Synthesis and investigation of ?,?-methacryloyl terminated epoxide-amine macromonomers

Klee, Joachim E.; Claußen, F.; Hörhold, Hans‐Heinrich; Raddatz, Joachim

doi:10.1007/bf00300598

Cited by 6 publications

(1 citation statement)

References 14 publications

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“…We recently reported on new types of a,@-methacryloyl terminated epoxide-amine macromonomers [5,6]. In this paper we will describe the formation of apmethacryloyl terminated macromonomers containing epoxide-carboxylic acid repetitive units and epoxide-phenol repetitive units, respectively.…”

Section: Introductionmentioning

confidence: 98%

Synthesis and investigation of α,ω‐methacryloyl poly (epoxide‐carboxylic acid) and α,ω‐methacryloyl poly (epoxide‐phenol) macromonomers

Klee¹,

Claußen²,

Hörhold³

1993

Acta Polymerica

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a,o-methacryloyl terminated macromonomers containing epoxide-carboxylic acid and epoxide-phenolic repetitive units were synthesised. They were prepared in the molecular range from 600 to 2000 g/mol by a two-step reaction. At first prepolymers were formed from bisphenol-A diglycidyl ether and carboxylic acids or phenols and then reacted in a second step with methacrylic acid to the macromonomers.Their structure is proved by elemental analysis,Mi, (vpo)values,IRand NMR spectroscopy. By using HPLC and G P C analysis it was shown that the macromonomers consist ofoligomer homologous series. The distribution of the oligomers agrees with the calculated ones. Furthermore HPLC analysis and NMR spectra show that the epoxide rings were opened by SKIand S,,-type reactions. Synthese und Untersuchung von a,o-methacryloyl terminierten Poly(epoxid-curbonsatire)-und a,o-methacryloyl terminierten Poly(epoxid-phenol)-Macromonomeren a,w-methacryloyl terminierte Macromonomere M-1 und M-2 mit Epoxid-Carbonsaure bzw. Epoxid-Phenol-Repetiereinheiten werden in einer zweistufigen Umsetzung hergestellt. In einem ersten Schritt werden aus Bisphenol-A-diglycidylether und Carbonsaure bzw. Phenol Prepolymere erhalten, die mit Methacrylsaure terminiert werden. Die Struktur von M-1 und M-2 ist durch Elementaranalyse, MJvpo) Werte, IR-und NMR-Spektren belegt. Mittels HPLC und G PC-Analyse wird gezeigt, daR die Macromonomere aus Serien von Oligomerhomologen bestehen, deren Verteilung mit berechneten Werten iibereinstimmt. Anhand von HPLC und NMR-Spektren ist die Epoxidringoffnung nach SN,und SNz-Reaktionen nachweisbar.

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Section: Introductionmentioning

confidence: 98%

Synthesis and investigation of α,ω‐methacryloyl poly (epoxide‐carboxylic acid) and α,ω‐methacryloyl poly (epoxide‐phenol) macromonomers

Klee¹,

Claußen²,

Hörhold³

1993

Acta Polymerica

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Telechelic prepolymers and macromonomers by step growth processes

Klee

1994

Acta Polymerica

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Dedicated to Prof. Hans-Heinrich Horhold on the occasion of his 60th birthdayThe article describes recent achievements in the field oftelechelic epoxide-amine and epoxide-dithiol prepolymers and of macromonomers which can be obtained by step growth processes of epoxides with amines, carboxylic acids or phenols. The distribution of the oligomers is investigated with the help of HPLC and GPC. Furthermore the reaction of epoxideamine prepolymers with cyclic carboxylic acid anhydrides is described as well as their polymerization to new hybrid networks. The prepolymers with their P-hydroxypropyl structural units are able to form complexes with metal ions. We have used this property for the extraction of Cu" ions from water solutions.Klee

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Interpenetrating polymer networks derived from epoxide‐amine adducts in either polymer network

Klee¹,

Leube

Mülhaupt

1995

Angew. Makromol. Chem.

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A new type of interpenetrating polymer network was synthesized via photoinitiated free-radical polymerization of a,omethacryloyl terminated macromonomers prepared from epoxide-amine-adducts, followed by thermal addition polymerization of bisphenol-A diglycidyl ether and 4,4'-diaminodiphenylsulfone or 3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1 .0.2*6]decane. The interpenetrating polymer networks are optically transparent and show only one glass transition temperature ranging from -10 to 130"C, as a function of the macromonomer/addition polymer mixing ratio. The presence of a single phase was confirmed by scanning electron microscopy (SEM). ZUSAMMENFASSUNGEin neuer Typ eines interpenetrierenden Polymer-Netzwerkes (IPN) wurde durch radikalische (photochemische) Polymerisation von a,omethacryloyl-terminierten Epoxid-Amin-Makromonomeren, kombiniert mit nachfolgender thermischer Additionspolymerisation von Bisphenol-A-diglycidylether und 3(4),8(9)-Bis(aminomethy1) tricyclo[5.2.1 .0.2*6]decan bzw. 4,4'-Diaminodiphenylsulfon, erhalten. Die interpenetrierenden Polymer-Netzwerke weisen, in Abhangigkeit vom Anteil des Makromonomeren und des Additionspolymeren, nur eine Glasubergangstemperatur zwischen -10 und 130 "C auf. Die IPN sind optisch klar und zeigen auch im Rasterelektronenmikroskop (REM) keine Phasenseparation.CCC OOO3-3146/95/$07.00 4a-4c and 5a-5g and of the homopolymers 3f, 3g, 5f and 5g. Glass transition temperaturesGlass transition temperatures Polymer by DMA by DSC Polymer by DMA by DSC network

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Synthesis and investigation of ?,?-methacryloyl terminated epoxide-amine macromonomers

Cited by 6 publications

References 14 publications

Synthesis and investigation of α,ω‐methacryloyl poly (epoxide‐carboxylic acid) and α,ω‐methacryloyl poly (epoxide‐phenol) macromonomers

Synthesis and investigation of α,ω‐methacryloyl poly (epoxide‐carboxylic acid) and α,ω‐methacryloyl poly (epoxide‐phenol) macromonomers

Telechelic prepolymers and macromonomers by step growth processes

Interpenetrating polymer networks derived from epoxide‐amine adducts in either polymer network

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