CS252402B1 - Method of butadiene-1,3 selective polymerization from c4-fractions - Google Patents

Method of butadiene-1,3 selective polymerization from c4-fractions Download PDF

Info

Publication number: CS252402B1
Authority: CS; Czechoslovakia
Prior art keywords: polymerization; initiators; butadiene; polymers; fractions
Prior art date: 1982-11-29

Application number

CS827983A

Other languages

Czech (cs)

English (en)

Inventor

Volker Griehl

Elisabeth Antonova

Original Assignee

Volker Griehl

Elisabeth Antonova

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.)

1982-11-29

Filing date

1983-11-10

Publication date

1987-09-17

1983-11-10 Application filed by Volker Griehl, Elisabeth Antonova filed Critical Volker Griehl

1987-09-17 Publication of CS252402B1 publication Critical patent/CS252402B1/cs

Links

238000006116 polymerization reaction Methods 0.000 title claims description 16
238000000034 method Methods 0.000 title claims description 14
239000003999 initiator Substances 0.000 claims description 26
229920000642 polymer Polymers 0.000 claims description 26
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
238000007306 functionalization reaction Methods 0.000 claims description 5
229930195733 hydrocarbon Natural products 0.000 claims description 5
150000002430 hydrocarbons Chemical class 0.000 claims description 5
229910052744 lithium Inorganic materials 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
239000001569 carbon dioxide Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
-1 alkyl lithium compound Chemical class 0.000 claims description 3
CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 claims description 2
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 2
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 2
229920002857 polybutadiene Polymers 0.000 description 10
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 9
239000005062 Polybutadiene Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
230000001588 bifunctional effect Effects 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000003505 polymerization initiator Substances 0.000 description 3
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
238000009826 distribution Methods 0.000 description 2
238000010528 free radical solution polymerization reaction Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000000178 monomer Substances 0.000 description 2
239000012454 non-polar solvent Substances 0.000 description 2
150000002900 organolithium compounds Chemical class 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
229920006250 telechelic polymer Polymers 0.000 description 2
238000004448 titration Methods 0.000 description 2
HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
241001611408 Nebo Species 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000001273 butane Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000005336 cracking Methods 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000012039 electrophile Substances 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000004005 microsphere Substances 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
QSGNIZYSOOADSE-UHFFFAOYSA-N penta-1,4-dienylbenzene Chemical compound C=CCC=CC1=CC=CC=C1 QSGNIZYSOOADSE-UHFFFAOYSA-N 0.000 description 1
229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920013730 reactive polymer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton

Landscapes

Chemical & Material Sciences (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polymerization Catalysts (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CS827983A 1982-11-29 1983-11-10 Method of butadiene-1,3 selective polymerization from c4-fractions CS252402B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD24528482A DD237670A1 (de)	1982-11-29	1982-11-29	Verfahren zur selektivpolymerisation von butadien aus c tief 4-fraktionen

Publications (1)

Publication Number	Publication Date
CS252402B1 true CS252402B1 (en)	1987-09-17

Family

ID=5542767

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS827983A CS252402B1 (en)	1982-11-29	1983-11-10	Method of butadiene-1,3 selective polymerization from c4-fractions

Country Status (2)

Country	Link
CS (1)	CS252402B1 (de)
DD (1)	DD237670A1 (de)

1982
- 1982-11-29 DD DD24528482A patent/DD237670A1/de not_active IP Right Cessation
1983
- 1983-11-10 CS CS827983A patent/CS252402B1/cs unknown

Also Published As

Publication number	Publication date
DD237670A1 (de)	1986-07-23

Publication	Publication Date	Title
JP2707086B2 (ja)	1998-01-28	リビング重合体錯体の製法
US3644322A (en)	1972-02-22	Polymerization of conjugated dienes and monovinyl aromatic compounds with multifunctional polymerization initiators
EP0002864A1 (de)	1979-07-11	Verfahren zur Herstellung von linearen und/oder radialen Polymerisaten
Foss et al.	1977	A new difunctional anionic initiator
KR20170008797A (ko)	2017-01-24	폴리알케닐 커플링제 및 이것으로 제조된 공액 디엔 중합체
US4960842A (en)	1990-10-02	Amine containing initiator system for anionic polymerization
EP0501957B1 (de)	1996-07-17	Elastomere pfropfcopolymere und ihre verwendung als kompatibilisierungsmittel
US3959412A (en)	1976-05-25	Block polymer preparation
EP0459588B1 (de)	1995-08-02	Funktionalisierte sternförmige Polymere
KR100401300B1 (ko)	2003-12-18	코어관능화된성상블록공중합체
US5290872A (en)	1994-03-01	Branched and hydrogenated block copolymer, procedures for its preparation and use
US20050107541A1 (en)	2005-05-19	Coupled radial anionic polymers
CS252402B1 (en)	1987-09-17	Method of butadiene-1,3 selective polymerization from c4-fractions
JP2012500310A5 (de)	2014-05-29
US4254238A (en)	1981-03-03	Hydrocarbon/ethylene oxide random graft copolymers
GB2118952A (en)	1983-11-09	Anionic polymerisation of unsaturated monomers
FR2530642A1 (fr)	1984-01-27	Procede pour la preparation d'initiateurs de polymerisation multifonctionnels
GB2138005A (en)	1984-10-17	Functionally-Terminated Polymers
GB2048899A (en)	1980-12-17	Lactone graft polymers
US5266647A (en)	1993-11-30	Branched copolymers
JPH07149822A (ja)	1995-06-13	テレキーレの製造方法
Lindsell et al.	1990	The preparation and characterization of phosphorus-terminated poly-1, 3-butadiene: new telechelic ionomers
CS237591B1 (en)	1985-09-17	Method of butadiene selective polymerization from c4 fractions into star homopolymers and copolymers
CN107337772B (zh)	2020-03-27	一种带羟基的苯乙烯类共聚物的制备方法
CS232313B1 (en)	1985-01-16	Method of selective polymerization of butadiene feom c4 fraction