Reactions of fatty acid chlorides. I. Preparation of fatty acid anhydrides

Sonntag, Norman O. V.; Trowbridge, J. R.; Krems, Irving J.

doi:10.1007/bf02545703

Cited by 26 publications

(4 citation statements)

References 20 publications

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“…One technique being researched for improving the surface properties is chemical grafting using fatty acid chlorides, which allows substances and surfaces to be esterified [12][13][14][15][16][17]. This technique is well known for the modification of starch and cellulose, for example for increasing the hydrophobicity [18][19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Water Repellence and Oxygen and Water Vapor Barrier of PVOH-Coated Substrates before and after Surface Esterification

et al. 2014

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This study investigates chemical grafting with fatty acid chlorides as a method for the surface modification of hydrophilic web materials. The resulting changes in the water repellence and barrier properties were studied. For this purpose, different grades of polyvinyl alcohol (PVOH) were coated on regenerated cellulose films ("cellophane") and paper and then grafted with fatty acid chlorides. The PVOH grades varied in their degree of hydrolysis and average molecular weight. The surface was esterified with two fatty acid chlorides, palmitoyl (C16) and stearoyl chloride (C18), by chemical grafting. The chemical grafting resulted in water-repellent surfaces and reduced water vapor transmission rates by a factor OPEN ACCESSPolymers 2014, 6 2765 of almost 19. The impact of the surface modification was greater for a higher degree of hydrolysis of the polyvinyl alcohol and for shorter fatty acid chains. Although the water vapor barrier for palmitoyl-grafted PVOH was higher than for stearoyl-grafted PVOH, the contact angle with water was lower. Additionally, it was shown that a higher degree of hydrolysis led to higher water vapor barrier improvement factors after grafting. Furthermore, the oxygen permeability decreased after grafting significantly, due to the fact that the grafting protects the PVOH against humidity when the humidity is applied on the grafted side. It can be concluded that the carbon chain length of the fatty acid chlorides is the limiting factor for water vapor adsorption, but the grafting density is the bottleneck for water diffusing in the polymer.

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Section: Introductionmentioning

confidence: 99%

Water Repellence and Oxygen and Water Vapor Barrier of PVOH-Coated Substrates before and after Surface Esterification

et al. 2014

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“…EXPERIMENTAL Preparation of the diethanolamides. The preparation of the fractionated acid chlorides from the fatty acids and phosphorus trichloride has been described previously (12). The acid chloride, 0.1 mole, was dissolved in 25 ml.…”

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confidence: 99%

Fatty Acid Derivatives of Diethanolamine

Trowbridge¹,

Falk²,

Krems³

1955

J. Org. Chem.

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“…triethylamine or pyridine) results in an almost complete conversion into symmetric anhydrides by much milder conditions, although a negligible amount of free acid is always present in the reaction mixture. 22, 23 Therefore, we performed the synthesis of anhydride functional a,w-diene monomer 1 from 10-undecenoic acid and undec-10enoyl chloride with triethylamine as the acid scavenger. It should be noted that water-free conditions are essential, especially concerning the solvents, in order to prevent product hydrolysis.…”

Section: Resultsmentioning

confidence: 99%