Poly(<i>p</i>-xylylene) and Its Derivatives by Chemical Vapor Deposition:  Synthesis, Mechanism, and Structure

Simon, Peter F. W.; Mang, Stefan; Hasenhindl, A.; Gronski, W.; Greiner, Andreas

doi:10.1021/ma9808070

Cited by 49 publications

(32 citation statements)

References 11 publications

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“…In the case of the CVD process, the generation of gaseous p-xylylene can be achieved, for example, by direct pyrolysis of p-xylene 6,61) , the thermal cleavage of [2.2]paracyclophane 10) , or the thermal conversion of ahalo-1,4-xylene 22) or diesters of a,a9-dihydroxy-1,4-xylene 11,65) . The formation of p-xylylene in solution can be accomplished by the procedure of Gilch and Wheelwright 21,62) , where an a-halo-1,4-xylene in solution is treated with base.…”

Section: Generalmentioning

confidence: 99%

Poly(p-phenylene alkylene)s – A forgotten class of polymers

Steiger

Tervoort

Weder³

et al. 2000

Macromol. Rapid Commun.

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Within the wealth of hydrocarbon polymers, poly(p‐phenylene alkylene)s (“alkarotics”) hold a special position since they have been a long forgotten class of hydrophobic polymers. This is somewhat surprising, since the cornerstones of this polymer family cover extremely broad materials properties and the few known representatives attract attention with very favorable characteristics. In the course of this article, four new representatives of this family are presented. Whereas poly(p‐phenylene octylene) (PPPO; 90°C), poly(p‐phenylene hexylene) (PPPH; 120°C) and poly(p‐phenylene propylene) (PPPPr; 110–130°C) have surprisingly low melting temperatures, the highly crystalline poly(p‐phenylene butylene) (PPPB), melting between 200 and 225°C, meets many of the requirements that are essential for a novel, hydrophobic, processable, engineering polymer. In connection with the efforts to tailor the melting temperature of these polymers, a simple, semi‐empirical methodology to estimate melting temperatures of unknown representatives of homologous series of polymers was developed and verified. By means of this approach, the melting temperatures of PPPH and PPPB could be predicted with remarkable accuracy. In addition, it was shown that the method is not restricted to the present alkarotic polymers, but it seems to have a rather broad range of applications as shown by the successful description of the polymer series, including various liquid‐crystalline hydrocarbon polymers and different polyamides.

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Section: Generalmentioning

confidence: 99%

Poly(p-phenylene alkylene)s – A forgotten class of polymers

Steiger

Tervoort

Weder³

et al. 2000

Macromol. Rapid Commun.

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“…However, the monomeric species must be volatile. Vapor phase processes can be classified depending on the deposition mechanism: chain growth (e.g., plasma enhanced chemical vapor deposition, PECVD7, 8) and step growth polymerization (e.g., vapor deposition polymerization, VDP9 or CVD grown parylene6, 10). Chain growth and step growth mechanisms have been demonstrated also for initiated CVD (iCVD) and oxidative CVD (oCVD), respectively.…”

Section: Introductionmentioning

confidence: 99%

25th Anniversary Article: CVD Polymers: A New Paradigm for Surface Modifi cation and Device Fabrication

et al. 2013

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Well-adhered, conformal, thin (<100 nm) coatings can easily be obtained by chemical vapor deposition (CVD) for a variety of technological applications. Room temperature modification with functional polymers can be achieved on virtually any substrate: organic, inorganic, rigid, flexible, planar, three-dimensional, dense, or porous. In CVD polymerization, the monomer(s) are delivered to the surface through the vapor phase and then undergo simultaneous polymerization and thin film formation. By eliminating the need to dissolve macromolecules, CVD enables insoluble polymers to be coated and prevents solvent damage to the substrate. CVD film growth proceeds from the substrate up, allowing for interfacial engineering, real-time monitoring, and thickness control. Initiated-CVD shows successful results in terms of rationally designed micro- and nanoengineered materials to control molecular interactions at material surfaces. The success of oxidative-CVD is mainly demonstrated for the deposition of organic conducting and semiconducting polymers.

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“…Although α,α′‐dihydroxy‐ p ‐xylylenes,50, 51 α,α′‐ dibromo‐ p ‐xylylenes,52 α‐chloro‐ p ‐xylylenes,53 and α,α′‐diacetoxy‐ p ‐xylylenes54 provide potential candidates for functionalized poly( p ‐xylylene)s as they all have been shown to undergo CVD polymerization, substituted [2.2]paracyclophanes have been the preferred precursors for CVD polymerization—at least in our hands 55. Scheme summarizes the synthesis of [2.2]paracyclophanes with various functional groups.…”

Section: Cvd Polymerization Of Substituted [22]paracyclophanes: Reacmentioning

confidence: 99%

A re‐evaluation of fifteen years of european risk assessment using effect models

Laender¹,

Sprang²,

Janssen³

2013

Enviro Toxic and Chemistry

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Ecological risk assessments of chemicals can be informed by a suite of effect models, including population and food web models. In the risk assessments conducted under EU regulation 793/93/EC, however, applications of such effect models are extremely scarce and toxicity-extrapolation approaches are often used instead. The objective of the present study was to re-evaluate these risk assessments using two types of effect models: species sensitivity distributions (SSDs, non-mechanistic), and food web models (mechanistic). Species sensitivity distributions significantly fitted the available toxicity data for up to 35% of the chemicals, depending on the trophic levels included and the amount of data available. Median hazardous concentrations for 5% of the species (HC5-50) estimated by the SSDs were less accurate predictors of measured community-level no observed effect concentration than food web model-derived HC5-50s, albeit data were available for seven chemicals only. For datasets with more than 10 data points, the 90% confidence interval of the estimated HC5s was narrower for the food web modeling approach than for the SSD approach. The HC5-50s predicted by the two approaches were two to five times (metals) and 10 to 100 times (organic chemicals) higher than the predicted no effect concentrations (PNECs) for the aquatic environment listed in the risk assessment reports. This suggests that the derived PNECs are protective for aquatic ecosystems.

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Poly(p-xylylene) and Its Derivatives by Chemical Vapor Deposition: Synthesis, Mechanism, and Structure

Cited by 49 publications

References 11 publications

Poly(p-phenylene alkylene)s – A forgotten class of polymers

Poly(p-phenylene alkylene)s – A forgotten class of polymers

25th Anniversary Article: CVD Polymers: A New Paradigm for Surface Modifi cation and Device Fabrication

A re‐evaluation of fifteen years of european risk assessment using effect models

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