Post-functionalization of novolac resins by introducing thermo-crosslinkable –OCFCF<sub>2</sub> groups as the side chains: a new strategy for production of thermosetting polymers without releasing volatiles

Zhou, Junfeng; Fang, Liang; Wang, Jiajia; Sun, Jing; Jin, Kaikai; Fang, Qiang

doi:10.1039/c6py00788k

Cited by 19 publications

(12 citation statements)

References 22 publications

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“…The TFVE-functionalized polymer can be easily converted to a cross-linked network having perfluorocyclobutyl ether (PFCB) units. Usually, PFCB groups may endow the polymers with high thermostability, transparency, and good dielectric properties. − In our case, eugenol was selected as a feedstock to synthesize the new norbornene monomer because of its bifunctional nature, of which the allyl group can construct a norbornene unit, and hydroxyl group is a suitable block for the connection of TFVE unit. Moreover, dicyclopentadiene is a low-cost compound and is often considered as a byproduct from petrochemical industry (C5 fraction) .…”

Section: Introductionmentioning

confidence: 99%

Low Dielectric Fluorinated Polynorbornene with Good Thermostability and Transparency Derived from a Biobased Allylphenol (Eugenol)

Fang¹,

Zhou²,

Tao³

et al. 2019

ACS Sustainable Chem. Eng.

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A new biobased functional norbornene was synthesized by the Diels–Alder reaction between cyclopentadiene and the fluorinated eugenol. Based on the norbornene monomer, a new polynorbornene was prepared with a high molecular weight (M n = 78 000 Da) by the standard ring opening metathesis polymerization (ROMP). This polymer displayed good film-forming ability and can be postpolymerized to form a cross-linked network at high temperature (>150 °C) via the [2 + 2] cycloaddition reaction of trifluorovinyl ether (−OCF2CF2) groups. The cross-linked polymer exhibited good transmittance (T % > 90% at 550 nm) and high thermostability with a 5% weight loss temperature of 412 °C. Moreover, no obvious glass transition temperature (T g) was observed in the DMA measurement when the temperature was elevated near the decomposition temperature of the cross-linked polymer (about 350 °C). The cured resin displayed an average dielectric constant (D k) of below 2.65 with average dissipation factor (D f) of 4.3 × 10–3 for the frequencies varying from 40 Hz to 25 MHz. The cross-linked polymer film also possessed good hydrophobicity with a contact angle of 104° (water on the surface of the film) and a surface energy of 26.8 mJ m–2. These data indicate that the combination of norbornene and the fluorinated eugenol can greatly improve properties of polynorbornene, which could have potential application in microelectronic industry. Thus, this contribution may provide a new way for the usage of the biomass.

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Section: Introductionmentioning

confidence: 99%

Low Dielectric Fluorinated Polynorbornene with Good Thermostability and Transparency Derived from a Biobased Allylphenol (Eugenol)

Fang¹,

Zhou²,

Tao³

et al. 2019

ACS Sustainable Chem. Eng.

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“…In recent years, we are interested in developing the new materials with both high performance and good process-bility. 12,[23][24][25][26] It was found in our previous investigations that polymers or monomers with triuorovinyl ether (TFVE) groups were more suitable for the preparation of the materials having both satisfactory physical properties and good processability. Those polymers or monomers usually showed good solubility in common organic solvents, as well as low melting point.…”

Section: Introductionmentioning

confidence: 99%

A spiro-centered thermopolymerizable fluorinated macromonomer: synthesis and conversion to the high performance polymer

et al. 2017

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A new spiro-centered thermopolymerizable fluorinated macromonomer is reported here. This fourfunctional macromonomer is synthesized by a convergent strategy, and shows a low melting point (93 C) and good solubility in the common organic solvents. When heated to a high temperature, the macromonomer converts into a cross-linked network (PD 1 ), which exhibits a T g of near 316 C and a 5% weigh loss at a temperature of 417 C in N 2 . PD 1 also shows a low dielectric constant (D k ¼ 2.58 at 30 MHz) and high hydrophobicity (a water contact angle of q ¼ 98 ), as well as low water uptake (about 0.45%, kept in boiling water for 72 h). These results suggest that the macromonomer has a potential application in the production of the high performance polymers, in particular, it is very suitable for encapsulation resins or the coatings utilized in the microelectronics industry.Scheme 1 Procedure for the synthesis and conversion of the new monomer D 1 .

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“…Up to now, TFVE groups have been widely used in various materials to improve their thermal stabilities. Zhou et al [ 20 ] introduced TFVE group into phenolic resin and improved its thermal stability through post-crosslinking. In addition, TFVE groups have also been introduced into other polymers, such as poly(arylene ether) [ 21 ], poly(fluorene-co-sulfone)ether [ 22 ], phenylphosphine oxide materials [ 23 ] and so on.…”

Section: Introductionmentioning

confidence: 99%

Study on the Synthesis and Thermal Stability of Silicone Resin Containing Trifluorovinyl Ether Groups

Huang

Yao

et al. 2020

Polymers

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Silicone resin is a high-temperature resistant material with excellent performance. The improvement of its thermal stability has always been the pursuit of researchers. In this paper, a sequence of silicone resins containing trifluorovinyl ether groups were prepared by the co-hydrolysis-polycondensation of methyl alkoxysilane monomers and {4-[trifluorovinyl(oxygen)]phenyl}methyldiethoxysilane. The structures of the silicone resins were characterized by FT-IR and 1H NMR. The curing process of them was studied by DSC and FT-IR spectra, and results showed that the curing of the resins included the condensation of the Si-OH groups and the [2 + 2] cyclodimerization reaction of the TFVE groups, which converted to perfluorocyclobutane structure after curing. The thermal stability and thermal degradation behavior of them was studied by TGA and FT-IR spectra. Compared with the pure methyl silicone resin, silicone resins containing TFVE groups showed better thermal stability under both N2 and air atmosphere. Their hydrophobic properties were characterized by contact angle test. Results showed that PFCB structure also improved the hydrophobicity of the silicone resin.

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Post-functionalization of novolac resins by introducing thermo-crosslinkable –OCFCF₂ groups as the side chains: a new strategy for production of thermosetting polymers without releasing volatiles

Cited by 19 publications

References 22 publications

Low Dielectric Fluorinated Polynorbornene with Good Thermostability and Transparency Derived from a Biobased Allylphenol (Eugenol)

Low Dielectric Fluorinated Polynorbornene with Good Thermostability and Transparency Derived from a Biobased Allylphenol (Eugenol)

A spiro-centered thermopolymerizable fluorinated macromonomer: synthesis and conversion to the high performance polymer

Study on the Synthesis and Thermal Stability of Silicone Resin Containing Trifluorovinyl Ether Groups

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Post-functionalization of novolac resins by introducing thermo-crosslinkable –OCFCF2 groups as the side chains: a new strategy for production of thermosetting polymers without releasing volatiles

Cited by 19 publications

References 22 publications

Low Dielectric Fluorinated Polynorbornene with Good Thermostability and Transparency Derived from a Biobased Allylphenol (Eugenol)

Low Dielectric Fluorinated Polynorbornene with Good Thermostability and Transparency Derived from a Biobased Allylphenol (Eugenol)

A spiro-centered thermopolymerizable fluorinated macromonomer: synthesis and conversion to the high performance polymer

Study on the Synthesis and Thermal Stability of Silicone Resin Containing Trifluorovinyl Ether Groups

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Product

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Post-functionalization of novolac resins by introducing thermo-crosslinkable –OCFCF₂ groups as the side chains: a new strategy for production of thermosetting polymers without releasing volatiles