Safe halomethylation of aromatic polymers via BCME-free long chain haloalkylethers

Warshawsky, Abraham; Deshe, A.; Gutman, Rodika

doi:10.1002/pi.4980160415

Cited by 66 publications

(12 citation statements)

References 9 publications

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“…Our experiences were negative in relation to the bromomethylation of PES; Warshawsky's bromomethylating agent, bromomethyl octyl ether, 6,9 failed when applied to this polymer. There was no reaction, even at reflux conditions.…”

Section: Introductionmentioning

confidence: 86%

Preparation and characterization of brominated polyethersulfones

Botvay

Máthé

Pöppl

et al. 1999

J. Appl. Polym. Sci.

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A novel derivative of aromatic polyethersulfone (PES) was obtained by bromination. Victrex PES was reacted with bromine under various conditions: in solution, in suspension, and without solvent; with or without catalyst; and at low and elevated temperatures. Practically no bromination occurred in solution; in the other cases, brominated PESs to various extents were obtained. The degree of substitution (DS) varied between 0.3 and 2.3. It was found that no catalyst is required for this reaction; the temperature, the concentrations of bromine and of polymer in the reaction mixture, and the duration of the reaction are the determinant factors of the DS. The modified polymers were characterized by elemental analysis, 1 H-NMR, 13 C-NMR, and PGC-MS, and their thermal properties were investigated by TGA and DSC methods. Further transformations of brominated PES as well as other new chemical reactions of PES will be the subject of later publications.

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Section: Introductionmentioning

confidence: 86%

Preparation and characterization of brominated polyethersulfones

Botvay

Máthé

Pöppl

et al. 1999

J. Appl. Polym. Sci.

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“…[chloromethyl-2-cyclohexylcyclohexylether: CCOM(CC)] This method was built on the paper [6]. 2-cyclohexylcyclohexanol was added to dehydrous chloroform and paraformaldehyde in flask.…”

Section: Protective Groupmentioning

confidence: 99%

Dry-etching resistance of fluoropolymers for 157-nm single-layer resists

Kawaguchi

Irisawa

Kodama

et al. 2003

Advances in Resist Technology and Processing XX

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Novel fluoropolymers having partially fluorinated monocyclic (5-membered and 6-membered ring) structure have been synthesized with radical cyclo-polymerization, which have C-F bond in the polymer main chain and also possess fluorocontaining acidic alcohol group. These polymers have excellent transparency lower than 1.0µm -1 at 157nm wavelength, a small amount of outgassing, high sensitivity and good adhesion to the wafer [1,2,3]. However, this fluoropolymer have lower etching resistance (half of conventional KrF resists) and it must be improved for applying to the single-layer resist. In this paper, we show the new model of the estimation of the dry-etching resistance for designing polymer compositions. It is well known that the model using carbon-atom-density as a parameter is useful for estimating dry-etching resistance [4,5]. However, these models did not agree with the results of our fluoropolymers. Our new model was focused on the surface area and the volume of the polymer. We succeeded to explain the relationship between the dry-etching resistance and the composition of the fluoropolymer. According to this model, the compositions of fluoropolymer such as protective groups, protective ratio and co-polymer units were optimized to improve their etching resistance.

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“…But chloromethyl methyl ether is a notorious carcinogen, so haloalkyl alkyl ethers having longchain alkyl groups have been investigated as safer reagents. 26,27 In this study, CMOE was used as a much less volatile reagent than the classical one. Table 1 shows some characteristics of the chloromethylated polysulphones (PSF-CM).…”

Section: Chemical Modification Of Polysulphonementioning

confidence: 99%

“…Chloromethyl octyl ether (CMOE) was prepared according to the method of Warshawsky et al 26,27 Typical procedures are brieÑy described.…”

Section: Preparation Of Chloromethyl Octyl Ethermentioning

confidence: 99%