DE3108583C2 - - Google Patents
Info
- Publication number
- DE3108583C2 DE3108583C2 DE3108583A DE3108583A DE3108583C2 DE 3108583 C2 DE3108583 C2 DE 3108583C2 DE 3108583 A DE3108583 A DE 3108583A DE 3108583 A DE3108583 A DE 3108583A DE 3108583 C2 DE3108583 C2 DE 3108583C2
- Authority
- DE
- Germany
- Prior art keywords
- styrene
- copolymer
- butadiene
- diene component
- content
- 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 208
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 84
- 229920001577 copolymer Polymers 0.000 claims description 70
- 238000006243 chemical reaction Methods 0.000 claims description 63
- 239000000178 monomer Substances 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 39
- 238000006116 polymerization reaction Methods 0.000 claims description 36
- 150000001993 dienes Chemical class 0.000 claims description 25
- 230000008878 coupling Effects 0.000 claims description 24
- 238000010168 coupling process Methods 0.000 claims description 24
- 238000005859 coupling reaction Methods 0.000 claims description 24
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 9
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 239000007822 coupling agent Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 239000003607 modifier Substances 0.000 claims description 6
- 230000007423 decrease Effects 0.000 claims description 5
- 229920001198 elastomeric copolymer Polymers 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 230000003247 decreasing effect Effects 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 45
- 238000010586 diagram Methods 0.000 description 28
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 23
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 14
- 238000005096 rolling process Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 9
- 239000004793 Polystyrene Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 8
- 229920003048 styrene butadiene rubber Polymers 0.000 description 7
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000015271 coagulation Effects 0.000 description 5
- 238000005345 coagulation Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000009849 deactivation Effects 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- -1 lithium hydrocarbon compound Chemical class 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 2
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- QWHNJUXXYKPLQM-UHFFFAOYSA-N dimethyl cyclopentane Natural products CC1(C)CCCC1 QWHNJUXXYKPLQM-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000005049 silicon tetrachloride Substances 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- SYWDWCWQXBUCOP-UHFFFAOYSA-N benzene;ethene Chemical compound C=C.C1=CC=CC=C1 SYWDWCWQXBUCOP-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ZLPHTMMGQHNDDQ-UHFFFAOYSA-N lithium;2-methylbutane Chemical compound [Li+].CC(C)C[CH2-] ZLPHTMMGQHNDDQ-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
- IQIWJEAPUNWDLC-UHFFFAOYSA-N lithium;octane Chemical compound [Li+].CCCCCCC[CH2-] IQIWJEAPUNWDLC-UHFFFAOYSA-N 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 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
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- 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
- C08F236/10—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 with vinyl-aromatic monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
- Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Mechanical Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
- Graft Or Block Polymers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Heating, Cooling, Or Curing Plastics Or The Like In General (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8007861 | 1980-03-07 | ||
| GB8007860 | 1980-03-07 | ||
| GB8038405 | 1980-11-29 | ||
| GB8038406 | 1980-11-29 | ||
| GB8105433A GB2071117B (en) | 1980-03-07 | 1981-02-20 | Elastomers and tyres containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3108583A1 DE3108583A1 (de) | 1982-01-07 |
| DE3108583C2 true DE3108583C2 (en, 2012) | 1990-04-05 |
Family
ID=27516406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813108583 Granted DE3108583A1 (de) | 1980-03-07 | 1981-03-06 | Elastomere und reifen, welche solche elastomere enthalten |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4845154A (en, 2012) |
| JP (1) | JPH03103454A (en, 2012) |
| AT (1) | AT383131B (en, 2012) |
| AU (1) | AU539990B2 (en, 2012) |
| BR (1) | BR8101308A (en, 2012) |
| CA (1) | CA1208845A (en, 2012) |
| DE (1) | DE3108583A1 (en, 2012) |
| FI (1) | FI69634C (en, 2012) |
| FR (1) | FR2483432B1 (en, 2012) |
| IN (1) | IN155447B (en, 2012) |
| IT (1) | IT1136851B (en, 2012) |
| LU (1) | LU83194A1 (en, 2012) |
| MX (2) | MX156842A (en, 2012) |
| NL (1) | NL190018C (en, 2012) |
| SE (3) | SE453298B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2200123B (en) * | 1986-12-02 | 1990-06-13 | Shell Int Research | Elastomers and tyres containing them |
| US6372863B1 (en) * | 1999-08-12 | 2002-04-16 | The Goodyear Tire & Rubber Company | Synthesis of styrene-butadiene rubber |
| US6605680B1 (en) | 2000-04-07 | 2003-08-12 | Eastman Chemical Resins, Inc. | Low color, aromatic modified C5 hydrocarbon resins |
| JP5291858B2 (ja) * | 2004-03-16 | 2013-09-18 | 株式会社ブリヂストン | ゴム組成物及びこれを用いた空気入りタイヤ |
| JP4843917B2 (ja) * | 2004-08-06 | 2011-12-21 | Ｊｓｒ株式会社 | 共役ジエン系共重合ゴムの製造方法 |
| RU2501816C2 (ru) * | 2008-04-30 | 2013-12-20 | Стирон Юроп Гмбх | Стирол-бутадиеновые полимеры со стирольным градиентом и способы изготовления таковых |
| JP5571765B2 (ja) | 2009-03-19 | 2014-08-13 | スティロン ヨーロッパ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規なスチレンを含有するスチレンブタジエンゴム |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3094512A (en) * | 1959-12-31 | 1963-06-18 | Phillips Petroleum Co | Process for the preparation of low vinyl low trans content random copolymer |
| NL135606C (en, 2012) * | 1962-08-09 | |||
| US3402159A (en) * | 1963-12-20 | 1968-09-17 | Phillips Petroleum Co | Process for polymerizing butadiene and styrene terminated in short blocks of polystyrene |
| DE1457023A1 (de) * | 1965-11-11 | 1968-12-12 | Brodd Thure Alvar Valentin | Walzenfoermige Buerste fuer Kehrmaschinen u.dgl. |
| NL155560B (nl) * | 1966-10-03 | 1978-01-16 | Firestone Tire & Rubber Co | Werkwijze voor het copolymeriseren van butadieen met styreen, alsmede onder toepassing hiervan vervaardigde voorwerpen. |
| NL135608C (en, 2012) * | 1966-11-28 | |||
| NL134845C (en, 2012) * | 1967-02-20 | |||
| GB1231657A (en, 2012) * | 1967-07-14 | 1971-05-12 | ||
| US3594452A (en) * | 1968-02-06 | 1971-07-20 | Shell Oil Co | Polymers prepared from monolithiumterminated block copolymers and certain diesters |
| US3551392A (en) * | 1968-09-12 | 1970-12-29 | Shell Oil Co | Process for the preparation of branched conjugated diene polymers |
| JPS514940B1 (en, 2012) * | 1970-04-24 | 1976-02-16 | ||
| GB1369431A (en) * | 1971-09-02 | 1974-10-09 | Letraset International Ltd | Production of etched products |
| SU366723A1 (ru) * | 1971-09-27 | 1974-10-05 | Способ получени статистических дивинилстирольных каучуков | |
| JPS53416B2 (en, 2012) * | 1971-10-25 | 1978-01-09 | ||
| CA1017897A (en) * | 1972-03-15 | 1977-09-20 | Robert C. Smith | Transparent impact polystyrene plastics |
| IT1005994B (it) * | 1973-04-19 | 1976-09-30 | Sumitomo Chemical Co | Procedimento per la produzione di una resina copolimerica a blocchi trasparente e prodotto ottenuto |
| US3953543A (en) * | 1973-12-26 | 1976-04-27 | The Firestone Tire & Rubber Company | Polymerization process and polymer produced thereby |
| DE2410913A1 (de) * | 1974-03-07 | 1975-09-18 | Bayer Ag | Polymerisation von dienen |
| JPS5118258A (en) * | 1974-08-06 | 1976-02-13 | Koichi Kaneko | Chukokeino boorubearingu reesuno seihooyobiseihin |
| US3992561A (en) * | 1975-07-07 | 1976-11-16 | The General Tire & Rubber Company | Preparation of solution polymers |
| US4039633A (en) * | 1976-04-19 | 1977-08-02 | Phillips Petroleum Company | Coupling of alkali metal-terminated polymers |
| US4105714A (en) * | 1976-04-19 | 1978-08-08 | Phillips Petroleum Company | Coupling of alkali metal-terminated polymers |
| GB1604395A (en) * | 1977-10-08 | 1981-12-09 | Dunlop Ltd | Elastomer compositions and tyre treads comprising them |
| JPS57100112A (en) * | 1980-12-16 | 1982-06-22 | Asahi Chem Ind Co Ltd | Perfectly random styrene-butadiene copolymer rubber |
-
1981
- 1981-02-24 SE SE8101210A patent/SE453298B/sv unknown
- 1981-02-24 SE SE8101210D patent/SE8101210L/xx not_active Application Discontinuation
- 1981-03-02 FI FI810650A patent/FI69634C/fi not_active IP Right Cessation
- 1981-03-03 IN IN120/DEL/81A patent/IN155447B/en unknown
- 1981-03-03 CA CA000372169A patent/CA1208845A/en not_active Expired
- 1981-03-04 IT IT20112/81A patent/IT1136851B/it active
- 1981-03-04 MX MX186231A patent/MX156842A/es unknown
- 1981-03-06 NL NLAANVRAGE8101085,A patent/NL190018C/xx not_active IP Right Cessation
- 1981-03-06 DE DE19813108583 patent/DE3108583A1/de active Granted
- 1981-03-06 LU LU83194A patent/LU83194A1/fr unknown
- 1981-03-06 AU AU68141/81A patent/AU539990B2/en not_active Ceased
- 1981-03-06 BR BR8101308A patent/BR8101308A/pt not_active IP Right Cessation
- 1981-03-06 AT AT0104881A patent/AT383131B/de not_active IP Right Cessation
- 1981-03-06 FR FR8104490A patent/FR2483432B1/fr not_active Expired
-
1983
- 1983-08-17 US US06/524,019 patent/US4845154A/en not_active Expired - Fee Related
-
1986
- 1986-10-20 MX MX004088A patent/MX166919B/es unknown
-
1987
- 1987-04-28 SE SE8701753A patent/SE463922B/sv unknown
-
1990
- 1990-03-12 JP JP2058231A patent/JPH03103454A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE8101210L (sv) | 1981-09-08 |
| DE3108583A1 (de) | 1982-01-07 |
| SE453298B (sv) | 1988-01-25 |
| NL190018C (nl) | 1993-10-01 |
| ATA104881A (de) | 1986-10-15 |
| BR8101308A (pt) | 1981-09-08 |
| IT1136851B (it) | 1986-09-03 |
| FI69634C (fi) | 1986-03-10 |
| US4845154A (en) | 1989-07-04 |
| SE463922B (sv) | 1991-02-11 |
| AU6814181A (en) | 1981-09-10 |
| SE8701753D0 (sv) | 1987-04-28 |
| FI810650L (fi) | 1981-09-08 |
| CA1208845A (en) | 1986-07-29 |
| FI69634B (fi) | 1985-11-29 |
| AT383131B (de) | 1987-05-25 |
| JPH0543722B2 (en, 2012) | 1993-07-02 |
| MX166919B (es) | 1993-02-15 |
| FR2483432A1 (en, 2012) | 1981-12-04 |
| NL190018B (nl) | 1993-05-03 |
| AU539990B2 (en) | 1984-10-25 |
| IT8120112A0 (it) | 1981-03-04 |
| MX156842A (es) | 1988-10-07 |
| FR2483432B1 (en, 2012) | 1985-01-25 |
| LU83194A1 (fr) | 1981-10-30 |
| IN155447B (en, 2012) | 1985-02-02 |
| JPH03103454A (ja) | 1991-04-30 |
| SE8701753L (sv) | 1987-04-28 |
| NL8101085A (nl) | 1981-10-01 |
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| 8127 | New person/name/address of the applicant |
Owner name: SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V., D |
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| 8128 | New person/name/address of the agent |
Representative=s name: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DI |
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| D2 | Grant after examination | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DIPL.-PHYS. DR.RER.NAT. GERNHARDT, C., DIPL.-ING., PAT.-ANWAELTE, 8000 MUENCHEN |
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| 8339 | Ceased/non-payment of the annual fee |