GB1283327A - Process for the discontinuous copolymerization of conjugated dienes containing at most five carbon atoms, and vinylaromatic compounds - Google Patents
Process for the discontinuous copolymerization of conjugated dienes containing at most five carbon atoms, and vinylaromatic compoundsInfo
- Publication number
- GB1283327A GB1283327A GB2692071A GB2692071A GB1283327A GB 1283327 A GB1283327 A GB 1283327A GB 2692071 A GB2692071 A GB 2692071A GB 2692071 A GB2692071 A GB 2692071A GB 1283327 A GB1283327 A GB 1283327A
- Authority
- GB
- United Kingdom
- Prior art keywords
- copolymerization
- styrene
- lithium
- initiator
- monomer
- 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
- 238000007334 copolymerization reaction Methods 0.000 title abstract 5
- 150000001993 dienes Chemical class 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 6
- -1 alkenyl aromatic compounds Chemical class 0.000 abstract 5
- 239000000178 monomer Substances 0.000 abstract 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 239000003085 diluting agent Substances 0.000 abstract 3
- 239000003999 initiator Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 2
- 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 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- 239000005049 silicon tetrachloride Substances 0.000 abstract 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 abstract 1
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 abstract 1
- WKNIPOZMZRSXGI-UHFFFAOYSA-N C1=CC=C2C([Li])=CC=CC2=C1[Li] Chemical compound C1=CC=C2C([Li])=CC=CC2=C1[Li] WKNIPOZMZRSXGI-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- PYWOMDDOXZOOJZ-UHFFFAOYSA-N [Li]C1=CC=C([Li])C=C1 Chemical compound [Li]C1=CC=C([Li])C=C1 PYWOMDDOXZOOJZ-UHFFFAOYSA-N 0.000 abstract 1
- VOTZHAZMXFYESM-UHFFFAOYSA-N [Li]C1=CC=CC([Li])=C1 Chemical compound [Li]C1=CC=CC([Li])=C1 VOTZHAZMXFYESM-UHFFFAOYSA-N 0.000 abstract 1
- QQDSVXYDUMVTSQ-UHFFFAOYSA-N [Li]CCCCC[Li] Chemical compound [Li]CCCCC[Li] QQDSVXYDUMVTSQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000007822 coupling agent Substances 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000000977 initiatory effect Effects 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 abstract 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 abstract 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
- 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
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)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
Abstract
1283327 Copolymerizing conjugated dienes and alkenyl aromatic compounds SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 19 April 1971 [16 April 1970] 26920/71 Heading C3P A process for the discontinuous copolymerization of at least one conjugated diene containing at most 5 carbon atoms and at least one alkenyl aromatic compound in a liquid diluent in the presence of an initiator based on lithium comprises (a) preparing a starting mixture of the diluent and a part of the total quantity of each monomer, (b) initiating copolymerization by contacting this mixture with the initiator and (c) keeping the monomer ratio in the reaction mixture constant during the copolymerization by adding the remaining part of each monomer. Specified monomers are butadiene, isoprene and piperylene; and styrene, α-methyl styrene, pmethyl styrene, #-methyl styrene, 1-vinyl naphthalene and 2-vinyl naphthalene. The initiator may be lithium or methyl, isopropyl, butyl, amyl, 2-ethylhexyl or phenyl lithium; ethylene, trimethylene or pentamethylene dilithium; 1,4-dilithiobenzene; 1,5-dilithiobenzene; 1,5-dilithionaphthalene or 1,3,5-trilithium pentane. The diluent may be an aliphatic, cycloaliphatic or aromatic hydrocarbon; and polymerization may be effected in the presence of cross-linking agents, e.g. divinylbenzene, and coupling agents, e.g. silicon tetrachloride, tin tetrachloride, hydrocarbon dihalides, ethyl acetate, ethyl acrylate, phenyl benzoate and diethyl adipate. Examples describe the copolymerization of butadiene and styrene in hexane/ cyclohexane mixtures in the presence of sec. butyl lithium and with the addition of silicon tetrachloride after the monomers.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7005520A NL145567B (en) | 1970-04-16 | 1970-04-16 | PROCEDURE FOR THE NON-CONTINUOUS COPOLYMERIZATION OF CONJUGATED SERVICES WITH UP TO 5 C-ATOMS AND VINYLAROMATIC COMPOUNDS. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1283327A true GB1283327A (en) | 1972-07-26 |
Family
ID=19809870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2692071A Expired GB1283327A (en) | 1970-04-16 | 1971-04-19 | Process for the discontinuous copolymerization of conjugated dienes containing at most five carbon atoms, and vinylaromatic compounds |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4948188B1 (en) |
| BE (1) | BE765465A (en) |
| BR (1) | BR7102205D0 (en) |
| CA (1) | CA981395A (en) |
| DE (1) | DE2117995C2 (en) |
| ES (1) | ES390165A1 (en) |
| FR (1) | FR2089617A1 (en) |
| GB (1) | GB1283327A (en) |
| NL (1) | NL145567B (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4092375A (en) * | 1975-10-03 | 1978-05-30 | Shell Oil Company | Preparation of a non-linear elastomeric copolymer |
| DE2948615A1 (en) * | 1978-12-04 | 1980-06-12 | Asahi Chemical Ind | POLYMER MATERIALS BASED ON AROMATIC ALKENYL RESIN AND THE USE THEREOF FOR THE PRODUCTION OF MOLDED PARTS |
| US4396741A (en) | 1982-03-30 | 1983-08-02 | Shell Oil Company | Photometer-controlled anionic polymerization |
| US5036138A (en) * | 1987-10-19 | 1991-07-30 | Shell Oil Company | Elastomeric compositions, process for the preparation thereof and tires containing them |
| EP0210677B1 (en) * | 1985-07-23 | 1993-09-08 | Shell Internationale Researchmaatschappij B.V. | Process for the anionic polymerization of monomers |
| US5336737A (en) * | 1989-08-16 | 1994-08-09 | Shell Oil Company | Process for the preparation of random copolymers of conjugated dienes and vinyl aromatic compounds |
| US6255421B1 (en) * | 1997-12-10 | 2001-07-03 | Isp Investments Inc. | Non-aqueous, heterogeneous polymerization process and reaction product obtained thereby |
| US6300442B1 (en) * | 1997-12-10 | 2001-10-09 | Isp Investments Inc. | Process for making a cosmetically or pharmaceutically-acceptable emulsion or gel composition |
| USH2030H1 (en) * | 1993-06-29 | 2002-06-04 | Shell Oil Company | Process for the preparation of random copolymers of conjugated dienes and vinyl aromatic compounds |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50156487A (en) * | 1974-06-05 | 1975-12-17 | ||
| JPS5323284U (en) * | 1976-08-05 | 1978-02-27 | ||
| JPS53166493U (en) * | 1978-06-08 | 1978-12-27 | ||
| JPH02109248U (en) * | 1989-02-20 | 1990-08-31 | ||
| DE19801101A1 (en) * | 1998-01-15 | 1999-07-22 | Basf Ag | Production of random and block copolymers suitable for making fibers, films and moldings |
Family Cites Families (2)
| 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 |
| NL136672C (en) * | 1962-07-13 |
-
1970
- 1970-04-16 NL NL7005520A patent/NL145567B/en not_active IP Right Cessation
-
1971
- 1971-04-08 BE BE765465A patent/BE765465A/en not_active IP Right Cessation
- 1971-04-14 JP JP46023185A patent/JPS4948188B1/ja active Pending
- 1971-04-14 BR BR220571A patent/BR7102205D0/en unknown
- 1971-04-14 CA CA110,336A patent/CA981395A/en not_active Expired
- 1971-04-14 ES ES390165A patent/ES390165A1/en not_active Expired
- 1971-04-14 DE DE19712117995 patent/DE2117995C2/en not_active Expired
- 1971-04-14 FR FR7113086A patent/FR2089617A1/fr active Pending
- 1971-04-19 GB GB2692071A patent/GB1283327A/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4092375A (en) * | 1975-10-03 | 1978-05-30 | Shell Oil Company | Preparation of a non-linear elastomeric copolymer |
| DE2948615A1 (en) * | 1978-12-04 | 1980-06-12 | Asahi Chemical Ind | POLYMER MATERIALS BASED ON AROMATIC ALKENYL RESIN AND THE USE THEREOF FOR THE PRODUCTION OF MOLDED PARTS |
| US4396741A (en) | 1982-03-30 | 1983-08-02 | Shell Oil Company | Photometer-controlled anionic polymerization |
| EP0210677B1 (en) * | 1985-07-23 | 1993-09-08 | Shell Internationale Researchmaatschappij B.V. | Process for the anionic polymerization of monomers |
| US5036138A (en) * | 1987-10-19 | 1991-07-30 | Shell Oil Company | Elastomeric compositions, process for the preparation thereof and tires containing them |
| US5064905A (en) * | 1987-10-19 | 1991-11-12 | Shell Oil Company | Elastomeric compositions, process for the preparation thereof and tires containing them |
| US5336737A (en) * | 1989-08-16 | 1994-08-09 | Shell Oil Company | Process for the preparation of random copolymers of conjugated dienes and vinyl aromatic compounds |
| USH2030H1 (en) * | 1993-06-29 | 2002-06-04 | Shell Oil Company | Process for the preparation of random copolymers of conjugated dienes and vinyl aromatic compounds |
| US6255421B1 (en) * | 1997-12-10 | 2001-07-03 | Isp Investments Inc. | Non-aqueous, heterogeneous polymerization process and reaction product obtained thereby |
| US6300442B1 (en) * | 1997-12-10 | 2001-10-09 | Isp Investments Inc. | Process for making a cosmetically or pharmaceutically-acceptable emulsion or gel composition |
Also Published As
| Publication number | Publication date |
|---|---|
| BR7102205D0 (en) | 1973-04-10 |
| JPS4948188B1 (en) | 1974-12-19 |
| DE2117995C2 (en) | 1983-11-03 |
| FR2089617A1 (en) | 1972-01-07 |
| BE765465A (en) | 1971-10-08 |
| NL7005520A (en) | 1971-10-19 |
| NL145567B (en) | 1975-04-15 |
| CA981395A (en) | 1976-01-06 |
| DE2117995A1 (en) | 1971-10-28 |
| ES390165A1 (en) | 1974-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |