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of dry benzene was added and heating continued at ninety C. The viscous solution thus obtained Was diluted with 50 cc. dry benzene, and the polymer precipitated as white fibers by the addition of dry n-hexane.
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Included amongst such compositions used as beginning materials are these having triorganosilyl piperazine substitutions during which all methyl teams are substituted by both all ethyl teams or by all phenyl groups. Example 8 To illustrate the importance of the silyl substitution on the natural diamine, toluene-2,four-diisocyanate was reacted with para-phenylene diamine in the identical manner as was described in Example 7. For solubility causes, this reaction was carried out whereas the elements had been dissolved in N-methyl pyrrolidone.
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The solutions additionally could also be used to spin fibers of the polysilylurea by way of spinnerettes and volatilizing the solvent. Polysilylureas of Formula IV have molecular weights ranging from one thousand to 500,000 or more. Depending on the substituents which R, R and Z, and m symbolize, a lot of such polymers could have softening factors of round C.
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With respect to Z alone, when it’s part of a cyclic radical containing the two nitrogen atoms, Z can be, for example, the divalent ethylene radical, both the methylene radical and the higher alkylene radicals, such as the pentamethylene radical when the 2 nitrogens are closer together within the ring, and so on. Furthermore, it should be recognized that m is 1 solely when the grouping of Formula III is acyclic, whereas in is zero, only when the latter grouping is cyclic in nature. Where R is an arylene radical, any substituents thereon could be in any of the positions vicinal, symmetrical and asymmetrical to the valences of the arylene radical related to the isocyanate radicals. The valences of the arylene group could also be various in ortho-, meta-, or para-positions with the metaor para-positions 7 being the preferred association.
In order to kind the polysilylurea, the diisocyanate is then reacted with the triorganosilylamine of Formula II employing a molar ratio of about 1 mol of the triorganosilylamine per mol of the diisocyanate. There is thus obtained a solution of the desired polysilylurea which could be precipitated from the solvent by the addition of a non-solvent for the polysilylurea, such as n-hexane.
This ought to be contrasted with the solubility of the polysilylurea of EX- ample 7 which was soluble in a variety of solvents, a property which is important for the formation of high molecular Weight movies and fibers. Example 6 To a mixture of 5.05 grams (0.02 mol) N,N’-bis-p-phenylenediamine and three.20 grams (0.02 mol) para-phenylenediisocyanate was added cc. The response mixture was heated with stirring at ninety C. After 2 hours at this temperature, the mixture turned fairly viscous, after which 10 cc.
These films had a tensile energy of about 6485 p.s.i. Exposure of the polysilylurea to moist air gave a solid polyurea of recurring items of the formula This polyurea, which could be heated at temperatures as much as virtually 260 C. earlier than any evidence of decomposition, was immune to most solvents, though soluble in such solvents as dimethyl formamide. Films and fibers were useful as electrical insulation and for prime temperature cloths, respectively, might be forged or spun from solutions of this polyurea in dimethyl formamide. By using the diamine as the hydrolyzing agent, it’s converted instantly into a disilyl diamine which can then be used to make further polysilylureas by response with the suitable diisocyanate. In addition, when Z with the two nitrogens in a cyclic natural radical containing the nitrogen within the ring structure such groupings can be, for example, the piperazyl radical of the formulation where R is a monovalent hydrocarbon radical corresponding to these recited for R , and p is a complete number from to four, inclusive.
This polymer when dried under vacuum under anhydrous circumstances, was a polysilylurea composed of recurring units of the formulation. The formation of the polyurea containing fewer silyl teams than the starting polysilylurea, or a polyurea completely freed from silyl groups, can be completed by exposing the polysilylurea to air, ideally of from 70 to relative humidity. This results hydrolysis of the triorganosilyl teams to kind the corresponding disiloxane with the substitution of a hydrogen atom in place of the triorganosilyl group on a nitrogen atom. Where the polysilylurea is pretty thick in cross-part, the scission of the triorganosilyl groups by hydrolysis is extra rapid at the surface than within the matrix of the polysilylurea article.
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Such fillers could also be added in quantities ranging, by weight, from 0.1 to 200 elements of filler per components of polymer. Suitable plasticizers could also be added as could extenders of resins, for example, cumar, indene, and cumarindene resins. These polyureas have good heat stability, are infusible, and insoluble in all and to common natural solvents. Example 10 The compound N,N-bis-p,p-diaminodiphenyl is prepared by forming a suspension of 184 grams of p,p’-diaminodiphenyl in 1.5 liters of dry benzene with 250 grams triethylamine, adding 220 grams trimethylchlorosilane, and heating the mixture of components in the identical manner as in Example 1. This will yield a composition having the method Example 11 as evidenced by the analyses; p.c C, sixty six.5 (sixty six.3); percent H, eight.9 (8.9); percent N, 8.5 (8.three); p.c Si, 16.8 (16.6).