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Trimerization of aromatic isocyanates catalyzed by certain ammonium salts
| Details |
Inventors: Fabris, Hubert J.; Maxey, Edwin M.; Uelzmann, Heinz;
Assignee: The General Tire & Rubber Company (Akron, OH)
Primary Examiner: Welsh; M. J.
Assistant Examiner:
Attorney, Agent or Firm:
Quaternary ammonium salts or inorganic and organic oxygen acids having pK values (where pK is the negative log of the dissociation constant) for at least one of the dissociable hydrogen atoms equal to or greater than 2.0 in aqueous solution are employed as extremely efficient catalysts for trimerization of organic isocyanates, particularly aromatic isocyanates, to isocyanurates and for urethane formation. |
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DETAILED DESCRIPTION We claim: 1.
A method which comprises reacting organic isocyanates in contact with at least 0.
01 part by weight of said isocyanates of a compound displaying catalytic activity for exothermic cyclic trimerization of organic isocyanates and for urethane formation, said compound corresponding to the structural formula (NR.
sub.
4).
sub.
y A in which A is an anion derived from an acid having a pK value, in aqueous solution at substantially room temperature, of 2.
0 or greater and being free of substituents which can react with isocyanates under conditions of trimerization and being selected from the group consisting of inorganic oxygen acids, carboxylic acids and carbonic acid, each R is any organic group other than A and free of any substituents and functional groups which can react with isocyanates under conditions of trimerization, no more than one R per N containing an aromatic ring attached directly to N, and y is a whole number equal in value to the valence of A.
2.
A method in accordance with claim 1 wherein each R is a hydrocarbon group containing no more than about 18 carbon atoms, the total number of the carbon atoms of the four R groups on any N being no more than about 25.
3.
A method in accordance with claim 2 wherein each R is a hydrocarbon group containing no more than about 8 carbon atoms, the total number of the carbon atoms of the four R groups on any N being no more than about 12.
4.
A method in accordance with claim 2 wherein the acid from which A is derived has a pK value in aqueous solution at essentially room temperature of from about 4 to about 10.
5.
A method in accordance with claim 1 wherein said organic isocyanates are polyisocyanates and said reaction takes place in contact with from 20 to 60 parts by weight per 100 parts by weight of said isocyanates of hydroxylated ingredients selected from the group consisting of aliphatic polyethers, aliphatic polyesters and polyepoxides, said hydroxylated ingredients having a number average molecular weight from about 250 to 12,000
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