Vinyl polymerization. III. Polymerization of acenaphthylene

Imoto, Minoru; Takemoto, Kiichi

doi:10.1002/pol.1955.120157922

Cited by 26 publications

(5 citation statements)

References 7 publications

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“…Jones [3] and Flowers and Miller [4], for example, have conducted extensive investigations. The only paper on the mechanism of this polymerization was by Imoto and Takemoto [5], using boron trifluoride etherate as an initiator. It should be emphasized that very little was done to measure molecular weights of these polymers [6] and no reference to possible stereoregularity was found.…”

Section: Introductionmentioning

confidence: 99%

Stereoregularity in ionic polymerization of acenaphthylene

Story¹,

Canty²

1964

J. RES. NATL. BUR. STAN. SECT. A.

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(Novc mbcr 15, 1963) F our distinct polym.crs wc rc isolated fr om t he p olym eri zat ions of accnaph Lh.v lcnc ill it iated by boron t rifiu oride a nd n-butyllithium. A syn d iotactic or isotactic co nform atio n was assigned to t h ese prod ucts on t he basis of infrared a nd N M R evidence. T he conformat ions and reaction details a re di sc ussed. I . IntroductionA survey of the fi eld of ster eor egulm' polym ers indicated th at little h as been don e in delib er at e control of chain conformation by mea ns of steric hindmn ce of bulky groups [1] .1.2 In t his sense, acenap hLl1 ylene as a vin yl mon om er Wt1S parli culnrly int eresLin g du e Lo the extreme bulk fi nd rigidit y of the 1 ,8 -pel"in~tph t h yle n e residue. Addition al feftt ures wer e its slm in ed five -mem bered ring [b ] and well defin ed co nditi ons for polYllleri zfl tio li.Th e polymers of ftcenflpil thylene h ftve been exte nsively investi gated. D ziewonski and his coworke rs [2] we re able to show iO llic, therm ftl, ftll d solicl-st~l te polymerizat ion of ace lHlphlhylene before t he prese nt-day tools for m easuring Jl igh molecular weights were available. Their investigl1tio ns started in 1912 rmel ended in ] 924. Since then, oL her work· ers have examin ed these polymers. Jones '.:vote adclecl ill proof: The paper by G. Nalla, G . Dall' Asta, G. M azzanti, ancl G . Metroni (Mukro11l01. Cilelll. 69 , 124, 1963) describes the polymerization of cyclobutcnc with Ziegler cMa lysts. The ste reochemistry of t hc products arc ap parently identical with the case described hero. Instead of cis or trans, the nomenclature tILTeo or eTl/tltro, rrs pcctivl'iy, is used. 165th e plftl1e of t.he papcr a,nd tll e B 's are ill fl p ara llel plan e b elow, was self-termin ati ng . Ri ll g Jormat.ion was fftvo red . I n fact, both a cyclic trimer and tetranw r ftre kn own [2}. The cis-sy ndiolactic p olymer II was impossible to con str uct beyond th e Lrimer. IIT he Silme nolation is used here ,1S for J ~lbove.The A's werc acLuftlly Lwisled out of plane due Lo storic hindrance. trans-Iso tactic poJ~-acenaphLhy lene, lIT , for med a helix. 3 III 3 'r'he limited rotation about the back bone carbon-carbon bonds due to stcric hind rance of the 1,8-acenaphthylcnc residues suggests that change in the se nse of the helix of III is not possible if a penultimate effect in fl uences the course of add ition. Of course, a mixture of d a nd 1 cha ins would be produced, unless a n assynlctric initiator wcro used.

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Section: Introductionmentioning

confidence: 99%

Stereoregularity in ionic polymerization of acenaphthylene

Story¹,

Canty²

1964

J. RES. NATL. BUR. STAN. SECT. A.

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“…It is conceivable that BPO in the triphenylamine/BPO binary system is decomposed according to eqs. (1) and (2). Thermal decomposition of BPO by amine~*~~~''-~ is known to proceed through the complex formation shown in eq.…”

Section: Photodecomposition Of Bpomentioning

confidence: 99%

“…Thermal decomposition of BPO by amine~*~~~''-~ is known to proceed through the complex formation shown in eq. (1). It is supposed, on the other hand, that the decomposition in anthracene/BPO binary system is initiated by energy transfer2' from anthracene to It has been reported that the photodecomposition of acetyl peroxiden is facilitated by anthracene and naphthalene.…”

Section: Photodecomposition Of Bpomentioning

confidence: 99%

Effect of binary sensitizers on photografting of methacrylic acid on low-density polyethylene film

Ogiwara

Kobayashi

Kubota

1986

J. Polym. Sci. C Polym. Lett.

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“…mally but a t a substantially slower rate. [3][4][5][6][7][8][9][10][11] Liquid acenaphthylene is known to polymerize ther-…”

Section: Temperature Dependencementioning

confidence: 99%

Solid‐state polymerization of acenaphthylene induced by ionizing radiation

Chen¹

1962

J. Polym. Sci.

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The polymerization and copolymerization of acenaphthylene in solution or melt nitiate d by free-radical, ionic, and Ziegler catalysts have been reported in the literature.l-12 Acenaphthylene is a yellow crystalline material (m.p. 92OC.) having the following structure:This material offers interesting possibilities as a monomer for solid-state polymerization studies. The polymerization reaction should be capable of being initiated readily and most advantageously by irradiation techniques.The polymerization of acenaphthylene in the solid state initiated by x-rays has been undertaken in air, under nitrogen, and in vacuum. Both commercial and recrystallized acenaphthylene have been used. A General Electric Maxitron 250 was employed as the x-ray source; no filtration was used. Acenaphthylene was irradiated in tablet form (diameter, 2.83 cm.; thic!cness, 0.14 cm.; approximate weight 1 g.), placed at a distance of 5 cm. from the target to the top of the tablet. Different dose rates were obtained by varying the current (6-30 ma., 250 Itvp). Dose rates were calculated from Fe++-Fe3+ dosimetry, the size, thicltness, and density of the samples being taken into consideration. Dose rates of 0.824.1 x 106 rad/hr. were employed. The results are summarized below. I. Total Dose Dependence(A dose rate of 4.1 x 106 rad/hr. was employed. Two series of experiments were carried out. In the first, acenaphthylene as received (Columbia Southern) was polymerized a t ambient temperature (2535°C.) in air. The results show (upper curve, Fig. 1) that the per cent polymerization versus total dose after an induction is directly porportional to the total dose. I n the second series of experiments, acenaphthylene as received waa recrystallized twice from methanol. It was then polymerized under

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Vinyl polymerization. III. Polymerization of acenaphthylene

Cited by 26 publications

References 7 publications

Stereoregularity in ionic polymerization of acenaphthylene

Stereoregularity in ionic polymerization of acenaphthylene

Effect of binary sensitizers on photografting of methacrylic acid on low-density polyethylene film

Solid‐state polymerization of acenaphthylene induced by ionizing radiation

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