Patent GB-886029-A (GB)
Title: Improvements in or relating to the manufacture of polymethane materials
Inventor: O'MANT DERRICK MICHAEL
IPC: C08L75/00
Filed: 1959-02-27
Abstract: A process for the manufacture of polyurethane materials by the interaction of an organic polyisocyanate and a hydroxyl-containing polymer containing at least two hydroxyl groups per molecule is characterized in that the interaction is carried out in the presence of a fully 4-N-substituted 4-aminopyridine as catalyst. The process can be used for the preparation of rigid or flexible, cellular or homogeneous products.  The N-substituents may be substituted or unsubstituted hydrocarbon or interrupted hydrocarbon radicals or the nitrogen may form a ring in conjunction with a difunctional substituent.  In the specific compounds listed the N-substituents specified are methyl, ethyl, allyl, pentenyl, hexyl, b -dimethylaminoethyl, b -N-pyrrolidinoethyl, and also included are 4-(N-piperidino, -pyrrolidino- and morpholino)-pyridines.  The pyridin ring may contain alkyl, substituted-amino, piperidino or morpholino substituents.  Bis compounds specified are N,N1-bis(4-pyridyl)-N,N1-dimethylpropylene diamine, N,N1-bis (4-pyridyl)-N:N1-dimethylethylene diamine, N, N1 - bis(4-pyridyl)-N:N1-dimethylhexamethylene diamine, N,N1-bis(4-pyridyl)-N:N1-dimethyl-b : b 1-diaminodiethyl ether, N,N1-bis(4-pyridyl)-N: N1-dimethyl -1:4-diamino-cyclohexane, N-(4-pyridyl)-N1-methyl-piperazine and N:N1-bis(4-pyridyl)-piperazine.  Preferred hydroxy-containing polymers are those wherein the majority of the hydroxyl groups are secondary, such as polypropylene diols and triols.  Lists of reactants for preparing polyester and polyesteramide starting materials are given.  The polyurethane-forming reaction mixture may contain catalysts such as dimethylcyclohexylamine, potassium carbonate, acetate or naphthenate, manganous and manganic acetylacetonates, dialkyl tin compounds; surface active agents, silicone oils, ethyl cellulose, pigments, plasticizers; fireproofing agents such as tri(b -chlorethyl) phosphate or antimony compounds and blowing agents such as volatile halogenoalkanes.  In Example (11) portions of a lacquer comprising a glycerol/glycol/adipic acid polyester and tolylene-2:4-diisocyanate in cyclohexanone and methyl ethyl ketone are gelled by adding 4-dimethylaminopyridine, 4-diethylaminopyridine and 4-N-pyrrolidinopyridine, respectively.ALSO:4-N-pyrrolidinopyridine is prepared by reacting pyrrolidine hydrochloride with 4-phenoxypyridine at 210 DEG C.-220 DEG C. for 10 hours and is converted to its picrate.  The base is used as a catalyst in the preparation of polyurethanes.ALSO:A process for the manufacture of polyurethane materials, including cellular products, by the interaction of an organic polyisocyanate and a hydroxyl-containing polymer containing at least two hydroxyl groups per molecule is characterised in that the interaction is carried out in the presence of a fully 4-N-substituted-4-aminopyridine as the catalyst.  The N-substituents may be substituted or unsubstituted hydro-carbon or interrupted hydrocarbon radicals or the nitrogen may form a ring in conjunction with a difunctional substituent.  In the specific compounds listed the N-substituents specified are methyl, ethyl, allyl, pentenyl, hexyl, b -dimethylaminoethyl and also included are 4-(N-piperidino-, pyrrolidino-and morpholino)-pyridine. The pyridine ring may contain alkyl, substituted-amino, piperidino or morpholino substituents. N,N1-Bis (4-pyridyl)- N,N1-dialkyl alkylene diamines and piperazines, N,N1-bis (4-pyridyl)-N : N1-dimethyl-b ,b 1-diamino-diethyl ether and N,N1-bis (4-pyridyl)-N,N1-dimethyl-1 : 4-diamino-cylcohexane are also specified P referred hydroxy-containing polymers are those in which the majority of the hydroxyl groups are secondary such as polypropylene diols and triols. Lists of reactants for preparing polyester and polyester amide starting materials are also given.  The reaction mixture may also contain other catalysts, surface-active agents, silicone oils, ethyl cellulose, pigments, plasticisers, fire-proofing agents e.g. trichlorethyl phosphate and antimony compounds and blowing agents such as volatile halogenoalkanes.