIMONY TRIFLUORIDE, AND D. A COMPOUND CONTAINING A HYDROPEROXIDE GROUP OF THE FORMULAE: A. ROOH OR B. HOOR(OCH WHEREIN R IS HYDROGEN OR HYDROCARBYL AND R'' IS HYDROCARBYLENE IN WHICH THE MOLE RATIO OF THE ORGANOMETAL COMPOUND TO THE NICKEL COMPOUND RANGES FROM ABOUT 1/1 TO ABOUT 150/1 THE MOLE RATIO OF THE FLUORINE CONTAINING COMPOUND OF THE NICKEL CONTAINING COMPOUND RANGES FROMA BOUT 3/1 TO 400/1 THE MOLE RATIO OF THE ORGANOMETAL COMPOUND TO THE FLUORINE CONTAINING COMPOUND RANGES FROM ABOUT 0,3/1 TO ABOUT 3/1 AND THE MOLE RATIO OF THE HYDROPEROXIDE COMPOUND TO THE ORGANOMETAL COMPOUND RANGES FROM ABOUT 0.0/1 TO ABOUT 1.5/1.

References Cited (Backward Citations)

US3024227A Cited
US2868771A Cited
US3170905A Cited
US3432517A Cited
US3446788A Cited
US3487063A Cited
US3734900A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1977-10-28 1978-04-29 1978-10-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1981-10-28 1982-04-29 1982-10-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1985-10-28 1986-04-29 1986-10-29 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag