Papers - Banno, Taisuke

[解説] 油中水滴エマルションを用いたジャイアントベシクル型人工細胞の器づくり

豊田 太郎*, 伴野 太祐, 藤浪 真紀

オレオサイエンス 12 ( 2 ) 77 - 84 2012

Lead author, Last author, Corresponding author, Accepted,  ISSN  2187-3461

• Access to Document (DOI)

Chemo-enzymatic Synthesis and Properties of Novel Optically Active Cationics Containing Carbonate Linkages

Taisuke Banno, Kazuo Kawada, Shuichi Matsumura

JOURNAL OF OLEO SCIENCE (JAPAN OIL CHEMISTS SOC)  60 ( 4 ) 185 - 195 2011.04

Lead author, Last author, Corresponding author, Accepted,  ISSN  1345-8957

　View Summary

Novel optically active carbonate-type cationics were designed and synthesized via a green method. A series of n-alkyl N,N-dimethylaminoalkyl carbonates was prepared via a two-step successive carbonate exchange reaction of diphenyl carbonate with 1-alkanol followed by the reaction of the optically active or racemic amino alcohol in the presence of triethylamine. The quaternarization of the N,N-dimethylamino group was carried out using methyl iodide. Furthermore, optically active cationics were prepared by the lipase-catalyzed enantioselective hydrolysis of the racemic cationics. Carbonate-type cationics having an isopropylene linkage showed high hydrolytic stability. They exhibited surfactant properties similar to those of the corresponding racemic cationics. Although no significant differences in the antimicrobial activities were observed owing to the stereochemistry of the cationics, the biodegradability was strongly influenced by the stereochemistry. Some optically active cationics were rapidly biodegraded by activated sludge.

• Access to Document (DOI)

Synthesis and Properties of Green Sustainable Carbonate-type Nonionics Containing Polyoxyethylene Chains

Taisuke Banno, Hiroshi Sato, Takayuki Tsuda, Shuichi Matsumura

JOURNAL OF OLEO SCIENCE (JAPAN OIL CHEMISTS SOC)  60 ( 3 ) 117 - 126 2011.03

Lead author, Last author, Corresponding author, Accepted,  ISSN  1345-8957

　View Summary

A series of polyoxyethylene surfactants containing carbonate linkages as biodegradable and chemically recyclable segments was designed and synthesized by a green process. A two-step carbonate exchange reaction was used: dimethyl or diphenyl carbonate was reacted with 1-alkanol, and the product was reacted with poly (ethylene) glycol in the presence of a lipase or chemical catalyst. The obtained carbonate-type nonionics exhibited good surface-active properties such as a low critical micelle concentration value and a surface tension lowering action. They were readily biodegraded by activated sludge, furthermore, could be chemical recycled using a lipase.

• Access to Document (DOI)

Creation of Novel Green and Sustainable Gemini-Type Cationics Containing Carbonate Linkages

Taisuke Banno, Kazuo Kawada, Shuichi Matsumura

JOURNAL OF SURFACTANTS AND DETERGENTS (SPRINGER HEIDELBERG)  13 ( 4 ) 387 - 398 2010.10

Lead author, Last author, Corresponding author, Accepted,  ISSN  1097-3958

　View Summary

Novel gemini-type cationics containing carbonate linkages as biodegradable and chemically recyclable segments were designed and synthesized by a green process. The carbonate linkages were introduced into only the hydrophobic moiety or in both the hydrophobic and linker moieties of gemini-type cationics. They showed higher surface activities, such as a low critical micelle concentration value, a surface tension lowering, and a high adsorption efficiency, when compared to the corresponding single-type cationics. Also, the gemini-type cationics containing carbonate linkages in both the hydrophobic and the linker moieties showed stronger antimicrobial activities when compared to those only in the hydrophobic moiety. It was found that some gemini-type cationics containing carbonate linkages showed higher biodegradability compared to the conventional gemini-type cationics. The biodegradability of the gemini-type cationics decreased when a carbonate linkage was introduced into the hydrophobic moiety rather than the linker moiety. However, some gemini-type cationics containing carbonate linkages both in the hydrophobic and linker moieties showed ready biodegradability. The gemini-type cationics containing carbonate linkages in the hydrophobic moiety showed chemical recyclability by a lipase (E.C. 3.1.1.3).

• Access to Document (DOI)

Synthesis and Properties of Polycarboxylate-type Green Surfactants with S- or N-Linkages

Yuu Okada, Taisuke Banno, Kazunobu Toshima, Shuichi Matsumura

JOURNAL OF OLEO SCIENCE (JAPAN OIL CHEMISTS SOC)  58 ( 10 ) 519 - 528 2009.10

Lead author, Last author, Corresponding author, Accepted,  ISSN  1345-8957

　View Summary

Polycarboxylate-type green surfactants with either sulfide- (S-) or imino- (N-) linkages were prepared in high yields by a single addition reaction of fatty mercaptan or fatty amine with unsaturated polycarboxylic acids such as fumaric, maleic, itaconic and aconitic acids. They exhibited surfactant properties and excellent biodegradabilities. Also, green surfactants with S-linkages showed better calcium ion sequestration abilities compared to the corresponding surfactant having an N-linkage. Among these surfactants, aconitic acid-derived polycarboxylate with an S-linkage exhibited calcium ion sequestration capacities similar to that of disodium 3-oxapentanedioate (ODA), a conventional calcium ion sequestrant on a molar basis of the surfactant.

• Access to Document (DOI)

Synthesis and Properties of Gemini-type Cationic Surfactants Containing Carbonate Linkages in the Linker Moiety Directed Toward Green and Sustainable Chemistry

Taisuke Banno, Kazunobu Toshima, Kazuo Kawada, Shuichi Matsumura

JOURNAL OF SURFACTANTS AND DETERGENTS (SPRINGER HEIDELBERG)  12 ( 3 ) 249 - 259 2009.08

Lead author, Last author, Corresponding author, Accepted,  ISSN  1097-3958

　View Summary

Gemini-type cationic surfactants containing carbonate linkages as biodegradable and chemically recyclable segments, consisting of two long-chain alkyl groups, two quaternary ammonium groups and a linker moiety, were designed and synthesized as novel green and sustainable cationics with improved physicochemical and biological activities. The gemini-type cationics containing a carbonate linkage showed lower critical micelle concentration values compared to the corresponding single-type cationics. Also, the gemini-type cationics containing a carbonate linkage in the linker moiety showed strong antimicrobial activities. The biodegradability of the gemini-type cationics was significantly improved when a carbonate linkage was introduced into the linker moiety. The maximum biochemical oxygen demand-biodegradability of the gemini-type cationics containing a carbonate linkage in the linker moiety exceeded 70% after a 28-day incubation. Furthermore, the gemini-type cationics containing both a carbonate linkage and an n-dodecyl group showed a chemical recyclability using a lipase (E.C. 3.1.1.3).

• Access to Document (DOI)

Synthesis and Properties of Biodegradable and Chemically Recyclable Cationic Surfactants Containing Carbonate Linkages

Banno Taisuke, Toshima Kazunobu, Kawada Kazuo, Matsumura Shuichi

Journal of Oil Chemists' Society, Japan (Japan Oil Chemists' Society)  56 ( 9 ) 493 - 499 2007

Lead author, Last author, Corresponding author, Accepted,  ISSN  1345-8957

　View Summary

Novel biodegradable and chemically recyclable carbonate-type cationic surfactants consisting of a long chain alkyl group and a quaternary ammonium propyl group were designed and synthesized as a green surfactant. These carbonate-type cationics showed better surface activities in an aqueous solution when compared to the conventional cationics. Novel cationics containing both the carbonate linkage and <i>n</i>-dodecyl group showed strong antimicrobial properties, enzymatic degradabilities for chemical recycling and rapid biodegradabilities by activated sludge.<br>

• Access to Document (DOI)