CA1067643A - Preparation of a non-linear, elastomeric copolymer - Google Patents
Preparation of a non-linear, elastomeric copolymerInfo
- Publication number
- CA1067643A CA1067643A CA237,975A CA237975A CA1067643A CA 1067643 A CA1067643 A CA 1067643A CA 237975 A CA237975 A CA 237975A CA 1067643 A CA1067643 A CA 1067643A
- Authority
- CA
- Canada
- Prior art keywords
- block
- monoalkenyl
- polymer
- aromatic hydrocarbon
- conjugated diene
- 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
- 229920001198 elastomeric copolymer Polymers 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229920000642 polymer Polymers 0.000 claims abstract description 27
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 18
- 150000001993 dienes Chemical class 0.000 claims abstract description 18
- 239000007822 coupling agent Substances 0.000 claims abstract description 10
- 238000005859 coupling reaction Methods 0.000 claims abstract description 7
- 230000008878 coupling Effects 0.000 claims abstract description 4
- 238000010168 coupling process Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000003999 initiator Substances 0.000 claims description 16
- 229910052744 lithium Inorganic materials 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 230000001808 coupling effect Effects 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 150000002642 lithium compounds Chemical class 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 abstract description 3
- 239000004793 Polystyrene Substances 0.000 abstract description 2
- 229920003244 diene elastomer Polymers 0.000 abstract description 2
- 229920002223 polystyrene Polymers 0.000 abstract description 2
- 239000005060 rubber Substances 0.000 abstract description 2
- 238000004073 vulcanization Methods 0.000 abstract description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- -1 alkyl lithium Chemical compound 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- PCPYTNCQOSFKGG-ONEGZZNKSA-N (1e)-1-chlorobuta-1,3-diene Chemical compound Cl\C=C\C=C PCPYTNCQOSFKGG-ONEGZZNKSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- JMLPLTJXKRFQQT-UHFFFAOYSA-N 1,1,1-tribromobutane Chemical compound CCCC(Br)(Br)Br JMLPLTJXKRFQQT-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- PNLQPWWBHXMFCA-UHFFFAOYSA-N 2-chloroprop-1-ene Chemical compound CC(Cl)=C PNLQPWWBHXMFCA-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102000018361 Contactin Human genes 0.000 description 1
- 108060003955 Contactin Proteins 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- 239000006237 Intermediate SAF Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 229920001744 Polyaldehyde Polymers 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
- C08G81/022—Block or graft polymers containing only sequences of polymers of C08C or C08F containing sequences of polymers of conjugated dienes and of polymers of alkenyl aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB52826/74A GB1527226A (en) | 1974-12-06 | 1974-12-06 | Preparation of a non-linear elastomeric copolymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067643A true CA1067643A (en) | 1979-12-04 |
Family
ID=10465474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA237,975A Expired CA1067643A (en) | 1974-12-06 | 1975-10-20 | Preparation of a non-linear, elastomeric copolymer |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5947687B2 (OSRAM) |
| AU (1) | AU500161B2 (OSRAM) |
| BE (1) | BE835943A (OSRAM) |
| CA (1) | CA1067643A (OSRAM) |
| DE (1) | DE2554585C2 (OSRAM) |
| ES (1) | ES443215A1 (OSRAM) |
| FR (1) | FR2293446A1 (OSRAM) |
| GB (1) | GB1527226A (OSRAM) |
| IT (1) | IT1051029B (OSRAM) |
| NL (1) | NL182571C (OSRAM) |
| ZA (1) | ZA757620B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2550226C2 (de) * | 1975-11-08 | 1984-12-13 | Basf Ag, 6700 Ludwigshafen | Verzweigte Blockcopolymerisate und Verfahren zu ihrer Herstellung |
| JPS61171714A (ja) * | 1984-07-23 | 1986-08-02 | Japan Synthetic Rubber Co Ltd | 粘着剤組成物 |
| GB2169905A (en) * | 1984-12-13 | 1986-07-23 | Japan Synthetic Rubber Co Ltd | Conjugated diene based rubber composition |
| US5292819A (en) * | 1989-08-11 | 1994-03-08 | The Dow Chemical Company | Radial block copolymers containing butadiene endblock |
| US5399627A (en) * | 1989-08-11 | 1995-03-21 | The Dow Chemical Company | Radial styrene-isoprene-butadiene multi-armed block copolymers and compositions and articles containing block copolymers |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3639521A (en) * | 1969-04-23 | 1972-02-01 | Phillips Petroleum Co | Polar compound adjuvants for improved block polymers prepared with primary hydrocarbyllithium initiators |
-
1974
- 1974-12-06 GB GB52826/74A patent/GB1527226A/en not_active Expired
-
1975
- 1975-10-20 CA CA237,975A patent/CA1067643A/en not_active Expired
- 1975-11-26 BE BE1007032A patent/BE835943A/xx not_active IP Right Cessation
- 1975-12-02 IT IT29939/75A patent/IT1051029B/it active
- 1975-12-04 ES ES443215A patent/ES443215A1/es not_active Expired
- 1975-12-04 NL NLAANVRAGE7514129,A patent/NL182571C/xx active Search and Examination
- 1975-12-04 DE DE2554585A patent/DE2554585C2/de not_active Expired
- 1975-12-04 ZA ZA757620A patent/ZA757620B/xx unknown
- 1975-12-04 JP JP50143431A patent/JPS5947687B2/ja not_active Expired
- 1975-12-04 AU AU87267/75A patent/AU500161B2/en not_active Expired
- 1975-12-04 FR FR7537142A patent/FR2293446A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2554585A1 (de) | 1976-06-10 |
| IT1051029B (it) | 1981-04-21 |
| FR2293446A1 (fr) | 1976-07-02 |
| AU500161B2 (en) | 1979-05-10 |
| FR2293446B1 (OSRAM) | 1980-06-20 |
| AU8726775A (en) | 1977-06-09 |
| DE2554585C2 (de) | 1986-04-03 |
| NL7514129A (nl) | 1976-06-09 |
| ZA757620B (en) | 1976-11-24 |
| NL182571C (nl) | 1988-04-05 |
| JPS5947687B2 (ja) | 1984-11-21 |
| GB1527226A (en) | 1978-10-04 |
| ES443215A1 (es) | 1977-04-16 |
| JPS5182390A (en) | 1976-07-19 |
| BE835943A (nl) | 1976-05-26 |
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