Accession Number : ADA308676

Title :   Chlorophenylalkyl-Substituted Carboxylic Acids and Silanes Designed as Adhesion Promoters,

Corporate Author : NAVAL RESEARCH LAB WASHINGTON DC

Personal Author(s) : O'Rear, J. G. ; Sniegoski, P. J. ; James, F. L.

PDF Url : ADA308676

Report Date : 26 DEC 1967

Pagination or Media Count : 17

Abstract : The six new carboxylic acids of this study feature a terminal p-chlorophenyl substituent, a polymethylene spacer, and either one or two carboxyl groups. The carboxyl groups may be replaced by -SiCl3 or -Si(OC2H5)3 groups. Such structures are designed to promote adhesion between a solid substrate and an organic resin by forming a monolayer strongly attached to the substrate and exposing a chlorophenyl outer surface which is easily wet by the resin. Multistep syntheses were carried out for the preparation of monocarboxylic acids p-ClC6H4(CH2)n-1 CO2H, where n is 12, 14, 18, and 20, via Friedel-Crafts reactions and Wolff-Kishner reductions. Some also used a subsequent LiAlH4 reduction. Succinic and glutaric acids substituted in the alpha position by a p-ClC6H4(CH2)12-substituent were prepared through malonic ester syntheses. The acids were characterized by melting points, neutralization equivalents, and elemental assays. NMR spectra showed that the chlorine substitution is at least 95% para. Gas-liquid chromatography was used to assess the purity of both intermediates and products; most of the acids had purities exceeding 97.5%. Principal impurities were the unchlorinated analogs and lower homologs. The Friedel-Crafts method was employed to prepare p-ClC6H4(CH2)2SiCl3; this compound and its trimethoxy and triethoxy analogs were characterized by conventional criteria.

Descriptors :   *ADHESION, *SILANES, *CARBOXYLIC ACIDS, *CHLORINE COMPOUNDS, POLYMERS, SUBSTRATES, SOLIDS, IMPURITIES, PURITY, LIQUID CHROMATOGRAPHY, SUBSTITUTES, PHENYL RADICALS, MELTING POINT, GAS CHROMATOGRAPHY, ALKYL RADICALS, CARBOXYL RADICALS, GLUTARIC ACID, SUCCINIC ACID, FRIEDEL CRAFTS REACTIONS.

Subject Categories : Organic Chemistry
      Polymer Chemistry
      Adhesives, Seals and Binders

Distribution Statement : APPROVED FOR PUBLIC RELEASE