Skip to main content
Erschienen in: Polymer Bulletin 11/2020

13.12.2019 | Review Paper

Ni/Pd-catalyzed coordination-insertion copolymerization of ethylene with alkyl acrylate

verfasst von: Urmilla Baruah, Prakash J. Saikia, Shashi D. Baruah

Erschienen in: Polymer Bulletin | Ausgabe 11/2020

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Commercially, polyethylene is a highly produced commodity polymer. But due to its hydrophobic nature, it limits its applications, where utility is based on surface properties, such as adhesion, printability, wettability, and miscibility with other polar polymers. Therefore, the presence of a hydrophilic polar functionality is desired to overcome such difficulties. With its high exigency, synthesis of functionalized polyethylene with unique surface properties is now a very challenging task to be accomplished. In this perspective, developments on palladium and nickel (mainly based on ligands containing neutral α-diimine and anionic phosphine–sulfonate derivative)-mediated coordination/insertion copolymerization of ethylene with polar functionalized co-monomers are discussed herein.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
1.
Zurück zum Zitat Gaikwad SR, Deshmukh SS, Gonnade RG, Rajamohanan PR, Chikkali SH (2015) Insertion copolymerization of difunctional polar vinyl monomers with ethylene. ACS Macro Lett 4:933–937 Gaikwad SR, Deshmukh SS, Gonnade RG, Rajamohanan PR, Chikkali SH (2015) Insertion copolymerization of difunctional polar vinyl monomers with ethylene. ACS Macro Lett 4:933–937
2.
Zurück zum Zitat Hutley TJ, Ouederni M (2016) Polyolefins: the history and economic impact. In: AlMa’adeed MA-A, Krupa I (eds) Polyolefin compounds and materials: fundamentals and industrial applications. Springer series on polymer and composite materials. Springer, Berlin Hutley TJ, Ouederni M (2016) Polyolefins: the history and economic impact. In: AlMa’adeed MA-A, Krupa I (eds) Polyolefin compounds and materials: fundamentals and industrial applications. Springer series on polymer and composite materials. Springer, Berlin
3.
Zurück zum Zitat Boffa LS, Novak BM (2000) Copolymerization of Polar Monomers with Olefins Using Transition-Metal Complexes. Chem Rev 100:1479–1493PubMed Boffa LS, Novak BM (2000) Copolymerization of Polar Monomers with Olefins Using Transition-Metal Complexes. Chem Rev 100:1479–1493PubMed
4.
Zurück zum Zitat Britovsek GJP, Gibson VC, Wass DF (1999) The search for new-generation olefin polymerization catalysts: life beyond metallocenes. Angew Chem Int Ed 38:428–447 Britovsek GJP, Gibson VC, Wass DF (1999) The search for new-generation olefin polymerization catalysts: life beyond metallocenes. Angew Chem Int Ed 38:428–447
5.
Zurück zum Zitat Baruah U, Gautam A, Saikia M, Borphukan S, Saikia PJ, Baruah SD (2017) Monodisperse copolymer nanosphere assembly by miniemulsion polymerization. Eur Polym J 96:111–118 Baruah U, Gautam A, Saikia M, Borphukan S, Saikia PJ, Baruah SD (2017) Monodisperse copolymer nanosphere assembly by miniemulsion polymerization. Eur Polym J 96:111–118
6.
Zurück zum Zitat Baruah U, Saikia M, Assanvo EF, Borphukan S, Phukan L, Gautam A, Baruah SD (2016) Synthesis and thermal analysis of poly(methyl methacrylate) oligomer functionalized polyethylene block copolymer. Polym Bull 74:2137–2158 Baruah U, Saikia M, Assanvo EF, Borphukan S, Phukan L, Gautam A, Baruah SD (2016) Synthesis and thermal analysis of poly(methyl methacrylate) oligomer functionalized polyethylene block copolymer. Polym Bull 74:2137–2158
7.
Zurück zum Zitat Saikia M, Borphukan S, Baruah U, Gautam A, Saikia PJ, Baruah SD (2017) Poly(ethylene-co-BMA) via dual concurrent ATRP–RAFT and its thermokinetic study. J Therm Anal Calorim 131:1517–1526 Saikia M, Borphukan S, Baruah U, Gautam A, Saikia PJ, Baruah SD (2017) Poly(ethylene-co-BMA) via dual concurrent ATRP–RAFT and its thermokinetic study. J Therm Anal Calorim 131:1517–1526
8.
Zurück zum Zitat Boaen NK, Hillmyer MA (2005) Post-polymerization functionalization of polyolefins. Chem Soc Rev 34:267–275PubMed Boaen NK, Hillmyer MA (2005) Post-polymerization functionalization of polyolefins. Chem Soc Rev 34:267–275PubMed
9.
Zurück zum Zitat Rojas G, Berda EB, Wagener KB (2008) Precision polyolefin structure: modeling polyethylene containing alkyl branches. Polymer 49:2985–2995 Rojas G, Berda EB, Wagener KB (2008) Precision polyolefin structure: modeling polyethylene containing alkyl branches. Polymer 49:2985–2995
10.
Zurück zum Zitat Camm KD, Castro NM, Liu Y, Czechura P, Snelgrove JL, Fogg DE (2007) Tandem ROMP–hydrogenation with a third-generation grubbs catalyst. J Am Chem Soc 129:4168–4169PubMed Camm KD, Castro NM, Liu Y, Czechura P, Snelgrove JL, Fogg DE (2007) Tandem ROMP–hydrogenation with a third-generation grubbs catalyst. J Am Chem Soc 129:4168–4169PubMed
11.
Zurück zum Zitat Leblanc A, Grau E, Broyer JP, Boisson C, Spitz R, Monteil V (2011) Homo- and copolymerizations of (meth)acrylates with olefins (styrene, ethylene) using neutral nickel complexes: a dual radical/catalytic pathway. Macromolecules 44:3293–3301 Leblanc A, Grau E, Broyer JP, Boisson C, Spitz R, Monteil V (2011) Homo- and copolymerizations of (meth)acrylates with olefins (styrene, ethylene) using neutral nickel complexes: a dual radical/catalytic pathway. Macromolecules 44:3293–3301
12.
Zurück zum Zitat Daigle JC, Piche L, Claverie JP (2011) Preparation of functional polyethylenes by catalytic copolymerization. Macromolecules 44:1760–1762 Daigle JC, Piche L, Claverie JP (2011) Preparation of functional polyethylenes by catalytic copolymerization. Macromolecules 44:1760–1762
13.
Zurück zum Zitat Carrow BP, Nozaki K (2012) Synthesis of functional polyolefins using cationic bisphosphine monoxide–palladium complexes. J Am Chem Soc 134:8802–8805PubMed Carrow BP, Nozaki K (2012) Synthesis of functional polyolefins using cationic bisphosphine monoxide–palladium complexes. J Am Chem Soc 134:8802–8805PubMed
14.
Zurück zum Zitat Meduri A, Montini T, Ragaini F, Fornasiero P, Zangrando E, Milani B (2013) Palladium-catalyzed ethylene/methyl acrylate cooligomerization: effect of a new nonsymmetric α-diimine. ChemCatChem 5:1170–1183 Meduri A, Montini T, Ragaini F, Fornasiero P, Zangrando E, Milani B (2013) Palladium-catalyzed ethylene/methyl acrylate cooligomerization: effect of a new nonsymmetric α-diimine. ChemCatChem 5:1170–1183
15.
Zurück zum Zitat Contrella ND, Sampson JR, Jordan RF (2014) Copolymerization of ethylene and methyl acrylate by cationic palladium catalysts that contain phosphine-diethyl phosphonate ancillary ligands. Organometallics 33:3546–3555 Contrella ND, Sampson JR, Jordan RF (2014) Copolymerization of ethylene and methyl acrylate by cationic palladium catalysts that contain phosphine-diethyl phosphonate ancillary ligands. Organometallics 33:3546–3555
16.
Zurück zum Zitat Takano S, Takeuchi D, Osakada K, Akamatsu N, Shishido A (2014) Dipalladium catalyst for olefin polymerization: Introduction of acrylate units into the main chain of branched polyethylene. Angew Chemie Int Ed 53:9246–9250 Takano S, Takeuchi D, Osakada K, Akamatsu N, Shishido A (2014) Dipalladium catalyst for olefin polymerization: Introduction of acrylate units into the main chain of branched polyethylene. Angew Chemie Int Ed 53:9246–9250
17.
Zurück zum Zitat Allen KE, Campos J, Daugulis O, Brookhart M (2015) Living polymerization of ethylene and copolymerization of ethylene/methyl acrylate using “sandwich” diimine palladium catalysts. ACS Catal 5:456–464 Allen KE, Campos J, Daugulis O, Brookhart M (2015) Living polymerization of ethylene and copolymerization of ethylene/methyl acrylate using “sandwich” diimine palladium catalysts. ACS Catal 5:456–464
18.
Zurück zum Zitat Nuzzo RG, Smolinsky G (1984) Preparation and characterization of functionalized polyethylene surfaces. Macromolecules 17:1013–1019 Nuzzo RG, Smolinsky G (1984) Preparation and characterization of functionalized polyethylene surfaces. Macromolecules 17:1013–1019
19.
Zurück zum Zitat Johnson LK, Mecking S, Brookhart M (1996) Copolymerization of ethylene and propylene with functionalized vinyl monomers by palladium(II) catalysts. J Am Chem Soc 118:267–268 Johnson LK, Mecking S, Brookhart M (1996) Copolymerization of ethylene and propylene with functionalized vinyl monomers by palladium(II) catalysts. J Am Chem Soc 118:267–268
20.
Zurück zum Zitat Johnson LK, Killian CM, Brookhart M (1995) New Pd(II)-and Ni(II)-based catalysts for polymerization of ethylene and. alpha.-olefins. J Am Chem Soc 117:6414–6415 Johnson LK, Killian CM, Brookhart M (1995) New Pd(II)-and Ni(II)-based catalysts for polymerization of ethylene and. alpha.-olefins. J Am Chem Soc 117:6414–6415
21.
Zurück zum Zitat Rhinehart JL, Brown LA, Long BK (2013) A robust Ni(II) α-diimine catalyst for high temperature ethylene polymerization. J Am Chem Soc 135:16316–16319PubMed Rhinehart JL, Brown LA, Long BK (2013) A robust Ni(II) α-diimine catalyst for high temperature ethylene polymerization. J Am Chem Soc 135:16316–16319PubMed
22.
Zurück zum Zitat Meinhard D, Wegner M, Kipiani G, Hearley A, Reuter P, Fischer S, Marti O, Rieger B (2007) New nickel(II) diimine complexes and the control of polyethylene microstructure by catalyst design. J Am Chem Soc 129:9182–9191PubMed Meinhard D, Wegner M, Kipiani G, Hearley A, Reuter P, Fischer S, Marti O, Rieger B (2007) New nickel(II) diimine complexes and the control of polyethylene microstructure by catalyst design. J Am Chem Soc 129:9182–9191PubMed
23.
Zurück zum Zitat Ionkin AS, Marshall WJ (2004) Ortho-5-methylfuran- and benzofuran-substituted η3-allyl(α-diimine)nickel(II) complexes: syntheses, structural characterization, and the first polymerization results. Organometallics 23:3276–3283 Ionkin AS, Marshall WJ (2004) Ortho-5-methylfuran- and benzofuran-substituted η3-allyl(α-diimine)nickel(II) complexes: syntheses, structural characterization, and the first polymerization results. Organometallics 23:3276–3283
24.
Zurück zum Zitat Schmid M, Eberhardt R, Klinga M, Leskela M, Rieger B (2001) New C2v- and chiral C2-symmetric olefin polymerization catalysts based on nickel(II) and palladium(II) diimine complexes bearing 2,6-diphenyl aniline moieties: synthesis, structural characterization, and first insight into polymerization properties. Organometallics 20:2321–2330 Schmid M, Eberhardt R, Klinga M, Leskela M, Rieger B (2001) New C2v- and chiral C2-symmetric olefin polymerization catalysts based on nickel(II) and palladium(II) diimine complexes bearing 2,6-diphenyl aniline moieties: synthesis, structural characterization, and first insight into polymerization properties. Organometallics 20:2321–2330
25.
Zurück zum Zitat Camacho DH, Guan Z (2005) Living polymerization of α-olefins at elevated temperatures catalyzed by a highly active and robust cyclophane-based nickel catalyst. Macromolecules 38:2544–2546 Camacho DH, Guan Z (2005) Living polymerization of α-olefins at elevated temperatures catalyzed by a highly active and robust cyclophane-based nickel catalyst. Macromolecules 38:2544–2546
26.
Zurück zum Zitat Zanchin G, Bertini F, Vendier L, Ricci G, Lorber C, Leone G (2019) Copolymerization of ethylene with propylene and higher α-olefins catalyzed by (imido)vanadium(iv) dichloride complexes. Polym Chem 10:6200–6216 Zanchin G, Bertini F, Vendier L, Ricci G, Lorber C, Leone G (2019) Copolymerization of ethylene with propylene and higher α-olefins catalyzed by (imido)vanadium(iv) dichloride complexes. Polym Chem 10:6200–6216
27.
Zurück zum Zitat Nakano R, Chung LW, Watanabe Y, Okuno Y, Okumura Y, Ito S, Morokuma K, Nozaki K (2016) Elucidating the key role of phosphine–sulfonate ligands in palladium-catalyzed ethylene polymerization: effect of ligand structure on the molecular weight and linearity of polyethylene. Catalysis 6:6101–6113 Nakano R, Chung LW, Watanabe Y, Okuno Y, Okumura Y, Ito S, Morokuma K, Nozaki K (2016) Elucidating the key role of phosphine–sulfonate ligands in palladium-catalyzed ethylene polymerization: effect of ligand structure on the molecular weight and linearity of polyethylene. Catalysis 6:6101–6113
28.
Zurück zum Zitat Noda S, Nakamura A, Kochi T, Lung WC, Morokuma K, Nozaki K (2009) Mechanistic studies on the formation of linear polyethylene chain catalyzed by palladium phosphine–sulfonate complexes: experiment and theoretical studies. J Am Chem Soc 131:14088–14100PubMed Noda S, Nakamura A, Kochi T, Lung WC, Morokuma K, Nozaki K (2009) Mechanistic studies on the formation of linear polyethylene chain catalyzed by palladium phosphine–sulfonate complexes: experiment and theoretical studies. J Am Chem Soc 131:14088–14100PubMed
29.
Zurück zum Zitat Haras A, Anderson GDW, Michalak A, Rieger B, Ziegler T (2006) Computational insight into catalytic control of poly(ethylene–methyl acrylate) topology. Organometallics 25:4491–4497 Haras A, Anderson GDW, Michalak A, Rieger B, Ziegler T (2006) Computational insight into catalytic control of poly(ethylene–methyl acrylate) topology. Organometallics 25:4491–4497
30.
Zurück zum Zitat Guironnet D, Caporaso L, Neuwald B, Go I, Cavallo L, Mecking S (2010) Mechanistic insights on acrylate insertion polymerization. J Am Chem Soc 132:4418–4426PubMed Guironnet D, Caporaso L, Neuwald B, Go I, Cavallo L, Mecking S (2010) Mechanistic insights on acrylate insertion polymerization. J Am Chem Soc 132:4418–4426PubMed
31.
Zurück zum Zitat Nozaki K, Kusumoto S, Noda S, Kochi T, Chung LW, Morokuma K (2010) Why did incorporation of acrylonitrile to a linear polyethylene become possible? Comparison of phosphine–sulfonate ligand with diphosphine and imine–phenolate ligands in the Pd-catalyzed ethylene/acrylonitrile copolymerization. J Am Chem Soc 132:16030–16042PubMed Nozaki K, Kusumoto S, Noda S, Kochi T, Chung LW, Morokuma K (2010) Why did incorporation of acrylonitrile to a linear polyethylene become possible? Comparison of phosphine–sulfonate ligand with diphosphine and imine–phenolate ligands in the Pd-catalyzed ethylene/acrylonitrile copolymerization. J Am Chem Soc 132:16030–16042PubMed
32.
Zurück zum Zitat Kim Y, Jordan RF (2011) Synthesis, structures, and ethylene dimerization reactivity of palladium alkyl complexes that contain a chelating phosphine–trifluoroborate ligand. Organometallics 30:4250–4256 Kim Y, Jordan RF (2011) Synthesis, structures, and ethylene dimerization reactivity of palladium alkyl complexes that contain a chelating phosphine–trifluoroborate ligand. Organometallics 30:4250–4256
33.
Zurück zum Zitat Gott AL, Piers WE, Dutton JL, Mcdonald R, Parvez M (2011) Dimerization of ethylene by palladium complexes containing bidentate trifluoroborate-functionalized phosphine ligands. Organometallics 30:4236–4249 Gott AL, Piers WE, Dutton JL, Mcdonald R, Parvez M (2011) Dimerization of ethylene by palladium complexes containing bidentate trifluoroborate-functionalized phosphine ligands. Organometallics 30:4236–4249
34.
Zurück zum Zitat Liu W, Malinoski JM, Brookhart M, Hill C, Carolina N (2002) Ethylene polymerization and ethylene/methyl 10-undecenoate copolymerization using nickel(II) and palladium(II) complexes derived from a bulky P, O chelating ligand. Organometallics 21:2836–2838 Liu W, Malinoski JM, Brookhart M, Hill C, Carolina N (2002) Ethylene polymerization and ethylene/methyl 10-undecenoate copolymerization using nickel(II) and palladium(II) complexes derived from a bulky P, O chelating ligand. Organometallics 21:2836–2838
35.
Zurück zum Zitat Malinoski JM, Brookhart M, Hill C, Carolina N (2003) Polymerization and oligomerization of ethylene by cationic nickel(II) and palladium(II) complexes containing bidentate phenacyldiarylphosphine ligands. Organometallic 22:5324–5335 Malinoski JM, Brookhart M, Hill C, Carolina N (2003) Polymerization and oligomerization of ethylene by cationic nickel(II) and palladium(II) complexes containing bidentate phenacyldiarylphosphine ligands. Organometallic 22:5324–5335
36.
Zurück zum Zitat Britovsek GJP, Keim W, Mecking S, Sainz D, Wagner T (1993) Hemilabile P, O-ligands in palladium catalysed C-C linkages: codimerization of ethylene and styrene and cooligomerization of ethylene and carbon monoxide. J Chem Soc Chem Commun 1993:1632–1634 Britovsek GJP, Keim W, Mecking S, Sainz D, Wagner T (1993) Hemilabile P, O-ligands in palladium catalysed C-C linkages: codimerization of ethylene and styrene and cooligomerization of ethylene and carbon monoxide. J Chem Soc Chem Commun 1993:1632–1634
37.
Zurück zum Zitat Mecking S, Keim W (1996) Cationic palladium η3-allyl complexes with hemilabile p, o-ligands: Synthesis and reactivity, insertion of ethylene into the pd–allyl function. Organometallics 15:2650–2656 Mecking S, Keim W (1996) Cationic palladium η3-allyl complexes with hemilabile p, o-ligands: Synthesis and reactivity, insertion of ethylene into the pd–allyl function. Organometallics 15:2650–2656
38.
Zurück zum Zitat Reisinger CM, Nowack J, Volkmer D, Rieger B (2007) Novel palladium complexes employing mixed phosphine phosphonates and phosphine phosphinates as anionic chelating [P, O] ligands. Dalton Trans 2:272–278 Reisinger CM, Nowack J, Volkmer D, Rieger B (2007) Novel palladium complexes employing mixed phosphine phosphonates and phosphine phosphinates as anionic chelating [P, O] ligands. Dalton Trans 2:272–278
39.
Zurück zum Zitat Carrow BP, Nozaki K (2014) Transition-metal-catalyzed functional polyolefin synthesis: effecting control through chelating ancillary ligand design and mechanistic insights. Macromolecules 47:2541–2555 Carrow BP, Nozaki K (2014) Transition-metal-catalyzed functional polyolefin synthesis: effecting control through chelating ancillary ligand design and mechanistic insights. Macromolecules 47:2541–2555
40.
Zurück zum Zitat Brassat I, Keim W, Killat S, Mothrath M, Francesco C, Paolo G (2000) Synthesis and catalytic activity of allyl, methallyl and methyl complexes of nickel(II) and palladium(II) with biphosphine monoxide ligands: oligomerization of ethylene and copolymerization of ethylene and carbon monoxide. J Mol Catal A Chem 157:41–58 Brassat I, Keim W, Killat S, Mothrath M, Francesco C, Paolo G (2000) Synthesis and catalytic activity of allyl, methallyl and methyl complexes of nickel(II) and palladium(II) with biphosphine monoxide ligands: oligomerization of ethylene and copolymerization of ethylene and carbon monoxide. J Mol Catal A Chem 157:41–58
41.
Zurück zum Zitat Mitsushige Y, Carrow BP, Ito S, Nozaki K (2016) Ligand-controlled insertion regioselectivity accelerates copolymerisation of ethylene with methyl acrylate by cationic bisphosphine monoxide–palladium catalysts. Chem Sci 7:737–744PubMed Mitsushige Y, Carrow BP, Ito S, Nozaki K (2016) Ligand-controlled insertion regioselectivity accelerates copolymerisation of ethylene with methyl acrylate by cationic bisphosphine monoxide–palladium catalysts. Chem Sci 7:737–744PubMed
42.
Zurück zum Zitat Sui X, Dai S, Chen C (2015) Ethylene polymerization and copolymerization with polar monomers by cationic phosphine phosphonic amide palladium complexes. ACS Catal 5:5932–5937 Sui X, Dai S, Chen C (2015) Ethylene polymerization and copolymerization with polar monomers by cationic phosphine phosphonic amide palladium complexes. ACS Catal 5:5932–5937
43.
Zurück zum Zitat Zhang Y, Cao Y, Leng X, Chen C, Huang Z (2014) Cationic palladium (II) complexes of phosphine–sulfonamide ligands: synthesis, characterization, and catalytic ethylene oligomerization. Organometallics 33:3738–3745 Zhang Y, Cao Y, Leng X, Chen C, Huang Z (2014) Cationic palladium (II) complexes of phosphine–sulfonamide ligands: synthesis, characterization, and catalytic ethylene oligomerization. Organometallics 33:3738–3745
44.
Zurück zum Zitat Schneider MJ, Schafer R, Mühaupt R (1997) Aminofunctional linear low density polyethylene via metallocene-catalysed ethene copolymerization with N,N-bis (trimethylsilyl)-1-amino-10-undecene. Polymer 38:2455–2459 Schneider MJ, Schafer R, Mühaupt R (1997) Aminofunctional linear low density polyethylene via metallocene-catalysed ethene copolymerization with N,N-bis (trimethylsilyl)-1-amino-10-undecene. Polymer 38:2455–2459
45.
Zurück zum Zitat Purgeti MD, Vogl O (1988) Functional polymers: polymerization of ω-alkenoate derivatives. J Polym Sci Part A Polym Chem 26:677–700 Purgeti MD, Vogl O (1988) Functional polymers: polymerization of ω-alkenoate derivatives. J Polym Sci Part A Polym Chem 26:677–700
46.
Zurück zum Zitat Kesti MR, Coates GW, Waymouth RM (1992) Homogeneous Ziegler–Natta polymerization of functionalized monomers catalyzed by cationic Group IV metallocenes. J Am Chem Soc 114:9679–9680 Kesti MR, Coates GW, Waymouth RM (1992) Homogeneous Ziegler–Natta polymerization of functionalized monomers catalyzed by cationic Group IV metallocenes. J Am Chem Soc 114:9679–9680
47.
Zurück zum Zitat Clark KJ (1970) Olefin copolymers containing polar groups and process for their preparation. US Patent 3949277 Clark KJ (1970) Olefin copolymers containing polar groups and process for their preparation. US Patent 3949277
48.
Zurück zum Zitat Langer A, Haynes R (1973) Copolymerization of alpha olefins with sterically hindered alkenyl amines using ziegler catalysts. US Patent 3755279 Langer A, Haynes R (1973) Copolymerization of alpha olefins with sterically hindered alkenyl amines using ziegler catalysts. US Patent 3755279
49.
Zurück zum Zitat Rix FC, Brookhart M (1995) Energetics of migratory insertion reactions in Pd(II) acyl ethylene, alkyl ethylene, and alkyl carbonyl complexes. J Am Chem Soc 117:1137–1138 Rix FC, Brookhart M (1995) Energetics of migratory insertion reactions in Pd(II) acyl ethylene, alkyl ethylene, and alkyl carbonyl complexes. J Am Chem Soc 117:1137–1138
50.
Zurück zum Zitat Younkin TR, Connor EF, Henderson JI, Friedrich SK, Grubbs RH, Bansleben DA (2000) Neutral, single-component nickel(II) polyolefin catalysts that tolerate heteroatoms. Science 287:460–462PubMed Younkin TR, Connor EF, Henderson JI, Friedrich SK, Grubbs RH, Bansleben DA (2000) Neutral, single-component nickel(II) polyolefin catalysts that tolerate heteroatoms. Science 287:460–462PubMed
51.
Zurück zum Zitat Ascenso R, Ribeiro AFG, Correia SG, Marques MM, Gomes PT, Dias AR, Blais M, Rausch MD, Chien JCW (1999) Polymerization with TMA-protected polar vinyl comonomers. II. Catalyzed by nickel complexes containing α-diimine-type ligands. J Polym Sci Part A Polym Chem 37:2471–2480 Ascenso R, Ribeiro AFG, Correia SG, Marques MM, Gomes PT, Dias AR, Blais M, Rausch MD, Chien JCW (1999) Polymerization with TMA-protected polar vinyl comonomers. II. Catalyzed by nickel complexes containing α-diimine-type ligands. J Polym Sci Part A Polym Chem 37:2471–2480
52.
Zurück zum Zitat Chung TC (2002) Synthesis of functional polyolefin copolymers with graft and block structures. Prog Polym Sci 27:39–85 Chung TC (2002) Synthesis of functional polyolefin copolymers with graft and block structures. Prog Polym Sci 27:39–85
53.
Zurück zum Zitat Jagur-Grodzinski J (1992) Modification of polymers under heterogeneous conditions. Prog Polym Sci 17:361–415 Jagur-Grodzinski J (1992) Modification of polymers under heterogeneous conditions. Prog Polym Sci 17:361–415
54.
Zurück zum Zitat Singh RP (1992) Surface grafting onto polypropylene-a survey of recent developments. Prog Polym Sci 17:251–281 Singh RP (1992) Surface grafting onto polypropylene-a survey of recent developments. Prog Polym Sci 17:251–281
55.
Zurück zum Zitat Duchateau J, Lutsen L, Guedens W, Cleij TJ, Vanderzande D (2010) Versatile post-polymerization functionalization of poly(p-phenylene vinylene) copolymers containing carboxylic acid substituents: development of a universal method towards functional conjugated copolymers. Polym Chem 1:1313–1322 Duchateau J, Lutsen L, Guedens W, Cleij TJ, Vanderzande D (2010) Versatile post-polymerization functionalization of poly(p-phenylene vinylene) copolymers containing carboxylic acid substituents: development of a universal method towards functional conjugated copolymers. Polym Chem 1:1313–1322
56.
Zurück zum Zitat Goldmann AS, Glassner M, Inglis AJ, Kowollik CB (2013) Post-functionalization of polymers via orthogonal ligation chemistry. Macromol Rapid Commun 34:810–849PubMed Goldmann AS, Glassner M, Inglis AJ, Kowollik CB (2013) Post-functionalization of polymers via orthogonal ligation chemistry. Macromol Rapid Commun 34:810–849PubMed
57.
Zurück zum Zitat Zhou H, Plummer CM, Li H, Huang H, Ma P, Li L, Liu L, Chen Y (2019) Regioselective post-functionalization of isotactic polypropylene by amination in the presence of N-hydroxyphthalimide. Polym Chem 10:619–626 Zhou H, Plummer CM, Li H, Huang H, Ma P, Li L, Liu L, Chen Y (2019) Regioselective post-functionalization of isotactic polypropylene by amination in the presence of N-hydroxyphthalimide. Polym Chem 10:619–626
58.
Zurück zum Zitat Ittel SD, Johnson LK, Brookhart M (2000) Late-metal catalysts for ethylene homo-and copolymerization. Chem Rev 100:1169–1204PubMed Ittel SD, Johnson LK, Brookhart M (2000) Late-metal catalysts for ethylene homo-and copolymerization. Chem Rev 100:1169–1204PubMed
59.
Zurück zum Zitat Chen CL (2018) Designing catalysts for olefin polymerization and copolymerization: beyond electronic and steric tuning. Nat Rev Chem 2:6–14 Chen CL (2018) Designing catalysts for olefin polymerization and copolymerization: beyond electronic and steric tuning. Nat Rev Chem 2:6–14
60.
Zurück zum Zitat Johnson LK, Dobbs K, Hauptman E, Lonkin A, Ittel S, McCord E, McLain SJ, Yin Z, Wang Y, Brookhart M (2002) Presented at the American Chemical Society Meeting, Orlando, FL Johnson LK, Dobbs K, Hauptman E, Lonkin A, Ittel S, McCord E, McLain SJ, Yin Z, Wang Y, Brookhart M (2002) Presented at the American Chemical Society Meeting, Orlando, FL
61.
Zurück zum Zitat McLain SJ, Sweetman KJ, Johnson LK, McCord EF (2002) Presented at the American Chemical Society Meeting, Orlando, FL McLain SJ, Sweetman KJ, Johnson LK, McCord EF (2002) Presented at the American Chemical Society Meeting, Orlando, FL
62.
Zurück zum Zitat Makovetsky KL, Finkelshtein ES, Bykov VI, Bagdasaryan AK, Goodall BL, Rhodes LF (1998) Method for preparation of copolymers of ethylene/norbornene-type monomers with nickel catalysts. US Patent 5(929):181A Makovetsky KL, Finkelshtein ES, Bykov VI, Bagdasaryan AK, Goodall BL, Rhodes LF (1998) Method for preparation of copolymers of ethylene/norbornene-type monomers with nickel catalysts. US Patent 5(929):181A
63.
Zurück zum Zitat Connor EF, Younkin TR, Henderson JI, Hwang S, Grubbs RH, Roberts WP, Litzau JJ (2002) Linear functionalized polyethylene prepared with highly active neutral Ni(II) complexes. J Polym Sci Part A Polym Chem 40:2842–2854 Connor EF, Younkin TR, Henderson JI, Hwang S, Grubbs RH, Roberts WP, Litzau JJ (2002) Linear functionalized polyethylene prepared with highly active neutral Ni(II) complexes. J Polym Sci Part A Polym Chem 40:2842–2854
64.
Zurück zum Zitat Leibfarth FA, Schneider Y, Lynd NA, Schultz A, Moon B, Kramer EJ, Bazan GC, Hawker CW (2010) Ketene functionalized polyethylene: control of cross-link density and material properties. J Am Chem Soc 132:14706–14709PubMed Leibfarth FA, Schneider Y, Lynd NA, Schultz A, Moon B, Kramer EJ, Bazan GC, Hawker CW (2010) Ketene functionalized polyethylene: control of cross-link density and material properties. J Am Chem Soc 132:14706–14709PubMed
65.
Zurück zum Zitat Takeuchi D, Chiba Y, Takano S, Osakada K (2013) Double-decker-type dinuclear nickel catalyst for olefin polymerization: Efficient incorporation of functional co-monomers. Angew Chem 125:12768–12772 Takeuchi D, Chiba Y, Takano S, Osakada K (2013) Double-decker-type dinuclear nickel catalyst for olefin polymerization: Efficient incorporation of functional co-monomers. Angew Chem 125:12768–12772
66.
Zurück zum Zitat Radlauer MR, Buckley AK, Henling LM, Agapie T (2013) Bimetallic coordination insertion polymerization of unprotected polar monomers: copolymerization of amino olefins and ethylene by dinickel bisphenoxyiminato catalysts. J Am Chem Soc 135:3784–3787PubMed Radlauer MR, Buckley AK, Henling LM, Agapie T (2013) Bimetallic coordination insertion polymerization of unprotected polar monomers: copolymerization of amino olefins and ethylene by dinickel bisphenoxyiminato catalysts. J Am Chem Soc 135:3784–3787PubMed
67.
Zurück zum Zitat Guo L, Dai S, Sui X, Chen C (2016) Palladium and nickel catalyzed chain walking olefin polymerization and copolymerization. ACS Catal 6:428–441 Guo L, Dai S, Sui X, Chen C (2016) Palladium and nickel catalyzed chain walking olefin polymerization and copolymerization. ACS Catal 6:428–441
68.
Zurück zum Zitat Zhong L, Li G, Liang G, Gao H, Wu Q (2017) Enhancing thermal stability and living fashion in α-diimine–nickel-catalyzed (co)polymerization of ethylene and polar monomer by increasing the steric bulk of ligand backbone. Macromolecules 50:2675–2682 Zhong L, Li G, Liang G, Gao H, Wu Q (2017) Enhancing thermal stability and living fashion in α-diimine–nickel-catalyzed (co)polymerization of ethylene and polar monomer by increasing the steric bulk of ligand backbone. Macromolecules 50:2675–2682
69.
Zurück zum Zitat Cheng H, Su Y, Hu Y, Zhang X, Cai Z (2018) Ethylene polymerization and copolymerization with polar monomers using nickel complexes bearing anilinobenzoic acid methyl ester ligand. Polymers 10:754–763PubMedCentral Cheng H, Su Y, Hu Y, Zhang X, Cai Z (2018) Ethylene polymerization and copolymerization with polar monomers using nickel complexes bearing anilinobenzoic acid methyl ester ligand. Polymers 10:754–763PubMedCentral
70.
Zurück zum Zitat Xia J, Zhang Y, Zhang J, Jian Z (2019) High-performance neutral phosphine-sulfonate nickel(II) catalysts for efficient ethylene polymerization and copolymerization with polar monomers. Organometallics 38:1118–1126 Xia J, Zhang Y, Zhang J, Jian Z (2019) High-performance neutral phosphine-sulfonate nickel(II) catalysts for efficient ethylene polymerization and copolymerization with polar monomers. Organometallics 38:1118–1126
71.
Zurück zum Zitat Gao J, Yang B, Chen C (2019) Sterics versus electronics: Imine/phosphine-oxide-based nickel catalysts for ethylene polymerization and copolymerization. J Catal 369:233–238 Gao J, Yang B, Chen C (2019) Sterics versus electronics: Imine/phosphine-oxide-based nickel catalysts for ethylene polymerization and copolymerization. J Catal 369:233–238
72.
Zurück zum Zitat Mecking S, Johnson LK, Wang L, Brookhart M (1998) Mechanistic studies of the palladium-catalyzed copolymerization of ethylene and α-olefins with methyl acrylate. J Am Chem Soc 120:888–899 Mecking S, Johnson LK, Wang L, Brookhart M (1998) Mechanistic studies of the palladium-catalyzed copolymerization of ethylene and α-olefins with methyl acrylate. J Am Chem Soc 120:888–899
73.
Zurück zum Zitat Drent E, van Dijk R, van Ginkel R, van Oort B, Pugh RI (2002) Palladium catalysed copolymerisation of ethene with alkylacrylates: polar comonomer built into the linear polymer chain. Chem Commun 31:744–745 Drent E, van Dijk R, van Ginkel R, van Oort B, Pugh RI (2002) Palladium catalysed copolymerisation of ethene with alkylacrylates: polar comonomer built into the linear polymer chain. Chem Commun 31:744–745
74.
Zurück zum Zitat Hearley AK, Nowack J, Rieger B (2005) New single-site palladium catalysts for the nonalternating copolymerization of ethylene and carbon monoxide. Organometallics 24:2755–2763 Hearley AK, Nowack J, Rieger B (2005) New single-site palladium catalysts for the nonalternating copolymerization of ethylene and carbon monoxide. Organometallics 24:2755–2763
75.
Zurück zum Zitat Skupov KM, Marella PR, Simard M, Yap GPA, Allen N, Conner D, Goodall BL, Claverie JP (2007) Palladium aryl sulfonate phosphine catalysts for the copolymerization of acrylates with ethene. Macromol Rapid Commun 28:2033–2038 Skupov KM, Marella PR, Simard M, Yap GPA, Allen N, Conner D, Goodall BL, Claverie JP (2007) Palladium aryl sulfonate phosphine catalysts for the copolymerization of acrylates with ethene. Macromol Rapid Commun 28:2033–2038
76.
Zurück zum Zitat Kochi T, Noda S, Yoshimura K, Nozaki K (2007) Formation of linear copolymers of ethylene and acrylonitrile catalyzed by phosphine sulfonate palladium complexe. J Am Chem Soc 129:8948–8949PubMed Kochi T, Noda S, Yoshimura K, Nozaki K (2007) Formation of linear copolymers of ethylene and acrylonitrile catalyzed by phosphine sulfonate palladium complexe. J Am Chem Soc 129:8948–8949PubMed
77.
Zurück zum Zitat Weng W, Shen Z, Jordan RF (2007) Copolymerization of ethylene and vinyl fluoride by (phosphine-sulfonate) Pd (Me)(py) catalysts. J Am Chem Soc 129:15450–15451PubMed Weng W, Shen Z, Jordan RF (2007) Copolymerization of ethylene and vinyl fluoride by (phosphine-sulfonate) Pd (Me)(py) catalysts. J Am Chem Soc 129:15450–15451PubMed
78.
Zurück zum Zitat Borkar S, Newsham DK, Sen A (2008) Copolymerization of ethene with styrene derivatives, vinyl ketone, and vinylcyclohexane using a (phosphine–sulfonate)palladium(II) system: unusual functionality and solvent tolerance. Organometallics 27:3331–3334 Borkar S, Newsham DK, Sen A (2008) Copolymerization of ethene with styrene derivatives, vinyl ketone, and vinylcyclohexane using a (phosphine–sulfonate)palladium(II) system: unusual functionality and solvent tolerance. Organometallics 27:3331–3334
79.
Zurück zum Zitat Ito S, Munakata K, Nakamura A, Nozaki K (2009) Copolymerization of vinyl acetate with ethylene by palladium/alkylphosphine–sulfonate catalysts. J Am Chem Soc 131:14606–14607PubMed Ito S, Munakata K, Nakamura A, Nozaki K (2009) Copolymerization of vinyl acetate with ethylene by palladium/alkylphosphine–sulfonate catalysts. J Am Chem Soc 131:14606–14607PubMed
80.
Zurück zum Zitat Shen Z, Jordan RF (2010) Copolymerization of ethylene and vinyl fluoride by (phosphine-bis (arenesulfonate)) PdMe (pyridine) catalysts: insights into inhibition mechanisms. Macromolecules 43:8706–8708 Shen Z, Jordan RF (2010) Copolymerization of ethylene and vinyl fluoride by (phosphine-bis (arenesulfonate)) PdMe (pyridine) catalysts: insights into inhibition mechanisms. Macromolecules 43:8706–8708
81.
Zurück zum Zitat Rünzi T, Fröhlich D, Mecking S (2010) Direct synthesis of ethylene–acrylic acid copolymers by insertion polymerization. J Am Chem Soc 132:17690–17691PubMed Rünzi T, Fröhlich D, Mecking S (2010) Direct synthesis of ethylene–acrylic acid copolymers by insertion polymerization. J Am Chem Soc 132:17690–17691PubMed
82.
Zurück zum Zitat Kryuchkov VA, Daigle JC, Skupov KM, Claverie JP, Winnik FM (2010) Amphiphilic polyethylenes leading to surfactant-free thermoresponsive nanoparticles. J Am Chem Soc 132:15573–15579PubMed Kryuchkov VA, Daigle JC, Skupov KM, Claverie JP, Winnik FM (2010) Amphiphilic polyethylenes leading to surfactant-free thermoresponsive nanoparticles. J Am Chem Soc 132:15573–15579PubMed
83.
Zurück zum Zitat Ravasio A, Boggioni L, Tritto I (2011) Copolymerization of ethylene with norbornene by neutral aryl phosphine sulfonate palladium catalyst. Macromolecules 44:4180–4186 Ravasio A, Boggioni L, Tritto I (2011) Copolymerization of ethylene with norbornene by neutral aryl phosphine sulfonate palladium catalyst. Macromolecules 44:4180–4186
84.
Zurück zum Zitat Li H, Li L, Marks TJ (2004) Polynuclear olefin polymerization catalysis: proximity and cocatalyst effects lead to significantly increased polyethylene molecular weight and comonomer enchainment level. Angew Chem 116:5045–5048 Li H, Li L, Marks TJ (2004) Polynuclear olefin polymerization catalysis: proximity and cocatalyst effects lead to significantly increased polyethylene molecular weight and comonomer enchainment level. Angew Chem 116:5045–5048
85.
Zurück zum Zitat Dai S, Sui X, Chen C (2015) Highly robust palladium(II) α-diimine catalysts for slow-chain-walking polymerization of ethylene and copolymerization with methyl acrylate. Angew Chemie Int Ed 54:9948–9953 Dai S, Sui X, Chen C (2015) Highly robust palladium(II) α-diimine catalysts for slow-chain-walking polymerization of ethylene and copolymerization with methyl acrylate. Angew Chemie Int Ed 54:9948–9953
86.
Zurück zum Zitat Chen Z, Liu W, Daugulis O, Brookhart M (2016) Mechanistic studies of Pd(II)-catalyzed copolymerization of ethylene and vinylalkoxysilanes: Evidence for a β-silyl elimination chain transfer mechanism. J Am Chem Soc 138:16120–16129PubMed Chen Z, Liu W, Daugulis O, Brookhart M (2016) Mechanistic studies of Pd(II)-catalyzed copolymerization of ethylene and vinylalkoxysilanes: Evidence for a β-silyl elimination chain transfer mechanism. J Am Chem Soc 138:16120–16129PubMed
87.
Zurück zum Zitat Tao W, Akita S, Nakano R, Ito S, Hoshimoto Y, Ogoshi S, Nozaki K (2017) Copolymerisation of ethylene with polar monomers by using palladium catalysts bearing an N-heterocyclic carbene–phosphine oxide bidentate ligand. Chem Commun 53:2630–2633 Tao W, Akita S, Nakano R, Ito S, Hoshimoto Y, Ogoshi S, Nozaki K (2017) Copolymerisation of ethylene with polar monomers by using palladium catalysts bearing an N-heterocyclic carbene–phosphine oxide bidentate ligand. Chem Commun 53:2630–2633
88.
Zurück zum Zitat Zhai F, Solomon JB, Jordan RF (2017) Copolymerization of ethylene with acrylate monomers by amide-functionalized α-diimine Pd catalysts. Organometallics 36:1873–1879 Zhai F, Solomon JB, Jordan RF (2017) Copolymerization of ethylene with acrylate monomers by amide-functionalized α-diimine Pd catalysts. Organometallics 36:1873–1879
89.
Zurück zum Zitat Ding L, Cheng H, Li Y, Tanaka R, Shiono T, Cai Z (2018) Efficient ethylene copolymerization with polar monomers using palladium anilinonaphthoquinone catalysts. Polym Chem 9:5476–5482 Ding L, Cheng H, Li Y, Tanaka R, Shiono T, Cai Z (2018) Efficient ethylene copolymerization with polar monomers using palladium anilinonaphthoquinone catalysts. Polym Chem 9:5476–5482
90.
Zurück zum Zitat Ye J, Mu H, Wang Z, Jian Z (2019) Heteroaryl backbone strategy in bisphosphine monoxide palladium-catalyzed ethylene polymerization and copolymerization with polar monomers. Organometallics 38:2990–2997 Ye J, Mu H, Wang Z, Jian Z (2019) Heteroaryl backbone strategy in bisphosphine monoxide palladium-catalyzed ethylene polymerization and copolymerization with polar monomers. Organometallics 38:2990–2997
Metadaten
Titel
Ni/Pd-catalyzed coordination-insertion copolymerization of ethylene with alkyl acrylate
verfasst von
Urmilla Baruah
Prakash J. Saikia
Shashi D. Baruah
Publikationsdatum
13.12.2019
Verlag
Springer Berlin Heidelberg
Erschienen in
Polymer Bulletin / Ausgabe 11/2020
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-019-03055-9

Weitere Artikel der Ausgabe 11/2020

Polymer Bulletin 11/2020 Zur Ausgabe

    Marktübersichten

    Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.