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Doctoral Thesis
DOI
https://doi.org/10.11606/T.46.2002.tde-06102003-163601
Document
Author
Full name
Paulo Augusto Rodrigues Pires
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2002
Supervisor
Committee
Seoud, Omar Abdel Moneim Abou El (President)
Baptista, Mauricio da Silva
Areas, Elizabeth Pinheiro Gomes
Frollini, Elisabete
Gehlen, Marcelo Henrique
Title in Portuguese
Síntese e propriedades de soluções de tensoativos catiônicos derivados de (3-dimetilaminopropil)amidas de ácidos carboxílicos
Keywords in Portuguese
3-dimetilaminopropilamidas
amido-aminas
detergentes
micelas
síntese orgânica
tensoativos catiônicos
Abstract in Portuguese
Duas séries homólogas de tensoativos foram sintetizadas, os cloretos de benzil-(3-acilaminopropil)dimetilamônio, RCONH(CH'ind.2')3N'pot.+'(CH'ind.3')]pot.2'CH'pot.2'C'pot.6'H'pot.5'Cl'pot.-'e (3-acilaminopropil)trimetilamônio, RCONH[(CH'pot.2')]'ind.3'N'pot.+'(CH'ind.3')'pot.3'Cl'ind. -' , onde RCO = C'ind.10' a C'ind.16'. A síntese foi realizada a partir de precursor comum, RCONH(CH'ind.2')'pot.3'N'(CH'ind.3')ind.2', sendo a quaternização feita pela reação com cloreto de benzila e iodeto de metila (seguido de troca iônica), respectivamente. Investigou-se a adsorção na interface solução/ar, a micelização e a estrutura dos agregados formados. Os resultados foram comparados com os de tensoativos catiônicos. Algumas das propriedades micelares das séries estudadas (ex: concentrações micelares críticas, graus de dissociação, números de agregação) tem valores na mesma faixa de grandeza dos outros tensoativos catiônicos com o mesmo tamanho de cadeia hidrofóbica. Outras, por exemplo, a energias livres de Gibbs de adsorção e micelização são diferentes (mais favoráveis). Os resultados apontam para o fato de que o grupo 3-amidopropila, [-CO-NH-CH'ind.2'-CH'ind.2'-CH'ind.2'-], quando inserido na molécula do tensoativo, acaba constituindo parte do seu grupo hidrofílico e facilita a micelização do mesmo. A polaridade microscópica da água interfacial foi determinada usando sondas solvatocrômicas e mostra que a água interfacial é menos polar que água 'bulk'.
Title in English
Synthesis and solution properties of cationic surfactants derivated from fat acids of (3-dimethylaminopropyl)amides.
Keywords in English
3-dimethylaminopropylamides
amido-amines
cationic
micelles
organic
physical-chemistry
properties
surfactants
synthesis
Abstract in English
The following surfactants have been synthesized: benzyl-(3-acyl-aminopropyl)dimethylammonium chloride, RCONH(CH'ind.2')'ind.3'N'pot.+'(CH'ind.3')'ind.2'CH'ind.2'C'ind.6'H'ind.5' Cl'pot.-' and (3-acylaminopropyl) trimethylammonium chloride, RCONH(CH'ind.2')'ind.3'N'pot.+'(CH'ind.3')'ind.3' Cl'ind.-', where RCO = C'ind.10' to C'ind.16'. The two series have been synthesized from the precursor RCONH(CH2)3N(CH3)2, by quaternization with benzyl chloride, and/or methyl iodide (followed by ion exchange), respectively. Adsorption at solution/air interface and micellization in aqueous solution has been studied, and the results compared with those of other cationic surfactants. Some properties, e.g., critical micelle concentrations, degrees of micelle dissociation, and aggregation numbers are similar to those of other cationic surfactants of equivalent hydrophobic chain length. The Gibbs free energies of adsorption at solution/air interface, and of micellization are, however, more favorable. The group [-CO-NH-CH'ind.2'-CH'ind.2'-CH'ind.2'-] is a part of the interface, and lead to favorable micellization. The microscopic polarity of interfacial water has been measured by appropriate solvatochromic probes, and is less than that of bulk water.
 
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Paulo_A_R_Pires.pdf (1.55 Mbytes)
Publishing Date
2003-11-24
 
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