Patent US4195674A successfully refreshed from Google Patents.
Patent US4537939A successfully refreshed from Google Patents.
US4537939A
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US
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Process for production of polymers having increased 1,2-microstructure
Assignee: Bridgestone Firestone Inc
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Filing: 1984-06-04
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Granted: 1985-08-27
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Expires: 2004-06-04
Abstract
Abstract A process and catalyst system is disclosed herein for the preparation of (co)polymers having a 1,2-microstructure of between about 20 and about 65 percent. These (co)polymers are prepared in a hydrocarbon or non-polar solvent from a monomer system which contains at least one 1,3-diene monomer. The catalyst system which is employed in the production of the (co)polymer is a combination of an anionic initiator based on lithium and a phosphine oxide modifier which is substituted with three saturated heterocyclic rings, each hetero ring containing one nitrogen atom and either four, five or six carbon atoms.
Inventors
- 👤 James E. Hall
- 👤 Donald N. Schulz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 18:38
CPC Classifications
C; C08; C08F; C08F36/00; C08F36/02; C08F36/04
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
211 words
A process for the preparation of a homopolymer of a 1,3-diene monomer said homopolymer containing a 1,2-microstructure ranging between about 20 and about 65 percent which process comprises polymerizing said 1,3-diene monomer in an in inert non-polar solvent system in the presence of a catalytically effective amount of a catalyst comprising: (a) an anionic initiator based on lithium, said anionic initiator being selected from the group consisting of organolithium catalysts having the formula R(Li) x wherein R represents a hydrocarbyl radical of 1 to 20 carbon atoms per R group and x is an integer of 1-4, phenyllithium, naphthyllithium, 4-butylphenyllithium, p-tolyllithium, 4-phenylbutyllithium, 4-butylcyclohexyllithium, 4-cyclohexylbutyllithium, 1,4-dilithiobutane, 1,10-dilithiodecane, 1,20-dilithioeicosane, 1,4-dilithionaphthalene, 9,10-dilithioanthracene, 1,2-dilithio-1,2-diphenylethane, 1,3,5-trilithiopentane, 1,5,15-trilithioeicosane, 1,3,5-trilithiocyclohexane, 1,3,5,8-tetralithiodecane, 1,5,10,20-tetralithioeicosane, 1,2,4,6-tetralithiocyclohexane, 4,4'-dilithiobiphenyl, lithium dialkyl amines, lithium dialkyl phosphines, lithium alkyl aryl phosphines and lithium diaryl phosphines, and (b) a phosphine oxide modifier represented by the structural formula: ##STR2## wherein x represents an integer of 3, 4 or 5, in which the molar ratio of the anionic initiator (a) to the phosphine oxide modifier (b) ranges between about 1.0/0.1 to about 1.0/10.0 in which the temperature of polymerization initiation is at least 0° C. and in which the millimoles of the anionic initiator per 100 grams of the 1,3-diene monomer ranges between about 0.2 and about 100.
Claim 2
Dependent Claim
211 words
A process for the preparation of a homopolymer of a 1,3-diene monomer said homopolymer containing a 1,2-microstructure ranging between about 20 and about 65 percent which process comprises polymerizing said 1,3-diene monomer in an in inert non-polar solvent system in the presence of a catalytically effective amount of a catalyst comprising: (a) an anionic initiator based on lithium, said anionic initiator being selected from the group consisting of organolithium catalysts having the formula R(Li) x wherein R represents a hydrocarbyl radical of 1 to 20 carbon atoms per R group and x is an integer of 1-4, phenyllithium, naphthyllithium, 4-butylphenyllithium, p-tolyllithium, 4-phenylbutyllithium, 4-butylcyclohexyllithium, 4-cyclohexylbutyllithium, 1,4-dilithiobutane, 1,10-dilithiodecane, 1,20-dilithioeicosane, 1,4-dilithionaphthalene, 9,10-dilithioanthracene, 1,2-dilithio-1,2-diphenylethane, 1,3,5-trilithiopentane, 1,5,15-trilithioeicosane, 1,3,5-trilithiocyclohexane, 1,3,5,8-tetralithiodecane, 1,5,10,20-tetralithioeicosane, 1,2,4,6-tetralithiocyclohexane, 4,4'-dilithiobiphenyl, lithium dialkyl amines, lithium dialkyl phosphines, lithium alkyl aryl phosphines and lithium diaryl phosphines, and (b) a phosphine oxide modifier represented by the structural formula: ##STR2## wherein x represents an integer of 3, 4 or 5, in which the molar ratio of the anionic initiator (a) to the phosphine oxide modifier (b) ranges between about 1.0/0.1 to about 1.0/10.0 in which the temperature of polymerization initiation is at least 0° C. and in which the millimoles of the anionic initiator per 100 grams of the 1,3-diene monomer ranges between about 0.2 and about 100.
Claim 3
Dependent Claim
28 words
The process as in claim 1 wherein the phosphine oxide modifier is selected from the group consisting of tripiperidine phosphine oxide, tripyrrolidyl phosphine oxide and tri(cyclohexamethyleneamine) phosphine oxide.
Claim 4
Dependent Claim
12 words
The process as in claim 1 wherein the 1,3-diene is a butadiene.
Claim 5
Dependent Claim
12 words
The process as in claim 1 wherein the anionic initiator is n-butyllithium.
Claim 6
Dependent Claim
18 words
The process as in claim 1 wherein the homopolymer has a 1,2-microstructure ranging between 35 and 55 percent.
Claim 7
Dependent Claim
27 words
The process as in claim 1 wherein the polymerization temperature of the homopolymer is maintained in a temperature range between about 90° C. and about 160° C.
Claim 8
Dependent Claim
238 words
A process for the preparation of a copolymer formed by polymerizing: (A) 40 to 100 percent of at least one 1,3-diene monomer, and (B) 0 to 60 percent of one or more reactive monomers which are copolymerizable with said 1,3-diene monomers; in an inert non-polar solvent in the presence of a catalytically effective amount of a catalyst comprising: (a) an anionic initiator based on lithium, said anionic initiator being selected from the group consisting of organolithium catalysts having the formula R(Li) x wherein R represents a hydrocarbyl radical of 1 to 20 carbon atoms per R group and x is an integer of 1-4, phenyllithium, naphthyllithium, 4-butylphenyllithium, p-tolyllithium, 4-phenylbutyllithium, 4-butylcyclohexyllithium, 4-cyclohexylbutyl, 1,4-dilithiobutane, 1,10-dilithiodecane, 1,20-dilithioeicosane, 1,4-dilithiobenzene, 1,4-dilithionaphthalene, 9,10-dilithioanthracene, 1,2-dilithio-1,2-diphenylethane, 1,3,5-trilithiopentane, 1,5,15-trilithioeicosane, 1,3,5-trilithiocyclohexane, 1,3,5,8-tetralithiodecane, 1,5,10,20-tetralithioeicosane, 1,2,4,6-tetralithiocyclohexane, 4,4'-dilithiobiphenyl, lithium dialkyl amines, lithium dialkyl phosphines, lithium alkyl aryl phosphines and lithium diaryl phosphines, and (b) a phosphine oxide modifier represented by the structural formula: ##STR3## wherein x represents an integer of 3, 4 or 5, in which the molar ratio of the anionic initiator (a) to the phosphine oxide modifier (b) ranges between about 1.0/0.1 to about 1.0/10.0 in which the temperature of polymerization initiation is at least 0° C. and in which the millimoles of the anionic initiator per 100 grams of the (A+B) monomers ranges between about 2.0 and about 100, said copolymer containing a 1,2-microstructure in the 1,3-diene monomer contributed units ranging between about 20 and about 65 percent.
Claim 9
Dependent Claim
238 words
A process for the preparation of a copolymer formed by polymerizing: (A) 40 to 100 percent of at least one 1,3-diene monomer, and (B) 0 to 60 percent of one or more reactive monomers which are copolymerizable with said 1,3-diene monomers; in an inert non-polar solvent in the presence of a catalytically effective amount of a catalyst comprising: (a) an anionic initiator based on lithium, said anionic initiator being selected from the group consisting of organolithium catalysts having the formula R(Li) x wherein R represents a hydrocarbyl radical of 1 to 20 carbon atoms per R group and x is an integer of 1-4, phenyllithium, naphthyllithium, 4-butylphenyllithium, p-tolyllithium, 4-phenylbutyllithium, 4-butylcyclohexyllithium, 4-cyclohexylbutyl, 1,4-dilithiobutane, 1,10-dilithiodecane, 1,20-dilithioeicosane, 1,4-dilithiobenzene, 1,4-dilithionaphthalene, 9,10-dilithioanthracene, 1,2-dilithio-1,2-diphenylethane, 1,3,5-trilithiopentane, 1,5,15-trilithioeicosane, 1,3,5-trilithiocyclohexane, 1,3,5,8-tetralithiodecane, 1,5,10,20-tetralithioeicosane, 1,2,4,6-tetralithiocyclohexane, 4,4'-dilithiobiphenyl, lithium dialkyl amines, lithium dialkyl phosphines, lithium alkyl aryl phosphines and lithium diaryl phosphines, and (b) a phosphine oxide modifier represented by the structural formula: ##STR3## wherein x represents an integer of 3, 4 or 5, in which the molar ratio of the anionic initiator (a) to the phosphine oxide modifier (b) ranges between about 1.0/0.1 to about 1.0/10.0 in which the temperature of polymerization initiation is at least 0° C. and in which the millimoles of the anionic initiator per 100 grams of the (A+B) monomers ranges between about 2.0 and about 100, said copolymer containing a 1,2-microstructure in the 1,3-diene monomer contributed units ranging between about 20 and about 65 percent.
Claim 10
Dependent Claim
28 words
The process as in claim 7 wherein the phosphine oxide modifier is selected from the group consisting of tripiperidine phosphine oxide, tripyrrolidyl phosphine oxide and tri(cyclohexamethyleneamine) phosphine oxide.
Claim 11
Dependent Claim
17 words
The process as in claim 7 wherein the 1,3-diene is butadiene and the reactive monomer is styrene.
Claim 12
Dependent Claim
12 words
The process as in claim 7 wherein the anionic initiator is n-butyllithium.
Claim 13
Dependent Claim
26 words
The process as in claim 7 wherein the polymerization temperature for the formation of the copolymer is maintained between about 90° C. and about 160° C.
Claim 14
Dependent Claim
21 words
The process as in claim 1 wherein the molar ratio of (a) to (b) ranges from about 1.0/0.3 to about 1.0/10.0.
Claim 15
Dependent Claim
35 words
The process as recited in claim 12 wherein the molar ratio of (a) to (b) ranges from about 1.0/0.4 to about 1.0/10.0 and wherein the homoplymer has a 1,2-microstructure ranging between 35 and 55 percent.
Claim 16
Dependent Claim
22 words
The process as recited in claim 13 wherein the molar ratio of (a) to (b) ranges from about 1.0/0.4 to about 1.0/2.0.
Claim 17
Dependent Claim
30 words
The process as recited in claim 14 wherein the phosphine oxide modifier is selected from the group consisting of tripiperidine phosphine oxide, tripyrrolidyl phosphine oxide and tri(cyclohexamethylene amine) phosphine oxide.
Claim 18
Dependent Claim
26 words
The process are recited in claim 15 wherein the phosphine oxide modifier is selected from the group consisting of tripiperidine phosphine oxide and tripyrrolidyl phosphine oxide.
Claim 19
Dependent Claim
20 words
The process as recited in claim 16 wherein the 1,3-diene is a butadiene and wherein the anionic initiator is n-butyllithium
Claim 20
Dependent Claim
21 words
The process as recited in claim 7 wherein the molar ratio of (a) to (b) ranges from 1.0/0.1 to about 1.0/2.0.
Claim 21
Dependent Claim
43 words
The process as recited in claim 18 wherein the phosphine oxide modifier is selected from the group consisting of tripiperidine phosphine oxide, tripyrrolidyl phosphine oxide and tri(cyclohexamethylene amine) phosphine oxide and wherein the 1,3-diene is a butadiene and the reactive monomer is styrene.
Claim 22
Dependent Claim
34 words
The process as recited in claim 19 wherein the phosphine oxide modifier is tripiperidine phosphine oxide, the anionic initiator is n-butyllithium and the molar ratio of anionic initiator to phosphine oxide modifier is 1.0/0.5.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-08-26 | 1989-02-25 | 1989-08-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-26 | 1993-02-25 | 1993-08-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-26 | 1997-02-25 | 1997-08-27 | $7700.00 | Window Closed / Lapsed |