Patent GB-1072956-A (GB)
Title: Esters of diisocyanato carboxylic acids and reaction products thereof
IPC: C07C265/04
Filed: 1964-06-04
Abstract: The invention comprises (a) compounds of the formula <FORM:1072956/C2/1> wherein each R1 is an alkoxyalkyl radical or halogenated alkoxyalkyl radical and R2 is a C1 to C8 alkylene or C1 to C8 alkylidene radical; (b) compounds of the formula <FORM:1072956/C2/2> wherein R1 and R2 are as defined above; and (c) reaction products of a compound of the formula <FORM:1072956/C2/3> wherein R1 is an unsubstituted or halogen-substituted alkyl, alkoxyalkyl, aryl, alkaryl, or aralkyl radical, R2 is as defined above, and R3 is a hydrogen atom or a radical <FORM:1072956/C2/4> with a polyol material sufficient in amount to provide a NCO/OH ratio of from 0.1 to 6.0, the reaction between the diisocyanate and the polyol taking place at a temperature and for a period of time sufficient to effect the reaction between NCO and OH groups and to minimize the reaction between NCO groups and active hydrogens present on groups other than the hydroxyl groups.  The compounds of Formulae I, II and III may be prepared by reacting diamino compounds of the formula <FORM:1072956/C2/5> or acid-addition salts thereof, with phosgene in the presence of a solvent that will not react with phosgene under the reaction conditions employed.  The polyol reactants from which products C above are obtained are defined in the Specification to be compounds, polymers or mixtures in which all species contain two or more hydroxyl groups per molecule and no other functional groups that react at a significant rate with an isocyanate group at 25 DEG  C.ALSO:The invention comprises reaction products of a compound of formula <FORM:1072956/C3/1> wherein R1 is unsubstituted or halogen substituted alkyl, alkoxy-alkyl, aryl, alkaryl or aralkyl radical, R2 is a C1 to C8 alkylene or alkylidene radical, and R3 is a hydrogen atom or a radical <FORM:1072956/C3/2> , with a polyol meterial sufficient in amount to provide a NCO/OH ratio of from 0.1 to 6.0, the reaction between the diisocyanate and the polyol taking place at a temperature and for a period of time sufficient to effect the reaction between NCO and OH groups and to minimize the reaction between NCO groups and active hydrogen present on groups other than the hydroxyl groups.  The polyol reactants are defined in the Specification to be compounds, polymers or mixtures in which all species contain two or more hydroxyl groups per molecule and no other functional groups that react at a significant rate with an isocyanate group at 25 DEG  C. Adjuvants, e.g. antioxidants, pigments, plasticizers, catalysts and surfactants, may be included in the reaction mass.  Those isocyanate-terminated reaction products prepared from reactants having an NCO/OH ratio greater than unit may be foamed to produce cellular materials or cured with amines or polyols to produce elastomeric compositions.ALSO:A metal plate is coated with the reaction product obtained by heating butanediol-1,4,trimethylol propane, and 2, 6-diisocyanato dimethyl pimelate in a mixture of methyl Cellosolve acetate (Cellosolve is a trade mark) and xylene at 80 DEG  for 3 hours, adding phenol, cooling to room temperature and adding polypropylene glycol, and baking said coated surface at 400 DEG F in a circulating air oven (See Ex. 5). Wood and metal are coated with the reaction product obtained by heating 2, 5-diisocyanato n-decyl valerate and trimethylol propane at 70 DEG C for 3 hours, to which reaction product sufficient petroleum benzene has been added to give a solution of 65% solids and which has been pigmented with TiO2 (See Ex. 7).