Novel fluorinated polymers by radical polyaddition of bis(α-trifluoromethyl-β-difluorovinyl) dicarboxylate with ether

Narita, Tadashi; Hagiwara, Tokio; Hamana, Hiroshi

doi:10.1002/(sici)1521-3935(20000201)201:2<220::aid-macp220>3.0.co;2-9

Cited by 17 publications

(24 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The radical polyaddition reaction has also produced polymers from bis(a-trifluoromethyl-b,b-difluorovinyl)dicarboxylates with diethyl ether and 1,2-dimethoxyethane. [3] This paper deals with the radiation-induced polyaddition of BFP with DOX. It is well-known that irradiation with g-rays from a 60 Co source induces a wide variety of ionic and radical reactions and, thus, produces compounds which are hardly yielded under usual reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Novel Fluorinated Polymer by Radiation‐Induced Polyaddition of Bisperfluoroisopropenyl Terephthalate with 1,4‐Dioxane

Enomoto

Narita

Maekawa

et al. 2003

Macro Chemistry & Physics

Self Cite

View full text Add to dashboard Cite

Radical polyaddition of bis(α‐trifluoromethyl‐β,β‐difluorovinyl) terephthalate [CF2C(CF3)OCOC6H4COOC(CF3)CF2] (BFP) with 1,4‐dioxane (DOX) was investigated under γ‐rays radiation from a 60Co source to produce higher molecular weight polymers compared to those yielded by benzoyl peroxide initiation. Prior to polyaddition, the addition reactions of 2‐benzoxypentafluoropropene [CF2C(CF3)OCOC6H5] (BPFP) with tetrahydrofuran (THF) and DOX, and BFP with THF were examined in order to develop probable polyaddition reaction conditions. The polymer bearing 1.5 × 104 as a molecular weight was obtained under the feed molar ratio of DOX/BFP = 16 with an irradiation dose of 2 000 kGy at 40 °C, which is a much higher molecular weight compared to that yielded by benzoyl peroxide. magnified image

show abstract

Section: Introductionmentioning

confidence: 99%

Novel Fluorinated Polymer by Radiation‐Induced Polyaddition of Bisperfluoroisopropenyl Terephthalate with 1,4‐Dioxane

Enomoto

Narita

Maekawa

et al. 2003

Macro Chemistry & Physics

Self Cite

View full text Add to dashboard Cite

show abstract

“…33 The results are shown in Table 4 which indicates that diethyl ether also works as a bifunctional compound in this polyaddition reaction because the polymer is produced as high as 68% yield at 80°C in the presence of BPO. The polymer is a pale yellow solid, and soluble in common organic solvents such as benzene, THF, and chloroform and insoluble in hexane.…”

Section: Polyaddition Of Bfp With Ethersmentioning

confidence: 92%

“…Besides BFP, many dicarboxylic acid derivatives such as bis(␣-trifluoromethyl-␤,␤-difluorovinyl) adipate, glutarate, and cyclohexanedicarboxylate are candidates for polymer production, 33 which may be applicable to preparation of polymers bearing appropriate functional groups in main chains by the introduction of the groups into dicarboxylate segments. The attempt at the reactions of other chlorinated compounds with lithium enolate of HFIP to afford novel perfluoroisopropenyl compounds would also be desirable to prepare facile introduction of functional groups.…”

Section: Ongoingmentioning

confidence: 99%

Novel fluorinated polymers by radical polyaddition: Inspiration and progress

Narita¹

2004

J. Polym. Sci. A Polym. Chem.

Self Cite

View full text Add to dashboard Cite

The story of the outset and the growth of radical polyaddition of bisperfluoroisopropenyl derivatives [CF2C(CF3)R C(CF3) CF2] with several organic compounds possessing carbon–hydrogen bonds is described. The reaction afforded novel fluorinated polymers bearing such organic segments in polymer main chains as 1,4‐dioxane, diethyl ether, dimethoxyethane, 18‐crown‐6, triethylamine, glutaraldehyde, and alkanes which have never been supposed as direct starting compounds for preparation of polymers. The facile method for preparation of fluorinated hybrid polymers bearing alkylsilyl groups was developed with diethoxydimethylsilane and silsesquioxanes. Taking advantage of the high reactivity of the perfluoroisopropenyl group as a radical acceptor, self‐polyaddition and cyclopolymerization were investigated. Triethysilyl perfluoroisopropenyl ether [CF2 C(CF3)OSi(C2H5)3] was proved to be the most probable candidate for self‐polyaddition. Cyclopolymerization of perfluoroisopropenyl vinylacetate [CF2C(CF3) OCO CH2CH CH2] was investigated to afford polymers possessing five‐membered‐ring units in main chains. The interconversion of the unstable fluorinated carbon radical and the stable hydrocarbon radical had an important role in the reaction. The radical addition reaction presented herein may be developed for preparation of a wide variety of novel fluorinated polymers and organic compounds possessing functional groups. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 4101–4125, 2004

show abstract

“…The development of radical addition reaction of perfluoroisopropenyl group (CF 2 ¼CðCF 3 ÞÀ) with the organic compounds possessing carbonÀhydrogen bonds enables to prepare a wide variety of fluorinated polymers from the compounds which have never been supposed as starting materials for preparation of polymers. The reaction has been developed to preparation of polymers with 1,2-dimethoxyethane [3], diformylalkane [4], triethylamine [5] and dialkoxydialkylsilanes [6].…”

Section: Introductionmentioning

confidence: 94%

Radical polyaddition reaction of bis(α-trifluoromethyl-β,β-difluorovinyl) 2,3,5,6-tetrafluoroterephthalate

Fujiwara¹,

Narita²,

Hamana³

et al. 2004

Journal of Fluorine Chemistry

Self Cite

View full text Add to dashboard Cite

Novel fluorinated polymers by radical polyaddition of bis(α-trifluoromethyl-β-difluorovinyl) dicarboxylate with ether

Abstract: What's the real point of college?

Cited by 17 publications

References 4 publications

Novel Fluorinated Polymer by Radiation‐Induced Polyaddition of Bisperfluoroisopropenyl Terephthalate with 1,4‐Dioxane

Novel Fluorinated Polymer by Radiation‐Induced Polyaddition of Bisperfluoroisopropenyl Terephthalate with 1,4‐Dioxane

Novel fluorinated polymers by radical polyaddition: Inspiration and progress

Radical polyaddition reaction of bis(α-trifluoromethyl-β,β-difluorovinyl) 2,3,5,6-tetrafluoroterephthalate

Contact Info

Product

Resources

About