Addition polymerization of cyclobutene and bicyclobutane monomers

Hall, H. K.; Ykman, P.

doi:10.1002/pol.1976.230110101

Cited by 42 publications

(18 citation statements)

References 63 publications

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“…In this case the driving 1 repeat force for the ring-opening step is the formation of the aromatic ring. Hall and coworkers5 showed that derivatives of bicyclo[l.l.O]butane would polymerize by free radicals by cleavage of the highly strained…”

mentioning

confidence: 99%

Free Radical Ring-Opening Polymerization

Bailey

1985

Polym J

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Although unstrained five-or six-membered carbocyclic systems undergo free radical ring-closing polymerization, the introduction of an oxygen into the ring will promote free radical ring-opening polymerization, since the resulting carbon-oxygen double bond is approximately 50 kcal more stable than a carbon-carbon double bond. Thus, cyclic ketene acetals, cyclic ketene aminals, cyclic vinyl ethers, unsaturated spiro ortho carbonates, and unsaturated spiro ortho esters will all undergo free radical ring-opening polymerization. Copolymerization of these monomers with a wide variety of vinyl monomers will introduce an ester, amide, keto or carbonate group into the backbone of an addition polymer and can make possible the synthesis of functionally terminated oligomers, biodegradable addition polymers, thermally stable polymers, and monomers that expand on polymerization. KEY WORDS Free Radical Ring-Opening Polymerization I 2-Methylene-1 ,3-dioxepane 1 Polyesters I Functionally-terminated Oligomers I Unsaturated Spiro a-Carbonates I '\N+

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confidence: 99%

Free Radical Ring-Opening Polymerization

Bailey

1985

Polym J

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“…[2][3][4] Cyclobutane polymers, such as poly(1-cyanobicyclobutane), and its copolymers exhibit higher glass transition temperatures (T g ), melting points, and improved mechanical properties than their vinyl analogues. 1 The cyclobutane unit might also act as a "zipper-jamming" unit to suppress depolymerization in vinyl copolymers, such as with MMA.…”

Section: Introductionmentioning

confidence: 99%

“…1 This is due to the relief of ring strain energy providing a thermodynamic driving force for polymerization. This polymerization proceeds via opening of the -like central bond to give a high yield of a polymer containing exclusively 1,3-linked cyclobutane rings in its backbone.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and thermal characterization of poly(dimethyl bicyclobutane-1,3-dicarboxylate) and its copolymers

Choi

Yuan

Padías

et al. 1999

J. Polym. Sci. A Polym. Chem.

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“…Bicyclobutanes carrying electron‐withdrawing substituents at one or both bridgehead atoms are a family of monomers that readily undergo free‐radical homo‐ and copolymerization with vinyl monomers 10–13. This polymerization proceeds via opening of the strained π‐like 1,3‐bond to give a high yield of a polymer containing exclusively cyclobutane rings in its backbone.…”

Section: Introductionmentioning

confidence: 99%

“…This polymerization proceeds via opening of the strained π‐like 1,3‐bond to give a high yield of a polymer containing exclusively cyclobutane rings in its backbone. Polymers having ring repeat units in the backbone often import desirable physical properties for example, improved thermal, mechanical, optical, and piezoelectric properties to the materials 10–15. For example, bicyclobutane polymers do not undergo thermal depolymerization as does poly(methyl methacrylate) (PMMA).…”

Section: Introductionmentioning

confidence: 99%

Catheter closure of accessory pulmonary blood flow after bidirectional Glenn anastomosis using Amplatzer duct occluder

Ebeid

Gaymes

Joransen

2002

Cathet Cardio Intervent

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Additional source of pulmonary blood flow in patients with bidirectional cavopulmonary anastomosis (Glenn shunt) may cause elevation of the pulmonary artery pressure precluding safe completion of the Fontan operation. A case is presented with single-ventricle bidirectional cavopulmonary anastomosis and additional flow from the ventricle to the pulmonary artery resulting in elevated Glenn pressure. The communication was successfully occluded using Amplatzer duct occluder with satisfactory reduction in the Glenn pressure.

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Addition polymerization of cyclobutene and bicyclobutane monomers

Cited by 42 publications

References 63 publications

Free Radical Ring-Opening Polymerization

Free Radical Ring-Opening Polymerization

Synthesis and thermal characterization of poly(dimethyl bicyclobutane-1,3-dicarboxylate) and its copolymers

Catheter closure of accessory pulmonary blood flow after bidirectional Glenn anastomosis using Amplatzer duct occluder

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