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US3935180A Expired / Lapsed US ⏱️ 0.0 years remaining

Polybutadiene and process for producing same

Assignee: Ube Corp
•
Filing: 1973-08-31
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Granted: 1976-01-27
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Expires: 1993-08-31
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Abstract

Abstract A process for producing a polybutadiene is provided wherein, first, 1,3-butadiene is polymerized in the presence of a particular cis-1,4-polymerization catalyst and subsequently, the polymerization is continued in the presence of a particular 1,2-polymerization catalyst. The resulting polybutadiene is characterized as containing 2 to 40% of the 1,2-structure, the melting point of the 1,2-structure portion being 110 DEG to 215 DEG C, and containing 60 to 98% of the cis-1,4-structure and having an intrinsic viscosity [ eta ] of 0.9 to 8 in tetraline at 135 DEG C. A vulcanized product of the polybutadiene is characterized as possessing improved tear strength, flex-crack resistance and tensile strength.

Inventors

  • 👤 Shotaro Sugiura
  • 👤 Tetsuro Matsuura
  • 👤 Haruo Ueno
  • 👤 Minoru Kono
  • 👤 Hideo Ishikawa
  • 👤 Thunehiko Tokutomi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 01:26
CPC Classifications
C; C08; C08F; C08F136/00; C08F136/02; C08F136/04; C08F136/06

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 763 words
A process for the production of polybutadiene consisting of 2-40% of the 1,2-cis structure, 60-98% of the cis-1,4-structure and not more than 1.5% of the trans-1,4-structure which comprises the two successive steps of: first, polymerizing for a period of time ranging between a period of ten minutes and 10 hours, 1,3-butadiene in an inert organic solvent in the presence of a cis-1,4-polymerization catalyst consisting essentially of a. a cobalt component selected from the group consisting of (a 1 ) a cobalt compound and (a 2 ) a material formed by electrochemically depositing metallic cobalt on metallic zinc, and b. a halogen-containing organoaluminum compound represented by the formula wherein R is an alkyl or cycloalkyl group having 1 to 6 carbon atoms or a phenyl group, X is a halogen atom and n is a positive number in the range of 1.5 to 2.0 thereby forming cis-1,4-polybutadiene, and secondly, without deactivating the remaining cis-1,4-polymerization catalyst and with the addition or no addition of 1,3-butadiene and/or an inert organic solvent to the polymerization system, effecting the 1,2-polymerization of 1,3-butadiene, (A) in the case where the following component (a') is not the same as component (a) of the cis-1,4-polymerization catalyst employed, by adding thereto, without deactivating the remaining cis-1,4-polymerization catalyst, a 1,2-polymerization catalyst comprising a'. a cobalt component selected from the group consisting of (a' 1 ) a cobalt compound and (a' 2 ) a material formed by electrochemically depositing metallic cobalt on metallic zinc, b'. an organoaluminum compound represented by the formula AlR.sub.3 ( 2) wherein R represents the group defined hereinbefore, and c'. carbon disulfide, when the component (a') is not the same as the component (a) of the cis-1,4-polymerization catalyst employed, or, B. in the case where the component (a') is the same as the component (a) of the cis-1,4-polymerization catalyst employed, by adding to the polymerization system, without deactivating the remaining cis-1,4-polymerization catalyst, either (B1) all the components of said 1,2-polymerization catalyst or (B2) the components of said 1,2-polymerization catalyst except component (a') when the component (a') is the same as the component (a) of said cis-1,4-polymerization catalyst employed, the aforesaid 1,2-polymerization being conducted for a period of time varying between ten minutes and ten hours, thereby forming the desired polybutadiene product, in which said cobalt compound of (a 1 ) and (a' 1 ) is a member selected from the group consisting of i. a cobalt salt of a carboxylic acid having 6 to 10 carbon atoms, ii. a cobalt complex of a β-diketone represented by the formula: ##EQU3## wherein each of R 1 and R 4 is an alkyl group having 1 to 3 carbon atoms and each of R 2 and R 3 is a hydrogen atom or an alkyl group having 1 to 3 atoms, iii. a cobalt complex of a β-keto acid ester represented by the formula ##EQU4## wherein R 1 , R 2 , R 3 and R 4 are as defined in preceding formula (3), and (iv) a cobalt halide complex prepared from a cobalt halide represented by the formula CoXn wherein X is a halogen atom and n is 2 or 3 and a ligand capable of forming a complex in coordination with the cobalt halide, selected from the group consisting of tertiary amines, alcohols, tertiary phosphines, ketones and N,N-dialkylamides, said cis-1,4-polymerization catalyst containing 0.002 to 50 millimoles of the cobalt compound (a 1 ) and 0.2 to 200 millimoles of the halogen-containing organoaluminum compound (b), per each mole of 1,3-butadiene, and the molar ratio (Al/Co) of the halogen-containing organoaluminum compound (b) to the cobalt compound (a 1 ) being 5 to 500, or containing 0.025 to 5 g of the material (a 2 ) formed by electrochemically depositing metallic cobalt on metallic zinc per 100 g of 1,3-butadiene and 0.1 to 5 times the weight of the material (a 2 ), of the halogen-containing organoaluminum compound (b), and said 1,2-polymerization catalyst containing 0.001 to 10 millimoles of the cobalt compound (a' 1 ), 0.1 to 100 millimoles of the organoaluminum compound (b') and 0.001 to 20 millimoles of carbon disulfide (c'), per each mole of 1,3-butadiene, and the molar ratio (Al/Co) of the organoaluminum compound (b') to the cobalt compound (a' 1 ) being 5 to 500, or containing 0.05 to 10 g of the material (a' 2 ) formed by electrochemically depositing metallic cobalt on metallic zinc per 100 g of 1,3-butadiene, 0.1 to 5 times the weight of the material (a' 2 ), of the organoaluminum compound (b') and 0.001 to 20 millimoles of carbon disulfide (c') per mole of 1,3-butadiene.
Claim 2
Dependent Claim 763 words
A process for the production of polybutadiene consisting of 2-40% of the 1,2-cis structure, 60-98% of the cis-1,4-structure and not more than 1.5% of the trans-1,4-structure which comprises the two successive steps of: first, polymerizing for a period of time ranging between a period of ten minutes and 10 hours, 1,3-butadiene in an inert organic solvent in the presence of a cis-1,4-polymerization catalyst consisting essentially of a. a cobalt component selected from the group consisting of (a 1 ) a cobalt compound and (a 2 ) a material formed by electrochemically depositing metallic cobalt on metallic zinc, and b. a halogen-containing organoaluminum compound represented by the formula wherein R is an alkyl or cycloalkyl group having 1 to 6 carbon atoms or a phenyl group, X is a halogen atom and n is a positive number in the range of 1.5 to 2.0 thereby forming cis-1,4-polybutadiene, and secondly, without deactivating the remaining cis-1,4-polymerization catalyst and with the addition or no addition of 1,3-butadiene and/or an inert organic solvent to the polymerization system, effecting the 1,2-polymerization of 1,3-butadiene, (A) in the case where the following component (a') is not the same as component (a) of the cis-1,4-polymerization catalyst employed, by adding thereto, without deactivating the remaining cis-1,4-polymerization catalyst, a 1,2-polymerization catalyst comprising a'. a cobalt component selected from the group consisting of (a' 1 ) a cobalt compound and (a' 2 ) a material formed by electrochemically depositing metallic cobalt on metallic zinc, b'. an organoaluminum compound represented by the formula AlR.sub.3 ( 2) wherein R represents the group defined hereinbefore, and c'. carbon disulfide, when the component (a') is not the same as the component (a) of the cis-1,4-polymerization catalyst employed, or, B. in the case where the component (a') is the same as the component (a) of the cis-1,4-polymerization catalyst employed, by adding to the polymerization system, without deactivating the remaining cis-1,4-polymerization catalyst, either (B1) all the components of said 1,2-polymerization catalyst or (B2) the components of said 1,2-polymerization catalyst except component (a') when the component (a') is the same as the component (a) of said cis-1,4-polymerization catalyst employed, the aforesaid 1,2-polymerization being conducted for a period of time varying between ten minutes and ten hours, thereby forming the desired polybutadiene product, in which said cobalt compound of (a 1 ) and (a' 1 ) is a member selected from the group consisting of i. a cobalt salt of a carboxylic acid having 6 to 10 carbon atoms, ii. a cobalt complex of a β-diketone represented by the formula: ##EQU3## wherein each of R 1 and R 4 is an alkyl group having 1 to 3 carbon atoms and each of R 2 and R 3 is a hydrogen atom or an alkyl group having 1 to 3 atoms, iii. a cobalt complex of a β-keto acid ester represented by the formula ##EQU4## wherein R 1 , R 2 , R 3 and R 4 are as defined in preceding formula (3), and (iv) a cobalt halide complex prepared from a cobalt halide represented by the formula CoXn wherein X is a halogen atom and n is 2 or 3 and a ligand capable of forming a complex in coordination with the cobalt halide, selected from the group consisting of tertiary amines, alcohols, tertiary phosphines, ketones and N,N-dialkylamides, said cis-1,4-polymerization catalyst containing 0.002 to 50 millimoles of the cobalt compound (a 1 ) and 0.2 to 200 millimoles of the halogen-containing organoaluminum compound (b), per each mole of 1,3-butadiene, and the molar ratio (Al/Co) of the halogen-containing organoaluminum compound (b) to the cobalt compound (a 1 ) being 5 to 500, or containing 0.025 to 5 g of the material (a 2 ) formed by electrochemically depositing metallic cobalt on metallic zinc per 100 g of 1,3-butadiene and 0.1 to 5 times the weight of the material (a 2 ), of the halogen-containing organoaluminum compound (b), and said 1,2-polymerization catalyst containing 0.001 to 10 millimoles of the cobalt compound (a' 1 ), 0.1 to 100 millimoles of the organoaluminum compound (b') and 0.001 to 20 millimoles of carbon disulfide (c'), per each mole of 1,3-butadiene, and the molar ratio (Al/Co) of the organoaluminum compound (b') to the cobalt compound (a' 1 ) being 5 to 500, or containing 0.05 to 10 g of the material (a' 2 ) formed by electrochemically depositing metallic cobalt on metallic zinc per 100 g of 1,3-butadiene, 0.1 to 5 times the weight of the material (a' 2 ), of the organoaluminum compound (b') and 0.001 to 20 millimoles of carbon disulfide (c') per mole of 1,3-butadiene.
Claim 3
Dependent Claim 101 words
A process according to claim 1, wherein said 1,2-polymerization catalyst comprises, in addition to the cobalt component (a'), the organoaluminum compound (b') and carbon disulfide (c'), a nitrile compound (d') represented by the formula R'(CH).sub.m ( 5) wherein R' is an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms and m is 1 or 2, in an amount such that the molar ratio [R'(CN) m /AlR 3 ] of the nirile compound (d') to the organoaluminum compound (b') is 0.1 to 30.
Claim 4
Dependent Claim 35 words
A process according to claim 1, wherein both the cis-1,4-polymerization and the 1,2-polymerization are performed at a temperature of -20° to 80°C under atmospheric pressure or a high pressure for 10 minutes to 10 hours.
Claim 5
Dependent Claim 33 words
A process according to claim 1, wherein said cis-1,4-polybutadiene formed by the cis-1,4-polymerization contains 90 to 100% of cis-1,4-structure and has an intrinsic viscosity [η] of 1.5 to 8 in toluene at 30°C.
Claim 6
Dependent Claim 23 words
A process according to claim 1, wherein the final polybutadiene has an intrinsic viscosity [η] of 0.9 to 8 in tetraline at 135°C.
Claim 7
Dependent Claim 52 words
A polybutadiene characterized by containing 2 to 40% of the 1,2-structure, a melting point of which structure portion is 110° to 215°C and 60 to 98% of the cis-1,4-structure and having an intrinsic viscosity [η] of 0.9 to 8 in tetraline at 135°C, and being prepared by the process of claim 1.
Claim 8
Dependent Claim 52 words
A polybutadiene characterized by containing 5 to 25% of the 1,2-structure, a melting point of which structure portion is 160° to 215°C and 75 to 95% of the cis-1,4-structure and having an intrinsic viscosity [η] of 1.2 to 5 in tetraline at 135°C, and being prepared by the process of claim 1.
Claim 9
Dependent Claim 16 words
A rubber product prepared by reacting said polybutadiene defined in claim 6, with a vulcanizing agent.
Claim 10
Dependent Claim 16 words
A rubber product prepared by reacting said polybutadiene defined in claim 7, with a vulcanizing agent.
Claim 11
Dependent Claim 17 words
A process according to claim 1 wherein the cis-1,4-polymerization catalyst components are cobalt octoate and diethylaluminum monochloride.
Claim 12
Dependent Claim 18 words
A process according to claim 1 wherein the cis-1,4-polymerization catalyst components are cobalt naphthenate and diethyl aluminium monochloride.
Claim 13
Dependent Claim 17 words
A process according to claim 1 wherein the cis-1,4-polymerization catalyst components are cobalt octoate and dibutylaluminium monochloride.
Claim 14
Dependent Claim 17 words
A process according to claim 1 wherein the cis-1,4-polymerization catalyst components are cobalt octoate and diethylaluminium monobromide.
Claim 15
Dependent Claim 19 words
A process according to claim 1 wherein the cis-1,4-polymerization catalyst components are cobalt triacetyl acetonate and diethyl aluminium monochloride.
Claim 16
Dependent Claim 18 words
A process according to claim 1 wherein the cis-1,4-polymerization catalyst components are cobalt triacetyl acetonate and ethylaluminium sesquichloride.
Claim 17
Dependent Claim 19 words
A process according to claim 11 wherein the cis-1,4-polymerization catalyst components are cobalt chloride-pyridine complex and diethyl aluminium monochloride.

References Cited (Backward Citations)

US3300466A Cited
US3301840A Cited
US3595850A Cited
US3778424A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-01-26 1979-07-28 1980-01-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-01-26 1983-07-28 1984-01-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-01-26 1987-07-28 1988-01-27 $7700.00 Window Closed / Lapsed

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