GB1294167A - Stereospecific synthetic rubber based on 1,3-butadiene and method of producing same - Google Patents
Stereospecific synthetic rubber based on 1,3-butadiene and method of producing sameInfo
- Publication number
- GB1294167A GB1294167A GB3810770A GB3810770A GB1294167A GB 1294167 A GB1294167 A GB 1294167A GB 3810770 A GB3810770 A GB 3810770A GB 3810770 A GB3810770 A GB 3810770A GB 1294167 A GB1294167 A GB 1294167A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butadiene
- nickel
- cyclic
- chloral
- cyclohexadiene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title abstract 10
- 230000000707 stereoselective effect Effects 0.000 title abstract 2
- 229920003051 synthetic elastomer Polymers 0.000 title 1
- 239000005061 synthetic rubber Substances 0.000 title 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- -1 cyclic dienes Chemical class 0.000 abstract 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 abstract 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 abstract 2
- XMWINMVFKPHMJB-UHFFFAOYSA-N 2-Methyl-1,3-cyclohexadiene Chemical compound CC1=CCCC=C1 XMWINMVFKPHMJB-UHFFFAOYSA-N 0.000 abstract 1
- QVRBGKYLLCLCHL-UHFFFAOYSA-N 5-methylcyclopenta-1,3-diene Chemical compound CC1C=CC=C1 QVRBGKYLLCLCHL-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910000323 aluminium silicate Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 abstract 1
- XSQZBCUPXYEKRQ-UHFFFAOYSA-L nickel(2+);2,2,2-trichloroacetate Chemical compound [Ni+2].[O-]C(=O)C(Cl)(Cl)Cl.[O-]C(=O)C(Cl)(Cl)Cl XSQZBCUPXYEKRQ-UHFFFAOYSA-L 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/06—Butadiene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
1294167 Stereospecific butadiene copolymers INSTITUT NEFTEKHIMICHESKOGO SINTEZA IMENI A V TOPCHIEVA AKADEMII NAUK USSR 7 Aug 1970 38107/70 Heading C3P Synthetic rubbery copolymers comprise units derived from butadiene and one or more conjugated cyclic dienes having 5 or 6 carbon atoms in the ring, the butadiene units being at least 90% cis and the content of cyclic units being 3-20 mol. per cent. They are prepared by polymerizing a mixture of butadiene and the cyclic diene in a molar ratio of 95 : 5 to 75 : 25 by means of a catalyst comprising a #-allyl complex of nickel and an electron acceptor selected from halogenoquinones, salts of halogenoacetic acids, chloral, transition metal halides and other Lewis acids. Examples describe the copolymerization of butadiene with 1,3 - cyclohexadiene, 1,3 - cyclopentadiene, 2- methyl - 1,3 - cyclohexadiene and 1 - methyl- 2,4-cyclopentadiene in the presence of bis-(#- crotylnickel halides), #-pentenylnickel chloride or bis-(#-allylnickel bromide), and nickel trichloroacetate, chloral, chloranil, nickel chloride or an acid aluminosilicate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3810770A GB1294167A (en) | 1970-08-07 | 1970-08-07 | Stereospecific synthetic rubber based on 1,3-butadiene and method of producing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3810770A GB1294167A (en) | 1970-08-07 | 1970-08-07 | Stereospecific synthetic rubber based on 1,3-butadiene and method of producing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1294167A true GB1294167A (en) | 1972-10-25 |
Family
ID=10401232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3810770A Expired GB1294167A (en) | 1970-08-07 | 1970-08-07 | Stereospecific synthetic rubber based on 1,3-butadiene and method of producing same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1294167A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011047021A1 (en) * | 2009-10-14 | 2011-04-21 | Bridgestone Corporation | Processes for preparation of cyclic acyclic diene copolymer and rubber composition |
| US8598286B1 (en) | 2012-11-05 | 2013-12-03 | The Goodyear Tire & Rubber Company | High cis diene/phenylbutadiene copolymers prepared using a Ziegler/Natta neodymium catalyst |
| US8816032B1 (en) | 2013-05-24 | 2014-08-26 | The Goodyear Tire & Rubber Company | Copolymer of conjugated diene and 1-vinylcycloalkene |
-
1970
- 1970-08-07 GB GB3810770A patent/GB1294167A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011047021A1 (en) * | 2009-10-14 | 2011-04-21 | Bridgestone Corporation | Processes for preparation of cyclic acyclic diene copolymer and rubber composition |
| CN102666596A (en) * | 2009-10-14 | 2012-09-12 | 株式会社普利司通 | Processes for preparation of cyclic acyclic diene copolymer and rubber composition |
| CN102666596B (en) * | 2009-10-14 | 2014-04-02 | 株式会社普利司通 | Processes for preparation of cyclic acyclic diene copolymer and rubber composition |
| US8701728B2 (en) | 2009-10-14 | 2014-04-22 | Bridgestone Corporation | Processes for preparation of cyclic and acyclic diene copolymer and rubber composition |
| RU2543376C2 (en) * | 2009-10-14 | 2015-02-27 | Бриджстоун Корпорейшн | Method of obtaining copolymer of cyclic and acyclic diene and rubber mixture |
| US9056928B2 (en) | 2009-10-14 | 2015-06-16 | Bridgestone Corporation | Processes for preparation of cyclic and acyclic diene copolymer and rubber composition |
| US8598286B1 (en) | 2012-11-05 | 2013-12-03 | The Goodyear Tire & Rubber Company | High cis diene/phenylbutadiene copolymers prepared using a Ziegler/Natta neodymium catalyst |
| US8816032B1 (en) | 2013-05-24 | 2014-08-26 | The Goodyear Tire & Rubber Company | Copolymer of conjugated diene and 1-vinylcycloalkene |
| EP2805833A1 (en) | 2013-05-24 | 2014-11-26 | The Goodyear Tire & Rubber Company | Copolymer of conjugated diene and 1-vinylcycloalkene and method of making thereof |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |