Synthesis and performance of ester quaternary biodegradable softeners

Lagerman, R.; Clancy, S.; Tanner, D. W.; Johnston, Norman J.; Callian, B.; Friedli, F. E.

doi:10.1007/bf02541479

Cited by 17 publications

(10 citation statements)

References 3 publications

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“…Distortionless enhanced polarization transfer (DEPT), correlation spectroscopy (COSY), and heteronuclear multiple quantum coherence (HHQC) experiments were used to make structural assignments. δ-Eicosanolactone and γ-eicosanolactone spectra were identical to those previously reported (10), and the amides are consistent with NMR data reported from the ring opening of γ-stearolactone (13,16). 1 Methods.…”

Section: Methodssupporting

confidence: 88%

“…δ-Valerolactone reacted 22 times faster than γ-butyrolactone in the presence of alkali, and 170 times faster in acidic solutions. In a more recent study, γ-butyrolactone underwent ring opening to amides (13) with primary and secondary amines at 100°C, with the reaction reaching completion in 5 h. γ-Caprolactone was also reacted in this study (13) but exhibited a slower rate of reaction, possibly owing to the incorporation of the small alkyl side-chain.…”

mentioning

confidence: 54%

“…3 ) 13. C NMR: δ 172.0 (s, C=O), 80.6 (d, -O-CH-), 35.8 (t, CH 2 CO), 31.9 (t, CH 2 CH 2 CH-O), 29.14.1 ppm (q, CH 3 ) 1.…”

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confidence: 99%

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The rate of ring opening of γ‐and δ‐lactones derived from meadowfoam fatty acids

Isbell

Steiner

1998

J Americ Oil Chem Soc

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δ-Lactones derived from meadowfoam (Limnanthes) fatty acids were reacted with amine and alcohol nucleophiles in a second-order reaction to provide the acyclic 5-hydroxy eicosanoic acid esters and amides. The rate of reaction for the ring opening of δ-lactones was compared to the rate of ring opening of γ-lactones and the rate of derivatization of meadowfoam fatty acids. δ-Lactones showed a much larger rate for the formation of derivatives than the corresponding γ-lactones or fatty acids. δ-Lactone had a rate constant >7700 times larger for the formation of butyl ester than meadowfoam fatty acids. The formation of amides from δ-lactones is even faster than the esterification reaction and requires no catalyst or solvent when conducted at the melting point of the lactone. JAOCS 75, 63-66 (1998).

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Section: Methodssupporting

confidence: 88%

mentioning

confidence: 54%

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The rate of ring opening of γ‐and δ‐lactones derived from meadowfoam fatty acids

Isbell

Steiner

1998

J Americ Oil Chem Soc

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“…This is largely valid also for the subgroup of cationic surfaceactive agents, as has been demonstrated by a number of very recent publications. These studies describe products with cleavable links such as cyclic acetal (3), acyclic acetal (4), cyclic ketal (3,5), disulfide (6), silicon-carbon (7), transition metal complex (8), hydrazinium (9), amide (10), ester (10), or even a combination of amide and ester (11,12). Regarding the so-called "esterquats," a well-known class of degradable cationic surfactants, most of the progress has been published in the patent literature.…”

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confidence: 97%

Ortho ester‐based cleavable cationic surfactants

Hellberg

2002

J Surfact & Detergents

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A new type of cleavable cationic surfactant, based on the ortho ester link, is described. Ortho ester amines with alkyl chain lengths from C 8 to C 16 were synthesized from a short-chain ortho ester, a fatty alcohol, and an amino alcohol. The ortho ester amine was subsequently quaternized with methyl chloride, yielding a cationic surfactant. The structures were confirmed by 1 H and 13 C nuclear magnetic resonance and the surface chemical properties were investigated by measuring both static and dynamic surface tensions. The results were compared to standard n-alkyl trimethyl ammonium bromides. The critical micelle concentrations were found to vary rather widely, whereas the surface tensions in some cases were comparatively low. The short alkyl chain ortho ester quaternaries were found to have low surface tensions at short surface ages and to induce rapid wetting of a hydrophobic surface in dynamic tests. Additionally, the new surfactants were found to hydrolyze rapidly under mild acidic conditions, as measured by both titation and monitoring of the dynamic surface tension. Further, they showed excellent long-term stability at pH 10 in dilute aqueous solutions. The effect of added electrolyte on rate of hydrolysis was also investigated. A marked enhancement in the hydrolysis rate was found when NaBr was added, whereas NaCl did not have the same effect. The new surfactants could potentially be used to provide temporary surfactant action in application areas such as disinfection, fabric care, personal care, chain lubrication, and mineral flotation as well as in textile processes such as dyeing or scouring. a As shown in Scheme 1, x refers to the ethyl substituent, y to the fatty alcohol substituent, and z to the short-chain amine substituent. See text for details. Abbreviation: NMR, nuclear magnetic resonance.FIG. 6. Hydrolysis characteristics for an n-C 10 -trimethylamino ortho ester quat. Bulk surface activity was measured by the bubble pressure method. Temperature was 21 or 50ºC. Surface ages were 3-18 s. Initial concentrations were ca. 1 g/L of solvent-containing product.

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“…b-Presence of active hydrogen atoms (NH, NH 2 , SH, OH and COOH) in the molecule which are able to propyloxylate Lagerman, et al, 1994) to produce the hydrophobic part in a correct hydrophilichydrophobic balance (Pegiadou, et al, 2000) It has recently been reported that surfactants containing heterocyclic moiety have bactericidal and antifungal activities as well as industrial importance Yassin, et al, 1994). 2-Substituted benzoxazolinone as well as their corresponding quinazoline derivatives have been reported to exhibit biological activities such as antipyretic, antiinflammatory, anticancer and antimitotic agents (Wasfy, et al,1995).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of some surface active agents from long chain fatty amine

Eissa¹

2007

Grasas y Aceites

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Synthesis and performance of ester quaternary biodegradable softeners

Cited by 17 publications

References 3 publications

The rate of ring opening of γ‐and δ‐lactones derived from meadowfoam fatty acids

The rate of ring opening of γ‐and δ‐lactones derived from meadowfoam fatty acids

Ortho ester‐based cleavable cationic surfactants

Synthesis and evaluation of some surface active agents from long chain fatty amine

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