GB1255764A - A process for the preparation of living polymers - Google Patents
A process for the preparation of living polymersInfo
- Publication number
- GB1255764A GB1255764A GB00907/70A GB1090770A GB1255764A GB 1255764 A GB1255764 A GB 1255764A GB 00907/70 A GB00907/70 A GB 00907/70A GB 1090770 A GB1090770 A GB 1090770A GB 1255764 A GB1255764 A GB 1255764A
- Authority
- GB
- United Kingdom
- Prior art keywords
- styrene
- butadiene
- methyl styrene
- monomer
- initiator
- 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
- 229920000642 polymer Polymers 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 6
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 abstract 5
- 239000003999 initiator Substances 0.000 abstract 5
- 239000000178 monomer Substances 0.000 abstract 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 4
- -1 naphtha Substances 0.000 abstract 4
- 239000000376 reactant Substances 0.000 abstract 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 150000001993 dienes Chemical class 0.000 abstract 3
- 239000003085 diluting agent Substances 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 150000002430 hydrocarbons Chemical class 0.000 abstract 3
- 239000003208 petroleum Substances 0.000 abstract 3
- 239000011734 sodium Substances 0.000 abstract 3
- 229910052708 sodium Inorganic materials 0.000 abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 3
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 abstract 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- 239000004305 biphenyl Substances 0.000 abstract 2
- 235000010290 biphenyl Nutrition 0.000 abstract 2
- 239000001569 carbon dioxide Substances 0.000 abstract 2
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002879 Lewis base Substances 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229920001400 block copolymer Polymers 0.000 abstract 1
- 229910052792 caesium Inorganic materials 0.000 abstract 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 150000001924 cycloalkanes Chemical class 0.000 abstract 1
- 150000001925 cycloalkenes Chemical class 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 150000007527 lewis bases Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 abstract 1
- 229910052701 rubidium Inorganic materials 0.000 abstract 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 abstract 1
- 235000015096 spirit Nutrition 0.000 abstract 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08F240/00—Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins
-
- 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and 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
- C08F36/04—Homopolymers and 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
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
- C08F4/12—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of boron, aluminium, gallium, indium, thallium or rare earths
-
- 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
- C08F8/00—Chemical modification by after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
Abstract
1,255,764. Polymerization. NIPPON SODA CO. Ltd. 6 March, 1970 [11 March, 1969; 27 March, 1969], No. 10907/70. Heading C3P. A process for the preparation of living polymers employing a tubular reactor having an initiator inlet, reactant outlet and a plurality of monomer inlets and equipped with cooling means, the reactor being such as to provide a residence time of 20 minutes to 2 hours, a heat transfer surface to maintain the reactants at -20 to -80‹ C. and a rate of reactant flow of 0.1 to 3 metres per second, comprises continuously feeding initiator solution containing a Lewis base and dispersed alkali metal or complex thereof with conjugated diolefins, polynuclear or condensed ring aromatic compounds, styrene, α-methyl styrene or mixtures thereof through the initiator inlet, feeding diluted monomer containing at most 70 weight per cent of conjugated diolefins and aliphatic or cycloaliphatic liquid hydrocarbon diluent through the monomer inlets while keeping the reactants at a temperature of -20 to -80‹ C. The monomer may comprise butadiene or butadiene containing fractions from cracked petroleum, optionally in admixture with comonomers such as styrene, α-methyl styrene, methoxystyrene, methacrylates, acrylates and acrylonitrile. The diluent may be C 4-8 alkanes and alkenes, C 5 and C 6 cycloalkanes and cycloalkenes, petroleum ether, gasoline, naphtha, kerosene or mineral spirits. The initiator may comprise an ether, acetal or t-amine, together with lithium, sodium, potassium, rubidium or caesium which may be complexed with or activated by condensed or non-condensed ring polynuclear hydrocarbons, diaryl ketones, conjugated vinyl heterocyclic compounds, conjugated diolefins, styrene or α- methyl styrene. The living polymer products may be treated to introduce terminal functional groups by reacting with electrophilic reagents, e.g. oxygen, alkylene oxides, formaldehyde, carbon dioxide, alkylene sulphides or carbon disulphide. Block copolymers may be prepared by introducing different monomers at successive inlets. Many examples are given describing the polymerization of (1, 3, 4 and 10) butadiene, mixtures thereof with (2, 7 and 10) styrene, butadiene followed by (5) α-methyl styrene, (6 and 7) cracked petroleum C 4 fractions together with (8) styrene, and (10) isoprene in hydrocarbon diluents in the presence of initiators formed from tetrahydrofuran, sodium and (1, 3, 4 and 6) butadiene, (2) o-diphenyl benzene together with (8) butadiene (5 and 7) α-methyl styrene and (9) biphenyl; from sodium and (10) tetrahydrofuran and dimethyl ether or dioxane and biphenyl; and from tetrahydro furan and (10) lithium and o-diphenyl benzene or potassium and naphthalene; and the treatment of the products with water, ethylene oxide, propylene oxide, methanol or carbon dioxide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1803069 | 1969-03-11 | ||
| JP2274469 | 1969-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1255764A true GB1255764A (en) | 1971-12-01 |
Family
ID=26354641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB00907/70A Expired GB1255764A (en) | 1969-03-11 | 1970-03-06 | A process for the preparation of living polymers |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2011561A1 (en) |
| FR (1) | FR2034825A1 (en) |
| GB (1) | GB1255764A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007028749A1 (en) * | 2005-09-07 | 2007-03-15 | Basf Se | Polymerization method |
| CN105377901A (en) * | 2013-07-17 | 2016-03-02 | 旭化成化学株式会社 | Polymer manufacturing method |
| EP3023440A4 (en) * | 2013-07-17 | 2016-07-13 | Asahi Kasei Chemicals Corp | PROCESS FOR PRODUCING POLYMER |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5645923B2 (en) * | 1973-02-12 | 1981-10-29 | ||
| US4764572A (en) * | 1985-07-23 | 1988-08-16 | Shell Oil Company | Anionic polymerization process |
-
1970
- 1970-03-06 GB GB00907/70A patent/GB1255764A/en not_active Expired
- 1970-03-11 FR FR7008752A patent/FR2034825A1/fr not_active Withdrawn
- 1970-03-11 DE DE19702011561 patent/DE2011561A1/de active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007028749A1 (en) * | 2005-09-07 | 2007-03-15 | Basf Se | Polymerization method |
| CN105377901A (en) * | 2013-07-17 | 2016-03-02 | 旭化成化学株式会社 | Polymer manufacturing method |
| EP3023440A4 (en) * | 2013-07-17 | 2016-07-13 | Asahi Kasei Chemicals Corp | PROCESS FOR PRODUCING POLYMER |
| EP3023439A4 (en) * | 2013-07-17 | 2016-07-20 | Asahi Kasei Chemicals Corp | PROCESS FOR PRODUCING POLYMER |
| EP3023439B1 (en) | 2013-07-17 | 2018-02-07 | Asahi Kasei Kabushiki Kaisha | Method for producing polymer |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2034825A1 (en) | 1970-12-18 |
| DE2011561A1 (en) | 1970-09-17 |
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