Patent GB-865726-A (GB)
Title: Process for the manufacture of plastics from polyhydroxy compounds and polyisocyanates
IPC: C08G18/10
Filed: 1958-08-07
Abstract: A process for the production of polyhydroxy compounds comprises reacting at least one polyalkalene ether glycol containing free hydroxyl groups with an excess (calculated on the hydroxyl groups) of at least one polyisocyanate, and reacting the initial adduct so obtained with an excess (calculated on the free NCO groups of the initial product) of at least one secondary aminoalcohol.  ("Secondary aminoalcohol" is used to mean an aminoalcohol which has a secondary amino group (or groups) and a primary hydroxyl group (or groups)). The products are used to produce plastics (foamed or homogenous) by reaction with polyisocyanates and, if necessary, crosslinking agents. The polyalkylene ether glycols can be those obtained by the polymerization of alkylene oxides such as ethylene oxide, propylene oxide, butylene oxides, styrene oxide, epichlorhydrin or tetrahydrofuran or by reaction of alkylene oxides with polyfunctional alcohols, aminoalcohols or amines.  The ethers can be used in admixture with other polyvalent hydroxy compounds, such as 1, 4-butylene glycol, trimethylol propane, pentaerythritol, tartaric acid esters and castor oil.  Di-isocyanates, which may be employed concurrently with tri- and higher-functional p  polyisocyanates are listed.  Secondary aminoalcohols specified are N-methyl and N-ethyl ethanolamines, N-butyl-ethanolamine, N-oxyethyl aniline, N-isopropyl propanolamine-1, 3, N-cyclohexyl propanolamine-1, 3 and diethanolamine.  The first stage of the process can be effected continuously and in the presence of solvents such as ketones, esters, hydrocarbons or chlorinated hydrocarbons and catalysts such as mercury acetate, titanium tetrabutylate or chloride or iron, copper, cobalt or manganese acetylacetonates.  The ratio of NCO groups to OH groups is preferably about 2 to 1.  In the second stage the quantity of secondary aminoalcohol is chosen so that only the aminohydrogen reacts with the NCO groups of the initial adducts, by using a ratio between NCO groups and reactive hydrogen atoms of at least 1 : 2.  In typical Examples (1) polypropylene glycol is reacted with excess toluylene-2 : 4-diisocyanate in benzene in the presence of benzoyl chloride and iron acetyl acetonate.  After reacting at 120 DEG C. the product is cooled, further benzoyl chloride is added, and the product is reacted with excess N-hydroxyethyl aniline. The polyhydroxy compound obtained is reacted with toluene diisocyanates, ethyl morpholine, and water containing sulphonated castor oil and potassium hydroxide, to give a foam; (5) a polyhydroxy compound similarly prepared from toluylene-2 : 4-diisocyanate and a mixture of polypropylene glycol and castor oil is dissolved in ethyl acetate together with a masked polyisocyanate and the solution is heated as a lacquer coating on a rubber plate.ALSO:A process for the production of polyhydroxy compounds comprises reacting at least one polyalkylene ether glycol containing free hydroxyl groups with an excess (calculated on the hydroxyl groups) of at least one polyisocyanate, and reacting the initial adduct so obtained with an excess (calculated on the free NCO groups of the initial product) of at least one secondary aminoalcohol.  ("Secondary amino-alcohol" is used to mean an aminoalcohol which has a secondary amino group (or groups) and a primary hydroxyl group (or groups)).  The products are used to produce plastics (foamed or homogeneous) by reaction with polyisocyanates and, if necessary, cross-linking agents.  The polyalkylene ether glycols can be those obtained by the polymerisation of alkylene oxides such as ethylene oxide, propylene oxide, butylene oxides, styrene oxide, epichlorhydrin or tetrahydrofuran or by reaction of alkylene oxides with polyfunctional alcohols, aminoalcohols or amines.  The ethers can be used in admixture with other polyvalent hydroxy compounds, such as 1,4-butylene glycol, trimethylol propane, pentaerythritol, tartaric acid esters and castor oil.  Di-isocyanates, which may be employed concurrently with tri- and higher-functional polyisocyanates are listed.  Secondary aminoalcohols specified are N-methyl and N-ethyl ethanolamines, N-butyl-ethanolamine, N-oxyethyl aniline, N-isopropyl propanolamine-1, 3, N-cyclohexyl propanolamine-1, 3 and diethanolamine.  The first stage of the process can be effected continuously and in the presence of solvents such as ketones, esters, hydrocarbons or chlorinated hydrocarbons and catalysts such as mercury acetate, titanium tetrabutylate or chloride or iron, copper, cobalt or manganese acetylacetonates.  The ratio of NCO groups to OH groups is preferably about 2 to 1.  In the second stage the quantity of secondary aminoalcohol is chosen so that only the amino-hydrogen reacts with the NCO groups of the initial adducts, by using a ratio between NCO groups and reactive hydrogen atoms of at least 1 : 2.