Polymerization of 3,4‐dihydro‐2H‐carboxyaldehyde (acrolein dimer). Part II. Copolymerization with isocyanates

Kitahama, Yoshiharu; Ohama, Hiroshi; Kobayashi, Haruo

doi:10.1002/pol.1969.150070312

Cited by 7 publications

(2 citation statements)

References 3 publications

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“…copolymerization of acrolein dimer with methyl-, ethyl-, or phenyl isocyanate at 15 • C in toluene affords 1:1 copolymers (69). The copolymerization of ethylene oxide with aromatic isocyanates is conducted in toluene at −78 • C, using triethylaluminum as initiator.The shown acetal structure 11 is proposed for the copolymer (70).…”

Section: Isocyanate-derived Polymersmentioning

confidence: 99%

Isocyanate‐Derived Polymers

Ulrich

2002

Encyclopedia of Polymer Science and Technology

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Homo‐ and copolymers derived from mono‐ and diisocyanates are treated in this article. Also, addition, condensation, and addition/condensation polymers derived from diisocyanates are included. Of commercial interest are segmented block copolyamide elastomers produced from methylene di‐ p ‐phenylene isocyanate (MDI) and macrodicarboxylic acids and dicarboxylic acids. This reaction polymerization is conducted in a vented extruder or in solution. Also, engineering plastics are obtained from diisocyanates and dicarboxylic acids. Poly(amide imides) and poly(imides) are produced from MDI and TDI (toluene diisocyanate) and trimellitic acid anhydride and isophthalic acid and dianhydrides, respectively. Heterocyclic polymers with useful high temperature properties made from MDI and suitable monomers by a polyaddition/condensation reaction are also included.

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Section: Isocyanate-derived Polymersmentioning

confidence: 99%

Isocyanate‐Derived Polymers

Ulrich

2002

Encyclopedia of Polymer Science and Technology

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“…Also, block copolymers with a random-coil segment and a helical segment would be interesting materials in their own right. There have been only a few examples of the preparation block, 16,31 random, 32 and alternating 33 copolymers of monoisocyanates with other monomers.…”

Section: Block Copolymers Of N-hexylmentioning

confidence: 99%

Organotitanium(IV)-Catalyzed Cyclopolymerizations of 1,2-Diisocyanates and Cyclocopolymerizations of Monoisocyanates with 1,2-Diisocyanates

Patten

Novak

1996

Macromolecules

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1,2-Diisocyanates were cyclopolymerized using CpTiCl2N(CH3)2. Treatment of 1,2-diisocyanatodecane with CpTiCl2N(CH3)2 in THF effected its cyclopolymerization with stoichiometric control over molecular weight and with M w/M n ranging from 1.2 to 1.8. IR, 1H NMR, and 13C NMR spectra of the resulting polymers indicate that the monomer underwent complete cyclization. Studies of the solution properties of poly(1,2-diisocyanatodecane) showed that it maintains a smaller hydrodynamic volume than poly(n-hexyl isocyanate) at equivalent molecular weights. Living poly(n-hexyl isocyanate) was end-capped with blocks of poly(1,2-diisocyanatopropane) and poly(1,2-diisocyanatodecane). TGA and DSC studies of these block copolymers showed that the individual block segments decomposed at the same temperatures as their respective homopolymers. Random copolymerizations of n-hexyl isocyanate with 1,2-diisocyanatopropane and 1,2-diisocyanatodecane were conducted. TGA studies of these macromolecules showed that the decomposition temperature of the copolymer was a function of its 1,2-diisocyanate content, and the incorporation of a relatively high mole percent of the diisocyanate monomer was necessary to observe an increase in the decomposition onset of the copolymer.

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Polymerization of β‐cyanopropionaldehyde. IX. Anionic copolymerization with phenyl isocyanate

Hashimoto

Sumitomo

1971

J. Polym. Sci. A‐1 Polym. Chem.

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MaterialsCPA, tetrahydrofuran (THF), and benzophenone (BzPh) were purified as already described.23 PhI was distilled in vacuo after a careful removal of moisture. LirBzPh and the cyclic trimer of CPA, 2,4,6-tris(@-cyanoethyl)-s-trioxane, were prepared in the same way as described in the preceding paper^.^*^^ 3-Phenyloxazolidone-2 and 2-Nphenylimino-1,3-dioxolane were prepared according to methods described elsewhere.24.s PolymerizationA cold solution of CPA and PhI in T H F was added to a THF solution of Liz-BzPh with vigorous stirring. Termination was carried out by adding a small amount of methanol directly into the polymerization system. The resulting copolymer was washed with alarge amount of methanol and dried under reduced pressure. The average molecular weight of the polymer a,, was measured by vapor-pressure osmometry (HewIett-Packard Model 302) in dimethylformamide (DMF) a t 37°C. Structural Analyses of the CopolymersInfrared spectra of the copolymers were measured by the KBr method by using a Hitachi grating infrared spectrophotometer, Model 215. NMR analysis was made in deuterated chloroform with a JNM-4H-100 spectrometer. RESULTS AND DISCUSSIONThe results of copolymerization of CPA with PhI with use of Liz-BzPh are given in Tables I and 11.

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Polymerization of 3,4‐dihydro‐2H‐carboxyaldehyde (acrolein dimer). Part II. Copolymerization with isocyanates

Cited by 7 publications

References 3 publications

Isocyanate‐Derived Polymers

Isocyanate‐Derived Polymers

Organotitanium(IV)-Catalyzed Cyclopolymerizations of 1,2-Diisocyanates and Cyclocopolymerizations of Monoisocyanates with 1,2-Diisocyanates

Polymerization of β‐cyanopropionaldehyde. IX. Anionic copolymerization with phenyl isocyanate

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