HRP20190744T1 - Okso-nitrogenirani kompleks kobalta, katalitički sustav koji sadrži navedeni okso-nitrogenirani kompleks i postupak za (ko)polimerizaciju konjugiranih diena - Google Patents
Okso-nitrogenirani kompleks kobalta, katalitički sustav koji sadrži navedeni okso-nitrogenirani kompleks i postupak za (ko)polimerizaciju konjugiranih diena Download PDFInfo
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- HRP20190744T1 HRP20190744T1 HRP20190744TT HRP20190744T HRP20190744T1 HR P20190744 T1 HRP20190744 T1 HR P20190744T1 HR P20190744T T HRP20190744T T HR P20190744TT HR P20190744 T HRP20190744 T HR P20190744T HR P20190744 T1 HRP20190744 T1 HR P20190744T1
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- groups
- polymerization
- group
- conjugated dienes
- catalytic system
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- 238000006116 polymerization reaction Methods 0.000 title claims 12
- 230000003197 catalytic effect Effects 0.000 title claims 11
- 150000001993 dienes Chemical class 0.000 title claims 11
- 238000000034 method Methods 0.000 title claims 4
- 229910017052 cobalt Inorganic materials 0.000 title claims 2
- 239000010941 cobalt Substances 0.000 title claims 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 title claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 229910052782 aluminium Inorganic materials 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 229910052796 boron Inorganic materials 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 150000004700 cobalt complex Chemical class 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims 2
- 229910052733 gallium Inorganic materials 0.000 claims 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 150000002894 organic compounds Chemical class 0.000 claims 2
- 150000002902 organometallic compounds Chemical class 0.000 claims 2
- 230000000737 periodic effect Effects 0.000 claims 2
- 229910052710 silicon Inorganic materials 0.000 claims 2
- 239000010703 silicon Substances 0.000 claims 2
- 229910052718 tin Inorganic materials 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 150000008040 ionic compounds Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
- C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- 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
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers 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
- C08F136/04—Homopolymers 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
- C08F136/06—Butadiene
-
- 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and 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
- C08F36/04—Homopolymers and 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
- C08F36/06—Butadiene
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (13)
1. Okso-nitrogenirani kompleks kobalta koji ima opću formulu (I):
gdje:
- R1 i R2, isti ili različiti, predstavljaju atom vodika, ili su izabrani od linearnih ili granatih C1-C20 alkil grupa koje su izborno halogenirane, cikloalkil grupa koje su izborno supstituirane; aril grupa koje su izborno supstituirane;
- R3 predstavlja atom vodika, ili je izabran od linearnih ili granatih C1-C20 alkil grupa koje su izborno halogenirane, cikloalkil grupa koje su izborno supstituirane; aril grupa koje su izabrane od aromatičnih karbocikličnih grupa izborno supstituiranih s jednom ili više grupa, koje su međusobno iste ili različite, izabrane od: atoma halogena kao što su fluor, klor, brom; hidroksil grupa; C1-C12 alkil grupa; C1-C12 alkoksil grupa, cijano grupa; amino grupa; nitro grupa; ili R3 predstavlja ketoimin grupu koja ima formulu:
gdje R’ i R", isti ili različiti, predstavljaju atom vodika, ili su izabrani od linearnih ili granatih C1-C20 alkil grupa, cikloalkil grupa izborno supstituiranih; aril grupa izborno supstituiranih;
- X1 i X2, isti ili različiti, predstavljaju atom halogena kao što je klor, brom, jod.
2. Okso-nitrogenirani kompleks kobalta koji ima opću formulu (I) prema patentnom zahtjevu 1, gdje:
- R1 i R2, međusobno isti, predstavljaju atom vodika, ili su izabrani od linearnih ili granatih C1-C20 alkil grupa, poželjno su metil grupa;
- R3 je izabran od linearnih ili granatih, C1-C20 alkil grupa, ili fenil grupa izborno supstituiranih s linearnim ili granatim C1-C20 alkil grupama, poželjno supstituiranim s jednom ili više metil, etil, izo-propil grupa; ili
R3 predstavlja ketoimin grupu koja ima formulu:
gdje R’ i R", međusobno isti, predstavljaju atom vodika;
- X1 i X2, međusobno isti, predstavljaju atom halogena kao što su klor, brom, jod, poželjno klor.
3. Katalitički sustav za (ko)polimerizaciju konjugiranih diena koji sadrži:
(a) najmanje jedan okso-nitrogenirani kompleks kobalta koji ima opću formulu (I) prema patentnom zahtjevu 1 ili 2;
(b) najmanje jedan kokatalizator izabran od organskih spojeva elementa M’ različitog od ugljika, pri čemu je navedeni element M’ izabran od elemenata koji pripadaju grupama 2, 12, 13 ili 14, periodnog sustava elemenata, poželjno od: bora, aluminija, cinka, magnezija, galija, kositra, čak poželjnije aluminija, bora.
4. Katalitički sustav za (ko)polimerizaciju konjugiranih diena prema patentnom zahtjevu 3, naznačen time što je navedeni kokatalizator (b) izabran od (b1) aluminijevih alkila koji imaju opću formulu (II):
Al(X’)n(R5)3-n (II)
gdje X’ predstavlja atom halogena kao što su klor, brom, jod, fluor; R5 je izabran od linearnih ili granatih, C1-C20 alkil grupa, cikloalkil grupa, aril grupa, pri čemu su navedene grupe izborno supstituirane s jednim ili više atoma silicija ili germanija; i n je cijeli broj u opsegu od 0 do 2.
5. Katalitički sustav za (ko)polimerizaciju konjugiranih diena prema patentnom zahtjevu 3, naznačen time što je navedeni kokatalizator (b) izabran od (b2) organo-oksigeniranih spojeva elementa M’ koji se razlikuje od ugljika koji pripada grupama 13 ili 14 periodnog sustava elemenata, poželjno spojeva aluminija, galija, kositra.
6. Katalitički sustav za (ko)polimerizaciju konjugiranih diena prema patentnom zahtjevu 3, naznačen time što je navedeni kokatalizator (b) izabran od (b3) organometalnih spojeva ili smjesa organometalnih spojeva elementa M’ različitog od ugljika sposobnog da reagira s okso-nitrogeniranim kompleksom kobalta koji ima opću formulu (I) prema patentnom zahtjevu 1 ili 2, ekstrakcijom iz njega supstituenta X1 ili X2 σ-veze, da bi se formiralo s jedne strane najmanje jedan neutralni spoj, i s druge strane ionski spoj koje se sastoji od kationa koji sadrži metal (Co) koordiniran ligandom, i nekoordinirani anion koji sadrži metal M’, pri čemu je negativni naboj delokaliziran na multicentričnoj strukturi.
7. Katalitički sustav za (ko)polimerizaciju konjugiranih diena prema patentnom zahtjevu 4, naznačen time što navedeni aluminijevi alkili (b1) koji imaju opću formulu (II) su di-etil-aluminijev klorid (DEAC), monoetil-aluminijev diklorid (EADC), etilaluminijevseskviklorid (EASC).
8. Katalitički sustav za (ko)polimerizaciju konjugiranih diena prema patentnom zahtjevu 5, naznačen time što navedeni organo-oksigenirani spojevi (b2) su izabrani od aluminoksana koji imaju opću formulu (III):
(R6)2-Al-O-[-Al(R7)-O-]p-Al-(R8)2 (III)
gdje R6, R7 i R8, isti ili različiti, predstavljaju atom vodika, atom halogena kao što je klor, brom, jod, fluor; ili su izabrani od linearnih ili granatih C1-C20 alkil grupa, cikloalkil grupa, aril grupa, pri čemu su navedene grupe izborno supstituirane s jednim ili više atoma silicija ili germanija; i p je cijeli broj u opsegu od 0 do 1,000.
9. Katalitički sustav za (ko)polimerizaciju konjugiranih diena prema patentnom zahtjevu 8, naznačen time što navedeni organo-oksigenirani spoj (b2) je metilaluminoksan (MAO).
10. Katalitički sustav za (ko)polimerizaciju konjugiranih diena prema patentnom zahtjevu 6, naznačen time što navedeni spojevi ili smjese spojeva (b3) su izabrani od organskih spojeva aluminija i naročito bora, kao što su ona predstavljena sljedećim općim formulama:
[(RC)WH4-W]•[B(RD)4]-; B(RD)3; Al(RD)3; B(RD)3P;
[Ph3C]+•[B(RD)4]-; [(RC)3PH]+•[B(RD)4]-;
[Li]+•[B(RD)4]-; [Li]+•[Al(RD)4]-
gdje w je cijeli broj u opsegu od 0 do 3, svaka grupa RC nezavisno predstavlja alkil grupu ili aril grupu koja ima od 1 do 10 atoma ugljika i svaka grupa RD nezavisno predstavlja aril grupu djelomično ili potpuno, poželjno potpuno, fluoriranu, koja ima od 6 do 20 atoma ugljika, P predstavlja izborno supstituiran pirol radikal.
11. Postupak za (ko)polimerizaciju konjugiranih diena, naznačen time što on koristi katalitički sustav prema bilo kojem od patentnih zahtjeva od 4 do 10.
12. Postupak (ko)polimerizacije prema patentnom zahtjevu 11, naznačen time što navedeni konjugirani dieni su 1,3-butadien, izopren.
13. Postupak polimerizacije 1,3-butadiena ili izoprena, naznačen time što on koristi katalitički sustav prema bilo kojem od patentnih zahtjeva od 4 do 10.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT002201A ITMI20122201A1 (it) | 2012-12-20 | 2012-12-20 | Complesso osso-azotato di cobalto, sistema catalitico comprendente detto complesso osso-azotato e procedimento per la (co)polimerizzazione di dieni coniugati |
| EP13828830.3A EP2935206B1 (en) | 2012-12-20 | 2013-12-18 | Oxo-nitrogenated complex of cobalt, catalytic system comprising said oxo-nitrogenated complex and process for the (co) polymerization of conjugated dienes |
| PCT/IB2013/061078 WO2014097167A1 (en) | 2012-12-20 | 2013-12-18 | Oxo-nitrogenated complex of cobalt, catalytic system comprising said oxo-nitrogenated complex and process for the (co) polymerization of conjugated dienes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20190744T1 true HRP20190744T1 (hr) | 2019-06-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20190744TT HRP20190744T1 (hr) | 2012-12-20 | 2019-04-19 | Okso-nitrogenirani kompleks kobalta, katalitički sustav koji sadrži navedeni okso-nitrogenirani kompleks i postupak za (ko)polimerizaciju konjugiranih diena |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US9493404B2 (hr) |
| EP (1) | EP2935206B1 (hr) |
| JP (1) | JP6407164B2 (hr) |
| KR (1) | KR102078536B1 (hr) |
| CN (1) | CN104854084B (hr) |
| BR (1) | BR112015007737A8 (hr) |
| CA (1) | CA2885275A1 (hr) |
| ES (1) | ES2726817T3 (hr) |
| HR (1) | HRP20190744T1 (hr) |
| HU (1) | HUE044296T2 (hr) |
| IT (1) | ITMI20122201A1 (hr) |
| MY (1) | MY170148A (hr) |
| PL (1) | PL2935206T3 (hr) |
| PT (1) | PT2935206T (hr) |
| RS (1) | RS58667B1 (hr) |
| RU (1) | RU2636153C2 (hr) |
| TR (1) | TR201908485T4 (hr) |
| TW (1) | TWI603974B (hr) |
| WO (1) | WO2014097167A1 (hr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20131830A1 (it) | 2013-11-05 | 2015-05-06 | Versalis Spa | Polibutadieni di-blocco stereoregolari a struttura 1,4-cis/1,2 sindiotattica da polimerizzazione stereospecifica |
| WO2016102639A1 (en) * | 2014-12-23 | 2016-06-30 | Versalis S.P.A. | Oxo-nitrogenated vanadium complex, catalytic system comprising said oxo-nitrogenated vanadium complex and process for (co)polymerising conjugated dienes |
| KR102052439B1 (ko) * | 2016-03-11 | 2019-12-05 | 제이에스알 가부시끼가이샤 | 공중합체의 제조 방법, 중합체 조성물의 제조 방법 및 가교 중합체의 제조 방법 |
| ITUA20163932A1 (it) * | 2016-05-30 | 2017-11-30 | Versalis Spa | Complesso osso-azotato di ferro, sistema catalitico comprendente detto complesso osso-azotato di ferro e procedimento per la (co)polimerizzazione di dieni coniugati |
| IT201700006307A1 (it) * | 2017-01-20 | 2018-07-20 | Versalis Spa | Complesso osso-azotato di ferro, sistema catalitico comprendente detto complesso osso-azotato di ferro e procedimento per la (co)polimerizzazione di dieni coniugati |
| IT201700059763A1 (it) | 2017-05-31 | 2018-12-01 | Versalis Spa | Copolimeri butadiene-isoprene di-blocco e procedimento per la loro preparazione |
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| GB1158296A (en) | 1966-09-26 | 1969-07-16 | Japan Synthetic Rubber Co Ltd | Unsaturated Hydrocarbon Polymers |
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| US3594216A (en) * | 1969-06-19 | 1971-07-20 | Westinghouse Electric Corp | Vapor phase deposition of metal from a metal-organic beta-ketoamine chelate |
| DE2447203C3 (de) | 1974-10-03 | 1982-03-18 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von Polybutadien |
| JPS53143685A (en) | 1977-05-23 | 1978-12-14 | Japan Synthetic Rubber Co Ltd | Preparation of 1,2-polybutadiene |
| DE2911262A1 (de) | 1979-03-22 | 1980-10-02 | Bayer Ag | Katalysator, dessen herstellung und verfahren zur polymerisation von butadien |
| DE3000708A1 (de) | 1980-01-10 | 1981-07-16 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von reaktionsprodukten aus konjugierten diolefinen und aromatischen kohlenwasserstoffen |
| PL276385A1 (en) | 1987-01-30 | 1989-07-24 | Exxon Chemical Patents Inc | Method for polymerization of olefines,diolefins and acetylene unsaturated compounds |
| US4950790A (en) * | 1988-11-14 | 1990-08-21 | Air Products And Chemicals, Inc. | Volatile fluorinated β-ketoimines and associated metal complexes |
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| ITMI20122199A1 (it) | 2012-12-20 | 2014-06-21 | Versalis Spa | Procedimento per la preparazione di (co)polimeri di dieni coniugati in presenza di un sistema catalitico comprendente un complesso bis-imminico di cobalto |
-
2012
- 2012-12-20 IT IT002201A patent/ITMI20122201A1/it unknown
-
2013
- 2013-12-17 TW TW102146496A patent/TWI603974B/zh active
- 2013-12-18 US US14/646,051 patent/US9493404B2/en not_active Expired - Fee Related
- 2013-12-18 PL PL13828830T patent/PL2935206T3/pl unknown
- 2013-12-18 MY MYPI2015000717A patent/MY170148A/en unknown
- 2013-12-18 PT PT13828830T patent/PT2935206T/pt unknown
- 2013-12-18 CN CN201380064085.3A patent/CN104854084B/zh active Active
- 2013-12-18 TR TR2019/08485T patent/TR201908485T4/tr unknown
- 2013-12-18 CA CA2885275A patent/CA2885275A1/en not_active Abandoned
- 2013-12-18 EP EP13828830.3A patent/EP2935206B1/en active Active
- 2013-12-18 HU HUE13828830 patent/HUE044296T2/hu unknown
- 2013-12-18 ES ES13828830T patent/ES2726817T3/es active Active
- 2013-12-18 KR KR1020157010406A patent/KR102078536B1/ko active IP Right Grant
- 2013-12-18 RS RS20190458A patent/RS58667B1/sr unknown
- 2013-12-18 RU RU2015110464A patent/RU2636153C2/ru not_active IP Right Cessation
- 2013-12-18 BR BR112015007737A patent/BR112015007737A8/pt active Search and Examination
- 2013-12-18 WO PCT/IB2013/061078 patent/WO2014097167A1/en active Application Filing
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2935206B1 (en) | 2019-03-06 |
| PT2935206T (pt) | 2019-04-30 |
| RS58667B1 (sr) | 2019-06-28 |
| CA2885275A1 (en) | 2014-06-26 |
| US9493404B2 (en) | 2016-11-15 |
| KR102078536B1 (ko) | 2020-02-19 |
| US20150329577A1 (en) | 2015-11-19 |
| ES2726817T3 (es) | 2019-10-09 |
| ITMI20122201A1 (it) | 2014-06-21 |
| TWI603974B (zh) | 2017-11-01 |
| EP2935206A1 (en) | 2015-10-28 |
| CN104854084B (zh) | 2018-01-02 |
| PL2935206T3 (pl) | 2019-08-30 |
| JP6407164B2 (ja) | 2018-10-17 |
| CN104854084A (zh) | 2015-08-19 |
| HUE044296T2 (hu) | 2019-10-28 |
| RU2636153C2 (ru) | 2017-11-21 |
| BR112015007737A8 (pt) | 2019-07-16 |
| RU2015110464A (ru) | 2017-01-25 |
| BR112015007737A2 (pt) | 2017-07-04 |
| JP2016509580A (ja) | 2016-03-31 |
| MY170148A (en) | 2019-07-09 |
| TR201908485T4 (tr) | 2019-07-22 |
| TW201434846A (zh) | 2014-09-16 |
| WO2014097167A1 (en) | 2014-06-26 |
| KR20150099507A (ko) | 2015-08-31 |
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