CA1281451C - Copolymeres a blocs et un procede pour leur preparation - Google Patents
Copolymeres a blocs et un procede pour leur preparationInfo
- Publication number
- CA1281451C CA1281451C CA000477515A CA477515A CA1281451C CA 1281451 C CA1281451 C CA 1281451C CA 000477515 A CA000477515 A CA 000477515A CA 477515 A CA477515 A CA 477515A CA 1281451 C CA1281451 C CA 1281451C
- Authority
- CA
- Canada
- Prior art keywords
- equal
- less
- alpha
- block
- propylene
- 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 - Fee Related
Links
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 claims abstract description 19
- -1 vinyl aromatic compound Chemical class 0.000 claims abstract description 19
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 12
- 239000004743 Polypropylene Substances 0.000 claims abstract description 11
- 229920001155 polypropylene Polymers 0.000 claims abstract description 10
- 150000001993 dienes Chemical class 0.000 claims abstract description 8
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 8
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 5
- 229940126062 Compound A Drugs 0.000 claims abstract description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002243 precursor Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 125000001979 organolithium group Chemical group 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims description 2
- XZKRXPZXQLARHH-XVNBXDOJSA-N [(1e)-buta-1,3-dienyl]benzene Chemical compound C=C\C=C\C1=CC=CC=C1 XZKRXPZXQLARHH-XVNBXDOJSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 230000007704 transition Effects 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 229910001507 metal halide Inorganic materials 0.000 claims 1
- 150000005309 metal halides Chemical class 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 229920000428 triblock copolymer Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910021552 Vanadium(IV) chloride Inorganic materials 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001868 water Inorganic materials 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8404824A FR2562079B1 (fr) | 1984-03-28 | 1984-03-28 | Copolymeres a blocs et un procede pour leur fabrication |
| FR84/04.824 | 1984-03-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1281451C true CA1281451C (fr) | 1991-03-12 |
Family
ID=9302550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000477515A Expired - Fee Related CA1281451C (fr) | 1984-03-28 | 1985-03-26 | Copolymeres a blocs et un procede pour leur preparation |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS6112712A (en, 2012) |
| BE (1) | BE902035A (en, 2012) |
| CA (1) | CA1281451C (en, 2012) |
| CH (1) | CH662574A5 (en, 2012) |
| DE (1) | DE3510624A1 (en, 2012) |
| ES (1) | ES8603522A1 (en, 2012) |
| FR (1) | FR2562079B1 (en, 2012) |
| GB (1) | GB2156368B (en, 2012) |
| GR (1) | GR850760B (en, 2012) |
| IE (1) | IE58344B1 (en, 2012) |
| IT (1) | IT1182724B (en, 2012) |
| LU (1) | LU85818A1 (en, 2012) |
| NL (1) | NL8500919A (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0687914B2 (ja) * | 1991-09-21 | 1994-11-09 | ジューキ株式会社 | 上糸供給装置 |
| JP2620442B2 (ja) * | 1991-09-21 | 1997-06-11 | ジューキ 株式会社 | 上糸供給装置 |
| EP3363832B1 (en) * | 2015-10-16 | 2023-01-25 | Bridgestone Corporation | Multi-component copolymer, rubber composition, crosslinked rubber composition, rubber product, and tire |
| EP3363826A4 (en) * | 2015-10-16 | 2019-03-13 | Bridgestone Corporation | MULTI-COMPONENT COPOLYMER, RESIN COMPOSITION, RETICULATED RESIN COMPOSITION, AND ARTICLE |
| WO2017064862A1 (ja) * | 2015-10-16 | 2017-04-20 | 株式会社ブリヂストン | 多元共重合体、ゴム組成物、架橋ゴム組成物、及びゴム物品 |
| JP6637716B2 (ja) * | 2015-10-16 | 2020-01-29 | 株式会社ブリヂストン | 多元共重合体、ゴム組成物、架橋ゴム組成物及びゴム物品 |
| JP6602151B2 (ja) * | 2015-10-16 | 2019-11-06 | 株式会社ブリヂストン | 多元共重合体、ゴム組成物、架橋ゴム組成物、及びゴム物品 |
| JP6602150B2 (ja) | 2015-10-16 | 2019-11-06 | 株式会社ブリヂストン | 多元共重合体、ゴム組成物、架橋ゴム組成物、及びゴム物品 |
| JP7213014B2 (ja) * | 2015-10-16 | 2023-01-26 | 株式会社ブリヂストン | 多元共重合体、ゴム組成物、架橋ゴム組成物及びゴム物品 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3418394A (en) * | 1966-01-07 | 1968-12-24 | Phillips Petroleum Co | Process for making block copolymers of conjugated dienes and vinyl-substituted aromatics |
| US3931126A (en) * | 1967-10-04 | 1976-01-06 | Phillips Petroleum Company | Modification of conjugated diene polymers by treatment with organolithium and n,n,n',n'-tetramethylalkylenediamine compounds |
| CH499644A (de) * | 1969-11-21 | 1970-11-30 | Fischer Ag Brugg Georg | Schussgarnschneidvorrichtung an einer Webmaschine |
| US4122134A (en) * | 1974-02-13 | 1978-10-24 | Sumitomo Chemical Company, Limited | Method for producing transparent block copolymer resin |
| US4208356A (en) * | 1974-09-17 | 1980-06-17 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing mixture of block copolymers |
| US3992483A (en) * | 1975-09-25 | 1976-11-16 | Phillips Petroleum Company | Promoters in the polymerization of monovinyl-aromatic compounds with primary lithium initiators |
| US4107238A (en) * | 1976-01-22 | 1978-08-15 | Exxon Research & Engineering Co. | Graft copolymerization process |
| DE2938658A1 (de) * | 1979-09-25 | 1981-04-09 | Basf Ag, 6700 Ludwigshafen | Loesungen bifunktioneller organolithiumverbindungen in nichtpolaren organischen kohlenwasserstoffen als loesungsmittel, verfahren zur herstellung solcher loesungen und deren verwendung |
| DE3309748A1 (de) * | 1982-07-23 | 1984-03-01 | Veb Chemische Werke Buna, Ddr 4212 Schkopau | Verfahren zur herstellung mehrfunktioneller polymerisationsinitiatoren |
-
1984
- 1984-03-28 FR FR8404824A patent/FR2562079B1/fr not_active Expired
-
1985
- 1985-03-12 CH CH1109/85A patent/CH662574A5/fr not_active IP Right Cessation
- 1985-03-18 ES ES541366A patent/ES8603522A1/es not_active Expired
- 1985-03-20 LU LU85818A patent/LU85818A1/fr unknown
- 1985-03-23 JP JP60059352A patent/JPS6112712A/ja active Pending
- 1985-03-23 DE DE19853510624 patent/DE3510624A1/de not_active Ceased
- 1985-03-25 IT IT47857/85A patent/IT1182724B/it active
- 1985-03-26 GB GB08507762A patent/GB2156368B/en not_active Expired
- 1985-03-26 CA CA000477515A patent/CA1281451C/fr not_active Expired - Fee Related
- 1985-03-27 IE IE77785A patent/IE58344B1/en not_active IP Right Cessation
- 1985-03-27 GR GR850760A patent/GR850760B/el unknown
- 1985-03-27 BE BE0/214721A patent/BE902035A/fr not_active IP Right Cessation
- 1985-03-28 NL NL8500919A patent/NL8500919A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB8507762D0 (en) | 1985-05-01 |
| FR2562079B1 (fr) | 1986-08-29 |
| JPS6112712A (ja) | 1986-01-21 |
| IT8547857A0 (it) | 1985-03-25 |
| FR2562079A1 (fr) | 1985-10-04 |
| CH662574A5 (fr) | 1987-10-15 |
| IE58344B1 (en) | 1993-09-08 |
| DE3510624A1 (de) | 1985-11-21 |
| IT8547857A1 (it) | 1986-09-25 |
| GB2156368B (en) | 1987-10-28 |
| GB2156368A (en) | 1985-10-09 |
| NL8500919A (nl) | 1985-10-16 |
| IE850777L (en) | 1985-09-28 |
| LU85818A1 (fr) | 1985-12-12 |
| BE902035A (fr) | 1985-09-27 |
| ES541366A0 (es) | 1985-12-16 |
| ES8603522A1 (es) | 1985-12-16 |
| GR850760B (en, 2012) | 1985-11-25 |
| IT1182724B (it) | 1987-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |