Reaction of Epichlorohydrin with Ammonia, Aniline, and Diethanolamine

McKelvey, John B.; Webre, Beverly G.; Benerito, Ruth R.

doi:10.1021/jo01078a035

Cited by 23 publications

(13 citation statements)

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“…Additionally, surface hydrophobicity may not alone suffice for biocidal or bioremadial requirements. GG when reacted with 1-chloro-2,3-epoxypropane in presence of concentrated aqueous ammonia, Strukov reaction (McKelvey et al, 1960) led to a new cationic guar gum GGAA (II). Similar reactions were extensively used in development of water resistant cellulose coatings for application in paper and textiles industry (Berni et al, 1969).…”

Section: Synthesis Of Guar Gum Benzamide (Ggba)mentioning

confidence: 99%

New water resistant biomaterial biocide film based on guar gum

Das

Ara

Dutta

et al. 2011

Bioresource Technology

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Section: Synthesis Of Guar Gum Benzamide (Ggba)mentioning

confidence: 99%

New water resistant biomaterial biocide film based on guar gum

Das

Ara

Dutta

et al. 2011

Bioresource Technology

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“…' 4. E~o.rides and Wet Creasr R~~oz~c~r~Õ ne must exercise care in comparing epoxide finishes with formaldehyde finishes, because here we are dealing with a class of compounds that vary widely in reactivity for reasons pointed out previously [36,38,40].…”

Section: Cotton Cell Ulose ~And Water 'mentioning

confidence: 99%

The Nature of Wet Crease Recovery in Cotton—A Review

McKelvey

1964

Textile Research Journal

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Intro4uction, Unfinished cotton fabrics that have heen desizecl, ' scoured, and bleached are usually less resilient when wet tjiati when conditioned to &dquo;dryness&dquo; at 65% RH at 25° C. Thus 80 X 80 fabric has been found to have dry conditioned recovery angles of 195°' (warp plus filling) and 165 (W + F) when wet.On occasion, other memlers of this laboratory have observed cotton fahric in which the dry and wet crease recovery angles were of equal value and one sample at least with the wet recovery angle higher than the dry value. These anomalies are helieved to le due to the severity of, or the lack of severity of, the purification process and perhaps to the structure and history of the fabrics. It has been, experimentally shown that numerous reagents cause an elevation of both the dry and wet recovery angles, and the reagents which have been successful in textile finishing for wash-wear have heen dior '. poly functional. However, in the field o~ epoxide and formaldehyde finishing it has been found possiblẽ to elevate the wet crease angle without changing the dry angle very much, although sometimes with epoxide-treated fabrics the dry angle is definitely less than that of the untreated control. Gross deposition of re~n to cause &dquo;spot welding&dquo; of fibers or l~cril>l~eral deposition, as described by Steele 1701 I and Marsh [41], will not be considered in tliis discttssion. although noted in passing.From the number of references in the literature to wet crease recovery alone it would appear that the phenomenon has been rather widely observed over a considerable period of time. And since there is such a variety of reagents that can cause it under many different conditions of reaction, it is possible that what is being observed are several effects superimposed upon one another. The two most common reagents capable of making cotton crease resistant in the wet state alone are formaldehyde (or donors of it) and epichlorohydrin (or its precursors). However, as this review will show, the choice of a reagent is not limited to these two.IZeference will also 1>e made to effects of alkali alone on cotton, and, as will be pointed out, strong alkali (15-25% NaOH ) is used as a &dquo;catalyst&dquo; in preparing various cellulose derivatives, particularly the ethers. It is possible to cause improvement in 1 One of the laboratories of the Southern Utilization Research and Development Division,

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“…Detailed procedures for the preparation of TCHA, TCHAC, TEPA, and the reaction products formed between ammonium chloride and epichlorohydrin in aqueous medium have been described previously [10] .…”

Section: Experimental Chemicalsmentioning

confidence: 99%

“…Ammonium chloride and epichlorohydrin were also reacted in absolute methanol as well as in aqueous media as previously described [10]. However, tls the former reaction proceeded and NH,CI went into solution, considerable carbonyl compounds were formed, and this scheme was not pursued.…”

Section: Nhcl and Epichlorobydri»mentioning

confidence: 99%

“…Since the highest Yield of TEPA was only 56%, application of its .In this laboratory, the reaction of epichlorohydrin With ammonia in various reaction media was investigated. The preparations of the hydrochloride of N,N,N -tris (3-chloro-2-hydroxypropyl) amine (TCHAC), and N,N,N-tris(2,3-epoxypropyl)amine (TEPA) from the crude reaction product (TCHA) of ammonia and epichlorohydrin in a 1: 3 mole ratio in methanol were described, and evidence was obtained for the formation of 1,3-dichloro-2-propanol when ammonia or ammonium chloride and epichlorohydrin reacted in an aqueous medium [10]. The reactions may be summarized by the following equations:…”

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confidence: 99%

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