Reaction of Cellulose with Dimethylol- and Monomethylolureas

Steele, Richard; Giddings, Lorrain E.

doi:10.1021/ie50553a033

Cited by 31 publications

(12 citation statements)

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“…The low value of the CH;!O: N/2 ratio and low degrees of substitution indicate either a high proportion of bound material that does not form cross links or the formation of relatively long cross links. This is particularly evident with dimethylol urea sizes are approximately the same as previously reported for these two cross-linking agents [3,5 ) . .…”

Section: Resultssupporting

confidence: 85%

“…This is based on the assumption that the cross links contain no more thpn a single methylene group and that there are no formaldehyde residues on the fabric that are not part of a cross link. These assumptions are supported hy the work of Wagner and Pacsu [f>~ and Cruntfest and Gagliardi [4~, although the latter workers report that longer formal~lehyde cross links are formed at levels of suhstitution higher than encountered in this work Less simple calculations must he made with the series of fabrics treated with dimethylol ethyleneurea and dimethylol urea, as both of these compounds have been reported to form multiple unit cross links [ 3,5]. For both treatments, it was aS~l1med that the.…”

Section: Resultssupporting

confidence: 63%

“…after immediate recovery is completed remains close to a constant value until permanent set approaches zero and then decreases. 5. Little or no change :OCCUFS in these elongation values after maximum crease recovery angle is attained.…”

Section: Relation Of Elastic Properties To Wrinkle Resistancementioning

confidence: 97%

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Effects of Cross-Linkage in Wrinkle-Resistant Cotton Fabrics

Frick

Andrews

Reid

1960

Textile Research Journal

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The cross-linking of cellulose in cotton fabric with three wrinkle-resistance finishing agents has been investigated. The three agents used were dimethylol urea, dimethylol ethyleneurea, and formaldehyde. With all three compounds, maximum crease recovery angles are obtained with a substitution of 0.04-0.05 cross links per anhydroglucose unit. As crease recovery angles increase, the elongation and permanent set caused by an 8-kg. tensile load on a 1-in. fabric strip decreases. Permanent set approaches zero near 135° warp crease recovery. Changes in the load-elongation curves indicate elastic modulus increases as crease recovery angles increase. Treatment of fabric to the same crease recovery angles with the three compounds reduces tearing and breaking strengths to different extents. The differences are due to different amounts of cellulose degradation caused by the aciclic catalyst systems and not to the structure of the cross links.

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Section: Resultssupporting

confidence: 85%

Section: Resultssupporting

confidence: 63%

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Effects of Cross-Linkage in Wrinkle-Resistant Cotton Fabrics

Frick

Andrews

Reid

1960

Textile Research Journal

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“…This seems probable, since the catalysts are effective only with methylol urea precondensates, which normally contain considerable percentages of free formaldehyde. Steele and Giddings [ 17] have asserted that the cross-linking mechanism is more effective in crease-resisting cotton but not in the case of rayon.…”

Section: Discussionmentioning

confidence: 99%

The Application of Grease-Resistant Finishes to Cotton

Smith¹

1956

Textile Research Journal

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“…, A very powerful argument in favor of the crosslinking hypothesis is the general experience that only difunctional reactants are particularly efficient in improving the resilience of cellulosic fabrics. For example, Steele and Giddings [42,43] found that monomethylol urea increased the crease recovery of cotton to a much lesser extent than dimethylol urea. Most known cellulose cross-linkers are able to polymerize when reacted in the absence of cellulose.…”

mentioning

confidence: 99%

Some Theoretical Considerations of Cellulose Cross-Linking

Garden¹,

Steele²

1961

Textile Research Journal

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Much available chemical evidence supports the hypothesis that covalent cross-linking is the best way to improve the resilience of cellulosic fabrics. This paper reviews the theories relating physical properties to cross-linking in rubbery polymers and shows that they apply in some qualitative aspects to cellulose. Particularly, the observed changes in swelling, solubility, modulus, tensile strength, and resilience are consistent with these theories.On the basis of published data, the concentration of intermolecular cross links is estimated ; it is found that at least every twenty-fifth accessible anhydroglucose unit has to be intermolecularly cross-linked when maximum crease recovery values are attained. In rubbery polymers, substantial changes in mechanical properties are obtained at much lower levels of cross-linking. This difference between cellulose and rubbers in response to cross-linking is probably due to the polar nature of cellulose.IT IS widely accepted that cross-linking is the most efficient method to impart high resilience, good crease recovery, and dimensional stability to cellulose fabrics. The cross-linking hypothesis was first advanced by Meunier and Guyot [29] J in 1929 for the formaldehyde-cellulose reaction. It obtained wider attention in 1948 through the work of Cameron and Morton [5], who based their conclusions on the lowered moisture regain, water imbibition, and solubility of rayon samples reacted either with urea-formaldehyde or melamine-formaldehyde precondensates or with formaldehyde or glyoxal alone. It had, however, been known [2, 8, 511 and has reently been confirmed by Reeves et al. [ 36] that wet state treatments of cellulose with formaldehyde . increase the moisture regain and water imbibition. Furthermore, reduction in the solubility of cellulose may also be caused by simple single-ended substituton on the cellulosic hydroxyls. The evidence provided by Cameron and Moron was therefore not unequivocal. , A very powerful argument in favor of the crosslinking hypothesis is the general experience that only difunctional reactants are particularly efficient in improving the resilience of cellulosic fabrics. For example, Steele and Giddings [42,43] found that monomethylol urea increased the crease recovery of cotton to a much lesser extent than dimethylol urea. Most known cellulose cross-linkers are able to polymerize when reacted in the absence of cellulose. It has been argued that these compounds improve resilience by forming polymers within the fiber (25J ] and thus stabilizing the physical entanglements of the molecules ( 28 J . One could imagine that complicated cross-linked structures are obtained by polymerizing difunctional reactants and that the resulting three-dimensional networks are more efhcient in stabilizing the fabric than the linear polymers derived from monofunctional reactants. However, this argument is weakened by the available data indicating that certain reactants do form covalent links with cellulose. This has been shown by Wagner and Pacsu [49] by methylation of...

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Reaction of Cellulose with Dimethylol- and Monomethylolureas

Cited by 31 publications

References 1 publication

Effects of Cross-Linkage in Wrinkle-Resistant Cotton Fabrics

Effects of Cross-Linkage in Wrinkle-Resistant Cotton Fabrics

The Application of Grease-Resistant Finishes to Cotton

Some Theoretical Considerations of Cellulose Cross-Linking

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