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United States Department of Agriculture

Agricultural Research Service

Title: Epoxy Phosphonate Crosslinkers for Providing Flame Resistance to Cotton Textiles

Authors
item Chang, Sechin
item Sachinvala, Navzer - COLLABORATOR
item Sawhney, Amar
item Parikh, Dharnidhar
item Jarrett, William - UNIV. OF SOUTHERN MISS
item Grimm, Casey

Submitted to: Polymers for Advanced Technologies
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: October 11, 2006
Publication Date: June 6, 2007
Citation: Chang, S., Sachinvala, N.D., Sawhney, A.P., Parikh, D.V., Jarrett, W., Grimm, C.C. 2007. Epoxy Phosphonate Crosslinkers for Providing Flame Resistance to Cotton Textiles. Polymers for Advanced Technologies. 18:611-619.

Interpretive Summary: It is particularly useful to design and develop new environmentally friendly organic compounds and formulations that enable textiles and other articles of commerce to be flame resistant. Towards this goal two new compounds were prepared via short two-step syntheses, and formulated in aqueous solutions to make plain weave, twill, and fleece fabrics pass the vertical flame test. We achieved this ultimate result and in the process explained our design criteria, the chemistry to achieve the new compounds, and employed standard test methods to verify our results. The new compounds and their formulations will be of interest and use to professionals engaged in new materials designing in academia; and the plastics, composites, and textile industries to create new marketable uses for cotton fibers and fabrics to serve emerging needs.

Technical Abstract: Two new monomers (2-methyl-oxiranylmethyl)-phosphonic acid dimethyl ester (3) and [2-(dimethoxy-phosphorylmethyl)-oxyranylmethyl]-phosphonic acid dimethyl ester (6) were prepared and used with dicyandiamide (7) and citric acid (8) to impart flame resistance to cotton plain weave, twill, and 80:20-cotton/polyester fleece fabrics. Monomers 3 and 6 were prepared from methallyl chloride (1) and 3-chloro-2-chloromethylpropene (4) respectively via a two-step phosphorylation epoxidation sequence in 79.3 and 67.5% overall yields. 1H and 13C nuclear magnetic resonance (NMR) and gas chromatographic mass spectrometry (GCMS) data were used to confirm their structures. Decomposition of monomers 3 and 6 in nitrogen by thermogravimetric analysis (TGA) occurred at 110 and 2208C, respectively. The mixtures of 3:7:8 and 6:7:8 (in 2:1:1 ratio) exhibited peak-curing temperatures by differential scanning calorimeter (DSC) at 125 and 1508C and the temperatures were deemed suitable for curing treated fabrics without marring them. Flame-retardant treatments were applied by the pad-dry-cure methods. All untreated fabrics showed limiting oxygen index (LOI) values of about 18% oxygen in nitrogen. For formulations with monomer 3, LOI values for the three types of treated fabrics were greater than 25.5% when add-on values for the formulation were 17.4, 12.7, and 21.1%. For formulations comprising monomer 6, LOI values were greater than 28.6% when add-on values for the formulation were 18.3, 13.1, and 16.7%. With the formulation comprising monomer 3, the three fabrics passed the vertical flame test when add-on values were 21.6, 12.7, and 23.5%, respectively; and with the formulation comprising monomer 6, they passed the vertical flame test when add-on values were 13.8, 8.4, and 18.0%. In all cases char lengths of fabrics that passed the vertical flame test were less than 50% of original length and after-flame time was 0 sec and after-glow time was less than 2 sec.

Last Modified: 9/20/2014
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