CA1087793A - Preparation industrielle de copolymeres sequences, ramifies - Google Patents

Preparation industrielle de copolymeres sequences, ramifies

Info

Publication number: CA1087793A
Authority: CA; Canada
Prior art keywords: monovinyl; weight; branched block; aromatic compound; block copolymers
Prior art date: 1976-03-11
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

Application number

CA272,389A

Other languages

English (en)

Inventor

Gerhard Fahrbach

Karl Gerberding

Erhard Seiler

Dieter Stein

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1976-03-11

Filing date

1977-02-21

Publication date

1980-10-14

1977-02-21 Application filed by BASF SE filed Critical BASF SE

1980-10-14 Application granted granted Critical

1980-10-14 Publication of CA1087793A publication Critical patent/CA1087793A/fr

Status Expired legal-status Critical Current

Links

229920001400 block copolymer Polymers 0.000 title claims abstract description 57
238000004519 manufacturing process Methods 0.000 title claims abstract description 15
229920000642 polymer Polymers 0.000 claims abstract description 52
150000001993 dienes Chemical class 0.000 claims abstract description 29
239000007822 coupling agent Substances 0.000 claims abstract description 17
238000009826 distribution Methods 0.000 claims abstract description 9
230000001747 exhibiting effect Effects 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 32
238000006116 polymerization reaction Methods 0.000 claims description 28
239000003999 initiator Substances 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 22
238000005984 hydrogenation reaction Methods 0.000 claims description 21
239000000178 monomer Substances 0.000 claims description 19
239000004215 Carbon black (E152) Substances 0.000 claims description 9
238000005859 coupling reaction Methods 0.000 claims description 9
230000008878 coupling Effects 0.000 claims description 7
238000010168 coupling process Methods 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
239000005062 Polybutadiene Substances 0.000 claims 1
238000007334 copolymerization reaction Methods 0.000 claims 1
229920002857 polybutadiene Polymers 0.000 claims 1
229920001577 copolymer Polymers 0.000 abstract description 4
239000005022 packaging material Substances 0.000 abstract description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 19
239000000047 product Substances 0.000 description 17
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000007792 addition Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 5
SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
229920001169 thermoplastic Polymers 0.000 description 4
239000004416 thermosoftening plastic Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000004793 Polystyrene Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
-1 cycloaliphatic Chemical group 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
229920002223 polystyrene Polymers 0.000 description 3
238000004448 titration Methods 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
229940116441 divinylbenzene Drugs 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
230000009477 glass transition Effects 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229920003048 styrene butadiene rubber Polymers 0.000 description 2
150000003440 styrenes Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-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
VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
229920002732 Polyanhydride Polymers 0.000 description 1
241000695274 Processa Species 0.000 description 1
229910003910 SiCl4 Inorganic materials 0.000 description 1
239000002174 Styrene-butadiene Substances 0.000 description 1
FYOQEFGAZKEPGG-UHFFFAOYSA-N [Li]C1=CC=C(C)C=C1 Chemical compound [Li]C1=CC=C(C)C=C1 FYOQEFGAZKEPGG-UHFFFAOYSA-N 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000010539 anionic addition polymerization reaction Methods 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000002902 bimodal effect Effects 0.000 description 1
MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 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
238000007707 calorimetry Methods 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
LEKSIJZGSFETSJ-UHFFFAOYSA-N cyclohexane;lithium Chemical compound [Li]C1CCCCC1 LEKSIJZGSFETSJ-UHFFFAOYSA-N 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
VFURVLVRHAMJKG-UHFFFAOYSA-N dichloro-[2-[dichloro(methyl)silyl]ethyl]-methylsilane Chemical compound C[Si](Cl)(Cl)CC[Si](C)(Cl)Cl VFURVLVRHAMJKG-UHFFFAOYSA-N 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
229920005684 linear copolymer Polymers 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920001470 polyketone Polymers 0.000 description 1
229920006216 polyvinyl aromatic Polymers 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
239000005049 silicon tetrachloride Substances 0.000 description 1
239000011115 styrene butadiene Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 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

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)

CA272,389A 1976-03-11 1977-02-21 Preparation industrielle de copolymeres sequences, ramifies Expired CA1087793A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19762610069 DE2610069A1 (de)	1976-03-11	1976-03-11	Verzweigte blockcopolymerisate und verfahren zu ihrer herstellung
DEP2610069.6		1976-03-11

Publications (1)

Publication Number	Publication Date
CA1087793A true CA1087793A (fr)	1980-10-14

Family

ID=5972080

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA272,389A Expired CA1087793A (fr)	1976-03-11	1977-02-21	Preparation industrielle de copolymeres sequences, ramifies

Country Status (11)

Country	Link
BE (1)	BE852322A (fr)
CA (1)	CA1087793A (fr)
DE (1)	DE2610069A1 (fr)
DK (1)	DK105077A (fr)
ES (1)	ES456696A1 (fr)
FR (1)	FR2343762A1 (fr)
GB (1)	GB1571669A (fr)
IT (1)	IT1075110B (fr)
NL (1)	NL7702384A (fr)
NO (1)	NO770851L (fr)
SE (1)	SE7702729L (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3032832A1 (de) *	1980-08-30	1982-04-22	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von verzweigten blockcopolymerisaten, verwendung derselben und formteile aus diesen
JPS61190514A (ja) *	1985-02-18	1986-08-25	Sumitomo Chem Co Ltd	熱可塑性弾性体の製造方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3595942A (en) *	1968-12-24	1971-07-27	Shell Oil Co	Partially hydrogenated block copolymers
US3639517A (en) *	1969-09-22	1972-02-01	Phillips Petroleum Co	Resinous branched block copolymers

1976
- 1976-03-11 DE DE19762610069 patent/DE2610069A1/de not_active Withdrawn
1977
- 1977-02-09 IT IT20121/77A patent/IT1075110B/it active
- 1977-02-21 CA CA272,389A patent/CA1087793A/fr not_active Expired
- 1977-03-04 NL NL7702384A patent/NL7702384A/xx not_active Application Discontinuation
- 1977-03-07 FR FR7706606A patent/FR2343762A1/fr active Granted
- 1977-03-10 DK DK105077A patent/DK105077A/da unknown
- 1977-03-10 GB GB10100/77A patent/GB1571669A/en not_active Expired
- 1977-03-10 ES ES456696A patent/ES456696A1/es not_active Expired
- 1977-03-10 NO NO770851A patent/NO770851L/no unknown
- 1977-03-10 BE BE175674A patent/BE852322A/fr unknown
- 1977-03-10 SE SE7702729A patent/SE7702729L/xx unknown

Also Published As

Publication number	Publication date
NO770851L (no)	1977-09-13
NL7702384A (nl)	1977-09-13
ES456696A1 (es)	1978-01-16
DK105077A (da)	1977-09-12
FR2343762A1 (fr)	1977-10-07
DE2610069A1 (de)	1977-09-22
GB1571669A (en)	1980-07-16
SE7702729L (sv)	1977-09-12
IT1075110B (it)	1985-04-22
FR2343762B1 (fr)	1982-08-13
BE852322A (fr)	1977-09-12

Legal Events

Date	Code	Title	Description
1997-10-14	MKEX	Expiry

Publication	Publication Date	Title
US4167545A (en)	1979-09-11	Branched block copolymers and their manufacture
US4086298A (en)	1978-04-25	Branched block copolymers and their manufacture
CA1120636A (fr)	1982-03-23	Copolymeres greffes, couples a adhesivite accrue pour produits adhesifs
CA1180840A (fr)	1985-01-08	Preparation de copolymeres sequences ramifies
US4107236A (en)	1978-08-15	Hydrogenated block copolymers containing a block derived from low vinyl polybutadiene and a block derived from medium vinyl polybutadiene
JP2718593B2 (ja)	1998-02-25	多様式ポリマーの製造方法
US4925899A (en)	1990-05-15	Bimodal star-block copolymers, showing excellent optical properties and resilience, and process for their manufacture
US3468972A (en)	1969-09-23	Control of branching and coupling in lithium-terminated polymers
EP0153727B1 (fr)	1993-05-05	Polymère resineux transparent resistant au fissurage
US3281383A (en)	1966-10-25	Branched polymers prepared from monolithium-terminated polymers and compounds having at least three reactive sites
JP4599495B2 (ja)	2010-12-15	線状ブロック共重合体、及びそれを含む樹脂組成物
US4152370A (en)	1979-05-01	Preparation, composition, and use of block polymers
US3949020A (en)	1976-04-06	Thermoplastic block polymers
US4221884A (en)	1980-09-09	Clear impact resistant thermoplastic star-block copolymers
US4874821A (en)	1989-10-17	Block copolymer and process for preparing it
US3992483A (en)	1976-11-16	Promoters in the polymerization of monovinyl-aromatic compounds with primary lithium initiators
CA1087339A (fr)	1980-10-07	Copolymeres sequences, ramifies d'un produit aromatique monovinylique et d'un diene conjugue
US3959412A (en)	1976-05-25	Block polymer preparation
JP3607738B2 (ja)	2005-01-05	芳香族ビニルモノマーと共役ジエンとの星型ブロックコポリマーと、その製造方法と、この星型ブロックコポリマーと結晶性ポリスチレンとを含む組成物
US4346198A (en)	1982-08-24	Clear impact resistant thermoplastic star-block copolymers
GB2225330A (en)	1990-05-30	Linear alternating-block copolymers
US4891410A (en)	1990-01-02	Butadiene/sytrene block copolymers having an asymmetric structure, their preparation and their use as molding materials
CA1087793A (fr)	1980-10-14	Preparation industrielle de copolymeres sequences, ramifies
US3957913A (en)	1976-05-18	Process for the preparation of thermoplastic elastomeric block copolymers
CA1087340A (fr)	1980-10-07	Melanges de polymeres transparents, offrant une grande resistance aux chocs