CA1077645A - Process for the production of thermoplastically processible rubber - Google Patents
Process for the production of thermoplastically processible rubberInfo
- Publication number
- CA1077645A CA1077645A CA240,986A CA240986A CA1077645A CA 1077645 A CA1077645 A CA 1077645A CA 240986 A CA240986 A CA 240986A CA 1077645 A CA1077645 A CA 1077645A
- Authority
- CA
- Canada
- Prior art keywords
- diblock
- polymers
- styrene
- polymer
- butadiene
- 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
- 229920001971 elastomer Polymers 0.000 title abstract description 16
- 238000000034 method Methods 0.000 title abstract description 15
- 239000005060 rubber Substances 0.000 title abstract description 15
- 230000008569 process Effects 0.000 title abstract description 13
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 150000001993 dienes Chemical class 0.000 claims abstract description 19
- 229920001577 copolymer Polymers 0.000 claims abstract description 11
- -1 sul-phur chlorides Chemical class 0.000 claims abstract description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 32
- 229920000359 diblock copolymer Polymers 0.000 claims description 27
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 12
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 2
- 229920006132 styrene block copolymer Polymers 0.000 claims 4
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 26
- 239000005864 Sulphur Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910001651 emery Inorganic materials 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- SDNVJMZXSOXXQN-UHFFFAOYSA-N 3,4-ditert-butyl-2-methylphenol Chemical compound CC1=C(O)C=CC(C(C)(C)C)=C1C(C)(C)C SDNVJMZXSOXXQN-UHFFFAOYSA-N 0.000 description 1
- 229920004939 Cariflex™ Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229920000428 triblock copolymer 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
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)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2457388A DE2457388C2 (de) | 1974-12-05 | 1974-12-05 | Thermoelastomere Polysegmentcopolymerisate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077645A true CA1077645A (en) | 1980-05-13 |
Family
ID=5932498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA240,986A Expired CA1077645A (en) | 1974-12-05 | 1975-12-03 | Process for the production of thermoplastically processible rubber |
Country Status (10)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6579940B1 (en) * | 1999-10-28 | 2003-06-17 | Edwards Lifesciences Corporation | Thermoplastic elastomeric material as a replacement for natural rubber latex |
| DE10003743A1 (de) | 2000-01-28 | 2001-08-16 | Bayer Ag | Verfahren zur Herstellung eines Copolymerisats auf der Basis von vinylaromatischen Verbindungen und konjugierten Dienen |
| EP2886566B1 (de) * | 2013-12-20 | 2016-09-14 | Continental Reifen Deutschland GmbH | Kautschukmischung und Fahrzeugreifen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3374191A (en) * | 1965-08-05 | 1968-03-19 | Bayer Ag | Process for the production of elastomeric diene polymers with improved properties |
| DE1260794B (de) * | 1963-08-06 | 1968-02-08 | Bayer Ag | Verfahren zur Herstellung kautschukelastischer Dienpolymerer mit verbesserten Eigenschaften |
| DE1570099B2 (de) * | 1965-05-26 | 1976-07-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von oelgestreckten ungesaettigten elastomeren polymerisaten |
| US3607979A (en) * | 1968-10-24 | 1971-09-21 | Shell Oil Co | Hydrophilic chlorosulfonated block copolymers |
| US3694521A (en) * | 1970-07-31 | 1972-09-26 | Shell Oil Co | Chlorosulfonated block copolymers |
| DE2533947A1 (de) * | 1975-07-30 | 1977-02-17 | Hoechst Ag | Metallhaltige disazomethinverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel |
-
1974
- 1974-12-05 DE DE2457388A patent/DE2457388C2/de not_active Expired
-
1975
- 1975-10-29 GB GB44589/75A patent/GB1512557A/en not_active Expired
- 1975-12-02 NL NL7514026A patent/NL7514026A/xx unknown
- 1975-12-03 CA CA240,986A patent/CA1077645A/en not_active Expired
- 1975-12-03 JP JP50143043A patent/JPS5182388A/ja active Pending
- 1975-12-03 IT IT52505/75A patent/IT1052486B/it active
- 1975-12-04 ES ES443195A patent/ES443195A1/es not_active Expired
- 1975-12-04 BR BR7508041*A patent/BR7508041A/pt unknown
- 1975-12-04 BE BE162445A patent/BE836273A/xx not_active IP Right Cessation
- 1975-12-05 FR FR7537334A patent/FR2293447A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL7514026A (nl) | 1976-06-09 |
| BE836273A (fr) | 1976-06-04 |
| DE2457388A1 (de) | 1976-06-10 |
| FR2293447A1 (fr) | 1976-07-02 |
| FR2293447B1 (enrdf_load_stackoverflow) | 1979-07-20 |
| IT1052486B (it) | 1981-06-20 |
| BR7508041A (pt) | 1976-08-24 |
| ES443195A1 (es) | 1977-04-16 |
| DE2457388C2 (de) | 1982-12-02 |
| JPS5182388A (enrdf_load_stackoverflow) | 1976-07-19 |
| GB1512557A (en) | 1978-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |