Paint & Coatings Industry - March 2008 - (Page 73)

Oligomers Modification without the concomitant increase in viscosity observed with linear polymers. Terminal hydroxyl groups on the poly(fluorooxetanes) can be transformed into a host of other functionalities using routine synthetic techniques. These modifications include carboxylic acids, amines and esters. The diversity of poly(fluorooxetane) terminal group chemistry is such that intermediates that are able to be used to produce polyurethanes, polyesters and polyamides, etc., can be readily designed. Additional modification steps can be used to produce reactive monomers such as acrylics. Examples are shown in Figure 3, where a poly(fluorooxetane) terminated on each end with hydroxyl groups, is coupled to a hydroxyacrylate using isophorone diisocyanate. The preparation of block copolymers using monomers such as acrylates is difficult and expensive, requiring rather exotic synthetic schemes. A marked advantage of cationic, ring-opening polymerization is the ability to prepare block copolymers as readily as random copolymers. Like dendrimers or hyperbranched monomers, poly(fluoroxetane) block copo- Figure 1 | Basic poly(oxetane) platform chemistry. CH3 HOCH2CCH2OH CH3 BF3 •THF H3 C O CH2OR f CH2OR f CH3 HO CH2CCH2O CH2CCH2 x CH3 CH3 CH2OR f OCH2CCH2 OH y CH3 6 ≤ x + y ≤ 20 R f = -CH2CF 3, -CH2CF 2CF3 H3C O CH2OR f R OH BF 3•THF CH2OR f R O CH2CCH2O H x CH3 6 ≤ x ≤ 20 R f = -CH2CF 3, -CH2CF 2CF3 Figure 2 | Initiation of fluorooxetane polymerization using polyhydric alcohols. CH2OR f CH2 OCH2CCH2 OH CH2 OH b CH3 HOCH2 CCH 2OH CH 2OR f CH2OR f CH 2OH HO CH 2CC H2O CH2CCH2 OCH2CCH2 OH a c BF3 •THF CH 3 CH3 CH3 CH2 OCH 2CCH2 OH R f = -CH2CF3, -CH2CF 2CF3 d CH2OR f 6 ≤ a + b + c + d ≤ 20 CH2OR f CH2 OCH 2CCH2 OH CH 2OH b CH3 HOCH 2CCH2 OH CH 2OR f CH2 OR f CH3 HO CH 2CCH2O CH2CCH2 OCH2CCH2 OH BF 3•THF a c CH 3 CH3 CH3 R f = -CH2CF 3, -CH2 CF 2CF3 6 ≤ a + b + c ≤ 20 H3C O CH2OR f Figure 3 | Poly(fluorooxetanes) with reactive, acrylic functional groups. C H3 H3 C O C H2 C HC O CH 2C H 2O C NH O R f = -C H 2 CF 3 , -C H 2 C F 2 C F 3 x + y ≈ 20 OR f C F 3 C H 2O H 3C CH 2C C H 2 O C NHC H 2 x CH 3 OR f O C H3 C H2 NHC O CH 2 C H3 C H 2C C H 2 O C H 2 C C H 2 x CH CH 3 3 OR f C H2 O C H 2 CC H2 C H3 H 3C OC NH C H 2 y O H3 C C H3 O NH CO C H 2C H 2O C C H O C H2 H 3C O C H3 O NHCO C H 2 C H 2 OC CH O R f = -C H 2 CF 3 , -C H 2 C F 2 C F3 x ≈ 10 CH 2 C H2 PA I N T & C O A T I N G S I N D U S T R Y 73

Table of Contents Feed for the Digital Edition of Paint & Coatings Industry - March 2008

Viewpoint Industry News Calendar of Events Company News Mergers and Acquisitions Names in the News Marketplace Quarterly Stock Watch Reaching Strict VOC Requirements With Outstanding Durability for Industrial Maintenance and Marine Coatings A Unique Fungicide for Wood-Filled Plastic deSigns of the Times: Slacking Off! From Rocks to Nanos Shear-Free Dispersion Process Fluorinated Oxetane Oligomers as Versatile Intermediates for Polymer Modification The Effects of TPO Composition on Adhesion and Proposed Chemical Mechanism Supplier Showcase Color Management Materials Watch Products Classifieds Advertiser Index

Paint & Coatings Industry - March 2008

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