Patent GB-977958-A (GB)
Title: A process for the preparation of partially esterified amino alcohols
IPC: C08G63/685
Filed: 1962-05-14
Abstract: The invention comprises partially esterified amino di-alcohols of the formula <FORM:0977958/C1/1> wherein R1 and R2 are similar or dissimilar saturated hydrocarbon radicals, which may also be directly attached to each other, R3 and R4 each represent an alkyl or cycloalkyl group or a hydrogen atom, A and B are similar or dissimilar alkylene groups, R5 represents a hydrogen atom, a group of the formula <FORM:0977958/C1/2> a monovalent hydrocarbon radical or a monovalent hydrocarbon radical substituted by hydroxyl or amino groups, said amino groups being substituted if desired by groups of the formula <FORM:0977958/C1/3> R6 represents the same group as specified for R5 or a group -NR7R8, and R7 and R8 represent a hydrogen atom, a monovalent hydrocarbon radical or a group of the formula <FORM:0977958/C1/4> The above compounds are prepared by reacting an amine of the formula R5R6NH with the intermediate product formed by reacting an epoxy halogen alkane or a halohydrin from which an epoxy halogen alkane may be formed by liberation of hydrogen halide on the one hand with a saturated aliphatic monocarboxylic acid of the formula <FORM:0977958/C1/5> or a salt thereof on the other hand. The reaction may be conducted in the presence of catalysts such as tributylamine.ALSO:Partially esterified amino di-alcohols of the formula <FORM:0977958/C3/1> , wherein R1 and R2 are similar or dissimilar saturated hydrocarbon radicals, which may also be directly attached to each other, R3 and R4 each represent a hydrogen atom or an alkyl or cycloalkyl group, A and B are similar or dissimilar alkylene groups, R5 represents a hydrogen atom, a group of the formula <FORM:0977958/C3/2> , a monovalent hydrocarbon radical or a monovalent hydrocarbon radical substituted by hydroxy or amino groups, said amino groups being substituted if desired by groups of the formula <FORM:0977958/C3/3> , R6 represents the same groups as specified for R5 or a group -NR7R8, and R7 and R8 represent a hydrogen atom, a monovalent hydrocarbon radical or a group of the formula <FORM:0977958/C3/4> , are used alone or in the form of complexes with boron trifluoride as plasticizers or curing agents for polyepoxy compounds, as components of polyurethanes and as components of alkyd resins. The polyepoxy compounds may be cured in the presence of further ingredients such as bitumens, cracked bitumens, talcum, titanium dioxide, organic solvents such as alcohol, benzene, toluene, xylene and methyl isobutyl ketone and/or monoepoxy compounds such as butyl glycidyl ether, phenyl glycidyl ether and glycidyl ethers of branched monocarboxylic acids to provide products which may be used as paints for concrete floors and for the interior of tanks, wet-strength and tear-resistance agents for cellulose and polyamide fabrics and paper (including nylon fibre paper), casting resins and laminates.  Specified polyepoxy compounds are poly (epoxyalkyl) ethers of diphenylol propane, -ethane and -methane, diphenylol sulphone, hydroquinone, resorcinol, dihydroxydiphenyl, dihydroxynaphthalenes, novolacs, resols, ethylene glycol, glycerol and trimethylolpropane; diglycidyl esters of phthalic, terephthalic and adipic acids; epoxidized linseed and soybean oils; diepoxybutane; epoxidized vinylcyclohexane; diglycidyl ether; and the (3, 4-epoxy-6-methylcyclohexyl)-methyl ester of 3, 4-epoxy-6-methyl-cyclohexane carboxylic acid.  The above partially esterified.  Polyurethanes are prepared by reacting the above specified partially esterified amino-dialcohols with the following polyisocyanates:-toluene, hexamethylene, diphenylmethane, naphthalene, meta-phenylene, diphenyl, diphenyl ether, dianisidine, ethylene and diethyl ether diisocyanates, triphenylmethane triisocyanate, mixtures of 2, 4- and 2, 6-toluene diisocyanate, and polyisocyanates formed by reacting ethylene glycol, glycerol and 1, 2, 6-hexane triol with any of the above-specified isocyanates.  The polyurethanes may be formulated into foam, paint and lacquer compositions together with fillers, pigments and solvents such as xylene and ethyl acetate. Polyesters are prepared by reacting the above specified partially esterified amino-dialcohols, alone or in conjunction with diethylene glycol, dipropylene glycol or glycerol, with citric, trimellitic, pyromellitic, phthalic, isophthalic, terephthalic, succinic, adipic, maleic, tetrahydrophthalic or diglycolic acids or their anhydrides, dimerized fatty acids of drying oils and Diels-Alder adducts of maleic acid with terpenes, cyclopentadienes, hexachlorocyclopentadiene or mixtures thereof, using temperatures of between 120-270 DEG C. and, if desired, a xylene solvent.  The resulting polyester resins may be used for paints, lacquers and varnishes in combination with pigments such as titanium white, diluents such as xylene, phenol-form-aldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins and thickeners.ALSO:Polyepoxide resins cured with specified partially esterified amino alcohols and containing as further ingredients cracked bitumen, titanium dioxide or talcum are spread on to concrete floors to provide a surface which cures within 24 hours to give a hard, flexible and wear-resistant coating.  A polyurethane lacquer based on the reaction product of a polyisocyanate and a specified partially esterified amino alcohol is made up to brushing consistency with water-free xylene or ethyl acetate and applied to steel test panels and either cured at room temperature for 2-3 days or baked at 100-150  DEG C. for 30-40 minutes to provide a colourless, hard and flexible coating.  Alkyd resins prepared from phthalic anhydride, specified partially esterified amino alcohols, glycerol or triethylene glycol and xylene are formulated into stoving enamels with urea formaldehyde resin and titanium white and are applied to steel panels and baked at 150  DEG C. to provide hard, flexible coatings.ALSO:Improved wet-strength and non-tearing characteristics are imparted to cellulose and polyamide fabrics and to paper, including paper formed from nylon fibres, by impregnation with a 5% by volume solution of a polyepoxy compound in an organic solvent such as alcohol, benzene, toluene, xylene or methyl isobutyl ketone, which solution also contains from 10 to 30% by volume of a specified partially esterified aminodi-alcohol curing agent, followed by a curing treatment, e.g. by heating to 100 DEG C. Alternatively, monoepoxy compounds may be used to reduce the viscosity of the uncured polypoxy compound in place of the organic solvent.  Specified monoepoxy compounds are butyl glycidyl ether, benzyl glycidyl ether and glycidyl ethers of branched monocarboxylic acids.  The specified partially esterified aminodi-alcohol curing agent is represented by the formula:-  <FORM:0977958/D1-D2/1> wherein R1 and R2 are similar or dissimilar saturated hydrocarbon radicals, which may also be directly attached to each other, R3 and R4 each represent an alkyl group, a cylcoalkyl group or a hydrogen atom, A and B are similar or dissimilar alkylene groups, R5 represents a hydrogen atom, a group of the formula:-  <FORM:0977958/D1-D2/2> a monovalent hydrocarbon radical or a monovalent hydrocarbon radical substituted by hydroxy or amino groups, said amino groups being substituted if desired by groups of the formula:-  <FORM:0977958/D1-D2/3> R6 represents the same groups as specified for R5 or a group -NR7R8, and R7 and R8 represents a hydrogen atom, a monovalent hydrocarbon radical or a group of the formula:-  <FORM:0977958/D1-D2/4> Specified polyepoxy compounds are poly (epoxyalkyl) ethers of diphenylol propane, diphenylolethane, diphenyldimethane, diphenylolsulphone, hydroquinone, resorcinol, dihydroxydiphenyl, dihydroxynaphthalenes novolacs, resols, ethylene glycol, glycerol and trimethylopropane; diglycidyl esters of phthalic, terephthalic and adipic acids; epoxidized linseed and soybean oils; diepoxybutane; epoxidized vinylcyclohexane; diglycidyl ether; and the (3, 4-epoxy-6-methyl-cyclohexyl)-methyl ester of 3,4-epoxy-6-methyl-cyclohexane carboxylic acid.