Synthesis and Surfactant Properties of Novel Amphiphilic Fluorinated Silicon Oligomers Containing Carboxy Groups

Sawada, Hideo; Itoh, Nahoko; Kawase, Tokuzō; Mitani, Makoto; Nakajima, Hiromitsu; Nishida, Masami; Moriya, Yasuo

doi:10.1021/la00016a005

Cited by 38 publications

(15 citation statements)

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“…Related compounds containing no ether linkage showed only small surface activity. Sawada et al [73] have synthesized a range of fluorinated silicon oligomers containing carboxy groups. These materials were found to be easily soluble in both water and a range of organic solvents.…”

Section: Fluorosurfactants Containing a Hydrophilic Groupmentioning

confidence: 99%

Fluorinated and semi-fluorinated surfactants

Fletcher¹

1997

Specialist Surfactants

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Surfactants which contain one or more fluorinated or partially fluorinated hydrophobic groups (fluorinated surfactants or 'fluorosurfactants') can show dramatically different properties to those of hydrocarbon surfactants. The special properties of fluorosurfactants, which result from the unique properties of fluorocarbon chains, makes them irreplaceable in a wide range of applications and justifies Kissa's claim in his 1994 text on the subject that fluorinated surfactants are truly 'super surfactants' [1]. Rather than exhaustively review the huge literature on fluorosurfactants, the main aim of this chapter is to give an account of the special surfactant properties of fluorinated surfactants and to relate these properties to the differences in physical properties between fluorocarbon and hydrocarbon chains.The chapter is organized as follows. The main structural types of common fluorosurfactants and some aspects of their synthesis are described briefly in sections 5.2 and 5.3. In section 5.4, the physical properties of fluorinated and partially fluorinated chains are discussed and compared with those of the corresponding hydrocarbons. As will be seen, the different properties of the two types of chain provide a good basis for the rationalization and interpretation of the special properties of fluorosurfactants. Adsorption and aggregation behavior of fluorosurfactants in water is discussed in section 5.5. Adsorption and aggregation in apolar oil solutions of fluorosurfactants is covered in section 5.6. Section 5.7 gives a description of their phase behavior in mixtures of oil and water. The wetting of solid surfaces by fluorosurfactant solutions is dealt with in section 5.8. Finally, section 5.9 gives a brief summary of the main applications of fluorosurfactants. Structures of fluorinated surfactantsLike conventional surfactants, fluorosurfactants generally contain a hydrophilic group and a hydrophobic group within the same molecule. A selection of the wide range of fluorosurfactant molecular structures are described here. A more exhaustive list is given in chapter 1 of Reference 1.The hydrophobic group of fluorinated or semifluorinated surfactants can I. D. Robb (ed.), Specialist Surfactants

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Section: Fluorosurfactants Containing a Hydrophilic Groupmentioning

confidence: 99%

Fluorinated and semi-fluorinated surfactants

Fletcher¹

1997

Specialist Surfactants

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“…Fluorinated surfactants also show surface activity in organic solvents (2)(3)(4). Mainly anionic (5), cationic (6), and nonionic (7,8) fluorinated surfactants have been synthesized but little has been reported concerning zwitterionic or amphoteric fluorinated surfactants.…”

Section: Introductionmentioning

confidence: 99%

Surface-Tension Properties of Novel Phosphocholine-Based Fluorinated Surfactants

Rodríguez

Kunieda

Noguchi

et al. 2001

Journal of Colloid and Interface Science

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“…17 These fluoroalkyl end-capped cooligomers form molecular aggregates resembling normal and reverse micelles in water and organic solvents, respectively.…”

Section: Aggregation Of Fluoroalkyl End-capped Oligomers-formation Ofmentioning

confidence: 99%

Development of Fluorinated Polymeric Functional Materials Using Fluorinated Organic Peroxide as Key Material

Sawada

2007

Polym J

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ABSTRACT:Fluoroalkanoyl peroxide [R F -C(=O)OO(O=)C-R F ] decomposes homolytically through concerted three bond radical fission to afford fluoroalkyl radical (R F . ) selectively, although the corresponding alkanoyl peroxide ]. This decomposition of fluoroalkanoyl peroxide was applied to the direct fluoroalkylation of two end-sites of vinylsilane oligomers and (meth)acrylate oligomers. Fluoroalkyl end-capped trimethoxyvinylsilane oligomers [R F -(CH 2 CHSi(OMe) 3 ) n -R F ] thus obtained were applied to the surface modification on glass and traditional organic polymers such as PMMA and rubbers to exhibit not only strong hydrohobicity but good oleophobicity imparted by fluorine with extremely higher adhesive property on their surface. Fluoroalkyl end-capped actylate and methacrylate oligomers exhibited surface active properties imparted by fluorine, the same as for low-molecular weight fluorinated surfactants, and these fluorinated cooligomers formed the nanometer size-controlled self-assembled molecular aggregates in aqueous and organic media. These fluorinated molecular aggregates interacted with a variety of guest molecules such as low molecular biocides, fullerenes, and carbon nanotubes to afford the corresponding fluorinated oligomers/guest molecules nanocomposites. These fluorinated oligomers were applied to the preparation of fluorinated oligomers/silica gel nanocomposites and cross-linked fluorinated oligomeric nanoparticles.[doi:10.1295/polymj.PJ2006242] KEY WORDS Fluoroalkanoyl Peroxide / End-capped Fluoroalkyl Group / Carbon-carbon Bond Formation / Oligomer / Aggregation of Fluorine / Self-assembly / Oleophobicity / Surface Modification / Nanoparticle / Randomly fluoroalkylated macromolecules such as acrylated, methacrylated and acrylamide polymers containing longer perfluoroalkyl groups exhibit interesting characteristics imparted by fluorine that set them apart from the usual alkylated macromolecules. 1 Such randomly perfluoroalkylated polymers have in general relatively lower solubility in most solvents and are poor surfactants.2 Therefore, the exploration of surface active fluoroalkylated polymers leading to relatively high solubility in both water and common organic solvents including non-polar solvents should open a new route to the development of new functional materials, particularly new amphiphilic fluorinated polymeric materials. A considerable interest has been devoted in recent years to block copolymers containing fluoroalkyl groups owing to exhibiting the low surface energy and the self-assembled polymeric aggregates resembling micelle in aqueous and organic media, which cannot be achieved in the corresponding randomly fluoroalkylated copolymers.3 These longer perfluoroalkylated block copolymers have high potential for application to new fluorinated polysoaps. New fluorinated block copolymers have been recently prepared through RAFT (Reversible-Addition-Fragmentation-Transfer) and Atom Transfer Radical Polymerization (ATRP) techniques. 4 However, in the longer fluoroalkylated polysoaps,...

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Synthesis and Surfactant Properties of Novel Amphiphilic Fluorinated Silicon Oligomers Containing Carboxy Groups

Cited by 38 publications

References 0 publications

Fluorinated and semi-fluorinated surfactants

Fluorinated and semi-fluorinated surfactants

Surface-Tension Properties of Novel Phosphocholine-Based Fluorinated Surfactants

Development of Fluorinated Polymeric Functional Materials Using Fluorinated Organic Peroxide as Key Material

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