Synthesis of rodlike polysiloxane containing polyol moieties derived from glucose with regularly controlled higher-ordered structure

Kaneko, Yoshirō; Kadokawa, Jun‐ichi; Setoguchi, Mutsumi; Iyi, Nobuo

doi:10.1016/j.polymer.2005.06.042

Cited by 15 publications

(9 citation statements)

References 18 publications

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“…Furthermore, the methylene signals H a and H b of the product shift to higher field and the methylene signal H c shifts to lower field compared with those of 7. These shifts have also been observed in the synthesis of 3, 13 and are attributed to progress of the amidation reaction of 7 with 4. These spectroscopic results fully support the structure of the sugarand stearoyl-functionalized polysiloxane 8.…”

Section: Synthesis Of Amphiphilic Sugar-polysiloxane Hybridmentioning

confidence: 56%

“…As previously reported, 13 an introduction of 2 to 1 was performed by heating at 80 C in the presence of triethylamine in DMF to prepare a rigid polysiloxane 3 having polyol moieties (Scheme 1). The obtained product 3 was soluble in water and DMSO, but insoluble in typical organic solvents such as methanol, acetone, chloroform, and n-hexane.…”

Section: Reaction Of 1 Withmentioning

confidence: 99%

“…13 Because the sugar lactones like 2 react with the amino groups without protection of the hydroxy groups, they are useful substrates for such the simple procedure to exclude multi-reaction steps. However, 2 was not suitable for preparation of materials containing the sugar substituents, because the ring-opened moieties like the side chain of 3 formed from 2 had no any sugar-residues.…”

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confidence: 99%

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Synthesis of Sugar-Polysiloxane Hybrids Having Rigid Main-Chains and Formation of their Nano Aggregates

Beppu

Kaneko

Kadokawa

et al. 2007

Polym J

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ABSTRACT:We synthesized sugar-polysiloxane hybrids having rigid main-chains by reaction of sugar-lactones with amine-functionalized polysiloxane (1). Reaction of gluconolactone (2) with 1 was performed to obtain polysiloxane (3) having polyol moieties derived from glucose. This material has the regularly controlled higher-ordered structure in solid state such as the hexagonal phase. A hydrophilic sugar-polysiloxane hybrid (5) was prepared by reaction of lactobionolactone (4) with 1. Furthermore, an amphiphilic sugar-polysiloxane hybrid (8) was synthesized by introduction of stearoyl groups in addition to sugar groups on the surface of 1. The SEM image of the amphiphilic material 8 exhibited formation of nano aggregates having the particle diameters of ca. 50 nm in water.[doi:10.1295/polymj.PJ2006268] KEY WORDS Glycopolymer / Sugar-lactone / Polysiloxane / Amphiphilic / Hybrid / Nano Aggregate / There has been a growing interest in sugar portions of the glycoproteins because of exhibiting to bind to carbohydrate-recognition proteins, toxins, viruses, and cells. It has been known that a molecular assembly formed from the sugar-residues in the living system expresses stronger recognition ability than that of a single sugar molecule. This, so-called multivalent or cluster effect, has become a principle in the design of artificial glycoconjugate ligands. Therefore, polymeric materials having such functional sugar-residues, i.e., 'glycopolymer', have widely been investigated because these materials efficiently show the multivalent effect.

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Section: Synthesis Of Amphiphilic Sugar-polysiloxane Hybridmentioning

confidence: 56%

Section: Reaction Of 1 Withmentioning

confidence: 99%

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confidence: 99%

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Synthesis of Sugar-Polysiloxane Hybrids Having Rigid Main-Chains and Formation of their Nano Aggregates

Beppu

Kaneko

Kadokawa

et al. 2007

Polym J

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“…9 Its molecular weight (M n ) was evaluated to be 10,300 g/mol by GPC analysis with water as the eluent using pullulan standards. 12 The cross-linking agents (1a-c) were prepared using this water-soluble polysiloxane according to a literature procedure, 11 which were achieved by reaction of amino groups of the polysiloxane with acryloyl chloride. The functionalities of acrylamido groups determined by 1 H NMR spectra were 8% (1a), 17% (1b), and 21% (1c).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Temperature-Responsive Organic-Inorganic Hybrid Hydrogel by Free-Radical Polymerization of Methacrylamide Using Water-Soluble Rigid Polysiloxane Having Acryamido Side-Chains as a Cross-linking Agent

Kaneko

Noguchi

Kadokawa

2007

Polym J

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Polymeric hydrogels are three-dimensional polymer networks containing a large amount of water, which have been used in a variety of applications, e.g., soft contact lenses, absorbents, and cosmetics, due to their high water contents and soft touchness. 1 In particular, a considerable number of researches have been focused on stimuli-responsive hydrogels, in which they can change their properties in response to environmental stimuli such as pH, temperature, ionic strength, and electric field.2,3 The stimuli-responsive hydrogels have been investigated for many biomedical and pharmaceutical applications, e.g., drug delivery system (DDS). 2,3 As familiar examples, it has been reported that the hydrogels composed of poly(N-isopropylacrylamide), poly(N,N-diethylacrylamide), and poly-(ethylene oxide)-poly(propylene oxide) block copolymer have exhibited temperature-response. 2-6On the other hand, the hydrogels had some serious disadvantages such as brittleness and lack of mechanical toughness. So far, to solve these disadvantages of the hydrogels, synthesis of organic-inorganic nanocomposite (hybrid) hydrogels have been reported, 7,8 which are composed of organic polymer as a mainchain and inorganic dispersed clay as a cross-linking agent. A clay has two-dimensional rigid sheet structure forming regular higher-ordered structure (lamellar phase) and can disperse in the water. These properties of the clay would contribute to the superior characteristics such as high mechanical strength, elongation, and transparency of the hydrogels. However, since other inorganic materials, which have rigid structure and dispersion behavior, have hardly ever been known, the variety of the organic-inorganic hybrid hydrogels has been restricted. The availability of new inorganic cross-linking agents promisingly introduces additional development of new functions and applications of novel high-performance hybrid hydrogels.So far, water-soluble polysiloxanes having alkylammonium groups were synthesized by the sol-gel reaction of aminoalkyltrialkoxysilane in strong acid aqueous solution.9,10 In the solid state, these polysiloxanes were stacked to form the hexagonal phase, implying their rigid-rod structures. The polysiloxanes have inspired us to use them for the development of a new hybrid hydrogel, because of their comparable water-dispersibility and rigidity to those of a clay. Accordingly, we prepared a polysiloxane-based multifunctional cross-linking agent for a new organic-inorganic hybrid hydrogel.11 The cross-linking agent was synthesized by reaction of the rigid polysiloxane with acryloyl chloride. Then, the organic-inorgnic hybrid hydrogels were obtained by free-radical polymerization of an acrylamide (AAm) monomer using the cross-linking agent. The compressive properties of the obtained hydrogels were more superior than those of conventional poly(AAm) (PAAm) hydrogels. Based on the backgrounds described above, development of novel temperature-responsive organic-inorganic hybrid hydrogels would be a promising topic in the material rese...

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“…[13][14][15][16][17] But it involves the time and material consuming steps of protecting and deprotecting the hydroxyl groups of the carbohydrate in order to avoid side reactions in these processes. To overcome the problem, another simpler method has been developed by our group and others [18][19][20][21][22][23] : glycopolysiloxane can be synthesized by forming amide bonds of amino functional polysiloxane with lactones (or acids).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Surface and Spreading Properties of Lactobionamide-Grafted Amphiphilic Glycopolysiloxanes

Zhang

Wang

et al. 2013

Journal of Dispersion Science and Technology

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Three lactobionamide-grafted amphiphilic glycopolysiloxanes (LBPS) were synthesized using a two-step method. First, the aminopropyl functional polysiloxanes (APSO) were synthesized by equilibrium polymerization; then, lactobionic acid was conjugated to the APSO to give the glycopolysiloxanes LBPS. The final compositions of the amphiphilic glycopolysiloxanes were characterized by FTIR and 1 H NMR. Surface activities and spreading behaviors in aqueous solution of these three glycopolysiloxanes were investigated by surface tension measurements and contact angle measurements. The results show that these three glycopolysiloxanes have much higher surface activity than those of conventional carbon-carbon chain glycopolymers in aqueous solution and the spreading ability of three lactobionamide-grafted amphiphilic glycopolysiloxanes solution on low-energy surfaces is not only solely dependent on surface tension, but also dependent on hydrophilic-lipophilic balance of surfactant.

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Synthesis of rodlike polysiloxane containing polyol moieties derived from glucose with regularly controlled higher-ordered structure

Cited by 15 publications

References 18 publications

Synthesis of Sugar-Polysiloxane Hybrids Having Rigid Main-Chains and Formation of their Nano Aggregates

Synthesis of Sugar-Polysiloxane Hybrids Having Rigid Main-Chains and Formation of their Nano Aggregates

Synthesis of Temperature-Responsive Organic-Inorganic Hybrid Hydrogel by Free-Radical Polymerization of Methacrylamide Using Water-Soluble Rigid Polysiloxane Having Acryamido Side-Chains as a Cross-linking Agent

Synthesis, Surface and Spreading Properties of Lactobionamide-Grafted Amphiphilic Glycopolysiloxanes

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